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Kissimmee Vacation Rentals

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    Travelers to Kissimmee are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    All 6,763 Rentals in Kissimmee
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    Beautiful 6 bedroom Home1 / 36
    (4)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Prestige 4: Ultimate Luxury Windsor at Westside, South Facing Pool/Spa, GameRm1 / 29
    (2)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    Spacious 7 Bedroom home at Bella Vida1 / 24
    (1)Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Satellite TV
    • Washer
    • Patio
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For your next trip to the Orlando area, indulge in spacious living for the entire family by staying at this exquisite Kissimmee vacation rental house. Located in the backyard of Disney World within a pristine gated community, this gorgeous residence will quickly become your home-away-from-home in...
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    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 8 Bathrooms, Sleeps 16
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5-bedroom suite, 6 bathrooms. Accommodates up to 10 guests comfortably and has a fully equipped kitchen. This townhome is equipped with high-speed wireless internet all throughout the unit, free of charge. **PLEASE NOTE: Summerville Resort is a BRAND NEW community, some parts of the resort are...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
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    • Satellite TV
    • Wi-Fi
    • Children's Pool
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Rosa "THE BEST DISNEY VACATION WE EVER HAD!" For what you would expect to pay for a Hotel Room, you can stay at our 5-Star, Luxury Villa that is just 2-miles from Disney World. Have a casual breakfast before you leave for the parks. Then, stop back in the afternoon for a relaxing lunch by...
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    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    6 Bedrooms, 5 Bathrooms, Welcome to the SINGLE FAMILY HOME of your dreams in Kissimmee!! This 6 bedroom and 5 bathroom rental home located in the Storey Lake Resort Community. The 6 bedrooms and 2 living rooms, all together with 8 LED TVs. The large kitchen is a chef’s dream to cook in, with...
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    Kissimmee, Central Florida 34746
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    A hideaway dream - an amazing spacious family home1 / 45
    (3)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 16, 2017
    A lovely spacious villa in a quiet neighbourhood but very close to many restaurants and amenities.The south facing garden was nicely warm to come back to after a full say out.
    Reviewed April 3, 2017
    We rented this place for our business trip...but it was more than we expected...close to major highways, restaurants, supermarkets, yet far enough to be private. We love the...
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    About this property
    A home from home, the British owners spend as much time as possible in the villa themselves. The villa is situated on a large lot and the private south facing heated pool and jacuzzi back onto a wooded area. Pool heating for cooler months is available for an additional charge. This large, 4...
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    Kissimmee, Central Florida 34747
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Central Heating
    • Washer
    • Hot Tub
    • Patio
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 4,000 sq. ft. home is in the new Windsor at Westside gated community (sister community to Windsor Hills) and just minutes from Disney. 8 bedrooms and 6 bathrooms, with 4 en-suites. Pool area with stunning LAKEVIEW, heated SOUTH-FACING pool and Jacuzzi. Game room with seating, pool table and...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    Villa Betty Boo at Hampton Lakes1 / 34
    (3)Average
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Patio
    • Grill
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 15, 2016
    Great place to stay! I was nervous since I had never rented a house before. Bernie (owner) was great at answering all of my questions with in 12 hours after emailing her. The...
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    About this property
    Villa Betty Boo is on the prestigious Hampton Lakes Community which has a swimming pool, basketball, volleyball and tennis courts for your free use. Hampton Lakes is beautifully landscaped and is a very secure community. Villa Betty Boo has 4 spacious bedrooms and can sleep 8 - 9 people + infants...
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    Location Information
    Kissimmee, Central Florida 33897
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Look no further for your perfect "magic" holiday here at Magic Villa situated within the luxurious Emerald Island Resort. This spacious villa has been refurbished to a luxurious standard, which provides everything you could possibly need for a relaxing, stress free stay, on the doorstep of the...
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    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Jacken Villa Great for Large Families, 10 mins to Disney, Central location1 / 17
    (11)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Private Outdoor Pool (Heated)
    • Parking
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Had a wonderful time while vacationing at your home.. The home was very clean and well stocked. Kids enjoyed the pool and there was plenty of space.
    Reviewed June 21, 2017
    Perfect venue for a family gathering. It had great furnishings, bedding, kitchen, pool, and game room for all our needs. Check-in was simple and responsiveness of the...
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    About this property
    This beautiful and spacious villa with a private pool is in Calabria- a small exclusive villa estate in Kissimmee. With 5 bedrooms and 4.5 bathrooms including 2 master en-suite bedrooms, the villa is well designed for 2 families to share. The villa is furnished to an extremely high standard,...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    LAST MINUTE TRAVEL ONLY 179 per night KID FRIENDLY HOME NOW THRU SEPT1 / 27
    (2)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Internet Access
    • Washer
    • Satellite TV
    • Air Conditioning
    • Children's Pool
    • DVD Player
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 4, 2016
    The house was amazing, it had everything we needed and plenty of space. Paula was wonderful about addressing any questions we had. We will be staying again for sure. Our family...
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    About this property
    Private gated community with Beautiful Club house. No one comes close to the Paradise Palms amenities. Our house sits on a corner lot only one block from the clubhouse. Featuring a private pool and Jacuzzi in a screened lanai with seating for dining.When entering the front door you are greeted...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    Paradise Palms. Private Pool. Walk to clubhouse.1 / 23
    (17)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Washer
    • Sauna
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 26, 2017
    Our check-in at the remote office location was very easy and smoothly processed. We arrived at our 4 bedroom villa and was pleased with the looks. Immediately we noticed that...
    Reviewed November 9, 2016
    Nice place to stay. Clean and convenient. I would stay there again. It was exactly what we were looking for.
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    About this property
    This fantastic vacation home in Paradise Palms Resort will provide you with the vacation experience of a lifetime and all the comforts of home. The home is 5-star new construction and offers a private pool, 4 bedrooms, 3 bathrooms and 1,780 square feet of space. The private SOUTH FACING pool is...
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    Kissimmee, Central Florida 34747
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Fantastic Five Bed1 / 18
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 20, 2016
    Had a fantastic holiday with my family... crammed so much in with only a weeks stay at this lovely villa which had everything you could need. Had an issue with one of the door...
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    About this property
    This beautiful 5 bed home is over 2 levels. The sparkling pool overlooks a lake with conservation beyond and is an idyllic setting for your Kissimmee stay. The bottom level has wooden flooring. Here you can relax on the bold striped sofa and watch the flat screen TV. There is also a separate...
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    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Indian Creek this villa is situated in one of the closest residential communities to the Disney Theme Parks area, and less than a 30 minute drive from the Orlando Premium Outlets and Orlando International Airport this beautifully furnished five bedroom four bathroom pool home is perfect...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    The Seasons Villa, lake view and 4 master bedrooms1 / 29
    (4)Excellent
    Downtown Kissimmee
    6 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Hot Tub
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 18, 2017
    This condo was perfect for our family of 8. Clean and beautifully decorated. Big bedrooms and baths. The only thing I can say negative is it wasnt cool enough and had to use...
    Reviewed April 27, 2017
    Love it everyone in my party loved staying here. It was a close trip to all the places we wanted to visit. Mainly Disney.
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    About this property
    This luxury villa has all you need to enjoy a family vacation. You can sit at the pool or in the spa and watch the wildlife on the lake. There are no rear neighbours to worry about here. There is plenty of living space to spread out and relax in the lounge or take it easy in the comfortable sitting...
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    Kissimmee, Central Florida 34746
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 13
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    5 Bedr at Storey Lake mins to Disney! Modern decor1 / 32
    (2)Excellent
    Downtown Kissimmee
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The overall townhome was spacious and clean and very nicely decorated! My kids loved the pool and I was impressed with the layout of the neighborhood. I don't think there was a...
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    About this property
    Welcome to your Disney vacation Home! - Great swimming pool and spa - Accommodates up to 11 people - 5 bedrooms, 4 bathrooms - 1 Master Suite with King size bed; - 1 Master Suite with Queen size bed; - 2 bedrooms with full size bed. - 1 bedroom with bunk beds ( 1 full size and 1 twin bed) - New...
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    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Roughtallys Villa1 / 59
    (10)Excellent
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • Washer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Patio
    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 18, 2017
    Great location for everything(as long as you have a car). Villa clean and spacious offering comfortable accommodation in very quiet surroundings. Outside the views of the lake...
    Reviewed March 31, 2017
    truly a nice and comfortable house. The pool and spa area is great for relaxing. The location is perfect, close to everything. The little lake just behind the house is great...
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    About this property
    Roughtallys is our luxurious villa situated on a 24 hour secure gated community 15 minutes from Disney,s Main Gate. 20 minutes from Universal/Island of Adventure. local superstore and restaurants 2 minutes drive. or a lovely walk.... we can sleep 14 plus a cot and two travel cots. exceptionally...
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    Kissimmee, Central Florida 34746
    Rental Home - 7 Bedrooms, 4 Bathrooms, Sleeps 14
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    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    his vacation home was renovated recently. We put lots of efforts to keep our house at the top of the line. We sincerely welcome all of our guests and feel honor to have your unforgettable memories in our house. It has 3 King Bedrooms, 2 Queen bedrooms, 6 Twin Beds in 3 kid rooms, 4.5 bathrooms,...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 5 Bathrooms, Sleeps 16
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    LAKESIDE HAVEN, Windward Cay, The "hidden jewel" of Kissimmee1 / 30
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 20, 2017
    This is a really lovely 3 bedroomed villa which is extremely comfortable and well equipped (including rain ponchos, which we needed lots!) the pool backs onto a lovely lake so...
    Reviewed May 29, 2017
    Me and my family had a fabulous time staying at the villa. The villa had everything you could wish for and was extremely well equipped. We loved the homely touches and the BBQ...
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    About this property
    Our beautiful, spacious fully air conditioned private villa is located on a fantastic large plot with fantastic views over a large lake and in the peaceful community of Windward Cay 'the hidden jewel of Kissimmee' and yet less than 1 mile from the 192 with all the shops,entertainment and...
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    Kissimmee, Central Florida 34746
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Golden Palms1 / 100
    (3)Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
    • Washer
    • DVD Player
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 24, 2015
    Our family of 4 generations stayed here July 25 to Aug. 4, 2015. It was absolutely perfect for us all. Great grandparents could get in naps, while the great grandkids played in...
    Reviewed December 30, 2014
    Very well decorated, very liveable home. Between the heated pool and hot tub and free wifi, family kept busy and never turned on any of the many flat screen tv's. Home is close...
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    About this property
    Golden Palms is a luxury villa of the highest quality in Orlando, Florida. The villa is well appointed with fine furniture and fully air conditioned with additional ceiling fans through out. With a large South facing pool and spa Golden Palms is the perfect holiday home. Located in the stunning...
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    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 16
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    Kissimmee Townhouse 4 bedrooms1 / 26
    (10)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Private Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 18, 2017
    From the condo to the the Club House amenities, the stay was perfection. The place would comfortably sleep two couples and four children. We will come back for sure!
    Reviewed October 21, 2016
    This house was great. Very close to Wal Mart, Target, etc. as well as restaurants and Disney parks. We were there with our 3 adult children, son in law and one grandchild for...
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    About this property
    BRAND NEW!! MODERN, PROFESSIONALLY DECORATEDProperty Type: 4 Bedrooms / 3 Bath Townhome with Private PoolFloor Area: 1800 sq. ft.Location: Paradise Palms Resort, Disney Area This beautiful unit is located in Paradise Palms Resort one of Florida's Premier Resorts only 5 minutes from Disney!! and...
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    Location Information
    Kissimmee, Central Florida 37474
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Disney Fireworks View B/yard,  3 Miles To Disney1 / 24
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Hot Tub
    • Waterfront
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Satellite TV
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 10, 2015
    The house was exact how the pictures were. Only thing is jacuzzi was cold and pool was freezing. Owner didnt think it should be warmed but it rained alot and the water was...
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    About this property
    ** Enjoy priceless and magnificent view of the Disney's fireworks and gorgeous sunrise from the privacy of backyard patio, theater, pvt pool & spa backing on pond. We also have another property, right next door, check-out : flipkey - vacation-rentals listing # p1070613 Property Highlights:...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    La Retraite Secrete  (The Secret Retreat)1 / 68
    (10)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 1, 2017
    Love it, the kitchen had all the supplies, the house was clean. The pool was big. The owner or in person in charge Claire, had great customer service. Quick response time.
    Reviewed April 24, 2017
    Me and my family (total of seven) stayed in the house for 16 days and we have only one word to describe it.... PERFECT. The house is beutiful, well equipped and the south facing...
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    About this property
    La Retraite Secrete is our stunning home away from home villa offering 4 bedrooms 3 baths, and a private pool. The villa is located on one of TripAdvisor's top vacation spots in Terra Verde resort, Kissimmee, FL. Recently renovated to suit anyone's requirements to our high standard of vacation...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Executive villa nr Disney Parks with heated pool, Jacuzzi and high speed WiFi1 / 51
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    • DVD Player
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2017
    This rental was exactly as described, bright,spacious and clean. Fully equipped, with everything you would require to make this stay worry free and enjoyable. Pool and jacuzzi...
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    About this property
    This luxury home is set in a very quiet residential neighbourhood and within easy reach (15 to 20 minutes) of all the Disney theme and water parks, Universal Studios and Islands of Adventure, Sea World, Legoland, etc. The Buena Vista Shopping Mall is about a 5 minutes drive and a further 10...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4716 CL Pet Friendly1 / 24
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 2016
    Overall great vacation rental. Our family of 10 included 4 children and 6 adults. There was plenty of room for all of us. Loved having the pool to come back to after a long...
    Reviewed April 21, 2016
    My students and I were thrilled when we arrived in this home. The rooms were clean, beds were comfy, and there was a television in every room. The pool was perfect after...
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    About this property
    5 bedroom 4 baths, 2 half baths Sleeps 10 Master with En-Suite bathroom, with Queen sized bed Master 2 with En-Suite bathroom: Queen sized bed, pool can be accessed from this bedroom. Master 3 with En-Suite bathroom: King sized bed Bedroom 4: Two Twin sized beds Bedroom 5: Two Twin sized beds...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Homely 4BR with 2 Master Suites, Kissimmee1 / 80
    (11)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • Washer
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Very beautiful house!Just like the photos. Pool cleaners came by to clean the pool. Lawn maintenance also made. Peaceful gorgeous location, near everything you might want to...
    Reviewed 5 weeks ago
    We rented this home for a volleyball tourney at the OCCC. There were only 4 of us, so this was much more of a house then we needed. First, the pictures are actually pretty...
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    About this property
    Ready to have your dream Florida vacation? You're gonna need a dream house!<BR><BR>This vacation villa has 4 bedrooms, 3 bathrooms, and is totally teeming with luxury! Get ready to dive into the exclusive community of Hamilton's Reserve, which offers extreme privacy and maximum fun! From here...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Washer
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the magic of Orlando at this magnificent 5-bedroom, 3-bathroom Kissimmee vacation rental house which sleeps 10. Offering a private pool, outdoor dining area and a close proximity to Disney World - your unforgettable getaway begins here! You’ll know you made the right choice upon your...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Scotsman's Retreat1 / 70
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • Balcony
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 27, 2015
    We stayed here for eight night's with two family's, having four children all the ensuites really helped especially when trying to get ready in a morning with teenagers!.We have...
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    About this property
    Scotsman's Retreat is a beautiful and quiet 2 storey 5 bedroom house house on Cumbrian Lakes which is a relatively new gated community build in a conservation area and, as the names suggests, based around 3 large lakes. The villa is situated in an ideal location with an extended pool deck with a...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Orlando Vacation house with Boat/RV parking1 / 105
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Balcony
    • DVD Player
    • Hot Tub
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    My Family and I stayed in this wonderful home in April 2017. The home is located in a very peaceful neighborhood. The back yard is very spacious with a little playground perfect...
    Reviewed May 1, 2017
    This place was a great get away for our family of five. It was really clean an modern place. We loved the pool and how quiet it was. The owner give you step to step on how to...
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    About this property
    Come and enjoy Kissimmee, Florida! This beautiful home is located off Neptune road two miles away from Downtown Kissimmee and one mile away from the Florida Turnpike exit. This property is located in a private ½ of acre lot making it perfect for someone traveling with a boat, travel trailer or...
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    Location Information
    Kissimmee, Central Florida 34744
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury 5 BR 4 BA Pool Home w/Game Room Near Parks1 / 22
    (6)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 7, 2017
    House was well supplied with everything we needed. Very convenient location to all parks. This home was the perfect setting for our Disney Vacation. Hope to return again in a...
    Reviewed August 9, 2016
    Superb. That's all I can say. Clean, accommodating, 20 mins from the park. 7 mins from Walmart to stock the home.
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    About this property
    Stunning brand new 5 Bedroom villa in the prestigious Calabria sub-division of Kissimmee, Florida. Built in 2013. Less than 6 miles from Disney World. Top quality furnishings and decor throughout. Flat screen TVs in all bedrooms. Game Room. FREE Wi-Fi. Air-conditioned throughout, the villa extends...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Emerald Magic Villa by Emerald Island Rentals1 / 48
    (7)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Children's Pool
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 31, 2016
    we had a great time, and the house was everything we expected, we will recomended to all our friends and for furthert trios it will be our number one choice.
    Reviewed August 2, 2015
    I cannot begin to say how pleased we were with the home. The beds were great, the rooms large, every possible accessory that could be thought of was provided. The pool was...
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    About this property
    A 6 bed/5.5 bath villa in Emerald Island Resort offering outstanding amenities such as an air-conditioned game room and a south-facing pool/spa. With 4 king master suites and 2 themed kids rooms, this villa can accommodate up to 14 in sheer luxury. The large pool and spa area with a south facing...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Large 3-Bedroom Resort Villa Near Disney1 / 25
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Sauna
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 17, 2016
    chris is an awesome person that will take care of your concerns immediately!totally satisfied with our stay at the resort.
    Reviewed August 27, 2015
    Above and beyond our expectations! My wife and I are very particular about where we stay. The rooms were immaculate, staff was very friendly and helpful, amenities were great...
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    About this property
    This spacious and luxurious condo is great for families and very close to Disney and is situated on a large resort property is plenty of great activities. There are a total of 5 beds in the villa. The master bedroom features a king size bed, a large jacuzzi, and a master bathroom. The second...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Downtown Kissimmee
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The new Storey Lake resort is in one of the best locations of the city, just 10 minutes from Disney Parks, 5 minutes from Lake Buena Vista Outlet and convenient access to nearby shopping, dining and entertainment. The homes, from 4 to 6 bedrooms that can accommodate comfortably up to 12 people, are...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Kissimmee, Florida, "Amazing Castle in the Sun"1 / 140
    (19)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Satellite TV
    • Washer
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 29, 2017
    We were close to universal and even closer to Disney, we enjoyed the pool and hot tub, very comfortable poolside furniture. The beds were comfy, and so was the living room...
    Reviewed April 9, 2016
    Lovely private villla situated in a quiet community, 15 minutes drive from most attractions. Well equipped just like a home from home. Lovely private pool and garden area...
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    About this property
    ********** AMAZING CASTLE IN THE SUN ************* IDYLLIC PLACE TO RELAX AFTER ALL THE FUN OF THE DISNEY MAGIC *** LUXURY VILLA WITH A COMPLETELY PRIVATE SOUTH FACING POOL * 3 Beds, 2 Baths, 2 Lounges.* CABLE TV's, VCR/DVD* GAMES consoles in bedrooms* GAMES ROOM* FULLY equipped kitchen and utility...
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    Kissimmee, Central Florida 34758
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxurious house with pool and Spa on large lot1 / 28
    (6)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Satellite TV
    • Housekeeping Included
    • Hot Tub
    • Children's Pool
    • Patio
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Stunning home in a great location! Very close to parks, shops and food. Would love to stay there again. Family been going to Florida since 1991 and best house ever stayed in.
    Reviewed 4 weeks ago
    Smooth check in, expect everything that you see on the pictures!! Beautiful community, we came for Disney but lots of activities to do in the community also. Kids loved the...
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    About this property
    Our. Wonderful holiday home, On Windsor at Westside, a gated community. Our home has a large private South East facing pool and spa. The screened patio / lanai has been extended to give more room to sunbath. Or to lounge and relax. The largest on the community. Guests also have access to a gas...
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    Kissimmee, Central Florida 34747
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    Villa Toscana1 / 57
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 31, 2014
    Amazing place, amazing location. Very welcoming home after a long day at the plentiful Orlando attractions
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    About this property
    This beautiful home is decorated and furnished to a high standard. Tile, niches, and archways give home the extra quality look. The fully equipped kitchen is complete with a breakfast bar. This exceptional home also has the advantage of two master bedrooms with private en-suite bathrooms. The villa...
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    Kissimmee, Central Florida 34747
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Grand Opening! luxury Disney Villa for large group1 / 30
    (1)Excellent
    9 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Children's Pool
    • DVD Player
    • Housekeeping Included
    • Satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 12, 2016
    The home was very spacious and beautifully decorated. We had a large group and everyone was comfortable. Booking the home was easy, and Tracy was very accommodating. I would...
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    About this property
    This luxurious brand new vacation home is located in the Windsor at Westside, a prestigious resort community - with short drive to DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends. The 4382 sq. ft. living space is professionally furnished with upscale...
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    Kissimmee, Central Florida 34747
    Rental Home - 9 Bedrooms, 6 Bathrooms, Sleeps 22
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    Seasons Delight, Beautiful 5 Bedroom Villa in Kissimmee1 / 91
    (3)Excellent
    Downtown Kissimmee
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Yard
    • Parking
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 26, 2017
    We truly enjoyed our stay. The villa is beautifully decorated and clean with many amenities. The pool and spa were well-heated and the location was most convenient that is...
    Reviewed June 21, 2016
    This was a beautiful home, that was fully equipped for my families needs (12 in family). There was always plenty of hot water and the kitchen was fully stocked with dishes we...
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    About this property
    Beautiful 5 bed villa in Kissimmee, Florida, the holiday destination of the world. Just 10 minutes from Disney in one of the most sought after communities in Orlando. Our villa is luxuriously furnished, with its own secluded pool & spa, a fabulous games room and minutes away from all the best...
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    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Outstanding Orange Blossom Villa includes Gameroom, Jacuzzi, and WiFi1 / 116
    (9)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Washer
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 18, 2017
    Great house and location. Plenty of amenities to use, which helps when you are at the parks all day. Looking forward to a staying in this house again soon!
    Reviewed June 27, 2016
    Really nice house confit nice pool the place is really beautiful with 4 bedrooms the bathrooms is really nice kichen is good side the house is clean
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    About this property
    Luxury 4 bed / 3 bath detached villa with private heated pool / spa, FREE wifi internet connection and games room on High Grove Gated Community, 10 mins from Disney. The villa is easy to find and situated at the junction of the 192 and Highway 27. It is ideally located for the theme parks, golf and...
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    Location Information
    Kissimmee, Central Florida 34714
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Private Swimming Pool, Arcade, Minutes to Disney!1 / 28
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 31, 2014
    we stayed here for 2 weeks in aug 2014 with our extended family of nine,villa is so spacious and large no one got on top of each other everything is provided for your stay...
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    About this property
    Take a break from visiting the parks at Mickey's Oasis. Located less than 5 miles from the park gates, this Indian Creek home just went through over $15,000 in upgrades. It features 5 bedrooms, 4 full bathrooms, with 2 master suites, a fully equipped kitchen, full-size washer and dryer, and your...
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    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Lovely Lake Berkley Villa with a Gameroom and Hot Tub1 / 70
    (11)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 13, 2017
    This is the second time we've stayed here. In all our travels over the years, it's the only holiday home we've returned to - we liked it so much. It is really comfortable and...
    Reviewed March 8, 2017
    This is a lovely and comfortable house where you can have a great time with family or friends. It is fully equipped, which makes you feel at home. The swimming pool is great, we...
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    About this property
    South Facing Pool!!!! Luxury 5 Bedroom Villa in Lake Berkley gated community One storey villa situated in the prestigious Lake Berkley Resort gated community. South facing pool and spa for all day sun. This is a basic must in Florida. Why go to the sun in order to sit in the shade for most of the...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    43075 BV1 / 20
    (2)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 23, 2016
    We just finished up a 5 night stay in this property it was very well laid out roomy beautiful high ceiling in living room area. Well maintained clean terrific linen package and...
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    About this property
    5 Bedroom, 3.5 Bathroom Sleeps 10 people Master 1 with En-suite Bathroom: King Size Bed Master 2 with En-suite Bathroom: Queen Size Bed Bedroom 3: King Size Bed Bedroom 4: 2 X Twin Size Beds Bedroom 5: 2 X Twin Size Beds Pool can be heated for an extra charge. No smoking is allowed at this home....
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Best Lakeside Villa at Paradise Palms in Kissimmee1 / 34
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 6, 2017
    My vacation rental was wonderful (looked just like the pictures). It was everything that I expected.
    Reviewed April 25, 2017
    This a great place to stay especially if you are visiting the theme parks in Orlando. Our kids loved having the pool outside our sliding door, but they really loved the short...
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    About this property
    Built as a Tropical Oasis and refuge away from the hustle and bustle of the nearby attractions, Paradise Palms Resort allows residents to enjoy some of the Very Best Entertainment in the world, while living in a Relaxing, Full-Service Resort environment that caters to your every need. Located in...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    The Perfect 6 Bed Resort Home,1 / 29
    (6)Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 4, 2015
    The property was perfect for our needs and more. It was in a perfect location for everything we wanted to see and do. The kids in particular loved the pool.
    Reviewed March 22, 2015
    We were looking for a home with three things in mind - convenience, (amenities, access to golf courses, etc.) space (had several family members of varying ages and interests...
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    About this property
    If you are looking for a dream home in a dream location you need look no further. This home has it all! It is located in Terra Verde which is one of the top resorts in the Disney area. The gated community has a Club House with pool, spa, tikki bar plus fitness and games rooms. You can even access...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Wilderness Lodge, the villa for a luxury holiday1 / 77
    (5)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Washer
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 27, 2015
    The house was really excellent and had all of the conveniences of home .I would highly recommend it.
    Reviewed February 27, 2015
    There were 13 of us including 5 children from1-9 and everyone was very comfortable. You can't get much closer to Disney without staying in Disney. Very clean in a nice quite...
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    About this property
    Wilderness Lodge is a large premier villa located in the beautiful Emerald Island Resort. It has a south facing private pool plus spa with amazing views over a beautiful lake and woodland conservation area. The Emerald Island Resort is one of the closest to Disney World, yet secluded enough to...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Lumiere's Chateau - Spa and Disney Fireworks View1 / 74
    (1)Average
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
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    • Satellite TV
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    • Patio
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 8, 2014
    The place is nice but needs some TLC. TV's in all rooms are out dated (90's) and small. The only HD TV is in the living room. Bedrooms decor could be better and most towels...
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    About this property
    Lumiere's Chateau, a 5BR, 4BA home with a jacuzzi, is a great place for you to enjoy some rest after a day at the parks, golf courses and exploring everything Orlando has to offer. Lumiere's Chateau is quiet, spacious and nicely decorated. This home has ceramic tile flooring throughout the common...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Grill
    • Parking
    • Shared Yard
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wilderness Lodge is a large premier villa located in the beautiful Emerald Island Resort. It has a south facing private pool plus spa with amazing views over a beautiful lake and woodland conservation area. The Emerald Island Resort is one of the closest to Disney World, yet secluded enough to...
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    Location Information
    Kissimmee, Central Florida 34747
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Disney & Minions Modern 4 bed decor close to parks1 / 27
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
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    Reviewed March 20, 2017
    The location is amazing! This is a great family-friendly condo with a stunning pool and wonderful kitchen. The stay was wonderful !!! I'll love to visit again!
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    About this property
    Comfortable home for your family to enjoy your Disney vacation! Townhouse with private pool near Disney. Sleeps up to 8 people. 4 bedrooms and 3 bathrooms, 1 suite. All bedrooms have TV. 1st FLOOR: - Tiled floors in the 1st. floor, except for the bedroom. - 1st bedroom with king size bed and TV. -...
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    Location Information
    Kissimmee, Central Florida 34746
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Peak travel: March - April
    Kissimmee Vacation Rentals

    Don’t automatically think you need to rent a vacation home in Orlando to be close to Walt Disney World. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate—as well as a very short commute to the parks.

    Kissimmee Vacation Rentals for Families

    More and more families are choosing to celebrate major events like birthdays and anniversaries with a multi-generational trip to Disney World. (It’s one of the few destinations where everyone from toddlers to seniors can have an equally great time.) And we can help you find a Kissimmee vacation rental that can handle any size family. Whether you’re interested in a one-bedroom condo rental in Kissimmee or a seven-bedroom luxury villa, our helpful vacation rental reviews make your selection easy.

    Advantages of renting a vacation home in Kissimmee

    Let’s be honest—while it’s great fun to spend a week visiting the Magic Kingdom, Epcot, Disney’s MGM Studios, Universal Studios and Islands of Adventure, for most of us, it’s a significant strain on our bank accounts. Staying in a hotel and eating in Orlando-area restaurants also adds up. However, we can help you find a great deal on a villa rental in Kissimmee… and even if you just take a few meals in your vacation home instead of in restaurants, your budget will thank you. You’ll even save money on baggage fees with a rental—when you’ve got your own washer and dryer, you can do a few loads of laundry and pack much less clothing.

    Rent a vacation house with a pool in Kissimmee, Florida

    How do you visit the Orlando theme parks and maintain your sanity? Escape the crowds in the mid-afternoon, when the heat peaks and everybody’s nerves are frazzled. By staying just a short distance away in Kissimmee, you can zip home for a refreshing dip in the pool. Little kids can nap in the comfortable A/C of your Kissimmee vacation rental. You’ll all return to WDW or Universal in a much better mood!

    Rental deals in Kissimmee

    Remember that Florida’s a year-round vacation destination—but it definitely has an off-season when you can snag a great deal on Kissimmee condo rentals. If you really want a bargain, plan to visit Kissimmee between Thanksgiving and Christmas. Your condo will be cheap, the parks will be less crowded, and if you’re coming from a northern climate, the weather in Kissimmee will still seem great compared to what you’d get at home.

    Kissimmee and Orlando beyond Disney

    Don’t forget, there’s more to this part of Florida than Mickey and Donald and friends. Animal lovers will want to spend a day at Sea World, or take a day trip to the Everglades. Shoppers should save time (and suitcase space) for bargain-hunting at outlets in Kissimmee and the nearby Orlando Premium Outlets. Just over an hour away, on Florida’s Space Coast, you’ll find the Kennedy Space Center and fantastic sandy beaches like Cocoa Beach. Taking a Disney Cruise departing from Port Canaveral? A vacation rental in Kissimmee is the perfect pre-cruise accommodation.

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