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Kissimmee Vacation Rentals

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4220 rentals in Kissimmee.
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Veranda Palms Villa
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Disney 5 Star Vacations / The Osprey Villa
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Lovely Affordable Ground Floor Condo at Cane Island Resort
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Luxury Lakeside House with private solar heated pool & spa
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
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Family-Friendly Large Villa with a Pool, Jacuzzi,
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Disney Lakeside Villa with WiFi and a Pool, Kissimmee
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Villa di Lusso
Rental Home
6 bedrooms
10 bathrooms
Sleeps 14
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villanirvana
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Superb 4 Bedroom Home, just 3 minutes from Disney
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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** The Beautiful Palm Oasis Villa at Emerald Island Resort **
Rental Home
7 bedrooms
6 bathrooms
Sleeps 16
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Disney Family Villa pool/spa/games room, 5 bds 4 bathrooms, 15 Mins to Disney
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
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Timeless Memories Villa/Encore near Disney. 8 bedrooms/7bathrooms, pet friendly.
Rental Home
8 bedrooms
7 bathrooms
Sleeps 16
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Fantasy Pool Home
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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A stunning pool home in Kissimmee, Disney Paradi
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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King Palmilla
Rental Home
8 bedrooms
11 bathrooms
Sleeps 18
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Spacious 4-bed lakeside pool villa near Disney
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Debbie's Florida Retreat a Luxury Vacation Home
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Magical Disney Vacation Rental
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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CONSERVATION - HOT TUB - FREE POOL HEAT - Tax Inc
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Lovely villa on Emerald Island-4 miles from Disney
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Brand New 5BD/4BA & private pool home next to Disney & Universal
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
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SUPER Close To Disney, Gameroom, Private Backyard, Lake, Free WiFi, Pool, Spa
Rental Home
7 bedrooms
5 bathrooms
Sleeps 17
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Seven Palms at Waterford Way
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Disneysunnyvilla- 6 Bedroom 4 Bath Villa Rental, 4 miles from Disney
Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
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Magical Memories, Pet-Friendly Home with WiFi
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Bella Vida New Phase 6 bedroom Modern Home
Rental Home
6 bedrooms
7 bathrooms
Sleeps 12
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2674SC - Veranda Palms
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
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Colonial type Villa in a beautiful setting.
Rental Home
6 bedrooms
6 bathrooms
Sleeps 14
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The Charming Mickey's Tree House,
Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
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Beautiful Lakeside Villa With Pool; WiFi
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Oakhill Disney Villa
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Bass Lake Beauty with a Pool, WiFi and Air Conditioning
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Rider's Castle
Rental Home
7 bedrooms
6 bathrooms
Sleeps 14
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8BR Home near Disney - Family Resort *Sleeps 16* w/ Private Pool & Games!
Rental Home
8 bedrooms
5 bathrooms
Sleeps 16
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⭐Spacious 7 Bedrooms Villa w/ Private Pool - Nearby Disney World⭐
Rental Home
7 bedrooms
5 bathrooms
Sleeps 18
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Stunning Sunset Villa includes WiFi, Grill, Gameroom
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Luxurious 5 Bedroom / 3 Bathroom Villa at Lake Berkley - Southern Exposure!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Sonoma Resort 7 Bedroom Vacation Home with Pool (1759)
Rental Home
7 bedrooms
6 bathrooms
Sleeps 17
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5BR Luxury Home - Family Resort - Private Pool, Hot Tub and BBQ!
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
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Luxury 6 Bedroom Home with Pool at Windsor Hills Resort
Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
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Executive Villa with Stunning Lakeviews & South Facing Pool and Spa / Jacuzzi - a dream vacation home
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Stunning 6 bedroom Bella Vida Vacation Home
Rental Home
6 bedrooms
7 bathrooms
Sleeps 16
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Magical Manor, Beautiful Emerald Island Lake View Villa
Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
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Spacious 7BD En-Suite Single Home w/Pool *2606
Rental Home
7 bedrooms
8 bathrooms
Sleeps 17
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Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Cute and Cozy Venetian Bay Vacation Rental Townhome Just 6 Miles to Disney
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Windsor Hills Luxury Home - 5 BR/5BA, Saltwater Pool, Close to Disne
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
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Secret Key Villa - villa rental in Kissimmee, Florida
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Villa Linton - Beautiful Florida Home with Themed Bedrooms
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Regal Oaks Resort -Lovely 1900sq 4BR/4BH,Pool & Slides,3Mi to Disney, Free WiFi
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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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.
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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.