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Winter Haven Vacation Rentals

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    Travelers to Winter Haven are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    All 23 Rentals in Winter Haven
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    Winter Haven
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Winter Haven
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    45 Min to Disney 15 Min to Legoland on chain of la1 / 19
    (3)Excellent
    Winter Haven
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Winter Haven
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch with a fully stocked lake. Great for families that want to get away from the hustle and bustle of the busy resorts.This home has one queen bedroom and has a sleeper sofa...
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    Winter Haven, Central Florida 33884
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Winter Haven
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch with a fully stocked lake. Great for families that want to get away from the hustle and bustle of the busy resorts.This home has one queen bedroom and has a sleeper sofa...
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    Winter Haven, Central Florida 33884
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Winter Haven
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch great for families that want to get away from the hustle and bustle of the busy resorts. This home has one queen bedroom with a partitioned den that turns into a second...
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    Winter Haven, Central Florida 33884
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Saltwater Pool Villa Next to Legoland and Near All Disney Attractions1 / 22
    (3)Very good
    Winter Haven
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Yard
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2018
    We had a great time on our vacation. My granddaughter and nephew loved Legoland. Everyday ended with a swim in the pool which was quite refreshing to all of us. The house was...
    Reviewed June 11, 2018
    Very glad that we found this home and was fortunate enough to have rented for the week. Wonderful home that has all the amenities that anyone would need, including convenient...
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    About this property
    This beautiful 2615 sq.ft. 3 bedrooms, 2 bathrooms, saltwater pool home, built in 2010, sits in a gated community in the south of Winter Haven, Florida, and features everything you need for a relaxing vacation. The home provides a large fully screened heated saltwater pool, table tennis (ping...
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    Winter Haven, Central Florida 33884
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Winter Haven
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Internet Access
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch great for families that want to get away from the hustle and bustle of the busy resorts.This home has two bedrooms. A master bedroom with a king size bed and a guest...
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    Location Information
    Winter Haven, Central Florida 33884
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Vacation home 3 Bedroom Next to LEGOLAND1 / 28
    (6)Excellent
    Winter Haven
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Private Yard
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 18, 2018
    The house was exactly as described. Very roomy and clean. It is only a 20 minute walk from the front door of the house to the front gates of Legoland!! Staying in a hotel...
    Reviewed December 15, 2017
    First of all Pedro was very quick in responding to inquiries upfront and everything was clear and clarified before we even arrived. The location was fantastic and the house...
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    About this property
    Nice and Cozy house next to Legoland. Enjoy this magnificent vacation home that has 3 bedrooms it will comfortably accommodate 6 guests. It has a nice back yard and the house is completely furnished and has everything you need to enjoy your vacations with us. Please remember pets are not allowed...
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    Location Information
    Winter Haven, Central Florida 33884
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lakeview Tiny Home by Legoland/Disney w/ boats!1 / 12
    (2)Average
    Winter Haven
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Parking
    • Air Conditioning
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 7, 2018
    Great location for a trip to Legoland. It’s also an easy drive to a variety of eating options in the surrounding communities. Excellent value.
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    About this property
    Welcome to the Daffodil Cottage! A brand new quaint & charming Tiny Home on beautiful Lake Mariana, located near Legoland, Disney World & Bok Tower Gardens! Come try Tiny Life enjoying included kayaks & canoe, fish, or relax around the fire pit! This is a 160 sq ft tiny house with a loft with a...
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    Location Information
    Winter Haven, Central Florida 33881
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Winter Haven
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    • Secure Parking
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious lakefront double-wide home available for the 2017//2018 winter. 2 bedrooms, 2 baths, mud room with washer&dryer, den & Florida room, carport and large storage shed. Recently furnished and equipped. Large dining room and kitchen. Swiss Village Community, Winter Haven, 33881 Grande maison...
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    Location Information
    Winter Haven, Central Florida 33881
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Winter Haven
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lakefront house with Pool on the Chain of Lakes in Winter Haven right next to Winter Haven Municipal Airport. Enjoy the beautiful sunrises and views over the lake. The 2600 Sq ft house is located on a dead end street where there is very little traffic to deal with. It has a split open floor plan...
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    Location Information
    Winter Haven, Central Florida 33881
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Winter Haven
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lakefront house on the Chain of Lakes in Winter Haven right next to Winter Haven Municipal Airport. Enjoy the beautiful sunrise over the lake. The 1300 Sq ft house has 2 bedrooms, 1,5 bathrooms, a large living room with cable TV, an additional sleep sofa in the corner and a desk, a fully equipped...
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    Location Information
    Winter Haven, Central Florida 33881
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    The following rentals are within 5 miles of Winter Haven.
    Low Cost Vacation/Holiday Home Near Golf Courses/Lakes, Nr Disney Orlando  and Tampa1 / 51
    (10)Excellent
    Auburndale
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Air Conditioning
    • Washer
    • Balcony
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 19, 2016
    We stayed in Auburndale for three weeks, because of my job. We enjoyed the neighborhood and the town, and in 40 minutes drive you can reach everything, from the Orlando's parks...
    Reviewed March 27, 2015
    Roy-We really enjoyed staying at your home in Auburndale. It was everything we wanted and more. House is fully equipped with everything you could possibly need, decorated...
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    About this property
    Much loved by Northern State Visitors and Canadians, this gated community home also attracts many Europeans wishing to sample a true American Lifestyle. Situated away from the noisy and impersonal hotels of the tourist areas, yet central to everything and with good communication roads to East and...
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    Location Information
    Auburndale, Florida 33823
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Auburndale
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Yard
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    After a busy day at the theme parks, you will enjoy the respite provided by this serene lakefront pool home! Located in Auburndale, which is between Lakeland and Haines City, you will be just minutes from the Lake Myrtle Sports Complex.  You will also be close to shopping, Legoland, Fantasy of...
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    Location Information
    Auburndale, Florida 33823
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Auburndale
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great home In a wonderful gated community close to all the Disney attractions, Sea world, Universal Studios, 45 minute drive from either Orlando airport or Tampa airport. 1 hour to all the Clearwater area beaches. Heated pool, bocce ball, shuffle board, 18 hole golf course, Tennis courts, weight...
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    Location Information
    Auburndale, Florida 33823
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Auburndale
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    After a big day at the theme parks or the nearby Lake Myrtle Sports Complex, come back to paradise!  Pull up a chair or hop in the private pool and enjoy the amazing lake view and the quiet, serene setting.  And most of all enjoy the 'Southern Exposure' to work on your tan or enjoy the stunning...
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    Location Information
    Auburndale, Florida 33823
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Auburndale
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming Lakefront home with all the feel of a cabin getaway. Located just 2mi south of I-4 at Exit 44, you're just a 30 to 40 minute drive away from Tampa, Disney and Orlando. Or if its the beaches you'd like to visit this little jewel is half way between both coasts leaving your only decision,...
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    Location Information
    Auburndale, Florida 33823
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Auburndale
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Settle into this relaxing 2-bedroom, 2-bathroom vacation rental house in Auburndale! This charming property features all the amenities and comforts of home that you will need to make your stay a relaxing and memorable retreat. The home sleeps up to 4-6 guests, offers access to a community pool and...
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    Location Information
    Auburndale, Florida 33823
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Eloise
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your lakeside paradise awaits at this 4-bedroom, 3-bath Winter Haven vacation rental home, perfect for 12! The home features luxury amenities, including a 26-foot dock, swimming pool, hot tub, gazebo bar, and game room! Spend each day water skiing on Lake Lulu, toasting cocktails on the dock bar,...
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    Location Information
    Eloise, Florida 33880
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Auburndale
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Hot Tub
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gather your family for an East Coast escape at this 2-bedroom, 2-bathroom Auburndale vacation rental house. This spacious home boasts 1,100 square feet of living space and comfortably sleeps 4 with room to accommodate 4 more. The property is situated in a wonderful gated community with access to a...
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    Location Information
    Auburndale, Florida 33823
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Auburndale
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and enjoy a quiet getaway at this corner-lot vacation rental in Auburndale! Nestled on a calm street within a Hamptons Golf Club neighborhood, this 2-bedroom, 2-bath home boasts pleasant views of the neighboring properties and a private, air-conditioned lanai with cozy furnishings. Enjoy...
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    Location Information
    Auburndale, Florida 33823
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Auburndale
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note no guests under the age of 18 are permitted at the property ** Experience the Sunshine State in style when you stay at this renovated 2-bedroom, 2-bath vacation rental house in Auburndale! Suitable for up to 4 travelers situated only 45 minutes from Orlando and 1.5 hours from Cape...
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    Location Information
    Auburndale, Florida 33823
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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