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Winter Haven Family & Kid Friendly Rentals

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$1,000+
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49 rentals in Winter Haven.
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Are you ready to get back to Living? This is a GREAT place to start. Come!
6 bedrooms
5 bathrooms
Sleeps 12
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Spectacular Waterfront Home in Winter Haven
4 bedrooms
4 bathrooms
Sleeps 10
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FALL/WINTER SPECIAL RATES Mid-century Mod w/ Fireplaces - Downtown Near Legoland
2 bedrooms
3 bathrooms
Sleeps 6
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College Students! Off Campus Life!
3 bedrooms
2 bathrooms
Sleeps 8
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Disney 45 minutes away! LegoLand 10 minutes away!!!
3 bedrooms
2 bathrooms
Sleeps 9
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Private Pool Paradise with Outdoor TV 2.5 miles to Legoland & close to Disney!
3 bedrooms
2 bathrooms
Sleeps 6
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Snowbird - Central Florida - Waterfront / Bord de lac
2 bedrooms
2 bathrooms
Sleeps 5
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Upscale modern 2 Bedrooms Condo On Southern Dunes Golf Gated Community.
2 bedrooms
2 bathrooms
Sleeps 6
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Low Cost Vacation/Holiday Home Near Golf Courses/Lakes, Nr Disney Orlando and Tampa
2 bedrooms
2 bathrooms
Sleeps 4
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Sailors Loch
4 bedrooms
3 bathrooms
Sleeps 8
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Lake Home with 4 Bed/4 Bath & Pool with Diving Board
4 bedrooms
4 bathrooms
Sleeps 12
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Mariner Cay Villa at Southern Dunes Golf and Country Club
3 bedrooms
2 bathrooms
Sleeps 6
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1628 Forest Hills Lane
5 bedrooms
3 bathrooms
Sleeps 10
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Spacious farmhouse in 100 acres of ranch close to Legoland
4 bedrooms
5 bathrooms
Sleeps 12
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Just Bring Your Toothbrush
3 bedrooms
2 bathrooms
Sleeps 7
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Lakefront Grove House
1 bedroom
2 bathrooms
Sleeps 3
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KISSIMMEE'S KNIGHT CASTLE
7 bedrooms
5 bathrooms
Sleeps 20
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Winter Haven Home with Dock & Hot Tub!
4 bedrooms
3 bathrooms
Sleeps 12
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Golf Course and Disney World, Legoland
2 bedrooms
2 bathrooms
Sleeps 4
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☀️ UNIQUE SCANDINAVIAN LUXURY VILLA ☀️ Exclusive with Private Pool & Golf View
4 bedrooms
3 bathrooms
Sleeps 9
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Lakefront Hideaway on Private Lake
3 bedrooms
2 bathrooms
Sleeps 8
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Beautiful vacation home
4 bedrooms
3 bathrooms
Sleeps 8
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Stunning Over 50 Gated Golf and Modular Home Community
2 bedrooms
2 bathrooms
Sleeps 4
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Perfect Home For Your Florida Vacation!
3 bedrooms
2 bathrooms
Sleeps 6
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Southern Beauty With Private Pool
3 bedrooms
2 bathrooms
Sleeps 6
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West Facing Private Pool Home
4 bedrooms
3 bathrooms
Sleeps 8
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Private Pool Home!
3 bedrooms
2 bathrooms
Sleeps 6
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Citrus Sun Private Pool Home & Game Room
5 bedrooms
3 bathrooms
Sleeps 10
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South Facing Pool/Spa in Southern Dunes!
6 bedrooms
4 bathrooms
Sleeps 10
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Belle's Southern Dream in Southern Dunes
4 bedrooms
3 bathrooms
Sleeps 8
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Lakefront Auburndale Home w/ Resort Amenities
2 bedrooms
2 bathrooms
Sleeps 4
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Private Pool Home Conservation View
4 bedrooms
2 bathrooms
Sleeps 8
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Farm House Stay 5 Miles to Legoland!
3 bedrooms
1 bathroom
Sleeps 6
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55+ community, Sleeps 6-8, Minimum monthly rental, Pets Considered
2 bedrooms
2 bathrooms
Sleeps 6
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55 Plus Golf Community 2 Bed/Den, Lanai, Backyard Deck, Grill, Golf, Pool
1 bedroom
2 bathrooms
Sleeps 2
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Citrus Sun Private Pool Home & Game Room
5 bedrooms
3 bathrooms
Sleeps 10
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South Facing Pool/Spa in Southern Dunes!
6 bedrooms
4 bathrooms
Sleeps 10
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Belle's Southern Dream in Southern Dunes
4 bedrooms
3 bathrooms
Sleeps 8
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Perfect Home For Your Florida Vacation!
3 bedrooms
2 bathrooms
Sleeps 6
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Southern Beauty With Private Pool
3 bedrooms
2 bathrooms
Sleeps 6
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Scenic View From Your Private Pool!
3 bedrooms
2 bathrooms
Sleeps 6
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Private Pool Home!
3 bedrooms
2 bathrooms
Sleeps 6
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West Facing Private Pool Home
4 bedrooms
3 bathrooms
Sleeps 8
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SD5016HC - 2 beds condo - Gated resort
2 bedrooms
2 bathrooms
Sleeps 4
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Safe and Clean, We Utilize CDC Approved Products and Standards, Stay With Us!,
4 bedrooms
3 bathrooms
Sleeps 6
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Stunning 4 Bd Single Family w/ Pool & Lake View 175
4 bedrooms
5 bathrooms
Sleeps 10
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1122MCD
4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful 4 Bed Home With South Facing Pool 1108MC
4 bedrooms
3 bathrooms
Sleeps 8
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Impressive 4BR Private Pool Gated Golf Community
4 bedrooms
3 bathrooms
Sleeps 8
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