Winter Haven Vacation Rentals

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Featured
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Disney Adventure Villa
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🌴 STAY AT OUR 5 ⭐ Rated Disney Adventure Villa Luxury Home at Windsor Hills Resort. Our Home Features 6 Bedrooms 4 Bathrooms with Private Pool & Spa.

6 Bedrooms
4 Bathrooms
4.89IconIconIconIconIcon
218 reviews
$299 / night (excl. fees & taxes)
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Cute & Cozy Guesthouse in Winter Haven
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Cute & Cozy Guesthouse in Winter Haven

1 Bedroom
1 Bathroom
4.79IconIconIconIconIcon
42 reviews
$65 / night (excl. fees & taxes)
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Newly remodeled Vacation Home with Saltwater Pool
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Winter Haven, Florida near LEGOLAND and near Disney.

3 Bedrooms
2 Bathrooms
$195 / night (excl. fees & taxes)
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Famous Bowling House
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Famous Bowling House

10 Bedrooms
10 Bathrooms
5IconIconIconIconIcon
6 reviews
$745 - $1495 / night (excl. fees & taxes)
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Disney Area Charming house with private pool
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4/3 House in West Haven Community

4 Bedrooms
3 Bathrooms
4.93IconIconIconIconIcon
107 reviews
$180 / night (excl. fees & taxes)
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Beautiful 5 bedroom pool home in Davenport
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SUNNY SOUTH-FACING pool & spa, covered lanai, natural lake view; large outside sunbathing and dining areas, Games room with pool table & air hockey

5 Bedrooms
5 Bathrooms
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1 review
$165 - $260 / night (excl. fees & taxes)
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Global Bowling Villa, sleeps 34
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Global Bowling Villa, sleeps 34

14 Bedrooms
11 Bathrooms
4.7IconIconIconIconIcon
10 reviews
$749 - $1495 / night (excl. fees & taxes)
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Luxury Retreat: Davenport 5bd | Games | Pool Bliss
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Luxury Retreat: Davenport 5bd | Games | Pool Bliss

5 Bedrooms
5 Bathrooms
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2 reviews
$200 / night (excl. fees & taxes)
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14BR/30 Guests-Pool/Spa
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Our 14BR Vacation Villa located at Solterra Resort can accommodate 30+ guests.

14 Bedrooms
11 Bathrooms
5IconIconIconIconIcon
36 reviews
$929 / night (excl. fees & taxes)
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NEW 15BR Disney Villa-Pool, Game Room
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NEW 15BR Disney Villa-Pool, Game Room

10 Bedrooms
10 Bathrooms
5IconIconIconIconIcon
15 reviews
$1086 / night (excl. fees & taxes)
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SALE! 15BR Themed Disney Pool
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NEWLY Remodeled! 15BR 12BA Disney/Pool/Game Room/Theater 32+ Guests

15 Bedrooms
11 Bathrooms
5IconIconIconIconIcon
5 reviews
$979 / night (excl. fees & taxes)
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14 BR 11 BA Villa/30+Resort/Pool/Spa - Near Disney
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14 BR 11 BA Villa/30+Resort/Pool/Spa - Near Disney

10 Bedrooms
10 Bathrooms
4.81IconIconIconIconIcon
42 reviews
$902 / night (excl. fees & taxes)
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Perfect Disney Relaxation
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Private Pool, Water Park, Lazy River, Disney

5 Bedrooms
4 Bathrooms
4.73IconIconIconIconIcon
63 reviews
$245 - $550 / night (excl. fees & taxes)
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VillaMaggiore,Watersong, Disney, SW pool,free view
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VillaMaggiore,Watersong, Disney, SW pool,free view

5 Bedrooms
4½ Bathrooms
4.94IconIconIconIconIcon
48 reviews
$215 - $280 / night (excl. fees & taxes)
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Sunset Palm Villa at Watersong Resort near Disney
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Imagine waking up to glistening lake views, and plunging into your private south-facing pool for a refreshing dip, bathed in year-round sunshine...

5 Bedrooms
4½ Bathrooms
$200 / night (excl. fees & taxes)
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Cosmos Villa
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Cosmos Villa - Luxury Watersong villa close to Disney!

4 Bedrooms
4 Bathrooms
4.83IconIconIconIconIcon
12 reviews
$150 - $310 / night (excl. fees & taxes)
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Oasis Villa with Pool overlooking Pond
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Oasis villa with South facing pool, overlooking pond

5 Bedrooms
4 Bathrooms
$153 - $231 / night (excl. fees & taxes)
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House of Orange at Watersong Resort, Davenport FL
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NEW luxury 4 bedroom, 3.5 bathroom property with own pool and Jacuzzi. Unobstructed view on wood and lake.

4 Bedrooms
3½ Bathrooms
1 Guide
4.93IconIconIconIconIcon
14 reviews
$190 / night (excl. fees & taxes)
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Florida Delight @ Watersong Resort, Davenport, Fl
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Luxurious, spacious 6 Bedroom Family Villa With Private Pool And Spa.

6 Bedrooms
5 Bathrooms
4.9IconIconIconIconIcon
145 reviews
$250 - $280 / night (excl. fees & taxes)
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Heroes Vacation Home
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Walt Disney World & Universal Orlando Getaway: Sunny South Facing Poolside Villa

7 Bedrooms
5½ Bathrooms
4.8IconIconIconIconIcon
10 reviews
$295 - $350 / night (excl. fees & taxes)
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Splendid Solterra
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NEW! Immaculate, Professionally Decorated 12 bedroom Mansion sleeps 24 w/Private Pool, Spa & Grill! Pet Friendly. Free Resort Amenties. Min 2 Disney!

10 Bedrooms
10 Bathrooms
$725 / night (excl. fees & taxes)
    1 – 20 Rentals