
Winter Haven holiday rentals
We found 14,548 holiday rentals — enter your dates for availability
If you'd like to stay close to Winter Haven, FL (GIF-Winter Haven Municipal), scroll through and discover holiday rentals to choose your home away from home. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the amenities that you need and want, including air conditioning and Wi-Fi. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Winter Haven, FL (GIF-Winter Haven Municipal)
Showing deals for:7 Nov - 14 Nov
Image gallery for mid century modern authors architectural pool home now with pool heat!

9.49.4 out of 10 rating
Exceptional
(85 reviews)
mid century modern authors architectural pool home now with pool heat!
Lakeland, FL
16% off
Price is S$2,204
S$2,204
S$315 per night
includes taxes & fees
Image gallery for Heated Pool and Hot tub-near Legoland, Disney, Theme parks

9.89.8 out of 10 rating
Exceptional
(31 reviews)
Heated Pool and Hot tub-near Legoland, Disney, Theme parks
Winter Haven, FL
15% off
Price is S$2,265
S$2,265
S$324 per night
includes taxes & fees
Image gallery for Mulberry Garden Cottage

9.49.4 out of 10 rating
Exceptional
(26 reviews)
Mulberry Garden Cottage
Mulberry, FL
10% off
Price is S$826
S$826
S$118 per night
includes taxes & fees
Image gallery for Perfect spacious home with pool, ideal for families visiting Disney or golfers

9.69.6 out of 10 rating
Exceptional
(166 reviews)
Perfect spacious home with pool, ideal for families visiting Disney or golfers
Davenport, FL
7% off
Price is S$2,020
S$2,020
S$289 per night
includes taxes & fees
Image gallery for Luxury 12 Bed / 14 Bath Villa in Reunion Resort

9.49.4 out of 10 rating
Exceptional
(86 reviews)
Luxury 12 Bed / 14 Bath Villa in Reunion Resort
Kissimmee, FL
7% off
Price is S$11,157
S$11,157
S$1,594 per night
includes taxes & fees
Image gallery for ☀️ Outstandning & Lavish Luxury Villa ☀️ Private Pool & Spa & Golf Course View ⛳

9.89.8 out of 10 rating
Exceptional
(123 reviews)
☀️ Outstandning & Lavish Luxury Villa ☀️ Private Pool & Spa & Golf Course View ⛳
Haines City, FL
11% off
Price is S$1,713
S$1,713
S$245 per night
includes taxes & fees
Image gallery for Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure

1010 out of 10 rating
Exceptional
(22 reviews)
Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure
Winter Haven, FL
18% off
Price is S$2,005
S$2,005
S$286 per night
includes taxes & fees
Image gallery for Peaceful home with Pool Dog friendly 4 Bedrooms 3 Bathrooms backyard view water.

9.89.8 out of 10 rating
Exceptional
(36 reviews)
Peaceful home with Pool Dog friendly 4 Bedrooms 3 Bathrooms backyard view water.
Davenport, FL
10% off
Price is S$1,698
S$1,698
S$243 per night
includes taxes & fees
Image gallery for Arcades, Pool Table, Bubble Soccer, Mario Bros Bedroom, Giant Scrabble: The Hideaway

9.49.4 out of 10 rating
Exceptional
(45 reviews)
Arcades, Pool Table, Bubble Soccer, Mario Bros Bedroom, Giant Scrabble: The Hideaway
Kissimmee, Florida
7% off
Price is S$6,990
S$6,990
S$999 per night
includes taxes & fees
Image gallery for Arcade, Caribbean Pool Area, Foosball, Waterpark, 15 mins to Disney: The Springs

9.69.6 out of 10 rating
Exceptional
(21 reviews)
Arcade, Caribbean Pool Area, Foosball, Waterpark, 15 mins to Disney: The Springs
Davenport, FL
7% off
Price is S$5,080
S$5,080
S$726 per night
includes taxes & fees
Image gallery for Luxury large 6 Bed Villa, Pool and Spa. Make memories - 15 minutes from Disney

8.48.4 out of 10 rating
Very good
(132 reviews)
Luxury large 6 Bed Villa, Pool and Spa. Make memories - 15 minutes from Disney
Davenport, FL
8% off
Price is S$2,252
S$2,252
S$322 per night
includes taxes & fees
Image gallery for Charming Suite In The Heart Of Lakeland

9.29.2 out of 10 rating
Wonderful
(61 reviews)
Charming Suite In The Heart Of Lakeland
Lakeland, FL
7% off
Price is S$689
S$689
S$98 per night
includes taxes & fees
Image gallery for ⭐⭐⭐⭐⭐ChampionsGate, 9 Bed Luxury Exec Villa, Sleeps 30, West Facing Pool & Spa

9.29.2 out of 10 rating
Wonderful
(84 reviews)
⭐⭐⭐⭐⭐ChampionsGate, 9 Bed Luxury Exec Villa, Sleeps 30, West Facing Pool & Spa
Davenport, FL
16% off
Price is S$3,690
S$3,690
S$527 per night
includes taxes & fees
Image gallery for Luxury resort mansion with swim up bar,pool slide,restaurants, golf, and Disney!

9.69.6 out of 10 rating
Exceptional
(37 reviews)
Luxury resort mansion with swim up bar,pool slide,restaurants, golf, and Disney!
Kissimmee, FL
7% off
Price is S$13,314
S$13,314
S$1,902 per night
includes taxes & fees
Image gallery for Modern Townhouse, Balmoral Resort Haines City Vacation Rentals

9.69.6 out of 10 rating
Exceptional
(15 reviews)
Modern Townhouse, Balmoral Resort Haines City Vacation Rentals
Haines City, FL
7% off
Price is S$1,381
S$1,381
S$197 per night
includes taxes & fees
Image gallery for 5BR Executive Villa Large Pool Gated Community in Championsgate area near Disney

1010 out of 10 rating
Exceptional
(119 reviews)
5BR Executive Villa Large Pool Gated Community in Championsgate area near Disney
Davenport, FL
8% off
Price is S$2,262
S$2,262
S$323 per night
includes taxes & fees
Image gallery for 6 Bed, 5 Bath Villa with South Facing Pool, located close to Disney & Universal

9.69.6 out of 10 rating
Exceptional
(80 reviews)
6 Bed, 5 Bath Villa with South Facing Pool, located close to Disney & Universal
Davenport, FL
7% off
Price is S$2,373
S$2,373
S$339 per night
includes taxes & fees
Image gallery for Charming lakefront home minutes from downtown Lakeland!

9.89.8 out of 10 rating
Exceptional
(30 reviews)
Charming lakefront home minutes from downtown Lakeland!
Lakeland, FL
8% off
Price is S$2,662
S$2,662
S$380 per night
includes taxes & fees
Image gallery for Lakefront Lego Land Estate

9.89.8 out of 10 rating
Exceptional
(27 reviews)
Lakefront Lego Land Estate
Winter Haven, FL
12% off
Price is S$4,457
S$4,457
S$637 per night
includes taxes & fees
Image gallery for 10 min to Disney, private pool home on luxury resort, brand new hardwood floors.

9.29.2 out of 10 rating
Wonderful
(47 reviews)
10 min to Disney, private pool home on luxury resort, brand new hardwood floors.
Kissimmee, FL
11% off
Price is S$5,640
S$5,640
S$806 per night
includes taxes & fees
Image gallery for Fall and Holidays Special! Near Disney+Legoland

9.89.8 out of 10 rating
Exceptional
(43 reviews)
Fall and Holidays Special! Near Disney+Legoland
Davenport, FL
7% off
Price is S$3,911
S$3,911
S$559 per night
includes taxes & fees
Image gallery for Spacious & Private North Lakeland Getaway w/ Pool - 50 Minutes to Disney!

8.68.6 out of 10 rating
Excellent
(10 reviews)
Spacious & Private North Lakeland Getaway w/ Pool - 50 Minutes to Disney!
Lakeland, FL
7% off
Price is S$2,789
S$2,789
S$398 per night
includes taxes & fees
Image gallery for Reunion BRAND NEW Fancy Vacation Home

9.49.4 out of 10 rating
Exceptional
(18 reviews)
Reunion BRAND NEW Fancy Vacation Home
Kissimmee, FL
13% off
Price is S$3,804
S$3,804
S$543 per night
includes taxes & fees
Image gallery for Welcome To Our Beautiful Villa In The Gorgeous Community Solterra!

9.89.8 out of 10 rating
Exceptional
(203 reviews)
Welcome To Our Beautiful Villa In The Gorgeous Community Solterra!
Davenport, FL
7% off
Price is S$2,536
S$2,536
S$362 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winter Haven
Charming 2-bedroom house with huge yard and firepit in Eagle Lake
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Resort Pool & Arcade: Family Townhome in Davenport
Sleeps 12 · 4 bedrooms · 3+ bathrooms
Last Minute Disney Getaway! Private Pool & Themed Bedrooms. Book Now! #138091
Sleeps 10 · 4 bedrooms · 3+ bathrooms
Grand EXEC Golf 4BR Pool Home Near Disney
Sleeps 8 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Cozy lake house vacation getaway close to Orlando theme parks!
Sleeps 12 · 2 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
5 reviews(5 reviews)
Serene, Cozy, Lakefront home
Sleeps 7 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value