Holiday rentals near Theatre Winter Haven
We found 5,624 holiday rentals — enter your dates for availability
Select the perfect holiday home within close proximity to Theatre Winter Haven. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as parking and a hot tub. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Theatre Winter Haven
Showing deals for:21 Nov - 28 Nov
Image gallery for Lake Front! Spacious Home w/heated pool & kayaks
1010 out of 10 rating
Exceptional
(13 reviews)
Lake Front! Spacious Home w/heated pool & kayaks
Lake Wales, FL
8% off
Price is S$3,603
S$3,603
S$515 nightly
Includes taxes & fees
Image gallery for LAKE HOUSE WITH PRIVATE Free HEATED POOL & GAME ROOM 4 min FROM LEGOLAND
1010 out of 10 rating
Exceptional
(64 reviews)
LAKE HOUSE WITH PRIVATE Free HEATED POOL & GAME ROOM 4 min FROM LEGOLAND
Winter Haven, FL
5% off
Price is S$3,752
S$3,752
S$536 nightly
Includes taxes & fees
Image gallery for Swan City Stay! Home near FSC Lake Hollingsworth, Downtown- walk everywhere!
1010 out of 10 rating
Exceptional
(6 reviews)
Swan City Stay! Home near FSC Lake Hollingsworth, Downtown- walk everywhere!
Lakeland, FL
12% off
Price is S$3,299
S$3,299
S$471 nightly
Includes taxes & fees
Image gallery for Lake Marion Golf Resort Villa
9.49.4 out of 10 rating
Exceptional
(38 reviews)
Lake Marion Golf Resort Villa
Kissimmee, FL
7% off
Price is S$926
S$926
S$132 nightly
Includes taxes & fees
Image gallery for Stunning Lake Front Home on Lake Whistler - Perfect for all the Family to Enjoy!
1010 out of 10 rating
Exceptional
(29 reviews)
Stunning Lake Front Home on Lake Whistler - Perfect for all the Family to Enjoy!
Auburndale, FL
8% off
Price is S$2,386
S$2,386
S$341 nightly
Includes taxes & fees
Image gallery for 🌺 Beautiful Wildflower Escape🌺
9.69.6 out of 10 rating
Exceptional
(27 reviews)
🌺 Beautiful Wildflower Escape🌺
Davenport, FL
15% off
Price is S$1,962
S$1,962
S$280 nightly
Includes taxes & fees
Image gallery for 3 Bedroom Plus Office And Screened In Porch - pet friendly
9.69.6 out of 10 rating
Exceptional
(47 reviews)
3 Bedroom Plus Office And Screened In Porch - pet friendly
Lakeland, FL
8% off
Price is S$1,561
S$1,561
S$223 nightly
Includes taxes & fees
Image gallery for Providence golf club Villa,cul-de-sac,close to Disney Private Large Pool Area
9.89.8 out of 10 rating
Exceptional
(122 reviews)
Providence golf club Villa,cul-de-sac,close to Disney Private Large Pool Area
Davenport, FL
7% off
Price is S$3,001
S$3,001
S$429 nightly
Includes taxes & fees
Image gallery for 9 Bedrooms-sleeps 22!! Mario Themed Game Room!! Avatar themed bedroom!!
9.89.8 out of 10 rating
Exceptional
(29 reviews)
9 Bedrooms-sleeps 22!! Mario Themed Game Room!! Avatar themed bedroom!!
Davenport, FL
7% off
Price is S$5,026
S$5,026
S$718 nightly
Includes taxes & fees
Image gallery for Exceptional villa with themed rooms throughout. Free Pool Heating Sept. 2025
9.09.0 out of 10 rating
Wonderful
(31 reviews)
Exceptional villa with themed rooms throughout. Free Pool Heating Sept. 2025
Davenport, FL
7% off
Price is S$1,943
S$1,943
S$278 nightly
Includes taxes & fees
Image gallery for Festival Resort Townhome |Bunk Room | Captivating Pool Attraction |Splash Zone |Sand Volleyball
8.28.2 out of 10 rating
Very good
(42 reviews)
Festival Resort Townhome |Bunk Room | Captivating Pool Attraction |Splash Zone |Sand Volleyball
Davenport, FL
16% off
Price is S$1,538
S$1,538
S$220 nightly
Includes taxes & fees
Image gallery for Magical Orlando Disney Family Villa
9.69.6 out of 10 rating
Exceptional
(145 reviews)
Magical Orlando Disney Family Villa
Davenport, FL
8% off
Price is S$1,917
S$1,917
S$274 nightly
Includes taxes & fees
Image gallery for Executive 5 Bed 4 Bath Villa - South Facing Pool & Spa only 15 mins from Disney
9.69.6 out of 10 rating
Exceptional
(152 reviews)
Executive 5 Bed 4 Bath Villa - South Facing Pool & Spa only 15 mins from Disney
Davenport, FL
8% off
Price is S$2,781
S$2,781
S$397 nightly
Includes taxes & fees
Image gallery for Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
1010 out of 10 rating
Exceptional
(23 reviews)
Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
Winter Haven, FL
7% off
Price is S$1,908
S$1,908
S$273 nightly
Includes taxes & fees
Image gallery for Ultimate Experience! 8br-Arcade-Theater
1010 out of 10 rating
Exceptional
(23 reviews)
Ultimate Experience! 8br-Arcade-Theater
Davenport, FL
8% off
Price is S$7,191
S$7,191
S$1,027 nightly
Includes taxes & fees
Image gallery for Eagle Haven Lake House
1010 out of 10 rating
Exceptional
(16 reviews)
Eagle Haven Lake House
Eagle Lake, FL
8% off
Price is S$3,943
S$3,943
S$563 nightly
Includes taxes & fees
Image gallery for 4BR 3BA, Access 2 Waterparks, Private Pool, FREE Grill. Near Disney World!
9.89.8 out of 10 rating
Exceptional
(37 reviews)
4BR 3BA, Access 2 Waterparks, Private Pool, FREE Grill. Near Disney World!
Davenport, FL
7% off
Price is S$1,978
S$1,978
S$283 nightly
Includes taxes & fees
Image gallery for (AV8981) Home 5/4 Private Pool & Free Waterpark
9.09.0 out of 10 rating
Wonderful
(15 reviews)
(AV8981) Home 5/4 Private Pool & Free Waterpark
Davenport, FL
7% off
Price is S$2,373
S$2,373
S$339 nightly
Includes taxes & fees
Image gallery for Davenport Retreat w/ Themed Rooms, Patio & Pool!
1010 out of 10 rating
Exceptional
(61 reviews)
Davenport Retreat w/ Themed Rooms, Patio & Pool!
Davenport, FL
6% off
Price is S$2,031
S$2,031
S$290 nightly
Includes taxes & fees
Image gallery for Relax at Southern Exposure in Auburndale with a Pool & 76 Acre Private Lake.
1010 out of 10 rating
Exceptional
(51 reviews)
Relax at Southern Exposure in Auburndale with a Pool & 76 Acre Private Lake.
Auburndale, FL
7% off
Price is S$2,650
S$2,650
S$379 nightly
Includes taxes & fees
Image gallery for Amazing Lakeview 4 BR Vacation Home with Heated Pool! Near All Parks.
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Amazing Lakeview 4 BR Vacation Home with Heated Pool! Near All Parks.
Haines City, FL
8% off
Price is S$2,433
S$2,433
S$348 nightly
Includes taxes & fees
Image gallery for Fabulous 5BR Villa Marvel: Private Pool - Solterra Retreat
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Fabulous 5BR Villa Marvel: Private Pool - Solterra Retreat
Davenport, FL
6% off
Price is S$2,244
S$2,244
S$321 nightly
Includes taxes & fees
Image gallery for Charming lakefront home minutes from downtown Lakeland!
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Charming lakefront home minutes from downtown Lakeland!
Lakeland, FL
8% off
Price is S$2,648
S$2,648
S$378 nightly
Includes taxes & fees
Image gallery for Private Pool-Upgraded Interior-Poolside Bar
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Private Pool-Upgraded Interior-Poolside Bar
Davenport, FL
8% off
Price is S$2,869
S$2,869
S$410 nightly
Includes taxes & fees
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Find the best place to stay - Theatre Winter Haven
Luxury 20 bedroom Reunion Villas @ Disney's Doorstep
Sleeps 44 · 20 bedrooms · 20 bathrooms
9.29.2 out of 10
Wonderfulwonderful
96 reviews(96 reviews)
3 Miles to Disney! Themed Home FREE Heated Pool & Spa Theater Grill & 7 Bedrooms
Sleeps 16 · 7 bedrooms · 6 bathrooms
1010 out of 10
Exceptionalexceptional
183 reviews(183 reviews)
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
Sleeps 20 · 9 bedrooms · 6+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Cozy condo just 11 minutes drive to Walt Disney World® Resort
Sleeps 6 · 2 bedrooms · 2 bathrooms
Newly Renovated Home - Brand New Furniture Throughout - Clubhouse With Pool and Tennis Courts!
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
The Grand Village 4BR Pool Home near Disney Parks
Sleeps 9 · 6 bedrooms · 4 bathrooms
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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
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