Title: Winter Haven Vacation Rentals from $101: Search Short-Term Rentals | Expedia.com

[Winter Haven Travel Guide](https://expedia.com/Winter-Haven.dx7464)[Hotels in Winter Haven](https://expedia.com/Winter-Haven-Hotels.d7464.Travel-Guide-Hotels)[Flights to Winter Haven](https://expedia.com/Cheap-Flights-To-Winter-Haven.d7464.Travel-Guide-Flights)[Things to do in Winter Haven](https://expedia.com/Things-To-Do-In-Winter-Haven.d7464.Travel-Guide-Activities)[Car Rentals in Winter Haven](https://expedia.com/Car-Rentals-In-Winter-Haven.d7464.Car-Rental-Guide)[Winter Haven Vacation Packages](https://expedia.com/Winter-Haven.d7464.Destination-Travel-Guides)

![Winter Haven showing rides](https://images.trvl-media.com/place/7464/a00f555f-1771-4135-ad57-834cb1a10a56.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/7464/a00f555f-1771-4135-ad57-834cb1a10a56.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=7464&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=7464&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=7464&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=7464&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winter Haven vacation rentals

![Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/e68ec5ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/0fd93fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/018b394c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/3291fd43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BlockHaven near Legoland & Disney

[](https://www.expedia.com/Winter-Haven-Hotels-BlockHaven-Near-Legoland-Disney.h116470105.Hotel-Information)

Winter Haven

10/10

Exceptional

(1 review)

"House was great, perfect central location. Very quiet neighborhood nice farm outside peaceful back yard seating area. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Wade

$240 nightly

$268 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-BlockHaven-Near-Legoland-Disney.h116470105.Hotel-Information)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/a66b5fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake view](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/a2866d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Quadruple Room, Non Smoking, Lake View | Living area | TV](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/3f904c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 Queen Bed, Non Smoking | Living area | TV](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/9828479e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake Ida Beach Resort

[](https://www.expedia.com/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information)

Winter Haven

7.2/10

Good

(188 reviews)

"We have stayed here several times. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Martha

$75 nightly

$84 total

Feb 21 - Feb 22

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information)

![Smart TV, foosball](https://images.trvl-media.com/lodging/37000000/36870000/36863800/36863729/9ca0bf77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36870000/36863800/36863729/3f2914a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/37000000/36870000/36863800/36863729/86323ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/37000000/36870000/36863800/36863729/b0a32758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*3/2\*GorgeousNEWLakeHome2AceLoc\*4mi\*LEGOLAND\*1724

[](https://www.expedia.com/Winter-Haven-Hotels-32GorgeousNEWLakeHome2AceLoc4miLEGOLAND1724.h36863729.Hotel-Information)

Winter Haven

9.4/10

Exceptional

(66 reviews)

"The accommodation at this property was exceptional. It felt safe, and was safe Parking was great, proximity to dinning and shopping was withing 5 minutes drive, and the location was peaceful and safe."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dwight

$254 nightly

$281 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-32GorgeousNEWLakeHome2AceLoc4miLEGOLAND1724.h36863729.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100940000/100934800/100934790/1987c5bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100940000/100934800/100934790/f59ce572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100940000/100934800/100934790/eb8496ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/101000000/100940000/100934800/100934790/b5595392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large Family Home, Legoland, Pet Friendly, 7 Beds

[](https://www.expedia.com/Winter-Haven-Hotels-Summer-Specials-Pet-Friendly.h100934790.Hotel-Information)

Winter Haven

10/10

Exceptional

(22 reviews)

"Everything was very nice and comfortable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gary B.

$394 nightly

$435 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Summer-Specials-Pet-Friendly.h100934790.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/108000000/107330000/107322400/107322352/d17a813b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107330000/107322400/107322352/a22bf56c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/108000000/107330000/107322400/107322352/bacea2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107330000/107322400/107322352/b6f089cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tiny Paradise 

[](https://www.expedia.com/Winter-Haven-Hotels-Tiny-Paradise.h107322352.Hotel-Information)

Winter Haven

9.4/10

Exceptional

(8 reviews)

"I have stayed on property a few times, first experience with tiny Paradise very quaint and clean enjoyed my stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

SUSAN

$113 nightly

$124 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Tiny-Paradise.h107322352.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98450000/98446800/98446741/607be1c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98450000/98446800/98446741/6b8b0da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98450000/98446800/98446741/13e42009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/99000000/98450000/98446800/98446741/4cd1e877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events 

[](https://www.expedia.com/Winter-Haven-Hotels-Historic.h98446741.Hotel-Information)

Winter Haven

9.8/10

Exceptional

(27 reviews)

"Awesome look forward to future stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

cheryl d.

$377 nightly

$418 total

Feb 19 - Feb 20

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Historic.h98446741.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/13dc8494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/acae569e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/37041c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/75562742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

[](https://www.expedia.com/Winter-Haven-Hotels-Lovely-Lakefront-Home-W-Grill-7-Mi-To-Legoland.h93532553.Hotel-Information)

Winter Haven

10/10

Exceptional

(3 reviews)

"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John

$394 nightly

$438 total

Feb 21 - Feb 22

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Lovely-Lakefront-Home-W-Grill-7-Mi-To-Legoland.h93532553.Hotel-Information)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/114000000/113260000/113259800/113259758/87ed720d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113260000/113259800/113259758/001816b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113260000/113259800/113259758/51015006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/114000000/113260000/113259800/113259758/2ed863bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven

[](https://www.expedia.com/Winter-Haven-Hotels-Cozy-Grand-Room-1-Bedroom-Apartment-With-WiFi.h113259758.Hotel-Information)

Winter Haven

$127 nightly

$145 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Cozy-Grand-Room-1-Bedroom-Apartment-With-WiFi.h113259758.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99310000/99305000/99304918/cd61c0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99310000/99305000/99304918/ed9a447c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/100000000/99310000/99305000/99304918/9b255241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99310000/99305000/99304918/b11c422f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large 3/1 Near DownTown and Dining 

[](https://www.expedia.com/Winter-Haven-Hotels-Large-31-Near-DownTown-And-Dining.h99304918.Hotel-Information)

Winter Haven

7.4/10

Good

(10 reviews)

"Clean, quiet and comfortable beds. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jason

$230 nightly

$254 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Large-31-Near-DownTown-And-Dining.h99304918.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122920000/122916100/122916008/e2756784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122920000/122916100/122916008/361a40f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122920000/122916100/122916008/9c1a2a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/123000000/122920000/122916100/122916008/751fd822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 1 bedroom home in Winter Haven perfect for your getaway.

[](https://www.expedia.com/Winter-Haven-Hotels-Cozy-1-Bedroom-Home-In-Winter-Haven-Perfect-For-Your-Getaway.h122916008.Hotel-Information)

Winter Haven

10/10

Exceptional

(2 reviews)

"Yes the dogs liked it and they enjoyed walking in the neighborhood."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John W.

$170 nightly

$188 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Cozy-1-Bedroom-Home-In-Winter-Haven-Perfect-For-Your-Getaway.h122916008.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/93000000/92150000/92145300/92145248/w905h683x60y0-a604a4a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92150000/92145300/92145248/w906h683x59y0-101f6b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92150000/92145300/92145248/77022ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/93000000/92150000/92145300/92145248/w508h683x258y0-79e59c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheerful 4 Bed, 3 Bath Home with Screened Pool

[](https://www.expedia.com/Winter-Haven-Hotels-Cheerful-4-Bed.h92145248.Hotel-Information)

Winter Haven

10/10

Exceptional

(24 reviews)

"Very lovely place to stay for a family vacation."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Charley L.

$390 nightly

$432 total

Feb 19 - Feb 20

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Cheerful-4-Bed.h92145248.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119590000/119588800/119588726/0f2dc48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119590000/119588800/119588726/76dc7f3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119590000/119588800/119588726/444edb57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119590000/119588800/119588726/5464b944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene, Cozy, Lakefront Home with Jacuzzi/hot tub and covered porch on the Lake!

[](https://www.expedia.com/Winter-Haven-Hotels-Serene.h119588726.Hotel-Information)

Winter Haven

$305 nightly

$337 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Serene.h119588726.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/6887a27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/a051d1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/3f53f763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/977a192a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

[](https://www.expedia.com/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.Hotel-Information)

Winter Haven

8.8/10

Excellent

(3 reviews)

"Just what we needed for a weekend trip with our grandsons for the weekend "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christine B.

$254 nightly

$279 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/124000000/123120000/123115800/123115732/f6d52a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/124000000/123120000/123115800/123115732/02061239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/124000000/123120000/123115800/123115732/8258d901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/124000000/123120000/123115800/123115732/b0eee200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 4-bedroom house in pleasant Winter Haven with AC

[](https://www.expedia.com/Winter-Haven-Hotels-Spacious-4-Bedroom-House-In-Pleasant-Winter-Haven-With-AC.h123115732.Hotel-Information)

Winter Haven

10/10

Exceptional

(3 reviews)

"An outstanding stay! The house was extremely clean, welcoming, and had all the amenities that made our family vacation unforgettable in our visit to Legoland park"

![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg)

Monica

$409 nightly

$452 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Spacious-4-Bedroom-House-In-Pleasant-Winter-Haven-With-AC.h123115732.Hotel-Information)

![Paper towels](https://images.trvl-media.com/lodging/91000000/90770000/90766500/90766484/4ce05735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90770000/90766500/90766484/98c256c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/91000000/90770000/90766500/90766484/2a155272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/91000000/90770000/90766500/90766484/6eac51d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private/Spacious 1BR Central Near LegoLand 2 Miles

[](https://www.expedia.com/Winter-Haven-Hotels-PrivateSpacious-1BR-Central-Near-LegoLand-2-Miles.h90766484.Hotel-Information)

Winter Haven

9.6/10

Exceptional

(9 reviews)

"Location was great. Internet was great. Bed was good. Cleaned and comfortable.."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maria

$156 nightly

$172 total

Feb 21 - Feb 22

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-PrivateSpacious-1BR-Central-Near-LegoLand-2-Miles.h90766484.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/ebb18c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/5af1b204.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, books](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/ad804664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/435432d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heated Pool and Hot tub-near Legoland, Disney, Theme parks

[](https://www.expedia.com/Winter-Haven-Hotels-Pool-Home-Near-Legoland.h91221257.Hotel-Information)

Winter Haven

9.8/10

Exceptional

(44 reviews)

"We had a great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Harper B.

$326 nightly

$361 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Pool-Home-Near-Legoland.h91221257.Hotel-Information)

![Microwave](https://images.trvl-media.com/lodging/112000000/111460000/111455800/111455786/62c52ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/112000000/111460000/111455800/111455786/55d77a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111460000/111455800/111455786/7d95ac0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/112000000/111460000/111455800/111455786/b6349d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 1-Bedroom Retreat Near Downtown & Legoland

[](https://www.expedia.com/Winter-Haven-Hotels-Cozy-1-Bedroom-Retreat-Near-Downtown-Legoland.h111455786.Hotel-Information)

Winter Haven

10/10

Exceptional

(2 reviews)

$158 nightly

$175 total

Feb 20 - Feb 21

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Cozy-1-Bedroom-Retreat-Near-Downtown-Legoland.h111455786.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117390000/117384600/117384508/dea79e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117384600/117384508/763daf28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117390000/117384600/117384508/085464a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117390000/117384600/117384508/b1f91a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

[](https://www.expedia.com/Winter-Haven-Hotels-Charming-3-Bedroom-2-Bathroom-Home-In-Brilliant-Winter-Haven.h117384508.Hotel-Information)

Winter Haven

10/10

Exceptional

(3 reviews)

"Wonderful home "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joshlynn

$199 nightly

$220 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Charming-3-Bedroom-2-Bathroom-Home-In-Brilliant-Winter-Haven.h117384508.Hotel-Information)

![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109410000/109405200/109405182/b66928f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109410000/109405200/109405182/513516b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109410000/109405200/109405182/0b0e24b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/110000000/109410000/109405200/109405182/e99c1d69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

[](https://www.expedia.com/Winter-Haven-Hotels-Live-Oak-Oasis-Getaway-Close-To-Legoland-Sleeps-8-Guests.h109405182.Hotel-Information)

Winter Haven

10/10

Exceptional

(3 reviews)

"Wonderful stay in Winter Haven for our family Legoland trip, including our dog!The house was spotless, cozy, and easily accommodated all of us.Close to the park, would definitely stay again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Oscar G.

$281 nightly

$311 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Winter-Haven-Hotels-Live-Oak-Oasis-Getaway-Close-To-Legoland-Sleeps-8-Guests.h109405182.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-04&endDate=2026-03-05&regionId=7464&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=COTTAGE)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=VILLA)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=CABIN)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=APART_HOTEL)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=APARTMENT)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=HOUSE_BOAT)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=CHALET)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=RESIDENCE)

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## Top Winter Haven Hotel Reviews

![Westgate Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/410a3d83_y.jpg)

### Westgate Town Center Resort

10/10 Excellent

"Overrall great everything "

[](https://expedia.com/Orlando-Hotels-Westgate-Town-Center-Resort.h426819.Hotel-Information)

![Hilton Vacation Club Mystic Dunes Orlando](https://images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24_y.jpg)

### Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"We had a 2 bedroom villa. The space was large and clean. The kitchen was fully equipped and there was a washer and dryer in the unit. The property was quiet and close to local attractions "

[](https://expedia.com/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information)

![Vacation Village Orlando, Celebration](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/fb6985f5_y.jpg)

### Vacation Village Orlando, Celebration

10/10 Excellent

"Great pool and amenities."

[](https://expedia.com/Orlando-Hotels-Vacation-Village-At-Parkway.h1068973.Hotel-Information)

![Ramada by Wyndham Kissimmee Gateway](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/b94616ba_y.jpg)

### Ramada by Wyndham Kissimmee Gateway

10/10 Excellent

"The location was great. The room was clean a a very good size!"

[](https://expedia.com/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information)

![Westgate Vacation Villas Resort](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/b8afec09_y.jpg)

### Westgate Vacation Villas Resort

10/10 Excellent

"Very nice! And got upgraded to a nicer villa! Very close to Disney World. "

[](https://expedia.com/Orlando-Hotels-Westgate-Vacation-Villas-Resort.h98920.Hotel-Information)

![Holiday Inn Resort Kissimmee by the Parks by IHG](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b_y.jpg)

### Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent

"Staff and location"

[](https://expedia.com/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information)

![Holiday Inn & Suites Orlando SW - Celebration Area by IHG](https://images.trvl-media.com/lodging/1000000/10000/7900/7855/e4318c5d_y.jpg)

### Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent

"Staff is great!"

[](https://expedia.com/Orlando-Hotels-Holiday-Inn-Orlando-SW-Celebration-Area.h7855.Hotel-Information)

![The Grove Resort & Water Park Orlando](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg)

### The Grove Resort & Water Park Orlando

10/10 Excellent

"We were on our Honeymoon Love the nice clean room I can’t wait to return Love the porch and my View"

[](https://expedia.com/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information)

![Margaritaville Resort Orlando](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg)

### Margaritaville Resort Orlando

10/10 Excellent

"Yes, room was spotless. Housekeeping was amazing!!"

[](https://expedia.com/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information)

## Find out more about Winter Haven

**Everything you need to know about Winter Haven vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Haven vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Winter Haven vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winter Haven. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Haven in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Winter Haven rentals**

At Expedia, we put the best Winter Haven vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Haven vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
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- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Winter Haven ](https://expedia.com/Winter-Haven-Private-Vacation-Homes.d7464-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Villas in Winter Haven ](https://expedia.com/Winter-Haven-Villas.d7464-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Winter Haven ](https://expedia.com/Winter-Haven-Condos.d7464-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Winter Haven ](https://expedia.com/Winter-Haven-Apartments.d7464-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Winter Haven ](https://expedia.com/Winter-Haven-Cottages.d7464-aaCottages.Travel-Guide-Accommodation)
- [Resorts in Winter Haven ](https://expedia.com/Winter-Haven-Resorts.d7464-aaResorts.Travel-Guide-Accommodation)
- [Town Houses in Winter Haven ](https://expedia.com/Winter-Haven-Town-Houses.d7464-aaTownHouses.Travel-Guide-Accommodation)
- [Aparthotels in Winter Haven ](https://expedia.com/Winter-Haven-Apart-Hotels.d7464-aaApartHotels.Travel-Guide-Accommodation)
- [Guest Houses in Winter Haven ](https://expedia.com/Winter-Haven-Guest-Houses.d7464-aaGuestHouses.Travel-Guide-Accommodation)
- [Motels in Winter Haven ](https://expedia.com/Winter-Haven-Motels.d7464-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Winter Haven ](https://expedia.com/Winter-Haven-Cabins.d7464-aaCabins.Travel-Guide-Accommodation)
- [Chalets in Winter Haven ](https://expedia.com/Winter-Haven-Chalets.d7464-aaChalets.Travel-Guide-Accommodation)
- [B&B in Winter Haven ](https://expedia.com/Winter-Haven-Bed-And-Breakfast.d7464-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Residences in Winter Haven ](https://expedia.com/Winter-Haven-Residences.d7464-aaResidences.Travel-Guide-Accommodation)
- [Condo Resorts in Winter Haven ](https://expedia.com/Winter-Haven-Condominium-Resort.d7464-aaCondominiumResort.Travel-Guide-Accommodation)
- [Houseboats in Winter Haven ](https://expedia.com/Winter-Haven-Houseboats.d7464-aaHouseboats.Travel-Guide-Accommodation)
- [Riads in Winter Haven ](https://expedia.com/Winter-Haven-Riads.d7464-aaRiads.Travel-Guide-Accommodation)
- [Lodges in Winter Haven ](https://expedia.com/Winter-Haven-Lodges.d7464-aaLodges.Travel-Guide-Accommodation)
- [RV Parks in Winter Haven ](https://expedia.com/Winter-Haven-RV-Parks.d7464-aaRVParks.Travel-Guide-Accommodation)
- [Farmstay in Winter Haven ](https://expedia.com/Winter-Haven-Agritourism.d7464-aaAgritourism.Travel-Guide-Accommodation)
- [Holiday Park Resorts in Winter Haven ](https://expedia.com/Winter-Haven-Holiday-Parks.d7464-aaHolidayParks.Travel-Guide-Accommodation)

## Frequently asked questions

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- [Hotels in Pensacola](https://expedia.com/Pensacola-Hotels.d6023331.Travel-Guide-Hotels)
- [Oceanfront Hotels in Panama City Beach](https://expedia.com/Panama-City-Beach-Hotels-Oceanfront-Hotels.0-0-d8021-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [All-inclusive Resorts in Key West](https://expedia.com/Key-West-Hotels-All-Inclusive-Hotel.0-0-d1187-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Daytona Beach](https://expedia.com/Daytona-Beach-Hotels.d6023995.Travel-Guide-Hotels)
- [Beach Hotels in Destin](https://expedia.com/Destin-Hotels-Beach-Hotel.0-0-d6906-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Key West](https://expedia.com/Key-West-Hotels.d1187.Travel-Guide-Hotels)
- [Hotels in Tallahassee](https://expedia.com/Tallahassee-Hotels.d6048214.Travel-Guide-Hotels)
- [Oceanfront Hotels in St. Augustine](https://expedia.com/St-Augustine-Hotels-Oceanfront-Hotels.0-0-d6047864-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in Siesta Key](https://expedia.com/Siesta-Key-Hotels-Oceanfront-Hotels.0-0-d6881-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Panama City Beach](https://expedia.com/Panama-City-Beach-Hotels.d8021.Travel-Guide-Hotels)
- [Hotels in St. Augustine](https://expedia.com/St-Augustine-Hotels.d6047864.Travel-Guide-Hotels)

Flights

- [Cheap Flights to Destin](https://expedia.com/Cheap-Flights-To-Destin.d6906.Travel-Guide-Flights)
- [Cheap Flights to Key West](https://expedia.com/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)
- [Cheap Flights to Fort Myers](https://expedia.com/Cheap-Flights-To-Fort-Myers.d602729.Travel-Guide-Flights)
- [Cheap Flights to Daytona Beach](https://expedia.com/Cheap-Flights-To-Daytona-Beach.d6023995.Travel-Guide-Flights)
- [Cheap Flights to Sarasota](https://expedia.com/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights)
- [Cheap Flights to Pensacola](https://expedia.com/Cheap-Flights-To-Pensacola.d6023331.Travel-Guide-Flights)

Cars

- [Car rentals in West Palm Beach](https://expedia.com/Car-Rentals-In-West-Palm-Beach.d2742.Car-Rental-Guide)

Packages

- [Key West Vacation](https://expedia.com/Key-West.d1187.Destination-Travel-Guides)
- [Destin Vacation](https://expedia.com/Destin.d6906.Destination-Travel-Guides)

General

- [Visit Santa Rosa Beach](https://expedia.com/Santa-Rosa-Beach.dx183118)

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