Title: Winter Haven Vacation Rentals from CA $148: Short-Term Rentals for 2026 | Expedia.ca

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

![Legoland Florida showing signage and rides](https://images.trvl-media.com/place/6153639/fda15cc5-b61f-4932-b081-d6d5e0df3165.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6153639/fda15cc5-b61f-4932-b081-d6d5e0df3165.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 17 - Apr 19](https://www.expedia.ca/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 four months

[May 15 - May 17](https://www.expedia.ca/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)

## Our top choices for Winter Haven vacation rentals

![Luxury House, 3 Bedrooms, Garden View | Living area](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/117000000/116480000/116470200/116470105/3291fd43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Private kitchen](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/435da507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Haven

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

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

CA $94

CA $357 total

includes taxes & fees

Feb 2 - Feb 3

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

![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)

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

### Cottage in Winter Haven

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

10/10

Exceptional

(2 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.

CA $159

CA $386 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/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)

![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)

![Dining](https://images.trvl-media.com/lodging/124000000/123120000/123115800/123115732/5ea52e5d.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)

### Vacation Home in Winter Haven

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

10/10

Exceptional

(2 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

CA $127

CA $511 total

includes taxes & fees

Jan 26 - Jan 27

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

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122920000/122916100/122916008/0ba8f3ed.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)

### Vacation Home in Winter Haven

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

10/10

Exceptional

(1 review)

"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.

CA $121

CA $225 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Winter-Haven-Hotels-Cozy-1-Bedroom-Home-In-Winter-Haven-Perfect-For-Your-Getaway.h122916008.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](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/bf31d8de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Cottage in Winter Haven

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

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

CA $103

CA $116 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.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/b6f089cc.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)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107330000/107322400/107322352/f373cf92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Haven

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

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

CA $87

CA $172 total

includes taxes & fees

Jan 26 - Jan 27

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

![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301941/8b2d5008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301941/0a638022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301941/6e85e90b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301941/a9a2c842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Haven

[](https://www.expedia.ca/Winter-Haven-Hotels-The-Unique-Cozy-Studio.h109301941.Hotel-Information)

10/10

Exceptional

(1 review)

"Cool little place, love the outdoor private patio.Very close to everything downtown"

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

Cory M.

CA $110

CA $252 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Winter-Haven-Hotels-The-Unique-Cozy-Studio.h109301941.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113200000/113197300/113197257/547c4abc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113200000/113197300/113197257/8de6cedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113200000/113197300/113197257/bab180eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113200000/113197300/113197257/7043d524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Haven

[](https://www.expedia.ca/Winter-Haven-Hotels-Clean-And-Cozy-Waterfront-Apt-Near-Legoland.h113197257.Hotel-Information)

10/10

Exceptional

(3 reviews)

"The place was clean and tidy, accessible to a lot of stores and attractions in the surrounding area, and the hosts were SO nice and easy to contact throughout our stay-even checking in on us to make sure everything was going good. Would totally stay again!"

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

Kaitlyn F.

CA $143

CA $187 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Winter-Haven-Hotels-Clean-And-Cozy-Waterfront-Apt-Near-Legoland.h113197257.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)

### Vacation Home in Winter Haven

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

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

CA $172

CA $392 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Winter-Haven-Hotels-32GorgeousNEWLakeHome2AceLoc4miLEGOLAND1724.h36863729.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/94000000/93540000/93532600/93532553/39ee6e2d.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)

### Cottage in Winter Haven

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

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

CA $236

CA $604 total

includes taxes & fees

Feb 3 - Feb 4

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

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/101000000/100610000/100604600/100604549/eeab406a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/101000000/100610000/100604600/100604549/3a6c2050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100610000/100604600/100604549/fd9c8147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100610000/100604600/100604549/21d4d7a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Haven

[](https://www.expedia.ca/Winter-Haven-Hotels-Chain-Of-Lakes-Cottage.h100604549.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Great welcoming and answered every question I had. Highly recommend this lovely cottage. "

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

Kristofer G.

CA $166

CA $365 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Winter-Haven-Hotels-Chain-Of-Lakes-Cottage.h100604549.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/91000000/90770000/90766500/90766484/6eac51d0.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)

### Vacation Home in Winter Haven

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

9.6/10

Exceptional

(8 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

CA $112

CA $238 total

includes taxes & fees

Feb 14 - Feb 15

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

![Interior](https://images.trvl-media.com/lodging/114000000/113260000/113259800/113259758/59133969.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)

### Apartment in Winter Haven

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

CA $118

CA $201 total

includes taxes & fees

Jan 31 - Feb 1

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301945/821a5d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301945/2252853a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301945/5b74241e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301945/739c83aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Haven

[](https://www.expedia.ca/Winter-Haven-Hotels-Cozy-Bungalow-5-Mi-Legoland-05-Mi-Dwntwn.h109301945.Hotel-Information)

10/10

Exceptional

(1 review)

"Nice place very convenient for us. Would stay again"

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

John G.

CA $172

CA $405 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Winter-Haven-Hotels-Cozy-Bungalow-5-Mi-Legoland-05-Mi-Dwntwn.h109301945.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)

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111460000/111455800/111455786/a43cd8ff.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)

### Apartment in Winter Haven

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

10/10

Exceptional

(2 reviews)

CA $176

CA $241 total

includes taxes & fees

Feb 14 - Feb 15

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

![TV](https://images.trvl-media.com/lodging/124000000/123180000/123171400/123171362/029bd53d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123180000/123171400/123171362/ec5304b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/124000000/123180000/123171400/123171362/80459c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123180000/123171400/123171362/1a816804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Haven

[](https://www.expedia.ca/Winter-Haven-Hotels-A-Lake-Downtown-Getaway-In-Charming-Winter-Haven.h123171362.Hotel-Information)

10/10

Exceptional

(1 review)

"The host was very accommodating and responsive. The house is clean, roomy, cute, and comfortable. There is so much to see and do in Winter Haven - I’ll return and stay at Rick’s Retreat again!"

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

Mary R.

CA $217

CA $534 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Winter-Haven-Hotels-A-Lake-Downtown-Getaway-In-Charming-Winter-Haven.h123171362.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/cc04f93a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/887502c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/1498ca92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/db780d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Haven

[](https://www.expedia.ca/Winter-Haven-Hotels-Getaway-Clubhouse-5-Mil-Legoland-5-Mil-Downtown.h109301947.Hotel-Information)

9.8/10

Exceptional

(7 reviews)

"Great location, clean and great communication with hosts "

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

Angie Y.

CA $172

CA $431 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Winter-Haven-Hotels-Getaway-Clubhouse-5-Mil-Legoland-5-Mil-Downtown.h109301947.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/117000000/116290000/116289700/116289671/f5e1ee3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/117000000/116290000/116289700/116289671/686d1d7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dishwasher, coffee/tea maker, electric kettle, blender](https://images.trvl-media.com/lodging/117000000/116290000/116289700/116289671/e1766bc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116290000/116289700/116289671/0841fb0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Haven

[](https://www.expedia.ca/Winter-Haven-Hotels-BlockHaven-Near-Legoland.h116289671.Hotel-Information)

CA $103

CA $414 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Winter-Haven-Hotels-BlockHaven-Near-Legoland.h116289671.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/113000000/112390000/112387600/112387557/d80b1b5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112390000/112387600/112387557/847f98ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112390000/112387600/112387557/fcdb020d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112390000/112387600/112387557/c9851c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Winter Haven

[](https://www.expedia.ca/Winter-Haven-Hotels-Bright-Home-Near-Legoland-Lake.h112387557.Hotel-Information)

10/10

Exceptional

(1 review)

"Beautiful clean home. Lots of amenities. However it here were glass decorations on table. We moved them out of reach of 2 and 4 year old. Otherwise BEAUTIFUL! Definitely would stay here again."

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

Roberta W.

CA $217

CA $535 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Winter-Haven-Hotels-Bright-Home-Near-Legoland-Lake.h112387557.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)

![Dining](https://images.trvl-media.com/lodging/110000000/109410000/109405200/109405182/0b0e24b8.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)

![Living area](https://images.trvl-media.com/lodging/110000000/109410000/109405200/109405182/95487cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Haven

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

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.

CA $216

CA $512 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-02-06&endDate=2026-02-07&regionId=7464&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=CONDO)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=CABIN)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=CHALET)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-23&d1=2026-04-23&endDate=2026-04-26&d2=2026-04-26&lodging=RESIDENCE)

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## Top Winter Haven Hotel Reviews

![Destiny Palms Hotel Maingate West](https://images.trvl-media.com/lodging/1000000/430000/427400/427337/d056f561_y.jpg)

### Destiny Palms Hotel Maingate West

10/10 Excellent

"Good"

[](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.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

"We love it"

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

![LEGOLAND Beach Retreat](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/228a563a_y.jpg)

### LEGOLAND Beach Retreat

10/10 Excellent

"Everything was great!"

[](https://expedia.ca/Winter-Haven-Hotels-LEGOLAND-Beach-Retreat.h30537958.Hotel-Information)

![Delta Hotels by Marriott Orlando Celebration](https://images.trvl-media.com/lodging/1000000/10000/300/256/w4000h2663x0y0-bece67c9_y.jpg)

### Delta Hotels by Marriott Orlando Celebration

10/10 Excellent

"The room was nice and clean. "

[](https://expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.Hotel-Information)

![Hilton Vacation Club Aqua Sol Orlando West](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg)

### Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent

"Just loved the hotel in general! "

[](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.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

"My room was beautiful and very clean we loved the stay . "

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

![Kompose Boutique Resort at Theme Parks](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/3cf09a4a_y.jpg)

### Kompose Boutique Resort at Theme Parks

10/10 Excellent

"Great room. Lots of room "

[](https://expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.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

"Clean room ✅ Comfy bed ✅ Good breakfast✅ Will definitely stay here again."

[](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Orlando-SW-Celebration-Area.h7855.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

"Clean room"

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

## Find out more about Winter Haven

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winter Haven. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Winter Haven ](https://expedia.ca/Winter-Haven-Private-Vacation-Homes.d7464-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Villas in Winter Haven ](https://expedia.ca/Winter-Haven-Villas.d7464-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Winter Haven ](https://expedia.ca/Winter-Haven-Condos.d7464-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Winter Haven ](https://expedia.ca/Winter-Haven-Apartments.d7464-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Winter Haven ](https://expedia.ca/Winter-Haven-Cottages.d7464-aaCottages.Travel-Guide-Accommodation)
- [Resorts in Winter Haven ](https://expedia.ca/Winter-Haven-Resort-Hotels.d7464-aaResortHotels.Travel-Guide-Accommodation)
- [Townhomes in Winter Haven ](https://expedia.ca/Winter-Haven-Townhomes.d7464-aaTownhomes.Travel-Guide-Accommodation)
- [Aparthotels in Winter Haven ](https://expedia.ca/Winter-Haven-Apart-Hotels.d7464-aaApartHotels.Travel-Guide-Accommodation)
- [Guest Houses in Winter Haven ](https://expedia.ca/Winter-Haven-Guest-Houses.d7464-aaGuestHouses.Travel-Guide-Accommodation)
- [Motels in Winter Haven ](https://expedia.ca/Winter-Haven-Motels.d7464-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Winter Haven ](https://expedia.ca/Winter-Haven-Cabins.d7464-aaCabins.Travel-Guide-Accommodation)
- [Chalets in Winter Haven ](https://expedia.ca/Winter-Haven-Chalets.d7464-aaChalets.Travel-Guide-Accommodation)
- [B&B in Winter Haven ](https://expedia.ca/Winter-Haven-Bed-And-Breakfast.d7464-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Residences in Winter Haven ](https://expedia.ca/Winter-Haven-Residences.d7464-aaResidences.Travel-Guide-Accommodation)
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- [Houseboats in Winter Haven ](https://expedia.ca/Winter-Haven-Houseboats.d7464-aaHouseboats.Travel-Guide-Accommodation)
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- [Holiday Park Resorts in Winter Haven ](https://expedia.ca/Winter-Haven-Holiday-Parks.d7464-aaHolidayParks.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Winter Haven?

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Flights

- [Cheap Flights to Sarasota](https://expedia.ca/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights)
- [Cheap Flights to Naples](https://expedia.ca/Cheap-Flights-To-Naples.d602724.Travel-Guide-Flights)
- [Cheap Flights to Fort Myers](https://expedia.ca/Cheap-Flights-To-Fort-Myers.d602729.Travel-Guide-Flights)
- [Cheap Flights to Daytona Beach](https://expedia.ca/Cheap-Flights-To-Daytona-Beach.d6023995.Travel-Guide-Flights)
- [Cheap Flights to Cape Canaveral](https://expedia.ca/Cheap-Flights-To-Cape-Canaveral.d6484.Travel-Guide-Flights)
- [Cheap Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)

Cars

- [Car rentals in Fort Myers](https://expedia.ca/Car-Rentals-In-Fort-Myers.d602729.Car-Rental-Guide)

Activities

- [Things to do in Sarasota](https://expedia.ca/Things-To-Do-In-Sarasota.d602719.Travel-Guide-Activities)
- [Things to do in Boynton Beach](https://expedia.ca/Things-To-Do-In-Boynton-Beach.d6253.Travel-Guide-Activities)
- [Things to do in Fort Myers](https://expedia.ca/Things-To-Do-In-Fort-Myers.d602729.Travel-Guide-Activities)
- [Things to do in Daytona Beach](https://expedia.ca/Things-To-Do-In-Daytona-Beach.d6023995.Travel-Guide-Activities)
- [Things to do in Naples](https://expedia.ca/Things-To-Do-In-Naples.d602724.Travel-Guide-Activities)
- [Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)
- [Things to do in Cape Coral](https://expedia.ca/Things-To-Do-In-Cape-Coral.d6521.Travel-Guide-Activities)
- [Things to do in St. Augustine](https://expedia.ca/Things-To-Do-In-St-Augustine.d6047864.Travel-Guide-Activities)

Packages

- [Key West Vacations](https://expedia.ca/Key-West.d1187.Destination-Travel-Guides)

Vacation Rentals

- [Naples Vacation Rentals](https://expedia.ca/Naples-Vacation-Rentals.d602724.Travel-Guide-VacationRentals)

General

- [Visit Cocoa Beach](https://expedia.ca/Cocoa-Beach.dx6549)

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