Title: Winter Haven Vacation Home Rentals from CA $236: Search Top Private Vacation Homes for Rent | 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)[Vacation Rentals in Winter Haven](https://expedia.ca/Winter-Haven-Vacation-Rentals.d7464.Travel-Guide-VacationRentals)[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 homes

![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)

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

### BlockHaven near Legoland & Disney

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

CA $93

CA $354 total

includes taxes & fees

Feb 1 - Feb 2

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

![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.ca/Winter-Haven-Hotels-Spacious-4-Bedroom-House-In-Pleasant-Winter-Haven-With-AC.h123115732.Hotel-Information)

Winter Haven

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 $126

CA $506 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)

![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)

![Smart TV](https://images.trvl-media.com/lodging/123000000/122920000/122916100/122916008/751fd822.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)

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

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

Winter Haven

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 $224 total

includes taxes & fees

Jan 29 - Jan 30

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

![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)

![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)

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

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

CA $171

CA $389 total

includes taxes & fees

Jan 27 - Jan 28

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

![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)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/101000000/100610000/100604600/100604549/70c5c728.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Comfort, Pet Friendly, 2 King Beds

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

Winter Haven

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 $141

CA $334 total

includes taxes & fees

Jan 26 - Jan 27

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

![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/1498ca92.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)

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

### Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

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

Winter Haven

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 $171

CA $429 total

includes taxes & fees

Jan 26 - Jan 27

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

![TV](https://images.trvl-media.com/lodging/124000000/123180000/123171400/123171362/80459c5a.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)

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

### Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes

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

Winter Haven

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 $166

CA $470 total

includes taxes & fees

Jan 26 - Jan 27

[](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/110000000/109310000/109302000/109301945/821a5d32.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)

![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)

### Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

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

Winter Haven

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 $171

CA $404 total

includes taxes & fees

Jan 26 - Jan 27

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

![Private kitchen](https://images.trvl-media.com/lodging/110000000/109410000/109405200/109405182/e99c1d69.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)

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

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

CA $215

CA $509 total

includes taxes & fees

Feb 2 - Feb 3

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

![Dining](https://images.trvl-media.com/lodging/74000000/73240000/73230300/73230248/cccedb1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73240000/73230300/73230248/7179b1ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73240000/73230300/73230248/af924fb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73240000/73230300/73230248/0ea4e03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home Away from Home Winter Haven! Disney, Legoland, Bok Tower, Golf, Medical Ctr

[](https://www.expedia.ca/Winter-Haven-Hotels-Disney.h73230248.Hotel-Information)

Winter Haven

9.0/10

Wonderful

(2 reviews)

"I'm town for family graduation party. Perfect place to stay"

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

John S.

CA $274

CA $519 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Winter-Haven-Hotels-Disney.h73230248.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)

![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)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90770000/90766500/90766484/7f3b1bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Winter Haven

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 $111

CA $236 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Winter-Haven-Hotels-PrivateSpacious-1BR-Central-Near-LegoLand-2-Miles.h90766484.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/99000000/98450000/98446800/98446741/13e42009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/99000000/98450000/98446800/98446741/3322689d.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.ca/Winter-Haven-Hotels-Historic.h98446741.Hotel-Information)

Winter Haven

9.8/10

Exceptional

(25 reviews)

"Awesome look forward to future stay "

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

cheryl d.

CA $271

CA $584 total

includes taxes & fees

Jan 26 - Jan 27

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118760000/118757000/118756937/4d01657c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/119000000/118760000/118757000/118756937/f36d6e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118760000/118757000/118756937/ff7875cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/119000000/118760000/118757000/118756937/8ba218ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Friendly Lake House W/ Pool Near Legoland

[](https://www.expedia.ca/Winter-Haven-Hotels-Family-Friendly-Lake-House-W-Pool-Near-Legoland.h118756937.Hotel-Information)

Winter Haven

10/10

Exceptional

(1 review)

"We absolutely loved our stay and highly recommend this home, especially for families! The house was clean, quiet, and spacious, featuring a well-stocked kitchen with high-quality cookware, multiple coffee makers, and kids' essentials. When we weren't at Legoland, we spent our time enjoying the heated salt-water pool, game room, and the dock for fishing and kayaking. Catching the sunrise over the lake was absolutely gorgeous. The hosts were incredibly friendly, flexible, and communicative--adding...

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

Matthew B.

CA $177

CA $639 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Winter-Haven-Hotels-Family-Friendly-Lake-House-W-Pool-Near-Legoland.h118756937.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99310000/99305000/99304918/d280bc7e.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.ca/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

CA $177

CA $353 total

includes taxes & fees

Jan 26 - Jan 27

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

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117390000/117384600/117384508/8475e474.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.ca/Winter-Haven-Hotels-Charming-3-Bedroom-2-Bathroom-Home-In-Brilliant-Winter-Haven.h117384508.Hotel-Information)

Winter Haven

10/10

Exceptional

(2 reviews)

"Wonderful home "

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

Joshlynn

CA $239

CA $299 total

includes taxes & fees

Feb 1 - Feb 2

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

![Interior](https://images.trvl-media.com/lodging/124000000/123610000/123607500/123607499/c6175626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/124000000/123610000/123607500/123607499/76f24c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123610000/123607500/123607499/e18502ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123610000/123607500/123607499/f12ad7e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2-bedroom house in a beautiful Winter Haven area near Legoland and BokTower

[](https://www.expedia.ca/Winter-Haven-Hotels-Cozy-2-Bedroom-House-In-A-Quiet-Delightful-Winter-Haven-Area.h123607499.Hotel-Information)

Winter Haven

CA $185

CA $363 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Winter-Haven-Hotels-Cozy-2-Bedroom-House-In-A-Quiet-Delightful-Winter-Haven-Area.h123607499.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/117000000/116290000/116289700/116289671/94b3721f.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)

### BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!

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

Winter Haven

CA $100

CA $404 total

includes taxes & fees

Feb 2 - Feb 3

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

![Interior](https://images.trvl-media.com/lodging/123000000/122990000/122983100/122983056/7919bd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/123000000/122990000/122983100/122983056/1bf39085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122990000/122983100/122983056/0c4ac3c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122990000/122983100/122983056/54a891f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 7-Bedroom Estate with AC & Resort-Style Pool – Winter Haven

[](https://www.expedia.ca/Winter-Haven-Hotels-Charming-7-Bedroom-Estate-With-AC-Resort-Style-Pool-Winter-Haven.h122983056.Hotel-Information)

Winter Haven

7.4/10

Good

(3 reviews)

"Great houseGreat location"

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

Jose S.

CA $493

CA $1,228 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Winter-Haven-Hotels-Charming-7-Bedroom-Estate-With-AC-Resort-Style-Pool-Winter-Haven.h122983056.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/124000000/123910000/123908200/123908167/e7d7f7b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/124000000/123910000/123908200/123908167/a4be740d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123910000/123908200/123908167/ccd9e8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123910000/123908200/123908167/f8733677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake, Pool, HotTub, Game Room, 8 Beds, Sleeps 17

[](https://www.expedia.ca/Winter-Haven-Hotels-Lake.h123908167.Hotel-Information)

Winter Haven

CA $440

CA $1,288 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Winter-Haven-Hotels-Lake.h123908167.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)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100940000/100934800/100934790/791cc183.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.ca/Winter-Haven-Hotels-Summer-Specials-Pet-Friendly.h100934790.Hotel-Information)

Winter Haven

10/10

Exceptional

(22 reviews)

"The property was immaculate, and the stay was great. It's in a great neighborhood, and the yard is big enough for children to enjoy themselves."

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

Tavares J.

CA $222

CA $583 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Winter-Haven-Hotels-Summer-Specials-Pet-Friendly.h100934790.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=2026-02-08&endDate=2026-02-09&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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=APARTMENT)

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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=COTTAGE)

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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=VILLA)

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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&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=2026-04-25&d1=2026-04-25&endDate=2026-04-28&d2=2026-04-28&lodging=RESIDENCE)

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## Top Winter Haven Hotel Reviews

![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 entire stay was amazing! From the very start to the end. Next time we will for sure be staying longer here."

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

![Holiday Inn Club Vacations at Orange Lake Resort by IHG](https://images.trvl-media.com/lodging/1000000/10000/6400/6315/ac7826b3_y.jpg)

### Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"Spotless rooms and friendly people"

[](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.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

"Room was spotless and the staff was very helpful the resort felt safe and the drinks at the bar was grreat"

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

![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)

![Silver Lake Resort](https://images.trvl-media.com/lodging/1000000/20000/14600/14518/f53cedc1_y.jpg)

### Silver Lake Resort

10/10 Excellent

"Room was comfortable. And cleanvery close to parks"

[](https://expedia.ca/Orlando-Hotels-Silver-Lake-Resort.h14518.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)

## Find out more about Winter Haven

## Winter Haven Vacation Homes information

| Number of reviews | 147                  |
| ----------------- | -------------------- |
| Accommodation     | 24618 Vacation Homes |
| Lowest Price      | CA $236              |
| Highest Price     | CA $639              |

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- [Condo Rentals in Longboat Key ](https://www.expedia.ca/Longboat-Key-Condos.d8409-aaCondos.Travel-Guide-Accommodation)
- [Cottages in Longboat Key ](https://www.expedia.ca/Longboat-Key-Cottages.d8409-aaCottages.Travel-Guide-Accommodation)
- [Country Houses in Longboat Key ](https://www.expedia.ca/Longboat-Key-Country-House.d8409-aaCountryHouse.Travel-Guide-Accommodation)
- [Guest Houses in Longboat Key ](https://www.expedia.ca/Longboat-Key-Guest-Houses.d8409-aaGuestHouses.Travel-Guide-Accommodation)
- [Holiday Park Resorts in Longboat Key ](https://www.expedia.ca/Longboat-Key-Holiday-Parks.d8409-aaHolidayParks.Travel-Guide-Accommodation)
- [Inns in Longboat Key ](https://www.expedia.ca/Longboat-Key-Inns.d8409-aaInns.Travel-Guide-Accommodation)
- [Lodges in Longboat Key ](https://www.expedia.ca/Longboat-Key-Lodges.d8409-aaLodges.Travel-Guide-Accommodation)
- [Motels in Longboat Key ](https://www.expedia.ca/Longboat-Key-Motels.d8409-aaMotels.Travel-Guide-Accommodation)
- [Palaces in Longboat Key ](https://www.expedia.ca/Longboat-Key-Palaces.d8409-aaPalaces.Travel-Guide-Accommodation)
- [Vacation Homes in Longboat Key ](https://www.expedia.ca/Longboat-Key-Private-Vacation-Homes.d8409-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Resorts in Longboat Key ](https://www.expedia.ca/Longboat-Key-Resort-Hotels.d8409-aaResortHotels.Travel-Guide-Accommodation)
- [Townhomes in Longboat Key ](https://www.expedia.ca/Longboat-Key-Townhomes.d8409-aaTownhomes.Travel-Guide-Accommodation)
- [Treehouses in Longboat Key ](https://www.expedia.ca/Longboat-Key-Treehouses.d8409-aaTreehouses.Travel-Guide-Accommodation)
- [Villas in Longboat Key ](https://www.expedia.ca/Longboat-Key-Villas.d8409-aaVillas.Travel-Guide-Accommodation)
- [Aparthotels in Pinellas Park ](https://www.expedia.ca/Pinellas-Park-Apart-Hotels.d9113-aaApartHotels.Travel-Guide-Accommodation)
- [B&B in Pinellas Park ](https://www.expedia.ca/Pinellas-Park-Bed-And-Breakfast.d9113-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Pinellas Park ](https://www.expedia.ca/Pinellas-Park-Guest-Houses.d9113-aaGuestHouses.Travel-Guide-Accommodation)
- [Holiday Park Resorts in Pinellas Park ](https://www.expedia.ca/Pinellas-Park-Holiday-Parks.d9113-aaHolidayParks.Travel-Guide-Accommodation)
- [Inns in Pinellas Park ](https://www.expedia.ca/Pinellas-Park-Inns.d9113-aaInns.Travel-Guide-Accommodation)
- [Lodges in Pinellas Park ](https://www.expedia.ca/Pinellas-Park-Lodges.d9113-aaLodges.Travel-Guide-Accommodation)
- [Motels in Pinellas Park ](https://www.expedia.ca/Pinellas-Park-Motels.d9113-aaMotels.Travel-Guide-Accommodation)
- [Rv Parks in Pinellas Park ](https://www.expedia.ca/Pinellas-Park-RV-Parks.d9113-aaRVParks.Travel-Guide-Accommodation)
- [Riads in Pinellas Park ](https://www.expedia.ca/Pinellas-Park-Riads.d9113-aaRiads.Travel-Guide-Accommodation)
- [Lodges in Polk City ](https://www.expedia.ca/Polk-City-Lodges.d6154853-aaLodges.Travel-Guide-Accommodation)
- [Riads in Polk City ](https://www.expedia.ca/Polk-City-Riads.d6154853-aaRiads.Travel-Guide-Accommodation)
- [Hotels near Walt Disney World® Resort ](https://www.expedia.ca/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels)
- [Hotels near Winter Haven Station ](https://www.expedia.ca/Winter-Haven-Station-Hotels.d6195285.Travel-Guide-Hotels)

- [Flights to Florida ](https://www.expedia.ca/Destinations-In-Florida.d211.Flight-Destinations)
- [Flights from Waco (ACT) to Winter Haven (GIF) ](https://www.expedia.ca/lp/flights/act/gif/waco-to-winter-haven)
- [Flights from Cedar Rapids (CID) to Winter Haven (GIF) ](https://www.expedia.ca/lp/flights/cid/gif/cedar-rapids-to-winter-haven)
- [Flights from Daytona Beach (DAB) to Winter Haven (GIF) ](https://www.expedia.ca/lp/flights/dab/gif/daytona-beach-to-winter-haven)
- [Flights from Grand Rapids (GRR) to Winter Haven (GIF) ](https://www.expedia.ca/lp/flights/grr/gif/grand-rapids-to-winter-haven)
- [Flights from Washington (IAD) to Winter Haven (GIF) ](https://www.expedia.ca/lp/flights/iad/gif/washington-to-winter-haven)
- [Flights from McAllen (MFE) to Winter Haven (GIF) ](https://www.expedia.ca/lp/flights/mfe/gif/mcallen-to-winter-haven)
- [Flights from Miami (MIA) to Winter Haven (GIF) ](https://www.expedia.ca/lp/flights/mia/gif/miami-to-winter-haven)
- [Flights from Montreal (YUL) to Winter Haven (GIF) ](https://www.expedia.ca/lp/flights/yul/gif/montreal-to-winter-haven)
- [Flights from Toronto (YYZ) to Winter Haven (GIF) ](https://www.expedia.ca/lp/flights/yyz/gif/toronto-to-winter-haven)
- [Flights from Toronto (YYZ) to Orlando (MCO) ](https://www.expedia.ca/lp/flights/yyz/mco/toronto-to-orlando)

- [Chain of Lakes Park ](https://www.expedia.ca/Chain-Of-Lakes-Park-Winter-Haven.d6127913.Vacation-Attraction)
- [Indigo's Family Fun Center ](https://www.expedia.ca/Indigos-Family-Fun-Center-Winter-Haven.d6259153.Vacation-Attraction)
- [Legoland® Florida ](https://www.expedia.ca/LEGOLAND-Florida-Winter-Haven.d6153639.Vacation-Attraction)

- [Car rentals near LEGOLAND® Florida ](https://www.expedia.ca/Car-Rentals-In-LEGOLAND-Florida.d6153639.Car-Rental-Guide)
- [Rental cars Winter Haven Municipal airport ](https://www.expedia.ca/Car-Rentals-In-Winter-Haven-Municipal.d6064276.Car-Rental-Guide)
- [Hertz Rental Cars in Winter Haven Municipal ](https://www.expedia.ca/Hertz-Car-Rentals-In-Winter-Haven-Municipal.d6064276-c40.Car-Rental-Guide-Suppliers)

- [Things to do in Eagle Lake ](https://www.expedia.ca/Things-To-Do-In-Eagle-Lake.d3000431007.Travel-Guide-Activities)

- [Book Vacation Homes in Winter Haven on Expedia.com ](https://www.expedia.com/Winter-Haven-Private-Vacation-Homes.d7464-aaPrivateVacationHomes.Travel-Guide-Accommodation)