A castle entrance with flags and banners, including a LEGO Kingdoms banner.

Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winter Haven vacation rentals

A swimming pool with a fence, lounge chairs, and a palm tree.

1. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (198 reviews)
"Clean room and private area loved it"
United States
Heather
The price is SAR 234
SAR 262 total
includes taxes & fees
29 Oct - 30 Oct
Lake Ida Beach Resort
A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

2. The Russell Lake House

The Russell Lake House
Winter Haven
9.8 out of 10, Exceptional, (25 reviews)
"Nice place!"
United States
Jake D.
The price is SAR 253
SAR 787 total
includes taxes & fees
30 Oct - 31 Oct
The Russell Lake House
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

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

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Winter Haven
9.8 out of 10, Exceptional, (14 reviews)
"Nice house for our stay."
United States
Debi K.
The price is SAR 469
SAR 1,137 total
includes taxes & fees
22 Nov - 23 Nov
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
A modern living room with a grey sofa, a dining area with a round table and chairs, a kitchen with white cabinets, a clock, and a decorative wall piece.

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

Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Winter Haven
10.0 out of 10, Exceptional, (5 reviews)
"This is such a cozy 1 bedroom unit and the side yard was such a great bonus amenity."
United States
Christopher V.
The price is SAR 413
SAR 706 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
A kitchen with white cabinets, a dining table with chairs, and a ceiling fan.

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

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Winter Haven
10.0 out of 10, Exceptional, (4 reviews)
"Nice place very convenient for us. Would stay again"
United States
John G.
The price is SAR 469
SAR 1,092 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

6. Lakefront Vibes w/ Lanai! Bird-watching Paradise

Lakefront Vibes w/ Lanai! Bird-watching Paradise
3.0 star property
Florence Villa
10.0 out of 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
John
Lakefront Vibes w/ Lanai! Bird-watching Paradise
Living area

7. 3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724

3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
Winter Haven
9.4 out of 10, Exceptional, (68 reviews)
"Nice place and convenient"
United States
Tim M.
The price is SAR 469
SAR 1,055 total
includes taxes & fees
27 Oct - 28 Oct
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
A building with a red door, numbered 132C, and a small porch area with a metal stool and a green bucket with a wooden stick.

8. Tiny Paradise

Tiny Paradise
Winter Haven
9.6 out of 10, Exceptional, (17 reviews)
"Check in was easy, this little house had everything we needed! Owner very responsive to needs very quickly through app. We would stay again!"
United States
Cheryl K.
The price is SAR 274
SAR 487 total
includes taxes & fees
22 Nov - 23 Nov
Tiny Paradise
An outdoor hot tub area with a pool, surrounded by chairs and a table.

9. Legoland Splash Escape with pool and hot tub!

Legoland Splash Escape with pool and hot tub!
Winter Haven
10.0 out of 10, Exceptional, (77 reviews)
"Great location"
United States
Michelle
The price is SAR 372
SAR 1,096 total
includes taxes & fees
1 Nov - 2 Nov
Legoland Splash Escape with pool and hot tub!
A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

10. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (8 reviews)
"Very nice house for a small family! Close to everything!"
United States
Yuliett
The price is SAR 171
SAR 877 total
includes taxes & fees
12 Nov - 13 Nov
BlockHaven near Legoland & Disney
A spacious living room with a sofa, a recliner, and a glass coffee table. There is a kitchen area in the background with a microwave and refrigerator.

11. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
9.2 out of 10, Wonderful, (7 reviews)
"Wonderful little cottage filled with fun for the whole family. Cozy backyard to enjoy some sunshine and read a book. Close to downtown shops and restaurants. Owners were quick to respond to questions. Would happily stay here again."
United States
Rachel B.
The price is SAR 432
SAR 1,046 total
includes taxes & fees
27 Oct - 28 Oct
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
A compact living space with a loft bed, a TV mounted on the wall displaying streaming services, a small bathroom, and a wooden floor.

12. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, Wonderful, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
The price is SAR 263
SAR 559 total
includes taxes & fees
27 Oct - 28 Oct
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A wooden house with a porch, steps, and a fenced area with plants.

13. The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia
Winter Haven
9.8 out of 10, Exceptional, (16 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
The price is SAR 450
SAR 1,154 total
includes taxes & fees
6 Nov - 7 Nov
The Old Haven - An Enduring Piece of Nostalgia
A living room with a grey sectional sofa, a white round coffee table, a fluffy rug, and a decorative mirror on the wall.

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

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Winter Haven
9.6 out of 10, Exceptional, (4 reviews)
"Everything was very clean! "
United States
Emilly D.
The price is SAR 507
SAR 868 total
includes taxes & fees
27 Oct - 28 Oct
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

15. Lakefront Vibes w/ Lanai! Bird-Watching Paradise

Lakefront Vibes w/ Lanai! Bird-Watching Paradise
Florence Villa
9.6 out of 10, Exceptional, (29 reviews)
"Nice place to stay for a weekend, had plenty of beds and baths, was clean and close to Lake Silver."
United States
Kelley K.
Lakefront Vibes w/ Lanai! Bird-Watching Paradise
A modern kitchen with a stainless steel refrigerator, white cabinetry, a double sink, and a painting of flowers on the wall.

16. New Haven 5 mi to Legoland & 0.5 mi to dwntwn

New Haven 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
10.0 out of 10, Exceptional, (1 review)
The price is SAR 413
SAR 1,022 total
includes taxes & fees
27 Oct - 28 Oct
New Haven 5 mi to Legoland & 0.5 mi to dwntwn
A kitchen with a dining table, chairs, and a ceiling fan.

17. Cozy 3br 2ba Winter Haven Getaway Chain of Lakes

Cozy 3br 2ba Winter Haven Getaway Chain of Lakes
Winter Haven
10.0 out of 10, Exceptional, (14 reviews)
"The house was really great. It was also very clean, updated, comfortable and very close to great restaurants. Highly recommend this house."
United States
Felix P.
The price is SAR 636
SAR 1,225 total
includes taxes & fees
5 Nov - 6 Nov
Cozy 3br 2ba Winter Haven Getaway Chain of Lakes
A residential area with a large house, a smaller attached garage, and a view of the water.

18. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"Truly great people. We had a wonderful time! Peaceful and relaxing!!"
United States
Jeremy Kyle W.
The price is SAR 338
SAR 664 total
includes taxes & fees
27 Oct - 28 Oct
Charming Lakeside Cottage
Private kitchen

19. Peaceful Place

Peaceful Place
Winter Haven
10.0 out of 10, Exceptional, (28 reviews)
"Great property!"
United States
Glenn C.
The price is SAR 582
SAR 1,652 total
includes taxes & fees
27 Oct - 28 Oct
Peaceful Place
A living room with a brick fireplace, a sofa, a coffee table, and a dining area in the background.

20. Spacious 4-bedroom house in pleasant Winter Haven with AC

Spacious 4-bedroom house in pleasant Winter Haven with AC
Winter Haven
9.6 out of 10, Exceptional, (4 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
Monica
The price is SAR 574
SAR 1,663 total
includes taxes & fees
27 Oct - 28 Oct
Spacious 4-bedroom house in pleasant Winter Haven with AC
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.
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Top Winter Haven Hotel Reviews

Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

8/10 Good
"The property was beautiful. The pools were warmed and the poolside bar was cute. The only negative was that the bar closed at 7:45. The staff at the restaurant were very friendly and attentive."
Nicole 1-night trip
Posted 1 hour ago
Delta Hotels by Marriott Orlando Celebration

Frequently asked questions

Can I find a vacation rental in Winter Haven?

Yes, there are vacation rentals in Winter Haven close to LEGOLAND® Florida, or you can choose a more secluded option if you'd like a relaxing place to stay. Visitors to Winter Haven speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave time to check out the gardens and entertainment venues during your visit.

What's the top vacation rental that Winter Haven has to offer?

Formosa Valley Resort by UNE Homes: This vacation home rental outside Winter Haven is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

How many vacation rentals are there in Winter Haven?

Choose from 53 Expedia vacation rentals in Winter Haven for a memorable vacation.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Peppa Pig Theme Park Florida, whereas The Circle B Bar Reserve and Inman Park are a couple of great spots to enjoy the outdoors. Theatre Winter Haven and Chain of Lakes Park are other places to visit while you're in town.

What are vacation rentals like in Winter Haven?

Vacation rentals are private properties you can book for a few days or a quick weekend in Winter Haven. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.