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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winter Haven villas

A room with wicker furniture, a glass coffee table, and a view of a green lawn and trees.

1. Resort Villa, Pools Fun and relaxation/w Kingbed.

Resort Villa, Pools Fun and relaxation/w Kingbed.
Kissimmee
8.8 out of 10, Excellent, (32 reviews)
"Shannelle was extremely responsive, informative and friendly. Very nice accomodations. Pleasant stay. "
United States
Joel W.
The price is €217
includes taxes & fees
18 Nov - 19 Nov
Resort Villa, Pools Fun and relaxation/w Kingbed.
A swimming pool with clear water, surrounded by palm trees and a glass enclosure.

2. Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater

Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater
Haines City
8.8 out of 10, Excellent, (95 reviews)
"We had a great, comfortable stay. We had a bit of an issue with the AC but it was resolved promptly."
United States
Yaritza A.
Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater
A residential house with a tiled roof, a palm tree, and a car parked in the driveway.

3. Peacefull villa in Lake Marion Golf Resort,all amenite,35' to the park atraccion

Peacefull villa in Lake Marion Golf Resort,all amenite,35' to the park atraccion
Kissimmee
9.2 out of 10, Wonderful, (10 reviews)
"It was an ok visit "
United States
Cordell G.
Peacefull villa in Lake Marion Golf Resort,all amenite,35' to the park atraccion
A residential house with a blue exterior, a white garage door, and a driveway.

4. Heated Pool Game Room Home Near Disney

Heated Pool Game Room Home Near Disney
2.0 star property
Aylesbury
Heated Pool Game Room Home Near Disney
A swimming pool with a football on the edge, surrounded by a covered area with a view of trees and a building in the background.

5. 129 Seneca Point Trl

129 Seneca Point Trl
4.0 star property
Indian Point
The price is €362
includes taxes & fees
17 Nov - 18 Nov
129 Seneca Point Trl
A two-story house with a garage, stone accents, and a well-maintained lawn.

6. Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!

Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
Davenport
9.0 out of 10, Wonderful, (78 reviews)
"This property was more than expected and we plan to come again because we loved the house and the resort."
United States
Kimberly J.
The price is €707
includes taxes & fees
18 Nov - 19 Nov
Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
A covered outdoor seating area with sofas and chairs, large windows, and a ceiling fan.

7. Solara Resort Home With Private Pool Near Disney

Solara Resort Home With Private Pool Near Disney
3.0 star property
Kissimmee
The price is €292
includes taxes & fees
29 Nov - 30 Nov
Solara Resort Home With Private Pool Near Disney
A building with a white facade, a red umbrella, and a sign that reads "FESTIVAL SQUARE".

8. 1067 3BR Luxury Resort House by Disney Orlando

1067 3BR Luxury Resort House by Disney Orlando
Festival
1067 3BR Luxury Resort House by Disney Orlando
A residential area with a large swimming pool surrounded by lush greenery and a lake.

9. 1052 3BR Luxury Resort House by Disney Orlando

1052 3BR Luxury Resort House by Disney Orlando
Festival
The price is €280
includes taxes & fees
6 Dec - 7 Dec
1052 3BR Luxury Resort House by Disney Orlando
Pool

10. Family-Friendly Disney Villa - Private Pool, Spa & BBQ - 15 Min to Disney

Family-Friendly Disney Villa - Private Pool, Spa & BBQ - 15 Min to Disney
Sandy Ridge
10.0 out of 10, Exceptional, (1 review)
"Loved our stay thank you for hosting us"
United States
Tammy W.
The price is €345
includes taxes & fees
29 Nov - 30 Nov
Family-Friendly Disney Villa - Private Pool, Spa & BBQ - 15 Min to Disney
A covered outdoor swimming pool with lounge chairs and a pergola structure.

11. Gorgeous VILLA near Disney, Private Heated South Pool

Gorgeous VILLA near Disney, Private Heated South Pool
Sandy Ridge
8.8 out of 10, Excellent, (21 reviews)
"My family had a wonderful stay! Would definitely come back! "
United States
Janay P.
The price is €367
includes taxes & fees
8 Nov - 9 Nov
Gorgeous VILLA near Disney, Private Heated South Pool
A two-story building with a symmetrical facade, a central entrance with a door, and a small porch area.

12. Lazy River~Tiki Bar~Pool~Hot Tub~Themed~Disney

Lazy River~Tiki Bar~Pool~Hot Tub~Themed~Disney
Regal Palms
The price is €479
includes taxes & fees
7 Dec - 8 Dec
Lazy River~Tiki Bar~Pool~Hot Tub~Themed~Disney
An aerial view of a resort with a large swimming pool, multiple lounge areas, and a winding water feature.

13. BBQ~Oasis w/Heated Pool~Marvel &Nemo rooms~Near Disney

BBQ~Oasis w/Heated Pool~Marvel &Nemo rooms~Near Disney
Kissimmee
10.0 out of 10, Exceptional, (14 reviews)
"Lots of space great for families! Great communication with host! Would stay again. "
Canada
Heather
BBQ~Oasis w/Heated Pool~Marvel &Nemo rooms~Near Disney
A view through a window with a palm tree logo, dense foliage, and a calm body of water.

14. Bahama Bay Resort - Grand Bahama Penthouse

Bahama Bay Resort - Grand Bahama Penthouse
2.0 star property
Bahama Bay
The price is €384
includes taxes & fees
10 Nov - 11 Nov
Bahama Bay Resort - Grand Bahama Penthouse
A modern townhouse with a flat roof, large windows, and a small patio area with outdoor seating.

15. 8761 ZD - 3 BD The Hub Paradise Cozy Place

8761 ZD - 3 BD The Hub Paradise Cozy Place
Four Corners
8761 ZD - 3 BD The Hub Paradise Cozy Place
An aerial view of a property with a swimming pool, a covered patio, and a large building with multiple windows.

16. Disney Villa with Hot Tub+Grill+Many other amenities

Disney Villa with Hot Tub+Grill+Many other amenities
Bridgewater Crossing
The price is €256
includes taxes & fees
15 Nov - 16 Nov
Disney Villa with Hot Tub+Grill+Many other amenities
A two-story residential building with a brick driveway, palm trees, and manicured landscaping.

17. Spacious Townhome Near Disney, Free Parking

Spacious Townhome Near Disney, Free Parking
3.5 star property
Regal Palms
8.0 out of 10, Very good, (1 review)
"The unit was clean. The host was responsive. The resort property was fun and welcoming. Definitely enjoyed the pool area. Location was pretty good for all the things we wanted to do. The check-in check-out process was pretty smooth. I would definitely stay here again when I visit this area."
United States
Marquita
The price is €266
includes taxes & fees
16 Nov - 17 Nov
Spacious Townhome Near Disney, Free Parking
A multi-story building with a rooftop terrace, a swimming pool, and a parking lot.

18. Luxury 5BR Family Villa Near Disney

Luxury 5BR Family Villa Near Disney
Champions Gate
9.0 out of 10, Wonderful, (2 reviews)
"Rooms were real clean and the host were great, amazing communication."
United States
Darion W.
Luxury 5BR Family Villa Near Disney
An aerial view of a resort with multiple swimming pools, a dock, and lush greenery.

19. Cozy 3BD Townhouse Near Disney, Encantada Resort

Cozy 3BD Townhouse Near Disney, Encantada Resort
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"I was looking for a place to escape for a few days while getting my bathroom redone and the property checked all of the boxes. My wife was able to get some work done, my dog had more than enough space, and the location is minutes from the amusement parks and tons of restaurants.The property is gated, clean, and has multiple bedrooms and bathrooms for the larger families that need it. The host was more than attentive. Even when I was having issues with the television, he responded to my message...
United States
LEONARD W.
The price is €293
includes taxes & fees
10 Nov - 11 Nov
Cozy 3BD Townhouse Near Disney, Encantada Resort
A two-story house with a red garage, surrounded by a well-maintained lawn and trees.

20. Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney

Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Trafalgar Village
8.8 out of 10, Excellent, (12 reviews)
"House was big enough for the whole family nice pool great area "
United States
Chrystal S.
The price is €412
includes taxes & fees
8 Nov - 9 Nov
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"We were very very pleased with our 2 bedroom suite. Very clean and well maintained suite as it may have been recently updated. The mattresses/beds were terrific! The beds are always a worry when staying somewhere, but we were very happy with the thick mattresses. Also I was so happy to see vinyl flooring and no carpet throughout. We wish we could have stayed longer than just 1 night. We definitely will make this our first choice for our next Orlando trip."
Joy 1-night trip
Posted 2 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Find out more about Winter Haven

Winter Haven Villas information

Number of reviews
257
Accommodation
8572 Villas
Lowest Price
€217
Highest Price
€707

Frequently asked questions

How much do villas in Winter Haven cost?
Villas in Winter Haven cost between €217 and €707 per night. These stays offer the privacy to enjoy your own space at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Winter Haven?
Winter Haven has multiple villas with a total average guest review rating of 9.1. Private Pool 3 Bedroom Home By Redawning is a popular option with Expedia guests. Visitors staying at this 3.5-star getaway will have access to a swimming pool and a lanai. Ov4051 - Southern Dunes - 3 Bed 2. 5 Baths Villa is also a highly recommended stay. This 3.5-star villa comes with a tennis court and a swimming pool, among other conveniences.
How many villas are there in Winter Haven?
Pack your bags and pick from 8572 villas in Winter Haven. For a family holiday, a getaway with friends and everything in between, Expedia will help you find the ideal space in a few easy clicks.
Are there any family-friendly villas in Winter Haven?
Put your feet up at Private Pool 3 Bedroom Home By Redawning, a 3.5-star option just a quick drive from downtown. Conveniences here include WiFi and a pool table. Another family-friendly getaway is Ov4051 - Southern Dunes - 3 Bed 2. 5 Baths Villa. Laundry facilities and an oven help make this 3.5-star retreat a guest favourite. Once you've checked in and unpacked your bags, there's a host of family-friendly attractions to visit around Winter Haven. LEGOLAND® Florida and Indigo's Family Fun Centre are two popular options.
Why book your villa in Winter Haven with Expedia?
Expedia makes it a cinch to find your ideal villa in Winter Haven. Holidaying with the family? Use our handy filters to look for stays with amenities like a pool and WiFi. If you have a budget, click on how much you're willing to spend and the star rating of the property. We'll help you find a perfect place in tune with your style and taste.
How can I find cheap villas in Winter Haven?
The easiest way to get cheap villas in Winter Haven is with Expedia's user-friendly filter tool. Fine-tune your search results by amenities, star rating and budget to land awesome bargains in just a click or two.
What is there to do near my villa in Winter Haven?
Whatever you love doing, Winter Haven has a whole lot to keep you on the move. Indigo's Family Fun Centre, Lake Henry Golf Club and Cypresswood Golf and Country Club are on many visitors' agendas. Don't leave without exploring LEGOLAND® Florida, Chain of Lakes Park and Theatre Winter Haven either. With Expedia's Winter Haven hotel deals, you'll be able to discover even more renowned attractions like these with the money you save.