Winter Haven Villas

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

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Our top choices for Winter Haven villas

A swimming pool with clear water, surrounded by palm trees and a glass enclosure.

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

Haines City

dan l.

HK$3,142 total

includes taxes & fees

25 Oct - 26 Oct

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

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

Kissimmee

Joel W.

HK$1,992 total

includes taxes & fees

18 Nov - 19 Nov

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

Kissimmee

Cordell G.

HK$2,586 total

includes taxes & fees

24 Oct - 25 Oct

A two-story house with a garage, stone accents, and a well-maintained lawn.

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

Davenport

Angel M.

HK$6,473 total

includes taxes & fees

24 Oct - 25 Oct

A two-story residential building with a brick driveway, palm trees, and manicured landscaping.

5. Spacious Townhome Near Disney, Free Parking

Regal Palms

Marquita

HK$2,344 total

includes taxes & fees

25 Oct - 26 Oct

A covered outdoor swimming pool with lounge chairs and a pergola structure.

6. Gorgeous VILLA near Disney, Private Heated South Pool

Sandy Ridge

Janay P.

HK$3,345 total

includes taxes & fees

25 Oct - 26 Oct

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

Sandy Ridge

HK$3,009 total

includes taxes & fees

25 Oct - 26 Oct

A two-story building with a symmetrical facade, a central entrance with a door, and a small porch area.

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

Regal Palms

HK$4,716 total

includes taxes & fees

14 Nov - 15 Nov

9. Emerald Garden - Resort - 15 Min to Disney - Pets

Kissimmee

HK$3,227 total

includes taxes & fees

26 Oct - 27 Oct

A balcony with two beds, a door, and a view of a green landscape.

10. LuxuryResort~MagicVillage~Ensuite Baths~NearDisney

Kissimmee

HK$3,925 total

includes taxes & fees

4 Nov - 5 Nov

A two-story house with a red garage, surrounded by a well-maintained lawn and trees.

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

Trafalgar Village

Chrystal S.

HK$3,700 total

includes taxes & fees

25 Oct - 26 Oct

A multi-story building with a rooftop terrace, a swimming pool, and a parking lot.

12. Luxury 5BR Family Villa Near Disney

Champions Gate

Darion W.

HK$3,529 total

includes taxes & fees

15 Nov - 16 Nov

A modern townhouse with a flat roof, large windows, and a small patio area with outdoor seating.

13. 8761 ZD - 3 BD The Hub Paradise Cozy Place

Four Corners

HK$3,651 total

includes taxes & fees

2 Nov - 3 Nov

A single-story house with a front porch, a dark front door, and a small front yard with palm trees and shrubs.

14. Sunkissed Paradise | Private Pool & Hot Tub

Trafalgar Village

"Overall the villa was lovely, beautifully clean inside with nice touches like mini toiletries, large tub of ground coffee, sugar, creamer, plenty of toilet rolls salt and pepper, olive oil, coffee filters oh and a kettle bonus for us Brits.The Lounge, dining and bedrooms were beautifully furnished and had everything we needed. Plenty of bath towels, although could have done with a few more pool towels so we didn’t have to put them in the dryer after each use, but a minor detail.Frank was an...

Sarah B.

HK$3,114 total

includes taxes & fees

25 Oct - 26 Oct

A covered outdoor seating area with sofas and chairs, large windows, and a ceiling fan.

15. Solara Resort Home With Private Pool Near Disney

Kissimmee

HK$2,508 total

includes taxes & fees

25 Oct - 26 Oct

An aerial view of a resort with multiple swimming pools, a dock, and lush greenery.

16. Cozy 3BD Townhouse Near Disney, Encantada Resort

Kissimmee

"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...

LEONARD W.

HK$2,704 total

includes taxes & fees

1 Nov - 2 Nov

A residential area with houses featuring sloped roofs and a central garage.

17. Family Retreat @ Resort with Private Pool, 6Bdrm

Solterra Resort

Ken B.

HK$3,339 total

includes taxes & fees

26 Oct - 27 Oct

A residential house with a garage, a front yard with grass and a tree, and a clear sky.

18. 12 min drive to Disney, Luxury Designer 4BD Villa with heated pool& Spa

Loma Linda

HK$4,190 total

includes taxes & fees

25 Oct - 26 Oct

19. 🌿Welcome to the Jungle🌿

Loughman

Amanda P.

HK$3,643 total

includes taxes & fees

26 Oct - 27 Oct

A resort with a swimming pool, beach area, and a pier extending into a lake.

20. Bahama Bay Resort * Disney Area * Free Parking

Bahama Bay

HK$2,522 total

includes taxes & fees

24 Oct - 25 Oct

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Top Winter Haven Hotel Reviews

Vacation Village Orlando, Celebration

10/10 Excellent

"Todo estuvo perfecto las anotaciones"

Best Western Plus Winter Haven Inn & Suites

10/10 Excellent

"My family and I enjoyed our stay here. The guy that checked us in was very helpful and accommodating. The hotel itself and the room was very clean as well. There were a few breakfast items to choose from which we enjoyed. The only thing was that they had a better selection on Saturday than Sunday so I didn’t really eat anything. There was also a bit of a line waiting for the elevator because only one was in use. Other than that, we enjoyed ourselves especially it being less than 5 minutes from Legoland."

Legoland Florida Hotel

8/10 Good

"Proximity to Legoland can't be beat - very convenient. Disappointed with check in - we were given a key card with a QR code on the back and were told that everything we need to know is on there. Couldn't find wifi password. Didn't find out about complimentary breakfast until our last day. Breakfast was surprisingly good and all you can eat (didn't care for the grits). QR code essentially takes you to Legoland webpage."

Find out more about Winter Haven

Winter Haven Villas information

Number of reviews	291
Accommodation	8572 Villas
Lowest Price	HK$1,992
Highest Price	HK$6,473

Frequently asked questions

How much do villas in Winter Haven cost?

Villas in Winter Haven cost between HK$1,992 and HK$6,473 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 8.9. 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.

Search Villas in Winter Haven

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Haven villas

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

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

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

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

5. Spacious Townhome Near Disney, Free Parking

6. Gorgeous VILLA near Disney, Private Heated South Pool

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

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

9. Emerald Garden - Resort - 15 Min to Disney - Pets

10. LuxuryResort~MagicVillage~Ensuite Baths~NearDisney

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

12. Luxury 5BR Family Villa Near Disney

13. 8761 ZD - 3 BD The Hub Paradise Cozy Place

14. Sunkissed Paradise | Private Pool & Hot Tub

15. Solara Resort Home With Private Pool Near Disney

16. Cozy 3BD Townhouse Near Disney, Encantada Resort

17. Family Retreat @ Resort with Private Pool, 6Bdrm

18. 12 min drive to Disney, Luxury Designer 4BD Villa with heated pool& Spa

19. 🌿Welcome to the Jungle🌿

20. Bahama Bay Resort * Disney Area * Free Parking

Find holiday rentals that suit your style

Top Winter Haven Hotel Reviews

Vacation Village Orlando, Celebration

Find out more about Winter Haven

Winter Haven Villas information

Frequently asked questions

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