Winter Haven Villas - Best Villa Winter Haven 2026

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

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Our top choices for Winter Haven villas

A residential house with a tiled roof, a palm tree, and a car parked in the driveway.

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

Kissimmee

Cordell G.

includes taxes & fees

23 Sept - 24 Sept

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

Haines City

dan l.

includes taxes & fees

23 Sept - 24 Sept

A residential neighborhood with houses, a driveway, and a parked car.

3. 5BR Family Villa | Private Pool | Near Disney

Marbella

Bryan l.

A hotel entrance with a central fountain, palm trees, and a clear blue sky.

4. Amazing Villa with south facing pool and conservation view

Watersong

David V.

includes taxes & fees

23 Sept - 24 Sept

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

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

Davenport

Jalisa Y.

includes taxes & fees

1 Oct - 2 Oct

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

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

Solterra Resort

Ken B.

includes taxes & fees

23 Sept - 24 Sept

A residential area with houses featuring red-tiled roofs and well-maintained lawns.

7. Family Vacation @ Resort with Private Pool, 6Bdrm

Solterra Resort

Kenny G.

includes taxes & fees

23 Sept - 24 Sept

An aerial view of a resort with a large swimming pool, multiple lounge areas, and a winding water feature.

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

Kissimmee

Heather

includes taxes & fees

23 Sept - 24 Sept

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

9. Gorgeous VILLA near Disney, Private Heated South Pool

Sandy Ridge

Janay P.

10. 🌿Welcome to the Jungle🌿

Loughman

Amanda P.

A two-story building with a beige facade, black-framed windows, and a brick entrance.

11. Full Arcade~Resort~Heated Pool~Anime Adventure!

Kissimmee

"This property is truly stunning and well thought out. It has everything you will need to feel like you are home from home. The resort is good and has a great location for Disney. This property will easily accommodate large families inside with plenty of parking outside too. The hosts are great and very fast to respond to any messages. A great place to lay your roots in the Orlando area. Highly recommended! "

Adele L.

includes taxes & fees

23 Sept - 24 Sept

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

12. Spacious Townhome Near Disney, Free Parking

Regal Palms

Marquita

includes taxes & fees

27 Sept - 28 Sept

13. 1067 3BR Luxury Resort House by Disney Orlando

Festival

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

14. Luxury 5BR Family Villa Near Disney

Champions Gate

Darion W.

includes taxes & fees

27 Sept - 28 Sept

A two-story house with a garage, a red door, and a well-maintained lawn.

15. Disney 5BR ChampionsGate Villa, Private Pool, Game Room, Sleeps 14

Champions Gate

Jennifer W.

An aerial view of a lakeside resort with a swimming pool, a castle-like structure, and surrounding residential areas.

16. Beach Resort near Disney with Poolside Tike Bar

Bahama Bay

Jerome S.

includes taxes & fees

23 Sept - 24 Sept

A pool area with a hot tub, lounge chairs, and a view of a residential neighborhood.

17. Splendid Lake View Villa With Heated Pool/spa Near Disney

Loughman

annette h.

includes taxes & fees

23 Sept - 24 Sept

A large, multi-story hotel with a central courtyard, surrounded by lush greenery and palm trees.

18. VRBO 5 Star Luxury Resort Villa close to Disney World with poolside bar

Reunion

Everick

includes taxes & fees

23 Sept - 24 Sept

A covered outdoor area with a swimming pool, a table with a bowl of fruit, and chairs.

19. The Sunny | Theme Parks • Heated Pool • Grill

Sandy Ridge

Stacy C.

A spacious outdoor area with a pool, wicker furniture, and a view of a residential neighborhood during sunset.

20. Enchanted Villa with Lake View 6-Bedroom in Resort

Lake Berkley

Sarah J.

includes taxes & fees

23 Sept - 24 Sept

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Top Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

10/10 Excellent

"Absolutely great stay. The grounds were well kept, the staff was so friendly and accommodating especially TaTa who maintained great service in the rain!! We had a great time and definitely will be back!!"

Hilton Vacation Club Aqua Sol Orlando West

8/10 Good

"We had a very good stay at Hilton Aquasol. The property was beautiful, the accommodations were comfortable, and overall everything about the resort was excellent. The only part of the experience I did not like was the pressure to attend a timeshare presentation. We did not attend the presentation, but guests are required to stop at the timeshare desk in order to obtain a parking permit, so it is very difficult to avoid the sales approach. We felt there was too much pressure to attend the presentation offering you gifts and free stays, even after making it clear that we were not interested. I think guests should be able to obtain their parking permit directly from the front desk without having to go through a timeshare sales conversation. Aside from that, we really enjoyed our stay and had a great experience at the resort."

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent

"The AC went out in the building we were supposed to be in. They called before we arrived and offered to upgrade us to a cottage. Above and beyond our expectations. We had a late arrival of 3 am due to flight delays and they had someone waiting with a golf cart to take us to the cottage. Restaurant was excellent. Waterpark was super close and the kids had a blast. Pool at the resort was beautiful as well. Already looking to book again!"

Find out more about Winter Haven

Winter Haven Villas information

Number of reviews	598
Accommodation	8377 Villas
Lowest Price	€263
Highest Price	€727

Frequently asked questions

How much do villas in Winter Haven cost?

Villas in Winter Haven cost between €263 and €727 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 9.3. 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 8377 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Haven villas

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

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

3. 5BR Family Villa | Private Pool | Near Disney

4. Amazing Villa with south facing pool and conservation view

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

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

7. Family Vacation @ Resort with Private Pool, 6Bdrm

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