Best Winter Haven Villas: Private & Luxury Villa Accommodations in Winter Haven

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

1. Your Disney Dream Stay 5BR Villa + Private Pool

Marbella

Bryan l.

includes taxes & fees

19 Oct - 20 Oct

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

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

Kissimmee

Cordell G.

includes taxes & fees

12 Oct - 13 Oct

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

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

Davenport

Jalisa Y.

includes taxes & fees

8 Oct - 9 Oct

An outdoor lounge area with multiple seating options, ceiling fans, and large windows offering views of palm trees and a beach.

4. Upstay Modern Solara Retreat w Games Room & Pool

Kissimmee

includes taxes & fees

18 Oct - 19 Oct

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

5. Amazing Villa with south facing pool and conservation view

Watersong

David V.

A balcony with two blue cushioned chairs, a glass door leading to a bedroom, and a view of a grassy area and buildings in the distance.

6. Stylish 3BR Condo Championsgate w Water Park

Davenport

includes taxes & fees

8 Oct - 9 Oct

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

Sandy Ridge

includes taxes & fees

26 Oct - 27 Oct

Al fresco dining meets resort-style privacy in this beautifully landscaped outdoor living space

8. LuxuryResort~MagicVillage~Ensuite Baths~NearDisney

Kissimmee

includes taxes & fees

12 Oct - 13 Oct

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Top Winter Haven Hotel Reviews

Kompose Boutique Resort at Theme Parks

10/10 Excellent

"Hotel was clean staff was friendly and even though the main pool was closed for maintenance, it was a nice gesture to wave the daily parking fee for guest for the time being."

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"The space was excellent. Excellent value for what I paid for my family to stay in a two bedroom villa. I love the size of the entire property and especially loved how peaceful environment and the privacy that our villa provided. River Island was awesome, my entire family loved every bit of it. For a three night getaway I didn’t get to do all that this property has to offer, but I was perfectly fine with what we did enjoy doing. I must say, however, that being a first time renter at this property, I foolishly agreed to their “tour of the property“ that they offer you. After you complete the tour you would receive a $200 gift card to use on the property. I knew that this was an old school timeshare proposition, but they swore that they wouldn’t give you the hard sell at the end of the tour, and I foolishly believed it. Needless to say that what was supposed to be a 90 minute tour turned into 2 1/2 hours of wasted time and they just wouldn’t take no for an answer at least for a good 20 or 30 minutes or so. Then finally they gave in and I got myself the gift card. Now, if it wasn’t that, it was a rainy day to begin with, I perhaps would’ve been more upset at the experience. But since we were basically going to be rained in for most of that day, I just rolled with it as best as I could. Otherwise, I absolutely loved my time there, and I would absolutely look into renting there again in the future. I’ll just make sure to avoid their “tour of the property“… Never again."

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"Excellent stay, since the arrival with the check in at the front desk with Noemi, the sweetest and more knowledgeable person ever, to the customer assistance with the living room TV issue, they are all fantastic. Rooms are newly renovated, the property is well maintained and have a lot of activities for all ages, all the time."

LEGOLAND Beach Retreat

8/10 Good

"We were able to get an early check in and that was fantastic! My kids loved the room and the legos that were available for play. The room did smell very musty and there was a cockroach in the room, but that’s typical for Florida. The breakfast was delicious! We never used the shuttle because the hotel parking pass was accepted at the park so we decided to take our own vehicle back and forth. All in all, it was a good stay for what we needed!"

Find out more about Winter Haven

Winter Haven Villas information

Number of reviews	331
Accommodation	8421 Villas
Lowest Price	AU$387
Highest Price	AU$1,164

Frequently asked questions

How much do villas in Winter Haven cost?

Expect to pay between AU$387 and AU$1,164 per night for a villa in Winter Haven. No matter your budget, an epic stay is only a few clicks away on Expedia. This price was 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.

How many villas are there in Winter Haven?

Pack your bags and choose from 8421 villas in Winter Haven. For a family holiday, a couple's getaway and everything in between, Expedia can help you find the ideal place in just a click or two.

What is there to do near my villa in Winter Haven?

Winter Haven has enough experiences to keep you occupied for weeks, starting with LEGOLAND® Florida. Theatre Winter Haven, Indigos Billiards, Bowling & Games and Chain of Lakes Park are other well-known attractions. If you're lingering longer, The Circle B Bar Reserve and Auburndale City Park are great additions to your itinerary.

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Search Winter Haven Villa Accommodation

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Haven villas

1. Your Disney Dream Stay 5BR Villa + Private Pool

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

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

4. Upstay Modern Solara Retreat w Games Room & Pool

5. Amazing Villa with south facing pool and conservation view

6. Stylish 3BR Condo Championsgate w Water Park

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

8. LuxuryResort~MagicVillage~Ensuite Baths~NearDisney

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

10. Gorgeous VILLA near Disney, Private Heated South Pool

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

12. Magical 5-Bedroom Villa Near Universal's Wizarding

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

14. Spacious Townhome Near Disney, Free Parking

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

16. Family Villa w Lazy River Near Disney

17. The ideal getaway II

18. Sunkissed Paradise | Private Pool & Hot Tub

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

20. 8761 ZD - 3 BD The Hub Paradise Cozy Place

Find holiday rentals that suit your style

Top Winter Haven Hotel Reviews

Kompose Boutique Resort at Theme Parks

Find out more about Winter Haven

Winter Haven Villas information

Frequently asked questions

Explore a world of travel with Expedia