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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Winter Haven villas

Exterior

Family Vacation Home · 8 Minutes from Legoland Florida

Family Vacation Home · 8 Minutes from Legoland Florida
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"Beautiful clean home. Lots of amenities. However it here were glass decorations on table. We moved them out of reach of 2 and 4 year old. Otherwise BEAUTIFUL! Definitely would stay here again."
United States
Roberta W.
The price is €307
includes taxes & fees
2 Feb - 3 Feb
Family Vacation Home · 8 Minutes from Legoland Florida
Outdoor dining

Enchanted Villa with Lake View 6-Bedroom in Resort 9 miles to Disney World 15 mi

Enchanted Villa with Lake View 6-Bedroom in Resort 9 miles to Disney World 15 mi
Lake Berkley
10.0 out of 10, Exceptional, (2 reviews)
"Me and my girls had a blast staying here the home was incredibly beautiful and slept all of just very comfortably! the host was attentive and replied fast with questions. The gate was a little tricky just because we had multiple cars but overall it was a great place!"
United States
Ireland C.
The price is €390
includes taxes & fees
2 Feb - 3 Feb
Enchanted Villa with Lake View 6-Bedroom in Resort 9 miles to Disney World 15 mi
Exterior

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, (9 reviews)
"House was big enough for the whole family nice pool great area "
United States
Chrystal S.
The price is €400
includes taxes & fees
2 Feb - 3 Feb
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Interior

Lake Berkley Villas Swanky

Lake Berkley Villas Swanky
4.0 star property
Lake Berkley
The price is €274
includes taxes & fees
25 Feb - 26 Feb
Lake Berkley Villas Swanky
Pool

The Sunny | Theme Parks • Heated Pool • Grill

The Sunny | Theme Parks • Heated Pool • Grill
Sandy Ridge
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful group to work with. Enjoyed a much needed vacation. Host was very easy to get in contact with and solved any issues in a timely manner! Plan on staying again sometime in the future!"
United States
Stacy C.
The price is €337
includes taxes & fees
8 Feb - 9 Feb
The Sunny | Theme Parks • Heated Pool • Grill
Villa, 4 Bedrooms | Exterior

Tranquil Hideaway At Sandy Ridge 4 Bedroom Home

Tranquil Hideaway At Sandy Ridge 4 Bedroom Home
3.0 star property
Sandy Ridge
Tranquil Hideaway At Sandy Ridge 4 Bedroom Home
Exterior

Close to Disney - shabby chic style villa with private pool!!

Close to Disney - shabby chic style villa with private pool!!
Lake Berkley
9.4 out of 10, Exceptional, (120 reviews)
"Very good villa; very comfortable beds and in a great location on the 192, close to shops, parks and restaurants."
United Kingdom
Ann Q.
The price is €359
includes taxes & fees
2 Feb - 3 Feb
Close to Disney - shabby chic style villa with private pool!!
Exterior

Fully-Equipped Villa Next to Disney!

Fully-Equipped Villa Next to Disney!
Kissimmee
9.4 out of 10, Exceptional, (76 reviews)
"Perfect for what we needed on our stay "
United States
Kevin H.
The price is €207
includes taxes & fees
16 Feb - 17 Feb
Fully-Equipped Villa Next to Disney!
Exterior

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, (67 reviews)
"Maintenance was phenomenal"
United States
Tirhonda H.
The price is €690
includes taxes & fees
2 Feb - 3 Feb
Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
Outdoor pool, a heated pool, pool loungers

Splendid Lake View Villa With Heated Pool/spa Near Disney

Splendid Lake View Villa With Heated Pool/spa Near Disney
Loughman
9.4 out of 10, Exceptional, (45 reviews)
"Our stay was great. The home is beautiful. Claire was very responsive to our questions. I definitely would stay again. I highly recommend. "
United States
Alfredo V.
The price is €459
includes taxes & fees
6 Feb - 7 Feb
Splendid Lake View Villa With Heated Pool/spa Near Disney
Exterior

Windsor Hills Resort/3Bedrm/Private Pool/Near Disney

Windsor Hills Resort/3Bedrm/Private Pool/Near Disney
Windsor Hills
10.0 out of 10, Exceptional, (22 reviews)
"Loved this place clean and welcoming"
United States
Marlene K.
The price is €421
includes taxes & fees
21 Feb - 22 Feb
Windsor Hills Resort/3Bedrm/Private Pool/Near Disney
Exterior

MAGIC 5* LAKE VIEW VILLA HEATED POOL&HOT SPA, near DISNEY, 10 Guests

MAGIC 5* LAKE VIEW VILLA HEATED POOL&HOT SPA, near DISNEY, 10 Guests
Lake Berkley
8.6 out of 10, Excellent, (32 reviews)
"Thank you. We had a great stay."
United States
Kimberly K.
MAGIC 5* LAKE VIEW VILLA HEATED POOL&HOT SPA, near DISNEY, 10 Guests
Outdoor dining

VedaHive Luxury Villa

VedaHive Luxury Villa
3.0 star property
Solterra Resort
6.6 out of 10, (7 reviews)
"If you enjoy your vacation with a older lady with a daughter telling you what to do and how to act in the house, then this place is for you. The hot tub at the house does not work. There's limited toilet paper so bring your own toiletries. And the bedroom I stayed in did not have sheets on the bed. Must read all the rules before staying at this house. The clubhouse water park is not included in your stay. That is an additional fee$"
United States
James
The price is €151
includes taxes & fees
2 Feb - 3 Feb
VedaHive Luxury Villa
Outdoor pool, a heated pool

Gorgeous VILLA near Disney, Private Heated South Pool

Gorgeous VILLA near Disney, Private Heated South Pool
Sandy Ridge
8.6 out of 10, Excellent, (11 reviews)
"Great place, close to everything, enjoyed the pool, appreciated everything on one floor, the owner checked in on us, which was nice. We would definitely stay here again."
Canada
Bruce P.
The price is €387
includes taxes & fees
6 Feb - 7 Feb
Gorgeous VILLA near Disney, Private Heated South Pool
Exterior

Pool Villa, Game Room, Theater, 20 Minutes to Disney, Great Pool Heat

Pool Villa, Game Room, Theater, 20 Minutes to Disney, Great Pool Heat
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay, Vert responsive Host. Highly recommend. "
United States
Aisha P.
Pool Villa, Game Room, Theater, 20 Minutes to Disney, Great Pool Heat
Villa, 5 Bedrooms | Exterior

Eternal Summer At Solterra Resort 5 Bedroom Villa

Eternal Summer At Solterra Resort 5 Bedroom Villa
3.0 star property
Solterra Resort
The price is €660
includes taxes & fees
8 Feb - 9 Feb
Eternal Summer At Solterra Resort 5 Bedroom Villa
Interior

Magical Disney Getaway- Belle, Potter, & Minions

Magical Disney Getaway- Belle, Potter, & Minions
3.0 star property
Kissimmee
The price is €395
includes taxes & fees
4 Feb - 5 Feb
Magical Disney Getaway- Belle, Potter, & Minions
A heated pool

Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!

Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Kissimmee
8.8 out of 10, Excellent, (86 reviews)
"Great location to parks. House was perfect in accommodating 14 family members with 7 bedrooms. Pool was fantastic and nicely heated. Would stay again."
United States
Janet E.
The price is €752
includes taxes & fees
2 Feb - 3 Feb
Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Villa (3 Bedrooms) | Interior

Upstay Pristine 3BR Home With Private Pool & BBQ

Upstay Pristine 3BR Home With Private Pool & BBQ
3.0 star property
Clermont
The price is €247
includes taxes & fees
3 Feb - 4 Feb
Upstay Pristine 3BR Home With Private Pool & BBQ
Exterior

Family Retreat @ Resort with Private Pool, 6Bdrm

Family Retreat @ Resort with Private Pool, 6Bdrm
Solterra Resort
9.2 out of 10, Wonderful, (19 reviews)
"The e house was amazing, it was clean, check in process was flawless. I have no complaints, the subdivision was great and a water park. Would stay here again. "
United States
Darrel S.
Family Retreat @ Resort with Private Pool, 6Bdrm
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 & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent
"Clean room, liked the balcony. Breakfast was 10/10 lots of options. My family and I also enjoyed the amenities. Overall great stay. There’s a resort fee at the hotel so be mindful about that when checking in."
Lina 2-night trip
Posted 2 days ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Find out more about Winter Haven

Winter Haven Villas information

Number of reviews
487
Accommodation
8785 Villas
Lowest Price
€151
Highest Price
€752

Frequently asked questions

How much do villas in Winter Haven cost?
Villas in Winter Haven cost between €151 and €752 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 8785 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.