Search Villas in Winter Haven

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sep - 21 Sep

Villas in Winter Haven

Amazing Reunion Resort Vacation Villa With Pool
Exterior

Amazing Reunion Resort Vacation Villa With Pool

9.0 out of 10, Wonderful, (37)
"Great home for a family! Plenty of space and a wonderful game room! Every room has its own bathroom which is great when you have multiple people needing to shower after a day at the park. The master bathroom has dual showers, which is great! Be cautious of the right shower door, it’s not aligned correctly, so if you close it to hard it could shatter. Otherwise wonderful place to be! "
Amazing Reunion Resort Vacation Villa With Pool
🌟 Spacious 4BR Getaway 🏡 Pool, Privacy & Near Parks 🎢
Exterior

🌟 Spacious 4BR Getaway 🏡 Pool, Privacy & Near Parks 🎢

10.0 out of 10, Exceptional, (5)
🌟 Spacious 4BR Getaway 🏡 Pool, Privacy & Near Parks 🎢
Hampton Lakes - Contemporary 4 bedrooms home with game room
Exterior

Hampton Lakes - Contemporary 4 bedrooms home with game room

9.4 out of 10, Exceptional, (14)
"We enjoyed our stay the house was great we loved the pool was clean and I paid extra for it to be heated..would go back to this house to stay .was close to stores too . Thanks for letting us have this home ."
Hampton Lakes - Contemporary 4 bedrooms home with game room
Luxury 12 Bed / 14 Bath Villa in Reunion Resort
Exterior

Luxury 12 Bed / 14 Bath Villa in Reunion Resort

9.6 out of 10, Exceptional, (85)
"Great location. House had many small repairs needed. Refrigerator, coffee pot, food stuck on curtain to pool, shower in one room broken knob and didn’t work. "
Luxury 12 Bed / 14 Bath Villa in Reunion Resort
Luxury Villa Close to Disney 5br Private Pool
A heated pool

Luxury Villa Close to Disney 5br Private Pool

9.8 out of 10, Exceptional, (59)
"Everything was great!! We very much enjoyed our stay! "
Luxury Villa Close to Disney 5br Private Pool
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192
Exterior

4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

10.0 out of 10, Exceptional, (296)
"."
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192
8 bdrms! Theatre! Game Room-4 Xboxes! Harry Potter, Toy Story, & Up Bedrooms!
Exterior

8 bdrms! Theatre! Game Room-4 Xboxes! Harry Potter, Toy Story, & Up Bedrooms!

10.0 out of 10, Exceptional, (24)
"We enjoyed our stay. It was very comfortable and nice. "
8 bdrms! Theatre! Game Room-4 Xboxes! Harry Potter, Toy Story, & Up Bedrooms!
West Facing Pool and Spa
Pool

West Facing Pool and Spa

9.0 out of 10, Wonderful, (74)
"The house was as advertised. It was spacious and comfortable and made for a great and relaxing vacation. Would definitely stay here again. "
West Facing Pool and Spa
3 MILES FROM DISNEY!! Private SOUTH facing Pool. Awesome family villa
Exterior

3 MILES FROM DISNEY!! Private SOUTH facing Pool. Awesome family villa

9.6 out of 10, Exceptional, (218)
"Great "
3 MILES FROM DISNEY!! Private SOUTH facing Pool. Awesome family villa
South Facing Pool and Spa - Resort Amenities
Pool

South Facing Pool and Spa - Resort Amenities

7.6 out of 10, Good, (19)
"Lets go positive first Listing was mostly as advertised"
The price is SAR 1,284
SAR 2,075 total
includes taxes & fees
29 Jul - 30 Jul
South Facing Pool and Spa - Resort Amenities
Windsor Hills! Free Pool Heat/BBQ/Waterpark. Game Room w/Theater, Themed Rooms.
A heated pool

Windsor Hills! Free Pool Heat/BBQ/Waterpark. Game Room w/Theater, Themed Rooms.

10.0 out of 10, Exceptional, (64)
"House was great, plenty of room for the 10 of us. Kids loved the pool, swam all day. Appliances all worked well, everything was as described. The amenities at the club house were also fantastic, nice pools, splash pad, slides. Restaurant had decent food and specialty coffees as well."
Windsor Hills! Free Pool Heat/BBQ/Waterpark. Game Room w/Theater, Themed Rooms.
MARCH SPECIAL AVAILABLE!
Exterior

MARCH SPECIAL AVAILABLE!

9.0 out of 10, Wonderful, (77)
"Lovely stay, Nicole was very communicative and accommodating. The location was very quiet and relaxing."
MARCH SPECIAL AVAILABLE!
New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Terrace/patio

New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~

9.6 out of 10, Exceptional, (5)
"The communication with Andy was good. The dishes were dirty and needed to be washed before we used them. The floors were not very clean either. The pool heater was not properly but got repaired in a few days. "
New Opening! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
A heated pool

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

9.6 out of 10, Exceptional, (125)
"Excellent location, clean and spacious! Will definitely stay again!"
The price is SAR 619
SAR 1,695 total
includes taxes & fees
24 Aug - 25 Aug
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Westridge Luxury Family Villa near Disney and other Theme parks.
Exterior

Westridge Luxury Family Villa near Disney and other Theme parks.

9.8 out of 10, Exceptional, (141)
"This is our second time at the Villa. Same as the first one, our stay rates up there at the top. Accommodations are first rate, situation is very good, comfort inside and out is outstanding. But most of all, the owner is the best. Always present, reachable and provides an immediate response to our needs, Indeed a five star rating."
Westridge Luxury Family Villa near Disney and other Theme parks.
Glenbrook Retreat-Come in as Guests and Leave as Friends
Exterior

Glenbrook Retreat-Come in as Guests and Leave as Friends

9.6 out of 10, Exceptional, (194)
"This was a perfect little stay for us! Love the pool and great location! "
Glenbrook Retreat-Come in as Guests and Leave as Friends
Luxurious 9BR Retreat | Pool, Games, & More
Pool

Luxurious 9BR Retreat | Pool, Games, & More

10.0 out of 10, Exceptional, (1)
"First off, the space, layout and amenities were perfect for our large family. We were pleased with the ease of check-in, the cleanliness and the amenities were great. We did have concerns that there was only seating at the dining table for 2 when the condo slept 20. We notified the agent was told he would address it. We stayed 3 nights and didn’t see anyone. Hopefully it has been fixed since our departure. "
Luxurious 9BR Retreat | Pool, Games, & More
BRAND NEW Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
Exterior

BRAND NEW Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark

10.0 out of 10, Exceptional, (36)
"We had a perfect stay. This was a great location for accessing all there is to do! Minutes from Disney and Universal. The house was very clean and nicely set up with just about everything you would ever need. The pool and hot tub were a hit after a long day of running around. The host was very quick in replying to any questions we had. Would definitely stay here again! "
BRAND NEW Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
Luxury 8 Bedroom Villa, Good for 18 to 20, Pool/Spa
A heated pool

Luxury 8 Bedroom Villa, Good for 18 to 20, Pool/Spa

8.6 out of 10, Excellent, (153)
"The house was great, a lot of the beds are squeaky. "
Luxury 8 Bedroom Villa, Good for 18 to 20, Pool/Spa
Sandyridge Disney/Universal/Golf 4bed/3bath Villa Pool Heat Included
Exterior

Sandyridge Disney/Universal/Golf 4bed/3bath Villa Pool Heat Included

9.6 out of 10, Exceptional, (109)
"Property was amazing. Close to Disney parks. "
Sandyridge Disney/Universal/Golf 4bed/3bath Villa Pool Heat Included
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

10/10 Excellent
"Loved the customer service, the property, and accessibility. The only down side was not having a broom, mop, or other cleaning supplies."
Lacie Ann 6-night trip
Posted 14 hours ago
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

Frequently asked questions

How much do villas in Winter Haven cost?
Villas in Winter Haven cost between SAR 619 and SAR 1,314 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 8675 villas in Winter Haven. For a family vacation, a getaway with friends and everything in between, Expedia will help you find the ideal space in a few easy clicks.