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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Villas in Winter Haven and around

Amazing Reunion Resort Vacation Villa With Pool
Fridge, microwave, oven, stovetop

Amazing Reunion Resort Vacation Villa With Pool

8.8 out of 10, Excellent, (38)
"Excellent stay, easy drive to all the parks"
Amazing Reunion Resort Vacation Villa With Pool
Spacious 7-bedroom villa with Resort-style near Disney World
Smart TV

Spacious 7-bedroom villa with Resort-style near Disney World

6.0 out of 10, (1)
Spacious 7-bedroom villa with Resort-style near Disney World
A 6 Bedroom Home at Solterra Resort with Pool & Spa with a Nice Lake View!
Outdoor pool, a heated pool

A 6 Bedroom Home at Solterra Resort with Pool & Spa with a Nice Lake View!

9.4 out of 10, Exceptional, (94)
"We enjoyed our stay with all the family together. The kids enjoyed the pool to the fullest!!"
A 6 Bedroom Home at Solterra Resort with Pool & Spa with a Nice Lake View!
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"
South Facing Pool and Spa - Resort Amenities
Reunion BRAND NEW Fancy Vacation Home
5 bedrooms, iron/ironing board, travel cot, free WiFi

Reunion BRAND NEW Fancy Vacation Home

9.4 out of 10, Exceptional, (18)
"Spacious property with excellent facilities, perfect as a base for our Disney holiday "
Reunion BRAND NEW Fancy Vacation Home
West Facing Pool and Spa
Pool

West Facing Pool and Spa

9.0 out of 10, Wonderful, (76)
"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
Princess, Pirate & Super Hero Rooms, Mickey Pool, Toys & Game Room For All Ages
Outdoor pool, a heated pool

Princess, Pirate & Super Hero Rooms, Mickey Pool, Toys & Game Room For All Ages

9.8 out of 10, Exceptional, (176)
"Property accommodated our family of 10 nicely with plenty of seating in living room for all members to watch TV (NBA finals were on) and pool patio area where everyone could seat and enjoy morning coffee together and talk. Disney was about a 10 minute drive; however, traffic was a nightmare at times."
Princess, Pirate & Super Hero Rooms, Mickey Pool, Toys & Game Room For All Ages
Swim Up Pool Bar, Movie Theater - 2 miles to Disney World
Exterior

Swim Up Pool Bar, Movie Theater - 2 miles to Disney World

10.0 out of 10, Exceptional, (105)
"Excellent stay and amenities. Pool was great! "
Swim Up Pool Bar, Movie Theater - 2 miles to Disney World
DREAM VILLA 6BD / ALL EN-SUITE - Theatre*Pool*Spa
A heated pool

DREAM VILLA 6BD / ALL EN-SUITE - Theatre*Pool*Spa

9.4 out of 10, Exceptional, (21)
"The Home was perfect for us. "
DREAM VILLA 6BD / ALL EN-SUITE - Theatre*Pool*Spa
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Smart TV, DVD player, table football, books

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

9.6 out of 10, Exceptional, (125)
"This was a great place to stay close to Disney in a quiet location . "
The price is €396
includes taxes & fees
24 Aug - 25 Aug
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Villa with Private Pool, Games Room, Free Wifi and Lake View
Smart TV

Villa with Private Pool, Games Room, Free Wifi and Lake View

9.8 out of 10, Exceptional, (67)
"Great place "
Villa with Private Pool, Games Room, Free Wifi and Lake View
8BR, 4.5 BA, Pool, Sleeps 16
Fridge, microwave, oven, stovetop

8BR, 4.5 BA, Pool, Sleeps 16

9.6 out of 10, Exceptional, (101)
"Everytime we stay in a rental home for this particular host, we always have a great stay. Always exceeds expectations! "
8BR, 4.5 BA, Pool, Sleeps 16
Luxurious 9BR Retreat | Pool, Games, & More
Pool

Luxurious 9BR Retreat | Pool, Games, & More

9.0 out of 10, Wonderful, (2)
"House was nice and roomy but the back gate doors both had broken latches but there was enough security patroling the area so i wasn't bothered by it."
Luxurious 9BR Retreat | Pool, Games, & More
BRAND NEW Mickey's Mansion @ Windsor Island Resort- Near Disney - Free Waterpark
A heated pool

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

10.0 out of 10, Exceptional, (38)
"The stay at Mickey’s Mansion was perfect. The house was maticulaous and modern. Owners were communicative, friendly and helpful. Looking forward to booking again next year!"
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, (154)
"The house was great, a lot of the beds are squeaky. "
Luxury 8 Bedroom Villa, Good for 18 to 20, Pool/Spa
Windsor 10BD Disney Villa for large group! Pool/SPA/Game/BBQ/5 Kings/30 sleeps!
Property grounds

Windsor 10BD Disney Villa for large group! Pool/SPA/Game/BBQ/5 Kings/30 sleeps!

9.4 out of 10, Exceptional, (46)
"Exceptional place to stay."
Windsor 10BD Disney Villa for large group! Pool/SPA/Game/BBQ/5 Kings/30 sleeps!
Sandyridge Disney/Universal/Seaworld/Golf 4bed/3bath Villa Pool Heat Included
Outdoor pool, a heated pool

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

9.6 out of 10, Exceptional, (109)
"Property was amazing. Close to Disney parks. "
Sandyridge Disney/Universal/Seaworld/Golf 4bed/3bath Villa Pool Heat Included
PRIVATE VILLA WITH SECURITY GATE, ON SUNSET LAKES-KISSIMMEE. 10MIN TO DISNEY :)
Property grounds

PRIVATE VILLA WITH SECURITY GATE, ON SUNSET LAKES-KISSIMMEE. 10MIN TO DISNEY :)

9.8 out of 10, Exceptional, (126)
"Absolutely loved our stay here! The house was clean and had plenty of space. Pool was nice and relaxing. Location is very convinient to the parks. I would stay here again the next time we are in the area! "
PRIVATE VILLA WITH SECURITY GATE, ON SUNSET LAKES-KISSIMMEE. 10MIN TO DISNEY :)
South Facing Pool and Spa!
Children’s area

South Facing Pool and Spa!

8.0 out of 10, Very good, (18)
"We love it. "
South Facing Pool and Spa!
Our DisneyDreamVilla - Only minutes to DisneyWorld!!!
Outdoor pool, a heated pool

Our DisneyDreamVilla - Only minutes to DisneyWorld!!!

10.0 out of 10, Exceptional, (241)
"The home is beautiful and in the perfect location to visit all the Disney parks & Universal !"
Our DisneyDreamVilla - Only minutes to DisneyWorld!!!
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 Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent
"Its nice "
Mark 3-night trip
Posted 19 hours ago
Holiday Inn Resort Kissimmee by the Parks by IHG

Frequently asked questions

How much do villas in Winter Haven cost?
Villas in Winter Haven cost between €396 and €396 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 8652 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.