Villas in Winter Haven

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Compare 7305 Villas in Winter Haven with updated reviews, rates, and availability.

4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192
10.0 out of 10, Exceptional, (241)
"This could not have been a better place to stay."
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192
Come stay at your perfect Oasis at Champions Gate Resort.
9.6 out of 10, Exceptional, (32)
"very nice property, great communication, host very nice to speak with, would highly recommend!"
Come stay at your perfect Oasis at Champions Gate Resort.
DISNEY 2 MILES LUXURY FAMILY VILLA for 16 - 10 TVs 75, 7@65 PRVT POOL + JACUZZI
10.0 out of 10, Exceptional, (181)
"This home was great for multiple families. The house lay out gave each family a place of their own. The pool area has so much room! Highly recommend this house."
DISNEY 2 MILES LUXURY FAMILY VILLA for 16 - 10 TVs 75, 7@65 PRVT POOL + JACUZZI
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Luxury Orlando Villa with PrivateTheater at pool area
9.8 out of 10, Exceptional, (15)
"This was such an amazing property for our family. Great location for my family to enjoy the parks and an excellent pool and game room to unwind with after a long day. Communication with the property management was speedy and super helpful. I wish we could have stayed longer and will definitely be a location at the top of our list to visit again when we are in the area! Thanks again for a great stay!"
Luxury Orlando Villa with PrivateTheater at pool area
Spacious 6 bedroom home with private pool Gated community Lake Berkley Resort
10.0 out of 10, Exceptional, (10)
"There is not one negative thing I could say about this property. We were in Florida for my daughter’s cheer comp and her brothers had to tag along. The house provides perfect space for everyone to be comfortable, the pool was great entertainment for everyone. The location was fantastic. The host was so kind and helpful!"
Spacious 6 bedroom home with private pool Gated community Lake Berkley Resort
The Peninsula - Villa with Pool Conservation Area View
9.4 out of 10, Exceptional, (141)
"Upon check in we were pleasantly surprised based on some of the harsh reviews we had seen. A very nice big space for us to relax in and the villa was situated in a quiet and secure community. A nice little welcome pack provided us with some cleaning products and the house was fully stocked with fresh towels for use which was a bonus. Beds were very comfortable and the air con was welcomed greatly. The pool was bigger than we anticipated from the pictures, very clean and had its chemical levels...
The Peninsula - Villa with Pool Conservation Area View
280CW-🥇Gorgeous 9 bed/ 8 bath-Private Pool & SPA
9.8 out of 10, Exceptional, (11)
"We arrived about 10 minutes before the 4pm check in time and were denied access which was something we’ve never experienced. We had to call security each time we arrived at the property because we didn’t receive a QR code for the gate. Overall, the property is immaculate and had everything that you could think of to have an enjoyable stay. We wouldn’t definitely stay here in the future."
280CW-🥇Gorgeous 9 bed/ 8 bath-Private Pool & SPA
🥇Gorgeous Disney Home - Resort Free Access with Lazy River
9.4 out of 10, Exceptional, (40)
"Good"
🥇Gorgeous Disney Home - Resort Free Access with Lazy River
JUST REMODELED!! 3BR/2BR Chic Villa Near Disney UNIT A
9.6 out of 10, Exceptional, (84)
"The house is very clean an organized...laundry is a plus...really quite Condo and close to everything. We went to Medieval Dinner Time, just 4 min from the house, really nice experience, and another day just at the pool. Planning to comeback soon!!! Catalina is very friendly and just a text away from you."
JUST REMODELED!! 3BR/2BR Chic Villa Near Disney UNIT A
☀️🌴Award-Winning Golf, Disney/Universal, Pool, Clubhouse/Gated Community 🌴☀️
10.0 out of 10, Exceptional, (62)
"We had the most amazing stay in this beautiful villa. The property is an absolute delight and has everything you need for a wonderful stay. Our trip to Orlando this year was to relax by the pool and the guys to go golfing (we have done the parks a couple of times), and we could not have asked for anything more! Kazan was the most wonderful host, who helped us move to this villa from the original we had booked into, that did not have a functioning pool. Kazan could not do enough for us in a very...
☀️🌴Award-Winning Golf, Disney/Universal, Pool, Clubhouse/Gated Community 🌴☀️
Cozy 12BR Pool House/BBQ/Sleep 24/Near Disney
Cozy 12BR Pool House/BBQ/Sleep 24/Near Disney
Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View
8.6 out of 10, Excellent, (70)
"Very nice home with enclosed pool on the lake. We had some issues at check in with alarm code and owner was quick to offer help. We messaged owner about the in home temperature and thermostat not working but did not hear back through vrbo messaging, so we delt with it being 80-83 degrees inside the home. Luckily we were gone most of the day Saturday and Sunday for work functions and left first thing Monday morning. Wish we had more time to enjoy the property though, it was beautiful. The...
Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
10.0 out of 10, Exceptional, (151)
"Family of 9 grandparents son and daughter in law and children. Lovely home very well equipped. Great location very close to all the central Florida attractions. The estate where the house is located is immaculate and in itself has good amenities. The owner provides detailed and clear instructions and communication with her was very quick. Would highly recommend"
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
⭐⭐⭐⭐⭐Champions Gate, all amenities included Luxury as New Platinum Pool Townhome
9.6 out of 10, Exceptional, (81)
"We had an awesome time. It was a birthday trip for my grandsons. The home was clean and spacious. The area was great as well! Management responded to questions and concerns quickly. Overall everything was great!"
⭐⭐⭐⭐⭐Champions Gate, all amenities included Luxury as New Platinum Pool Townhome
Beautiful South Facing Lake View 8BR/6BA, Custom Furniture
10.0 out of 10, Exceptional, (80)
"Very clean and very roomy…. We loved it… great location! Only 25-30 to Hollywood Studios , and like 45 min to Universal. Loved it!! Property manager was great also!"
Beautiful South Facing Lake View 8BR/6BA, Custom Furniture
Sandyridge Villa book now for 2024/25 book now get pool heat, cleaning included
9.6 out of 10, Exceptional, (80)
"The property was very clean and spacious. The pool was great and the hot tub was nice. My kids really enjoyed the games room in the garage. The area is close to lots of shops and restaurants as well as easy access to I-4. There are only two tv’s in the house, in the master and the second living room which was just outside the master so it wasn’t the best for watching both tvs at the same time, but we didn’t watch too much tv during our stay so it wasn’t too much of a issue for us. There are lots...
Sandyridge Villa book now for 2024/25 book now get pool heat, cleaning included
OH BOY!! STAY AT MINNIE'S MANSION! NEWLY UPDATED! PRIVATE POOL, GAME R00M!!
10.0 out of 10, Exceptional, (6)
"Don’t hesitate book this property! We absolutely loved this property and the amenities. It was clean and spacious. We traveled with family including kids. This property has a pool and a gameroom with fun things for the kiddos. This property is located so close to Disney, Walmart, restaurants. The property is in a gated community and is quiet. The kitchen had plenty of dishes, pots and pans. They provided pool towels as well. The host replies very quickly and provided great service. We will stay...
OH BOY!! STAY AT MINNIE'S MANSION! NEWLY UPDATED! PRIVATE POOL, GAME R00M!!
Luxury 5-Bedroom Villa with secluded Pool & Games Room only 10 miles from Disney
9.8 out of 10, Exceptional, (6)
"Our family had a great stay. This house is spacious, clean and close to attractions. The pool and spa was so nice in the evenings. I would stay here again!"
Luxury 5-Bedroom Villa with secluded Pool & Games Room only 10 miles from Disney
Luxury 4 Bedroom/3 Bathroom Villa with Relaxing Lakeview Private Pool, Grill & Arcade/Game Room!
10.0 out of 10, Exceptional, (10)
"Took my girlfriend and her two girls down to a week long get away in Kissimmee. Last year we rented another one of Shaun’s properties, we knew what to expect . The girls however , it was their first time and they absolutely fell in love with the home and the area . Whenever I vacation in Kissimmee I will always try to book one of Shaun’s properties. I will always recommend shaun !!!!!"
Luxury 4 Bedroom/3 Bathroom Villa with Relaxing Lakeview Private Pool, Grill & Arcade/Game Room!
Grand Opening! Windsor 10BD Disney Villa for large group! Pool/Game/BBQ/5 Kings!
10.0 out of 10, Exceptional, (23)
"We had a great time with our married kids and grands! A total of 33 and had plenty of room!"
Grand Opening! Windsor 10BD Disney Villa for large group! Pool/Game/BBQ/5 Kings!
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See all available properties in Winter Haven
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.

Other property types in Winter Haven

Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (6013)
"I love it been staying here for years n every stay it gets better"
The price is $55
$79 total
includes taxes & fees
Jun 9 - Jun 10
Ramada by Wyndham Kissimmee Gateway
Summer Bay Orlando by Exploria Resorts
3.5 star property
8.4 out of 10, Very Good, (4760)
"Property offered so many activities you could participate in for all ages and had such a gorgeous view"
The price is $139
$188 total
includes taxes & fees
Jun 9 - Jun 10
Summer Bay Orlando by Exploria Resorts
Seralago Hotel & Suites Main Gate East
3.0 star property
5.2 out of 10, (5300)
"Very basic nothing to brag about "
The price is $42
$65 total
includes taxes & fees
Jun 9 - Jun 10
Seralago Hotel & Suites Main Gate East
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.

Winter Haven Villas information

Number of reviews
1,197
Accommodation
7305 Villas
Lowest Price
Highest Price

Frequently asked questions

How much do villas in Winter Haven cost?
Expect to pay between and 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.
What are the best villas in Winter Haven?
Travelers recommend Private Pool 3 Bedroom Home By Redawning. Base yourself at this 3.5-star property which features a swimming pool and free self parking. Ov4051 - Southern Dunes - 3 Bed 2. 5 Baths Villa is another top-rated option to consider. Unpack your bags at this 3.5-star stay and you’ll have access to conveniences such as a swimming pool and pool sun loungers. You can pick from multiple villas in Winter Haven with a total average guest review rating of 9.7.
How many villas are there in Winter Haven?
Pack your bags and choose from 7305 villas in Winter Haven. For a family vacation, a couple’s getaway and everything in between, Expedia can help you find the ideal place in just a click or two.
Are there any family-friendly villas in Winter Haven?
There certainly are! We suggest Private Pool 3 Bedroom Home By Redawning — a comfortable 3.5-star property located a quick drive from downtown Winter Haven. This family-friendly villa includes conveniences like a swimming pool and a tennis court. After checking in and chilling out together in your cozy digs, it’s time to hit the road and discover some of the local sights. LEGOLAND® Florida and Chain Of Wakes are among the best family-friendly attractions in Winter Haven.
Why book your villa in Winter Haven with Expedia?
Reserving a villa in Winter Haven is as simple as clicking on your travel dates and selecting a place that meets your requirements. Want something affordable or upmarket, or a property that also features a pool? Use Expedia’s search filters to narrow your results and find your ideal match.
How can I find cheap villas in Winter Haven?
Expedia is here to help you easily locate cheap villas in Winter Haven. Simply use our handy filter tool to choose star rating, amenities and budget to refine your search and find a perfect stay in just a few clicks.
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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