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Compare 325 Resorts in Winter Haven with updated reviews, rates, and availability.

Margaritaville Resort Orlando
Aerial view

Margaritaville Resort Orlando

4.0 star property
9.0 out of 10, Wonderful, (3173)
"Love the property Hate that pool closed so early At least have a jacuzzi open late"
The price is AED 543
AED 769 total
includes taxes & fees
18 Dec - 19 Dec
Margaritaville Resort Orlando
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
Exterior

Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel

4.0 star property
8.6 out of 10, Excellent, (1543)
"We loved our villa! The kitchen was fully stocked, the rooms were clean and comfortable, the backyard was nice for the kids to get their energy out. We went to the lazy river and arcade and those were fun. We appreciated the short drive to Epcot. Would stay again! "
The price is AED 400
AED 565 total
includes taxes & fees
25 Nov - 26 Nov
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
Westgate Vacation Villas Resort
Pool

Westgate Vacation Villas Resort

4.0 star property
7.8 out of 10, Good, (1465)
"The suite was amazing and staff was extremely helpful."
The price is AED 331
AED 500 total
includes taxes & fees
1 Dec - 2 Dec
Westgate Vacation Villas Resort
WorldMark Reunion
Outdoor pool

WorldMark Reunion

4.0 star property
9.4 out of 10, Exceptional, (463)
"It was a great spacious property. Only negative is the amenities all were closed by 5pm or 6pm so if you are getting back from the parks in the heavy traffic you arrive back to your accomodations just as everything is closing so the evening is pretty boring"
WorldMark Reunion
Encore Resort at Reunion
Water park

Encore Resort at Reunion

5.0 star property
8.4 out of 10, Very Good, (887)
"It was great"
Encore Resort at Reunion
Westgate Town Center Resort
Water park

Westgate Town Center Resort

4.0 star property
7.8 out of 10, Good, (1143)
"Everything is great "
The price is AED 331
AED 489 total
includes taxes & fees
1 Dec - 2 Dec
Westgate Town Center Resort
Disney 2 miles w/Heated Pool, water park, basketball tennis courts, game room
Dining

Disney 2 miles w/Heated Pool, water park, basketball tennis courts, game room

9.6 out of 10, Exceptional, (5)
"We enjoyed this property!! Close enough to everything but far enough away to avoid the hustle. When we come back to Orlando we will be booking this property again!"
Disney 2 miles w/Heated Pool, water park, basketball tennis courts, game room
Designer Renovated Condo in Gorgeous Tropical Setting
Room

Designer Renovated Condo in Gorgeous Tropical Setting

9.6 out of 10, Exceptional, (147)
"Loved the house, the pools and the property. "
Designer Renovated Condo in Gorgeous Tropical Setting
Spacious upgraded 1st floor condo w/ Resort Amenities. Disney, less than 15 mins
Living room looking towards kitchen and dining room

Spacious upgraded 1st floor condo w/ Resort Amenities. Disney, less than 15 mins

10.0 out of 10, Exceptional, (22)
"Very clean and nice ammenities. There was a big beatle looking bug and they called exterminator right away. Only suggestion would be to find a wayto put a bigger tv in bed aroom. Also some kind of foot rest in shoeer to be able to shave. in"
Spacious upgraded 1st floor condo w/ Resort Amenities. Disney, less than 15 mins
Lakefront Oasis: 10 Min to Disney, 5-Star Cleanliness + Resort Amenities!
Heated Pool

Lakefront Oasis: 10 Min to Disney, 5-Star Cleanliness + Resort Amenities!

10.0 out of 10, Exceptional, (50)
"This property and host were top notch. Communication with Jullian was timely and helpful in answering the questions we had. Property was clean and exactly as advertised. Close to all the parks and I4 so getting everywhere was a breeze. Pool on property was great with waterslides and the kids loved it. We will definitly be coming back!!!!"
Lakefront Oasis: 10 Min to Disney, 5-Star Cleanliness + Resort Amenities!
Disney Vacation Villa. Free Water park and Disney Shuttle. Themed Room.
Miscellaneous

Disney Vacation Villa. Free Water park and Disney Shuttle. Themed Room.

10.0 out of 10, Exceptional, (3)
"Couldn’t have found a better place for our group. The house was absolutely perfect and so much space. Definitely on our saved for future trips list."
Disney Vacation Villa. Free Water park and Disney Shuttle. Themed Room.
Cozy 2-bedroom resort less than 20 minutes away from Orlando theme parks.
Pool

Cozy 2-bedroom resort less than 20 minutes away from Orlando theme parks.

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was the best place we have stayed at so far. We have annual passes and come to Orlando often. as a large family we try to find the best and affordable accommodations. This was beyond what we expected,, and definitely plan on staying here again. it is super close to the parks . has so many activities in the resort itself and just very comfy and in inviting.I highly recommend."
Cozy 2-bedroom resort less than 20 minutes away from Orlando theme parks.
AMAZING STUDIO AT WESTGATE TOWN CENTER RESORT & SPA NEAR DISNEY
Pool

AMAZING STUDIO AT WESTGATE TOWN CENTER RESORT & SPA NEAR DISNEY

9.0 out of 10, Wonderful, (84)
"I arrived very early and they accommodated me by having my room ready. "
AMAZING STUDIO AT WESTGATE TOWN CENTER RESORT & SPA NEAR DISNEY
GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY
Pool

GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY

9.2 out of 10, Wonderful, (57)
"Out vacation was simply amazing!!! We enjoyed the property and all it had to offer, will definitely book again."
GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY
STUNNING 🤩 9 BEDS POOL HOME !!
Living area

STUNNING 🤩 9 BEDS POOL HOME !!

9.2 out of 10, Wonderful, (36)
"I had 2 fishing rods left at this home email owner no answer and the tods were very costly I really appreciate getting them back...But overall stay was Great"
STUNNING 🤩 9 BEDS POOL HOME !!
Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath
Brand New King Size bed with Stearns and foster mattress

Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath

9.8 out of 10, Exceptional, (47)
"I really enjoyed my stay at Champions Gate. The property was very clean, located in a great area. Communication with the host Mark was great. I would most definitely stay at this property again."
The price is AED 217
AED 761 total
includes taxes & fees
25 Nov - 26 Nov
Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath
PROMO 10% WEEKLY DISCOUNT! Fun-Filled Family Getaways Near the Magic of Disney
Pool

PROMO 10% WEEKLY DISCOUNT! Fun-Filled Family Getaways Near the Magic of Disney

9.8 out of 10, Exceptional, (23)
"We were very impressed right from the first moment we walked in. The place was very nice. We did have issues with one of the tvs and internet, but they helped us get these issues addressed quickly. We stayed for 8 days and found this location to be very comfortable. The pool areas were kept clean and nicely maintained. Easy in and out even though it is a gated community. Everything you would need for dining shopping or gas are all very close and even some within walking distance. The only bummer...
PROMO 10% WEEKLY DISCOUNT! Fun-Filled Family Getaways Near the Magic of Disney
Nice resort rented for 7 days and 6 nights
Pool

Nice resort rented for 7 days and 6 nights

Nice resort rented for 7 days and 6 nights
GREAT STUDIO AT RESORT NEAR DISNEY
Pool

GREAT STUDIO AT RESORT NEAR DISNEY

8.4 out of 10, Very Good, (26)
"This property is so clean and nice"
GREAT STUDIO AT RESORT NEAR DISNEY
Spacious 2-bedroom suite at Vacation Village-minutes from Orlando's theme parks!
Room

Spacious 2-bedroom suite at Vacation Village-minutes from Orlando's theme parks!

10.0 out of 10, Exceptional, (5)
"The condo is very nice, spacious and clean. The property is beautiful and very conveniently located within Orlando. Andy is a fantastic host! I highly recommend this rental."
Spacious 2-bedroom suite at Vacation Village-minutes from Orlando's theme parks!
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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Other property types in Winter Haven

Seralago Hotel & Suites Main Gate East
Exterior

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5565)
"I had to wait 20 minutes for the front counter lady to come in from smoking. The security guard was sitting in the lobby playing on his phone and he just kept saying she will be back soon.. Then she told me I had booked a double bed room and I said no I booked a family suite.. So I had to show her my email and she said well I don't know why they put you in another room, let me make sure I have a clean one.. After standing in the lobby for a total of 40 minutes (including her smoke break time), I...
The price is AED 144
AED 238 total
includes taxes & fees
24 Nov - 25 Nov
Seralago Hotel & Suites Main Gate East
Summer Bay Orlando by Exploria Resorts
Property amenity

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5025)
"Our unit was clean but in definite need of an update. The carpet was threadbare and torn in some areas. We still had a great stay and appreciated the prompt attention from security when we needed access to our unit."
The price is AED 479
AED 654 total
includes taxes & fees
8 Dec - 9 Dec
Summer Bay Orlando by Exploria Resorts
Margaritaville Resort Orlando Cottages by Rentyl
Front of property

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1084)
"This is our third time staying at Margaritaville (cottage the first time, villas the second and third time); I must say this villa was the least taken care of. It wasn’t super clean and the slider had some damage regarding opening/closing the blinds and locking/unlocking the sliding glass door. The front door didn’t have a safety lock at all (it looked to have been removed) so that made us a little uneasy. Our bed (queen) was very bouncy and it seemed to cave a little in the middle. Overall, it...
Margaritaville Resort Orlando Cottages by Rentyl
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.

Frequently asked questions

What is Winter Haven like for a resort vacation?
Longing for a relaxing escape? You deserve the luxuries and comforts of a resort, where you can find everything you need for your vacation from tasty food and drink options to entertainment and shopping. Browse the resorts in the area and discover the best one for you, whether you see yourself kicking back in a luxury suite or hitting the golf course for an afternoon game.
What's the best resort for my stay in Winter Haven?
Our top-rated resorts near Winter Haven: The Grove Resort & Water Park Orlando - Family-friendly resort. 23.9 mi (38.4 km) from Winter Haven. Features 3 outdoor pools, 3 restaurants, and 2 poolside bars. Guests love the pool. Margaritaville Resort Orlando - Spa resort. 23.4 mi (37.6 km) from Winter Haven. Has 3 outdoor pools, 3 restaurants, and 3 bars. Popular for its pool. Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel - Family-friendly resort. 23.8 mi (38.4 km) from Winter Haven. Highly rated for its pool. Enjoy the 7 outdoor pools, 8 restaurants, and 2 poolside bars. Westgate Vacation Villas Resort - Family-friendly resort. 22.8 mi (36.8 km) from Winter Haven. Amenities include 14 outdoor pools, 4 restaurants, and 2 bars. Guests love the proximity to shopping. Westgate Town Center Resort - Family-friendly resort. 22.7 mi (36.6 km) from Winter Haven. Access to 14 outdoor pools, 4 restaurants, and 3 bars.
How many resorts can I expect to find in Winter Haven?
Take your pick from Expedia’s 21 resort hotels in Winter Haven where you can enjoy onsite spas, fantastic guest rooms, and more.
What can I do in Winter Haven?
Travelers enjoy exploring the gardens, and also like the baseball games and other sporting events. Grab your golf clubs for a game at Baytree Golf Club and Cypresswood Golf and Country Club, or take the whole family to LEGOLAND® Florida and Indigo’s Family Fun Center. For more to see in the area, you can spend time at Theatre Winter Haven or Inman Park.
What's the seasonal weather like in Winter Haven?
The hottest months are usually August and July with an average temp of 81°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Haven are August, July, September, and June, with each month seeing an average of 8 inches of rainfall.
What's the best way to get to and around Winter Haven?
Fly into Kissimmee, FL (ISM-Kissimmee Gateway), which is located 26 mi (41.9 km) from the city center. Otherwise, look for flights into Avon Park, FL (AVO-Avon Park Executive), which is 32.1 mi (51.7 km) away. To venture out into the surrounding area, hop on a train at Winter Haven Station.