Search Best Resorts in Winter Haven

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
29 May - 31 May
In two weeks
5 June - 7 June
In one month
19 June - 21 June
In two months
17 July - 19 July

Our top choices for Winter Haven resorts

2 outdoor pools, pool umbrellas, pool loungers

Disney's All-Star Music Resort

Disney's All-Star Music Resort
3.0 star property
Lake Buena Vista
8.8 out of 10, Excellent, (1,011 reviews)
"Great stay, friendly staff"
United States
Erika
Disney's All-Star Music Resort
Reception

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (4,132 reviews)
"Great place to stay."
Canada
Paulo Henrique
The price is AU$141
includes taxes & fees
25 May - 26 May
Kompose Boutique Resort at Theme Parks
Egyptian cotton sheets, premium bedding, down duvets, in-room safe

Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk
4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (760 reviews)
The price is AU$260
includes taxes & fees
1 June - 2 June
Embassy Suites By Hilton Orlando Sunset Walk
Lobby

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (3,599 reviews)
"Clean room and very very nice staff."
United States
Natjaree
The price is AU$284
includes taxes & fees
25 May - 26 May
Margaritaville Resort Orlando with H2O Waterpark
Lobby

Disney's Animal Kingdom Villas - Jambo House

Disney's Animal Kingdom Villas - Jambo House
4.0 star property
Bay Lake
8.6 out of 10, Excellent, (33 reviews)
"The best Disneyvacation ever!"
Sweden
Anonymous traveller
Disney's Animal Kingdom Villas - Jambo House
Aerial view

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
4.0 star property
Winter Garden
8.0 out of 10, Very good, (9,945 reviews)
"Very clean rooms and friendly staff"
United States
Michael
The price is AU$338
includes taxes & fees
25 May - 26 May
The Grove Resort & Water Park Orlando
Water park

Westgate Town Center Resort

Westgate Town Center Resort
4.0 star property
Kissimmee
8.2 out of 10, Very good, (1,731 reviews)
"The property and amenities were top notch!"
United States
Hilton
The price is AU$192
includes taxes & fees
25 May - 26 May
Westgate Town Center Resort
Outdoor pool, a heated pool

Spacious, Clean, Updated 2 Bedroom 2 Bathroom Close To Parks Golf and Amenities

Spacious, Clean, Updated 2 Bedroom 2 Bathroom Close To Parks Golf and Amenities
Champions Gate
10.0 out of 10, Exceptional, (24 reviews)
"Our stay at the condo was excellent. We used the fully furnished kitchen, swam in the pool, and enjoyed being close to our various destinations. "
United States
Larry H.
The price is AU$450
includes taxes & fees
25 May - 26 May
Spacious, Clean, Updated 2 Bedroom 2 Bathroom Close To Parks Golf and Amenities
Outdoor pool, a heated pool

Disney Universal Family Villa Resort with Elevator, Pool and many amenities!

Disney Universal Family Villa Resort with Elevator, Pool and many amenities!
Kissimmee
The price is AU$330
includes taxes & fees
26 May - 27 May
Disney Universal Family Villa Resort with Elevator, Pool and many amenities!
Outdoor pool, a heated pool

Paradise Room Resort Suite room near Disney and other interest places of Florida

Paradise Room Resort Suite room near Disney and other interest places of Florida
Regal Palms
9.8 out of 10, Exceptional, (7 reviews)
"The host was very accommodating all week long and responded to any questions we had within the hour. I would say she went beyond and above our normal VRBO experiences. The pools are a major plus and the restaurant was very convient! I will also say there is a major grocery store a block away and many restaurants within a short drive. "
United States
Anonymous traveller
The price is AU$194
includes taxes & fees
23 June - 24 June
Paradise Room Resort Suite room near Disney and other interest places of Florida
2 outdoor pools, pool umbrellas, pool loungers

Disney's All-Star Movies Resort

Disney's All-Star Movies Resort
3.5 star property
Lake Buena Vista
8.8 out of 10, Excellent, (1,004 reviews)
"Beautiful and friendly place"
United States
Denise
Disney's All-Star Movies Resort
Pool

Disney Home | Pool & Themed Bedrooms

Disney Home | Pool & Themed Bedrooms
Kissimmee
The price is AU$608
includes taxes & fees
27 May - 28 May
Disney Home | Pool & Themed Bedrooms
Exterior

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG
4.0 star property
Orange Lake
8.8 out of 10, Excellent, (2,916 reviews)
"I very beautiful and nice place to stay! "
United States
Lohana
The price is AU$290
includes taxes & fees
1 June - 2 June
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Outdoor pool, a heated pool

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

Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath
Champions Gate
9.4 out of 10, Exceptional, (67 reviews)
"Beautiful property to stay at! Property is very clean. There is a pool and restaurant on sight. Not far from Orlando and all the parks. Also close to a Publix. Owners are extremely easy to get in touch with. Will definitely stay here again!!"
United States
Maureen
The price is AU$333
includes taxes & fees
1 June - 2 June
Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath
Property grounds

Resort style near Disney and theme parks

Resort style near Disney and theme parks
Bahama Bay
The price is AU$403
includes taxes & fees
1 June - 2 June
Resort style near Disney and theme parks
Water park

Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
5.0 star property
Kissimmee
8.2 out of 10, Very good, (1,008 reviews)
"Great vacation"
Canada
Vladislav
The price is AU$1,043
includes taxes & fees
25 May - 26 May
Encore Resort and Water Park at Reunion by Rentyl
Aerial view

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort
4.0 star property
Kissimmee
8.2 out of 10, Very good, (1,932 reviews)
"Great place to visit!"
United States
Michael Anthony
The price is AU$183
includes taxes & fees
25 May - 26 May
Westgate Vacation Villas Resort
Pool

Cozy and perfect for a family time.

Cozy and perfect for a family time.
Clermont
The price is AU$226
includes taxes & fees
28 May - 29 May
Cozy and perfect for a family time.
Exterior

Stylish Waterpark Resort Near Orlando Parks

Stylish Waterpark Resort Near Orlando Parks
Davenport
The price is AU$738
includes taxes & fees
29 May - 30 May
Stylish Waterpark Resort Near Orlando Parks
Dining

Resort w/ AC + Private Bathroom 10-12 minutes from Disney world

Resort w/ AC + Private Bathroom 10-12 minutes from Disney world
Kissimmee
The price is AU$387
includes taxes & fees
25 May - 26 May
Resort w/ AC + Private Bathroom 10-12 minutes from Disney world
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.
View all properties
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

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent
"Very good 👏👏👏!!"
Fabio 2-night trip
Posted 6 hours ago
Ramada by Wyndham Kissimmee Gateway

Find out more about Winter Haven

Winter Haven Resort information

Number of reviews
28,169
Accommodation
417 Resort
Lowest Price
AU$141
Highest Price
AU$1,043

Frequently asked questions

What is Winter Haven like for a resort holiday?
Longing for a relaxing escape? Treat yourself to all the comforts and luxuries of a resort, where you can find everything you need for your holiday—from tasty food and drink options to activities and entertainment. Browse the resorts in the area and discover the best one for you, whether you picture yourself kicking back in a suite with stunning views or heading to the spa for a deep-tissue massage.
What's a favourite resort for my stay in Winter Haven?
Here are our top-rated resorts around Winter Haven: The Grove Resort & Water Park Orlando - Family-friendly resort. 24 mi (38.6 km) from Winter Haven. Features 6 outdoor pools, 3 restaurants and 3 poolside bars. Guests love the pool. Kompose Boutique Resort at Theme Parks - 23.3 mi (37.5 km) from Winter Haven. Has 2 hot tubs, a 24-hour fitness centre and a snack bar/deli. Margaritaville Resort Orlando with H2O Waterpark - Family-friendly resort. 23.3 mi (37.5 km) from Winter Haven. Highly rated for its pool. Enjoy the 3 outdoor pools, 3 restaurants and 3 bars. Holiday Inn Club Vacations at Orange Lake Resort by IHG - Family-friendly resort. 23.8 mi (38.4 km) from Winter Haven. Amenities include 7 outdoor pools, 9 restaurants and 2 poolside bars. Popular for its pool. Westgate Vacation Villas Resort - Family-friendly resort. 22.8 mi (36.8 km) from Winter Haven. Highly rated for its proximity to shopping. Access to 14 outdoor pools, 2 restaurants and 2 bars.
What can I do in Winter Haven?
Travellers enjoy exploring the gardens, and also like the baseball games and other sporting events. Grab your golf clubs for a round at Cypresswood Golf and Country Club and Willowbrook Golf Course, or take the whole family to LEGOLAND® Florida and Indigo's Family Fun Center. If you want more to do in the area, you can spend time at Theatre Winter Haven or Chain of Lakes Park.
What's the weather like in Winter Haven?
The hottest months are usually August and July, with an average temperature of 27°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Haven are August, July, September and June, with each month seeing an average of 211 mm of rainfall.
What's the best way to get to and around Winter Haven?
Fly into Lakeland Intl. Airport (LAL), which is located 17.3 mi (27.8 km) from the city centre. You can also search for flights into Kissimmee, FL (ISM-Kissimmee Gateway), which is 26 mi (41.9 km) away. If you want to venture outside the area, hop on a train at Winter Haven Station.

Explore a world of travel with Expedia