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Check availability on Winter Haven Luxury Hotels

Our top choices for Winter Haven luxury hotels

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, (9,921 reviews)
  • cleanliness
    Lakeside luxury surrounds at this resort with 6 pools, a water park, and premium lake views.
The price is ฿5,365
฿7,828 total
includes taxes & fees
25 May - 26 May
The Grove Resort & Water Park Orlando
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)
Disney's Animal Kingdom Villas - Jambo House
Lobby

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (3,608 reviews)
The price is ฿4,913
฿7,355 total
includes taxes & fees
18 Jun - 19 Jun
Margaritaville Resort Orlando with H2O Waterpark
Terrace/patio

Disney's Animal Kingdom Villas - Kidani Village

Disney's Animal Kingdom Villas - Kidani Village
4.0 star property
Bay Lake
9.0 out of 10, Wonderful, (169 reviews)
Disney's Animal Kingdom Villas - Kidani Village
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, (1,010 reviews)
  • cleanliness
    Elegant spa resort with water park offers pampered bliss in Kissimmee, a short drive from Disney's entertainment magic.
The price is ฿8,979
฿24,273 total
includes taxes & fees
20 May - 21 May
Encore Resort and Water Park at Reunion by Rentyl
5 outdoor pools, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)

Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate
4.0 star property
Champions Gate
9.0 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Lavish resort featuring spa, 6 pools, and championship golf offers luxury near Orlando attractions.
The price is ฿5,851
฿8,494 total
includes taxes & fees
24 May - 25 May
Omni Orlando Resort at ChampionsGate
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, (2,902 reviews)
The price is ฿4,865
฿6,746 total
includes taxes & fees
20 May - 21 May
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Outdoor pool

Aster Cove

Aster Cove
4.0 star property
Crescent Lakes
The price is ฿5,289
฿18,162 total
includes taxes & fees
20 May - 21 May
Aster Cove
Outdoor pool

Lakeview 6Br W/ Pool, Hot Tub & Near Theme Parks

Lakeview 6Br W/ Pool, Hot Tub & Near Theme Parks
4.5 star property
Lake Berkley
The price is ฿6,465
฿21,972 total
includes taxes & fees
20 May - 21 May
Lakeview 6Br W/ Pool, Hot Tub & Near Theme Parks
Outdoor pool, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)

Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
Celebration
8.8 out of 10, Excellent, (1,599 reviews)
  • cleanliness
    Refined elegance meets rejuvenating luxury at this family-friendly resort near Disney World with spa and pool.
The price is ฿2,841
฿4,410 total
includes taxes & fees
22 May - 23 May
Meliá Orlando Celebration
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

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

10/10 Excellent
"Great costumer"
Stacy ann 3-night trip
Posted 1 hour ago
Westgate Vacation Villas Resort

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Winter Haven?
Expedia can help you arrange a flight to Lakeland Intl. Airport (LAL) airport or Kissimmee, FL (ISM-Kissimmee Gateway) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay special. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can help you find the best luxury hotel experience that Winter Haven has to offer. Known for its entertainment and sporting events, Winter Haven also has some interesting things to see and do including LEGOLAND® Florida, so you may want to take in the local sights during your visit.
When can I expect good weather in Winter Haven?
Planning for the weather is an important factor for making your trip to Winter Haven a success, especially when you're splurging. 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 there to see and do in Winter Haven?
Take in the sights and attractions that Winter Haven offers with a visit to LEGOLAND® Florida, Indigo's Family Fun Center and Theatre Winter Haven. If you have extra time while you're in the area, you might want to stop by Chain of Lakes Park and Peppa Pig Theme Park Florida.
How can I get around Winter Haven?
It's easier to get around town comfortably when you know your options. If you want to venture outside the area, take a train from Winter Haven Station.