Find Luxury Hotels in Winter Haven, FL

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Our top choices for Winter Haven luxury hotels

Magical Dreams

Magical Dreams
4.0 star property
Kissimmee
5.6 out of 10, (19 reviews)
"Overall was a good stay . "
United States
Sorina
The price is ¥10,549
¥22,662 total
includes taxes & fees
Mar 7 - Mar 8
Magical Dreams

Lake Breeze 6 Bedrooms

Lake Breeze 6 Bedrooms
4.0 star property
Kissimmee
Lake Breeze 6 Bedrooms

Florida Breeze

Florida Breeze
4.0 star property
Bellavida
The price is ¥52,744
¥120,078 total
includes taxes & fees
Mar 18 - Mar 19
Florida Breeze

Willow Bend

Willow Bend
4.0 star property
Crescent Lakes
10.0 out of 10, Exceptional, (2 reviews)
"this house abuts woods and a slow river that made the property peaceful "
United States
John
The price is ¥37,703
¥99,268 total
includes taxes & fees
Mar 24 - Mar 25
Willow Bend

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very Good, (3,073 reviews)
"Overall the stay was great. Staff were very helpful. We had some issues with the room carpet but it was taken care of as soon as I reported to the front desk. I very much recommend this place."
United States
Lucia
Regal Oaks Resort Vacation Townhomes by IDILIQ

Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
Celebration
8.8 out of 10, Excellent, (1,590 reviews)
"Would definitely stay here again"
United States
Brad
The price is ¥13,706
¥21,278 total
includes taxes & fees
Mar 23 - Mar 24
Meliá Orlando Celebration

The Inn at Celebration, Autograph Collection

The Inn at Celebration, Autograph Collection
4.0 star property
Celebration Town Center
8.8 out of 10, Excellent, (937 reviews)
"Great room, extremely clean, food and staff were great. "
United States
Christopher
The price is ¥34,501
¥45,933 total
includes taxes & fees
Mar 15 - Mar 16
The Inn at Celebration, Autograph Collection

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)
"The room was clean and everything was great."
United States
Ock Chul
The price is ¥34,121
¥106,424 total
includes taxes & fees
Mar 26 - Mar 27
Encore Resort and Water Park at Reunion by Rentyl

Hills Bay Retreat

Hills Bay Retreat
4.0 star property
Bridgewater Crossing
10.0 out of 10, Exceptional, (3 reviews)
"Spacious and clean; everything you need plus a covered pool. We cut our stay short; evacuated before Hurricane Milton. "
United States
Michael E
The price is ¥36,234
¥98,867 total
includes taxes & fees
Mar 10 - Mar 11
Hills Bay Retreat

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando
4.0 star property
Kissimmee
9.0 out of 10, Wonderful, (4,711 reviews)
"Clean, quality accommodations with friendly staff."
United States
Terry
The price is ¥18,082
¥25,867 total
includes taxes & fees
Mar 22 - Mar 23
Hilton Vacation Club Mystic Dunes Orlando
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.

Top Winter Haven Hotel Reviews

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 want to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding 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 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 there to see and do in Winter Haven?
Take in the sights and attractions that Winter Haven offers with a visit to LEGOLAND® Florida, Theatre Winter Haven, and Chain of Lakes Park. If you have extra time while you're in the area, you might want to stop by Peppa Pig Theme Park Florida and The Circle B Bar Reserve.
How can I get around Winter Haven?
It's easier to get around town comfortably when you know your options. To venture out into the surrounding area, hop aboard a train at Winter Haven Station.