5 Stars Hotels in Winter Haven, Florida from CA $285

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Winter Haven 5 Star Hotels

Our top choices for Winter Haven 5-star hotels

ette hotel

ette hotel
5.0 star property
Kissimmee
9.6 out of 10, Exceptional, (448 reviews)
"Excelente"
United States
Daniel
The price is CA $379
CA $430 total
includes taxes & fees
May 25 - May 26
ette hotel

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, (1,004 reviews)
"Great vacation"
Canada
Vladislav
The price is CA $379
CA $1,024 total
includes taxes & fees
May 25 - May 26
Encore Resort and Water Park at Reunion by Rentyl

Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,562 reviews)
"Great resort for families very clear and friendly "
Canada
Cory
Reunion Resort & Golf Club

The Bear's Den Resort Orlando

The Bear's Den Resort Orlando
5.0 star property
Reunion
7.8 out of 10, Good, (24 reviews)
"Great place , I recommend it to everyone."
United States
Jacqueline
The Bear's Den Resort Orlando

Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills
5.0 star property
Tuscan Hills
8.8 out of 10, Excellent, (8 reviews)
"The unique rooms were a hit with our children."
United States
Joseph
Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

Gorgeous 5Bd Screened Pool at Champions Gate 1125

Gorgeous 5Bd Screened Pool at Champions Gate 1125
5.0 star property
Davenport
9.6 out of 10, Exceptional, (4 reviews)
"The house was exactly as the pictures posted. Very well maintained, cleaned, and well equipped with all essential equipment for cooking ext. My family and I loved it. It exceeded our expectations! We truly recommend this house, and will definitely rent this house again."
United States
Carmen
Gorgeous 5Bd Screened Pool at Champions Gate 1125

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
5.0 star property
Davenport
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place so many things to do. Great place to stay for a large family especially with kids "
United States
Yesenia
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158

Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

Stunning 5Bd w/ Pool @ Windsor Island Resort 3814
5.0 star property
Davenport
8.6 out of 10, Excellent, (9 reviews)
"It was a very nice play with a lot to do. Everything was worth the money. Clean, friendly, and fun."
United States
Matthew Cyril
Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

Wonderful 8Bd w/ Pool & GameRoom @ Encore 461
5.0 star property
Kissimmee
5.6 out of 10, (4 reviews)
"The coffee pot was broke, we emailed about it and received a new one within a a few hours. The listing says water park access but you don’t get water park access. The dryer was broken and unable to be fixed during our stay. The company is very attentive to needs. I brought up something’s in the house that probably need evaluated and they said things need to be addressed at the beginning on the stay. (Things like the fridge seal not being great, broken can opener, broken pool chairs ) make sure...
United States
Bronte
Wonderful 8Bd w/ Pool & GameRoom @ Encore 461

Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access

Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access
5.0 star property
Kissimmee
8.0 out of 10, Very good, (4 reviews)
"The house was huge we had enough room for everyone I loved the theme rooms and it was quiet "
United States
Tameko
Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access

7 Bedroom Villa, Private Pool, Resort Amenities

7 Bedroom Villa, Private Pool, Resort Amenities
5.0 star property
Kissimmee
7.6 out of 10, Good, (20 reviews)
"We were very disappointed with this property. I asked to get hot tub and pool heated and i was willing to pay the $40 fee. I received no response from Expedia or the property manager until 2nd last day. I was trying everyday a few times a day. I finally got a response that the hot tub and pool heater were broken. If i knew this i wouldn't have booked this property. I had grandkids that would've loved to use this everyday. Also many things wrong in the house. Kitchen sink garberaror"
Canada
Janet
7 Bedroom Villa, Private Pool, Resort Amenities

Amazing 4Bd Screened Pool Close to Disney 4572

Amazing 4Bd Screened Pool Close to Disney 4572
5.0 star property
Bellavida
8.4 out of 10, Very good, (6 reviews)
" Great for our family, close to activities, parks, attractiins"
United States
Charlene
Amazing 4Bd Screened Pool Close to Disney 4572

Charming 3Bd Close to Disney @ Festival 1026

Charming 3Bd Close to Disney @ Festival 1026
5.0 star property
Festival
8.4 out of 10, Very good, (5 reviews)
"Nice location "
United States
Jianzhuang
Charming 3Bd Close to Disney @ Festival 1026

Anchor Cove Villa

Anchor Cove Villa
5.0 star property
Solterra Resort
Anchor Cove Villa

Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

Family Friendly 2 Bd Close to Disney @ Champions Gate 8899
5.0 star property
Davenport
8.4 out of 10, Very good, (11 reviews)
"the waterpark was amazing. The villa was clean and comfortable. We didn't want to leave and we would like to come again."
United States
Donald Lester
Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
5.0 star property
Clermont
9.6 out of 10, Exceptional, (7 reviews)
"Wonderful stay!"
Canada
Angela
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

Cozy 3Bd Close to Disney @ Enclaves at Festival 808

Cozy 3Bd Close to Disney @ Enclaves at Festival 808
5.0 star property
Festival
8.0 out of 10, Very good, (5 reviews)
"Property was beautiful host was very attentive and answered all my questions and concerns area was safe and quiet the pool pass did not work was my only issue but everything else was top tier "
United States
Brittany
Cozy 3Bd Close to Disney @ Enclaves at Festival 808

Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub

Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub
5.0 star property
Davenport
8.0 out of 10, Very good, (2 reviews)
"Everything was good for the most part. Except the hot tub wasnt working dor the first 2 days and was ice cold. Then when asked about heating the pool they said they could not do that which was fine because we had the hot tub. But then the pool ended up WAY too hot for the baby to even get in and after a long day in the sun you dont wanna jump in a super hot pool anyway. Overall the house was great just some minor issues. But the pool and hot tub was an issue since that was why we picked this...
United States
Valerie
Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub

Jasmine 4 Bedrooms

Jasmine 4 Bedrooms
5.0 star property
Seasons
10.0 out of 10, Exceptional, (1 review)
"The property was amazing. Quiet, convenient and it was very inviting. "
United States
Jose Antonio
Jasmine 4 Bedrooms

Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (13 reviews)
"Enjoy the accommodations view was wonderful and close to everything"
United States
Anonymous traveller
Reunion Resort & Golf Club
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winter Haven.
Still don't see what you're looking for?
See all properties in Winter Haven.
You can also use these popular filters to refine your search.
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.

Learn more about Winter Haven

Glide through LEGOLAND's colourful rides before cooling off at their water park on hot Florida afternoons. Chain of Lakes offers peaceful kayaking spots where you can paddle between waterways and spot wildlife at your own pace.

Top Winter Haven Hotel Reviews

Find out more about Winter Haven

Five Star Hotels in Winter Haven

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Winter Haven so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Winter Haven and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Winter Haven

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Winter Haven

The results are in, and Winter Haven 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Winter Haven! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winter Haven today and settle down in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Haven?
How much you pay for a 5-star hotel in Winter Haven can vary depending on the time of year you travel and how long you plan to be away, among a number of factors. Take advantage of our price per night filter and other search tools to land the best rate on a luxurious getaway.

  • Search for the lowest price per night from CA $285

What makes a hotel 5 stars in Winter Haven?
Exceptional guest service is the hallmark of every 5-star hotel in Winter Haven. From the instant you arrive, staff ensure your every need is met, whether recommending activities or providing a nightly turn-down service. On top of that, hotels have to offer upscale conveniences to qualify for a 5-star rating. These can include luxury baths, saunas or spas, swimming pools, fine dining kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Winter Haven?
Use our convenient filters to find a luxurious getaway in Winter Haven where most of what you need is included. Next, narrow down your results for accommodations that have 5 stars and are described as "All inclusive." The first thing on the agenda at these stays? Pure relaxation and indulgence.

Explore a world of travel with Expedia