Find Hotels with a Pool in Winter Haven, FL

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Check availability on Winter Haven Hotels with a Pool

Top Winter Haven Hotels with a Pool

Kompose Boutique Resort at Theme Parks

3.0 star property
Kissimmee
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • 2 hot tubs
9.4 out of 10, Exceptional, (1807)
Vibrant poolside experiences await with a thrilling waterslide, luxurious hot tubs, and refreshing drinks served at the bar. Families love the spacious, modern rooms while the sauna and 24-hour fitness center provide additional relaxation options.
The price is NT$1,484
NT$2,925 total
includes taxes & fees
Dec 1 - Dec 2
Kompose Boutique Resort at Theme Parks

Disney's All-Star Movies Resort

3.5 star property
Lake Buena Vista
  • 2 outdoor pools
  • Poolside bar
  • Pool loungers
8.8 out of 10, Excellent, (1001)
Disney's All-Star Movies Resort

voco Kissimmee Orlando by IHG

4.0 star property
Kissimmee
  • Outdoor pool
  • Children's pool
7.4 out of 10, Good, (1011)
Splash into vacation bliss at dual outdoor pools—one just for kids—after an exhilarating day exploring nearby theme parks. Complimentary shuttle service whisks families to Disney attractions, while babysitting services offer parents peaceful poolside moments.
The price is NT$2,100
NT$3,092 total
includes taxes & fees
Dec 16 - Dec 17
voco Kissimmee Orlando by IHG

LEGOLAND Beach Retreat

3.0 star property
Winter Haven
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (132)
The price is NT$5,883
NT$7,814 total
includes taxes & fees
Dec 20 - Dec 21
LEGOLAND Beach Retreat

Legoland Florida Hotel

3.0 star property
Winter Haven
  • 2 outdoor pools
  • Pool loungers
9.4 out of 10, Exceptional, (42)
Splash into refreshing adventures at dual outdoor pools complete with a waterslide, loungers, and playful pool toys. Beyond aquatic fun, this Legoland Florida Hotel offers character encounters, American cuisine at Bricks Family Restaurant, and shopping on site.
The price is NT$8,970
NT$11,271 total
includes taxes & fees
Dec 8 - Dec 9
Legoland Florida Hotel

Hampton Inn Winter Haven

2.5 star property
Winter Haven
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1005)
Poolside relaxation awaits at this welcoming Winter Haven retreat, where the outdoor swimming area features comfortable loungers under shady umbrellas. Located near LEGOLAND® Florida, this hotel combines spotless accommodations with friendly service and complimentary breakfast.
The price is NT$2,974
NT$3,331 total
includes taxes & fees
Nov 30 - Dec 1
Hampton Inn Winter Haven

Home2 Suites By Hilton Winter Haven

3.0 star property
Winter Haven
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
9.4 out of 10, Exceptional, (237)
Seasonal swimming awaits at this well-appointed hotel featuring a sparkling outdoor pool perfect for sun-soaked relaxation. Guests appreciate the exceptional cleanliness, spacious rooms with kitchenettes, and complimentary breakfast buffet with quality options.
The price is NT$4,099
NT$4,591 total
includes taxes & fees
Nov 30 - Dec 1
Home2 Suites By Hilton Winter Haven

Holiday Inn Winter Haven by IHG

3.0 star property
Winter Haven
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1007)
Aquatic pleasures await at the pristine outdoor pool, surrounded by sun loungers and open from early morning until evening. Guests appreciate the hotel's friendly staff, clean rooms, and convenient Café Blu restaurant on site.
The price is NT$3,473
NT$3,889 total
includes taxes & fees
Dec 22 - Dec 23
Holiday Inn Winter Haven by IHG

Courtyard by Marriott Winter Haven

3.0 star property
Winter Haven
  • Outdoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (727)
Sparkling waters beckon at the outdoor pool where sun loungers provide perfect relaxation spots with breathtaking sunrise and sunset views. Beyond swimming, guests praise the bistro's delicious meals and the convenient location near LEGOLAND Florida.
The price is NT$3,968
NT$4,444 total
includes taxes & fees
Nov 30 - Dec 1
Courtyard by Marriott Winter Haven

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
Winter Haven
  • Outdoor pool
  • Pool loungers
7.0 out of 10, Good, (1007)
Poolside paradise awaits with sun loungers and umbrellas creating the perfect spot to unwind after exploring local attractions. Friendly staff, comfortable rooms, and an on-site Mexican restaurant with happy hour complete this relaxing Winter Haven escape.
The price is NT$2,654
NT$2,973 total
includes taxes & fees
Nov 23 - Nov 24
Howard Johnson by Wyndham Winter Haven FL
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

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Frequently asked questions

What's it like visiting Winter Haven?
If lounging next to a pool is your idea of the perfect getaway, you may want to check out family-friendly Winter Haven, which has 18 places to stay with pools. While you're here, you can explore sights such as LEGOLAND® Florida, and then relax and unwind poolside at one of the accommodations in Winter Haven that travelers like for their pools.
What are some accommodations with pools in Winter Haven?
Courtyard by Marriott Winter Haven: Hotel located near LEGOLAND® Florida. Features free self parking, a pool, and complimentary wireless internet access. Economy Suites: Offers free self parking, an outdoor pool, and complimentary wireless internet access.
How many pool hotels should I expect to find in Winter Haven?
Expedia's 18 hotels in Winter Haven give you a great choice for your poolside getaway.
What is there to see and do in Winter Haven?
Explore places like LEGOLAND® Florida while you're in Winter Haven. Make a point to visit attractions like The Circle B Bar Reserve and Peppa Pig Theme Park Florida. Winter Haven appeals to visitors with its beautiful lakeside setting and array of dining options.
When is the best time to book a hotel with a pool in Winter Haven?
You may want to consider a place to stay with an outdoor pool if you'll be visiting Winter Haven in the driest months of November, December, or February when the average rainfall is 2 inches. Lodging with an indoor pool may be the way to go if you are visiting during the rainiest months of August, July, and September when the average rainfall is 8 inches.
What's the best way to travel around Winter Haven?
Knowing the transportation options in Winter Haven can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop on a train at Winter Haven Station. Winter Haven may not have many public transit options so consider renting a car to explore more.