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Check availability on Winter Haven Hotels with Pool

Top Winter Haven Hotels with Pool

Outdoor pool, pool umbrellas, pool loungers
Kompose Boutique Resort at Theme Parks

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 centre provide additional relaxation options.
The price is 1.252.644 ₫
2.469.415 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Kompose Boutique Resort at Theme Parks
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
  • 2 outdoor pools
  • Poolside bar
  • Pool loungers
8.8 out of 10, Excellent, (1001)
Disney's All-Star Movies Resort
Bar (on property)
voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG

4.0 star property
Kissimmee
  • Outdoor pool
  • Children's pool
7.4 out of 10, Good, (1011)
Splash into holiday 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 1.645.925 ₫
2.466.882 ₫ total
includes taxes & fees
26 Nov - 27 Nov
voco Kissimmee Orlando by IHG
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers
LEGOLAND Beach Retreat

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 4.967.354 ₫
6.597.533 ₫ total
includes taxes & fees
20 Dec - 21 Dec
LEGOLAND Beach Retreat
2 outdoor pools, open 11:00 AM to 9:00 PM, pool umbrellas, pool loungers
Legoland Florida Hotel

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 7.572.837 ₫
9.515.555 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Legoland Florida Hotel
Outdoor pool, pool umbrellas, pool loungers
Hampton Inn Winter Haven

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 accommodation with friendly service and complimentary breakfast.
The price is 2.511.376 ₫
2.812.742 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn Winter Haven
Seasonal outdoor pool
Home2 Suites By Hilton 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 3.461.056 ₫
3.876.382 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Home2 Suites By Hilton Winter Haven
Outdoor pool, open 7:00 AM to 10:00 PM, pool loungers
Holiday Inn Winter Haven by IHG

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 2.933.122 ₫
3.285.097 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Holiday Inn Winter Haven by IHG
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers
Courtyard by Marriott Winter Haven

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 3.350.260 ₫
3.752.291 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Courtyard by Marriott Winter Haven
Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, pool loungers
Howard Johnson by Wyndham Winter Haven FL

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 2.242.045 ₫
2.511.090 ₫ total
includes taxes & fees
27 Nov - 28 Nov
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.
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Top Winter Haven Hotel Reviews

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Frequently asked questions

What's it like visiting Winter Haven?
If lounging by a pool is your idea of the perfect getaway, you might want to think about family-friendly Winter Haven, which has 18 places to stay with pools. During your trip, you can explore sights such as LEGOLAND® Florida, and then take it easy poolside at one of the accommodation options in Winter Haven that travellers like for their pools.
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 such as LEGOLAND® Florida while you're in Winter Haven. Make a point to visit attractions such as 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 that has an outdoor pool if you're planning to visit Winter Haven in the driest months of November, December or February, when the average rainfall is 47 mm. Accommodation 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 211 mm.
What's the best way to travel around Winter Haven?
Knowing the transportation options in and around Winter Haven can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, take a train from Winter Haven Station. Winter Haven might not have many public transport choices, so consider renting a car to explore more.