Find Hotels with a Pool in Winter Haven, FL

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Top Winter Haven Hotels with a Pool

LEGOLAND Beach Retreat

3.0 star property
Winter Haven
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (134)
The price is NT$5,902
NT$7,840 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
9.0 out of 10, Wonderful, (48)
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$7,660
NT$9,808 total
includes taxes & fees
Dec 2 - Dec 3
Legoland Florida Hotel

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, (247)
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$4,489
NT$5,027 total
includes taxes & fees
Dec 7 - Dec 8
Home2 Suites By Hilton Winter Haven

Hampton Inn Winter Haven

2.5 star property
Winter Haven
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1009)
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$2,984
NT$3,342 total
includes taxes & fees
Dec 7 - Dec 8
Hampton Inn Winter Haven

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
Winter Haven
  • Outdoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (1062)
Sparkling waters welcome families to the immaculately maintained outdoor pool area, complete with sun loungers and umbrellas for all-day comfort. Spotlessly clean rooms await after exciting adventures to nearby parks and attractions.
The price is NT$3,747
NT$4,197 total
includes taxes & fees
Nov 30 - Dec 1
Best Western Plus Winter Haven Inn & Suites 

Holiday Inn Winter Haven by IHG

3.0 star property
Winter Haven
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1013)
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$3,235
NT$3,623 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Inn Winter Haven by IHG

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
Winter Haven
  • Outdoor pool
  • Pool loungers
7.0 out of 10, Good, (1009)
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$2,664
NT$2,984 total
includes taxes & fees
Nov 29 - Nov 30
Howard Johnson by Wyndham Winter Haven FL

Courtyard by Marriott Winter Haven

3.0 star property
Winter Haven
  • Outdoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (728)
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$4,636
NT$5,192 total
includes taxes & fees
Dec 21 - Dec 22
Courtyard by Marriott Winter Haven

Lake Roy Beach Inn

2.0 star property
Winter Haven
  • Outdoor pool
  • Pool loungers
7.0 out of 10, Good, (982)
Poolside loungers surround the sparkling outdoor pool at this lakeside hotel, creating a perfect setting for sun-soaked relaxation. Screened-in porches offer peaceful sunset views over the water, complemented by immaculately clean grounds and attentive staff.
The price is NT$3,047
NT$3,412 total
includes taxes & fees
Dec 1 - Dec 2
Lake Roy Beach Inn
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 Indigo's Family Fun Center. 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.