Hotels with Swimming Pools in Winter Haven

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Check availability on Winter Haven Hotels with Swimming Pools

Tonight
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Hotels with Swimming Pools in Winter Haven

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, (134)
The price is S$279
includes taxes & fees
5 Dec - 6 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
9.0 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 S$406
includes taxes & fees
2 Dec - 3 Dec
Legoland Florida Hotel
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, (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 S$208
includes taxes & fees
7 Dec - 8 Dec
Home2 Suites By Hilton Winter Haven
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, (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 accommodation with friendly service and complimentary breakfast.
The price is S$138
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn Winter Haven
Outdoor pool, pool umbrellas, pool loungers
Best Western Plus Winter Haven Inn & Suites 

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 S$165
includes taxes & fees
30 Nov - 1 Dec
Best Western Plus Winter Haven Inn & Suites 
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, (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 S$150
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Winter Haven by IHG
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, (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 S$123
includes taxes & fees
30 Nov - 1 Dec
Howard Johnson by Wyndham Winter Haven FL
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, (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 S$215
includes taxes & fees
28 Dec - 29 Dec
Courtyard by Marriott Winter Haven
Outdoor pool, pool loungers
Lake Roy Beach Inn

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 S$126
includes taxes & fees
26 Dec - 27 Dec
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.
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Top Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"great resort very clean and the pools yes was heated! we had a great time I will definitely stay there every time I go to Orlando, we had the 3-bedroom condo, and it has everything we needed, and everting works perfect we had no issue at all 5 days we stayed there. highly recommended if you're looking to stay at nice clean resort and not overpriced at all "
kassem 5-night trip
Posted 1 day ago
The Grove Resort & Water Park Orlando

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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.
What are some accommodation options 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 such as LEGOLAND® Florida while you're in Winter Haven. Make a point to visit attractions such as 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 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.