Find Hotels with a Pool in Winter Haven, FL

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Check availability on Winter Haven Hotels with a Pool

Our top choices for Winter Haven hotels with a pool

Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (178 reviews)
The price is ￥31,653
￥41,690 total
includes taxes & fees
Apr 5 - Apr 6
LEGOLAND Beach Retreat
Seasonal outdoor pool

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (311 reviews)
  • cleanliness
    Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
The price is ￥28,578
￥32,008 total
includes taxes & fees
Apr 12 - Apr 13
Home2 Suites By Hilton Winter Haven
Outdoor pool, pool umbrellas, sun loungers

Hampton Inn Winter Haven

Hampton Inn Winter Haven
2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
The price is ￥24,385
￥27,311 total
includes taxes & fees
Mar 25 - Mar 26
Hampton Inn Winter Haven
Outdoor pool, pool umbrellas, sun loungers

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
3.5 star property
Winter Haven
9.6 out of 10, Exceptional, (1,171 reviews)
  • cleanliness
    Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
The price is ￥24,062
￥26,949 total
includes taxes & fees
Mar 22 - Mar 23
Best Western Plus Winter Haven Inn & Suites 
Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.
The price is ￥21,564
￥24,152 total
includes taxes & fees
Mar 22 - Mar 23
Holiday Inn Winter Haven by IHG
Property grounds

Lake Roy Beach Inn

Lake Roy Beach Inn
2.0 star property
Winter Haven
7.0 out of 10, Good, (1,003 reviews)
  • cleanliness
    Lakeside pool paradise awaits with serene water views and complimentary loungers for ultimate relaxation.
The price is ￥17,051
￥19,097 total
includes taxes & fees
Apr 1 - Apr 2
Lake Roy Beach Inn
Outdoor pool, pool umbrellas, sun loungers

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
3.0 star property
Winter Haven
9.8 out of 10, Exceptional, (730 reviews)
  • cleanliness
    Refreshing outdoor pool oasis with loungers and umbrellas provides a sun-soaked relaxation spot near LEGOLAND Florida.
The price is ￥26,994
￥30,233 total
includes taxes & fees
Mar 22 - Mar 23
Staybridge Suites Winter Haven Auburndale by IHG
Dining

Home Away from Home Winter Haven! Disney, Legoland, Bok Tower, Golf, Medical Ctr

Home Away from Home Winter Haven! Disney, Legoland, Bok Tower, Golf, Medical Ctr
Winter Haven
9.4 out of 10, Exceptional, (3 reviews)
The price is ￥38,194
￥67,603 total
includes taxes & fees
Mar 18 - Mar 19
Home Away from Home Winter Haven! Disney, Legoland, Bok Tower, Golf, Medical Ctr
Outdoor pool

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Cheerful 4 Bed, 3 Bath Home with Screened Pool
Winter Haven
10.0 out of 10, Exceptional, (24 reviews)
Cheerful 4 Bed, 3 Bath Home with Screened Pool
Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
2.0 star property
Winter Haven
7.2 out of 10, Good, (1,002 reviews)
  • cleanliness
    Splash into fun with sun loungers and umbrellas at this hotel's relaxing outdoor pool.
The price is ￥17,652
￥19,770 total
includes taxes & fees
Apr 1 - Apr 2
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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Choose what matters most at hotels with a pool in Winter Haven

Breakfast included
Hot tub

Hotels with pools and free breakfast in Winter Haven

Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (178)
The price is ￥31,653
￥41,690 total
includes taxes & fees
Apr 5 - Apr 6
LEGOLAND Beach Retreat
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.
View all properties

Top Winter Haven Hotel Reviews

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Super great "
Johanna 1-night trip
Posted 6 hours ago
Hilton Vacation Club Aqua Sol Orlando West

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?
Economy Suites: Features free self parking, an outdoor pool, and complimentary wireless internet access. Courtyard by Marriott Winter Haven: Hotel located near LEGOLAND® Florida. Offers free self parking, a 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.