Find Hotels with a Pool in Winter Haven, FL

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Our top choices for Winter Haven hotels with a pool

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
9.2 out of 10, Wonderful, (145)
"Overall great exsprience. Satff,rooms and amenities were great"
United States
Tanisha
$279 nightly
The price is $312
Jan 3 - Jan 4, 2026
Total with taxes and fees
LEGOLAND Beach Retreat

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (265)
"Great room and location "
United States
Ashley
$147 nightly
The price is $164
Jan 4 - Jan 5, 2026
Total with taxes and fees
Home2 Suites By Hilton Winter Haven

Hampton Inn Winter Haven

Hampton Inn Winter Haven
2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1004)
"Clean room, staff was nice, breakfast was good, easy parking."
United States
Jessica
$106 nightly
The price is $118
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn Winter Haven

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
3.5 star property
Winter Haven
9.4 out of 10, Exceptional, (1087)
"Clean rooms, great staff"
United States
Whitney
$133 nightly
The price is $149
Dec 24 - Dec 25
Total with taxes and fees
Best Western Plus Winter Haven Inn & Suites 

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
2.0 star property
Winter Haven
7.0 out of 10, Good, (1004)
"Nice hotel. Clean and great location. "
United States
Raylene
$85 nightly
The price is $95
Dec 28 - Dec 29
Total with taxes and fees
Howard Johnson by Wyndham Winter Haven FL

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (1007)
"Clean room, great staff, easy check-in."
United States
Vanessa
$110 nightly
The price is $123
Dec 25 - Dec 26
Total with taxes and fees
Holiday Inn Winter Haven by IHG

Lake Roy Beach Inn

Lake Roy Beach Inn
2.0 star property
Winter Haven
7.0 out of 10, Good, (990)
"Great very nice comfortable room"
United States
Rian
$90 nightly
The price is $101
Dec 27 - Dec 28
Total with taxes and fees
Lake Roy Beach Inn

Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Heated Pool and Hot tub-near Legoland, Disney, Theme parks
Winter Haven
9.8 out of 10, Exceptional, (40)
"We had a great stay!"
United States
Harper B.
$309 nightly
The price is $343
Jan 15 - Jan 16, 2026
Total with taxes and fees
Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (733)
"Great staff, great location "
United States
katherine
$161 nightly
The price is $180
Dec 30 - Dec 31
Total with taxes and fees
Courtyard by Marriott Winter Haven

Spacious 4-bedroom house in pleasant Winter Haven with AC

Spacious 4-bedroom house in pleasant Winter Haven with AC
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (1)
"An outstanding stay! The house was extremely clean, welcoming, and had all the amenities that made our family vacation unforgettable in our visit to Legoland park"
Mexico
Monica
$326 nightly
The price is $361
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spacious 4-bedroom house in pleasant Winter Haven with AC
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

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.

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