Search Hotels with Pool in Winter Haven

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Check availability on Winter Haven Hotels with Pool

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winter Haven hotels with a pool

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

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
The price is ฿7,582
฿9,710 total
includes taxes & fees
3 Jan - 4 Jan 2026
LEGOLAND Beach Retreat
Seasonal outdoor pool
Home2 Suites By Hilton Winter Haven

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
The price is ฿4,561
฿5,108 total
includes taxes & fees
4 Jan - 5 Jan 2026
Home2 Suites By Hilton Winter Haven
Outdoor pool, pool umbrellas, pool loungers
Hampton Inn Winter Haven

Hampton Inn Winter Haven

Hampton Inn Winter Haven
2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1000)
"Clean room, staff was nice, breakfast was good, easy parking."
United States
Jessica
The price is ฿3,287
฿3,681 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Winter Haven
Outdoor pool, pool umbrellas, pool loungers
Best Western Plus Winter Haven Inn & Suites 

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, (1089)
"Clean rooms, great staff"
United States
Whitney
The price is ฿4,306
฿4,823 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Winter Haven Inn & Suites 
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

Howard Johnson by Wyndham Winter Haven FL
2.0 star property
Winter Haven
7.0 out of 10, Good, (1000)
"Nice hotel. Clean and great location. "
United States
Raylene
The price is ฿2,641
฿2,958 total
includes taxes & fees
29 Dec - 30 Dec
Howard Johnson by Wyndham Winter Haven FL
Outdoor pool, pool loungers
Lake Roy Beach Inn

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
The price is ฿3,020
฿3,383 total
includes taxes & fees
27 Dec - 28 Dec
Lake Roy Beach Inn
Outdoor pool, open 7:00 AM to 10:00 PM, pool loungers
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (1000)
"Was ok Regular Holiday inn experience Staff were nice "
United States
Nadav
The price is ฿4,475
฿5,011 total
includes taxes & fees
12 Jan - 13 Jan 2026
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

Courtyard by Marriott Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (734)
"Great staff, great location "
United States
katherine
The price is ฿5,376
฿6,021 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Winter Haven
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

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent
"Está muy bueno"
Sayuri 6-night trip
Posted 1 day ago
Holiday Inn Resort Kissimmee by the Parks by IHG

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.