Winter Haven Hotel Guide - Hotels with Pool in Winter Haven, Florida

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Check availability on Winter Haven Hotels with Pool

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
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (150 reviews)
"Overall great exsprience. Satff,rooms and amenities were great"
United States
Tanisha
The price is €233
includes taxes & fees
6 Feb - 7 Feb
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, (286 reviews)
"The room and staff were amazing. "
United States
Sandra
The price is €150
includes taxes & fees
18 Jan - 19 Jan
Home2 Suites By Hilton Winter Haven
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
7.0 out of 10, Good, (1,014 reviews)
"Nice hotel. Clean and great location. "
United States
Raylene
The price is €90
includes taxes & fees
19 Jan - 20 Jan
Howard Johnson by Wyndham Winter Haven FL
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
9.6 out of 10, Exceptional, (1,120 reviews)
"Excelent, clean room and Excelent breakfast, recommended this hotel "
United States
Julian
The price is €129
includes taxes & fees
19 Jan - 20 Jan
Best Western Plus Winter Haven Inn & Suites 
Outdoor pool, pool umbrellas, pool loungers

Hampton Inn Winter Haven

Hampton Inn Winter Haven
2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1,002 reviews)
"Location is very convenient to shopping & food options, everything was very close. Hotel is in a good location, safe & quiet"
United States
HOA
The price is €125
includes taxes & fees
25 Jan - 26 Jan
Hampton Inn Winter Haven
Property grounds

Lake Roy Beach Inn

Lake Roy Beach Inn
2.0 star property
Winter Haven
7.0 out of 10, Good, (996 reviews)
"The views are great here. Porch also very nice."
United States
Barbara
The price is €102
includes taxes & fees
16 Jan - 17 Jan
Lake Roy Beach Inn
Pool

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, (2 reviews)
"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
The price is €322
includes taxes & fees
19 Jan - 20 Jan
Spacious 4-bedroom house in pleasant Winter Haven with AC
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
9.0 out of 10, Wonderful, (1,001 reviews)
"Was ok Regular Holiday inn experience Staff were nice "
United States
Nadav
The price is €134
includes taxes & fees
19 Jan - 20 Jan
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
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (737 reviews)
"Great staff, great location "
United States
katherine
The price is €183
includes taxes & fees
26 Jan - 27 Jan
Courtyard by Marriott Winter Haven
Outdoor pool, pool umbrellas, pool 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, (692 reviews)
"Grwat stay"
United States
Carlos Manuel
The price is €150
includes taxes & fees
18 Jan - 19 Jan
Staybridge Suites Winter Haven Auburndale by IHG
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
"Units are beautifully made/decorated, complete with almost everything you need for short or long stay, huge and clean. Pools are not crowded. Staff are thorough with directions which help if you’ve never been here because the building is a bit confusing to get to from one unit to another. 😬 Overall we had a great experience and considering coming back next time we go to Orlando. "
Wynchelle 1-night trip
Posted 14 hours ago
The Grove Resort & Water Park Orlando

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.