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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
8.8 out of 10, Excellent, (303 reviews)
The price is €180
includes taxes & fees
30 Jul - 31 Jul
LEGOLAND Beach Retreat
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, (1,338 reviews)
  • cleanliness
    Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
The price is €120
includes taxes & fees
9 Aug - 10 Aug
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, (1,003 reviews)
  • cleanliness
    Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
The price is €111
includes taxes & fees
16 Aug - 17 Aug
Hampton Inn Winter Haven
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
8.8 out of 10, Excellent, (162 reviews)
  • cleanliness
    Resort offers 2 outdoor pools, waterslide, and optional water park in family-friendly setting.
The price is €396
includes taxes & fees
2 Aug - 3 Aug
Legoland Florida Hotel
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, (1,020 reviews)
  • cleanliness
    Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.
The price is €97
includes taxes & fees
2 Aug - 3 Aug
Holiday Inn Winter Haven by IHG
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, (845 reviews)
  • cleanliness
    Refreshing outdoor pool oasis with loungers and umbrellas provides a sun-soaked relaxation spot near LEGOLAND Florida.
The price is €94
includes taxes & fees
16 Aug - 17 Aug
Staybridge Suites Winter Haven Auburndale 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, (770 reviews)
  • cleanliness
    Splash into sunset magic at Winter Haven's outdoor pool featuring loungers and mountain views.
The price is €144
includes taxes & fees
2 Aug - 3 Aug
Courtyard by Marriott 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
7.4 out of 10, Good, (1,021 reviews)
  • cleanliness
    Splash into fun with sun loungers and umbrellas at this hotel's relaxing outdoor pool.
The price is €88
includes taxes & fees
11 Aug - 12 Aug
Howard Johnson by Wyndham Winter Haven FL
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, (361 reviews)
  • cleanliness
    Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
The price is €135
includes taxes & fees
2 Aug - 3 Aug
Home2 Suites By Hilton Winter Haven
Property grounds

Lake Roy Beach Inn

Lake Roy Beach Inn
2.0 star property
Winter Haven
7.0 out of 10, Good, (1,000 reviews)
  • cleanliness
    Lakeside pool paradise awaits with serene water views and complimentary loungers for ultimate relaxation.
The price is €86
includes taxes & fees
20 Jul - 21 Jul
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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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, pool loungers
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
8.8 out of 10, Excellent, (303)
The price is €180
includes taxes & fees
30 Jul - 31 Jul
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

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

8/10 Good
"Fue una buena opción y la atención de la recepción fue muy buena. La habitación está bien para un lugar donde se pasa poco tiempo."
Minor Antonio Chaves 5-night trip
Posted 9 hours ago
Holiday Inn & Suites Orlando SW - Celebration Area 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?
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 such as LEGOLAND® Florida while you're in Winter Haven. Make a point to visit attractions such as The Circle B Bar Reserve and Peppa Pig Theme Park Florida. 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.