Search Hotels with Pool in Winter Haven

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Check availability on Winter Haven Hotels with Pool

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

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, (232 reviews)
"Loved the pool and the activities they have!"
United States
Tatiana
The price is ฿7,597
฿9,781 total
includes taxes & fees
9 Jun - 10 Jun
LEGOLAND Beach Retreat
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, (1,005 reviews)
  • cleanliness
    Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
"Pool was great and heated"
United States
Gary
The price is ฿3,725
฿4,172 total
includes taxes & fees
7 Jun - 8 Jun
Hampton Inn Winter Haven
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)
  • cleanliness
    Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.
"The pool was clean"
United States
Careem
The price is ฿3,701
฿4,145 total
includes taxes & fees
14 Jun - 15 Jun
Holiday Inn Winter Haven by IHG
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, (335 reviews)
  • cleanliness
    Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
"Pool was nice and clean"
United States
Katherine
The price is ฿4,499
฿5,039 total
includes taxes & fees
14 Jun - 15 Jun
Home2 Suites By Hilton Winter Haven
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
9.4 out of 10, Exceptional, (1,277 reviews)
  • cleanliness
    Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
"The pool area was nice too!"
United States
Wilma
The price is ฿4,284
฿4,798 total
includes taxes & fees
31 May - 1 Jun
Best Western Plus Winter Haven Inn & Suites 
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, (794 reviews)
  • cleanliness
    Refreshing outdoor pool oasis with loungers and umbrellas provides a sun-soaked relaxation spot near LEGOLAND Florida.
"Had plenty of amenities including, pool, great full breakfast, complimentary laundry room, and full kitchens."
United States
leah desiderio
The price is ฿4,123
฿4,618 total
includes taxes & fees
14 Jun - 15 Jun
Staybridge Suites Winter Haven Auburndale by IHG
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
7.2 out of 10, Good, (1,006 reviews)
  • cleanliness
    Splash into fun with sun loungers and umbrellas at this hotel's relaxing outdoor pool.
"Stayed 4 nights quite- clean rooms-pool was nice to hang and swim. Didn't spend much time there but would recommend this place and stay again."
United States
Jamison
The price is ฿2,760
฿3,091 total
includes taxes & fees
9 Jun - 10 Jun
Howard Johnson by Wyndham Winter Haven FL
House (4 Bedrooms) | Interior

Legoland & Lakes Pool Home Pet Friendly

Legoland & Lakes Pool Home Pet Friendly
3.0 star property
Winter Haven
The price is ฿5,587
฿18,347 total
includes taxes & fees
27 May - 28 May
Legoland & Lakes Pool Home Pet Friendly
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, (761 reviews)
  • cleanliness
    Splash into sunset magic at Winter Haven's outdoor pool featuring loungers and mountain views.
"Great hotel with excellent staff from the moment we walked in! Clean rooms, good lobby rstaurant/bar…. And nice pool area! "
United States
JOSE
The price is ฿5,216
฿5,841 total
includes taxes & fees
14 Jun - 15 Jun
Courtyard by Marriott 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.
"Oh…and the pool surrounded by the beautiful landscape is wonderful!"
United States
Lori
The price is ฿2,863
฿3,207 total
includes taxes & fees
27 May - 28 May
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, (232)
The price is ฿7,597
฿9,781 total
includes taxes & fees
9 Jun - 10 Jun
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 Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Property is very clean. From the rooms to pool area and the grounds. Staff keeps you informed with daily updates on anything going on. Maintenance crew was great. Our air conditioner stopped working. They were out and had it fixed and running in an hour. This was our second time staying here. Will definitely come back."
Wayne 8-night trip
Posted less than an hour ago
Hilton Vacation Club Mystic Dunes 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?
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 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.