The Best Hotels with a Pool in Winter Haven, FL from ₩136,125 in 2026

Q: What are some accommodations 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.

Check availability on Winter Haven Hotels with a Pool

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Our top choices for Winter Haven hotels with a pool

Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

LEGOLAND Beach Retreat

Winter Haven

₩377,581 total

includes taxes & fees

Jun 16 - Jun 17

Outdoor pool, pool umbrellas, sun loungers

Hampton Inn Winter Haven

Winter Haven

Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.

₩208,044 total

includes taxes & fees

Jun 29 - Jun 30

Best Western Plus Winter Haven Inn & Suites

Winter Haven

Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.

₩216,149 total

includes taxes & fees

Jun 21 - Jun 22

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

Refreshing outdoor pool oasis with loungers and umbrellas provides a sun-soaked relaxation spot near LEGOLAND Florida.

₩220,908 total

includes taxes & fees

Jul 5 - Jul 6

Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers

Holiday Inn Winter Haven by IHG

Winter Haven

Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.

₩193,719 total

includes taxes & fees

Jul 5 - Jul 6

Home2 Suites By Hilton Winter Haven

Winter Haven

Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.

₩249,422 total

includes taxes & fees

Jul 12 - Jul 13

Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers

Howard Johnson by Wyndham Winter Haven FL

Winter Haven

Splash into fun with sun loungers and umbrellas at this hotel's relaxing outdoor pool.

₩144,439 total

includes taxes & fees

Jun 29 - Jun 30

Lake Roy Beach Inn

Winter Haven

Lakeside pool paradise awaits with serene water views and complimentary loungers for ultimate relaxation.

₩149,871 total

includes taxes & fees

Jun 19 - Jun 20

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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

Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room) | Desk, laptop workspace, blackout drapes, iron/ironing board

Best Western Plus Winter Haven Inn & Suites

Winter Haven

₩216,149 total

includes taxes & fees

Jun 21 - Jun 22

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

₩220,908 total

includes taxes & fees

Jul 5 - Jul 6

Blackout drapes, iron/ironing board, free cribs/infant beds

Howard Johnson by Wyndham Winter Haven FL

Winter Haven

₩144,439 total

includes taxes & fees

Jun 29 - Jun 30

Home2 Suites By Hilton Winter Haven

Winter Haven

₩249,422 total

includes taxes & fees

Jul 12 - Jul 13

Courtyard by Marriott Winter Haven

Winter Haven

₩272,989 total

includes taxes & fees

Jun 21 - Jun 22

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Winter Haven

₩144,439 total

includes taxes & fees

Jun 16 - Jun 17

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Top Winter Haven Hotel Reviews

Galleria Palms Hotel

8/10 Good

"All the staff we interacted with were pleasant and helpful. The room was clean. The breakfast was okay but shut down early. The only reason I did not give it an excellent on everything was because the pool was not opened (in fact had no water in it) I felt that should have been mentioned in the description for when booking the room.. Other than that I would stay again."

The Adventure Hotel by the parks

10/10 Excellent

"I really loved my stay. Incredibly personable front desk staff. I had an issue with the TV (total user error) and they came promptly and didn't laugh at me lol. My only issue was the shower didn't get hot, it was mostly lukewarm but that was probably user error too. I was there for an interview (I'm a law student) and this hotel let me relax. I will stay there again"

Howard Johnson by Wyndham Winter Haven FL

2/10 Terrible

"1.) This hotel has a major problem with damp, moldy rooms, and they smell very bad. My clothes felt damp all the time, as did my sheets when I went to bed. While I was there, they shampooed the carpets, which made the rooms even worse and did very little for the stench. My plan was to stay 2 weeks due to my brother being in the hospital. 2.) The refrigerator in my room did not work. I asked the older man who is the owner/manager and wears glasses if I could have one that worked. It never happened. Finally, after 2 days of not getting it, I asked again, and this time he did it. In the meantime, I had to throw out food because I had no refrigeration. 3.) I did not know the password to sign in to the wi-fi, so I called the front desk, and the same older man answered. I asked him for the password; he had a very strong accent from his country, and I could not understand him. He ended up shouting at me several times. I had no idea what he was saying. Feeling intimidated, I just hung up. This man has no business working with the public because he is rude, and you can tell he hates his job or people in general. I checked out early due to him and his behavior."

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?

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 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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