The Best Hotels with a Pool in Winter Haven, FL from ₩139,806 in 2026

Q: What are some accommodations 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.

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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

Tanisha

₩503,131 total

includes taxes & fees

Jan 2 - Jan 3, 2026

Outdoor pool, pool umbrellas, sun loungers

Hampton Inn Winter Haven

Winter Haven

Jessica

₩213,101 total

includes taxes & fees

Dec 21 - Dec 22

Best Western Plus Winter Haven Inn & Suites

Winter Haven

Whitney

₩221,189 total

includes taxes & fees

Dec 21 - Dec 22

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

Howard Johnson by Wyndham Winter Haven FL

Winter Haven

Raylene

₩139,807 total

includes taxes & fees

Dec 30 - Dec 31

Lake Roy Beach Inn

Winter Haven

Rian

₩159,866 total

includes taxes & fees

Dec 17 - Dec 18

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

Holiday Inn Winter Haven by IHG

Winter Haven

Vanessa

₩194,084 total

includes taxes & fees

Dec 18 - Dec 19

Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers

Courtyard by Marriott Winter Haven

Winter Haven

katherine

₩286,321 total

includes taxes & fees

Dec 24 - Dec 25

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

Sofia

₩250,006 total

includes taxes & fees

Dec 18 - Dec 19

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Hotels with pools and free breakfast in Winter Haven

2 outdoor pools, open 11:00 AM to 9:00 PM, pool umbrellas, sun loungers

Legoland Florida Hotel

Winter Haven

₩664,490 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

₩221,189 total

includes taxes & fees

Dec 21 - Dec 22

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Winter Haven

₩139,807 total

includes taxes & fees

Dec 17 - Dec 18

Courtyard by Marriott Winter Haven

Winter Haven

₩286,321 total

includes taxes & fees

Dec 24 - Dec 25

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

Howard Johnson by Wyndham Winter Haven FL

Winter Haven

₩139,807 total

includes taxes & fees

Dec 30 - Dec 31

Home2 Suites By Hilton Winter Haven

Winter Haven

₩241,421 total

includes taxes & fees

Jan 4 - Jan 5, 2026

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

₩250,006 total

includes taxes & fees

Dec 18 - Dec 19

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Top Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

10/10 Excellent

"Room was larger and very clean "

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent

"I read some conflicting reviews on this place prior to booking. Since we were only going to be there one night, I chanced it. I can tell you, don’t believe the negative reviews or the 3 star rating given to this place. It’s easily a 4-5. The staff was extremely nice, the front lobby smelt amazing and was very clean and we had no issues with the room. Would absolutely stay again. "

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"Front desk was very professional and efficient. Even gave us a goodie bag with water upon check in. Rooms were spacious. Kitchen had many equipments that came in handy. Felt very safe. The gentle man at the gate during the night shift was very polite. We went in October and came back again in December. Good location, 10 mins from Panda Express, close to the parks, 5mins from Walmart. Would book again"

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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?

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 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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