TOP Hotels with Pool in Winter Haven, FL for 2026

Q: 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.

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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, pool loungers

LEGOLAND Beach Retreat

Winter Haven

Rp4.444.711 total

includes taxes & fees

15 Jun - 16 Jun

Outdoor pool, pool umbrellas, pool loungers

Hampton Inn Winter Haven

Winter Haven

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

Rp2.140.942 total

includes taxes & fees

12 Jul - 13 Jul

Best Western Plus Winter Haven Inn & Suites

Winter Haven

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

Rp2.544.406 total

includes taxes & fees

21 Jun - 22 Jun

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.

Rp2.680.429 total

includes taxes & fees

21 Jun - 22 Jun

Outdoor pool, open 7:00 AM to 10:00 PM, pool 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.

Rp2.320.371 total

includes taxes & fees

28 Jun - 29 Jun

Home2 Suites By Hilton Winter Haven

Winter Haven

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

Rp2.942.471 total

includes taxes & fees

28 Jun - 29 Jun

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

Rp1.700.272 total

includes taxes & fees

20 Jun - 21 Jun

Lake Roy Beach Inn

Winter Haven

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

Rp1.764.211 total

includes taxes & fees

15 Jun - 16 Jun

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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 curtains, iron/ironing board

Best Western Plus Winter Haven Inn & Suites

Winter Haven

Rp2.544.406 total

includes taxes & fees

21 Jun - 22 Jun

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

Rp2.680.429 total

includes taxes & fees

21 Jun - 22 Jun

Blackout curtains, iron/ironing board, free cots/infant beds

Howard Johnson by Wyndham Winter Haven FL

Winter Haven

Rp1.700.272 total

includes taxes & fees

20 Jun - 21 Jun

Home2 Suites By Hilton Winter Haven

Winter Haven

Rp2.942.471 total

includes taxes & fees

28 Jun - 29 Jun

Courtyard by Marriott Winter Haven

Winter Haven

Rp3.213.514 total

includes taxes & fees

21 Jun - 22 Jun

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Winter Haven

Rp1.700.272 total

includes taxes & fees

15 Jun - 16 Jun

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Top Winter Haven Hotel Reviews

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent

"Clean room and good breakfast and staff was helpful"

The Grove Resort & Water Park Orlando

2/10 Terrible

"Unfortunately, this was not a great experience. The room had a strong chlorine smell throughout our stay, and the stove was broken when we arrived. The most frustrating part was dining at the hotel’s restaurant, Valencia. We were told there would be a 30-minute wait, which was completely understandable. However, after waiting over 30 minutes, we checked on our table and saw multiple families being seated ahead of us while we continued to wait. That experience left a very negative impression. Customer service was also disappointing. Trying to reach the front desk was incredibly difficult, and on one occasion I waited nearly 25 minutes just for someone to answer the phone. Overall, there were too many issues for us to fully enjoy our stay. I would not choose this hotel again."

Howard Johnson by Wyndham Winter Haven FL

10/10 Excellent

"Staff is great here! Family run business and they clearly care! It’s an old Motel that has been around for quite some time, but it has been well maintained over the years with what looks like a recent paint job. These places were THE PLACE TO BE back in the day and I’m glad to see one still well maintained and glimpses into the past with old Howard Johnson framed pictures. If you’re looking for a great deal, this is it."

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.

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