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Find Hotels with a Pool in Winter Haven, FL

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Check availability on Winter Haven Hotels with a Pool

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16

Our top choices for Winter Haven hotels with a pool

Outdoor pool, pool umbrellas, sun loungers

1. 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, (1,330 reviews)
  • cleanliness
    Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
The price is ₩164,056
₩183,743 total
includes taxes & fees
Aug 25 - Aug 26
Best Western Plus Winter Haven Inn & Suites 
Outdoor pool, pool umbrellas, sun loungers

2. 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, (853 reviews)
  • cleanliness
    Refreshing outdoor pool oasis with loungers and umbrellas provides a sun-soaked relaxation spot near LEGOLAND Florida.
The price is ₩148,252
₩166,042 total
includes taxes & fees
Aug 9 - Aug 10
Staybridge Suites Winter Haven Auburndale by IHG
Outdoor pool, open 7:00 AM to 9:00 PM, sun loungers

3. Best Western Auburndale Inn & Suites

Best Western Auburndale Inn & Suites
3.5 star property
Auburndale
8.4 out of 10, Very Good, (1,002 reviews)
  • cleanliness
    Splash into Florida sunshine at this inviting hotel where loungers surround a clean, warm outdoor pool for all-day refreshment.
The price is ₩150,728
₩168,815 total
includes taxes & fees
Aug 6 - Aug 7
Best Western Auburndale Inn & Suites
Exterior

4. JC Inn

JC Inn
2.5 star property
Clermont
6.8 out of 10, (1,001 reviews)
  • cleanliness
    Take a splash in the sun-soaked outdoor pool with lounge chairs and umbrellas at this family hotel.
The price is ₩112,700
₩126,224 total
includes taxes & fees
Aug 2 - Aug 3
JC Inn
Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers

5. Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.
The price is ₩151,131
₩169,267 total
includes taxes & fees
Aug 9 - Aug 10
Holiday Inn Winter Haven by IHG
Reception

6. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (5,108 reviews)
  • cleanliness
    Splash down the waterslide or bask poolside at this modern family resort with two hot tubs.
The price is ₩56,290
₩127,586 total
includes taxes & fees
Aug 5 - Aug 6
Kompose Boutique Resort at Theme Parks
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

7. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
8.8 out of 10, Excellent, (335 reviews)
The price is ₩243,248
₩328,859 total
includes taxes & fees
Aug 28 - Aug 29
LEGOLAND Beach Retreat
Outdoor pool, pool umbrellas, sun loungers

8. Hampton Inn Winter Haven

Hampton Inn Winter Haven
2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
The price is ₩164,056
₩183,742 total
includes taxes & fees
Aug 15 - Aug 16
Hampton Inn Winter Haven
Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers

9. 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, (1,002 reviews)
  • cleanliness
    Splash into fun with sun loungers and umbrellas at this hotel's relaxing outdoor pool.
The price is ₩122,344
₩137,025 total
includes taxes & fees
Aug 5 - Aug 6
Howard Johnson by Wyndham Winter Haven FL
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers

10. Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (772 reviews)
  • cleanliness
    Splash into sunset magic at Winter Haven's outdoor pool featuring loungers and mountain views.
The price is ₩200,644
₩224,722 total
includes taxes & fees
Aug 27 - Aug 28
Courtyard by Marriott Winter Haven
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

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 

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, (1330)
The price is ₩164,056
₩183,743 total
includes taxes & fees
Aug 25 - Aug 26
Best Western Plus Winter Haven Inn & Suites 
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 Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"The amenities were amazing"
Jessica 7-night trip
Posted less than an hour ago
Hilton Vacation Club Aqua Sol Orlando West

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 20 places to stay with pools. While you're here, you can explore sights such as LEGOLAND® Florida and Reunion Resort Golf Course, and then relax and unwind poolside at one of the accommodations in Winter Haven that guests 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 20 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.