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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

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

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 ￥17,940
￥20,092 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Winter Haven Inn & Suites 
Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers

2. 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 price is ￥16,527
￥18,510 total
includes taxes & fees
Aug 9 - Aug 10
Holiday Inn Winter Haven by IHG
Outdoor pool, pool umbrellas, sun loungers

3. 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 ￥16,212
￥18,157 total
includes taxes & fees
Aug 16 - Aug 17
Staybridge Suites Winter Haven Auburndale by IHG
Outdoor pool, pool umbrellas, sun loungers

4. 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 ￥17,940
￥20,092 total
includes taxes & fees
Aug 15 - Aug 16
Hampton Inn Winter Haven
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers

5. 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 ￥22,250
￥24,920 total
includes taxes & fees
Aug 27 - Aug 28
Courtyard by Marriott Winter Haven
Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers

6. 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 ￥13,379
￥14,984 total
includes taxes & fees
Aug 13 - Aug 14
Howard Johnson by Wyndham Winter Haven FL
Seasonal outdoor pool

7. Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (366 reviews)
  • cleanliness
    Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
The price is ￥22,119
￥24,773 total
includes taxes & fees
Aug 23 - Aug 24
Home2 Suites By Hilton Winter Haven
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

8. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
8.8 out of 10, Excellent, (335 reviews)
The price is ￥31,762
￥41,830 total
includes taxes & fees
Aug 29 - Aug 30
LEGOLAND Beach Retreat
2 outdoor pools, open 11:00 AM to 9:00 PM, pool umbrellas, sun loungers

9. Legoland Florida Hotel

Legoland Florida Hotel
3.0 star property
Winter Haven
8.6 out of 10, Excellent, (173 reviews)
  • cleanliness
    Resort offers 2 outdoor pools, waterslide, and optional water park in family-friendly setting.
The price is ￥45,489
￥57,118 total
includes taxes & fees
Sep 1 - Sep 2
Legoland Florida Hotel
Property grounds

10. 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.
The price is ￥13,790
￥15,444 total
includes taxes & fees
Aug 17 - Aug 18
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.
View all properties

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 ￥17,940
￥20,092 total
includes taxes & fees
Sep 1 - Sep 2
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

Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"Had an awesome time booking here again"
Emilia 3-night trip
Posted less than an hour ago
Delta Hotels by Marriott Orlando Celebration

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.