Find Hotels with a Pool in Winter Haven, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Haven Hotels with a Pool

Tonight
25 Mar - 26 Mar
Tomorrow
26 Mar - 27 Mar
This weekend
27 Mar - 29 Mar
Next weekend
3 Apr - 5 Apr

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

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (183 reviews)
The price is AED 860
AED 1,107 total
includes taxes & fees
26 Mar - 27 Mar
LEGOLAND Beach Retreat
Outdoor pool, pool umbrellas, sun loungers

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
3.5 star property
Winter Haven
9.4 out of 10, Exceptional, (1,183 reviews)
  • cleanliness
    Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
The price is AED 513
AED 574 total
includes taxes & fees
29 Mar - 30 Mar
Best Western Plus Winter Haven Inn & Suites 
Outdoor pool, pool umbrellas, sun loungers

Hampton Inn Winter Haven

Hampton Inn Winter Haven
2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
The price is AED 506
AED 567 total
includes taxes & fees
5 Apr - 6 Apr
Hampton Inn Winter Haven
Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers

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 AED 507
AED 568 total
includes taxes & fees
29 Mar - 30 Mar
Holiday Inn Winter Haven by IHG
Dining

Home Away from Home Winter Haven! Disney, Legoland, Bok Tower, Golf, Medical Ctr

Home Away from Home Winter Haven! Disney, Legoland, Bok Tower, Golf, Medical Ctr
Winter Haven
9.4 out of 10, Exceptional, (3 reviews)
The price is AED 680
AED 1,264 total
includes taxes & fees
26 Mar - 27 Mar
Home Away from Home Winter Haven! Disney, Legoland, Bok Tower, Golf, Medical Ctr
Property grounds

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 AED 419
AED 469 total
includes taxes & fees
2 Apr - 3 Apr
Lake Roy Beach Inn
Seasonal outdoor pool

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (312 reviews)
  • cleanliness
    Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
The price is AED 651
AED 729 total
includes taxes & fees
12 Apr - 13 Apr
Home2 Suites By Hilton Winter Haven
Outdoor dining

Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Heated Pool and Hot tub-near Legoland, Disney, Theme parks
Winter Haven
9.8 out of 10, Exceptional, (46 reviews)
The price is AED 764
AED 1,587 total
includes taxes & fees
31 Mar - 1 Apr
Heated Pool and Hot tub-near Legoland, Disney, Theme parks
Outdoor pool

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Cheerful 4 Bed, 3 Bath Home with Screened Pool
Winter Haven
10.0 out of 10, Exceptional, (24 reviews)
The price is AED 992
AED 1,964 total
includes taxes & fees
28 Mar - 29 Mar
Cheerful 4 Bed, 3 Bath Home with Screened Pool
Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
2.0 star property
Winter Haven
7.2 out of 10, Good, (1,008 reviews)
  • cleanliness
    Splash into fun with sun loungers and umbrellas at this hotel's relaxing outdoor pool.
The price is AED 406
AED 455 total
includes taxes & fees
1 Apr - 2 Apr
Howard Johnson by Wyndham Winter Haven FL
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

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

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (183)
The price is AED 860
AED 1,107 total
includes taxes & fees
26 Mar - 27 Mar
LEGOLAND Beach Retreat
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

Westgate Town Center Resort

Westgate Town Center Resort

10/10 Excellent
"Awesome staf"
h aime bruno 6-night trip
Posted less than an hour ago
Westgate Town Center Resort

Explore a world of travel with Expedia

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.