Search Hotels with Pool in Winter Haven

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Pool

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

LEGOLAND Beach Retreat

3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (140)
"Overall great exsprience. Satff,rooms and amenities were great"
United States
Tanisha
The price is 7.091.378 ₫
8.975.734 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
LEGOLAND Beach Retreat
Outdoor pool, open 7:00 AM to 10:00 PM, pool 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, (1005)
"Clean room, great staff, easy check-in."
United States
Vanessa
The price is 3.664.318 ₫
4.104.036 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Winter Haven by IHG
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, (257)
"Great property. Great Staff! We had a very relaxing stay! "
United States
Wendy
The price is 3.775.038 ₫
4.228.042 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Home2 Suites By Hilton Winter Haven
Outdoor pool, pool umbrellas, pool loungers
Hampton Inn Winter Haven

Hampton Inn Winter Haven

2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1003)
"Clean room, staff was nice, breakfast was good, easy parking."
United States
Jessica
The price is 3.142.350 ₫
3.519.431 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Hampton Inn Winter Haven
Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, pool loungers
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
Winter Haven
7.0 out of 10, Good, (1007)
"Nice hotel. Clean and great location. "
United States
Raylene
The price is 2.241.450 ₫
2.510.424 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Howard Johnson by Wyndham Winter Haven FL
Outdoor pool, pool umbrellas, pool loungers
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, (1073)
"Clean rooms, great staff"
United States
Whitney
The price is 3.545.162 ₫
3.970.581 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Best Western Plus Winter Haven Inn & Suites 
Outdoor pool, pool loungers
Lake Roy Beach Inn

Lake Roy Beach Inn

2.0 star property
Winter Haven
7.0 out of 10, Good, (987)
"Great very nice comfortable room"
United States
Rian
The price is 2.562.386 ₫
2.869.873 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Lake Roy Beach Inn
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers
Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven

3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (730)
"Great staff, great location "
United States
katherine
The price is 4.245.570 ₫
4.755.038 ₫ total
includes taxes & fees
16 Dec - 17 Dec
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.
View all properties

Top Winter Haven Hotel Reviews

Explore a world of travel with Expedia

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.
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 Peppa Pig Theme Park Florida. 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.