A castle entrance with flags and banners, including a LEGO Kingdoms banner.

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
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Winter Haven hotels with a pool

A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.
A modern hotel lobby with a central reception desk, multiple light fixtures, and a patterned wall.
A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.
A modern hotel with a prominent entrance, multiple floors, and a parking lot.

1. Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
  • Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
SAR 459
SAR 514 total
includes taxes & fees
18 Oct - 19 Oct
Best Western Plus Winter Haven Inn & Suites 
A pool area with a wooden pergola, lounge chairs, and a view of the water.
A spacious indoor area with a bar, seating arrangements, and a large screen displaying content.
An outdoor patio with a fire pit, wicker furniture, and a view of a lake.
A Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.

2. Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
  • Splash into sunset magic at Winter Haven's outdoor pool featuring loungers and mountain views.
SAR 539
SAR 604 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Winter Haven
A swimming pool with lounge chairs and tables, surrounded by a white building with a brick facade.
A modern kitchen with a wooden counter, coffee machines, and a Coca-Cola refrigerator.
A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.
A modern kitchen with a dining area, a flat-screen TV, and a large window.

3. Staybridge Suites Winter Haven Auburndale by IHG

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.
SAR 503
SAR 564 total
includes taxes & fees
18 Oct - 19 Oct
Staybridge Suites Winter Haven Auburndale by IHG
A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.
A modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.
A hotel lobby with a reception desk, seating area, and a bar.
A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".

4. Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
  • Shimmering blue waters await at this family-friendly hotel with pool loungers and workout options.
SAR 444
SAR 497 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Winter Haven
A swimming pool with a poolside area, including lounge chairs and umbrellas, adjacent to a building with multiple windows and a brick facade.
A hotel reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.
A hotel room with two beds, a desk, a television, and a door leading to another room.
A hotel room with a desk, chair, sofa, and a painting on the wall.

5. Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
  • Dive into crystalline blue waters at this outdoor pool oasis with comfy loungers and sunshine appeal.
SAR 413
SAR 463 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Winter Haven by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by a building with red and beige walls.
An outdoor seating area with sofas, chairs, and a fire pit.
A hotel room with a desk, chair, sofa, ottoman, and a large window.
A modern lounge area with green upholstered chairs, a herringbone-patterned floor, and a large window providing natural light.

6. Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
  • Refresh yourself in the seasonal outdoor pool during warm months while staying minutes from LEGOLAND® Florida.
SAR 571
SAR 640 total
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton Winter Haven
A swimming pool area with people playing with building blocks.
A row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.
A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.
A colorful LEGO-themed beach retreat sign with a beach house and a gas station in the background.

7. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
SAR 785
SAR 1,026 total
includes taxes & fees
30 Oct - 31 Oct
LEGOLAND Beach Retreat
A circular pool with a metal ladder, surrounded by white lounge chairs and palm trees.
A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.
A hotel room with two beds, a TV, a microwave, and a desk with a lamp.
A bathtub with a white shower curtain, a grab bar, and a handheld showerhead.

8. Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
  • Splash into fun with sun loungers and umbrellas at this hotel's relaxing outdoor pool.
SAR 287
SAR 322 total
includes taxes & fees
20 Oct - 21 Oct
Howard Johnson by Wyndham Winter Haven FL
A dark brown leather sectional sofa with multiple cushions, a carpeted floor, and two wall-mounted dog portraits.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with a sink and countertop.
A view through a glass door of a backyard with a patio table and chairs, a grassy area, and a building in the background.
A dining area with a large table, chairs, and a wall clock.

9. 10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney

10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
Winter Haven
SAR 1,153
SAR 1,711 total
includes taxes & fees
15 Oct - 16 Oct
10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.
A cozy room with two armchairs, each with a cushion featuring a fish design. There is a small table with two lamps and a couple of potted plants. A decorative sign on the wall reads "hello."
A room with two beds, a small rug, and a staircase.
A kitchen with a black countertop, a microwave, a toaster, a coffee maker, and a clock.

10. The Russell Lake House

The Russell Lake House
Winter Haven
SAR 254
SAR 787 total
includes taxes & fees
15 Oct - 16 Oct
The Russell Lake House
View all properties

Choose what matters most at hotels with a pool in Winter Haven

Breakfast included
Hot tub
4 stars
5 stars
Water park

Hotels with pools and free breakfast in Winter Haven

A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.
A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.
A modern hotel lobby with a central reception desk, multiple light fixtures, and a patterned wall.
A modern hotel with a prominent entrance, multiple floors, and a parking lot.

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
SAR 459
SAR 514 total
includes taxes & fees
18 Oct - 19 Oct
Best Western Plus Winter Haven Inn & Suites 
A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".
A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.
A hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.
A hotel lobby with a reception desk, seating area, and a bar.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
SAR 444
SAR 497 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Winter Haven
An outdoor patio with a fire pit, wicker furniture, and a view of a lake.
A modern hotel lobby with a long reception desk, bar area, and seating arrangement.
A spacious indoor area with a bar, seating arrangements, and a large screen displaying content.
A Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
SAR 539
SAR 604 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Winter Haven
A hotel room with two beds, a desk, a television, and a door leading to another room.
A hotel dining area with multiple tables and chairs, ceiling lights, and artwork on the walls.
A swimming pool with a poolside area, including lounge chairs and umbrellas, adjacent to a building with multiple windows and a brick facade.
A hotel reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
SAR 413
SAR 463 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Winter Haven by IHG
A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.
A modern kitchen with a dining area, a flat-screen TV, and a large window.
A modern hotel room with a kitchenette, a dining area, and a bed.
A spacious, modern living area with a herringbone wood floor, a dining area with a wooden table and chairs, and a kitchen in the background.

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
SAR 503
SAR 564 total
includes taxes & fees
18 Oct - 19 Oct
Staybridge Suites Winter Haven Auburndale by IHG
An outdoor seating area with sofas, chairs, and a fire pit.
A modern kitchen with a central island, bar stools, and a refrigerator.
A modern lounge area with green upholstered chairs, a herringbone-patterned floor, and a large window providing natural light.
A reception desk with a sign reading "HOME 2 Suites by Hilton," a minibar, a refrigerator labeled "COLDER," and a snack shelf.

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
SAR 571
SAR 640 total
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton Winter Haven
A swimming pool area with people playing with building blocks.
A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.
A dining area with tables, chairs, and a colorful mural in the background.
A row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
SAR 785
SAR 1,026 total
includes taxes & fees
30 Oct - 31 Oct
LEGOLAND Beach Retreat
A hotel room with two beds, a TV, a microwave, and a desk with a lamp.
A restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.
A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.
A conference room with tables and chairs, pink sashes, and a stage with drapes.

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
SAR 287
SAR 322 total
includes taxes & fees
20 Oct - 21 Oct
Howard Johnson by Wyndham Winter Haven FL
A hotel room with a bed, two bedside tables, a desk, a chair, and a blue armchair.
A hotel room with a television, two armchairs, a small table, and a patterned carpet.
A room with a small kitchenette, a blue ironing board, a trash bin, and a metal rack with black straps.
A reception area with a wooden floor, seating arrangements, and a reception desk.

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
SAR 303
SAR 340 total
includes taxes & fees
16 Oct - 17 Oct
Rodeway Inn & Suites Winter Haven Chain Of Lakes
A pool with floating building blocks and a colorful building with balconies in the background.
A dining area with tables and chairs, a central cart with dishes, and large windows with a view of greenery.
A room with a stone wall, a fireplace, and a sign that reads "YE OLD ADULTS KEEP OUT!".
Two LEGO figures in front of a colorful hotel building with a sign that reads "HOTEL".

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
SAR 879
SAR 1,131 total
includes taxes & fees
27 Oct - 28 Oct
Legoland Florida Hotel
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

8/10 Good
"Layout and amenities were good. Restocking of items in the Delta Pantry and pool towel areas were non-existent at night. Food at the lobby area was very good. Pools were nice and well maintained. Rooms were clean, some furnishings are outdated and worn. Check in and access in and out were very good."
Doug 5-night trip
Posted 1 hour ago
Delta Hotels by Marriott Orlando Celebration
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

10/10 Excellent
"Room was clean and it was the right price."
Selena 1-night trip
Posted 6 hours ago
Howard Johnson by Wyndham Winter Haven FL
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"We’ve stayed at Mystic Dunes in Orlando twice and have really enjoyed our stays! The condos are spacious, the grounds are clean and well maintained, and there are three pools on the property. The location is also great—close to Disney, with a Walmart just around the corner, which is super convenient. The kitchens are stocked with everything you need, including pots, pans, cleaning supplies, soaps, and more. The kitchens are on the smaller side and can feel a little cramped, but it was nice having everything available. There is also a washer and dryer in the condo, which is a big plus. One thing to keep in mind when booking is that the condos have a maximum of two bedrooms per condo. Some units have a shared entryway with two separate condo doors, so what may appear like a larger setup can actually be two separate condos. If you’re traveling with small children or need three bedrooms together, this is definitely something to check ahead of time. There is one pool bar that serves food and drinks, but if you aren’t staying close by, you’ll definitely want a car to get around. There is no hot tub, which would be a nice addition. Overall, we’ve had two enjoyable stays and would definitely consider staying at Mystic Dunes again. It’s a comfortable, convenient option for a Disney-area trip, especially if you like having a little more space than a typical hotel room!"
Christiana 3-night trip
Posted 21 hours ago
Hilton Vacation Club Mystic Dunes Orlando

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 8 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?
Courtyard by Marriott Winter Haven: Hotel located near LEGOLAND® Florida. Features free self parking, a pool, and complimentary wireless internet access. Economy Suites: Offers free self parking, an outdoor pool, and complimentary wireless internet access.
How many pool hotels should I expect to find in Winter Haven?
Expedia has 8 hotels in Winter Haven for your poolside break.
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 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 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.