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
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 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 swimming pool with lounge chairs and tables, surrounded by a white building with a brick facade.
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 modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

2. 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 563 total
includes taxes & fees
8 Nov - 9 Nov
Staybridge Suites Winter Haven Auburndale by IHG
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.
A Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.
An outdoor patio with a fire pit, wicker furniture, and a view of a lake.

3. 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 fence and a building with a modern design.
A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".
A hotel lobby with a reception desk, seating area, and a bar.
A modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.

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 room with two beds, a desk, a television, and a door leading to another room.
A bathroom with a shower, a toilet, a sink, and a mirror.
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.
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.
A modern kitchen with a central island, bar stools, and a refrigerator.

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 539
SAR 604 total
includes taxes & fees
15 Nov - 16 Nov
Home2 Suites By Hilton Winter Haven
A swimming pool area with people playing with building blocks.
A colorful LEGO-themed beach retreat sign with a beach house and a gas station 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.
A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.

7. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
SAR 784
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 bathtub with a white shower curtain, a grab bar, and a handheld showerhead.
A hotel room with two beds, a TV, a microwave, and a desk with a lamp.

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
27 Oct - 28 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 laundry area with two washers and dryers, a mop, and a basket.
A view through a glass door of a backyard with a patio table and chairs, a grassy area, and a building in the background.

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 1,712 total
includes taxes & fees
19 Oct - 20 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 room with two beds, a small rug, and a staircase.
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 residential property with a paved driveway, a lawn, and mature trees with hanging moss.

10. The Russell Lake House

The Russell Lake House
Winter Haven
SAR 253
SAR 787 total
includes taxes & fees
18 Oct - 19 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 hotel lobby with a reception desk, seating area, and a bar.
A hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.
A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.

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
A hotel room with two beds, a desk, a television, and a door leading to another room.
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 room with a desk, chair, sofa, and a painting on the wall.
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 spacious, modern living area with a herringbone wood floor, a dining area with a wooden table and chairs, and a kitchen in the background.
A modern kitchen with a wooden counter, coffee machines, and a Coca-Cola refrigerator.
A modern hotel room with a kitchenette, a dining area, and a bed.

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
SAR 503
SAR 563 total
includes taxes & fees
8 Nov - 9 Nov
Staybridge Suites Winter Haven Auburndale by IHG
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 Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.
A spacious indoor area with a bar, seating arrangements, and a large screen displaying content.

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 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 conference room with tables and chairs, pink sashes, and a stage with drapes.
A reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
SAR 287
SAR 322 total
includes taxes & fees
27 Oct - 28 Oct
Howard Johnson by Wyndham Winter Haven FL
An outdoor seating area with sofas, chairs, and a fire pit.
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.
A hotel room with a desk, chair, sofa, ottoman, and a large window.

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
SAR 539
SAR 604 total
includes taxes & fees
15 Nov - 16 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 dining area with tables, chairs, and a colorful mural in the background.

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
SAR 784
SAR 1,026 total
includes taxes & fees
30 Oct - 31 Oct
LEGOLAND Beach Retreat
A pool with floating building blocks and a colorful building with balconies in the background.
A room with a stone wall, a fireplace, and a sign that reads "YE OLD ADULTS KEEP OUT!".
A bedroom with a bed, a dresser, a mirror, and a map on the wall.
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 758
SAR 996 total
includes taxes & fees
21 Oct - 22 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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Great Hotel and Staff. Big facility and clean rooms"
Cecilia 1-night trip
Posted 1 hour ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent
"The staff and management were very helpful, kind, considerate and very attentive mot only to our needs and comfort but also each guest that stayed. HIGHLY RECOMMEND HOLIDAY INNS AND I WILL ONLY STAYBAT HOLIDAY INNS WHEREVER I TRAVEL. Will be booking a stay at this hotel in 30 days for another 6 day stay"
richard 4-night trip
Posted 7 hours ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Loved my stay there, staff was amazing and the resort was beautiful"
Usomine 3-night trip
Posted 8 hours ago
The Grove Resort & Water Park Orlando
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"This property was amazing! The staff was friendly and helpful. Check in was smooth, the rooms were clean and spacious and well furnished. I loved sipping coffee on the balcony and people watching. We didn’t use the pool but it was inviting. The front desk was always staffed if you needed anything."
Louis 5-night trip
Posted 10 hours ago
Vacation Village Orlando, Celebration
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent
"Great location, close to everything. Large comfortable rooms and professional staff. Would definitely stay again!"
Susan 1-night trip
Posted 17 hours ago
Ramada by Wyndham Kissimmee Gateway

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.