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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

Tonight
8 Oct - 9 Oct
Tomorrow
9 Oct - 10 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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 hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.
A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.
A modern hotel lobby with a central reception desk, multiple light fixtures, and a patterned wall.

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 489
SAR 548 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 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 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.

2. 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 428
SAR 479 total
includes taxes & fees
8 Nov - 9 Nov
Hampton Inn Winter Haven
A pool area with a wooden pergola, lounge chairs, and a view of the water.
A modern reception area with wooden panel walls and two reception desks.
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.

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
18 Oct - 19 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 dining area, a flat-screen TV, and a large window.
A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.
A modern hotel room with a kitchenette, a dining area, and a bed.

4. 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 518
SAR 580 total
includes taxes & fees
11 Oct - 12 Oct
Staybridge Suites Winter Haven Auburndale by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by a building with red and beige walls.
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.
An outdoor seating area with sofas, chairs, and a fire pit.

5. 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
18 Oct - 19 Oct
Home2 Suites By Hilton 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 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.
A hotel room with two beds, a desk, a television, and a door leading to another room.

6. 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 417
SAR 467 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Winter Haven by IHG
A swimming pool area with people playing with building blocks.
A colorful play structure with a lighthouse 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 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 634
SAR 858 total
includes taxes & fees
12 Oct - 13 Oct
LEGOLAND Beach Retreat
A circular pool with a metal ladder, surrounded by white lounge chairs and palm trees.
A bathtub with a white shower curtain, a grab bar, and a handheld showerhead.
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.

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
12 Oct - 13 Oct
Howard Johnson by Wyndham Winter Haven FL
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with a sink and countertop.
A bedroom with a bed, a nightstand, a window with blinds, a wall-mounted painting, and a door.
A two-story house with a garage, a covered porch, and a small front yard.
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 1,161
SAR 1,724 total
includes taxes & fees
21 Oct - 22 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 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 253
SAR 787 total
includes taxes & fees
11 Oct - 12 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 Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".
A hotel room with two beds, a large mirror, a wooden floor, and a view of the outdoors.
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.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
SAR 428
SAR 479 total
includes taxes & fees
8 Nov - 9 Nov
Hampton Inn Winter Haven
A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.
A modern hotel lobby with a central reception desk, multiple light fixtures, and a patterned wall.
A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.
A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
SAR 489
SAR 548 total
includes taxes & fees
18 Oct - 19 Oct
Best Western Plus Winter Haven Inn & Suites 
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.
A hotel reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.
A swimming pool with a poolside area, including lounge chairs and umbrellas, adjacent to a building with multiple windows and a brick facade.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
SAR 417
SAR 467 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Winter Haven by IHG
A hotel room with two beds, a TV, a microwave, and a desk with a lamp.
A conference room with tables and chairs, pink sashes, and a stage with drapes.
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.

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
SAR 287
SAR 322 total
includes taxes & fees
12 Oct - 13 Oct
Howard Johnson by Wyndham Winter Haven FL
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 hotel room with a kitchenette, a dining area, and a bed.
A modern kitchen with a wooden counter, coffee machines, and a Coca-Cola refrigerator.

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
SAR 518
SAR 580 total
includes taxes & fees
11 Oct - 12 Oct
Staybridge Suites Winter Haven Auburndale by IHG
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 reception desk with a sign reading "HOME 2 Suites by Hilton," a minibar, a refrigerator labeled "COLDER," and a snack shelf.
A modern kitchen with a central island, bar stools, and a refrigerator.

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
SAR 539
SAR 604 total
includes taxes & fees
18 Oct - 19 Oct
Home2 Suites By Hilton Winter Haven
An outdoor patio with a fire pit, wicker furniture, and a view of a lake.
A modern reception area with wooden panel walls and two reception desks.
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.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
SAR 539
SAR 604 total
includes taxes & fees
18 Oct - 19 Oct
Courtyard by Marriott Winter Haven
A kitchen area with a stone wall, wooden cabinets, a coffee station, and a staircase with a metal railing.
A compact hotel room with a kitchenette, a patterned sofa, and a lamp.
A reception area with a wooden floor, seating arrangements, and a reception desk.
A swimming pool with a white fence, outdoor seating, and a building with balconies in the background.

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.
Two LEGO figures in front of a colorful hotel building with a sign that reads "HOTEL".
A room with a stone wall, a fireplace, and a sign that reads "YE OLD ADULTS KEEP OUT!".

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
SAR 810
SAR 1,055 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

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

8/10 Good
"You won’t find a better deal with as close as it is to Disney"
James 1-night trip
Posted 4 hours ago
Ramada by Wyndham Kissimmee Gateway
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Great"
Oscar 2-night trip
Posted 5 hours ago
Holiday Inn Winter Haven by IHG
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent
"I had a great stay at this hotel. Everything was very clean, including the room and the sheets. The staff was excellent, friendly, and very helpful. The ladies working at the breakfast buffet were especially wonderful and made the experience even better. I really enjoyed my stay and would definitely recommend this hotel to anyone looking for a clean, comfortable place with great service."
Raydel 2-night trip
Posted 1 day ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Clean"
vik 5-night trip
Posted 1 day ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate

10/10 Excellent
"Lazy river & pool areas incredible will absolutely stay again."
Amber 3-night trip
Posted 4 days ago
Omni Orlando Resort at ChampionsGate

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.