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Check availability on Winter Haven Hotels with Pool

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

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 reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.
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.
฿3,726
฿4,173 total
includes taxes & fees
3 Sept - 4 Sept
Best Western Plus Winter Haven Inn & Suites 
A swimming pool with a brick building in the background, outdoor seating, and umbrellas.
A lobby with a seating area, two elevators, and a large potted plant.
A modern lobby with a seating area, a large chandelier, and a television mounted on the wall.

2. 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.
฿2,920
฿3,270 total
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Winter Haven by IHG
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 modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.
A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".

3. 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.
฿3,729
฿4,176 total
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn Winter Haven
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.

4. 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.
฿4,560
฿5,108 total
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Winter Haven
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.

5. 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.
฿2,778
฿3,112 total
includes taxes & fees
28 Aug - 29 Aug
Howard Johnson by Wyndham Winter Haven FL
A swimming pool with lounge chairs and tables, surrounded by a white building with a brick facade.
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.

6. 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.
฿3,762
฿4,214 total
includes taxes & fees
31 Aug - 1 Sept
Staybridge Suites Winter Haven Auburndale 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 brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.

7. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
฿5,807
฿7,785 total
includes taxes & fees
28 Aug - 29 Aug
LEGOLAND Beach Retreat
A swimming pool with lounge chairs and umbrellas, surrounded by a building with red and beige walls.
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.
A hotel room with a desk, chair, sofa, ottoman, and a large window.

8. 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.
฿4,530
฿5,073 total
includes taxes & fees
13 Sept - 14 Sept
Home2 Suites By Hilton Winter Haven
A lakeside view with a dock and a small building, likely a cabin or a house, surrounded by trees.
A building with a large water feature in front, surrounded by palm trees and a fence.
A marina with boats docked, surrounded by palm trees and a building with a covered area.
A waterfront property with a dock, lounge chairs, and palm trees.

9. Lake Roy Beach Inn

Lake Roy Beach Inn
Winter Haven
  • Lakeside pool paradise awaits with serene water views and complimentary loungers for ultimate relaxation.
฿2,781
฿3,114 total
includes taxes & fees
27 Aug - 28 Aug
Lake Roy Beach Inn
A swimming pool with a fence, lounge chairs, and a palm tree.
A compact room with wooden walls, a sofa, a television, a small table, and a stove.
A cozy room with a wooden interior, a sofa, a small table, and a television.
A compact kitchen with wooden cabinets, a refrigerator, a microwave, and a stove.

10. Lake Ida Beach Resort

Lake Ida Beach Resort
Winter Haven
  • Lakeside retreat with refreshing outdoor pool boasts loungers, umbrellas, and garden terrace for sunny Florida escapes.
฿2,324
฿2,603 total
includes taxes & fees
29 Aug - 30 Aug
Lake Ida Beach Resort
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 reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.
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
฿3,726
฿4,173 total
includes taxes & fees
3 Sept - 4 Sept
Best Western Plus Winter Haven Inn & Suites 
A modern lobby with a seating area, a large chandelier, and a television mounted on the wall.
A lobby with a seating area, two elevators, and a large potted plant.
A hotel reception area with a curved reception desk, a large chandelier, and a wall-mounted light fixture.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
฿2,920
฿3,270 total
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Winter Haven by IHG
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 swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.
A hotel lobby with a reception desk, seating area, and a bar.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
฿3,729
฿4,176 total
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn Winter Haven
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.
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.

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
฿3,762
฿4,214 total
includes taxes & fees
31 Aug - 1 Sept
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
฿4,560
฿5,108 total
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Winter Haven
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
฿2,778
฿3,112 total
includes taxes & fees
28 Aug - 29 Aug
Howard Johnson by Wyndham Winter Haven FL
An outdoor seating area with sofas, chairs, and a fire pit.
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.
A modern lounge area with green upholstered chairs, a herringbone-patterned floor, and a large window providing natural light.

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
฿4,530
฿5,073 total
includes taxes & fees
13 Sept - 14 Sept
Home2 Suites By Hilton Winter Haven
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 dining area with tables and chairs, a central cart with dishes, and large windows with a view of greenery.
A bedroom with a bed, a dresser, a mirror, and a map on the wall.

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
฿7,057
฿9,186 total
includes taxes & fees
16 Sept - 17 Sept
Legoland Florida Hotel
A kitchen area with a stone wall, wooden cabinets, a coffee station, and a staircase with a metal railing.
A swimming pool with a white fence, outdoor seating, and a building with balconies in the background.
A hotel room with a bed, two bedside tables, a desk, a chair, and a blue armchair.
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
฿2,642
฿2,959 total
includes taxes & fees
28 Aug - 29 Aug
Rodeway Inn & Suites Winter Haven Chain Of Lakes
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
"being staying in this property since 2017 no complains favorite so far very family friendly"
Ailyn 1-night trip
Posted 1 hour ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"1"
grisel 3-night trip
Posted 2 hours ago
Hilton Vacation Club Mystic Dunes Orlando
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

8/10 Good
"This was fine for a 1 night stay when taking my kid to college, nothing special but it gets the job done."
Joshua 1-night trip
Posted 5 hours ago
Howard Johnson by Wyndham Winter Haven FL
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Room was clean second time staying here no issues. Children loved the pool and water park awesome after a long day of exploring"
Mohinie 5-night trip
Posted 8 hours ago
Hilton Vacation Club Aqua Sol Orlando West
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent
"Everything was wonderful"
Mary 1-night trip
Posted 1 day ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Clean room and excellent customer service."
Johnathan 1-night trip
Posted 2 days ago
Holiday Inn Winter Haven by IHG

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 20 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.
What are some accommodation options 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's 20 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.

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