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Winter Haven Hotels with Swimming Pool

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Check availability on Winter Haven Hotels with Swimming Pools

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sept
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

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 modern hotel with a prominent entrance, multiple floors, and a parking lot.
A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.

1. Best Western Plus Winter Haven Inn & SuitesĀ 

Best Western Plus Winter Haven Inn & SuitesĀ 
Winter Haven
  • Sun-soaked pool area creates perfect retreat near LEGOLAND Florida with loungers and umbrellas.
RM459
RM514 total
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Winter Haven Inn & SuitesĀ 
A swimming pool with a brick building in the background, outdoor seating, and umbrellas.
A hotel room with a bed, a desk with a lamp, a chair, a small table, and a nightstand with a phone.
A modern lobby with a central 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.
RM352
RM395 total
includes taxes & fees
27 Sept - 28 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 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".
A hotel lobby with a reception desk, seating area, and a bar.

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.
RM459
RM514 total
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn Winter Haven
A swimming pool with lounge chairs and tables, surrounded by a white building with a brick facade.
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.
A modern kitchen with a dining area, a flat-screen TV, and a large window.

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.
RM487
RM545 total
includes taxes & fees
6 Sept - 7 Sept
Staybridge Suites Winter Haven Auburndale by IHG
A pool area with a wooden pergola, lounge chairs, and a view of the water.
An outdoor patio with a fire pit, wicker furniture, and a view of a lake.
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.

5. 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.
RM578
RM648 total
includes taxes & fees
6 Sept - 7 Sept
Courtyard by Marriott Winter Haven
A circular pool with a metal ladder, surrounded by white lounge chairs and palm trees.
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.
A restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.

6. 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.
RM342
RM383 total
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Winter Haven FL
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
RM801
RM1,054 total
includes taxes & fees
11 Sept - 12 Sept
LEGOLAND Beach Retreat
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.
An outdoor seating area with sofas, chairs, and a fire pit.

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 LEGOLANDĀ® Florida.
RM558
RM625 total
includes taxes & fees
20 Sept - 21 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 marina with boats docked, surrounded by palm trees and a building with a covered area.
A building with a large water feature in front, surrounded by palm trees and a fence.
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.
RM338
RM379 total
includes taxes & fees
10 Sept - 11 Sept
Lake Roy Beach Inn
A swimming pool with a fence, lounge chairs, and a palm tree.
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.
A compact room with wooden walls, a sofa, a television, a small table, 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.
RM286
RM321 total
includes taxes & fees
8 Sept - 9 Sept
Lake Ida Beach Resort
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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 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.
A reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.

Best Western Plus Winter Haven Inn & SuitesĀ 

Best Western Plus Winter Haven Inn & SuitesĀ 
Winter Haven
RM459
RM514 total
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Winter Haven Inn & SuitesĀ 
A hotel room with a bed, a desk with a lamp, a chair, a small table, and a nightstand with a phone.
A modern lobby with a central seating area, a large chandelier, and a television mounted on the wall.
A gym with various exercise equipment, a clock on the wall, and a door.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
RM352
RM395 total
includes taxes & fees
27 Sept - 28 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 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.
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
RM459
RM514 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 kitchen with a wooden counter, coffee machines, and a Coca-Cola refrigerator.
A modern kitchen with a dining area, a flat-screen TV, and a large window.
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
RM487
RM545 total
includes taxes & fees
6 Sept - 7 Sept
Staybridge Suites Winter Haven Auburndale by IHG
A hotel room with two beds, a TV, a microwave, and a desk with a lamp.
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.
A conference room with tables set for an event, featuring pink and white tablecloths and chairs with pink sashes.

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
RM342
RM383 total
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Winter Haven FL
An outdoor patio with a fire pit, wicker furniture, and a view of a lake.
A spacious indoor area with a bar, seating arrangements, and a large screen displaying content.
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.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
RM578
RM648 total
includes taxes & fees
6 Sept - 7 Sept
Courtyard by Marriott Winter Haven
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 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
RM558
RM625 total
includes taxes & fees
20 Sept - 21 Sept
Home2 Suites By Hilton Winter Haven
A pool with floating building blocks and a colorful building with balconies in the background.
Two LEGO figures in front of a colorful hotel building with a sign that reads "HOTEL".
A bedroom with a bed, a dresser, a mirror, and a map on the wall.
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
RM869
RM1,131 total
includes taxes & fees
31 Aug - 1 Sept
Legoland Florida Hotel
A kitchen area with a stone wall, wooden cabinets, a coffee station, and a staircase with a metal railing.
A reception area with a wooden floor, seating arrangements, and a reception desk.
A hotel room with a bed, two bedside tables, a desk, a chair, and a blue armchair.
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
RM342
RM383 total
includes taxes & fees
31 Aug - 1 Sept
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.
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Top Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

8/10 Good
"Our room weā€™re missing the pot and pan that seems to been pictured so we had to buy our own, and if anything the rooms could use more trash cans especially in the bathrooms"
Mariella 3-night trip
Posted 12 hours ago
The Grove Resort & Water Park Orlando
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Staff is friendly, close to many things"
Chris 1-night trip
Posted 14 hours 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 LEGOLANDĀ® 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 LEGOLANDĀ® 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 LEGOLANDĀ® Florida while you're in Winter Haven. Make a point to visit attractions such as The Circle B Bar Reserve and Indigo's Family Fun Center. 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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