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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
Sep 16 - Sep 17
Tomorrow
Sep 17 - Sep 18
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

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 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.

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.
₩166,539
₩186,524 total
includes taxes & fees
Sep 20 - Sep 21
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 modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.
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.

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.
₩155,362
₩174,005 total
includes taxes & fees
Oct 4 - Oct 5
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 a desk, chair, sofa, and a painting on the wall.
A bathroom with a shower, a toilet, a sink, and a mirror.
A hotel lobby with a dining area, bar, and seating arrangements.

3. 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.
₩143,121
₩160,296 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Winter Haven 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 Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.
A modern reception area with wooden panel walls and two reception desks.

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.
₩195,804
₩219,300 total
includes taxes & fees
Sep 27 - Sep 28
Courtyard by Marriott Winter Haven
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 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.

5. 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.
₩164,930
₩184,721 total
includes taxes & fees
Sep 20 - Sep 21
Staybridge Suites Winter Haven Auburndale by IHG
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 restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.
A hotel room with two beds, a TV, a microwave, and a desk with a lamp.

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.
₩104,274
₩116,787 total
includes taxes & fees
Sep 20 - Sep 21
Howard Johnson by Wyndham Winter Haven FL
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.

7. 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.
₩177,716
₩199,042 total
includes taxes & fees
Sep 27 - Sep 28
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 brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.
A colorful play structure with a lighthouse in the background.

8. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
₩230,562
₩311,661 total
includes taxes & fees
Oct 12 - Oct 13
LEGOLAND Beach Retreat
A lakeside view with a dock and a small building, likely a cabin or a house, surrounded by trees.
A waterfront property with a dock, lounge chairs, and palm trees.
A wedding ceremony on a beach with a thatched gazebo and guests seated on chairs.
A marina with boats docked, surrounded by palm trees and a building with a covered area.

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.
₩119,949
₩134,344 total
includes taxes & fees
Sep 18 - Sep 19
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 compact kitchen with wooden cabinets, a refrigerator, a microwave, and a stove.
A cozy room with a wooden interior, a sofa, a small table, and a television.

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.
₩96,914
₩108,543 total
includes taxes & fees
Sep 18 - Sep 19
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 swimming pool, outdoor seating, and a well-lit facade.
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
₩166,539
₩186,524 total
includes taxes & fees
Sep 20 - Sep 21
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 lobby with a dining area, bar, and seating arrangements.
A hotel room with a desk, chair, sofa, and a painting on the wall.
A Holiday Inn hotel with a clear entrance, multiple flags, and a covered parking area.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
₩143,121
₩160,296 total
includes taxes & fees
Sep 20 - Sep 21
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 conference room with tables set for an event, featuring pink and white tablecloths and chairs with pink sashes.
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
₩104,274
₩116,787 total
includes taxes & fees
Sep 20 - Sep 21
Howard Johnson by Wyndham Winter Haven FL
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 room with two beds, a large mirror, a wooden floor, and a view of the outdoors.
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
₩155,362
₩174,005 total
includes taxes & fees
Oct 4 - Oct 5
Hampton Inn 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 dining area with tables, chairs, and a colorful mural in the background.
A children's play area with a slide and climbing structures, a small lighthouse, and a building with a red and white striped roof.

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
₩230,562
₩311,661 total
includes taxes & fees
Oct 12 - Oct 13
LEGOLAND Beach Retreat
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 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.

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
₩164,930
₩184,721 total
includes taxes & fees
Sep 20 - Sep 21
Staybridge Suites Winter Haven Auburndale by IHG
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.
A modern reception area with wooden panel walls and two reception desks.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
₩195,804
₩219,300 total
includes taxes & fees
Sep 27 - Sep 28
Courtyard by Marriott Winter Haven
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
₩177,716
₩199,042 total
includes taxes & fees
Sep 27 - Sep 28
Home2 Suites By Hilton Winter Haven
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 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.

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
₩110,067
₩123,289 total
includes taxes & fees
Sep 19 - Sep 20
Rodeway Inn & Suites Winter Haven Chain Of Lakes
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 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.

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
₩271,113
₩357,078 total
includes taxes & fees
Sep 22 - Sep 23
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Great place my boys loved the water park"
Smyrna 1-night trip
Posted 5 hours ago
The Grove Resort & Water Park Orlando
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

10/10 Excellent
"Na"
Deanna 1-night trip
Posted 8 hours ago
Howard Johnson by Wyndham Winter Haven FL
Quality Inn & Suites By the Parks

Quality Inn & Suites By the Parks

10/10 Excellent
"Rooms were clean, beds super comfortable, nice cold air conditioner, breakfast good, and staff absolutely wonderful."
Jacqueline 2-night trip
Posted 1 day ago
Quality Inn & Suites By the Parks
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"we had a good stay , everything was good"
Maylin 3-night trip
Posted 1 day 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 20 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'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 like LEGOLAND® Florida while you're in Winter Haven. Make a point to visit attractions like Inman Park 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 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.

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