A castle entrance with flags and banners, including a LEGO Kingdoms banner.

Search Hotels with Swimming Pool in Winter Haven

  • 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 Swimming Pool

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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.
₹11,542
₹12,927 total
includes taxes & fees
25 Oct - 26 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 hotel lobby with a reception desk, seating area, and a bar.
A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".

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.
₹11,161
₹12,501 total
includes taxes & fees
22 Nov - 23 Nov
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 hotel lobby with a dining area, bar, and seating arrangements.
A hotel lobby with a reception desk, seating area, and a large pillar.

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.
₹10,359
₹11,602 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Winter Haven by IHG
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 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.

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.
₹12,281
₹13,755 total
includes taxes & fees
25 Oct - 26 Oct
Staybridge Suites Winter Haven Auburndale by IHG
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.

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.
₹14,373
₹16,098 total
includes taxes & fees
28 Oct - 29 Oct
Courtyard by Marriott Winter Haven
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.
A hotel room with a desk, chair, sofa, ottoman, and a large window.
An outdoor seating area with sofas, chairs, and a fire pit.

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.
₹13,570
₹15,199 total
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton Winter Haven
A swimming pool area with people playing with building blocks.
A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.
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.

7. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
₹18,799
₹24,758 total
includes taxes & fees
13 Nov - 14 Nov
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 restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.

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.
₹8,030
₹8,993 total
includes taxes & fees
25 Oct - 26 Oct
Howard Johnson by Wyndham Winter Haven FL
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 waterfront property with a dock, lounge chairs, and palm trees.
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.
₹7,666
₹8,585 total
includes taxes & fees
22 Nov - 23 Nov
Lake Roy Beach Inn
A swimming pool with a fence, lounge chairs, and a palm tree.
A dock extending into a body of water with a grassy area in the foreground.
A cozy room with a wooden interior, a sofa, a small table, and a television.
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.
₹5,952
₹6,666 total
includes taxes & fees
23 Oct - 24 Oct
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 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
₹11,542
₹12,927 total
includes taxes & fees
25 Oct - 26 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 swimming pool with a poolside area, including lounge chairs and umbrellas, adjacent to a building with multiple windows and a brick facade.
A restaurant with a bar area, multiple dining tables, and chairs with patterned cushions.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
₹10,359
₹11,602 total
includes taxes & fees
25 Oct - 26 Oct
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 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.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
₹11,161
₹12,501 total
includes taxes & fees
22 Nov - 23 Nov
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 hotel room with a kitchenette, a dining area, and a bed.
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
₹12,281
₹13,755 total
includes taxes & fees
25 Oct - 26 Oct
Staybridge Suites Winter Haven Auburndale by IHG
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
₹14,373
₹16,098 total
includes taxes & fees
28 Oct - 29 Oct
Courtyard by Marriott Winter Haven
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 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.

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
₹13,570
₹15,199 total
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton Winter Haven
A swimming pool area with people playing with building blocks.
A dining area with tables, chairs, and a colorful mural 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.

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
₹18,799
₹24,758 total
includes taxes & fees
13 Nov - 14 Nov
LEGOLAND Beach Retreat
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 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
₹8,030
₹8,993 total
includes taxes & fees
25 Oct - 26 Oct
Howard Johnson by Wyndham Winter Haven FL
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 bedroom with a bed, a dresser, a mirror, and a map on the wall.

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
₹20,216
₹26,345 total
includes taxes & fees
17 Nov - 18 Nov
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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

8/10 Good
"I it would’ve been helpful if there was some sort of minimart on site so we could purchase sun block water chips etc"
Sandra 4-night trip
Posted 1 hour ago
Hilton Vacation Club Mystic Dunes Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Xx"
Edwin Junior 4-night trip
Posted 5 hours ago
The Grove Resort & Water Park Orlando
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Great overall experience"
Priscilla 3-night trip
Posted 6 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Amazing place to stay at. The villas were clean and beautiful. Lots of of room and space. There was a back deck, which was a nice hangout spot. The pool and waterpark were great. The kids enjoyed it very friendly staff and great location not far from Disney World. Our stay definitely felt like we were “ welcomed home.” would stay again!!!"
Storm 5-night trip
Posted 7 hours ago
Hilton Vacation Club Aqua Sol Orlando West
Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"No dan bien la información"
Maritza Nahir 2-night trip
Posted 22 hours ago
Delta Hotels by Marriott Orlando Celebration
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

8/10 Good
"Lots of people to assist you."
janet m 7-night trip
Posted 1 day ago
Vacation Village Orlando, Celebration
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

8/10 Good
"my room was very clean and everything worked well"
Patrick 1-night trip
Posted 4 days ago
Howard Johnson by Wyndham Winter Haven FL

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 8 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 has 8 hotels in Winter Haven for your poolside break.
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.

Explore a world of travel with Expedia