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Check availability on Winter Haven Hotels with Pool

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 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 with a prominent entrance, multiple floors, and a parking lot.
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.

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.
Rp2.209.014
Rp2.474.095 total
includes taxes & fees
27 Oct - 28 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 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.
A modern bathroom with a bathtub, a large mirror, a vanity with a sink, and neatly arranged towels.

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.
Rp2.136.152
Rp2.392.489 total
includes taxes & fees
1 Nov - 2 Nov
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.
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.

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.
Rp2.750.872
Rp3.080.977 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott 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 lobby with a seating area, two elevators, and a large window with blinds.
A Holiday Inn hotel with a clear entrance, multiple flags, and a covered parking area.
A hotel reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.

4. 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.
Rp1.862.240
Rp2.085.708 total
includes taxes & fees
23 Nov - 24 Nov
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 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.
Rp2.422.720
Rp2.713.446 total
includes taxes & fees
8 Nov - 9 Nov
Staybridge Suites Winter Haven Auburndale by IHG
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 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.

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.
Rp2.597.192
Rp2.908.855 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 colorful play structure with a lighthouse in the background.
A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.
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
Rp3.597.920
Rp4.738.407 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 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.
Rp1.536.800
Rp1.721.217 total
includes taxes & fees
27 Oct - 28 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 marina with boats docked, surrounded by palm trees and a building with a covered area.
A wedding ceremony on a beach with a thatched gazebo and guests seated on chairs.

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.
Rp1.591.040
Rp1.781.965 total
includes taxes & fees
26 Oct - 27 Oct
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 room with wooden walls, a sofa, a television, a small table, and a stove.
A dock extending into a body of water with a grassy area in the foreground.

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.
Rp1.139.040
Rp1.275.725 total
includes taxes & fees
29 Oct - 30 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 Holiday Inn hotel with a clear entrance, multiple flags, and a covered parking area.
A hotel reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.
A modern lobby with a central seating area, a large chandelier, and a television mounted on the wall.
A hotel dining area with multiple tables and chairs, ceiling lights, and artwork on the walls.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
Rp1.862.240
Rp2.085.708 total
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn Winter Haven by IHG
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 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.

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
Rp2.209.014
Rp2.474.095 total
includes taxes & fees
27 Oct - 28 Oct
Best Western Plus Winter Haven Inn & Suites 
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.
A hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.
A swimming pool with lounge chairs and tables, surrounded by a fence and a building with a modern design.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
Rp2.136.152
Rp2.392.489 total
includes taxes & fees
1 Nov - 2 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 hotel room with a kitchenette, a dining area, and a bed.
A modern gym with exercise equipment, a television, and a view of the outdoors.
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
Rp2.422.720
Rp2.713.446 total
includes taxes & fees
8 Nov - 9 Nov
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 spacious indoor area with a bar, seating arrangements, and a large screen displaying content.
A modern reception area with wooden panel walls and two reception desks.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
Rp2.750.872
Rp3.080.977 total
includes taxes & fees
1 Nov - 2 Nov
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 reception desk with a sign reading "HOME 2 Suites by Hilton," a minibar, a refrigerator labeled "COLDER," and a snack shelf.
A hotel room with a desk, chair, sofa, ottoman, and a large window.

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
Rp2.597.192
Rp2.908.855 total
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton 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
Rp1.536.800
Rp1.721.217 total
includes taxes & fees
27 Oct - 28 Oct
Howard Johnson by Wyndham Winter Haven FL
A swimming pool area with people playing with building blocks.
A children's play area with a slide and climbing structures, a small lighthouse, and a building with a red and white striped roof.
A dining area with tables, chairs, and a colorful mural in the background.
A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
Rp3.597.920
Rp4.738.407 total
includes taxes & fees
13 Nov - 14 Nov
LEGOLAND Beach Retreat
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 dining area with tables and chairs, a central cart with dishes, and large windows with a view of greenery.
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
Rp3.869.120
Rp5.042.151 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

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

8/10 Good
"Resort was great, no bars or restraunt on site but very close. Room was pretty clea. Other the. The maid leaving the pull out couch open and no sheets in room for it Same with paper products. ?none left the b unit"
Hanna 2-night trip
Posted less than an hour ago
Vacation Village Orlando, Celebration
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Above my expectations! Great stay!"
Stephanie 4-night trip
Posted 3 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent
"Was perfect"
Victor 1-night trip
Posted 4 hours ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"The staff was so friendly and welcoming! The room was cozy and comfortable, and honestly, it felt like we never left home. We really enjoyed our stay and would definitely come back!"
Denzel 3-night trip
Posted 7 hours ago
Hilton Vacation Club Aqua Sol Orlando West

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.

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