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Hotels with Swimming Pools in Winter Haven

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Check availability on Winter Haven Hotels with Swimming Pools

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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.
S$187
includes taxes & fees
18 Oct - 19 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 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".
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.
S$169
includes taxes & fees
8 Nov - 9 Nov
Hampton Inn Winter Haven
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 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.

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.
S$206
includes taxes & fees
18 Oct - 19 Oct
Courtyard by Marriott Winter Haven
A swimming pool with lounge chairs and tables, surrounded by a white building with a brick facade.
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.
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.
S$192
includes taxes & fees
18 Oct - 19 Oct
Staybridge Suites Winter Haven Auburndale by IHG
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 dining area with multiple tables and chairs, ceiling lights, and artwork on the walls.
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.

5. 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.
S$159
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Winter Haven by IHG
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 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.

6. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
S$293
includes taxes & fees
12 Oct - 13 Oct
LEGOLAND Beach Retreat
A swimming pool with lounge chairs and umbrellas, surrounded by a building with red and beige walls.
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.
An outdoor seating area with sofas, chairs, and a fire pit.

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.
S$218
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton 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 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.

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.
S$110
includes taxes & fees
18 Oct - 19 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 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.
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.
S$119
includes taxes & fees
11 Nov - 12 Nov
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 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.
S$101
includes taxes & fees
27 Oct - 28 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
S$187
includes taxes & fees
18 Oct - 19 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 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 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
S$169
includes taxes & fees
8 Nov - 9 Nov
Hampton Inn Winter Haven
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 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
S$206
includes taxes & fees
18 Oct - 19 Oct
Courtyard by Marriott Winter Haven
A hotel room with two beds, a desk, a television, and a door leading to another room.
A hotel dining area with multiple tables and chairs, ceiling lights, and artwork on the walls.
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 reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
S$159
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Winter Haven by IHG
A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.
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.
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
S$192
includes taxes & fees
18 Oct - 19 Oct
Staybridge Suites Winter Haven Auburndale by IHG
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 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
S$218
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites By Hilton 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 children's play area with a slide and climbing structures, a small lighthouse, and a building with a red and white striped roof.
A brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
S$293
includes taxes & fees
12 Oct - 13 Oct
LEGOLAND Beach Retreat
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 reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.
A restaurant with wooden walls, a neon sign, tables, chairs, a kitchen area, and a tiled floor.

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
S$110
includes taxes & fees
18 Oct - 19 Oct
Howard Johnson by Wyndham Winter Haven FL
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 compact hotel room with a kitchenette, a patterned sofa, and a lamp.
A motel with a sign reading "Rodeway Inn & Suites," a blue pickup truck parked in the lot, and a building with a blue roof.

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
S$116
includes taxes & fees
13 Oct - 14 Oct
Rodeway Inn & Suites Winter Haven Chain Of Lakes
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.
A room with a stone wall, a fireplace, and a sign that reads "YE OLD ADULTS KEEP OUT!".
A bedroom with a bed, a dresser, a mirror, and a map on the wall.

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
S$386
includes taxes & fees
27 Oct - 28 Oct
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

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent
"Great breakfast, room was clean, bed comfy and pillow selection good. Great location for Disney"
Genevieve L 2-night trip
Posted 1 hour ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent
"Great location l, I thought bed were comfortable..clean room weird smell but not too bad like a mold but I think it's more AC being on hot outside room was clean but a few minor issues that I didn't bring up to staff was tiny wormsbbut harmless and nothing to scary. They were escaping the heat. Pool was cool the lobby was cool"
Francisco 6-night trip
Posted 8 hours ago
Ramada by Wyndham Kissimmee Gateway
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent
"I’ve been staying at this property for the past 6 years and it’s always an amazing stay."
Stephany 1-night trip
Posted 9 hours ago
Holiday Inn Resort Kissimmee by the Parks by IHG
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Amazing time. Highly recommend for the full vaca experience, but with all the amenities of an apartment."
Jennifer 4-night trip
Posted 9 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
"We had a great stay and if we ever return to Florida we would stay here again. washer/dryer in the unit was very convenient. Kitchen had basic utensils, pan, bowls, plates, coffee maker, blender, toaster, refrigerator/freezer, stove, microwave, dishwasher. starter supply of detergent, dish soap, dishwasher tabs, coffee were given."
Jennifer 8-night trip
Posted 10 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Great spot for our volleyball tournament"
Michael 1-night trip
Posted 15 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 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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