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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
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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 reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.
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.

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.
NT$4,164
NT$4,664 total
includes taxes & fees
Oct 13 - Oct 14
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 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".

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.
NT$3,772
NT$4,225 total
includes taxes & fees
Nov 8 - Nov 9
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.
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.

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.
NT$4,588
NT$5,139 total
includes taxes & fees
Oct 18 - Oct 19
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 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 bathroom with a shower, a toilet, a sink, and a mirror.

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.
NT$3,544
NT$3,969 total
includes taxes & fees
Nov 8 - Nov 9
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 dining area, a flat-screen TV, and a large window.

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.
NT$4,280
NT$4,793 total
includes taxes & fees
Oct 18 - Oct 19
Staybridge Suites Winter Haven Auburndale by IHG
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.
An outdoor seating area with sofas, chairs, and a fire pit.
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.
NT$4,588
NT$5,139 total
includes taxes & fees
Oct 18 - Oct 19
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 row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.
A colorful play structure with a lighthouse in the background.

7. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
NT$5,395
NT$7,294 total
includes taxes & fees
Oct 12 - Oct 13
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 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.

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.
NT$2,442
NT$2,735 total
includes taxes & fees
Oct 18 - Oct 19
Howard Johnson by Wyndham Winter Haven FL
A swimming pool with a white fence, outdoor seating, and a building with balconies in the background.
A reception area with a wooden floor, seating arrangements, and a reception desk.
A kitchen area with a stone wall, wooden cabinets, a coffee station, and a staircase with a metal railing.
A hotel room with a bed, two bedside tables, a desk, a chair, and a blue armchair.

9. Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
  • Splash into fun at this lakeside motel with a sun-soaked pool just minutes from LEGOLAND Florida.
NT$2,578
NT$2,888 total
includes taxes & fees
Oct 13 - Oct 14
Rodeway Inn & Suites Winter Haven Chain Of Lakes
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.

10. Lake Roy Beach Inn

Lake Roy Beach Inn
Winter Haven
  • Lakeside pool paradise awaits with serene water views and complimentary loungers for ultimate relaxation.
NT$2,809
NT$3,147 total
includes taxes & fees
Oct 11 - Oct 12
Lake Roy Beach Inn
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 reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.
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.

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
NT$4,164
NT$4,664 total
includes taxes & fees
Oct 13 - Oct 14
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 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.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
NT$3,772
NT$4,225 total
includes taxes & fees
Nov 8 - Nov 9
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 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.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
NT$4,588
NT$5,139 total
includes taxes & fees
Oct 18 - Oct 19
Courtyard by Marriott Winter Haven
A hotel room with two beds, a desk, a television, and a door leading to another room.
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.
A hotel room with a desk, chair, sofa, and a painting on the wall.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
NT$3,544
NT$3,969 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Winter Haven by IHG
A coffee station with a display case of pastries, coffee machines, and a coffee dispenser.
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 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
NT$4,280
NT$4,793 total
includes taxes & fees
Oct 18 - Oct 19
Staybridge Suites Winter Haven Auburndale by IHG
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.
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
NT$4,588
NT$5,139 total
includes taxes & fees
Oct 18 - Oct 19
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 brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.
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
NT$5,395
NT$7,294 total
includes taxes & fees
Oct 12 - Oct 13
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 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
NT$2,442
NT$2,735 total
includes taxes & fees
Oct 18 - Oct 19
Howard Johnson by Wyndham Winter Haven FL
A kitchen area with a stone wall, wooden cabinets, a coffee station, and a staircase with a metal railing.
A compact hotel room with a kitchenette, a patterned sofa, and a lamp.
A hotel room with a bed, two bedside tables, a desk, a chair, and a blue armchair.
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
NT$2,578
NT$2,888 total
includes taxes & fees
Oct 13 - Oct 14
Rodeway Inn & Suites Winter Haven Chain Of Lakes
A pool with floating building blocks and a colorful building with balconies in the background.
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!".
Two LEGO figures in front of a colorful hotel building with a sign that reads "HOTEL".

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
NT$7,471
NT$9,619 total
includes taxes & fees
Oct 27 - Oct 28
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
"The property and room were beautiful and well maintained. The kids had a great time. So much for them to do. The pools are amazing."
PATRICIA DENISE 3-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
"Our 2 room/2 bath condo was excellent. We were on the 6th floor and had a great view. The lazy river was very relaxing. We thoroughly enjoyed our stay."
Natalie 4-night trip
Posted 10 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Large facility with great pool."
RONALD 2-night trip
Posted 12 hours ago
Hilton Vacation Club Mystic Dunes Orlando
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Staff was amazing very helpful. Area was really nice."
Nicole 3-night trip
Posted 18 hours ago
Hilton Vacation Club Aqua Sol Orlando West
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent
"Pool was close at night and break fast too expensive"
Glorymar 1-night trip
Posted 19 hours ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate

10/10 Excellent
"It was great"
Josh 1-night trip
Posted 1 day ago
Omni Orlando Resort at ChampionsGate
Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"Great stay. Thank you."
Alfonzia 2-night trip
Posted 2 days ago
Delta Hotels by Marriott Orlando Celebration
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Great"
Oscar 2-night trip
Posted 2 days ago
Holiday Inn Winter Haven by IHG

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