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

Winter Haven Hotel Guide - Hotels with Pool in Winter Haven, Florida

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Check availability on Winter Haven Hotels with Pool

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
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 with a prominent entrance, multiple floors, and a parking lot.
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.

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.
€122
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 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".
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.
€118
includes taxes & fees
25 Oct - 26 Oct
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 hotel reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.
A hotel room with two beds, a desk, a television, and a door leading to another room.

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.
€110
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.
€135
includes taxes & fees
18 Oct - 19 Oct
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.

5. 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.
€77
includes taxes & fees
19 Oct - 20 Oct
Howard Johnson by Wyndham Winter Haven FL
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 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.

6. 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.
€169
includes taxes & fees
18 Oct - 19 Oct
Courtyard by Marriott Winter Haven
A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.
A cozy room with two armchairs, each with a cushion featuring a fish design. There is a small table with two lamps and a couple of potted plants. A decorative sign on the wall reads "hello."
A residential property with a paved driveway, a lawn, and mature trees with hanging moss.
A room with two beds, a small rug, and a staircase.

7. The Russell Lake House

The Russell Lake House
Winter Haven
€194
includes taxes & fees
15 Oct - 16 Oct
The Russell Lake House
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 kitchen with a central island, bar stools, and a refrigerator.
A hotel room with a desk, chair, sofa, ottoman, and a large window.

8. 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.
€152
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 brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.
A colorful play structure with a lighthouse in the background.

9. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
€244
includes taxes & fees
6 Nov - 7 Nov
LEGOLAND Beach Retreat
A lakeside view with a dock and a small building, likely a cabin or a house, surrounded by trees.
A wedding ceremony on a beach with a thatched gazebo and guests seated on chairs.
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.

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.
€88
includes taxes & fees
15 Oct - 16 Oct
Lake Roy Beach Inn
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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 with a prominent entrance, multiple floors, and a parking lot.
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.

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
€122
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 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 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
€118
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Winter Haven
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 modern hotel lobby with a long reception desk, bar area, and seating arrangement.
A modern reception area with wooden panel walls and two reception desks.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
€169
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 reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.
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.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
€110
includes taxes & fees
25 Oct - 26 Oct
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 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
€135
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 modern kitchen with a central island, bar stools, and a refrigerator.
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.

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
€152
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 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
€244
includes taxes & fees
6 Nov - 7 Nov
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 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
€77
includes taxes & fees
19 Oct - 20 Oct
Howard Johnson by Wyndham Winter Haven FL
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.
A hotel room with a television, two armchairs, a small table, and a patterned carpet.
A room with a small kitchenette, a blue ironing board, a trash bin, and a metal rack with black straps.

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
€81
includes taxes & fees
17 Oct - 18 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.
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
€235
includes taxes & fees
20 Oct - 21 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.
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Top Winter Haven Hotel Reviews

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

10/10 Excellent
"Room was clean and it was the right price."
Selena 1-night trip
Posted 1 hour ago
Howard Johnson by Wyndham Winter Haven FL
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

8/10 Good
"Everything was awesome! When we arrived our room was no longer available but we got an upgrade, only reason I gave it a 4/5 is because I forgot an item, Called them 2 hours after check it out, they said they will call back but never did, called twice."
Payman 7-night trip
Posted 13 hours ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"The room was excellent with pool views. The breakfast was delicious. The entire property was nice and I definitely enjoyed the pool, rum shack bar and fitness center."
Hector 5-night trip
Posted 16 hours ago
Delta Hotels by Marriott Orlando Celebration
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Very nice place to spend the weekend with young children"
WAIITI 1-night trip
Posted 16 hours ago
Hilton Vacation Club Aqua Sol Orlando West
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"We’ve stayed at Mystic Dunes in Orlando twice and have really enjoyed our stays! The condos are spacious, the grounds are clean and well maintained, and there are three pools on the property. The location is also great—close to Disney, with a Walmart just around the corner, which is super convenient. The kitchens are stocked with everything you need, including pots, pans, cleaning supplies, soaps, and more. The kitchens are on the smaller side and can feel a little cramped, but it was nice having everything available. There is also a washer and dryer in the condo, which is a big plus. One thing to keep in mind when booking is that the condos have a maximum of two bedrooms per condo. Some units have a shared entryway with two separate condo doors, so what may appear like a larger setup can actually be two separate condos. If you’re traveling with small children or need three bedrooms together, this is definitely something to check ahead of time. There is one pool bar that serves food and drinks, but if you aren’t staying close by, you’ll definitely want a car to get around. There is no hot tub, which would be a nice addition. Overall, we’ve had two enjoyable stays and would definitely consider staying at Mystic Dunes again. It’s a comfortable, convenient option for a Disney-area trip, especially if you like having a little more space than a typical hotel room!"
Christiana 3-night trip
Posted 16 hours ago
Hilton Vacation Club Mystic Dunes Orlando

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.