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

Winter Haven Hotels with Swimming Pool

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Check availability on Winter Haven Hotels with Swimming Pools

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 reception area with a modern design, featuring a counter, a seating area, and a wall with a unique pattern.
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.
RM499
RM559 total
includes taxes & fees
18 Oct - 19 Oct
Best Western Plus Winter Haven Inn & Suites 
A pool area with a wooden pergola, lounge chairs, and a view of the water.
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.
A modern reception area with wooden panel walls and two reception desks.

2. 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.
RM690
RM773 total
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 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.

3. 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.
RM547
RM613 total
includes taxes & fees
18 Oct - 19 Oct
Staybridge Suites Winter Haven Auburndale by IHG
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 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".

4. 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.
RM483
RM541 total
includes taxes & fees
8 Nov - 9 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 reception area with a curved reception desk, a large chandelier, and a wall-mounted sign.
A bathroom with a shower, a toilet, a sink, and a mirror.
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.
RM449
RM503 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Winter Haven by IHG
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.
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.
RM622
RM696 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 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 brightly colored building with a white picket fence, numbered doors, and a surfboard decoration.

7. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
RM854
RM1,116 total
includes taxes & fees
30 Oct - 31 Oct
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 bathtub with a white shower curtain, a grab bar, and a handheld showerhead.

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.
RM312
RM350 total
includes taxes & fees
26 Oct - 27 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 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.

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.
RM359
RM403 total
includes taxes & fees
15 Oct - 16 Oct
Lake Roy Beach Inn
A dark brown leather sectional sofa with multiple cushions, a carpeted floor, and two wall-mounted dog portraits.
A view through a glass door of a backyard with a patio table and chairs, a grassy area, and a building in the background.
A laundry area with two washers and dryers, a mop, and a basket.
A dining area with a large table, chairs, and a wall clock.

10. 10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney

10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
Winter Haven
RM1,254
RM1,861 total
includes taxes & fees
26 Oct - 27 Oct
10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
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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 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 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
RM499
RM559 total
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 room with two beds, a large mirror, a wooden floor, and a view of the outdoors.
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
RM483
RM541 total
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 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.
A modern reception area with wooden panel walls and two reception desks.

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
RM690
RM773 total
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 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.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
RM449
RM503 total
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 dining area, a flat-screen TV, and a large window.
A modern kitchen with a wooden counter, coffee machines, and a Coca-Cola refrigerator.
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.

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
RM547
RM613 total
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 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.
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
RM622
RM696 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 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 dining area with tables, chairs, and a colorful mural in the background.

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
RM854
RM1,116 total
includes taxes & fees
30 Oct - 31 Oct
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 conference room with tables and chairs, pink sashes, and a stage with drapes.

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
RM312
RM350 total
includes taxes & fees
26 Oct - 27 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 compact hotel room with a kitchenette, a patterned sofa, and a lamp.
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
RM330
RM369 total
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 room with a stone wall, a fireplace, and a sign that reads "YE OLD ADULTS KEEP OUT!".
A dining area with tables and chairs, a central cart with dishes, and large windows with a view of greenery.
A bedroom with a bed, a dresser, a mirror, and a map on the wall.

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
RM956
RM1,231 total
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.
View all properties

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 2 hours 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 14 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 17 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 17 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 17 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.

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