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

Find Hotels with a Pool in Winter Haven, FL from CA $97

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Haven Hotels with a Pool

Tonight
Sep 27 - Sep 28
Tomorrow
Sep 28 - Sep 29
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

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 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.

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.
CA $173
CA $194 total
includes taxes & fees
Sep 29 - Sep 30
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 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".

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.
CA $138
CA $155 total
includes taxes & fees
Oct 4 - Oct 5
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 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.
A conference room with a long table, chairs, a television, and a carpeted floor.

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.
CA $156
CA $174 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Winter Haven by IHG
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 Courtyard by Marriott hotel with a modern design, featuring a covered entrance and a landscaped area with palm trees.

4. 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.
CA $209
CA $234 total
includes taxes & fees
Oct 4 - Oct 5
Courtyard by Marriott Winter Haven
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 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.

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.
CA $108
CA $121 total
includes taxes & fees
Oct 1 - Oct 2
Howard Johnson by Wyndham Winter Haven FL
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.

6. 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.
CA $184
CA $206 total
includes taxes & fees
Oct 4 - Oct 5
Staybridge Suites Winter Haven Auburndale by IHG
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 colorful LEGO-themed beach retreat sign with a beach house and a gas station 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
CA $227
CA $310 total
includes taxes & fees
Oct 12 - Oct 13
LEGOLAND Beach Retreat
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.
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.

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.
CA $196
CA $219 total
includes taxes & fees
Oct 4 - Oct 5
Home2 Suites By Hilton Winter Haven
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 building with a large water feature in front, surrounded by palm trees and a fence.
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.
CA $124
CA $139 total
includes taxes & fees
Sep 28 - Sep 29
Lake Roy Beach Inn
A swimming pool with a fence, lounge chairs, and a palm tree.
A compact room with wooden walls, a sofa, a television, a small table, and a stove.
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.
CA $86
CA $97 total
includes taxes & fees
Oct 13 - Oct 14
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
Water park
5 stars

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 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.

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
CA $173
CA $194 total
includes taxes & fees
Sep 29 - Sep 30
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 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.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
CA $138
CA $155 total
includes taxes & fees
Oct 4 - Oct 5
Hampton Inn Winter Haven
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 hotel lobby with a reception desk, seating area, and a large pillar.
A modern lobby with a central seating area, a large chandelier, and a television mounted on the wall.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
CA $156
CA $174 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Winter Haven by IHG
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 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
CA $209
CA $234 total
includes taxes & fees
Oct 4 - Oct 5
Courtyard by Marriott Winter Haven
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 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
CA $184
CA $206 total
includes taxes & fees
Oct 4 - Oct 5
Staybridge Suites Winter Haven Auburndale by IHG
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 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.

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
CA $108
CA $121 total
includes taxes & fees
Oct 1 - Oct 2
Howard Johnson by Wyndham Winter Haven FL
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 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.

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
CA $196
CA $219 total
includes taxes & fees
Oct 4 - Oct 5
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 dining area with tables, chairs, and a colorful mural in the background.

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
CA $227
CA $310 total
includes taxes & fees
Oct 12 - Oct 13
LEGOLAND Beach Retreat
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
CA $114
CA $128 total
includes taxes & fees
Sep 29 - Sep 30
Rodeway Inn & Suites Winter Haven Chain Of Lakes
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 bedroom with a bed, a dresser, a mirror, and a map on the wall.
A dining area with tables and chairs, a central cart with dishes, and large windows with a view of greenery.

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
CA $282
CA $316 total
includes taxes & fees
Oct 12 - Oct 13
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
"No"
Leah 7-night trip
Posted 2 hours ago
The Grove Resort & Water Park Orlando
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"!"
Kellen 2-night trip
Posted 8 hours ago
Vacation Village Orlando, Celebration
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Great room"
Marina 1-night trip
Posted 10 hours ago
Hilton Vacation Club Mystic Dunes Orlando
Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"Room was very clean and updated, with a refrigerator witch was nice to have cold drinks in the room. The pool area was great with a tiki bar with good options from beer and wine, to some good fruity cocktails."
Jeff 1-night trip
Posted 14 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
"Everything was 👍👍👍"
Wikash 5-night trip
Posted 16 hours ago
Hilton Vacation Club Aqua Sol Orlando West

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 Inman Park and Indigo's Family Fun Center. 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.

Explore a world of travel with Expedia