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

Winter Haven Hotel with Pool

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Check availability on Winter Haven Hotel with Pool

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 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 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.
HK$958
HK$1,074 total
includes taxes & fees
29 Sept - 30 Sept
Best Western Plus Winter Haven Inn & Suites 
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 lobby with a dining area, bar, and seating arrangements.
A hotel room with two beds, a desk, a television, and a door leading to another room.
A bathroom with a shower, a toilet, a sink, and a mirror.

2. 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.
HK$863
HK$967 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Winter Haven 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 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 hotel lobby with a seating area featuring blue patterned chairs, a wooden coffee table, and a sofa.

3. 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.
HK$894
HK$1,001 total
includes taxes & fees
4 Oct - 5 Oct
Hampton Inn Winter Haven
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.
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.

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.
HK$1,194
HK$1,337 total
includes taxes & fees
4 Oct - 5 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 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.
HK$1,020
HK$1,142 total
includes taxes & fees
27 Sept - 28 Sept
Staybridge Suites Winter Haven Auburndale by IHG
A circular pool with a metal ladder, surrounded by white lounge chairs and palm trees.
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 reception area with a reception desk, a potted plant, a fire extinguisher, and a dining area with chairs and tables.

6. 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.
HK$600
HK$672 total
includes taxes & fees
1 Oct - 2 Oct
Howard Johnson by Wyndham Winter Haven FL
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 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.

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.
HK$1,087
HK$1,218 total
includes taxes & fees
29 Sept - 30 Sept
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.

8. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
HK$1,260
HK$1,719 total
includes taxes & fees
12 Oct - 13 Oct
LEGOLAND Beach Retreat
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.
HK$620
HK$694 total
includes taxes & fees
22 Oct - 23 Oct
Lake Roy Beach Inn
A swimming pool with a fence, lounge chairs, and a palm tree.
A dock extending into a body of water with a grassy area in the foreground.
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.

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.
HK$558
HK$625 total
includes taxes & fees
23 Sept - 24 Sept
Lake Ida Beach Resort
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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 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
HK$958
HK$1,074 total
includes taxes & fees
29 Sept - 30 Sept
Best Western Plus Winter Haven Inn & Suites 
A hotel room with two beds, a desk, a television, and a door leading to another room.
A Holiday Inn hotel with a clear entrance, multiple flags, and a covered parking area.
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.

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
HK$863
HK$967 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Winter Haven by IHG
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 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
HK$1,194
HK$1,337 total
includes taxes & fees
4 Oct - 5 Oct
Courtyard by Marriott Winter Haven
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 room with two beds, a large mirror, a wooden floor, and a view of the outdoors.

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
HK$894
HK$1,001 total
includes taxes & fees
4 Oct - 5 Oct
Hampton Inn 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 dining area, a flat-screen TV, and a large window.
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
HK$1,020
HK$1,142 total
includes taxes & fees
27 Sept - 28 Sept
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 modern lounge area with green upholstered chairs, a herringbone-patterned floor, and a large window providing natural light.
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
HK$1,087
HK$1,218 total
includes taxes & fees
29 Sept - 30 Sept
Home2 Suites By Hilton Winter Haven
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.
A conference room with tables set for an event, featuring pink and white tablecloths and chairs with pink sashes.
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
HK$600
HK$672 total
includes taxes & fees
1 Oct - 2 Oct
Howard Johnson by Wyndham Winter Haven FL
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
HK$1,260
HK$1,719 total
includes taxes & fees
12 Oct - 13 Oct
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
HK$634
HK$710 total
includes taxes & fees
25 Sept - 26 Sept
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 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!".

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
HK$1,560
HK$2,055 total
includes taxes & fees
23 Sept - 24 Sept
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 Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Amazing time during my stay"
James 4-night trip
Posted 3 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

8/10 Good
"The apartments are great! However, the halls and rugs need to be cleaned and washed as there is a strong smell coming from them on every floor."
Summer 2-night trip
Posted 4 hours ago
The Grove Resort & Water Park Orlando
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Super clean"
Alberto 2-night trip
Posted 5 hours ago
Hilton Vacation Club Aqua Sol Orlando West
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Clean room and well maintained property. Convenient to where we had an event."
Timothy Duane 2-night trip
Posted 23 hours ago
Holiday Inn Winter Haven by IHG
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

8/10 Good
"Todo estuvo bien"
Yuris L 1-night trip
Posted 3 days ago
Howard Johnson by Wyndham Winter Haven FL

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 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 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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