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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
15 Sep - 16 Sep
Tomorrow
16 Sep - 17 Sep
This weekend
18 Sep - 20 Sep
Next weekend
25 Sep - 27 Sep

Our top choices for Winter Haven hotels with a pool

Outdoor pool, pool umbrellas, sun loungers
Exterior
Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room) | Desk, laptop workspace, blackout drapes, iron/ironing board
Reception

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.
SAR 459
SAR 514 total
includes taxes & fees
20 Sep - 21 Sep
Best Western Plus Winter Haven Inn & Suites 
Outdoor pool, pool umbrellas, sun loungers
Exterior
Reception
Combined shower/tub, free toiletries, hair dryer, towels

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.
SAR 428
SAR 479 total
includes taxes & fees
27 Sep - 28 Sep
Hampton Inn Winter Haven
Outdoor pool, open 8:00 AM to 9:00 PM, sun loungers
Restaurant
Suite | Desk, blackout drapes, iron/ironing board, cribs (free)
Eco-friendly toiletries, hair dryer, towels, soap

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.
SAR 394
SAR 442 total
includes taxes & fees
20 Sep - 21 Sep
Holiday Inn Winter Haven by IHG
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
Lobby
Exterior
Property amenity

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.
SAR 540
SAR 604 total
includes taxes & fees
27 Sep - 28 Sep
Courtyard by Marriott Winter Haven
Outdoor pool, pool umbrellas, sun loungers
Exterior
Free daily continental breakfast
Premium bedding, down comforters, pillowtop beds, blackout drapes

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.
SAR 454
SAR 509 total
includes taxes & fees
20 Sep - 21 Sep
Staybridge Suites Winter Haven Auburndale by IHG
Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers
Free daily continental breakfast
Combined shower/tub, eco-friendly toiletries, hair dryer, towels
Blackout drapes, iron/ironing board, cribs (free)

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.
SAR 287
SAR 322 total
includes taxes & fees
20 Sep - 21 Sep
Howard Johnson by Wyndham Winter Haven FL
Seasonal outdoor pool
Lobby
Terrace/patio
Free daily buffet breakfast

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.
SAR 490
SAR 548 total
includes taxes & fees
27 Sep - 28 Sep
Home2 Suites By Hilton Winter Haven
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Children's play area - outdoor
Exterior
Children's area

8. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
SAR 540
SAR 752 total
includes taxes & fees
12 Oct - 13 Oct
LEGOLAND Beach Retreat
Property grounds
Exterior
Exterior
Exterior

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.
SAR 331
SAR 370 total
includes taxes & fees
16 Sep - 17 Sep
Lake Roy Beach Inn
Outdoor pool, pool umbrellas, sun loungers
Standard Room, 1 Queen Bed, Non Smoking | Private kitchenette | Coffee/tea maker, fridge, microwave, oven
Quadruple Room, Non Smoking, Lake View | Living area | TV
Lake

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.
SAR 262
SAR 293 total
includes taxes & fees
23 Sep - 24 Sep
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
5 stars
Water park

Hotels with pools and free breakfast in Winter Haven

Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room) | Desk, laptop workspace, blackout drapes, iron/ironing board
Exterior
Free daily full breakfast
Reception

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
SAR 459
SAR 514 total
includes taxes & fees
20 Sep - 21 Sep
Best Western Plus Winter Haven Inn & Suites 
Desk, blackout drapes, iron/ironing board, cribs (free)
Exterior
Restaurant
Suite | Desk, blackout drapes, iron/ironing board, cribs (free)

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
SAR 394
SAR 442 total
includes taxes & fees
20 Sep - 21 Sep
Holiday Inn Winter Haven by IHG
Blackout drapes, iron/ironing board, cribs (free)
Reception
Reception
Interior entrance

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
SAR 287
SAR 322 total
includes taxes & fees
20 Sep - 21 Sep
Howard Johnson by Wyndham Winter Haven FL
Exterior
Reception
Lobby
Outdoor pool, pool umbrellas, sun loungers

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
SAR 428
SAR 479 total
includes taxes & fees
27 Sep - 28 Sep
Hampton Inn Winter Haven
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Children's play area - outdoor
Restaurant
Exterior

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
SAR 540
SAR 752 total
includes taxes & fees
12 Oct - 13 Oct
LEGOLAND Beach Retreat
Exterior
Studio Suite, 2 Queen Beds, Kitchen, Lake View | Premium bedding, down comforters, pillowtop beds, blackout drapes
Premium bedding, down comforters, pillowtop beds, blackout drapes
Exterior

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
SAR 454
SAR 509 total
includes taxes & fees
20 Sep - 21 Sep
Staybridge Suites Winter Haven Auburndale by IHG
Property amenity
Breakfast and dinner served
Exterior
Lobby

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
SAR 540
SAR 604 total
includes taxes & fees
27 Sep - 28 Sep
Courtyard by Marriott Winter Haven
Terrace/patio
Reception
Free daily buffet breakfast
LED TV, Netflix, streaming services

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
SAR 490
SAR 548 total
includes taxes & fees
27 Sep - 28 Sep
Home2 Suites By Hilton Winter Haven
Free daily continental breakfast
Lobby
Outdoor pool
Suite, 1 King Bed, Non Smoking | Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
SAR 303
SAR 340 total
includes taxes & fees
18 Sep - 19 Sep
Rodeway Inn & Suites Winter Haven Chain Of Lakes
2 outdoor pools, open 11:00 AM to 9:00 PM, pool umbrellas, sun loungers
Pirate Island Theme | In-room safe, desk, laptop workspace, soundproofing
Kingdom Theme | In-room safe, desk, laptop workspace, soundproofing
Exterior

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
SAR 747
SAR 984 total
includes taxes & fees
22 Sep - 23 Sep
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

Quality Inn & Suites By the Parks

Quality Inn & Suites By the Parks

10/10 Excellent
"Rooms were clean, beds super comfortable, nice cold air conditioner, breakfast good, and staff absolutely wonderful."
Jacqueline 2-night trip
Posted 1 hour ago
Quality Inn & Suites By the Parks
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"we had a good stay , everything was good"
Maylin 3-night trip
Posted 9 hours ago
Hilton Vacation Club Mystic Dunes Orlando
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"It was great and being able to text the front desk was awesome"
Megan 3-night trip
Posted 1 day ago
Vacation Village Orlando, Celebration
Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"Hidden resort Gem on a budget"
Don 1-night trip
Posted 1 day ago
Delta Hotels by Marriott Orlando Celebration

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 20 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's 20 hotels in Winter Haven give you a great choice for your poolside getaway.
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.