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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
20 Aug - 21 Aug
Tomorrow
21 Aug - 22 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Winter Haven hotels with a pool

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

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.
AED 419
AED 469 total
includes taxes & fees
23 Aug - 24 Aug
Best Western Plus Winter Haven Inn & Suites 
Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers
Reception
Reception
Exterior

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.
AED 309
AED 346 total
includes taxes & fees
20 Sep - 21 Sep
Holiday Inn Winter Haven by IHG
Outdoor pool, pool umbrellas, sun loungers
Combined shower/tub, free toiletries, hair dryer, towels
Lobby
Reception

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.
AED 402
AED 450 total
includes taxes & fees
23 Aug - 24 Aug
Hampton Inn Winter Haven
Outdoor pool, pool umbrellas, sun loungers
Premium bedding, down comforters, pillowtop beds, blackout drapes
Studio Suite, 2 Queen Beds, Kitchen, Lake View | Premium bedding, down comforters, pillowtop beds, blackout drapes
Exterior

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.
AED 378
AED 424 total
includes taxes & fees
30 Aug - 31 Aug
Staybridge Suites Winter Haven Auburndale by IHG
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
Property amenity
Lobby
Exterior

5. 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.
AED 496
AED 556 total
includes taxes & fees
30 Aug - 31 Aug
Courtyard by Marriott Winter Haven
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Children's play area - outdoor
Children's area
Property entrance

6. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
AED 621
AED 840 total
includes taxes & fees
11 Sep - 12 Sep
LEGOLAND Beach Retreat
Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers
Combined shower/tub, eco-friendly toiletries, hair dryer, towels
Free daily continental breakfast
Interior entrance

7. 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.
AED 312
AED 350 total
includes taxes & fees
22 Aug - 23 Aug
Howard Johnson by Wyndham Winter Haven FL
Seasonal outdoor pool
Terrace/patio
LED TV, Netflix, streaming services
Free daily buffet breakfast

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.
AED 479
AED 536 total
includes taxes & fees
30 Aug - 31 Aug
Home2 Suites By Hilton Winter Haven
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.
AED 298
AED 334 total
includes taxes & fees
28 Aug - 29 Aug
Lake Roy Beach Inn
Outdoor pool, pool umbrellas, sun loungers
Quadruple Room, Non Smoking, Lake View | Living area | TV
Lake
Standard Room, 1 Queen Bed, Non Smoking | Private kitchenette | Coffee/tea maker, fridge, microwave, oven

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.
AED 251
AED 281 total
includes taxes & fees
20 Sep - 21 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

Reception
Restaurant
Exterior
Reception

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
AED 309
AED 346 total
includes taxes & fees
20 Sep - 21 Sep
Holiday Inn Winter Haven by IHG
Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room) | Desk, laptop workspace, blackout drapes, iron/ironing board
Reception
Free daily full breakfast
Exterior

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
AED 419
AED 469 total
includes taxes & fees
23 Aug - 24 Aug
Best Western Plus Winter Haven Inn & Suites 
Exterior
Outdoor pool, pool umbrellas, sun loungers
Desk, iron/ironing board, cribs (free), WiFi (free)
Lobby

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
AED 402
AED 450 total
includes taxes & fees
23 Aug - 24 Aug
Hampton Inn Winter Haven
Exterior
Exterior
Free daily continental breakfast
Studio Suite, 2 Queen Beds, Kitchen, Lake View | Premium bedding, down comforters, pillowtop beds, blackout drapes

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
AED 378
AED 424 total
includes taxes & fees
30 Aug - 31 Aug
Staybridge Suites Winter Haven Auburndale by IHG
Blackout drapes, iron/ironing board, cribs (free)
Reception
Reception
Free daily continental breakfast

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
AED 312
AED 350 total
includes taxes & fees
22 Aug - 23 Aug
Howard Johnson by Wyndham Winter Haven FL
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Children's play area - outdoor
Exterior
Children's area

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
AED 621
AED 840 total
includes taxes & fees
11 Sep - 12 Sep
LEGOLAND Beach Retreat
Property amenity
Lobby
Breakfast and dinner served
Exterior

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
AED 496
AED 556 total
includes taxes & fees
30 Aug - 31 Aug
Courtyard by Marriott Winter Haven
Terrace/patio
Free daily buffet breakfast
Lobby
LED TV, Netflix, streaming services

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
AED 479
AED 536 total
includes taxes & fees
30 Aug - 31 Aug
Home2 Suites By Hilton Winter Haven
Free daily continental breakfast
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)
Lobby
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
AED 297
AED 332 total
includes taxes & fees
23 Aug - 24 Aug
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
AED 902
AED 1,154 total
includes taxes & fees
2 Sep - 3 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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

8/10 Good
"We loved our stay as always."
Miranda 14-night trip
Posted less than an hour ago
Hilton Vacation Club Mystic Dunes Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

8/10 Good
"The food wasn't very good. We need to know we're a good restaurant is in on the property but that was the only complaint The parking was excellent for me. I'm handicap and I liked I was in the garage"
Gary 1-night trip
Posted 1 hour ago
The Grove Resort & Water Park Orlando
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"Very clean place, close to everything, we will love to go back definitely in the future ❤️"
Aurelis 2-night trip
Posted 2 hours ago
Vacation Village Orlando, Celebration
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent
"Nice lobby area. Breakfast was great. Kids enjoyed the pool."
Julia 2-night trip
Posted 2 hours ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

10/10 Excellent
"I was pleasantly surprised with this hotel. The room was spacious, very clean, and the beds were comfortable. The exterior of this property looks kind of rundown. It is a very old hotel with that being said the room was very clean and very comfortable. The lobby was also clean. The staff was very helpful."
Dustin 1-night trip
Posted 2 hours ago
Howard Johnson by Wyndham Winter Haven FL
Galleria Palms Hotel

Galleria Palms Hotel

10/10 Excellent
"Clean room, kind personnel"
Sabrina 2-night trip
Posted 18 hours ago
Galleria Palms Hotel
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"The rooms were all spotless. The staff was very friendly."
Jill 4-night trip
Posted 1 day 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 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?
Economy Suites: Features free self parking, an outdoor pool, and complimentary wireless internet access. Courtyard by Marriott Winter Haven: Hotel located near LEGOLAND® Florida. Offers free self parking, a 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 The Circle B Bar Reserve 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.