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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
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sep
Next weekend
4 Sep - 6 Sep
In two weeks
11 Sep - 13 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
Free daily full breakfast

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 428
SAR 479 total
includes taxes & fees
1 Sep - 2 Sep
Best Western Plus Winter Haven Inn & Suites 
Outdoor pool, open 8:00 AM to 9:00 PM, sun loungers
Outdoor pool, open 8:00 AM to 9:00 PM, sun loungers
Desk, blackout drapes, iron/ironing board, cribs (free)
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.
SAR 329
SAR 368 total
includes taxes & fees
27 Sep - 28 Sep
Holiday Inn Winter Haven by IHG
Outdoor pool, pool umbrellas, sun loungers
Combined shower/tub, free toiletries, hair dryer, towels
Lobby
Exterior

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.
SAR 428
SAR 479 total
includes taxes & fees
6 Sep - 7 Sep
Hampton Inn Winter Haven
Outdoor pool, pool umbrellas, sun loungers
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

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.
SAR 454
SAR 509 total
includes taxes & fees
6 Sep - 7 Sep
Staybridge Suites Winter Haven Auburndale by IHG
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
Property amenity
Exterior
Reception

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.
SAR 539
SAR 604 total
includes taxes & fees
6 Sep - 7 Sep
Courtyard by Marriott Winter Haven
Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers
Blackout drapes, iron/ironing board, cribs (free)
Combined shower/tub, eco-friendly toiletries, hair dryer, towels
Interior entrance

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 319
SAR 357 total
includes taxes & fees
1 Sep - 2 Sep
Howard Johnson by Wyndham Winter Haven FL
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Children's area
Exterior
Children's play area - outdoor

7. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
SAR 747
SAR 984 total
includes taxes & fees
11 Sep - 12 Sep
LEGOLAND Beach Retreat
Seasonal outdoor pool
LED TV, Netflix, streaming services
Free daily buffet breakfast
Terrace/patio

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.
SAR 520
SAR 583 total
includes taxes & fees
6 Sep - 7 Sep
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.
SAR 315
SAR 352 total
includes taxes & fees
10 Sep - 11 Sep
Lake Roy Beach Inn
Outdoor pool, pool umbrellas, sun loungers
Quadruple Room, Non Smoking, Lake View | Living area | TV
Standard Room, 1 Queen Bed, Non Smoking | Private kitchenette | Coffee/tea maker, fridge, microwave, oven
Standard Room, 1 Queen Bed, Non Smoking | Living area | TV

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 260
SAR 292 total
includes taxes & fees
7 Sep - 8 Sep
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

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

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
SAR 428
SAR 479 total
includes taxes & fees
1 Sep - 2 Sep
Best Western Plus Winter Haven Inn & Suites 
Desk, blackout drapes, iron/ironing board, cribs (free)
Outdoor pool, open 8:00 AM to 9:00 PM, sun loungers
Exterior
Fitness facility

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
SAR 329
SAR 368 total
includes taxes & fees
27 Sep - 28 Sep
Holiday Inn Winter Haven by IHG
Exterior
Outdoor pool, pool umbrellas, sun loungers
Desk, iron/ironing board, cribs (free), WiFi (free)
Reception

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
SAR 428
SAR 479 total
includes taxes & fees
6 Sep - 7 Sep
Hampton Inn Winter Haven
Exterior
Studio Suite, 2 Queen Beds, Kitchen, Lake View | Premium bedding, down comforters, pillowtop beds, blackout drapes
Free daily continental breakfast
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
6 Sep - 7 Sep
Staybridge Suites Winter Haven Auburndale by IHG
Blackout drapes, iron/ironing board, cribs (free)
Interior entrance
Reception
Free daily continental breakfast

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
SAR 319
SAR 357 total
includes taxes & fees
1 Sep - 2 Sep
Howard Johnson by Wyndham Winter Haven FL
Property amenity
Lobby
Exterior
Reception

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
SAR 539
SAR 604 total
includes taxes & fees
6 Sep - 7 Sep
Courtyard by Marriott Winter Haven
Terrace/patio
Lobby
LED TV, Netflix, streaming services
Free daily buffet breakfast

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
SAR 520
SAR 583 total
includes taxes & fees
6 Sep - 7 Sep
Home2 Suites By Hilton Winter Haven
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
Breakfast and dinner served

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
SAR 811
SAR 1,055 total
includes taxes & fees
31 Aug - 1 Sep
Legoland Florida Hotel
Free daily continental breakfast
Outdoor pool
Suite, 1 King Bed, Non Smoking | Desk, laptop workspace, iron/ironing board (on request), WiFi (free)
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 319
SAR 357 total
includes taxes & fees
31 Aug - 1 Sep
Rodeway Inn & Suites Winter Haven Chain Of Lakes
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.
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Top Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

8/10 Good
"Our room we’re missing the pot and pan that seems to been pictured so we had to buy our own, and if anything the rooms could use more trash cans especially in the bathrooms"
Mariella 3-night trip
Posted 8 hours ago
The Grove Resort & Water Park Orlando
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Staff is friendly, close to many things"
Chris 1-night trip
Posted 11 hours ago
Holiday Inn Winter Haven by IHG

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 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 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.