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Search Hotels with Pool in Winter Haven

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Check availability on Winter Haven Hotels with Pool

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for Winter Haven hotels with a pool

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.
฿3,726
฿4,173 total
includes taxes & fees
3 Sept - 4 Sept
Best Western Plus Winter Haven Inn & Suites 

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.
฿2,920
฿3,270 total
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Winter Haven by IHG

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.
฿3,729
฿4,176 total
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn Winter Haven

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.
฿4,560
฿5,108 total
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Winter Haven

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.
฿2,778
฿3,112 total
includes taxes & fees
28 Aug - 29 Aug
Howard Johnson by Wyndham Winter Haven FL

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.
฿3,762
฿4,214 total
includes taxes & fees
31 Aug - 1 Sept
Staybridge Suites Winter Haven Auburndale by IHG

7. LEGOLAND Beach Retreat

LEGOLAND Beach Retreat
Winter Haven
฿5,807
฿7,785 total
includes taxes & fees
28 Aug - 29 Aug
LEGOLAND Beach Retreat

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.
฿4,530
฿5,073 total
includes taxes & fees
13 Sept - 14 Sept
Home2 Suites By Hilton Winter Haven

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.
฿2,781
฿3,114 total
includes taxes & fees
27 Aug - 28 Aug
Lake Roy Beach Inn

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.
฿2,324
฿2,603 total
includes taxes & fees
29 Aug - 30 Aug
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

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 
Winter Haven
฿3,726
฿4,173 total
includes taxes & fees
3 Sept - 4 Sept
Best Western Plus Winter Haven Inn & Suites 

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG
Winter Haven
฿2,920
฿3,270 total
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Winter Haven by IHG

Hampton Inn Winter Haven

Hampton Inn Winter Haven
Winter Haven
฿3,729
฿4,176 total
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn Winter Haven

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG
Winter Haven
฿3,762
฿4,214 total
includes taxes & fees
31 Aug - 1 Sept
Staybridge Suites Winter Haven Auburndale by IHG

Courtyard by Marriott Winter Haven

Courtyard by Marriott Winter Haven
Winter Haven
฿4,560
฿5,108 total
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Winter Haven

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL
Winter Haven
฿2,778
฿3,112 total
includes taxes & fees
28 Aug - 29 Aug
Howard Johnson by Wyndham Winter Haven FL

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven
Winter Haven
฿4,530
฿5,073 total
includes taxes & fees
13 Sept - 14 Sept
Home2 Suites By Hilton Winter Haven

Legoland Florida Hotel

Legoland Florida Hotel
Winter Haven
฿7,057
฿9,186 total
includes taxes & fees
16 Sept - 17 Sept
Legoland Florida Hotel

Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Winter Haven
฿2,642
฿2,959 total
includes taxes & fees
28 Aug - 29 Aug
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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"being staying in this property since 2017 no complains favorite so far very family friendly"
Ailyn 1-night trip
Posted 1 hour ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"1"
grisel 3-night trip
Posted 2 hours ago
Hilton Vacation Club Mystic Dunes Orlando
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

8/10 Good
"This was fine for a 1 night stay when taking my kid to college, nothing special but it gets the job done."
Joshua 1-night trip
Posted 5 hours ago
Howard Johnson by Wyndham Winter Haven FL
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Room was clean second time staying here no issues. Children loved the pool and water park awesome after a long day of exploring"
Mohinie 5-night trip
Posted 8 hours ago
Hilton Vacation Club Aqua Sol Orlando West
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent
"Everything was wonderful"
Mary 1-night trip
Posted 1 day ago
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

10/10 Excellent
"Clean room and excellent customer service."
Johnathan 1-night trip
Posted 2 days ago
Holiday Inn Winter Haven by IHG

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 20 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'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 such as LEGOLAND® Florida while you're in Winter Haven. Make a point to visit attractions such as 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 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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