Find Hotels with an Outdoor Pool in Winter Haven, FL

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Top Winter Haven Hotels with an Outdoor Pool

Legoland Florida Hotel

3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (49)
"Really enjoyable stay. "
United Kingdom
John
$338 nightly
The price is $379
Dec 8 - Dec 9
Total with taxes and fees
Legoland Florida Hotel

Holiday Inn Winter Haven by IHG

3.0 star property
Winter Haven
9.0 out of 10, Wonderful, (1001)
"Clean room, great staff, easy check-in."
United States
Vanessa
$125 nightly
The price is $140
Dec 22 - Dec 23
Total with taxes and fees
Holiday Inn Winter Haven by IHG

Home2 Suites By Hilton Winter Haven

3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (249)
"Everything feom the staff to the room was great!"
United States
Eduardo
$143 nightly
The price is $160
Dec 14 - Dec 15
Total with taxes and fees
Home2 Suites By Hilton Winter Haven

Hampton Inn Winter Haven

2.5 star property
Winter Haven
9.0 out of 10, Wonderful, (1001)
"Clean room, staff was nice, breakfast was good, easy parking."
United States
Jessica
$111 nightly
The price is $125
Dec 14 - Dec 15
Total with taxes and fees
Hampton Inn Winter Haven

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
Winter Haven
9.6 out of 10, Exceptional, (1071)
"Excellent place to stay"
United States
Anita
$134 nightly
The price is $151
Dec 21 - Dec 22
Total with taxes and fees
Best Western Plus Winter Haven Inn & Suites 

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
Winter Haven
7.0 out of 10, Good, (1000)
"Nice hotel. Clean and great location. "
United States
Raylene
$85 nightly
The price is $95
Dec 8 - Dec 9
Total with taxes and fees
Howard Johnson by Wyndham Winter Haven FL

Courtyard by Marriott Winter Haven

3.0 star property
Winter Haven
9.4 out of 10, Exceptional, (730)
"Great staff, great location "
United States
katherine
$165 nightly
The price is $185
Dec 21 - Dec 22
Total with taxes and fees
Courtyard by Marriott Winter Haven

Lake Roy Beach Inn

2.0 star property
Winter Haven
7.0 out of 10, Good, (983)
"clean room"
United States
stephen
$84 nightly
The price is $95
Dec 7 - Dec 8
Total with taxes and fees
Lake Roy Beach Inn

Staybridge Suites Winter Haven Auburndale by IHG

3.0 star property
Winter Haven
9.8 out of 10, Exceptional, (660)
"Hotel was very clean and quiet. Beds were amazing. Will stay here again"
United States
Sofia
$151 nightly
The price is $169
Jan 5 - Jan 6, 2026
Total with taxes and fees
Staybridge Suites Winter Haven Auburndale by IHG

Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Winter Haven
9.8 out of 10, Exceptional, (39)
"We had a great stay!"
United States
Harper B.
$287 nightly
The price is $317
Dec 9 - Dec 10
Total with taxes and fees
Heated Pool and Hot tub-near Legoland, Disney, Theme parks
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.

Find out more about Winter Haven

Discover top Winter Haven attractions

Winter Haven, Florida, offers a delightful blend of relaxation and adventure, making it an appealing choice for travelers seeking leisurely vacations. Begin your exploration at the stunning Cypress Gardens, where you can stroll through lush gardens filled with vibrant flowers and towering cypress trees, enjoying the serene atmosphere and picturesque views. Just a short drive away, Legoland Florida Resort provides fun for the whole family with its thrilling rides and interactive attractions, ensuring both children and adults have a fantastic time. For those who love water, the Chain of Lakes offers opportunities for boating, fishing, and picnicking along the water's edge, creating a perfect day of unwinding in nature. Don’t miss the chance to check out the Winter Haven Historical Museum to delve into the local culture and history while enjoying a peaceful afternoon. When it comes to accommodations, consider staying in hotels near Lake Eloise, where you can enjoy beautiful lake views and relax by pools designed for soothing retreats. This area is ideal for families wanting to unwind after a day of exploration, with attentive service and the convenience of nearby dining and attractions, ensuring a comfortable and enjoyable stay.

Find the best hotels with an outdoor pool in Winter Haven

For travelers seeking a refreshing retreat in Winter Haven, Florida, these hotels offer inviting outdoor pool amenities perfect for relaxation and enjoyment under the sun.

Staybridge Suites Winter Haven Auburndale by IHG

  • Why it's great for poolside lounging: With an exceptional review rating of 9.8, Staybridge Suites Winter Haven Auburndale offers an outstanding outdoor pool experience for guests. The pool area, featuring sun loungers and accessible amenities, invites travelers to relax and enjoy the Florida sunshine at their leisure.
  • Other amenities: Guests can benefit from complimentary breakfast options and a host of in-room conveniences, including kitchen facilities and premium bedding. The hotel also features fitness center access, nearby motorboating and fishing opportunities, and a concierge service to assist with local activities, ensuring a fulfilling stay for every guest.
  • Nearby attractions: Winter Haven City Tennis Center - 0.28 miles, Rotary Park - 0.92 miles

Courtyard by Marriott Winter Haven

  • Why it's great for poolside lounging: Rated 9.4 by guests, the Courtyard by Marriott Winter Haven is a superb choice for travelers who value outdoor relaxation. The outdoor pool, complemented by sun loungers and accessible features, creates an inviting atmosphere for enjoying the warm Florida climate.
  • Other amenities: Beyond the pool, guests can enjoy a 24-hour fitness center and on-site dining options. The hotel also features self-parking, housekeeping services, and scenic views of the nearby lake, providing a picturesque backdrop for a memorable stay.
  • Nearby attractions: LEGOLAND® Florida - 0.81 miles, Peppa Pig Theme Park Florida - 0.87 miles, Chain Of Wakes - 0.82 miles

Best Western Plus Winter Haven Inn & Suites

  • Why it's great for poolside lounging: The Best Western Plus Winter Haven Inn & Suites is an ideal choice for travelers looking to unwind by the pool, featuring an impressive review rating of 9.4. Guests can enjoy the outdoor pool equipped with sun loungers and accessible features, perfect for soaking up the Florida sun in comfort and style.
  • Other amenities: In addition to the fantastic outdoor pool, guests can start their day with a complimentary breakfast, including full breakfast options. The hotel also offers a fitness center, free self-parking, and convenient kitchenettes in the rooms, complete with refrigerators and microwaves, ensuring a comfortable and functional stay for all guests.
  • Nearby attractions: LEGOLAND® Florida - 0.6 miles, Peppa Pig Theme Park Florida - 0.66 miles, Chain Of Wakes - 1.08 miles

Holiday Inn Winter Haven by IHG

  • Why it's great for poolside lounging: With a stellar review rating of 9.0, the Holiday Inn Winter Haven by IHG promises a delightful experience for pool lovers. The outdoor pool, surrounded by sun loungers, invites travelers to relax and refresh, making it a perfect spot for leisure and socializing.
  • Other amenities: Guests can take advantage of 24-hour fitness facilities, ensuring a workout is always possible. The hotel also features free self-parking, a beautiful garden area, and accessible accommodations, making it accessible for all guests. Additionally, families can enjoy thoughtful amenities like free meals for children and cribs, enhancing the stay for those traveling with little ones.
  • Nearby attractions: Theatre Winter Haven - 0.32 miles, Chain of Lakes Park - 0.38 miles

Hampton Inn Winter Haven

  • Why it's great for poolside lounging: The Hampton Inn Winter Haven, with a popular review rating of 9.0, features an inviting outdoor pool that provides a refreshing escape for guests. The pool area, complete with sun loungers and gated access, ensures a safe and enjoyable environment for relaxation.
  • Other amenities: Guests will appreciate the complimentary breakfast options and daily housekeeping services. The hotel also offers accessible facilities, off-street parking, and air conditioning. Additionally, there are options for early check-in and a fitness center available for guests looking to maintain their workout routines during their stay.
  • Nearby attractions: Theatre Winter Haven - 0.7 miles, Chain of Lakes Park - 0.57 miles

Top Winter Haven Hotel Reviews

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