Find Hotels with a Pool in Winter Park, FL

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Check availability on Winter Park Hotels with a Pool

Our top choices for Winter Park hotels with a pool

Outdoor pool

1-bedroom vacation room just 12 minutes from University of Central Florida

1-bedroom vacation room just 12 minutes from University of Central Florida
Orlando
9.4 out of 10, Exceptional, (3 reviews)
  • cleanliness
    Relax poolside at a cozy retreat with both private and outdoor pools, just 12 minutes from University of Central Florida.
"Fantastic Host"
United States
Marek K.
The price is SAR 220
SAR 639 total
includes taxes & fees
18 May - 19 May
1-bedroom vacation room just 12 minutes from University of Central Florida
Outdoor pool

Quiet and safe neighborhood come to this great place with lots of room for relax

Quiet and safe neighborhood come to this great place with lots of room for relax
Orlando
10.0 out of 10, Exceptional, (2 reviews)
"Pool is very inviting"
United States
Geri Lamborn M.
The price is SAR 500
SAR 1,097 total
includes taxes & fees
17 May - 18 May
Quiet and safe neighborhood come to this great place with lots of room for relax
2 outdoor pools, open 10:00 AM to 5:00 PM, cabanas (surcharge)

The Alfond Inn

The Alfond Inn
4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
"A beautiful hotel in a historic Florida town that is an easy walk to a shopping and dining thoroughfare, with fine dining, pool, gym, spa…."
United States
Denise
The price is SAR 959
SAR 1,184 total
includes taxes & fees
24 May - 25 May
The Alfond Inn
Exterior

Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
4.0 star property
Orlando
9.0 out of 10, Wonderful, (2,926 reviews)
  • cleanliness
    Splash into aquatic bliss at this resort with 5 outdoor pools, a lazy river, and poolside cabanas.
"Amazing location, pools were perfect, just need more food options"
United States
Brian
The price is SAR 570
SAR 819 total
includes taxes & fees
14 Jun - 15 Jun
Wyndham Grand Orlando Resort Bonnet Creek
Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
International Drive District
8.6 out of 10, Excellent, (1,369 reviews)
  • cleanliness
    Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.
"Food was good for breakfast pool was awesome"
Canada
Donald
The price is SAR 340
SAR 383 total
includes taxes & fees
21 May - 22 May
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, pool umbrellas, sun loungers

La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport
3.0 star property
Airport North
7.4 out of 10, Good, (1,944 reviews)
  • cleanliness
    Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.
"The pool was nice."
United States
Jason
The price is SAR 265
SAR 298 total
includes taxes & fees
11 Jun - 12 Jun
La Quinta Inn & Suites by Wyndham Orlando Airport
Outdoor pool, sun loungers

TRYP by Wyndham Orlando

TRYP by Wyndham Orlando
3.0 star property
International Drive District
9.0 out of 10, Wonderful, (1,221 reviews)
  • cleanliness
    Take a splash in the sun-kissed outdoor pool with comfortable loungers at this art deco retreat.
"the pool was great"
United States
Melody
The price is SAR 385
SAR 433 total
includes taxes & fees
31 May - 1 Jun
TRYP by Wyndham Orlando
Water park

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area
4.0 star property
Orlando
8.4 out of 10, Very Good, (6,435 reviews)
  • cleanliness
    Splash into aquatic paradise with 7 pools, a lazy river, and waterslides at this family resort.
"I loved the pool and bar area , will revisit soon !"
United States
Monique
The price is SAR 366
SAR 538 total
includes taxes & fees
18 May - 19 May
Westgate Lakes Resort & Spa Universal Studios Area
Outdoor pool, sun loungers

Hilton Vacation Club Polynesian Isles Kissimmee

Hilton Vacation Club Polynesian Isles Kissimmee
3.0 star property
Kissimmee
9.6 out of 10, Exceptional, (1,941 reviews)
  • cleanliness
    Take a plunge in the pool paradise with sun loungers at this family-friendly Kissimmee retreat.
"Yes great staff very friendly and they have hot tubs and 4 pools that stay open till 11pm super relaxing"
United States
Emily
The price is SAR 339
SAR 470 total
includes taxes & fees
1 Jun - 2 Jun
Hilton Vacation Club Polynesian Isles Kissimmee
Outdoor pool

Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
Airport North
9.6 out of 10, Exceptional, (3,000 reviews)
  • cleanliness
    Refreshing outdoor pool sanctuary awaits near Florida Mall, with a firepit and poolside lounging for a sunny getaway experience.
"Clean room, early check in, helpful/friendly staff, awesome pool & great breakfast!"
Canada
Jillian
The price is SAR 413
SAR 464 total
includes taxes & fees
27 May - 28 May
Hyatt House Orlando Airport
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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Choose what matters most at hotels with a pool in Winter Park

Breakfast included
4 stars

Top Winter Park Hotel Reviews

B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

10/10 Excellent
"The room was very spacious and clean, with no bad smells. The two beds were also very large. The only downside was that even with all the lights turned on, the room still felt a little dark"
Xiaoxuan 1-night trip
Posted 1 hour ago
B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

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Frequently asked questions

What are some accommodations with pools in Winter Park?
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Aparthotel located near Disney Springs™. Features 6 outdoor pools, a children's pool, and 3 restaurants. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, and 2 restaurants. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 3-minute walk from Universal Orlando Resort. Provides a children's pool, an outdoor pool, and 2 restaurants. Westgate Lakes Resort & Spa Universal Studios Area: Hotel located near The Orlando Eye. Features 7 outdoor pools, a children's pool, and a water park. Rosen Inn at Pointe Orlando: Hotel, 14-minute walk from Orange County Convention Center. Offers 2 coffee shops/cafes, 3 outdoor pools, and complimentary wireless internet access.
What is there to see and do in Winter Park?
Explore places like Universal Studios Florida, Universal Orlando Resort, and Universal's Volcano Bay while you're in the area. Spend some time experiencing the great outdoors at Lake Virginia and Mead Garden. Travelers love Winter Park for its array of dining options.
When is the best time to book a hotel with a pool in Winter Park?
Taking into account the local weather in Winter Park can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Park are August, September, July, and June, with each month seeing an average of 7 inches of rainfall.
What's the best way to travel around Winter Park?
Knowing the transportation options in Winter Park can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Winter Park Station. Winter Park might not have very many public transit choices so consider renting a car to explore more.