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
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

3.0 star property
Orlando
10.0 out of 10, Exceptional, (1)
"Pool is very inviting"
United States
Geri Lamborn M.
The price is AED 426
AED 996 total
includes taxes & fees
21 Dec - 22 Dec
Quiet and safe neighborhood come to this great place with lots of room for relax
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)
"Fantastic Host"
United States
Marek K.
The price is AED 195
AED 603 total
includes taxes & fees
21 Dec - 22 Dec
1-bedroom vacation room just 12 minutes from University of Central Florida
Pool
Magic Studio

Magic Studio

Orlando
9.6 out of 10, Exceptional, (4)
"Clean, roomy for two, comfortable bed, Met all our needs. Plan to stay there again."
United States
Nan D.
The price is AED 400
AED 834 total
includes taxes & fees
31 Dec - 1 January 2026
Magic Studio
Outdoor pool, open 10:00 AM to 5:00 PM, pool umbrellas, sun loungers
The Alfond Inn

The Alfond Inn

4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1000)
"Amazing location, warm and friendly staff, beautiful property!"
Canada
Diandra
The Alfond Inn
Pool
Cozy RV with AC and fitness room in brilliant Winter Park

Cozy RV with AC and fitness room in brilliant Winter Park

Goldenrod
The price is AED 367
AED 485 total
includes taxes & fees
14 Dec - 15 Dec
Cozy RV with AC and fitness room in brilliant Winter Park
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
8.8 out of 10, Excellent, (669)
"Hospitable staff and nice rooms."
United States
Iryna
The price is AED 278
AED 313 total
includes taxes & fees
4 Jan - 5 January 2026
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, pool umbrellas, sun loungers
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1345)
"Room, Breakfast, location AAAA+ "
United States
Ahmed Gabriel
The price is AED 327
AED 368 total
includes taxes & fees
14 Dec - 15 Dec
Hyatt House Orlando International Drive
Outdoor pool, pool umbrellas, sun loungers
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

3.0 star property
Orlando
8.8 out of 10, Excellent, (1905)
"Great rooms, staff, and property!"
United States
Cindy
The price is AED 272
AED 306 total
includes taxes & fees
14 Dec - 15 Dec
Aloft Orlando Lake Buena Vista
Terrace/patio
Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1241)
"Nice place very good"
United States
Hugo
The price is AED 334
AED 379 total
includes taxes & fees
18 Dec - 19 Dec
Embassy Suites by Hilton Orlando Lake Buena Vista South
Water park
Red Lion Hotel Orlando Lake Buena Vista South

Red Lion Hotel Orlando Lake Buena Vista South

3.5 star property
Kissimmee
8.8 out of 10, Excellent, (4252)
"Beautiful place to stay, reliable price, the location was perfect, super clean, definitely I will return back in a future to this hotel."
United States
Aurelis
The price is AED 250
AED 367 total
includes taxes & fees
14 Dec - 15 Dec
Red Lion Hotel Orlando Lake Buena Vista South
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 Park Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Very nice hotel. Beautiful and convenient."
Pamella 1-night trip
Posted 1 day ago
DoubleTree by Hilton at the Entrance to Universal Orlando

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Frequently asked questions

What are some accommodations with pools in Winter Park?
Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Features a lazy river, 2 outdoor pools, and 2 restaurants. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Offers 2 coffee shops/cafes, 3 outdoor pools, and complimentary wireless internet access. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 2-minute walk from Universal Orlando Resort. Provides a children's pool, an outdoor pool, and 2 restaurants. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Features 6 outdoor pools, a children's pool, and 3 restaurants. Hyatt Regency Orlando: Hotel, 2-minute walk from Orange County Convention Center. Offers a children's pool, an outdoor pool, and 3 restaurants.
What is there to see and do in Winter Park?
Explore places like Universal Studios Florida, Universal Orlando Resort, and Walt Disney World® Resort while you're in the area. Spend some time experiencing the great outdoors at Kraft Azalea Gardens and Lake Virginia. 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.