Hotels with Swimming Pools in Winter Park

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Check availability on Winter Park Hotels with Swimming Pools

Our top choices for Winter Park hotels with a pool

Outdoor pool, open 10:00 AM to 5:00 PM, pool umbrellas, pool 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
Outdoor pool, open 8:00 AM to 9:00 PM, pool 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, (670)
"Hospitable staff and nice rooms."
United States
Iryna
The price is S$110
includes taxes & fees
5 Jan - 6 Jan, 2026
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, pool umbrellas, pool loungers
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1346)
"Room, Breakfast, location AAAA+ "
United States
Ahmed Gabriel
The price is S$130
includes taxes & fees
14 Dec - 15 Dec
Hyatt House Orlando International Drive
Outdoor pool, pool umbrellas, pool 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 S$108
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, (1242)
"Nice place very good"
United States
Hugo
The price is S$134
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 S$130
includes taxes & fees
22 Dec - 23 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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"The rooms were clean and recently renovated Staff was extremely helpful "
Kathleen 5-night trip
Posted 20 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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Frequently asked questions

What are some accommodation options 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 swimming pools and 2 restaurants. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Offers 2 coffee shops/cafes, 3 outdoor swimming 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 swimming 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 such as 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. Travellers 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 the local weather in Winter Park into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 28°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Park are August, September, July and June, with each month seeing an average of 185 mm 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. If you want to venture outside the area, take a train from Winter Park Station. Winter Park might not have many public transport options, so consider renting a car to explore more.