Search Hotels with Pool in Winter Park

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Check availability on Winter Park Hotels with Pool

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winter Park hotels with a pool

2 outdoor pools, open 10:00 AM to 5:00 PM, pool cabanas (surcharge)
The Alfond Inn

The Alfond Inn

The Alfond Inn
4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1003)
"Great very clean staff wonderful "
United States
Lisa
The Alfond Inn
Property amenity
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

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, (741)
"What a wonderful stay! "
United States
Lucia
The price is ฿2,615
฿2,942 total
includes taxes & fees
26 Jan - 27 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

Hyatt House Orlando International Drive
4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1395)
"Good location, good breakfast "
United States
Andrea
The price is ฿3,667
฿4,125 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hyatt House Orlando International Drive
Outdoor pool, pool umbrellas, pool loungers
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
Orlando
8.8 out of 10, Excellent, (1917)
"Good place to stay "
United States
victor
The price is ฿2,424
฿2,727 total
includes taxes & fees
4 Jan - 5 Jan 2026
Aloft Orlando Lake Buena Vista
Outdoor pool
Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
2.5 star property
Florida Center
9.0 out of 10, Wonderful, (479)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is ฿2,680
฿3,015 total
includes taxes & fees
26 Jan - 27 Jan 2026
Spark by Hilton Orlando near Universal
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4376)
"Great place to stay. Definitely will stay here again.."
United States
Donnell
The price is ฿3,704
฿4,167 total
includes taxes & fees
23 Jan - 24 Jan 2026
Rosen Shingle Creek
Outdoor pool, pool umbrellas, pool loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
International Drive District
7.4 out of 10, Good, (3929)
"Excellent room and the beds were very comfortable, also very clean "
United States
Daisy
The price is ฿1,936
฿2,807 total
includes taxes & fees
4 Jan - 5 Jan 2026
Wyndham I-Drive Avanti Resort & Conference Center
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

CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

10/10 Excellent
"Swimming pool was cleaned and enjoyable. Staff were very friendly and warming. I really loved this place. My kids enjoyed every single thing. "
Marianna 1-night trip
Posted 2 days ago
CoCo Key Hotel and Water Resort 

Frequently asked questions

What are some accommodation options with pools in Winter Park?
DoubleTree by Hilton Hotel Orlando at SeaWorld: Resort, 8-minute walk from Aquatica. Features 2 outdoor swimming pools, a children's pool and 2 restaurants. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor swimming pools and 2 restaurants. Wyndham I-Drive Avanti Resort & Conference Center: Hotel, 7-minute walk from CoCo Key Water Resort. Provides a children's pool, an outdoor pool and 2 bars. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Features 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. Offers a children's pool, an outdoor pool and 2 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.