Find Hotels with a Pool in Winter Park, FL

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Check availability on Winter Park Hotels with a Pool

Top Winter Park Hotels with a Pool

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, (1001)
"Beautiful hotel"
United States
Paige
The Alfond Inn
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, (605)
"Awesome hotel. And the great price is an added bonus!"
United States
Khristo
The price is NT$2,362
NT$2,658 total
includes taxes & fees
Dec 11 - Dec 12
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
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, (1870)
"Great stay"
United States
Ramprasad
The price is NT$2,186
NT$2,459 total
includes taxes & fees
Nov 24 - Nov 25
Aloft Orlando Lake Buena Vista
View from property
AC Hotel by Marriott Orlando Lake Buena Vista

AC Hotel by Marriott Orlando Lake Buena Vista

3.5 star property
Orlando
9.2 out of 10, Wonderful, (1619)
"This property was the best location for my trip close to every thing and everywhere"
United States
abayomi
The price is NT$2,470
NT$2,779 total
includes taxes & fees
Nov 30 - Dec 1
AC Hotel by Marriott Orlando Lake Buena Vista
Outdoor pool, open 9:00 AM to 9:00 PM, sun loungers
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3.0 star property
Kissimmee
8.2 out of 10, Very Good, (5147)
"Clean room, nice staff, good breakfast, and kid friendly amenities. "
United States
Marcos
Palazzo Lakeside Hotel
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, (1016)
"The property is amazing! "
United States
Lissette
The price is NT$2,142
NT$2,410 total
includes taxes & fees
Dec 17 - Dec 18
TRYP by Wyndham Orlando
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

4.5 star property
Orlando
9.4 out of 10, Exceptional, (4244)
"Great resort "
United States
Camille
The price is NT$3,470
NT$3,904 total
includes taxes & fees
Dec 18 - Dec 19
Rosen Shingle Creek
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

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Better than expected "
Dinesha 3-night trip
Posted 2 days ago
Rosen Inn at Pointe 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. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Offers 6 outdoor pools, a children's pool, and 3 restaurants. Ramada by Wyndham Suites Orlando Airport: Provides a snack bar/deli, an outdoor pool, and daily. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Features 2 coffee shops/cafes, 3 outdoor pools, and complimentary wireless internet access. Rosen Inn Lake Buena Vista: Hotel located near Disney Springs™. Offers 2 outdoor pools, a children's pool, and a snack bar/deli.
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 Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens. 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.