The Best Hotels with a Pool in Winter Park, FL from AED 306 in 2026

Q: 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. 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. DoubleTree by Hilton at the Entrance to Universal Orlando : Hotel, 3-minute walk from Universal Orlando Resort. Features a children's pool, an outdoor pool, and 2 restaurants. Waldorf Astoria Orlando - An Official Walt Disney World® Hotel : Resort located near Walt Disney World® Resort. Offers a lazy river, 2 outdoor pools, and 6 restaurants.

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Our top choices for Winter Park hotels with a pool

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

Orlando

Relax poolside at a cozy retreat with both private and outdoor pools, just 12 minutes from University of Central Florida.

AED 677 total

includes taxes & fees

29 Jul - 30 Jul

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

Orlando

AED 1,077 total

includes taxes & fees

29 Jun - 30 Jun

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

The Alfond Inn

Winter Park

Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.

AED 1,122 total

includes taxes & fees

5 Jul - 6 Jul

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

Dive into a cool-down oasis with a spacious outdoor pool, hot tub, and poolside bar service.

AED 579 total

includes taxes & fees

17 Jul - 18 Jul

Wyndham Garden Lake Buena Vista – Disney Springs® Area

Lake Buena Vista

Splash into family-friendly fun with 2 outdoor pools and a poolside bar at this Disney Springs resort.

AED 476 total

includes taxes & fees

29 Jun - 30 Jun

Outdoor pool, pool umbrellas, sun loungers

La Quinta Inn & Suites by Wyndham Orlando Airport

Airport North

Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.

AED 305 total

includes taxes & fees

13 Jul - 14 Jul

Hampton Inn & Suites Orlando Airport @ Gateway Village

Airport North

Vibrant pool oasis near Orlando Airport beckons travelers to dive in after a day exploring nearby attractions.

AED 403 total

includes taxes & fees

30 Jun - 1 Jul

Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

International Drive District

Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.

AED 313 total

includes taxes & fees

19 Jul - 20 Jul

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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

Universal's Cabana Bay Beach Resort

10/10 Excellent

"I’ve been coming to this hotel for 10 years. I still love it especially if you’re going to volcano bay because of its accessibility but they need to give their older rooms some love. We had a blinking light bulb in the closet, the head boards were peeling and it was very obvious due to its orange color."

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8/10 Good

"Rooms were clean, staff was friendly! Serves breakfast if you care about that. Nice pools. Only complaint is a surprise $30 a day to park your rental car there. And they could really use golf carts to get ppl around since the property is massive. Otherwise great stay close to the parks without spending the exorbitant amount Disney wants you to in order to stay on their property hotels."

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"Outstanding customer service, from the receptionists, bar tenders, and housekeeping staff. We typically stay on property for a Disney trip, but this was a quick two night/one day of Disney stay before a cruise. From the included breakfast, dinner/bar drinks, popcorn/soda, coffee bar, and resort shuttle, it may be difficult to not stay here in the future for Disney trips! I will check for a Drury anytime I need to travel from now on!"

Coco Key Hotel & Water Park Resort

8/10 Good

"Nice place to get away and enjoy with the family. The water park was great and everything is at a walking distance. Although there is the availibility to travel to near Entertainment Parks if the finances are not sufficient, only the stay at the resort will suffice your vacation plans. Be sure to check into the resort fees before you book your stay so that it would be within your budget. We did not take notice of the fees and parking cost, which I think should be included with your stay and found them to be excesive. However, as far as the facilities and resort, there are no complaints."

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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. 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. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 3-minute walk from Universal Orlando Resort. Features a children's pool, an outdoor pool, and 2 restaurants. Waldorf Astoria Orlando - An Official Walt Disney World® Hotel: Resort located near Walt Disney World® Resort. Offers a lazy river, 2 outdoor pools, and 6 restaurants.

What is there to see and do in Winter Park?

Explore places like Kia Center, Universal Studios Florida, and Universal Orlando 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.

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Our top choices for Winter Park hotels with a pool

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