The Best Hotels with a Pool in Winter Park, FL from NT$1,920 in 2026

Q: What are some accommodations with pools in Winter Park?

Hyatt Regency Orlando International Airport : Features 2 restaurants, an outdoor pool, and complimentary wireless internet access. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando : Aparthotel located near Orlando Vineland Premium Outlets. Offers 6 outdoor pools, a children's pool, and 3 restaurants. Marriott's Grande Vista : Aparthotel located near Orlando Vineland Premium Outlets. Provides 4 outdoor pools, a children's pool, and 3 restaurants. Universal's Cabana Bay Beach Resort : Hotel, 5-minute walk from Universal Orlando Resort. Features a lazy river, 2 outdoor pools, and 2 restaurants. Avanti International Resort : Hotel, 9-minute walk from Pointe Orlando. Offers a children's pool, a seasonal outdoor pool, and a snack bar/deli.

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Our top choices for Winter Park hotels with a pool

A multi-story hotel with balconies, a swimming pool, and a landscaped courtyard.

1. The Alfond Inn

Winter Park

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

NT$11,845 total

includes taxes & fees

Nov 1 - Nov 2

A pool area with a hot tub, lounge chairs, and a covered seating area.

2. Comfort Suites Downtown

Ivanhoe Village

Make a splash in downtown Orlando with this hotel's seasonal outdoor pool and relaxing hot tub for post-exploration recovery.

NT$4,331 total

includes taxes & fees

Nov 27 - Nov 28

A swimming pool with wooden deck seating, palm trees, and a modern building in the background.

3. Courtyard by Marriott Orlando Downtown

Ivanhoe Village

Float in sunshine at downtown Orlando's chic hotel pool, surrounded by plush loungers and umbrellas.

NT$4,955 total

includes taxes & fees

Nov 22 - Nov 23

A swimming pool with lounge chairs and umbrellas, surrounded by a multi-story building with balconies.

4. Hyatt House Orlando Airport

Airport North

Refreshing outdoor pool sanctuary awaits near Florida Mall, with a firepit and poolside lounging for a sunny getaway experience.

NT$4,326 total

includes taxes & fees

Nov 22 - Nov 23

A hot tub with a waterfall mural, a metal ladder, and a tiled floor.

5. Wingate by Wyndham - Orlando International Airport

Airport North

Refreshing outdoor pool oasis with sun loungers offers relaxation after exploring nearby shopping and dining options.

NT$3,210 total

includes taxes & fees

Nov 3 - Nov 4

A swimming pool with lounge chairs and umbrellas, a building with multiple windows, and palm trees.

6. La Quinta Inn & Suites by Wyndham Orlando UCF

Orlando

Sun-soaked outdoor pool offers refreshing escapes and hot tub relaxation near the University of Central Florida campus.

NT$3,241 total

includes taxes & fees

Nov 1 - Nov 2

A pool area with lounge chairs, a table, and umbrellas.

7. Holiday Inn Express Orlando International Airport by IHG

Orlando

NT$3,556 total

includes taxes & fees

Nov 24 - Nov 25

A swimming pool with a brick border, surrounded by a fence and trees.

8. Hyatt Place Lake Mary/Orlando North

Lake Mary

Spacious outdoor pool and hot tub create a relaxing oasis with nearby recreational activities in this centrally located hotel.

NT$3,498 total

includes taxes & fees

Nov 22 - Nov 23

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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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Clean , spacious quiet"

Universal's Cabana Bay Beach Resort

10/10 Excellent

"I have so many good things to say about this hotel and the staff. They are all absolutely incredible. Very friendly and helpful. Lots of food options for families, the bars are great, and Lost and Found saved my life by finding my work phone that was left behind! We will 100% be back!"

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Hotel was perfectly located by Universal Studios. The staff was very friendly, rooms were always clean and the complimentary shuttle service was so helpful! We had a great view of the parks too, and you could even see the fireworks some nights :) We unfortunately didnt take advantage of the pool that was there but hopefully we will when we book for our orlando trip again!"

Holiday Inn Resort Orlando Suites - Waterpark by IHG

8/10 Good

"Staff was friendly. Any messes in common areas were cleaned up quickly. The pool/waterpark area alone made it worth the price. We didn’t use the arcade but it looked nice. Pizza from the restaurant was good. Only complaints, shower water pressure was very weak & the vent covers were rusted and dusty."

Hyatt Regency Orlando International Airport

10/10 Excellent

"I found the hotel very convenient as it was located at our TSA gate in the Orlando airport. They were very kind at check-in and very helpful when I ask about an upgrade overall the rooms were clean. The personnel was pleasant and kind and the location was convenient so I give it a 10 out of 10 stars."

Frequently asked questions

What are some accommodations with pools in Winter Park?

Hyatt Regency Orlando International Airport: Features 2 restaurants, an outdoor pool, and complimentary wireless internet access. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Aparthotel located near Orlando Vineland Premium Outlets. Offers 6 outdoor pools, a children's pool, and 3 restaurants. Marriott's Grande Vista: Aparthotel located near Orlando Vineland Premium Outlets. Provides 4 outdoor pools, a children's pool, and 3 restaurants. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Features a lazy river, 2 outdoor pools, and 2 restaurants. Avanti International Resort: Hotel, 9-minute walk from Pointe Orlando. Offers a children's pool, a seasonal outdoor 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 Orange County Convention Center while you're in the area. Spend some time experiencing the great outdoors at Albin Polasek Museum and Sculpture Gardens and Lake Mizell. 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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