The Best Hotels with a Pool in Winter Park, FL from ₩103,201 in 2026

A two-story house with a balcony, surrounded by lush greenery and trees.

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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.

An outdoor dining area with tables and chairs, string lights, and a building with arches and balconies.

A hotel with multiple floors, outdoor seating areas, and a well-lit courtyard.

A spacious lobby with a high ceiling, large windows, and a grand piano.

1. The Alfond Inn

Winter Park

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

₩305,290

₩385,529 total

includes taxes & fees

Sep 10 - Sep 11

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

A multi-story hotel with a modern design, featuring balconies and a covered entrance.

An outdoor patio area with wicker furniture, a glass table, and a view of a building in the background.

A modern living room with a large flat-screen TV, blue sofas, a round coffee table, and a bookshelf.

2. Courtyard by Marriott Orlando Downtown

Ivanhoe Village

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

₩169,358

₩190,527 total

includes taxes & fees

Aug 29 - Aug 30

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

A hotel entrance with a covered area, palm trees, and an American flag.

A hotel room with two beds, a blue sofa, a wooden table, and framed pictures on the wall.

A spacious lobby with a reception desk, seating area with sofas and armchairs, and large windows allowing natural light.

3. 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.

₩156,289

₩175,824 total

includes taxes & fees

Aug 30 - Aug 31

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

A hotel room with a bed, desk, chair, and a sofa.

A hallway with a dark wood console table, a green vase, and framed artwork on the wall. A sign indicates the direction to the fitness center, ice machine, and AV room.

A modern living room with a sofa, chairs, a fireplace, and a flat-screen TV mounted on the wall.

4. 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.

₩112,905

₩127,018 total

includes taxes & fees

Sep 13 - Sep 14

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

A bathroom with a granite countertop, a sink, a mirror, a framed picture, and a shower curtain.

A modern lounge area with a sofa set, ottomans, and a small table.

A modern restaurant with multiple dining tables and chairs, a bar area, and a television mounted on the wall.

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.

₩91,735

₩103,201 total

includes taxes & fees

Sep 21 - Sep 22

A swimming pool with lounge chairs and palm trees, surrounded by a building with large windows.

Two high-rise buildings with reflections in a calm body of water, surrounded by greenery and palm trees.

An outdoor pool area with a covered seating area, surrounded by palm trees and a modern building in the background.

A hotel room with two beds, a desk, a TV, and a large window with a view.

6. DoubleTree by Hilton at the Entrance to Universal Orlando

Florida Center

Splash into Florida sunshine at the entrance to Universal Orlando with a poolside cocktail and refreshing hot tub.

₩98,031

₩110,286 total

includes taxes & fees

Sep 2 - Sep 3

A hotel pool area with lounge chairs, umbrellas, and a swimming pool.

A hotel room with a sofa, two armchairs, a coffee table, and a wall-mounted sign reading "gateway village - ORLANDO stay a while".

An outdoor seating area with green chairs and umbrellas, a fire pit, and a building with large windows in the background.

A bar area with a long counter, multiple seating options, and a television screen.

7. 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.

₩117,997

₩132,747 total

includes taxes & fees

Aug 31 - Sep 1

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Choose what matters most at hotels with a pool in Winter Park

Breakfast included

4 stars

Hot tub

5 stars

Spa

Top Winter Park Hotel Reviews

Universal's Cabana Bay Beach Resort

10/10 Excellent

"I have been there more than 5 times, and still love this resort. The only i thing they should get a little better is the food, maybe more variety and incrase the quality of food, but everything else, its awesome !!!! My son love it !!!!"

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"We love our stays here. Always clean and comfortable. Love all the amenities and convenient location."

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"Excellent location with easy walking access to Disney Springs. The bus service was frequent, reliable, and very convenient. The hotel was modern, very clean, and well maintained. We especially enjoyed the great breakfast and afternoon snack selection. The staff were friendly, welcoming, and very helpful. Overall, a fantastic stay!"

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent

"We loved it, it was our second time… we will be back!!!"

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"My son loved the pool and it’s so convenient to get things u need close by if you don’t have a car loved my stay here"

Residence Inn by Marriott Orlando Lake Buena Vista

10/10 Excellent

"Everything was good. From the friendly staff, breakfast and cleanliness."

Marriott's Grande Vista

8/10 Good

"Everything was great the only problem is that they charge me $30 a night for parking it’s not much but still."

Wyndham I-Drive Avanti Resort & Conference Center

10/10 Excellent

"nice people nice staff, I would come back"

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"Everything was excellent"

Frequently asked questions

What are some accommodations with pools in Winter Park?

Rosen Inn Lake Buena Vista: Hotel located near Disney Springs™. Features 2 outdoor pools, a children's pool, and a snack bar/deli. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 3-minute walk from Universal Orlando Resort. Offers a children's pool, an outdoor pool, and 2 restaurants. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Aparthotel located near Orlando Vineland Premium Outlets. Provides 6 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. Universal's Endless Summer Resort - Dockside Inn and Suites: Hotel located near Universal CityWalk. Offers 2 outdoor pools, a children's pool, and 3 bars.

What is there to see and do in Winter Park?

Explore places like Universal Studios Florida, Universal Orlando Resort, and Universal's Volcano Bay 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.

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Find Hotels with a Pool in Winter Park, FL

Change your mind

Treat yourself

Be picky

Check availability on Winter Park Hotels with a Pool

Our top choices for Winter Park hotels with a pool

1. The Alfond Inn

2. Courtyard by Marriott Orlando Downtown

3. Comfort Suites Downtown

4. La Quinta Inn & Suites by Wyndham Orlando UCF

5. Wingate by Wyndham - Orlando International Airport

6. DoubleTree by Hilton at the Entrance to Universal Orlando

7. Hampton Inn & Suites Orlando Airport @ Gateway Village

Choose what matters most at hotels with a pool in Winter Park

Top Winter Park Hotel Reviews

Universal's Cabana Bay Beach Resort

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Drury Plaza Hotel Orlando - Disney Springs Area

Holiday Inn Resort Orlando Suites - Waterpark by IHG

DoubleTree by Hilton at the Entrance to Universal Orlando

Residence Inn by Marriott Orlando Lake Buena Vista

Marriott's Grande Vista

Wyndham I-Drive Avanti Resort & Conference Center

Westgate Lakes Resort & Spa Universal Studios Area

Frequently asked questions

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