TOP Hotels with Pool in Winter Park, FL for 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 spacious hall with a grand piano, large windows, and a central floral arrangement.

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.

Rp4.271.128

Rp5.340.983 total

includes taxes & fees

6 Sept - 7 Sept

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

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.

A hotel room with a blue sofa, a wooden desk, a TV, and a lamp.

2. Comfort Suites Downtown

Ivanhoe Village

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

Rp2.045.413

Rp2.301.089 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

3. Courtyard by Marriott Orlando Downtown

Ivanhoe Village

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

Rp2.159.381

Rp2.429.304 total

includes taxes & fees

7 Sept - 8 Sept

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

A reception area with a pool view mural, two reception desks, and a waiting area with chairs.

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.

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.

Rp1.439.587

Rp1.619.535 total

includes taxes & fees

13 Sept - 14 Sept

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

A modern hotel room with a large white bathtub, a neatly made bed, and a small bedside table with a lamp.

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.

Rp1.349.613

Rp1.518.271 total

includes taxes & fees

7 Sept - 8 Sept

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

A multi-story hotel with a prominent red sign, a well-lit entrance, and a landscaped front yard.

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

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

6. Hampton Inn & Suites Orlando Airport @ Gateway Village

Airport North

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

Rp1.580.856

Rp1.778.463 total

includes taxes & fees

13 Sept - 14 Sept

A swimming pool with lounge chairs and umbrellas, surrounded by a white fence and palm trees.

A hotel room with two beds, a desk, and two lamps.

A hotel room with a wooden desk, a flat-screen TV, a lamp, a chair, a small cabinet, and a trash bin.

A modern hotel dining area with multiple tables and chairs, a central bar area, and a kitchen in the background.

7. Fairfield Inn By Marriott Orlando Airport

Airport North

Splash into this refreshing outdoor retreat with crystal-clear waters and a rejuvenating hot tub after airport arrivals.

Rp1.484.574

Rp1.670.145 total

includes taxes & fees

7 Sept - 8 Sept

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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

Coco Key Hotel & Water Park Resort

10/10 Excellent

"Great spot. Great updated room. Kids loved the water slides."

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"Great place to stay ."

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"This was possibly one of our best stays in Orlando and we go every other year. This hotel has great amenities catering towards families visiting for amusement parks. Breakfast and the kickback were huge perks since food can get so expensive at the parks."

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Value for money!! A great option close to the Disney resorts without having to pay Disney Resort rates! Very spacious - the pools were EXCELLENT! A fantastic property that offers privacy and convenience just outside of Disney"

Hyatt Regency Orlando International Airport

10/10 Excellent

"It was my first stay though I have passed through the Orlando airport many times over the years. I was surprised that there was no access to the balcony. I was looking forward to looking out."

Caribe Royale Orlando, WorldHotels Elite

10/10 Excellent

"Best hotel"

Marriott's Grande Vista

10/10 Excellent

"The staff was very helpful and friendly. The rooms and the property was superb all around. Close to the parks and shopping area. Will be staying again."

Rosen Inn Lake Buena Vista

10/10 Excellent

"I always stay here safe clean staff is wounderful"

Universal's Cabana Bay Beach Resort

10/10 Excellent

"This place was AMAZING!!! Our kids had so much fun in the pools, slides and hot tub. There was plenty of options for food at affordable prices. The kids are already talking about going back to the same place next year. Highly recommend staying at Cabana Bay Beach resort!!"

Frequently asked questions

What are some accommodation options 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 swimming pools, a children's pool and 3 restaurants. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Provides a lazy river, 2 outdoor swimming pools and 2 restaurants. Marriott's Grande Vista: Aparthotel located near Orlando Vineland Premium Outlets. Features 4 outdoor swimming pools, a children's pool and 3 restaurants. Universal's Endless Summer Resort - Dockside Inn and Suites: Hotel located near Universal Orlando Resort. Offers 2 outdoor swimming pools, a children's pool and 3 bars.

What is there to see and do in Winter Park?

Explore places such as 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. 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.

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Change your mind

Treat yourself

Be picky

Check availability on Winter Park Hotels with Pool

Our top choices for Winter Park hotels with a pool

1. The Alfond Inn

2. Comfort Suites Downtown

3. Courtyard by Marriott Orlando Downtown

4. La Quinta Inn & Suites by Wyndham Orlando UCF

5. Wingate by Wyndham - Orlando International Airport

6. Hampton Inn & Suites Orlando Airport @ Gateway Village

7. Fairfield Inn By Marriott Orlando Airport

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

Top Winter Park Hotel Reviews

Coco Key Hotel & Water Park Resort

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Drury Plaza Hotel Orlando - Disney Springs Area

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Hyatt Regency Orlando International Airport

Caribe Royale Orlando, WorldHotels Elite

Marriott's Grande Vista

Rosen Inn Lake Buena Vista

Universal's Cabana Bay Beach Resort

Frequently asked questions

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