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

Find Hotels with a Pool in Winter Park, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Park Hotels with a Pool

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Winter Park hotels with a pool

A multi-story hotel with balconies, a swimming pool, and a landscaped courtyard.
A spacious hall with a grand piano, large windows, and a central floral arrangement.
A hotel with multiple floors, outdoor seating areas, and a well-lit courtyard.
An outdoor dining area with tables and chairs, string lights, and a building with arches and balconies.

1. The Alfond Inn

The Alfond Inn
Winter Park
  • Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
NT$7,661
NT$9,580 total
includes taxes & fees
Sep 13 - Sep 14
The Alfond Inn
A pool area with a hot tub, lounge chairs, and a covered seating area.
A hotel room with a blue sofa, a wooden desk, a TV, and a lamp.
A spacious lobby with a reception desk, seating area with sofas and armchairs, and large windows allowing natural light.
A hotel entrance with a covered area, palm trees, and an American flag.

2. Comfort Suites Downtown

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$3,816
NT$4,293 total
includes taxes & fees
Sep 21 - Sep 22
Comfort Suites Downtown
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.
A modern living room with a large flat-screen TV, blue sofas, a round coffee table, and a bookshelf.

3. Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown
Ivanhoe Village
  • Float in sunshine at downtown Orlando's chic hotel pool, surrounded by plush loungers and umbrellas.
NT$3,996
NT$4,495 total
includes taxes & fees
Sep 20 - Sep 21
Courtyard by Marriott Orlando Downtown
A swimming pool with lounge chairs and umbrellas, a building with multiple windows, and palm trees.
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 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.

4. La Quinta Inn & Suites by Wyndham Orlando UCF

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$2,789
NT$3,138 total
includes taxes & fees
Sep 14 - Sep 15
La Quinta Inn & Suites by Wyndham Orlando UCF
A reception area with a curved wooden counter, a glass display case with beverages, and a wall mural with a wave pattern.
A modern interior with two blue armchairs, a small wooden table, and a large window offering a view of palm trees.
A hotel room with a sofa, two beds, a TV, a window with a view, and a bathroom.
A modern bathroom with a bathtub, toilet, and sink.

5. Hyatt Place Lake Mary/Orlando North

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$2,953
NT$3,407 total
includes taxes & fees
Sep 14 - Sep 15
Hyatt Place Lake Mary/Orlando North
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 restaurant with multiple dining tables and chairs, a bar area, and a television mounted on the wall.
A modern lounge area with a sofa set, ottomans, and a small table.

6. Wingate by Wyndham - Orlando International Airport

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$2,636
NT$2,965 total
includes taxes & fees
Sep 21 - Sep 22
Wingate by Wyndham - Orlando International Airport
View all properties

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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Our stay was so amazing I got sucked into the timeshare spiel for a future trip 😄 I legit wish I could live here and my kids didn't want to leave either, the pools were amazing. We'll definitely be back, I highly highly recommend!"
Selena 3-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"The experience was truly impeccable. The room itself was up to standard and incredibly comfortable and clean. The staff were welcoming and very understanding. As well as, the pool amenities were enjoyable. The poolside staff doing the activities were also very friendly people. Overall I had a great time, would definitely recommend."
Yodilaine 2-night trip
Posted 2 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Nos encanta este hotel, el trato excelente, la comida deliciosa, cerca de todo, siempre lo elegimos."
Maripaz 3-night trip
Posted 2 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite

10/10 Excellent
"Exceptional"
soucarina 3-night trip
Posted 5 hours ago
Caribe Royale Orlando, WorldHotels Elite

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. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Provides a lazy river, 2 outdoor pools, and 2 restaurants. Marriott's Grande Vista: Aparthotel located near Orlando Vineland Premium Outlets. Features 4 outdoor 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 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.

Explore a world of travel with Expedia