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

Hotels with Swimming Pool in Winter Park, Orlando

  • 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 Swimming Pool

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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.
P16,901
P20,921 total
includes taxes & fees
Sep 27 - Sep 28
The Alfond Inn
A swimming pool with wooden deck seating, palm trees, and a modern building in the background.
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

Courtyard by Marriott Orlando Downtown
Ivanhoe Village
  • Float in sunshine at downtown Orlando's chic hotel pool, surrounded by plush loungers and umbrellas.
P7,416
P8,343 total
includes taxes & fees
Sep 28 - Sep 29
Courtyard by Marriott Orlando Downtown
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 room with two beds, a blue sofa, a wooden table, and framed pictures on the wall.

3. 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.
P7,570
P8,516 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Suites Downtown
A swimming pool with lounge chairs and umbrellas, a building with multiple windows, and palm trees.
A modern living room with a sofa, chairs, a fireplace, and a flat-screen TV mounted on the wall.
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

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.
P5,549
P6,242 total
includes taxes & fees
Sep 27 - Sep 28
La Quinta Inn & Suites by Wyndham Orlando UCF
A hot tub with a waterfall mural, a metal ladder, and a tiled floor.
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.
A bathroom with a granite countertop, a sink, a mirror, a framed picture, and a shower curtain.

5. 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.
P5,031
P5,660 total
includes taxes & fees
Sep 23 - Sep 24
Wingate by Wyndham - Orlando International Airport
A swimming pool with lounge chairs and umbrellas, surrounded by a multi-story building with balconies.
A modern hotel with a blue facade, a covered entrance, and palm trees in the foreground.
A modern bar area with a long counter, bar stools, and a seating area with tables and chairs.
An outdoor patio area with seating, a bar, and a fire feature.

6. Hyatt House Orlando Airport

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.
P6,909
P7,772 total
includes taxes & fees
Sep 29 - Sep 30
Hyatt House Orlando Airport
A clear swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A modern hotel lobby with round tables and comfortable chairs, a bar area with shelves of bottles, and a kitchen area visible to the right.
A modern hotel lobby with a large flat-screen TV, a blue sofa, a round wooden table, and a curved reception desk.
A modern reception area with a curved counter, wooden bar stools, and pendant lighting.

7. Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
Orlando
  • Dive into poolside bliss near the airport where sunbathers sip cocktails on cushioned loungers under blue skies.
P6,161
P6,931 total
includes taxes & fees
Sep 23 - Sep 24
Cambria Hotel Orlando 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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

8/10 Good
"Great establishment for families looking for a getaway"
Kateya 2-night trip
Posted less than an hour ago
Universal's Cabana Bay Beach Resort
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Great amenities and great staff. Close to the dianey park and stores."
Hector 3-night trip
Posted 1 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
"."
Justin 3-night trip
Posted 9 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
"It’s a great hotel with a great breakfast and two every person who is over 21 receives two free drinks. The rooms are nice and roomy and clean"
Milagros 3-night trip
Posted 11 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Very bright and clean facilities. Easy walk to Universal City Walk."
Jessica 4-night trip
Posted 11 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

10/10 Excellent
"Me encanto"
José Miguel 2-night trip
Posted 15 hours ago
Wyndham I-Drive Avanti Resort & Conference Center
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent
"Nice stay we enjoyed it. We live the bunk beds for the kids and second TV"
Genaro 3-night trip
Posted 17 hours ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

8/10 Good
"We have been coming here for years. And noticed the furniture is becoming in need of replacement. Couch and chairs were terribly uncomfortable. We also understand lightening un area pool closes. But thr people working there were so rude on sunday. My daughter n her friend had bought a pretzel and were sitting under the awning due to rain to eat the pretzel and the bartender lso rudely told them they could not sit there the pool was closed and they had to leave. Mind u would u want a soggy pretzel after walking to your building in the rain. Also as everyone knows in florida rain and lightening come and go literally 40 mins later pool was reopened. And we were not thr only ppl complaing on their rudeness also he was literally making rude comment on a tip he received. It is a great getaway but be prepared the staff has gone down hill"
Jenny 4-night trip
Posted 17 hours ago
Lake Buena Vista Resort Village & Spa
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Clean and helpful staff"
Alejandra 1-night trip
Posted 20 hours ago
Rosen Inn Lake Buena Vista

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 Endless Summer Resort - Dockside Inn and Suites: Hotel located near Universal Orlando Resort. Features 2 outdoor pools, a children's pool, and 3 bars. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, and 2 restaurants.
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 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