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

Winter Park Hotels with Swimming Pool

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Check availability on Winter Park Hotels with Swimming Pools

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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 lobby with a high ceiling, large windows, and a grand piano.
A hotel with multiple floors, outdoor seating areas, and a well-lit courtyard.

1. The Alfond Inn

The Alfond Inn
Winter Park
  • Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
RM1,209
RM1,484 total
includes taxes & fees
1 Nov - 2 Nov
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 hotel room with two beds, a blue sofa, a wooden table, and framed pictures on the wall.
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 city centre Orlando with this hotel's seasonal outdoor pool and relaxing hot tub for post-exploration recovery.
RM567
RM638 total
includes taxes & fees
25 Oct - 26 Oct
Comfort Suites Downtown
A swimming pool with wooden deck seating, palm trees, and a modern building in the background.
Restaurant
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.

3. Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown
Ivanhoe Village
  • Float in sunshine at city centre Orlando's chic hotel pool, surrounded by plush loungers and umbrellas.
RM517
RM582 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Orlando Downtown
A hotel pool area with lounge chairs, umbrellas, and a swimming pool.
An outdoor seating area with green chairs and umbrellas, a fire pit, and a building with large windows in the background.
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.

4. Hampton Inn & Suites Orlando Airport @ Gateway Village

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.
RM413
RM465 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn & Suites Orlando Airport @ Gateway Village
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 reception area with a pool view mural, two reception desks, and a waiting area with chairs.
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.

5. 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.
RM361
RM406 total
includes taxes & fees
1 Nov - 2 Nov
La Quinta Inn & Suites by Wyndham Orlando UCF
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 bathroom with a granite countertop, a sink, a mirror, a framed picture, and a shower curtain.

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.
RM364
RM410 total
includes taxes & fees
27 Oct - 28 Oct
Wingate by Wyndham - Orlando International Airport
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence and palm trees.
A modern living room with a stone fireplace, a sofa, a coffee table, and a lamp.
A modern hotel dining area with multiple tables and chairs, a central bar area, and a kitchen in the background.
A hotel room with two beds, a desk, and two lamps.

7. Fairfield Inn By Marriott Orlando Airport

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.
RM344
RM386 total
includes taxes & fees
25 Oct - 26 Oct
Fairfield Inn By Marriott Orlando Airport
A swimming pool with lounge chairs and umbrellas, surrounded by a multi-story building with balconies.
A modern bar area with a long counter, bar stools, and a seating area with tables and chairs.
A hotel room with two beds, a desk, a chair, a lamp, and two paintings on the wall.
A modern hotel with a blue facade, a covered entrance, and palm trees in the foreground.

8. 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.
RM498
RM560 total
includes taxes & fees
2 Nov - 3 Nov
Hyatt House Orlando Airport
A pool area with lounge chairs, a table, and umbrellas.
A modern lobby with a checkered carpet, seating area, and a reception desk.
A self-service beverage area with refrigerated drink dispensers, snack shelves, and a water cooler.
A modern lobby with seating areas, a patterned pillar, and hanging light fixtures.

9. Holiday Inn Express Orlando International Airport by IHG

Holiday Inn Express Orlando International Airport by IHG
Orlando
RM396
RM446 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Orlando International Airport by IHG
A hotel with a swimming pool, lounge chairs, and palm trees.
A spacious lobby with a wooden staircase, a reception desk, and a large wall clock.
A modern dining area with a central island, wooden chairs, and large windows with blinds.
A large hotel with a prominent entrance, multiple floors, and a covered area with palm trees.

10. Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL
Airport North
  • Refreshing airport oasis beckons with a sparkling outdoor pool and relaxing hot tub retreat.
RM295
RM332 total
includes taxes & fees
27 Oct - 28 Oct
Country Inn & Suites by Radisson, Orlando Airport, FL
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

10/10 Excellent
"100 % recommended πŸ‘ πŸ‘"
Karen a. 1-night trip
Posted 1 hour ago
Universal's Cabana Bay Beach Resort
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Been staying here for years love EVERYTHING about it"
Colleen 1-night trip
Posted 3 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"It's a very practical hotel when passing through Orlando. Clean, secure and decently priced."
Karem 1-night trip
Posted 4 hours ago
Hyatt Regency Orlando International Airport
DoubleTree by Hilton Orlando Theme Park Resort

DoubleTree by Hilton Orlando Theme Park Resort

10/10 Excellent
"This hotel is perfect for theme park stays! Breakfast is delicious, rooms are nice, comfortable and cozy!!!! Staff were amazing, very helpful and friendly."
Juan 1-night trip
Posted 5 hours ago
DoubleTree by Hilton Orlando Theme Park Resort
Courtyard by Marriott across Universal Orlando

Courtyard by Marriott across Universal Orlando

8/10 Good
"Very busy location and they have a great location. Breakfast is so weird and takes 40-50 minutes just to get. You get a voucher and a coffee shop thing with one person takes your order then you wait forever. They give you things like coffee but you ask for creamer after they help the next few people and its like a challenge because they just have one small serving area. Skip Breakfast and you will save alot of time."
dirk 1-night trip
Posted 5 hours ago
Courtyard by Marriott across Universal Orlando
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Our favorite off property hotel! Free breakfast( Mickey waffles are delish), KickBack snack buffet and 3 complimentary drinks are a wonderful,inviting perk as well.The rooms are always clean and comfortable,and the shuttle service is always on time!."
Dustin 3-night trip
Posted 6 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent
"Outstanding place to stay we stayed before as well to rest from the parks . It’s easy to uber around to parks or Disney springs est cost around 9.00 a trip , the hotel also offers a bus but sometimes it’s convenient to urbor"
michael 1-night trip
Posted 7 hours ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village
Avanti International Resort

Avanti International Resort

8/10 Good
"I always have a nice experience here"
Michelle 4-night trip
Posted 9 hours ago
Avanti International Resort
Marriott's Grande Vista

Marriott's Grande Vista

8/10 Good
"Emplacement"
Daniel 2-night trip
Posted 9 hours ago
Marriott's Grande Vista

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. Marriott's Grande Vista: Aparthotel located near Orlando Vineland Premium Outlets. Provides 4 outdoor swimming 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 swimming 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 such as 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. 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 28Β°C, while the coldest months are January and February, with an average of 18Β°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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