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

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Check availability on Winter Park Hotels with Pool

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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 hall with a grand piano, large windows, and a central floral arrangement.

1. The Alfond Inn

The Alfond Inn
Winter Park
  • Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
฿9,881
฿12,135 total
includes taxes & fees
25 Oct - 26 Oct
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 city centre Orlando with this hotel's seasonal outdoor pool and relaxing hot tub for post-exploration recovery.
฿4,380
฿4,927 total
includes taxes & fees
18 Oct - 19 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.
฿4,247
฿4,777 total
includes taxes & fees
15 Oct - 16 Oct
Courtyard by Marriott Orlando Downtown
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 bathroom with a granite countertop, a sink, a mirror, a framed picture, and a shower curtain.

4. 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.
฿2,876
฿3,235 total
includes taxes & fees
14 Oct - 15 Oct
Wingate by Wyndham - Orlando International Airport
A swimming pool with lounge chairs and umbrellas, surrounded by a multi-story building with balconies.
An outdoor patio area with seating, a bar, and a fire feature.
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.

5. 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.
฿4,124
฿4,640 total
includes taxes & fees
3 Nov - 4 Nov
Hyatt House Orlando Airport
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 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.

6. 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.
฿2,964
฿3,335 total
includes taxes & fees
19 Oct - 20 Oct
La Quinta Inn & Suites by Wyndham Orlando UCF
A pool area with lounge chairs and canopies, surrounded by palm trees.
A modern hotel with a glass facade, outdoor seating, and a clear sky.
A spacious indoor area with a large central island, multiple seating arrangements, and a high ceiling with a skylight.
A modern hotel with a glass facade, palm trees, and a sign reading "DoubleTree by Hilton."

7. DoubleTree by Hilton Orlando Airport

DoubleTree by Hilton Orlando Airport
Airport North
  • Dive into sun-kissed relaxation with a perfect outdoor pool oasis in this airport-adjacent retreat.
฿3,272
฿3,681 total
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Orlando Airport
A pool area with lounge chairs, a table, and umbrellas.
A coffee station with espresso machines, a yogurt dispenser, and a fruit display.
A self-service beverage area with refrigerated drink dispensers, snack shelves, and a water cooler.
A modern lobby with a checkered carpet, seating area, and a reception desk.

8. Holiday Inn Express Orlando International Airport by IHG

Holiday Inn Express Orlando International Airport by IHG
Orlando
฿3,521
฿3,961 total
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Express Orlando International Airport by IHG
A swimming pool with a brick border, surrounded by a fence and trees.
A bathroom with a shower, grab bars, a towel rack, and a toilet.
A beverage refrigerator stocked with various drinks and a shelf with snacks and chips.
A modern kitchen with a breakfast bar, wooden cabinets, and a view of the outdoors.

9. 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.
฿3,128
฿3,609 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Lake Mary/Orlando North
A hotel atrium with a central fountain, palm trees, and a circular seating area.
A spacious lobby with a high ceiling, large windows, and potted plants.
A modern restaurant with a panoramic view of the airport, featuring high ceilings, hanging spherical light fixtures, and a mix of seating arrangements.
A spacious lobby with high ceilings, large windows, and potted plants.

10. Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport
Orlando
  • Tropical poolside oasis at an airport hotel offers relaxing moments surrounded by sunshine, just steps away from departure gates.
฿7,343
฿8,261 total
includes taxes & fees
2 Nov - 3 Nov
Hyatt Regency 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

Buena Vista Suites Orlando

Buena Vista Suites Orlando

10/10 Excellent
"This hotel is in a great location. The room size is very roomy, not to mention very clean. Even when you walk the hallways, the fragrance was always nice. The staff was great to interact with, and very helpful when something was needed."
Peter 2-night trip
Posted 2 hours ago
Buena Vista Suites Orlando
Courtyard by Marriott across Universal Orlando

Courtyard by Marriott across Universal Orlando

10/10 Excellent
"It is a nice place!"
J Andres 1-night trip
Posted 2 hours ago
Courtyard by Marriott across Universal Orlando
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

8/10 Good
"Great place to stay! Manager at front desk was so good w kids! Breakfast and kickback reception in the evening was surprisingly tasty for free food! Even on a sold out weekend and how busy it was I never had to wait in line for plate or fork at breakfast. Props to the team! I think the only downfall is the bus stops at two parks and it could take a while when ur the 2nd drop off! You really have to leave an hour earlier than u think!"
Kristen 4-night trip
Posted 3 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
DoubleTree by Hilton Orlando Theme Park Resort

DoubleTree by Hilton Orlando Theme Park Resort

10/10 Excellent
"everything was perfect"
Madison 4-night trip
Posted 3 hours ago
DoubleTree by Hilton Orlando Theme Park Resort
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

8/10 Good
"Room was humid. Breakfast needs more waffle stations."
Arthur 1-night trip
Posted 6 hours ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Front desk was professional and friendly. Convenient location for Disney Springs. Great security and very secure parking."
Deborah 3-night trip
Posted 9 hours ago
Rosen Inn Lake Buena Vista
Avanti International Resort

Avanti International Resort

10/10 Excellent
"Everything was nice hotel was good and great location"
Jennifer 6-night trip
Posted 9 hours ago
Avanti International 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. 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 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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