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

Winter Park Hotel with Pool

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Check availability on Winter Park Hotel with Pool

Tonight
23 Sept - 24 Sept
Tomorrow
24 Sept - 25 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 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 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.

1. The Alfond Inn

The Alfond Inn
Winter Park
  • Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
HK$2,111
HK$2,613 total
includes taxes & fees
27 Sept - 28 Sept
The Alfond Inn
A rectangular swimming pool with clear blue water, surrounded by a beige deck and a white fence.
A bedroom with a bed, bedside tables, a mirror, and a ceiling fan.
A modern kitchen with white cabinets, a dining area with a table set for four, and a large window.
A modern living room with a ceiling fan, a flat-screen TV, and a dining area with a white table and chairs.

2. The Canopy on Periwinkle- A Home Away From Home

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
HK$1,012
HK$2,832 total
includes taxes & fees
24 Sept - 25 Sept
The Canopy on Periwinkle- A Home Away From Home
A modern kitchen with white cabinets, stainless steel appliances, and a black dining chair.
A residential house with a paved driveway, solar panels on the roof, and a well-maintained lawn.
A modern living room with a beige sofa, a black office chair, a small side table with a lamp, and a ceiling fan.
A bathroom with a shower, toilet, and a white sink with a mirror above it. There are potted plants on a metal shelf above the sink.

3. Quiet and safe neighborhood come to this great place with lots of room for relax

Quiet and safe neighborhood come to this great place with lots of room for relax
Orlando
HK$1,045
HK$2,293 total
includes taxes & fees
24 Sept - 25 Sept
Quiet and safe neighborhood come to this great place with lots of room for relax
A swimming pool with a curved edge, surrounded by a concrete deck and a brick border.
A bedroom with a bed, a nightstand, a lamp, and a ceiling fan.
An outdoor air conditioning unit mounted on a yellow wall, a brick planter with a potted plant, and a white door.
A covered patio area with outdoor furniture, a grill, and potted plants.

4. 1-bedroom vacation room just 12 minutes from University of Central Florida

1-bedroom vacation room just 12 minutes from University of Central Florida
Orlando
  • Relax poolside at a cosy retreat with both private and outdoor pools, just 12 minutes from University of Central Florida.
HK$417
HK$1,287 total
includes taxes & fees
4 Oct - 5 Oct
1-bedroom vacation room just 12 minutes from University of Central Florida
A pool area with a hot tub, lounge chairs, and a covered seating area.
A hotel entrance with a covered area, palm trees, and an American flag.
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.

5. 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.
HK$956
HK$1,076 total
includes taxes & fees
27 Sept - 28 Sept
Comfort Suites Downtown
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.
A multi-story hotel with a modern design, featuring balconies and a covered entrance.

6. 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.
HK$994
HK$1,118 total
includes taxes & fees
28 Sept - 29 Sept
Courtyard by Marriott Orlando 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.

7. 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.
HK$693
HK$780 total
includes taxes & fees
30 Sept - 1 Oct
La Quinta Inn & Suites by Wyndham Orlando UCF
A hotel pool area with a large pool, lounge chairs, and a building with multiple windows and balconies.
A hotel room with a bed, a desk, a chair, a sofa, and a TV.
A hotel with a prominent tower, palm trees, and a red roof.
A buffet area with a microwave, coffee maker, and various food containers.

8. La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport
Airport North
  • Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.
HK$524
HK$589 total
includes taxes & fees
1 Oct - 2 Oct
La Quinta Inn & Suites by Wyndham Orlando Airport
A hot tub with a waterfall mural, a metal ladder, and a tiled floor.
A bathroom with a granite countertop, a sink, a mirror, a framed picture, and a shower curtain.
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.

9. 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.
HK$634
HK$713 total
includes taxes & fees
29 Sept - 30 Sept
Wingate by Wyndham - Orlando International Airport
A reception area with a curved wooden counter, a glass display case with beverages, and a wall mural with a wave pattern.
A modern bathroom with a bathtub, toilet, and sink.
A Hyatt Place hotel entrance with a covered walkway, glass doors, and a landscaped area with trees and shrubs.
A hotel room with a sofa, two beds, a TV, a window with a view, and a bathroom.

10. 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.
HK$713
HK$823 total
includes taxes & fees
24 Sept - 25 Sept
Hyatt Place Lake Mary/Orlando North
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

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

8/10 Good
"I had problem with meals and housekeeping but was dealt accordingly however there lots to improve with cleanliness and F&b service and food feedbacks where share to general manager hope they will improve."
paulo 6-night trip
Posted 2 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"The room and bath were very clean, bed was very comfortable and staff very helpful."
Beatriz 1-night trip
Posted 4 hours ago
Hyatt Regency Orlando International Airport
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Great place to stay with the family."
Vanessa 7-night trip
Posted 11 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"All was excellent."
Vanessa 6-night trip
Posted 12 hours ago
Marriott's Grande Vista
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Nice place to stay and very convenient."
Angie 4-night trip
Posted 16 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

8/10 Good
"Everything was good except for the fact that the parking was full on Friday night and Saturday night but other than that everything else was amazing we had such a great time I would definitely book again"
Pennee 3-night trip
Posted 22 hours ago
Lake Buena Vista Resort Village & Spa

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 Endless Summer Resort - Dockside Inn and Suites: Hotel located near Universal Orlando Resort. Features 2 outdoor swimming 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 swimming pools and 2 restaurants.
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 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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