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

Winter Park Hotel Guide - Hotels with Pool in Winter Park, Orlando

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Check availability on Winter Park Hotels with Pool

Tonight
4 Oct - 5 Oct
Tomorrow
5 Oct - 6 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

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 lobby with a high ceiling, large windows, and a grand piano.
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.

1. The Alfond Inn

The Alfond Inn
Winter Park
  • Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
€321
includes taxes & fees
5 Oct - 6 Oct
The Alfond Inn
Pool
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.
A dining table with four chairs, each with a white doily and a yellow plate.
A modern kitchen with white cabinets, stainless steel appliances, and a black dining chair.

2. 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
€259
includes taxes & fees
9 Oct - 10 Oct
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 shower with a glass door, a white shower curtain, and a black floor mat.
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.

3. 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.
€156
includes taxes & fees
2 Nov - 3 Nov
1-bedroom vacation room just 12 minutes from University of Central Florida
A covered outdoor swimming pool with lounge chairs and a metal frame structure.
A dining area with a wooden table and wicker chairs, a grey sofa, and a television mounted on the wall.
A spacious room with a foosball table, a ceiling fan, and a bed in the background.
Living area

4. Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park Charmer - Heated Pool Home - Close to everything
Winter Park
€356
includes taxes & fees
6 Oct - 7 Oct
Winter Park Charmer - Heated Pool Home - Close to everything
A pool area with a hot tub, lounge chairs, and a covered seating area.
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.
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.
€125
includes taxes & fees
11 Oct - 12 Oct
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.
Restaurant
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.
€118
includes taxes & fees
15 Oct - 16 Oct
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.
€87
includes taxes & fees
18 Oct - 19 Oct
La Quinta Inn & Suites by Wyndham Orlando UCF
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.

8. 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.
€82
includes taxes & fees
5 Oct - 6 Oct
Wingate by Wyndham - Orlando International Airport
An aerial view of a resort with multiple swimming pools, landscaped gardens, and outdoor seating areas.
A spacious hotel lobby with a central staircase, multiple seating areas, and large windows offering views of the outdoor area.
A spacious lobby with high ceilings, arched columns, and a mix of seating areas.
A large hotel with multiple floors, surrounded by a well-maintained golf course and a lake.

9. Rosen Shingle Creek

Rosen Shingle Creek
Orlando
  • Swim in luxury with four sparkling pools and poolside cabanas at this golf resort haven.
€119
includes taxes & fees
30 Oct - 31 Oct
Rosen Shingle Creek
A pool area with lounge chairs, a table, and umbrellas.
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.
A modern lobby with a checkered carpet, seating area, and a reception desk.

10. Holiday Inn Express Orlando International Airport by IHG

Holiday Inn Express Orlando International Airport by IHG
Orlando
€93
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn Express Orlando International Airport by IHG
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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

8/10 Good
"The place is great but you charge for a security deposit a little high and the parking fee a night is crazy but other than that I had a great time!"
Michael 3-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"Lovely place to stay"
Pamela J 4-night trip
Posted less than an hour ago
Marriott's Grande Vista
Buena Vista Suites Orlando

Buena Vista Suites Orlando

8/10 Good
"Bathroom cleanliness was a bit lacking and could also use updating. Staff was fantastic."
Paula 3-night trip
Posted less than an hour ago
Buena Vista Suites Orlando
Courtyard by Marriott across Universal Orlando

Courtyard by Marriott across Universal Orlando

10/10 Excellent
"Excelent"
FABIAN 2-night trip
Posted less than an hour ago
Courtyard by Marriott across Universal Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"Overall I'm impressed with my stay in this hotel."
ANA 1-night trip
Posted 1 hour ago
Hyatt Regency Orlando International Airport
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Todo perfecto. Habitación cómoda. Hotel seguro. Hermosa zona"
Paolo 2-night trip
Posted 1 hour ago
Rosen Inn Lake Buena Vista
DoubleTree by Hilton Orlando Theme Park Resort

DoubleTree by Hilton Orlando Theme Park Resort

10/10 Excellent
"I really enjoyed my stay was for one day due to a convention 3 minutes from there. From check in to check out everything was on spot."
omar 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Orlando Theme Park Resort
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Our room was clean and big was remodeled staff was very nice and helpful will stay again our next time in Orlando"
Michael 3-night trip
Posted 1 hour ago
Westgate Lakes Resort & Spa Universal Studios Area
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

8/10 Good
"The front desk staff were very helpful. Good options for breakfast."
Kristen 2-night trip
Posted 3 hours ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

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.