Winter Park Hotels with Swimming Pool

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Pools

Tonight
22 Nov - 23 Nov
Tomorrow
23 Nov - 24 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

Top Winter Park Hotels with Swimming Pools

Outdoor pool, open 10:00 AM to 5:00 PM, pool umbrellas, pool loungers
The Alfond Inn

The Alfond Inn

4.0 star property
Winter Park
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.6 out of 10, Exceptional, (1001)
Poolside relaxation reaches new heights with comfortable loungers beneath shady umbrellas and refreshing drinks from the dedicated bar. After swimming, guests can rejuvenate in the steam room or enjoy indulgent spa treatments featuring aromatherapy.
The Alfond Inn
Outdoor pool, open 8:00 AM to 9:00 PM, pool cabanas (surcharge)
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

3.0 star property
International Drive District
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Hot tub
8.8 out of 10, Excellent, (609)
Poolside luxury awaits at this pristine retreat near Universal Studios. Families appreciate the dedicated children's pool, while adults relax in cabanas with cocktails from the poolside bar after invigorating workouts in the 24-hour fitness centre.
The price is RM314
RM353 total
includes taxes & fees
14 Dec - 15 Dec
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, pool umbrellas, pool loungers
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

3.0 star property
Orlando
  • Outdoor pool
  • Pool loungers
8.8 out of 10, Excellent, (1873)
Sparkling waters beckon at the sun-drenched outdoor pool, complete with loungers and shade umbrellas for post-adventure relaxation. Convenient shuttles to Disney and Universal parks make magical moments easily accessible from this comfortable Orlando haven.
The price is RM290
RM327 total
includes taxes & fees
25 Nov - 26 Nov
Aloft Orlando Lake Buena Vista
View from property
AC Hotel by Marriott Orlando Lake Buena Vista

AC Hotel by Marriott Orlando Lake Buena Vista

3.5 star property
Orlando
  • Outdoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (1622)
Swimming becomes a highlight at the pristine outdoor pool, accessible from morning until evening. Modern rooms complement the experience, while a 24-hour fitness centre, convenient theme park shuttle, and proximity to premium outlets enhance every stay.
The price is RM469
RM527 total
includes taxes & fees
16 Dec - 17 Dec
AC Hotel by Marriott Orlando Lake Buena Vista
Outdoor pool, open 9:00 AM to 9:00 PM, pool loungers
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3.0 star property
Kissimmee
  • Outdoor pool
  • Pool loungers
8.2 out of 10, Very good, (5152)
Sparkling blue waters beckon from the outdoor pool, surrounded by comfortable loungers for all-day relaxation. Guests appreciate hammock-dotted grounds, pristine lake views, and proximity to attractions. A game room and continental breakfast complete the experience.
Palazzo Lakeside Hotel
Outdoor pool, pool loungers
TRYP by Wyndham Orlando

TRYP by Wyndham Orlando

3.0 star property
International Drive District
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1018)
Cooling off becomes effortless in the pristine outdoor pool surrounded by comfortable sun loungers. Guests appreciate this well-maintained aquatic retreat after theme park adventures, complementing the 24-hour fitness centre and multilingual service.
The price is RM287
RM323 total
includes taxes & fees
11 Dec - 12 Dec
TRYP by Wyndham Orlando
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

4.5 star property
Orlando
  • 4 outdoor pools
  • Poolside bar
  • Pool loungers
  • 2 hot tubs
9.4 out of 10, Exceptional, (4260)
Swimming paradise unfolds across 4 inviting outdoor pools surrounded by swaying palms and luxurious cabanas. Refreshing poolside drinks complement sun-drenched days while nearby hot tubs offer evening relaxation after golf rounds on the 18-hole course.
The price is RM461
RM519 total
includes taxes & fees
26 Nov - 27 Nov
Rosen Shingle Creek
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Winter Park Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"“We had a wonderful stay with our family. The hotel was extremely clean, comfortable, and well-organized. The staff were very friendly and helpful, and their kindness toward our child made our stay even better. The location is perfect — close to everything and easy to reach the theme parks. Our room was spacious and the beds were very comfortable. We would definitely stay here again. Highly recommended!"
ipek 3-night trip
Posted 4 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Frequently asked questions

What are some accommodation options with pools in Winter Park?
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. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Offers 6 outdoor swimming pools, a children's pool and 3 restaurants. Ramada by Wyndham Suites Orlando Airport: Provides a snack bar/deli, an outdoor pool and daily. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Features 2 coffee shops/cafes, 3 outdoor swimming pools and complimentary wireless Internet access. Rosen Inn Lake Buena Vista: Hotel located near Disney Springs™. Offers 2 outdoor swimming pools, a children's 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 Walt Disney World® Resort 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.