Find Hotels with a Pool in Winter Park, FL

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

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Park Hotels with a Pool

Top Winter Park Hotels with a Pool

Outdoor pool
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

3.0 star property
Orlando
  • Outdoor pool
10.0 out of 10, Exceptional, (1)
$229 nightly
The price is $255
Nov 17 - Nov 18
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
Pool
Magic Studio

Magic Studio

Orlando
  • Hot tub
9.4 out of 10, Exceptional, (3)
$148 nightly
The price is $164
Nov 17 - Nov 18
Total with taxes and fees
Magic Studio
Outdoor pool
Charming Winter Park 3 Bedroom Villa with Pool

Charming Winter Park 3 Bedroom Villa with Pool

Goldenrod
  • Outdoor pool
9.4 out of 10, Exceptional, (11)
$321 nightly
The price is $355
Nov 17 - Nov 18
Total with taxes and fees
Charming Winter Park 3 Bedroom Villa with Pool
Outdoor pool
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
  • Outdoor pool
9.4 out of 10, Exceptional, (3)
Swimming options abound at this intimate 1-bedroom vacation rental featuring both a refreshing outdoor pool and exclusive private pool. Garden views complement the aquatic experience while a fully-equipped kitchenette provides convenient vacation comforts.
$148 nightly
The price is $164
Nov 19 - Nov 20
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
Outdoor pool, open 10:00 AM to 5:00 PM, pool umbrellas, sun 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, (1002)
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.
$354 nightly
The price is $398
Nov 23 - Nov 24
Total with taxes and fees
The Alfond Inn
Pool
Cozy RV with AC and fitness room in brilliant Winter Park

Cozy RV with AC and fitness room in brilliant Winter Park

Goldenrod
  • Hot tub
$120 nightly
The price is $132
Nov 18 - Nov 19
Total with taxes and fees
Cozy RV with AC and fitness room in brilliant Winter Park
A heated pool
Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
8.0 out of 10, Very Good, (11)
$362 nightly
The price is $400
Nov 17 - Nov 18
Total with taxes and fees
Winter Park Charmer - Heated Pool Home - Close to everything
Outdoor pool, open 8:00 AM to 9:00 PM, 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, (589)
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 center.
$76 nightly
The price is $85
Dec 7 - Dec 8
Total with taxes and fees
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, pool umbrellas, sun loungers
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

4.0 star property
International Drive District
  • Outdoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (1264)
Poolside relaxation awaits after thrilling theme park adventures, with sun loungers and umbrellas providing ideal comfort. The central location near Universal Orlando Resort, complimentary shuttle service, and daily breakfast buffet complete this perfect vacation hub.
$124 nightly
The price is $140
Nov 16 - Nov 17
Total with taxes and fees
Hyatt House Orlando International Drive
6 outdoor pools, free cabanas, pool umbrellas
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4.0 star property
Orlando
  • 6 outdoor pools
  • 2 poolside bars
  • Pool loungers
  • 8 hot tubs
9.4 out of 10, Exceptional, (3906)
$82 nightly
The price is $92
Nov 30 - Dec 1
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"👍"
CHAD 1-night trip
Posted 16 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Frequently asked questions

What are some accommodations 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 pools, and 2 restaurants. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Offers 6 outdoor 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 pools, and complimentary wireless internet access. Rosen Inn Lake Buena Vista: Hotel located near Disney Springs™. Offers 2 outdoor pools, a children's pool, and a snack bar/deli.
What is there to see and do in Winter Park?
Explore places like 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. Travelers 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 into account the local weather in Winter Park can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Park are August, September, July, and June, with each month seeing an average of 7 inches 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. To venture out into the surrounding area, hop aboard a train at Winter Park Station. Winter Park might not have very many public transit choices so consider renting a car to explore more.

Explore a world of travel with Expedia