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

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Our top choices for Winter Park hotels with a pool

A cozy living room with a leather sofa, a wooden coffee table, and a leather armchair. There are potted plants and a staircase in the background.

1. Park Plaza Hotel

Park Plaza Hotel
3.0 star property
Park Avenue District
8.6 out of 10, Excellent, (1,000 reviews)
"Good bed, good shower, and an extremely helpful, friendly and welcoming front desk staff."
United States
James
The price is AED 663
AED 746 total
includes taxes & fees
13 Dec - 14 Dec
Park Plaza Hotel
A modern interior with a reception desk, a food display, and a beverage cooler.

2. Hilton Garden Inn Winter Park

Hilton Garden Inn Winter Park
3.0 star property
Winter Park
9.2 out of 10, Wonderful, (758 reviews)
"Awesome stay, great staff and location"
United States
Crystile
The price is AED 731
AED 832 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Winter Park
An outdoor seating area with a fire feature, cushioned benches, and chairs.

3. SpringHill Suites by Marriott Winter Park

SpringHill Suites by Marriott Winter Park
2.5 star property
Winter Park
9.2 out of 10, Wonderful, (428 reviews)
"GREAT PLACE TO STAY."
United States
WILFREDO
The price is AED 731
AED 832 total
includes taxes & fees
29 Nov - 30 Nov
SpringHill Suites by Marriott Winter Park
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.
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Choose what matters most at hotels with a pool in Winter Park

Breakfast included
4 stars

Top Winter Park Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Room was very clean, property’s a bit confusing since it’s so big, it’s very easy to get lost in there lol."
Jason 2-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Frequently asked questions

What are some accommodations 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 pools, a children's pool, and 3 restaurants. Marriott's Grande Vista: Aparthotel located near Orlando Vineland Premium Outlets. Provides 4 outdoor 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 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 like 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. 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.