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

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Check availability on Winter Park Hotels with Pool

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for Winter Park hotels with a pool

1. The Alfond Inn

The Alfond Inn
Winter Park
  • Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
5.749.178 ₫
7.260.228 ₫ total
includes taxes & fees
3 Sept - 4 Sept
The Alfond Inn

2. 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.
3.191.947 ₫
3.590.940 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Courtyard by Marriott Orlando Downtown

3. 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.
2.943.206 ₫
3.311.107 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Comfort Suites Downtown

4. 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.
2.128.373 ₫
2.394.419 ₫ total
includes taxes & fees
6 Sept - 7 Sept
La Quinta Inn & Suites by Wyndham Orlando UCF

5. 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.
1.995.349 ₫
2.244.769 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Wingate by Wyndham - Orlando International Airport

6. DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando
Florida Center
  • Splash into Florida sunshine at the entrance to Universal Orlando with a poolside cocktail and refreshing hot tub.
1.847.981 ₫
2.078.980 ₫ total
includes taxes & fees
7 Sept - 8 Sept
DoubleTree by Hilton at the Entrance to Universal Orlando

7. Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village
Airport North
  • Vibrant pool oasis near Orlando Airport beckons travellers to dive in after a day exploring nearby attractions.
2.331.299 ₫
2.622.711 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn & Suites Orlando Airport @ Gateway Village
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

10/10 Excellent
"Friendly staff, safe spacious shuttle to Disney parks. Evening cocktails and appetizers are amazing."
Kevin 5-night trip
Posted 1 hour ago
Drury Plaza Hotel Orlando - Disney Springs Area
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Amazing stay, good cookies, love the late night options like ice cream and shuttle to and from universal"
Auwais 2-night trip
Posted 2 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Rosen Inn International

Rosen Inn International

10/10 Excellent
"Clean & affordability. Accommodation for my handicap child no issues. Nice front desk."
Rachel 1-night trip
Posted 2 hours ago
Rosen Inn International
Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite

10/10 Excellent
"The resort is excellent for all types of travellers. We were travelling with our 12 year old daughter on her first international trip. The room was comfortable, spacious and allowed for her to have her own space in the living room area when she needed to relax. The arcade, pool, restaurants, Starbucks, trails and gym were incredible. The hotel’s location is perfectly central to the theme parks, restaurants and shopping in Orlando."
Genevieve 3-night trip
Posted 4 hours ago
Caribe Royale Orlando, WorldHotels Elite
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

8/10 Good
"Cabana Bay was nice, room was very clean and staff was very friendly. Only negative things I have are……water leak in the hallway of our room, had a garbage can catching the water and was never fixed the whole time we were there, hallways had a lot of scratches and holes in the walls, def needs painted. Also stains on the hallway carpet floors. We had wash cloths the first day, were never given to us again, even after asking housekeeping. Don’t regret staying there, just think I’d look elsewhere next time."
Kathy 4-night trip
Posted 4 hours ago
Universal's Cabana Bay Beach Resort
Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport

8/10 Good
"The hotel was good and served us well for the purpose it was intended for. The staff were friendly and informative, even got them to suggest activities for the 2 days we were there and the shuffle service was a plus."
sabrina 2-night trip
Posted 1 day ago
Ramada by Wyndham Suites Orlando Airport

Frequently asked questions

What is there to see and do in Winter Park?
Explore places such as Universal Studios Florida, Universal Orlando Resort and Universal's Volcano Bay 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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