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

Find Hotels with a Pool in Winter Park, FL

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Check availability on Winter Park Hotels with a Pool

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Winter Park hotels with a pool

A swimming pool with a waterfall feature, lounge chairs, and a gazebo.
An aerial view of a resort with multiple swimming pools, palm trees, and lounge areas.
Bar (on property)
A turtle in a landscaped area with palm trees and a water feature.

1. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Orlando
$137 nightly
$154 total
Oct 27 - Oct 28
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
A multi-story hotel with balconies, a swimming pool, and a landscaped courtyard.
A spacious hall with a grand piano, large windows, and a central floral arrangement.
A hotel with multiple floors, outdoor seating areas, and a well-lit courtyard.
An outdoor dining area with tables and chairs, string lights, and a building with arches and balconies.

2. The Alfond Inn

The Alfond Inn
Winter Park
  • Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
$323 nightly
$364 total
Nov 1 - Nov 2
Total with taxes and fees
The Alfond Inn
A swimming pool area with multiple water slides and palm trees.
A child sitting on a blue inflatable pool in a hotel room with a large window, a red armchair, and a suitcase.
A modern hotel room with a large window, a sofa, a TV, a desk, and a bed.
A spacious indoor atrium with high ceilings, palm trees, and modern seating areas.

3. Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort
Florida Center
  • Dive into double the fun with 2 outdoor pools, hot tubs, and a lazy river paradise.
$150 nightly
$169 total
Nov 3 - Nov 4
Total with taxes and fees
Universal's Cabana Bay Beach Resort
A hotel pool area with sun loungers, a swimming pool, and palm trees.
A hotel room with a large bed, a flat-screen TV, a wooden dresser, and a city view through large windows.
A spacious lobby with multiple seating areas, including sofas and chairs, a coffee table, and a bar area with a television.
A spacious lobby with a central seating area, a bar, and a well-lit ceiling with chandeliers.

4. DoubleTree by Hilton Hotel Orlando Downtown

DoubleTree by Hilton Hotel Orlando Downtown
Ivanhoe Village
  • Take a splash in the refreshing rooftop pool with views of downtown Orlando's skyline.
$106 nightly
$119 total
Oct 13 - Oct 14
Total with taxes and fees
DoubleTree by Hilton Hotel Orlando Downtown
A resort with a large pool, water slides, palm trees, and beach umbrellas.
A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.
A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.
A modern lobby with a reception desk, seating area, and a bar.

5. The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
  • Splash into paradise at this resort with 6 outdoor pools, a lazy river, and a complimentary water park for endless aquatic fun.
$224 nightly
$252 total
Nov 5 - Nov 6
Total with taxes and fees
The Grove Resort & Water Park Orlando
A hotel pool with a waterfall feature, lounge chairs, and a building with multiple balconies.
A bar area with a wooden bar counter, two bar stools, and a well-stocked shelf of bottles.
A Sheraton Orlando North hotel with a modern design, featuring a large palm tree, well-lit entrance, and a clear sky.
A spacious lobby with a high glass ceiling, a bar area, and seating arrangements.

6. Sheraton Orlando North Hotel

Sheraton Orlando North Hotel
Maitland
  • Soak in sunshine at the sparkling outdoor pool, complete with comfortable loungers and a bubbling hot tub to refresh your senses.
$107 nightly
$120 total
Nov 1 - Nov 2
Total with taxes and fees
Sheraton Orlando North Hotel
Pool
A modern building with a glass facade and a prominent entrance.
A modern hotel room with a flat-screen TV, a desk, a sofa, and a large window with a city view.
A poolside setting with a glass of iced tea, a hat, a striped towel, a potted plant, and a pair of sandals.

7. Crowne Plaza Orlando - Downtown by IHG

Crowne Plaza Orlando - Downtown by IHG
Lake Dot
$131 nightly
$147 total
Oct 15 - Oct 16
Total with taxes and fees
Crowne Plaza Orlando - Downtown by IHG
A swimming pool with wooden deck seating, palm trees, and a modern building in the background.
An outdoor patio area with wicker furniture, a glass table, and a view of a building in the background.
A modern living room with a large flat-screen TV, blue sofas, a round coffee table, and a bookshelf.
A multi-story hotel with a modern design, featuring balconies and a covered entrance.

8. Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown
Ivanhoe Village
  • Float in sunshine at downtown Orlando's chic hotel pool, surrounded by plush loungers and umbrellas.
$118 nightly
$133 total
Oct 15 - Oct 16
Total with taxes and fees
Courtyard by Marriott Orlando Downtown
A swimming pool with lounge chairs, a brick building, and palm trees.
A bar area with a curved counter, multiple bar stools, and hanging pendant lights.
A modern lobby with a reception desk, seating area, and decorative columns.
A hotel lobby with a long corridor, large textured pillars, seating areas, and potted plants.

9. Hilton Orlando/Altamonte Springs

Hilton Orlando/Altamonte Springs
Altamonte Springs
  • Sink into pure bliss at this outdoor pool with loungers for a refreshing Florida getaway.
$110 nightly
$125 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Orlando/Altamonte Springs
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and a church spire.
A modern hotel lobby with a reception desk, a seating area with a sofa, a bookshelf, and a large chandelier.
A hotel room with a bathroom, a bed, and a balcony with curtains.
A modern bar area with high ceilings, multiple levels, and a variety of seating options including bar stools and tables.

10. Embassy Suites by Hilton Orlando Downtown

Embassy Suites by Hilton Orlando Downtown
Downtown Orlando
$163 nightly
$184 total
Oct 12 - Oct 13
Total with taxes and fees
Embassy Suites by Hilton Orlando Downtown
View all properties

Choose what matters most at hotels with a pool in Winter Park

Breakfast included
Hot tub
Water park
Spa
4 stars

Top Winter Park Hotel Reviews

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"Convenient location to stay, to take flights in or out ."
Karren 1-night trip
Posted less than an hour ago
Hyatt Regency Orlando International Airport
Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"Room was well stocked and comfortable. Very clean"
Leisa 3-night trip
Posted 1 hour ago
Marriott's Grande Vista
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Clean and spacious room. Swimming pools were great!!"
Yorlenny Maria 5-night trip
Posted 1 hour ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Is a good place to stay"
Jaime 5-night trip
Posted 2 hours ago
Universal's Cabana Bay Beach Resort
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8/10 Good
"Very nice set up. There was a terrible chemical smell that never went away. We notified the maintenance guy and he smelled it too but nothing was ever done about it. Gave everyone headaches. We stayed for four days.....it never went away."
Kristie 4-night trip
Posted 3 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Would book here again, friendly staff."
Glenda 2-night trip
Posted 9 hours ago
Rosen Inn Lake Buena Vista
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"Is clean the hotel and the staff is friendly and helps travelers when needed any questions."
Jorgito 3-night trip
Posted 10 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent
"Every employee we spoke to was wonderful. We enjoyed the daily breakfast and the variety of choices. There was always ice water in the lobby. The pool was never crowded at most we shared it with 2 other families. The hotel is close to Disney Springs and the outlets as well as many restaurants and stores. The only issues we ran into were the food hall was temporarily closed while we were there and the bubbles in the hot tub didn’t work. I would definitely stay here again it was a great value for the price."
Carrie 3-night trip
Posted 13 hours ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Beautiful resort"
Heather 3-night trip
Posted 15 hours ago
Westgate Lakes Resort & Spa Universal Studios Area

Frequently asked questions

How much does a hotel with outdoor pool in Winter Park cost?
Enjoy staying in a hotel in Winter Park with an outdoor pool. You can find a great deal from $95 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Which Winter Park hotels offer poolside service for food and drinks?
The Alfond Inn is a fantastic option for travellers seeking a hotel in Winter Park with poolside service for food and drinks. This elegant 4-star hotel boasts an outdoor pool where guests can soak up the sun while enjoying delicious refreshments from the poolside bar. With a remarkable traveller rating of 9.6, guests frequently rave about the top service and friendly staff, making it an inviting retreat for travellers.In addition to the inviting pool, The Alfond Inn offers a range of luxurious amenities, including a spa with various treatments that can rejuvenate your body after a day of exploration. Its comfortable and beautifully designed rooms ensure a relaxing stay, while the fabulous dining options keep visitors coming back for more.
Is it cheaper to book flights and a Winter Park hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Winter Park for you.

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