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 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
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.
A turtle in a landscaped area with palm trees and a water feature.
A modern hotel room with a dining area, a sofa, a chair, and a large window with curtains.

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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Orlando
$137 nightly
$154 total
Oct 29 - Oct 30
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 lobby with a high ceiling, large windows, and a grand piano.
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
$363 total
Oct 12 - Oct 13
Total with taxes and fees
The Alfond Inn
A swimming pool area with multiple water slides and palm trees.
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.
A child sitting on a blue inflatable pool in a hotel room with a large window, a red armchair, and a suitcase.

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 4 - Nov 5
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 DoubleTree by Hilton hotel with a modern design, featuring a large glass facade and a prominent sign at the top.
A spacious lobby with a central seating area, a bar, and a well-lit ceiling with chandeliers.
A spacious lobby with multiple seating areas, including sofas and chairs, a coffee table, and a bar area with a television.

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.
$110 nightly
$123 total
Oct 15 - Oct 16
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 resort with multiple swimming pools surrounded by lush greenery and a large hotel building.
A modern lobby with a reception desk, seating area, and a bar.
A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.

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.
$219 nightly
$246 total
Nov 9 - Nov 10
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 spacious lobby with a high glass ceiling, a bar area, and seating arrangements.
A spacious indoor dining area with a high ceiling and a glass structure. Tables are set with candles and tableware.
A Sheraton Orlando North hotel with a modern design, featuring a large palm tree, well-lit entrance, and a clear sky.

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 spacious living room with a sectional sofa, patterned armchairs, a coffee table, and a dining area with yellow chairs.
A modern hotel room with a flat-screen TV, a desk, a sofa, and a large window with a city view.
A modern building with a glass facade and a prominent entrance.

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.
A multi-story hotel with a modern design, featuring balconies and a covered entrance.
Restaurant
A modern living room with a large flat-screen TV, blue sofas, a round coffee table, and a bookshelf.

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 hotel lobby with a long corridor, large textured pillars, seating areas, and potted plants.
A hotel room with a sofa, a coffee table, a desk with a phone, a TV mounted on the wall, and a lamp.

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.
$112 nightly
$127 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 hotel room with a bathroom, a bed, and a balcony with curtains.
A modern bathroom with a large mirror, a sink, a bathtub, and a shower.
A modern hotel lobby with a reception desk, a seating area with a sofa, a bookshelf, and a large chandelier.

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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"I love it especially the staff member , “Cam”."
Jakiya 2-night trip
Posted 2 hours ago
Universal's Cabana Bay Beach Resort
Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"Truly accommodating celebrated my daughter’s 5th birthday front desk was so sweet to send an arrangement for her had plenty of kids activities staff was amazing sweet and the rooms were to die for love how our sweet made us feel like home."
Massiel Carina Carino 3-night trip
Posted 5 hours ago
Marriott's Grande Vista
Buena Vista Suites Orlando

Buena Vista Suites Orlando

10/10 Excellent
"Perfect spot if you’re visiting the parks or attending an event at the conference center right next door. The suites are roomy, super comfortable, and come with everything you need. You definitely get a lot of value for your money here!"
Diego 2-night trip
Posted 6 hours ago
Buena Vista Suites Orlando
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent
"It was great"
Maria 3-night trip
Posted 8 hours ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village
Courtyard by Marriott across Universal Orlando

Courtyard by Marriott across Universal Orlando

8/10 Good
"It’s under construction but the improvements are better now. Been here about 7 times. Staff used to be better. Now some staff is rude. Never had any issues before. Also parking should be free if everyone is polite and everything is clean people would be willing to pay a little more instead of parking. Maybe add valet to get better service."
Troy 4-night trip
Posted 10 hours ago
Courtyard by Marriott across Universal Orlando

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 $85 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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