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 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
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.
Bar (on property)
A modern hotel room with a dining area, a sofa, a chair, and a large window with curtains.
An aerial view of a resort with multiple swimming pools, palm trees, and lounge areas.

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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Orlando
$137 nightly
$154 total
Oct 25 - Oct 26
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.
An outdoor dining area with tables and chairs, string lights, and a building with arches and balconies.
A hotel with multiple floors, outdoor seating areas, and a well-lit courtyard.
A spacious lobby with a high ceiling, large windows, and a grand piano.

2. The Alfond Inn

The Alfond Inn
Winter Park
  • Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
$324 nightly
$365 total
Oct 5 - Oct 6
Total with taxes and fees
The Alfond Inn
A swimming pool area with multiple water slides and palm trees.
A spacious indoor atrium with high ceilings, palm trees, and modern seating areas.
A modern hotel room with a large window, a sofa, a TV, a desk, and a bed.
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 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 spacious lobby with a central seating area, a bar, and a well-lit ceiling with chandeliers.
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 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.
$106 nightly
$119 total
Oct 11 - Oct 12
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 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.
$219 nightly
$246 total
Nov 3 - Nov 4
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 Sheraton Orlando North hotel with a modern design, featuring a large palm tree, well-lit entrance, and a clear sky.
A spacious indoor dining area with a high ceiling and a glass structure. Tables are set with candles and tableware.
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 poolside setting with a glass of iced tea, a hat, a striped towel, a potted plant, and a pair of sandals.
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.

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.
A modern living room with a large flat-screen TV, blue sofas, a round coffee table, and a bookshelf.
An outdoor patio area with wicker furniture, a glass table, and a view of a building in the background.

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 hotel room with a sofa, a coffee table, a desk with a phone, a TV mounted on the wall, and a lamp.
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.

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
Oct 18 - Oct 19
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 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.
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

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"The room was extremely clean. The staff was extremely helpful . Thanks for a wonderful stay."
Melissa 1-night trip
Posted 1 hour ago
Westgate Lakes Resort & Spa Universal Studios Area
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Great hotel, with awesome amenities!!"
Robert 1-night trip
Posted 1 hour ago
Drury Plaza Hotel Orlando - Disney Springs Area
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

8/10 Good
"Basic room but comfortable and clean. Excellent value. Impressive staff."
NEIL 1-night trip
Posted 5 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
"The location was great for your needs and the staff was friendly and accommodating. We had a great time and will definitely be back next time we are in the area."
Daniel 1-night trip
Posted 5 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Awesome place"
Jamie 3-night trip
Posted 6 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Rosen Inn International

Rosen Inn International

8/10 Good
"Close to Universal and restaurant on site."
Bob 1-night trip
Posted 11 hours ago
Rosen Inn International

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 $80 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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