Check prices for these dates
Our top choices for Winter Park hotels with a pool
1. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando4.0 star property
Orlando
9.2 out of 10, Wonderful, (7,319 reviews)
9.2/10
Wonderful
(7,319 reviews)
$111 nightly
The price is $125
$125 total
Dec 13 - Dec 14
Total with taxes and fees
2. The Alfond Inn
The Alfond Inn4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1,002 reviews)
9.6/10
Exceptional
(1,002 reviews)
- Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
$313 nightly
The price is $352
$352 total
Dec 14 - Dec 15
Total with taxes and fees
3. Universal's Cabana Bay Beach Resort
Universal's Cabana Bay Beach Resort3.5 star property
Florida Center
9.0 out of 10, Wonderful, (7,865 reviews)
9.0/10
Wonderful
(7,865 reviews)
- Dive into double the fun with 2 outdoor pools, hot tubs, and a lazy river paradise.
$150 nightly
The price is $169
$169 total
Dec 14 - Dec 15
Total with taxes and fees
4. DoubleTree by Hilton Hotel Orlando Downtown
DoubleTree by Hilton Hotel Orlando Downtown4.0 star property
Ivanhoe Village
8.2 out of 10, Very good, (3,483 reviews)
8.2/10
Very good
(3,483 reviews)
- Take a splash in the refreshing rooftop pool with views of downtown Orlando's skyline.
$91 nightly
The price is $102
$102 total
Nov 29 - Nov 30
Total with taxes and fees
5. The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando4.0 star property
Winter Garden
8.2 out of 10, Very good, (10,951 reviews)
8.2/10
Very good
(10,951 reviews)
- Splash into paradise at this resort with 6 outdoor pools, a lazy river, and a complimentary water park for endless aquatic fun.
$222 nightly
The price is $250
$250 total
Dec 7 - Dec 8
Total with taxes and fees
6. Sheraton Orlando North Hotel
Sheraton Orlando North Hotel3.5 star property
Maitland
8.4 out of 10, Very good, (1,480 reviews)
8.4/10
Very good
(1,480 reviews)
- Soak in sunshine at the sparkling outdoor pool, complete with comfortable loungers and a bubbling hot tub to refresh your senses.
$94 nightly
The price is $106
$106 total
Nov 29 - Nov 30
Total with taxes and fees
7. Crowne Plaza Orlando - Downtown by IHG
Crowne Plaza Orlando - Downtown by IHG3.5 star property
Lake Dot
8.8 out of 10, Excellent, (942 reviews)
8.8/10
Excellent
(942 reviews)
$122 nightly
The price is $137
$137 total
Nov 26 - Nov 27
Total with taxes and fees
8. Courtyard by Marriott Orlando Downtown
Courtyard by Marriott Orlando Downtown3.0 star property
Ivanhoe Village
9.4 out of 10, Exceptional, (1,135 reviews)
9.4/10
Exceptional
(1,135 reviews)
- Float in sunshine at downtown Orlando's chic hotel pool, surrounded by plush loungers and umbrellas.
$118 nightly
The price is $133
$133 total
Nov 22 - Nov 23
Total with taxes and fees
9. Hilton Orlando/Altamonte Springs
Hilton Orlando/Altamonte Springs4.0 star property
Altamonte Springs
9.0 out of 10, Wonderful, (1,603 reviews)
9.0/10
Wonderful
(1,603 reviews)
- Sink into pure bliss at this outdoor pool with loungers for a refreshing Florida getaway.
$125 nightly
The price is $142
$142 total
Dec 13 - Dec 14
Total with taxes and fees
10. Embassy Suites by Hilton Orlando Downtown
Embassy Suites by Hilton Orlando Downtown3.5 star property
Downtown Orlando
9.0 out of 10, Wonderful, (1,002 reviews)
9.0/10
Wonderful
(1,002 reviews)
$163 nightly
The price is $184
$184 total
Nov 22 - Nov 23
Total with taxes and fees
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.
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.
Top Winter Park Hotel Reviews
The Alfond Inn
The Alfond InnWinter Park
10/10 Excellent
A beautiful property managed with care and consideration for the aesthetics and for the pampering of its guests. For as many times as I will visit Winter Park, I will stay here again and again.
A beautiful property managed with care and consideration for the aesthetics and for the pampering of its guests. For as many times as I will visit Winter Park, I will stay here again and again.
Gail
Comfort Suites Downtown
Comfort Suites DowntownIvanhoe Village
10/10 Excellent
check in was fantastic, The Lady who checked me in was very very friendly and helpfull, breakfast is disappointing to say the least
check in was fantastic, The Lady who checked me in was very very friendly and helpfull, breakfast is disappointing to say the least
Glenn
Rosen Shingle Creek
Rosen Shingle CreekOrlando
10/10 Excellent
It was stunning and pristine. Very well managed, maintained and extremely clean. Awesome amenities and restaurants. Staff was friendly and helpful. My wife and I loved it and we’re so glad we chose to stay here for our 25th anniversary.
It was stunning and pristine. Very well managed, maintained and extremely clean. Awesome amenities and restaurants. Staff was friendly and helpful. My wife and I loved it and we’re so glad we chose to stay here for our 25th anniversary.
Narciso
La Quinta Inn & Suites by Wyndham Orlando UCF
La Quinta Inn & Suites by Wyndham Orlando UCFOrlando
10/10 Excellent
Everything clean and quiet. Staff is friendly. Rooms are clean, beds are comfy. It has what you need. They served free breakfast with my reservation but I didn’t try it. They had a station with coffee, tea and water which is the one thing I saw needed improvement (more frequent checks to make sure they’re not out of it)
Everything clean and quiet. Staff is friendly. Rooms are clean, beds are comfy. It has what you need. They served free breakfast with my reservation but I didn’t try it. They had a station with coffee, tea and water which is the one thing I saw needed improvement (more frequent checks to make sure they’re not out of it)
Bianca
Hyatt House Orlando Airport
Hyatt House Orlando AirportAirport North
10/10 Excellent
New hotel, clean, no carpet!
New hotel, clean, no carpet!
Aleksandra
Hampton Inn & Suites Orlando Airport @ Gateway Village
Hampton Inn & Suites Orlando Airport @ Gateway VillageAirport North
10/10 Excellent
Great location near airport and services
Great location near airport and services
Christine
Hyatt House Orlando International Drive
Hyatt House Orlando International DriveInternational Drive District
10/10 Excellent
We had a great stay at this hotel. The room was spotless, the staff was incredibly friendly, and it felt safe with 24/7 security patrolling the grounds. The air conditioning kept the room perfectly cool, and having a full kitchen was a huge plus. Highly recommend.
We had a great stay at this hotel. The room was spotless, the staff was incredibly friendly, and it felt safe with 24/7 security patrolling the grounds. The air conditioning kept the room perfectly cool, and having a full kitchen was a huge plus. Highly recommend.
jordan
Staybridge Suites Orlando Universal Blvd by IHG
Staybridge Suites Orlando Universal Blvd by IHGOrlando
10/10 Excellent
Impeccably clean hotel with great accommodations and a spacious room — we truly got to rest. Everything was perfect from start to finish, and the service was exceptional: the staff was attentive and helpful at all times. An excellent experience — I highly recommend it, and we will definitely be back!
Impeccably clean hotel with great accommodations and a spacious room — we truly got to rest. Everything was perfect from start to finish, and the service was exceptional: the staff was attentive and helpful at all times. An excellent experience — I highly recommend it, and we will definitely be back!
Juliana
Wyndham Garden Orlando Airport
Wyndham Garden Orlando AirportBelle Isle
10/10 Excellent
Super impressed with the entire property and was able to grab dinner at 8:30 before the kitchen closed! For an airport hotel this one is AMAZING! Clean, friendly, booked a 5am shuttle for the next morning at check-in. Staff was professional and very kind. Definitely will be staying here again the next time we’re in Orlando.
Super impressed with the entire property and was able to grab dinner at 8:30 before the kitchen closed! For an airport hotel this one is AMAZING! Clean, friendly, booked a 5am shuttle for the next morning at check-in. Staff was professional and very kind. Definitely will be staying here again the next time we’re in Orlando.
Francine
Fairfield Inn By Marriott Orlando Airport
Fairfield Inn By Marriott Orlando AirportAirport North
10/10 Excellent
Great location and two miles to Orlando airport
Great location and two miles to Orlando airport
Elizabeth
Wingate by Wyndham - Orlando International Airport
Wingate by Wyndham - Orlando International AirportAirport North
10/10 Excellent
Very smooth check in, safe and quiet hotel. Very clean.
Very smooth check in, safe and quiet hotel. Very clean.
Mary
Drury Plaza Hotel Orlando - Disney Springs Area
Drury Plaza Hotel Orlando - Disney Springs AreaLake Buena Vista
10/10 Excellent
Great place to stay
Great place to stay
Amy Dawn
Hyatt Place Lake Mary/Orlando North
Hyatt Place Lake Mary/Orlando NorthLake Mary
10/10 Excellent
Nice place. Absolutely loved the gym.
Nice place. Absolutely loved the gym.
Ian
Holiday Inn Express Orlando International Airport by IHG
Holiday Inn Express Orlando International Airport by IHGOrlando
10/10 Excellent
Chose to stay here when my flight was cancelled because it was close to MCO and had a shuttle. Large, comfortable, clean room, nice toiletries and a good breakfast. I would definitely stay here again.
Chose to stay here when my flight was cancelled because it was close to MCO and had a shuttle. Large, comfortable, clean room, nice toiletries and a good breakfast. I would definitely stay here again.
Patricia
Hampton Inn Orlando-International Airport
Hampton Inn Orlando-International AirportAirport North
10/10 Excellent
Staff was friendly, clean and convenient location for dining and shopping
Staff was friendly, clean and convenient location for dining and shopping
Rebeca
Embassy Suites by Hilton Orlando Lake Buena Vista South
Embassy Suites by Hilton Orlando Lake Buena Vista SouthKissimmee
10/10 Excellent
Check in and check process stemless, breakfast was perfect!
Check in and check process stemless, breakfast was perfect!
Chris
Staybridge Suites Orlando Airport South by IHG
Staybridge Suites Orlando Airport South by IHGAirport North
10/10 Excellent
It is way more better than what I expected, we got plane delayed so we decided to go here, but it is great suit room for family with one big kids and one small kid.
It is way more better than what I expected, we got plane delayed so we decided to go here, but it is great suit room for family with one big kids and one small kid.
Xiaofeng
Cambria Hotel Orlando Airport
Cambria Hotel Orlando AirportOrlando
10/10 Excellent
Very nice stay! Highly recommend, free parking, the price was great and the hotel is nicer than Aloft @ Lake Bueno Vista that changes $26.00 a night for parking and the room smelled like mildew and funky gym socks! Please give Cambria your money!!
Very nice stay! Highly recommend, free parking, the price was great and the hotel is nicer than Aloft @ Lake Bueno Vista that changes $26.00 a night for parking and the room smelled like mildew and funky gym socks! Please give Cambria your money!!
Vicki
Universal's Endless Summer Resort - Dockside Inn and Suites
Universal's Endless Summer Resort - Dockside Inn and SuitesFlorida Center
10/10 Excellent
Close to Universal, walkable but also had plenty of transportation options. Property was clean and stay was friendly.
Close to Universal, walkable but also had plenty of transportation options. Property was clean and stay was friendly.
cynthia
Find out more about Winter Park
Discover top Winter Park attractions
Winter Park offers a delightful array of activities for travelers seeking adventure and relaxation alike. Begin your day with a scenic hike through the breathtaking landscapes of the nearby mountains, where you can immerse yourself in the pristine beauty of nature. Afterward, take a leisurely stroll through the charming downtown area, featuring unique boutiques and artisanal shops that showcase the local craftsmanship. For those looking for a bit of excitement, the area boasts thrilling outdoor sports, including mountain biking and snowboarding in the winter months, perfect for adrenaline junkies. Don’t forget to unwind at one of the inviting local spas, where you can indulge in rejuvenating treatments to soothe your muscles after a day of exploration. Finally, savor the region’s culinary delights at farm-to-table eateries, where you can enjoy fresh, seasonal dishes crafted from local ingredients. With a variety of accommodations that cater to quality seekers, you can rest assured you’ll find a perfect home base for your Winter Park adventure.
Find the best pool hotels in Winter Park
For travelers seeking a refreshing getaway in Winter Park, these hotels offer exceptional pool amenities that promise a relaxing experience.
- Why it's great: The Alfond Inn is an outstanding destination for travelers who prioritize poolside relaxation, with a perfect traveler review rating of 10 out of 10. This 4-star hotel features a stunning outdoor pool equipped with poolside cabanas, sun loungers, and an accessible design for everyone to enjoy. Guests can unwind at the poolside bar, savoring delicious refreshments as they bask in the sun.
- Other amenities: In addition to its exceptional pool offerings, The Alfond Inn provides a range of luxurious amenities designed for ultimate comfort. Guests can indulge in spa services including body treatments and massages, or enjoy the serene garden surroundings. The hotel also features designer toiletries, premium bedding, and daily housekeeping for a pleasant stay. For those looking to dine on-site, breakfast options are available, and the hotel offers concierge services to assist with local explorations.
- Nearby attractions: Rollins Museum of Art - less than 1 mile, Virginia S. Nelson Rose Garden - less than 1 mile
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 $102 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.