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

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Winter Park hotels with a pool

Exterior

The Alfond Inn

The Alfond Inn
4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1,010 reviews)
  • cleanliness
    Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
$326 nightly
The price is $367
Jul 30 - Jul 31
Total with taxes and fees
The Alfond Inn
Outdoor pool

The Canopy on Periwinkle- A Home Away From Home

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
10.0 out of 10, Exceptional, (3 reviews)
$419 nightly
The price is $466
Aug 2 - Aug 3
Total with taxes and fees
The Canopy on Periwinkle- A Home Away From Home
Outdoor pool

Quiet and safe neighborhood come to this great place with lots of room for relax

Quiet and safe neighborhood come to this great place with lots of room for relax
Orlando
9.6 out of 10, Exceptional, (4 reviews)
$263 nightly
The price is $292
Jul 29 - Jul 30
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
Outdoor pool

1-bedroom vacation room just 12 minutes from University of Central Florida

1-bedroom vacation room just 12 minutes from University of Central Florida
Orlando
9.6 out of 10, Exceptional, (4 reviews)
  • cleanliness
    Relax poolside at a cozy retreat with both private and outdoor pools, just 12 minutes from University of Central Florida.
$153 nightly
The price is $169
Aug 4 - Aug 5
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
A heated pool

Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park Charmer - Heated Pool Home - Close to everything
Winter Park
8.2 out of 10, Very Good, (19 reviews)
$368 nightly
The price is $407
Aug 15 - Aug 16
Total with taxes and fees
Winter Park Charmer - Heated Pool Home - Close to everything
Outdoor pool, open 6:00 AM to 11:00 PM, pool umbrellas, sun loungers

Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown
3.0 star property
Ivanhoe Village
9.4 out of 10, Exceptional, (1,042 reviews)
  • cleanliness
    Float in sunshine at downtown Orlando's chic hotel pool, surrounded by plush loungers and umbrellas.
$122 nightly
The price is $138
Jul 31 - Aug 1
Total with taxes and fees
Courtyard by Marriott Orlando Downtown
Seasonal outdoor pool

Comfort Suites Downtown

Comfort Suites Downtown
2.5 star property
Ivanhoe Village
8.8 out of 10, Excellent, (1,022 reviews)
  • cleanliness
    Make a splash in downtown Orlando with this hotel's seasonal outdoor pool and relaxing hot tub for post-exploration recovery.
$105 nightly
The price is $119
Aug 23 - Aug 24
Total with taxes and fees
Comfort Suites Downtown
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers

Hilton Orlando/Altamonte Springs

Hilton Orlando/Altamonte Springs
4.0 star property
Altamonte Springs
9.0 out of 10, Wonderful, (1,532 reviews)
  • cleanliness
    Sink into pure bliss at this outdoor pool with loungers for a refreshing Florida getaway.
$113 nightly
The price is $128
Aug 2 - Aug 3
Total with taxes and fees
Hilton Orlando/Altamonte Springs
Outdoor pool

La Quinta Inn & Suites by Wyndham Orlando UCF

La Quinta Inn & Suites by Wyndham Orlando UCF
3.0 star property
Orlando
8.8 out of 10, Excellent, (2,688 reviews)
  • cleanliness
    Sun-soaked outdoor pool offers refreshing escapes and hot tub relaxation near the University of Central Florida campus.
$89 nightly
The price is $100
Aug 2 - Aug 3
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando UCF
Outdoor pool

Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
Airport North
9.6 out of 10, Exceptional, (2,953 reviews)
  • cleanliness
    Refreshing outdoor pool sanctuary awaits near Florida Mall, with a firepit and poolside lounging for a sunny getaway experience.
$114 nightly
The price is $128
Aug 11 - Aug 12
Total with taxes and fees
Hyatt House Orlando Airport
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.
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Choose what matters most at hotels with a pool in Winter Park

Breakfast included
Hot tub

Top Winter Park Hotel Reviews

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"Hotel was clean and convenient. Located right inside the airport with quick and easy access to all 3 terminals."
Carl 1-night trip
Posted 1 hour ago
Hyatt Regency Orlando International Airport

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 $100 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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