Find Hotels with a Pool in Winter Park, FL

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Our top choices for Winter Park hotels with a pool

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
9.4 out of 10, Exceptional, (3 reviews)
  • cleanliness
    Relax poolside at a cozy retreat with both private and outdoor pools, just 12 minutes from University of Central Florida.
$159 nightly
The price is $176
Apr 13 - Apr 14
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
8.0 out of 10, Very Good, (14 reviews)
$385 nightly
The price is $428
Mar 17 - Mar 18
Total with taxes and fees
Winter Park Charmer - Heated Pool Home - Close to everything
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
10.0 out of 10, Exceptional, (2 reviews)
$250 nightly
The price is $278
Apr 13 - Apr 14
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
2 outdoor pools, open 10:00 AM to 5:00 PM, cabanas (surcharge)

The Alfond Inn

The Alfond Inn
4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1,005 reviews)
  • cleanliness
    Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
$324 nightly
The price is $365
Apr 12 - Apr 13
Total with taxes and fees
The Alfond Inn
Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
International Drive District
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.
$93 nightly
The price is $104
Apr 5 - Apr 6
Total with taxes and fees
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Poolside Family Suite - Exterior Entry (Includes Early Park Admission*) | View from room

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort
3.5 star property
Florida Center
9.0 out of 10, Wonderful, (6,408 reviews)
  • cleanliness
    Dive into double the fun with 2 outdoor pools, hot tubs, and a lazy river paradise.
$133 nightly
The price is $150
Apr 12 - Apr 13
Total with taxes and fees
Universal's Cabana Bay Beach Resort
Outdoor pool, pool umbrellas, sun loungers

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1,604 reviews)
  • cleanliness
    Sun-kissed relaxation awaits at this poolside oasis with loungers and shade umbrellas.
$118 nightly
The price is $133
Mar 22 - Mar 23
Total with taxes and fees
Hyatt House Orlando International Drive
Outdoor pool, pool umbrellas, sun loungers

La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport
3.0 star property
Airport North
7.4 out of 10, Good, (1,495 reviews)
  • cleanliness
    Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.
$95 nightly
The price is $107
Mar 16 - Mar 17
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando Airport
Outdoor pool, open 6:00 AM to midnight, pool umbrellas, sun loungers

Rosen Centre Hotel

Rosen Centre Hotel
4.0 star property
International Drive District
9.0 out of 10, Wonderful, (4,361 reviews)
  • cleanliness
    Dive into poolside bliss at this luxury resort with 2 hot tubs and full-service spa to rejuvenate your senses.
$95 nightly
The price is $107
Apr 6 - Apr 7
Total with taxes and fees
Rosen Centre Hotel
Outdoor pool

Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village
3.0 star property
Airport North
9.4 out of 10, Exceptional, (2,549 reviews)
  • cleanliness
    Vibrant pool oasis near Orlando Airport beckons travelers to dive in after a day exploring nearby attractions.
$106 nightly
The price is $119
Mar 30 - Mar 31
Total with taxes and fees
Hampton Inn & Suites Orlando Airport @ Gateway Village
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

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Top Winter Park Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"We do really enjoying our stay. My son love the lazy river "
baldomero 4-night trip
Posted 1 hour ago
Universal's Cabana Bay Beach Resort

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 $104 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.
How can I save on a Winter Park hotel with a pool with Expedia?
Before booking your Winter Park hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
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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