Find Hotels with a Pool in Winter Park, FL

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Our top choices for Winter Park hotels with a 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)
$264 nightly
The price is $293
May 4 - May 5
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax

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.
$150 nightly
The price is $166
May 13 - May 14
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida

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.
$337 nightly
The price is $379
May 25 - May 26
Total with taxes and fees
The Alfond Inn

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area
4.0 star property
Orlando
8.4 out of 10, Very Good, (6,282 reviews)
  • cleanliness
    Splash into aquatic paradise with 7 pools, a lazy river, and waterslides at this family resort.
$125 nightly
The price is $141
May 19 - May 20
Total with taxes and fees
Westgate Lakes Resort & Spa Universal Studios Area

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, (1,273 reviews)
  • cleanliness
    Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.
$71 nightly
The price is $80
May 31 - Jun 1
Total with taxes and fees
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites
3.0 star property
Florida Center
9.2 out of 10, Wonderful, (5,222 reviews)
  • cleanliness
    Splash into a family adventure at Universal's Endless Summer Resort with 2 outdoor pools, loungers, and a refreshing poolside bar.
$127 nightly
The price is $143
May 12 - May 13
Total with taxes and fees
Universal's Endless Summer Resort - Dockside Inn and Suites

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, (1,854 reviews)
  • cleanliness
    Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.
$85 nightly
The price is $96
Jun 1 - Jun 2
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando Airport

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1,374 reviews)
  • cleanliness
    Make a splash at this sun-drenched resort pool oasis with hot tub and poolside refreshments.
$81 nightly
The price is $92
May 26 - May 27
Total with taxes and fees
Embassy Suites by Hilton Orlando Lake Buena Vista South

Hilton Vacation Club Grande Villas Orlando

Hilton Vacation Club Grande Villas Orlando
3.5 star property
Orlando
9.2 out of 10, Wonderful, (2,868 reviews)
  • cleanliness
    Poolside paradise awaits with 2 sparkling outdoor pools and luxurious cabanas for ultimate relaxation.
$104 nightly
The price is $117
May 11 - May 12
Total with taxes and fees
Hilton Vacation Club Grande Villas Orlando

Hilton Grand Vacations Club SeaWorld® Orlando

Hilton Grand Vacations Club SeaWorld® Orlando
4.0 star property
Orlando
9.0 out of 10, Wonderful, (2,227 reviews)
  • cleanliness
    Luxury resort features 3 outdoor pools, 5 hot tubs, a children's pool, and poolside service.
$145 nightly
The price is $163
May 10 - May 11
Total with taxes and fees
Hilton Grand Vacations Club SeaWorld® Orlando
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.

Choose what matters most at hotels with a pool in Winter Park

Top Winter Park Hotel Reviews

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.
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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