Find Hotels with a Pool in Winter Park, FL

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Check availability on Winter Park Hotels with a Pool

Tonight
Mar 2 - Mar 3
Tomorrow
Mar 3 - Mar 4
This weekend
Mar 6 - Mar 8
Next weekend
Mar 13 - Mar 15

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.
$171 nightly
The price is $189
Apr 1 - Apr 2
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
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, (1,006 reviews)
  • cleanliness
    Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
$394 nightly
The price is $443
Mar 16 - Mar 17
Total with taxes and fees
The Alfond Inn
Aerial view

Wyndham Garden Lake Buena Vista – Disney Springs® Area

Wyndham Garden Lake Buena Vista – Disney Springs® Area
3.5 star property
Lake Buena Vista
8.2 out of 10, Very Good, (4,010 reviews)
  • cleanliness
    Splash into family-friendly fun with 2 outdoor pools and a poolside bar at this Disney Springs resort.
$130 nightly
The price is $147
Mar 3 - Mar 4
Total with taxes and fees
Wyndham Garden Lake Buena Vista – Disney Springs® Area
Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers

Universal's Stella Nova Resort

Universal's Stella Nova Resort
3.0 star property
Orlando
9.2 out of 10, Wonderful, (568 reviews)
$194 nightly
The price is $218
Mar 3 - Mar 4
Total with taxes and fees
Universal's Stella Nova Resort
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, (1,397 reviews)
  • cleanliness
    Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.
$103 nightly
The price is $116
Mar 3 - Mar 4
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando Airport
Outdoor pool, a heated pool, pool umbrellas, sun loungers

Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
3.5 star property
Orlando
8.4 out of 10, Very Good, (3,798 reviews)
  • cleanliness
    Splashy lakeside retreat with two hot tubs and a poolside tiki bar for carefree family fun in the Florida sun.
$104 nightly
The price is $117
Mar 3 - Mar 4
Total with taxes and fees
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
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, (1,577 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
Terrace/patio

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, (1,318 reviews)
  • cleanliness
    Make a splash at this sun-drenched resort pool oasis with hot tub and poolside refreshments.
$78 nightly
The price is $88
Mar 22 - Mar 23
Total with taxes and fees
Embassy Suites by Hilton Orlando Lake Buena Vista South
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
8.4 out of 10, Very Good, (959 reviews)
  • cleanliness
    Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.
$98 nightly
The price is $110
Mar 9 - Mar 10
Total with taxes and fees
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
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, (4,320 reviews)
  • cleanliness
    Dive into poolside bliss at this luxury resort with 2 hot tubs and full-service spa to rejuvenate your senses.
$114 nightly
The price is $128
Mar 8 - Mar 9
Total with taxes and fees
Rosen Centre Hotel
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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Nice and complete amenities. Very clean and well taken care of property! Would definitely return!"
Dan 5-night trip
Posted 2 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

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 $88 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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