Find Hotels with a Pool in Winter Park, FL

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Check availability on Winter Park Hotels with a Pool

Tonight
Apr 27 - Apr 28
Tomorrow
Apr 28 - Apr 29
This weekend
May 1 - May 3
Next weekend
May 8 - May 10

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.
$153 nightly
The price is $169
May 11 - May 12
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
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)
$261 nightly
The price is $290
Apr 29 - Apr 30
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, (1,004 reviews)
  • cleanliness
    Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
$324 nightly
The price is $365
May 3 - May 4
Total with taxes and fees
The Alfond Inn
Water park

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, (6,260 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 14 - May 15
Total with taxes and fees
Westgate Lakes Resort & Spa Universal Studios Area
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, (1,242 reviews)
  • cleanliness
    Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.
$70 nightly
The price is $78
May 18 - May 19
Total with taxes and fees
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Exterior

Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
4.0 star property
Orlando
9.0 out of 10, Wonderful, (2,917 reviews)
  • cleanliness
    Splash into aquatic bliss at this resort with 5 outdoor pools, a lazy river, and poolside cabanas.
$198 nightly
The price is $223
May 24 - May 25
Total with taxes and fees
Wyndham Grand Orlando Resort Bonnet Creek
2 outdoor pools, pool umbrellas, sun loungers

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, (5,220 reviews)
  • cleanliness
    Splash into a family adventure at Universal's Endless Summer Resort with 2 outdoor pools, loungers, and a refreshing poolside bar.
$132 nightly
The price is $149
May 5 - May 6
Total with taxes and fees
Universal's Endless Summer Resort - Dockside Inn and Suites
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, (1,750 reviews)
  • cleanliness
    Sun-kissed relaxation awaits at this poolside oasis with loungers and shade umbrellas.
$101 nightly
The price is $114
May 4 - May 5
Total with taxes and fees
Hyatt House Orlando International Drive
Outdoor banquet area

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4,716 reviews)
  • cleanliness
    Swim in luxury with four sparkling pools and poolside cabanas at this golf resort haven.
$104 nightly
The price is $117
May 9 - May 10
Total with taxes and fees
Rosen Shingle Creek
Exterior

Hilton Vacation Club Grande Villas Orlando

Hilton Vacation Club Grande Villas Orlando
3.5 star property
Orlando
9.2 out of 10, Wonderful, (2,857 reviews)
  • cleanliness
    Poolside paradise awaits with 2 sparkling outdoor pools and luxurious cabanas for ultimate relaxation.
$104 nightly
The price is $117
May 4 - May 5
Total with taxes and fees
Hilton Vacation Club Grande Villas 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.
View all properties

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

Breakfast included
Hot tub

Top Winter Park Hotel Reviews

B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

10/10 Excellent
"😊"
Adrienne 3-night trip
Posted 2 hours ago
B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

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 $78 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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