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

Tonight
Sep 6 - Sep 7
Tomorrow
Sep 7 - Sep 8
Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20

Our top choices for Winter Park hotels with a pool

Exterior
Breakfast, dinner and brunch served
Terrace/patio
Meeting facility

1. The Alfond Inn

The Alfond Inn
Winter Park
  • Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
$296 nightly
$333 total
Sep 7 - Sep 8
Total with taxes and fees
The Alfond Inn
Outdoor pool
Coffee/tea maker, fridge, microwave, oven
Smart TV, fireplace, stereo
Dining

2. The Canopy on Periwinkle- A Home Away From Home

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
$312 nightly
$347 total
Sep 20 - Sep 21
Total with taxes and fees
The Canopy on Periwinkle- A Home Away From Home
Outdoor pool
Hair dryer, towels, soap, shampoo
Terrace/patio
Property grounds

3. 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
  • Relax poolside at a cozy retreat with both private and outdoor pools, just 12 minutes from University of Central Florida.
$148 nightly
$164 total
Oct 6 - Oct 7
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
Coffee/tea maker, fridge, microwave, oven
Dining
Smart TV
Shower, hair dryer, towels, soap

4. 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
$267 nightly
$296 total
Sep 7 - Sep 8
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
Seasonal outdoor pool
Suite, 2 Double Beds, Non Smoking | Desk, blackout drapes, iron/ironing board, WiFi (free)
Exterior
Desk, blackout drapes, iron/ironing board, WiFi (free)

5. Comfort Suites Downtown

Comfort Suites Downtown
Ivanhoe Village
  • Make a splash in downtown Orlando with this hotel's seasonal outdoor pool and relaxing hot tub for post-exploration recovery.
$115 nightly
$129 total
Sep 28 - Sep 29
Total with taxes and fees
Comfort Suites Downtown
Outdoor pool, open 6:00 AM to 11:00 PM, pool umbrellas, sun loungers
BBQ/picnic area
Exterior
Breakfast, lunch and dinner served

6. Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown
Ivanhoe Village
  • Float in sunshine at downtown Orlando's chic hotel pool, surrounded by plush loungers and umbrellas.
$122 nightly
$138 total
Sep 10 - Sep 11
Total with taxes and fees
Courtyard by Marriott Orlando Downtown
Outdoor pool
Lobby
Lobby
Deluxe Suite, 1 King Bed, Non Smoking, Pool View | Premium bedding, down comforters, pillowtop beds, desk

7. La Quinta Inn & Suites by Wyndham Orlando UCF

La Quinta Inn & Suites by Wyndham Orlando UCF
Orlando
  • Sun-soaked outdoor pool offers refreshing escapes and hot tub relaxation near the University of Central Florida campus.
$82 nightly
$93 total
Sep 9 - Sep 10
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando UCF
Outdoor pool, sun loungers
Lobby
Restaurant
Superior Studio Suite, 1 King Bed, Non Smoking, Jetted Tub | Jetted tub

8. Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport
Airport North
  • Refreshing outdoor pool oasis with sun loungers offers relaxation after exploring nearby shopping and dining options.
$78 nightly
$88 total
Sep 8 - Sep 9
Total with taxes and fees
Wingate by Wyndham - Orlando International Airport
Outdoor pool
Bar (on property)
Lobby
Exterior

9. Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village
Airport North
  • Vibrant pool oasis near Orlando Airport beckons travelers to dive in after a day exploring nearby attractions.
$89 nightly
$101 total
Sep 13 - Sep 14
Total with taxes and fees
Hampton Inn & Suites Orlando Airport @ Gateway Village
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Free daily continental breakfast
In-room safe, desk, iron/ironing board, WiFi (free)
In-room safe, desk, iron/ironing board, WiFi (free)

10. Fairfield Inn By Marriott Orlando Airport

Fairfield Inn By Marriott Orlando Airport
Airport North
  • Splash into this refreshing outdoor retreat with crystal-clear waters and a rejuvenating hot tub after airport arrivals.
$84 nightly
$95 total
Sep 9 - Sep 10
Total with taxes and fees
Fairfield Inn By Marriott Orlando Airport
View all properties

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

Breakfast included
Hot tub
Water park
Spa
4 stars

Top Winter Park Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"First time staying here and we loved it! We came down to Orlando to celebrate our daughter and our only regret is not staying longer. Very clean, beautiful property, staff was great!"
Vanessa 2-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"We had two balcony rooms, very clean and accommodating to our needs."
Heather 1-night trip
Posted 2 hours ago
Hyatt Regency Orlando International Airport
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"The best off property place to stay."
Leslie 3-night trip
Posted 6 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

8/10 Good
"Muy bueno para ir con niños"
Orestes 2-night trip
Posted 12 hours ago
Westgate Lakes Resort & Spa Universal Studios Area
Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite

10/10 Excellent
"Great hotel clean and with great customer service"
JENNIFER 2-night trip
Posted 13 hours ago
Caribe Royale Orlando, WorldHotels Elite
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"Friendly, Clean, Nice Breakfast"
Airriona 3-night trip
Posted 15 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Every thing was great"
Ruben 1-night trip
Posted 18 hours ago
Rosen Inn Lake Buena Vista

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.
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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