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Find Hotels with a Pool in Winter Park, FL

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Check availability on Winter Park Hotels with a Pool

Tonight
Aug 8 - Aug 9
Tomorrow
Aug 9 - Aug 10
Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23

Our top choices for Winter Park hotels with a pool

Exterior
Breakfast, dinner and brunch served
Lobby sitting area
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.
$316 nightly
$356 total
Aug 10 - Aug 11
Total with taxes and fees
The Alfond Inn
Outdoor pool
1 bedroom, iron/ironing board, WiFi (free), bed sheets
Terrace/patio
Hair dryer, towels, soap, shampoo

2. 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
Aug 10 - Aug 11
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
Shower, hair dryer, towels, soap
Dining
Coffee/tea maker, fridge, microwave, oven
Outdoor pool

3. 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
$263 nightly
$292 total
Aug 9 - Aug 10
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
A heated pool
4 bedrooms, iron/ironing board, travel crib, WiFi (free)
Smart TV
Hair dryer, towels

4. Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park Charmer - Heated Pool Home - Close to everything
Winter Park
$382 nightly
$422 total
Aug 15 - Aug 16
Total with taxes and fees
Winter Park Charmer - Heated Pool Home - Close to everything
Outdoor pool
4 bedrooms, desk, iron/ironing board, WiFi (free)
Smart TV, fireplace, stereo
Dining

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

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
$424 nightly
$471 total
Aug 15 - Aug 16
Total with taxes and fees
The Canopy on Periwinkle- A Home Away From Home
Seasonal outdoor pool
Lobby
Suite, 2 Double Beds, Non Smoking | Desk, blackout drapes, iron/ironing board, WiFi (free)
Exterior

6. 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.
$105 nightly
$119 total
Aug 30 - Aug 31
Total with taxes and fees
Comfort Suites Downtown
Outdoor pool, open 6:00 AM to 11:00 PM, pool umbrellas, sun loungers
Breakfast, lunch and dinner served
BBQ/picnic area
Exterior

7. 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.
$127 nightly
$142 total
Aug 11 - Aug 12
Total with taxes and fees
Courtyard by Marriott Orlando Downtown
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers
Bar (on property)
Lobby lounge
Lobby sitting area

8. Hilton Orlando/Altamonte Springs

Hilton Orlando/Altamonte Springs
Altamonte Springs
  • Sink into pure bliss at this outdoor pool with loungers for a refreshing Florida getaway.
$110 nightly
$125 total
Aug 30 - Aug 31
Total with taxes and fees
Hilton Orlando/Altamonte Springs
Outdoor pool
Lobby
Deluxe Suite, 1 King Bed, Non Smoking, Pool View | Premium bedding, down comforters, pillowtop beds, desk
Lobby

9. 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.
$83 nightly
$93 total
Sep 6 - Sep 7
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando UCF
Outdoor pool, sun loungers
Lobby
Superior Studio Suite, 1 King Bed, Non Smoking, Jetted Tub | Jetted tub
Restaurant

10. 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.
$80 nightly
$90 total
Aug 9 - Aug 10
Total with taxes and fees
Wingate by Wyndham - Orlando International 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

Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"Property was clean and staff was very friendly and helpful."
Jason 1-night trip
Posted less than an hour ago
Marriott's Grande Vista
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Clean room Great service"
prince 3-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"I really like that it was so close to everything especially the parks."
Cintia 4-night trip
Posted 2 hours ago
Westgate Lakes Resort & Spa Universal Studios Area
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Excellent location. Super Accommodating Staff. Easy Check-In/Out."
Jorge 6-night trip
Posted 3 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

8/10 Good
"Front desk was definitely super helpful and friendly. Breakfast and kickback hour is a plus."
Azucena 2-night trip
Posted 4 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Signia by Hilton Orlando - An Official Walt Disney World® Hotel

Signia by Hilton Orlando - An Official Walt Disney World® Hotel

10/10 Excellent
"Staff was amazing!!! Rooms were clean and spacious. Pool was very nice. Views were amazing. Bathroom mirror very large. Breakfast amazing definitely a 10/10, and the hotel is pet friendly."
Lavonya 2-night trip
Posted 4 hours ago
Signia by Hilton Orlando - An Official Walt Disney World® Hotel
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"Todo en orden"
Manuel 2-night trip
Posted 5 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

8/10 Good
"The service is 11 out of 10. The best of the whole experience was the service."
maria J. 1-night trip
Posted 1 day ago
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

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.
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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