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 2 - Sep 3
Tomorrow
Sep 3 - Sep 4
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Winter Park hotels with a pool

A multi-story hotel with balconies, a swimming pool, and a landscaped courtyard.
An outdoor dining area with tables and chairs, string lights, and a building with arches and balconies.
A spacious lobby with a high ceiling, large windows, and a grand piano.
A hotel with multiple floors, outdoor seating areas, and a well-lit courtyard.

1. The Alfond Inn

The Alfond Inn
Winter Park
  • Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
$258 nightly
$290 total
Sep 13 - Sep 14
Total with taxes and fees
The Alfond Inn
A swimming pool with a curved edge, surrounded by a concrete deck and a brick border.
An outdoor air conditioning unit mounted on a yellow wall, a brick planter with a potted plant, and a white door.
A shower with a glass door, a white shower curtain, and a black floor mat.
A bedroom with a bed, a nightstand, a lamp, and a ceiling fan.

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.
$154 nightly
$170 total
Oct 2 - Oct 3
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
A modern kitchen with white cabinets, stainless steel appliances, and a black dining chair.
A residential house with a paved driveway, solar panels on the roof, and a well-maintained lawn.
A bathroom with a shower, toilet, and a white sink with a mirror above it. There are potted plants on a metal shelf above the sink.
A modern living room with a beige sofa, a black office chair, a small side table with a lamp, and a ceiling fan.

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
$262 nightly
$291 total
Sep 5 - Sep 6
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
A swimming pool with wooden deck seating, palm trees, and a modern building in the background.
A multi-story hotel with a modern design, featuring balconies and a covered entrance.
An outdoor patio area with wicker furniture, a glass table, and a view of a building in the background.

4. 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 5 - Sep 6
Total with taxes and fees
Courtyard by Marriott Orlando Downtown
A pool area with a hot tub, lounge chairs, and a covered seating area.
A spacious lobby with a reception desk, seating area with sofas and armchairs, and large windows allowing natural light.
A hotel room with a blue sofa, a wooden desk, a TV, and a lamp.
A hotel entrance with a covered area, palm trees, and an American flag.

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
$130 total
Sep 23 - Sep 24
Total with taxes and fees
Comfort Suites Downtown
A swimming pool with lounge chairs and umbrellas, a building with multiple windows, and palm trees.
A modern living room with a sofa, chairs, a fireplace, and a flat-screen TV mounted on the wall.
A hotel room with a bed, desk, chair, and a sofa.
A reception area with a pool view mural, two reception desks, and a waiting area with chairs.

6. 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
$92 total
Sep 7 - Sep 8
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando UCF
A hotel pool area with lounge chairs, umbrellas, and a swimming pool.
An outdoor seating area with green chairs and umbrellas, a fire pit, and a building with large windows in the background.
A bar area with a long counter, multiple seating options, and a television screen.
A hotel room with a sofa, two armchairs, a coffee table, and a wall-mounted sign reading "gateway village - ORLANDO stay a while".

7. 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 7 - Sep 8
Total with taxes and fees
Hampton Inn & Suites Orlando Airport @ Gateway Village
A hot tub with a waterfall mural, a metal ladder, and a tiled floor.
A modern hotel room with a large white bathtub, a neatly made bed, and a small bedside table with a lamp.
A bathroom with a granite countertop, a sink, a mirror, a framed picture, and a shower curtain.
A modern restaurant with multiple dining tables and chairs, a bar area, and a television mounted on the wall.

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.
$75 nightly
$84 total
Sep 3 - Sep 4
Total with taxes and fees
Wingate by Wyndham - Orlando International Airport
A hotel pool area with a large pool, lounge chairs, and a building with multiple windows and balconies.
A reception area with a modern design, featuring a reception desk, a large floral wall art, and a seating area with a sofa and armchairs.
A hotel room with a bed, a desk, a chair, a sofa, and a TV.
A buffet area with a microwave, coffee maker, and various food containers.

9. La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport
Airport North
  • Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.
$71 nightly
$80 total
Sep 24 - Sep 25
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando Airport
A swimming pool with lounge chairs and umbrellas, surrounded by a multi-story building with balconies.
An outdoor patio area with seating, a bar, and a fire feature.
A hotel room with two beds, a desk, a chair, a lamp, and two paintings on the wall.
A modern hotel with a blue facade, a covered entrance, and palm trees in the foreground.

10. Hyatt House Orlando Airport

Hyatt House Orlando Airport
Airport North
  • Refreshing outdoor pool sanctuary awaits near Florida Mall, with a firepit and poolside lounging for a sunny getaway experience.
$110 nightly
$124 total
Sep 9 - Sep 10
Total with taxes and fees
Hyatt House 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

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Great value for money."
Nicholas 14-night trip
Posted less than an hour ago
Drury Plaza Hotel Orlando - Disney Springs Area
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Hotel was just opposite of Universal Studios Orlando. And had shuttle service which was great. Clean room, lobby. Easy to access and close to all areas of attractions. Loved it."
Shahrin 2-night trip
Posted less than an hour ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Sonesta ES Suites Orlando - Lake Buena Vista

Sonesta ES Suites Orlando - Lake Buena Vista

10/10 Excellent
"Loved the location, facillities, staff were amazing and had a wonderful stay"
Haralee 4-night trip
Posted 3 hours ago
Sonesta ES Suites Orlando - Lake Buena Vista
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

8/10 Good
"S"
Victor 5-night trip
Posted 4 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Marriott's Grande Vista

Marriott's Grande Vista

8/10 Good
"Did not know the parking was $30 per day"
Jeffrey 3-night trip
Posted 6 hours ago
Marriott's Grande Vista
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"The rooms are clean, the staff is friendly and helpful. The cost is very reasonable. The location is perfect for going to the theme parks."
Dustin 2-night trip
Posted 7 hours ago
Rosen Inn Lake Buena Vista
Avanti International Resort

Avanti International Resort

10/10 Excellent
"none"
Edgar 2-night trip
Posted 8 hours ago
Avanti International Resort
Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

10/10 Excellent
"family friendly"
jose 3-night trip
Posted 1 day ago
Coco Key Hotel & Water Park Resort

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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