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 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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 hall with a grand piano, large windows, and a central floral arrangement.
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.
$326 nightly
$367 total
Sep 27 - Sep 28
Total with taxes and fees
The Alfond Inn
A rectangular swimming pool with clear blue water, surrounded by a beige deck and a white fence.
A modern living room with a ceiling fan, a flat-screen TV, and a dining area with a white table and chairs.
A bedroom with a bed, bedside tables, a mirror, and a ceiling fan.
A modern kitchen with white cabinetry, a stainless steel sink, a gas stove, and a tiled backsplash.

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

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
$325 nightly
$361 total
Sep 24 - Sep 25
Total with taxes and fees
The Canopy on Periwinkle- A Home Away From Home
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 dining table with four chairs, each with a white doily and a yellow plate.

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
Sep 24 - Sep 25
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
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 covered patio area with outdoor furniture, a grill, and potted plants.

4. 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 4 - Oct 5
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
A pool area with a hot tub, lounge chairs, and a covered seating area.
A hotel room with two beds, a blue sofa, a wooden table, and framed pictures on the wall.
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.
$122 nightly
$137 total
Sep 27 - Sep 28
Total with taxes and fees
Comfort Suites Downtown
A swimming pool with wooden deck seating, palm trees, and a modern building in the background.
An outdoor patio area with wicker furniture, a glass table, and a view of a building in the background.
A modern living room with a large flat-screen TV, blue sofas, a round coffee table, and a bookshelf.

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.
$127 nightly
$142 total
Sep 28 - Sep 29
Total with taxes and fees
Courtyard by Marriott Orlando Downtown
A swimming pool with lounge chairs and umbrellas, a building with multiple windows, and palm trees.
A hotel room with a bed, desk, chair, and a sofa.
A hallway with a dark wood console table, a green vase, and framed artwork on the wall. A sign indicates the direction to the fitness center, ice machine, and AV room.
A modern living room with a sofa, chairs, a fireplace, and a flat-screen TV mounted on the wall.

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.
$88 nightly
$98 total
Oct 18 - Oct 19
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando UCF
A hotel pool area with a large pool, lounge chairs, and a building with multiple windows and balconies.
A hotel with a prominent tower, palm trees, and a red roof.
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.

8. 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.
$67 nightly
$75 total
Oct 1 - Oct 2
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Orlando Airport
A hot tub with a waterfall mural, a metal ladder, and a tiled floor.
A modern lounge area with a sofa set, ottomans, and a small table.
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.

9. 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.
$86 nightly
$96 total
Sep 28 - Sep 29
Total with taxes and fees
Wingate by Wyndham - Orlando International Airport
A reception area with a curved wooden counter, a glass display case with beverages, and a wall mural with a wave pattern.
A modern bathroom with a bathtub, toilet, and sink.
A hotel room with a sofa, two beds, a TV, a window with a view, and a bathroom.
A Hyatt Place hotel entrance with a covered walkway, glass doors, and a landscaped area with trees and shrubs.

10. Hyatt Place Lake Mary/Orlando North

Hyatt Place Lake Mary/Orlando North
Lake Mary
  • Spacious outdoor pool and hot tub create a relaxing oasis with nearby recreational activities in this centrally located hotel.
$92 nightly
$105 total
Sep 24 - Sep 25
Total with taxes and fees
Hyatt Place Lake Mary/Orlando North
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

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"Great stay! Will be back!"
Alicia 2-night trip
Posted less than an hour ago
Hyatt Regency Orlando International Airport
Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

8/10 Good
"The hotel is been remodeling so, you may find some unfinished stuff. Like the bathroom did not have a shelf for towels,. It was nicely cleaned and staff very nice. Close to many restaurants."
Rucvicet 2-night trip
Posted 2 hours ago
Coco Key Hotel & Water Park Resort
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Great place to stay with the family."
Vanessa 7-night trip
Posted 3 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"All was excellent."
Vanessa 6-night trip
Posted 5 hours ago
Marriott's Grande Vista
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Nice place to stay and very convenient."
Angie 4-night trip
Posted 8 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

10/10 Excellent
"Big, clean room with great A/C, beds and amenities. Friendly and helpful staff. Great location-walking distance to Disney Springs, great breakfast and afternoon meal/drinks. Will be back."
Sheri 1-night trip
Posted 12 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

8/10 Good
"Everything was good except for the fact that the parking was full on Friday night and Saturday night but other than that everything else was amazing we had such a great time I would definitely book again"
Pennee 3-night trip
Posted 14 hours ago
Lake Buena Vista Resort Village & Spa

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 $75 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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