Winter Park Vacation Rentals

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Vacation Rentals in Winter Park

Lakeview Luxury Villa with Everything
10.0 out of 10, Exceptional, (230)
"Love the place!"
Lakeview Luxury Villa with Everything
Modern Luxury Villa with Everything
9.8 out of 10, Exceptional, (292)
"My team stayed at the house for a trade show. The house was awesome, everything listed was very accurate. There was a small issue that we had to call about and the management group immediately resolved it. Would highly recommend staying here!"
Modern Luxury Villa with Everything
Quiet Oasis in Lovely Neighborhood
9.8 out of 10, Exceptional, (94)
"Nice room nice neighborhood not far from Disney"
The price is CA $123
CA $273 total
includes taxes & fees
May 28 - May 29
Quiet Oasis in Lovely Neighborhood
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Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4814)
"A great stay! Check-in was smooth and with arriving early, I had the time to wander around the airport without any issues."
The price is CA $272
CA $306 total
includes taxes & fees
May 29 - May 30
Hyatt Regency Orlando International Airport
Embassy Suites by Hilton Orlando Lake Buena Vista South
3.5 star property
9.2 out of 10, Wonderful, (1697)
"everything is excellent"
The price is CA $196
CA $223 total
includes taxes & fees
Jun 2 - Jun 3
Embassy Suites by Hilton Orlando Lake Buena Vista South
Orlando Lakefront Tiny House Community
4.5 star property
9.2 out of 10, Wonderful, (138)
"Great location. Very cozy and fun."
The price is CA $106
CA $220 total
includes taxes & fees
May 21 - May 22
Orlando Lakefront Tiny House Community
Florida Hotel & Conference Center in the Florida Mall
3.5 star property
9.0 out of 10, Wonderful, (1451)
"The hotel is beautiful. The location is super. It is very clean and everyone was very helpful and friendly. From the beautiful ladies at reception to equally beautiful lady that cleaned the room. It is certainly my go to when in the Orlando area"
The price is CA $207
CA $265 total
includes taxes & fees
May 20 - May 21
Florida Hotel & Conference Center in the Florida Mall
Sonder Vista Cay
3.5 star property
9.0 out of 10, Wonderful, (96)
"Clean, Walking distance to pool and shopping, grocery store. Everything you need conveniently. 15 min tops when driving to all outlets and theme parks. "
The price is CA $471
CA $530 total
includes taxes & fees
May 27 - May 28
Sonder Vista Cay
Wingate by Wyndham - Orlando International Airport
3.0 star property
8.8 out of 10, Excellent, (3953)
"Allowed early check in. Close to airport"
The price is CA $112
CA $126 total
includes taxes & fees
May 19 - May 20
Wingate by Wyndham - Orlando International Airport
Embassy Suites by Hilton Orlando Downtown
3.5 star property
8.8 out of 10, Excellent, (1355)
"Management went above & Beyond."
The price is CA $219
CA $247 total
includes taxes & fees
May 27 - May 28
Embassy Suites by Hilton Orlando Downtown
Hilton Garden Inn Orlando East/UCF Area
3.0 star property
8.8 out of 10, Excellent, (1218)
"Well located and clean hotel. "
The price is CA $167
CA $188 total
includes taxes & fees
Jun 2 - Jun 3
Hilton Garden Inn Orlando East/UCF Area
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
3.5 star property
8.6 out of 10, Excellent, (3119)
"Property was clean & well maintained. Pool was relaxing & clean. Loved the tiki bar & convenience of shuttle!! Shuttle has multiple times to Epcot/TTC & Disney Springs it was perfect!! Market & applebees on site was nice for after park eats & cravings! Would stay again."
The price is CA $112
CA $167 total
includes taxes & fees
Jun 9 - Jun 10
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
Floridays Resort Orlando
3.5 star property
8.6 out of 10, Excellent, (10668)
"The suit was beautiful and clean, the property was very nice and all the staff was very nice. I will be back "
The price is CA $176
CA $244 total
includes taxes & fees
May 21 - May 22
Floridays Resort Orlando
The View Studio Suites and Event Venue
3.5 star property
8.6 out of 10, Excellent, (183)
"Staff there was awesome!"
The price is CA $96
CA $108 total
includes taxes & fees
May 19 - May 20
The View Studio Suites and Event Venue
Embassy Suites by Hilton Orlando International Dr ICON Park
3.5 star property
8.6 out of 10, Excellent, (1479)
"They always brought up everything we needed. Very accommodating. "
The price is CA $119
CA $134 total
includes taxes & fees
May 19 - May 20
Embassy Suites by Hilton Orlando International Dr ICON Park
Hilton Garden Inn Orlando at SeaWorld
3.0 star property
8.6 out of 10, Excellent, (1206)
"Very nice front desk"
The price is CA $115
CA $129 total
includes taxes & fees
May 20 - May 21
Hilton Garden Inn Orlando at SeaWorld
Embassy Suites by Hilton Orlando International Dr Conv Ctr
3.5 star property
8.6 out of 10, Excellent, (1328)
" Ice rooms, close to many things that we like to take advantage of."
The price is CA $163
CA $183 total
includes taxes & fees
May 28 - May 29
Embassy Suites by Hilton Orlando International Dr Conv Ctr
Holiday Inn Express & Suites S Lake Buena Vista, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, (855)
"The personal in the breakfast "
The price is CA $128
CA $181 total
includes taxes & fees
May 22 - May 23
Holiday Inn Express & Suites S Lake Buena Vista, an IHG Hotel
Lake Buena Vista Resort Village & Spa
4.0 star property
8.4 out of 10, Very good, (7183)
"pool was great , room was large 2 bedroom condo very nice only complaint was our key cards kept not working had to go to front desk 3 times to get new cards cause none of the 4 cards we had would open the door "
The price is CA $213
CA $275 total
includes taxes & fees
May 16 - May 17
Lake Buena Vista Resort Village & Spa
Sonder at The Point
4.0 star property
8.4 out of 10, Very good, (488)
"Excellent experience, nice place ! "
The price is CA $285
CA $320 total
includes taxes & fees
Jun 14 - Jun 15
Sonder at The Point
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See all available properties in Winter Park
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.

Winter Park Vacation Rental Travel Info

Number of vacation rentals
75
Popular accommodation
Winter Park private vacation homes
Known landmarks
Orlando Science Center, Church Street Station and Orlando Museum of Art
International airport
Orlando, FL (MCO-Orlando Intl.)

Other types of properties in Winter Park you may be interested in

Universal's Endless Summer Resort - Dockside Inn and Suites
3.0 star property
9.0 out of 10, Wonderful, (5097)
"Nick at the front counter upgraded our room and provided the BEST customer service. Give that guy a raise!"
The price is CA $197
CA $221 total
includes taxes & fees
May 16 - May 17
Universal's Endless Summer Resort - Dockside Inn and Suites
DoubleTree by Hilton at the Entrance to Universal Orlando
4.0 star property
8.4 out of 10, Very good, (6357)
"Great stay and worth the price "
The price is CA $137
CA $154 total
includes taxes & fees
May 28 - May 29
DoubleTree by Hilton at the Entrance to Universal Orlando
DoubleTree by Hilton Hotel Orlando at SeaWorld
4.0 star property
7.0 out of 10, Good, (8953)
"Place is huge couple areas to do things with the family. Super closed to parks (sea world and Aquatica). Place was clean and neat bathroom did have a smell to it but nothing crazy"
The price is CA $103
CA $155 total
includes taxes & fees
May 28 - May 29
DoubleTree by Hilton Hotel Orlando at SeaWorld
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winter Park. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Winter Park?

Yes, we offer vacation rentals in Winter Park close to Kraft Azalea Gardens, or you can choose a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Winter Park. Make sure you have time to check out the university setting and gardens during your trip.

What's the top vacation rental that Winter Park has to offer?

Marriott's Sabal Palms: Visitors like this Winter Park vacation home rental. It is located near the airport and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a spa tub.

How many vacation rentals are there in Winter Park?

Expedia has 73 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens, whereas Kraft Azalea Gardens and Alfond Swimming Pool are a couple of picturesque spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are vacation rentals like in Winter Park?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Winter Park. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.

Recent reviews of Winter Park properties
Expedia verified reviews