Winter Park Vacation Rentals

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In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
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Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Winter Park

Floridays Resort Orlando
2 outdoor pools, a heated pool, open 7:00 AM to 11:00 PM, pool umbrellas

Floridays Resort Orlando

3.5 star property
8.6 out of 10, Excellent, (11530)
"The size of the unit was great, it was quite and the pools and restaurants were great "
The price is ￥21,512
￥30,099 total
includes taxes & fees
Sep 28 - Sep 29
Floridays Resort Orlando
Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (9193)
"Amazing stay "
Lake Buena Vista Resort Village & Spa
The View Studio Suites and Event Venue
Lobby sitting area

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (1294)
"I really enjoyed my stay. Very nice room and the staff was friendly and accommodating. Very good breakfast"
The price is ￥12,803
￥14,403 total
includes taxes & fees
Sep 28 - Sep 29
The View Studio Suites and Event Venue
Florida Hotel & Conference Center in the Florida Mall
Reception

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.2 out of 10, Wonderful, (2144)
"Great location"
The price is ￥18,601
￥24,802 total
includes taxes & fees
Sep 27 - Sep 28
Florida Hotel & Conference Center in the Florida Mall
The Point Hotel & Suites
Outdoor pool

The Point Hotel & Suites

3.5 star property
8.0 out of 10, Very Good, (3275)
"Room looked just like the photos online. Very comfortable and clean. "
The price is ￥13,148
￥16,514 total
includes taxes & fees
Sep 30 - Oct 1
The Point Hotel & Suites
Blue Tree Resort at Lake Buena Vista
Outdoor spa tub

Blue Tree Resort at Lake Buena Vista

3.0 star property
8.6 out of 10, Excellent, (1796)
"Very nice resort would stay again."
Blue Tree Resort at Lake Buena Vista
The Point by Edge
Terrace/patio

The Point by Edge

4.0 star property
8.4 out of 10, Very Good, (784)
"Gorgeous room and friendly staff."
The price is ￥11,402
￥14,680 total
includes taxes & fees
Oct 5 - Oct 6
The Point by Edge
Vista Cay Resort by Millenium at Universal Blvd
2 outdoor pools, pool umbrellas, sun loungers

Vista Cay Resort by Millenium at Universal Blvd

3.5 star property
8.6 out of 10, Excellent, (1552)
"Enjoy my stay always "
Vista Cay Resort by Millenium at Universal Blvd
Parc Corniche Condominium Suite Hotel
Exterior

Parc Corniche Condominium Suite Hotel

3.0 star property
8.0 out of 10, Very Good, (2169)
"Is close to Seaworld and Aquatica, good option to stay in this hotel "
The price is ￥11,308
￥20,304 total
includes taxes & fees
Sep 29 - Sep 30
Parc Corniche Condominium Suite Hotel
Sonder by Marriott Bonvoy Vista Cay Apartments
Outdoor pool

Sonder by Marriott Bonvoy Vista Cay Apartments

3.5 star property
9.0 out of 10, Wonderful, (247)
"I love this property it was clean and the pool was fabulous. The concierge was helpful and friendly i definitely will be staying there again"
The price is ￥15,147
￥17,040 total
includes taxes & fees
Oct 27 - Oct 28
Sonder by Marriott Bonvoy Vista Cay Apartments
Century Millenia
Apartment, 2 Bedrooms | Private kitchen | Toaster

Century Millenia

3.0 star property
9.0 out of 10, Wonderful, (87)
"Perfect stay for family or any vacation"
Century Millenia
Wellborn Hotel Downtown, Sonder by Marriott Bonvoy
Property amenity

Wellborn Hotel Downtown, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very Good, (309)
"The staff was great, the room was really nice and comfortable, the ambiance was great "
The price is ￥16,038
￥18,044 total
includes taxes & fees
Oct 19 - Oct 20
Wellborn Hotel Downtown, Sonder by Marriott Bonvoy
Blue Heron Beach Resort
Front of property

Blue Heron Beach Resort

3.5 star property
8.4 out of 10, Very Good, (2961)
"I. Loved to stay"
Blue Heron Beach Resort
WorldQuest Orlando Resort
Outdoor pool, pool umbrellas, sun loungers

WorldQuest Orlando Resort

4.0 star property
8.4 out of 10, Very Good, (4005)
"Always love staying here with my family and friends for over 10 years now great location for Disney parks and easy to get groceries and dining options. Close to Vinland shopping as well."
WorldQuest Orlando Resort
Enchanted Dreams
Full-size fridge, microwave, oven, stovetop

Enchanted Dreams

3.5 star property
8.0 out of 10, Very Good, (4)
"Clean, comfortable home. Everything was excellent from the security to amenities. I will book again, share with friends and family. "
The price is ￥8,760
￥20,140 total
includes taxes & fees
Sep 28 - Sep 29
Enchanted Dreams
staySky Suites - I Drive Orlando
Outdoor pool, sun loungers

staySky Suites - I Drive Orlando

3.0 star property
7.8 out of 10, Good, (1230)
"Excellent option for those visiting the park "
The price is ￥11,406
￥13,835 total
includes taxes & fees
Oct 2 - Oct 3
staySky Suites - I Drive Orlando
Premium Condos near Universal Studios
Indoor pool, 2 outdoor pools, open 8:00 AM to 8:00 PM, pool umbrellas

Premium Condos near Universal Studios

3.5 star property
9.0 out of 10, Wonderful, (20)
"Room was very clean and modern and at a perfect spot for us, it was quiet throughout the duration until the last day before checkout where a lot of maintenance was happening and guest above us started slamming and stomping around. It was a little agitating to watch TV when everyone in the hotel keeps connecting to the TV and interrupting our show. The hotel has the perfect location for the parks, universal and Disney with only 20 minute drive and 40 minute walk to universal. Hotel is close to...
The price is ￥11,696
￥23,097 total
includes taxes & fees
Oct 13 - Oct 14
Premium Condos near Universal Studios
Orlando's Sunshine Resort
BBQ/picnic area

Orlando's Sunshine Resort

3.5 star property
9.2 out of 10, Wonderful, (232)
"great location "
Orlando's Sunshine Resort
Marriott's Sabal Palms
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers

Marriott's Sabal Palms

4.0 star property
9.6 out of 10, Exceptional, (202)
"Easy check in, pool was awesome "
The price is ￥33,394
￥37,568 total
includes taxes & fees
Oct 27 - Oct 28
Marriott's Sabal Palms
Modern Luxury Villa with Everything
TV, foosball, stereo

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (439)
"It was a great stay. The house was clean and close to everything."
Modern Luxury Villa with Everything
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.
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Top Winter Park Hotel Reviews

DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

10/10 Excellent
"This hotel is perfectly located and gives access to Orlando."
Jose Alejandro 3-night trip
Posted 15 hours ago
DoubleTree by Hilton Hotel Orlando at SeaWorld

Find out more about Winter Park

Find out more about Winter Park

Search for holiday rentals in Winter Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Park using one of the methods below:

  • View our selection of featured holiday rentals in Winter Park
  • Use the map to find apartments and other holiday homes in the Winter Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Park while they last

Look no further and take a look at our great range of rental properties in Winter Park!

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. Kick off your shoes and enjoy yourself with an outdoor tennis court and a hot tub.

How many vacation rentals are there in Winter Park?

Expedia has 64 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 Lake Virginia 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.