Winter Park Holiday Rentals

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Holiday Rentals in Winter Park

1-bedroom vacation home just 12 minutes from University of Central Florida

The price is NZ$286
includes taxes & fees
22 July - 23 July
1-bedroom vacation home just 12 minutes from University of Central Florida

Magic Studio

10.0 out of 10, Exceptional, (2)
"Clean, roomy for two, comfortable bed, Met all our needs. Plan to stay there again."
The price is NZ$287
includes taxes & fees
28 July - 29 July
Magic Studio

Winter Park Charmer - Heated Pool Home - Close to everything

8.4 out of 10, Very good, (10)
"Property was in quiet area. Clean and easy to get to other areas of interest. Comfortable beds. Great pool! "
The price is NZ$660
includes taxes & fees
23 July - 24 July
Winter Park Charmer - Heated Pool Home - Close to everything

Mills House @WP. Sleeps 11 Renovated. Queen beds

10.0 out of 10, Exceptional, (1)
"This was a quaint little place with plenty of sleeping. The fenced in back yard with a canopy cover and chairs was a nice bonus. The kitchen was sufficiently stocked and newly remodeled. There were new smart TV ‘s in each room. There was a Publix right up the road as well as lots of great restaurants. We also enjoyed an antique mall (in the Publix plaza). We would highly recommend this place to others ."
The price is NZ$546
includes taxes & fees
3 Aug - 4 Aug
Mills House @WP. Sleeps 11 Renovated. Queen beds

Charming 3-bedroom house with WiFi, AC in welcoming Winter Park

The price is NZ$716
includes taxes & fees
27 July - 28 July
Charming 3-bedroom house with WiFi, AC in welcoming Winter Park

Banana Leaf Villa-Vintage Vibes Premium Room

2.0 star property
8.0 out of 10, Very good, (4)
"This is the perfect getaway spot! Very accessible, quiet area. I will definitely be booking again."
The price is NZ$201
includes taxes & fees
22 July - 23 July
Banana Leaf Villa-Vintage Vibes Premium Room

Tranquil 3-bedroom house in Sanford with AC, WiFi

9.8 out of 10, Exceptional, (17)
"Beautiful place to stay near the airport "
The price is NZ$401
includes taxes & fees
22 July - 23 July
Tranquil 3-bedroom house in Sanford with AC, WiFi

Sunshine Escape Guesthouse ☀

9.6 out of 10, Exceptional, (9)
"Great place to stay to get away for the weekend. Quiet neighborhood not far fromPark Ave "
The price is NZ$267
includes taxes & fees
22 July - 23 July
Sunshine Escape Guesthouse ☀

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (2)
"The house was exactly as shown. It was very clean and really nice. Great space for parking my large trailer. The neighborhood was nice and very quiet. We would definitely stay again."
The price is NZ$252
includes taxes & fees
28 July - 29 July
Charming 2-bedroom Country Cottage in Kissimmee with private parking

Charming 3-bedroom home away from home.

9.8 out of 10, Exceptional, (16)
"Perfect stay while visiting local family. "
The price is NZ$625
includes taxes & fees
25 July - 26 July
Charming 3-bedroom home away from home.

Lakeview Tiny House Near Airport & Universal in Kissimmee Orlando FL

10.0 out of 10, Exceptional, (5)
The price is NZ$250
includes taxes & fees
22 July - 23 July
Lakeview Tiny House Near Airport & Universal in Kissimmee Orlando FL

Modern Home Near Downtown

10.0 out of 10, Exceptional, (1)
"Host was friendly and great with communication. Easy check in process! "
The price is NZ$291
includes taxes & fees
31 July - 1 Aug
Modern Home Near Downtown

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

9.8 out of 10, Exceptional, (6)
"This place is a great size guest suite on a scenic property in a rural area close to the suburbs, very nice getaway, we enjoyed our short stay! It's very clean and cozy, and the hosts are very helpful, thank you!"
The price is NZ$260
includes taxes & fees
5 Aug - 6 Aug
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Renovated Peaceful Luxury Walk to Mall Park Publix

9.4 out of 10, Exceptional, (10)
"Very nice little place walking distance to Advent Health."
The price is NZ$323
includes taxes & fees
22 July - 23 July
Renovated Peaceful Luxury Walk to Mall Park Publix

The Cozy Crash Pad: Tiny House Experience

9.2 out of 10, Wonderful, (19)
"It was incredible! The tiny home feels incredibly cozy and was super easy to find. We had a wonderful visit."
The price is NZ$237
includes taxes & fees
27 July - 28 July
The Cozy Crash Pad: Tiny House Experience

Pet Friendly!✰ Charming home with big patio!

10.0 out of 10, Exceptional, (13)
"Excellent stay. Five starts across the board."
The price is NZ$600
includes taxes & fees
28 July - 29 July
Pet Friendly!✰ Charming home with big patio!

Quiet Oasis in Lovely Neighborhood

9.8 out of 10, Exceptional, (140)
"We had an amazing stay here and wished we could have stayed longer, everything was perfect and we are so grateful."
The price is NZ$300
includes taxes & fees
24 July - 25 July
Quiet Oasis in Lovely Neighborhood

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

10.0 out of 10, Exceptional, (29)
"Great property and host "
The price is NZ$422
includes taxes & fees
22 July - 23 July
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

URBAN OASIS: Dog Friendly - Bungalow Retreat - Downtown Orlando

10.0 out of 10, Exceptional, (1)
"This place was perfect for our stay for my niece's graduation. Close to everything, super new and clean. Lots of space for the 3 of us in a nice, quiet neighborhood."
The price is NZ$641
includes taxes & fees
23 July - 24 July
URBAN OASIS: Dog Friendly - Bungalow Retreat - Downtown Orlando

“The Clementine” Boho Home in Orlando’s Food Scene

9.6 out of 10, Exceptional, (13)
"Great"
The price is NZ$248
includes taxes & fees
22 July - 23 July
“The Clementine” Boho Home in Orlando’s Food Scene
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

Frequently asked questions

Can I find holiday rentals in Winter Park?

Yes, there are holiday rentals in Winter Park close to Kraft Azalea Gardens, or you can select 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 are some of the best holiday rentals that Winter Park has to offer?

Marriott's Sabal Palms: This holiday home rental outside of Winter Park is located near the airport, and has an outdoor pool, a balcony and a BBQ 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 1 hot tub.

How many holiday rentals are there in Winter Park?

Expedia has 64 holiday 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 holiday rentals like in Winter Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Park. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.