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 AU$267
includes taxes & fees
25 June - 26 June
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 AU$267
includes taxes & fees
12 July - 13 July
Magic Studio

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 AU$543
includes taxes & fees
30 June - 1 July
Mills House @WP. Sleeps 11 Renovated. Queen beds

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

The price is AU$670
includes taxes & fees
25 June - 26 June
Charming 3-bedroom house with WiFi, AC in welcoming Winter Park

Charming 3-bedroom home away from home.

9.8 out of 10, Exceptional, (16)
"We enjoyed our stay. The house was very clean as advertised and our host was amazing. "
The price is AU$580
includes taxes & fees
25 June - 26 June
Charming 3-bedroom home away from home.

Above the Barn at Rustic Pines

The price is AU$311
includes taxes & fees
25 June - 26 June
Above the Barn at Rustic Pines

Pet Friendly!✰ Charming home with big patio!

10.0 out of 10, Exceptional, (11)
"Excellent stay. Five starts across the board."
The price is AU$554
includes taxes & fees
28 June - 29 June
Pet Friendly!✰ Charming home with big patio!

Brand NewPainted Vacation Hse NrUCF PetsOK Fenced

9.6 out of 10, Exceptional, (15)
"We had a great stay at this lovely home. Very clean and well supplied. Our dog thoroughly enjoyed the backyard. Home is located near a lot of great places to eat and shop."
The price is AU$443
includes taxes & fees
1 July - 2 July
Brand NewPainted Vacation Hse NrUCF PetsOK Fenced

Eastpark. Pet friendly! Lake Nona

9.2 out of 10, Wonderful, (81)
"Great place along with great host"
The price is AU$477
includes taxes & fees
25 June - 26 June
Eastpark. Pet friendly! Lake Nona

Spacious & Private Guest Pool House Oasis

9.6 out of 10, Exceptional, (13)
"Thank you it was a wonderful peaceful stay. "
The price is AU$411
includes taxes & fees
25 June - 26 June
Spacious & Private Guest Pool House Oasis

The Cozy Crash Pad: Tiny House Experience

9.6 out of 10, Exceptional, (18)
"Super cute, cozy, and quiet. The only thing I would think to change would be additional towels for guests. We would definitely book again when in the area. "
The price is AU$221
includes taxes & fees
6 July - 7 July
The Cozy Crash Pad: Tiny House Experience

East Orlando Getaway - 3BR/2BTH * Private Pool

9.2 out of 10, Wonderful, (22)
"House was in a nice neighborhood, beds were comfortable. Very clean. Would stay again. "
The price is AU$760
includes taxes & fees
28 June - 29 June
East Orlando Getaway - 3BR/2BTH * Private Pool

Tranquil 3-bedroom house in Sanford with AC, WiFi

9.8 out of 10, Exceptional, (14)
"Beautiful place to stay near the airport "
The price is AU$381
includes taxes & fees
30 June - 1 July
Tranquil 3-bedroom house in Sanford with AC, WiFi

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 AU$227
includes taxes & fees
7 July - 8 July
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Orlando Area Vacation Rental

9.6 out of 10, Exceptional, (41)
"The house is in a great area for visiting springs, the zoo, Mt. Dora, etc. we found it to be centrally located for all we wanted to do while in the area. The house could use a good scrub inside but it was clean enough to be comfortable. Overall a great spot. "
The price is AU$314
includes taxes & fees
15 July - 16 July
Orlando Area Vacation Rental

Upstay - Waterside Home With Pool and Hot Tub

2.0 star property
The price is AU$789
includes taxes & fees
2 July - 3 July
Upstay - Waterside Home With Pool and Hot Tub

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (1)
"Honestly the place is very clean, affordable, and is close to the theme parks! The location is safe and relaxing to just get away. Deanna is very accommodating to the needs of her guests that stay here! Thank you so much!"
The price is AU$195
includes taxes & fees
1 July - 2 July
Charming 2-bedroom Country Cottage in Kissimmee with private parking

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

10.0 out of 10, Exceptional, (27)
"Great property and host "
The price is AU$391
includes taxes & fees
3 July - 4 July
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

4 Bedrooms/2 Bathrooms AMAZING HOME! PRIVATE POOL!

9.6 out of 10, Exceptional, (14)
"The place was great for us. We came down for our son’s volleyball nationals and the pool and game room were great for down time."
The price is AU$837
includes taxes & fees
25 June - 26 June
4 Bedrooms/2 Bathrooms AMAZING HOME! PRIVATE POOL!

Florida Vacation with pool fun for families

9.6 out of 10, Exceptional, (28)
"The place is perfectly located and clean. Loved it "
The price is AU$556
includes taxes & fees
8 July - 9 July
Florida Vacation with pool fun for families
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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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 66 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.