A two-story house with a balcony, surrounded by lush greenery and trees.

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Winter Park holiday rentals

3 bedrooms, Internet

Walk to Epic Universe and Occc From This Condo

Walk to Epic Universe and Occc From This Condo
2.0 star property
Orlando
The price is ฿5,883
฿11,092 total
includes taxes & fees
3 Aug - 4 Aug
Walk to Epic Universe and Occc From This Condo
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is ฿2,277
฿7,285 total
includes taxes & fees
13 Jul - 14 Jul
The Blue Aztec
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
The price is ฿2,547
฿5,090 total
includes taxes & fees
15 Jul - 16 Jul
Boho Nights
2 bedrooms, desk, free WiFi

The Front Porch

The Front Porch
3.0 star property
Downtown Sanford
9.2 out of 10, Wonderful, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The price is ฿4,195
฿7,495 total
includes taxes & fees
13 Jul - 14 Jul
The Front Porch
Interior

Totally 80's

Totally 80's
3.0 star property
Sanford
8.6 out of 10, Excellent, (11 reviews)
"Great location to downtown Sanford!"
United States
Kathleen
The price is ฿2,247
฿4,754 total
includes taxes & fees
13 Jul - 14 Jul
Totally 80's
Lobby

Pinnacle Apartments W Amenties by Heavenly Homes

Pinnacle Apartments W Amenties by Heavenly Homes
4.0 star property
Orlando
The price is ฿3,121
฿11,502 total
includes taxes & fees
6 Aug - 7 Aug
Pinnacle Apartments W Amenties by Heavenly Homes
Apartment (2 Bedrooms) | Interior

Upstay Golfer's Retreat w Patio at Ventura Resort

Upstay Golfer's Retreat w Patio at Ventura Resort
3.0 star property
Ventura
The price is ฿2,896
฿8,090 total
includes taxes & fees
5 Aug - 6 Aug
Upstay Golfer's Retreat w Patio at Ventura Resort
Exterior

The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (9 reviews)
"Location, location, location!!! What a cute and fun space. I thoroughly enjoyed my entire Jazz Loft experience. Look fwd to next trip! "
United States
Deborah
The price is ฿2,397
฿4,922 total
includes taxes & fees
14 Jul - 15 Jul
The Jazz Loft
Interior

Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (18 reviews)
"Great location for restaurants and river trail. Very well stocked so it is an easy and comfortable stay."
United States
Nancy
The price is ฿2,547
฿5,090 total
includes taxes & fees
27 Jul - 28 Jul
Bella Breeze
Studio | Free WiFi

Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is ฿2,697
฿5,517 total
includes taxes & fees
13 Jul - 14 Jul
Cozy Modern Studio
3 bedrooms, Internet

Lrg Condo w Scenic Patio Views - Next to Occc

Lrg Condo w Scenic Patio Views - Next to Occc
2.0 star property
Orlando
The price is ฿7,375
฿12,584 total
includes taxes & fees
13 Jul - 14 Jul
Lrg Condo w Scenic Patio Views - Next to Occc
6 outdoor pools, free pool cabanas, pool umbrellas

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
Orlando
9.2 out of 10, Wonderful, (6,082 reviews)
"Very happy with our stay."
United States
Jessica
The price is ฿5,627
฿6,330 total
includes taxes & fees
15 Jul - 16 Jul
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Apartment, Patio | Living area

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
The price is ฿3,845
฿9,944 total
includes taxes & fees
20 Jul - 21 Jul
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
2 outdoor pools, open 7:00 AM to 11:00 PM, free pool cabanas

Magical Moment Vacation Condos

Magical Moment Vacation Condos
4.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"Very Clean room staff were great !! Definitely would stay again !"
United States
stephanie
The price is ฿4,075
฿13,353 total
includes taxes & fees
11 Aug - 12 Aug
Magical Moment Vacation Condos
Exterior

The Contemporary

The Contemporary
3.0 star property
Downtown Sanford
The price is ฿3,895
฿9,097 total
includes taxes & fees
13 Jul - 14 Jul
The Contemporary
2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, pool loungers

Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (174 reviews)
"I've stayed here before and it is very good for the price you get! Staff was lovely and the room was amazing."
United States
Jarelieze
The price is ฿2,747
฿3,417 total
includes taxes & fees
14 Jul - 15 Jul
Villas at Fortune Place
Apartment (2 Bedrooms) | Interior

Upstay: Family-friendly Getaway With Spa & Pool

Upstay: Family-friendly Getaway With Spa & Pool
3.5 star property
Orlando
10.0 out of 10, Exceptional, (1 review)
"Clean room"
United States
Yves marie
The price is ฿4,062
฿9,401 total
includes taxes & fees
10 Aug - 11 Aug
Upstay: Family-friendly Getaway With Spa & Pool
Apartment, Patio | Private kitchen | Coffee/tea maker

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
4.0 star property
Downtown Orlando
The price is ฿3,028
฿12,670 total
includes taxes & fees
20 Jul - 21 Jul
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
Studio | Living area

Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning

Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
3.5 star property
Colonialtown South
The price is ฿8,094
฿14,106 total
includes taxes & fees
14 Jul - 15 Jul
Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
Interior

Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens

Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens
4.0 star property
International Drive District
The price is ฿5,687
฿12,390 total
includes taxes & fees
5 Aug - 6 Aug
Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens
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

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"So clean, I really enjoyed my stay!!"
Krystile 1-night trip
Posted 5 hours ago
Hyatt Regency Orlando International Airport

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 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.

How many holiday rentals are there in Winter Park?

Expedia has 53 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. Kia Center and Universal Studios Florida 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.