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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Winter Park holiday rentals

Studio | Free WiFi

Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is ฿2,883
฿5,472 total
includes taxes & fees
16 Apr - 17 Apr
Cozy Modern Studio
Apartment, Accessible | 2 bedrooms, Internet

Free Breakfast Parking 2B Disney Resort Condo

Free Breakfast Parking 2B Disney Resort Condo
2.0 star property
International Drive District
The price is ฿3,840
฿9,996 total
includes taxes & fees
20 Apr - 21 Apr
Free Breakfast Parking 2B Disney Resort Condo
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 ฿4,665
฿16,140 total
includes taxes & fees
12 May - 13 May
Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens
Pool

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 ฿2,086
฿11,261 total
includes taxes & fees
14 Apr - 15 Apr
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
Exterior

The Contemporary

The Contemporary
3.0 star property
Sanford
The price is ฿3,748
฿8,754 total
includes taxes & fees
15 Apr - 16 Apr
The Contemporary
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, (5,154 reviews)
"The best place to stay "
United States
Rosario
The price is ฿4,934
฿5,550 total
includes taxes & fees
4 May - 5 May
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Lobby

Pinnacle Apartments W Amenties by Heavenly Homes

Pinnacle Apartments W Amenties by Heavenly Homes
4.0 star property
Orlando
The price is ฿2,489
฿10,489 total
includes taxes & fees
15 Apr - 16 Apr
Pinnacle Apartments W Amenties by Heavenly Homes
Interior

Vacational Apartment at Orlando 3608

Vacational Apartment at Orlando 3608
2.0 star property
Ventura
The price is ฿3,700
฿6,245 total
includes taxes & fees
5 May - 6 May
Vacational Apartment at Orlando 3608
Apartment (2 Bedrooms) | Front of property

Poolside Bliss & Theme Park Thrills: Orlando Oasis

Poolside Bliss & Theme Park Thrills: Orlando Oasis
3.5 star property
International Drive District
The price is ฿2,563
฿12,583 total
includes taxes & fees
21 Apr - 22 Apr
Poolside Bliss & Theme Park Thrills: Orlando Oasis
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is ฿2,393
฿7,236 total
includes taxes & fees
4 May - 5 May
The Blue Aztec
2 bedrooms, desk, free WiFi

The Front Porch

The Front Porch
3.0 star property
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 ฿3,748
฿6,889 total
includes taxes & fees
14 Apr - 15 Apr
The Front Porch
Apartment | 2 bedrooms, Internet

Upstay 2BR Family Condo Ventura Golf Country Club

Upstay 2BR Family Condo Ventura Golf Country Club
2.0 star property
Ventura
The price is ฿2,771
฿8,378 total
includes taxes & fees
14 Apr - 15 Apr
Upstay 2BR Family Condo Ventura Golf Country Club
Billiards

Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe

Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe
4.0 star property
International Drive District
The price is ฿3,511
฿7,795 total
includes taxes & fees
12 May - 13 May
Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe
Pool

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 ฿2,086
฿12,558 total
includes taxes & fees
14 Apr - 15 Apr
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
Front of property

Apartment 1 BR Free Shuttle to Disney Parks

Apartment 1 BR Free Shuttle to Disney Parks
3.5 star property
Orlando
The price is ฿3,140
฿8,938 total
includes taxes & fees
14 Apr - 15 Apr
Apartment 1 BR Free Shuttle to Disney Parks
4 outdoor pools, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)

Marriott's Grande Vista

Marriott's Grande Vista
4.0 star property
Orlando
9.0 out of 10, Wonderful, (4,154 reviews)
"Great place to stay"
United States
Candise
The price is ฿4,453
฿5,010 total
includes taxes & fees
26 Apr - 27 Apr
Marriott's Grande Vista
Condo, 2 Bedrooms | Exterior

Edgewater Escape At Storey Lake By Shine Villas 2 Bedroom Apts

Edgewater Escape At Storey Lake By Shine Villas 2 Bedroom Apts
3.0 star property
Kissimmee
The price is ฿4,820
฿18,388 total
includes taxes & fees
18 Apr - 19 Apr
Edgewater Escape At Storey Lake By Shine Villas 2 Bedroom Apts
Standard Apartment | Living area

The Mellow Yellow

The Mellow Yellow
3.0 star property
Sanford
6.0 out of 10, (3 reviews)
"Owners had over booked this property, but proactively reached out and moved me to like property, BoHo Nights. Very nice place. Easy walk to downtown Sanford. Coffee options provided were appreciated."
United States
Gary
The price is ฿2,451
฿7,301 total
includes taxes & fees
14 Apr - 15 Apr
The Mellow Yellow
House (2 Bedrooms) | Interior

Deltona Lake House, Day Trip to Disney & Universal

Deltona Lake House, Day Trip to Disney & Universal
3.0 star property
Deltona Lakes
10.0 out of 10, Exceptional, (3 reviews)
"This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!"
United States
Anonymous traveller
The price is ฿6,824
฿13,629 total
includes taxes & fees
19 Apr - 20 Apr
Deltona Lake House, Day Trip to Disney & Universal
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

Boho Nights

Boho Nights
3.0 star property
Sanford
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
The price is ฿2,307
฿4,736 total
includes taxes & fees
16 Apr - 17 Apr
Boho Nights
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"The pool, bowling alley & arcade were great! Loved having a Starbucks on site. They had a hard time keeping the soda machines stocked but the food was good overall. The tacos at the Atomic Grill were great. It was a nice place to stay and would stay again when we go to Universal."
Jennifer Ann 7-night trip
Posted 1 hour ago
Universal's Cabana Bay Beach Resort

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 49 holiday rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Morse Museum of American Art and Casa Feliz Historic Home Museum, 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.