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

Winter Park Vacation Rentals

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Check prices for these dates

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

Our top choices for Winter Park vacation 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 ￥30,735
￥56,108 total
includes taxes & fees
Aug 4 - Aug 5
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 ￥11,910
￥36,402 total
includes taxes & fees
Jul 10 - Jul 11
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 ￥12,406
￥24,794 total
includes taxes & fees
Jul 26 - Jul 27
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 ￥20,025
￥36,052 total
includes taxes & fees
Jul 28 - Jul 29
The Front Porch
Interior

Totally 80's

Totally 80's
3.0 star property
Sanford
8.4 out of 10, Very Good, (10 reviews)
"Great location to downtown Sanford!"
United States
Kathleen
The price is ￥10,116
￥22,229 total
includes taxes & fees
Jul 12 - Jul 13
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 ￥14,718
￥55,481 total
includes taxes & fees
Jul 14 - Jul 15
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 ￥12,680
￥37,858 total
includes taxes & fees
Jul 12 - Jul 13
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 ￥11,677
￥23,978 total
includes taxes & fees
Jul 31 - Aug 1
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 ￥12,096
￥24,447 total
includes taxes & fees
Jul 21 - Jul 22
Bella Breeze
Studio | Free WiFi

Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is ￥12,676
￥26,361 total
includes taxes & fees
Jul 25 - Jul 26
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 ￥36,013
￥61,447 total
includes taxes & fees
Jul 21 - Jul 22
Lrg Condo w Scenic Patio Views - Next to Occc
6 outdoor pools, free 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, (6,049 reviews)
"Have stayed there before. Great location for families with a pool for each area of the resort."
United States
Debra
The price is ￥27,474
￥30,909 total
includes taxes & fees
Jul 14 - Jul 15
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 ￥16,542
￥45,979 total
includes taxes & fees
Jul 14 - Jul 15
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
2 outdoor pools, open 7:00 AM to 11:00 PM, free cabanas, pool umbrellas

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 ￥17,369
￥57,555 total
includes taxes & fees
Jul 12 - Jul 13
Magical Moment Vacation Condos
Exterior

The Contemporary

The Contemporary
3.0 star property
Downtown Sanford
The price is ￥18,595
￥43,890 total
includes taxes & fees
Jul 13 - Jul 14
The Contemporary
2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (173 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 ￥13,380
￥16,647 total
includes taxes & fees
Jul 12 - Jul 13
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 ￥17,340
￥43,044 total
includes taxes & fees
Jul 12 - Jul 13
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 ￥19,826
￥67,431 total
includes taxes & fees
Jul 20 - Jul 21
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 ￥35,880
￥63,567 total
includes taxes & fees
Jul 14 - Jul 15
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 ￥29,140
￥62,047 total
includes taxes & fees
Jul 15 - Jul 16
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Our experience was amazing! The property was beautiful and clean and the rooms were also. The friendliness and helpfulness of the staff was top tier and definitely a determining factor as my family and I choosing to stay at this hotel in the future. The pool and other amenities were also cool. We will be back!"
Keisha 1-night trip
Posted less than an 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
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  • 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?

Grand Luxury Lakes 3BR Townhouse near Disney: Visitors like this Winter Park vacation home rental. It is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms and a kitchen with a dishwasher.

How many vacation rentals are there in Winter Park?

Expedia has 53 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Albin Polasek Museum and Sculpture Gardens and Morse Museum of American Art, whereas Lake Virginia and Kraft Azalea Gardens 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 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.