Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Winter Park holiday rentals

Interior

Upstay 2BR Family Condo Ventura Golf Country Club

Upstay 2BR Family Condo Ventura Golf Country Club
3.0 star property
Ventura
The price is RM246
RM897 total
includes taxes & fees
1 Jun - 2 Jun
Upstay 2BR Family Condo Ventura Golf Country Club
Free WiFi

Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is RM321
RM657 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Modern Studio
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 RM284
RM971 total
includes taxes & fees
1 Jun - 2 Jun
Upstay 2BR Family Condo Ventura Golf Country Club
Lobby

Pinnacle Apartments W Amenties by Heavenly Homes

Pinnacle Apartments W Amenties by Heavenly Homes
4.0 star property
Orlando
The price is RM324
RM1,316 total
includes taxes & fees
7 Jun - 8 Jun
Pinnacle Apartments W Amenties by Heavenly Homes
Billiards

Riviere 2BR Apartment Pet Friendly Oasis Sleeps 6 Close to Epic Universe Pool & Gym

Riviere 2BR Apartment Pet Friendly Oasis Sleeps 6 Close to Epic Universe Pool & Gym
4.0 star property
International Drive District
The price is RM491
RM1,836 total
includes taxes & fees
4 Jun - 5 Jun
Riviere 2BR Apartment Pet Friendly Oasis Sleeps 6 Close to Epic Universe Pool & Gym
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, (5,620 reviews)
"Great stay enjoyed will stay again"
Canada
Zackary
The price is RM568
RM639 total
includes taxes & fees
24 Jun - 25 Jun
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 RM457
RM845 total
includes taxes & fees
1 Jun - 2 Jun
The Front Porch
Terrace/patio

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 RM375
RM1,525 total
includes taxes & fees
4 Jun - 5 Jun
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
Living area

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 RM278
RM876 total
includes taxes & fees
2 Jun - 3 Jun
The Blue Aztec
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 RM413
RM941 total
includes taxes & fees
4 Jun - 5 Jun
Riviere Apartments King Bed Suite & Pool & Gym & Pet Friendly & Near Epic Universe
Interior

Cozy 1BR Condo w Pool - Near Universal Studios

Cozy 1BR Condo w Pool - Near Universal Studios
3.0 star property
International Drive District
The price is RM266
RM651 total
includes taxes & fees
8 Jun - 9 Jun
Cozy 1BR Condo w Pool - Near Universal Studios
Room

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 RM327
RM1,632 total
includes taxes & fees
7 Jun - 8 Jun
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
2 bedrooms, Internet

Luxury House - Sleeps 8 Golf Disney Family Fun

Luxury House - Sleeps 8 Golf Disney Family Fun
2.0 star property
Ventura
The price is RM600
RM2,030 total
includes taxes & fees
4 Jun - 5 Jun
Luxury House - Sleeps 8 Golf Disney Family Fun
Exterior

The Contemporary

The Contemporary
3.0 star property
Sanford
The price is RM464
RM1,083 total
includes taxes & fees
2 Jun - 3 Jun
The Contemporary
Living area

Family 2-bedroom Suite in Prime Orlando Location

Family 2-bedroom Suite in Prime Orlando Location
3.5 star property
Florida Center
The price is RM454
RM1,246 total
includes taxes & fees
3 Jun - 4 Jun
Family 2-bedroom Suite in Prime Orlando Location
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, (4,404 reviews)
"Amazing stay!"
United States
Lilyanne
The price is RM591
RM665 total
includes taxes & fees
3 Jun - 4 Jun
Marriott's Grande Vista
Interior

Pool Access! Dog-friendly Retreat 16 Mi to Orlando

Pool Access! Dog-friendly Retreat 16 Mi to Orlando
3.0 star property
Longwood
Pool Access! Dog-friendly Retreat 16 Mi to Orlando
Living area

Boho Nights

Boho Nights
3.0 star property
Sanford
9.6 out of 10, Exceptional, (15 reviews)
"Great location very clean awesome decor "
United States
Heather
The price is RM285
RM586 total
includes taxes & fees
5 Jun - 6 Jun
Boho Nights
Lobby

Boulder Ridge Villas at Disney's Wilderness Lodge

Boulder Ridge Villas at Disney's Wilderness Lodge
4.0 star property
Bay Lake
8.8 out of 10, Excellent, (54 reviews)
"Looking for perfect compliment to your ultimate Disney World experience? Look no further than the Wilderness Lodge Villas. Not only are the rooms cozy and comfortable but the rustic atmosphere is spot on. After a long day at the Magic Kingdom, there is no better experience than taking the boat back to the lodge, especially at night. You can either recharge your batteries and go back, or you can enjoy all the amenities and atmosphere of the lodge. The only negative was that the food selection at...
United States
David O.
Boulder Ridge Villas at Disney's Wilderness Lodge
Interior

Upstay 2BR Golfer's Retreat w Patio Ventura Resort

Upstay 2BR Golfer's Retreat w Patio Ventura Resort
3.0 star property
Ventura
The price is RM262
RM870 total
includes taxes & fees
1 Jun - 2 Jun
Upstay 2BR Golfer's Retreat w Patio Ventura Resort
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

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

8/10 Good
"The staff was wonderful. My room was ok, very clean. The pool area was excellent. The bathroom was sort of small and the shower curtain was too short, so the floor got soaked each time I showered. I loved the location and walkability to various things. Overall, it was quite comfortable for me, a solo traveler. I will use them for my next trip. But, please, get new shower curtains."
Kimberley 2-night trip
Posted 1 hour ago
Wyndham I-Drive Avanti Resort & Conference Center

Find out more about Winter Park

Search for holiday rentals in Winter Park on Expedia.co.uk! 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 54 holiday rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Rollins Museum of Art and Morse Museum of American Art, whereas Lake Virginia and Mead Garden 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.