Vacation Rentals in Winter Park, FL
PRICE PER NIGHT
ACCOMMODATION TYPES
You're Pampered Here - Just 3 Blocks From Park Avenue!
No reviews
·
Winter Park
·
3 br
·
Sleeps 6
·
Ev Charging · Hot Tub · High Ceilings ·
From
$226/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Ev Charging
Hot Tub
High Ceilings
Hardwood Floor
Fitness Center
Pool
Dishwasher
Oven
Other spaces
Balcony, Workspace, Kitchen
Just Like Home... With A Pool!
9.4
Excellent
·
Winter Park
·
3 br
·
Sleeps 6
·
On Site Laundry · High Ceilings · Private Pool ·
From
$160/nightProperty
House · 3 Beds · 2 baths
Amenities
On Site Laundry
High Ceilings
Private Pool
Fireplace
Fitness Center
Pool
Dishwasher
Oven
Other spaces
Kitchen
Beautiful Boho Brand New Winter Park Home!
9.7
Excellent
·
Winter Park
·
3 br
·
Sleeps 6
·
High Ceilings · Outdoor Space · Fitness Center ·
From
$397/nightProperty
House · 3 Beds · 3 baths
Amenities
High Ceilings
Fitness Center
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Workspace, Kitchen
A curated stay in the Historic College Quarter - 30 days minimum stay -
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 4
·
Outdoor Space · Fitness Center · Dishwasher ·
From
$262/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Fitness Center
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Kitchen
Three Blocks to Park Ave, 2 Blocks to WP Village!!!
9
Excellent
·
Winter Park
·
2 br
·
Sleeps 4
·
Ev Charging · Outdoor Space · Workspace ·
From
$125/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Ev Charging
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Workspace, Kitchen
Stroll to Park Avenue from Vintage Lake-View House
9.5
Excellent
·
Virginia Heights
·
2 br
·
Sleeps 6
·
On Site Laundry · Lake · Waterfront ·
From
$188/nightProperty
House · 2 Beds · 2 baths
Amenities
On Site Laundry
Lake
Waterfront
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Other spaces
Workspace, Kitchen
Walk The Downtown Village of Winter Park!!!
No reviews
·
Winter Park
·
2 br
·
Sleeps 4
·
High Ceilings · Lake · Waterfront ·
From
$131/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
High Ceilings
Lake
Waterfront
Hardwood Floor
Fitness Center
Pool
Dishwasher
Oven
Other spaces
Workspace, Kitchen
3 BR Getaway w/ Private Pool near Full Sail University
No reviews
·
Winter Park
·
3 br
·
Sleeps 10
·
Smoking Allowed · Private Pool · Pool ·
From
$168/nightProperty
House · 3 Beds · 2 baths
Amenities
Smoking Allowed
Private Pool
Pool
Dishwasher
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Kitchen
The best of Zumper, delivered
Be the first to hear about new listings matching your search.
Cozy Comfort In The Heart of Winter Park!
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 4
·
Hot Tub · High Ceilings · Assigned Parking ·
From
$125/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Hot Tub
High Ceilings
Assigned Parking
Hardwood Floor
Pool
Dishwasher
Oven
In Unit Laundry
Other spaces
Workspace, Kitchen
Winter Park charm. Close to Park Ave
9.7
Excellent
·
Winter Park
·
2 br
·
Sleeps 4
·
Workspace · In Unit Laundry · Air Conditioning ·
From
$150/nightProperty
House · 2 Beds · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Workspace
Pondside Retreat with Koi in Charming Winter Park, FL
No reviews
·
Winter Park
·
4 br
·
Sleeps 6
·
Air Conditioning · Wifi · Furnished ·
From
$195/nightProperty
House · 4 Beds · 2 baths
Amenities
Air Conditioning
Wifi
Furnished
Mid Century Luxury, 1 block from Park Ave (#2)
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 5
·
Outdoor Space · Dishwasher · Oven ·
From
$140/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Cheerful and stylish 2-bedroom with parking, centrally located
No reviews
·
Winter Park
·
2 br
·
Outdoor Space · Dishwasher · Kitchen ·
From
$138/nightProperty
House · 2 Beds · 1 bath
Amenities
Dishwasher
In Unit Laundry
Air Conditioning
Wifi
Furnished
Garage Parking
Other spaces
Kitchen
Casa Winter Park
9.8
Excellent
·
Winter Park
·
4 br
·
Sleeps 8
·
Assigned Parking · Private Pool · Fireplace ·
From
$374/nightProperty
House · 4 Beds · 4 baths
Amenities
Assigned Parking
Private Pool
Fireplace
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
Winter Park Getaway
10
Excellent
·
Winter Park
·
1 br
·
Sleeps 4
·
Oven · Kitchen · In Unit Laundry ·
From
$100/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Kitchen
Modern and Romantiv Villa
10
Excellent
·
Winter Park
·
1 br
·
Sleeps 3
·
Workspace · Kitchen · Air Conditioning ·
From
$77/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Wifi
Furnished
Other spaces
Workspace, Kitchen
Coastal Feel - Modern Appeal
No reviews
·
Winter Park
·
2 br
·
Sleeps 4
·
Fitness Center · Workspace · Pool ·
From
$160/nightProperty
House · 2 Beds · 2 baths
Amenities
Fitness Center
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Workspace, Kitchen
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths
No reviews
·
Winter Park
·
2 br
·
Sleeps 4
·
Hot Tub · Assigned Parking · Hardwood Floor ·
From
$156/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Hot Tub
Assigned Parking
Hardwood Floor
Fitness Center
Pool
Dishwasher
Oven
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Luxury Villa, 3bed/2bath Great Location with Pool
10
Excellent
·
Winter Park
·
3 br
·
Sleeps 9
·
Private Pool · Pool · Dishwasher ·
From
$139/nightProperty
House · 3 Beds · 2 baths
Amenities
Private Pool
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Kitchen
Cute bungalow minutes walk from Park Avenue.
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 4
·
Lake · Waterfront · Hardwood Floor ·
From
$200/nightProperty
House · 2 Beds · 2 baths
Amenities
Lake
Waterfront
Hardwood Floor
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
Cheerful 4-bedroom with large and lush backyard
8
Very good
·
Winter Park
·
4 br
·
Sleeps 8
·
Workspace · Dishwasher · Oven ·
From
$200/nightProperty
House · 4 Beds · 3 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Workspace, Kitchen
Peaceful Retreat #1 -2B /2B Apartment
No reviews
·
Winter Park
·
2 br
·
Sleeps 8
·
Kitchen · In Unit Laundry · Air Conditioning ·
From
$190/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Kitchen
Tranquil & Tiny house
10
Excellent
·
Winter Park
·
1 br
·
Sleeps 3
·
Assigned Parking · In Unit Laundry · Air Conditioning ·
From
$135/nightProperty
House · 1 Bed · 1 bath
Amenities
Assigned Parking
In Unit Laundry
Air Conditioning
Wifi
Furnished
Cute and Cozy Apartment-B 1 Bedroom Duplex
No reviews
·
Winter Park
·
1 br
·
Sleeps 2
·
In Unit Laundry · Air Conditioning · Wifi ·
From
$132/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Wifi
Furnished
Hidden Oasis #4 2 BDRM, 2 Bath
No reviews
·
Winter Park
·
2 br
·
Sleeps 8
·
Kitchen · In Unit Laundry · Air Conditioning ·
From
$190/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Kitchen
Total Serenity #2, 2 BDRM, 2 Bath
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 8
·
Kitchen · In Unit Laundry · Air Conditioning ·
From
$190/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Kitchen
Peace and the Park #3 -2 BDRM, 2 Bath
No reviews
·
Winter Park
·
2 br
·
Sleeps 4
·
Kitchen · In Unit Laundry · Air Conditioning ·
From
$190/nightProperty
House · 2 Beds · 2 baths
Amenities
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Kitchen
Winter Park Oasis
No reviews
·
Winter Park
·
2 br
·
Sleeps 8
·
Fireplace · Oven · Kitchen ·
From
$175/nightProperty
House · 2 Beds · 1 bath
Amenities
Fireplace
Oven
Air Conditioning
Wifi
Furnished
Other spaces
Kitchen
Mid Century Modern Cottage in The Heart of Winter Park
9.7
Excellent
·
Winter Park
·
2 br
·
Sleeps 5
·
Central Heat · Ski In Ski Out · Hot Tub ·
From
$120/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Central Heat
Ski In Ski Out
Hot Tub
Fitness Center
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
Best Home by Winter Park Hospital, Rollins College and Park Ave !!
10
Excellent
·
Winter Park
·
4 br
·
Sleeps 12
·
Fitness Center · Workspace · Dishwasher ·
From
$277/nightProperty
House · 4 Beds · 3 baths
Amenities
Fitness Center
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Garage Parking
Other spaces
Workspace, Kitchen
Hidden Historic Jewel In Downtown Location!
No reviews
·
Winter Park
·
2 br
·
Sleeps 4
·
Hardwood Floor · Fireplace · Outdoor Space ·
From
$179/nightProperty
House · 2 Beds · 2 baths
Amenities
Hardwood Floor
Fireplace
Fitness Center
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Other spaces
Kitchen
Chic Lakeside Midcentury Modern Retreat
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 4
·
On Site Laundry · Balcony · Outdoor Space ·
From
$116/nightProperty
Condo · 2 Beds · 1 bath
Amenities
On Site Laundry
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Balcony, Kitchen
Modern 2 Bedroom Apartment
No reviews
·
Winter Park
·
2 br
·
Sleeps 6
·
Smoking Allowed · Pool · Air Conditioning ·
From
$200/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Smoking Allowed
Pool
Air Conditioning
Wifi
Furnished
Swimming Pool
Winter Park Hideaway
No reviews
·
Winter Park
·
2 br
·
Sleeps 4
·
Kitchen · In Unit Laundry · Air Conditioning ·
From
$130/nightProperty
House · 2 Beds · 2 baths
Amenities
In Unit Laundry
Air Conditioning
Wifi
Furnished
Other spaces
Kitchen
Cozy Condo w/washer-dryer by Downtown,UCF, Full Sail Univ, Theme Parks, And MCO
No reviews
·
Winter Park
·
1 br
·
Sleeps 3
·
Pool · Oven · Kitchen ·
From
$85/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Pool
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Swimming Pool
Other spaces
Kitchen
Greatest location! Condo with private yard!
No reviews
·
Winter Park
·
2 br
·
Sleeps 4
·
Assigned Parking · Outdoor Space · Workspace ·
From
$300/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Assigned Parking
Dishwasher
Oven
In Unit Laundry
Wifi
Furnished
Other spaces
Workspace, Kitchen
Ideal Location, Charming Home, Spacious w/ a Full Lap Pool!
9.8
Excellent
·
Winter Park
·
4 br
·
Sleeps 10
·
Outdoor Space · Workspace · Pool ·
From
$384/nightProperty
House · 4 Beds · 2 baths
Amenities
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Swimming Pool
Other spaces
Workspace, Kitchen
Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins College
No reviews
·
Winter Park
·
1 br
·
Balcony · Fireplace · Fitness Center ·
From
$480/nightProperty
House · 1 Bed · 1 bath
Amenities
Fireplace
Fitness Center
Pool
In Unit Laundry
Air Conditioning
Wifi
Furnished
Swimming Pool
Other spaces
Balcony, Workspace, Kitchen
Private Balcony - Award Winning Accommodations w/Rooftop Pool, Close to Parks!
No reviews
·
Winter Park
·
1 br
·
Balcony · Fireplace · Fitness Center ·
From
$380/nightProperty
House · 1 Bed · 1 bath
Amenities
Fireplace
Fitness Center
Pool
In Unit Laundry
Air Conditioning
Wifi
Furnished
Swimming Pool
Other spaces
Balcony, Workspace, Kitchen
Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool
No reviews
·
Winter Park
·
1 br
·
Fireplace · Fitness Center · Workspace ·
From
$372/nightProperty
House · 1 Bed · 1 bath
Amenities
Fireplace
Fitness Center
Pool
In Unit Laundry
Air Conditioning
Wifi
Furnished
Swimming Pool
Other spaces
Workspace, Kitchen
Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College
No reviews
·
Winter Park
·
1 br
·
Balcony · Fireplace · Fitness Center ·
From
$418/nightProperty
House · 1 Bed · 1 bath
Amenities
Fireplace
Fitness Center
Pool
In Unit Laundry
Air Conditioning
Wifi
Furnished
Swimming Pool
Other spaces
Balcony, Workspace, Kitchen
ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks
No reviews
·
Winter Park
·
1 br
·
Balcony · Fireplace · Fitness Center ·
From
$384/nightProperty
House · 1 Bed · 1 bath
Amenities
Fireplace
Fitness Center
Pool
In Unit Laundry
Air Conditioning
Wifi
Furnished
Wheelchair Accessible
Other spaces
Balcony, Workspace, Kitchen
Contemporary Award Winning Hotel w/Rooftop Close to Parks & Rollins College
No reviews
·
Winter Park
·
1 br
·
Balcony · Fireplace · Fitness Center ·
From
$381/nightProperty
House · 1 Bed · 1 bath
Amenities
Fireplace
Fitness Center
Pool
In Unit Laundry
Air Conditioning
Wifi
Furnished
Swimming Pool
Other spaces
Balcony, Workspace, Kitchen
ADA Compliant Room in Award Winning Hotel w/Rooftop Pool - Close to Parks!
No reviews
·
Winter Park
·
1 br
·
Balcony · Fireplace · Fitness Center ·
From
$445/nightProperty
House · 1 Bed · 1 bath
Amenities
Fireplace
Fitness Center
Pool
In Unit Laundry
Air Conditioning
Wifi
Furnished
Wheelchair Accessible
Other spaces
Balcony, Workspace, Kitchen
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations
No reviews
·
Winter Park
·
1 br
·
Balcony · Fireplace · Fitness Center ·
From
$444/nightProperty
House · 1 Bed · 1 bath
Amenities
Fireplace
Fitness Center
Pool
In Unit Laundry
Air Conditioning
Wifi
Furnished
Wheelchair Accessible
Other spaces
Balcony, Workspace, Kitchen
TREDY FLAT IN WINTER PARK
No reviews
·
Winter Park
·
1 br
·
Sleeps 4
·
Balcony · Pool · Dishwasher ·
From
$119/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Swimming Pool
Other spaces
Balcony, Kitchen
Beautiful Peaceful fenced yard home !
10
Excellent
·
Winter Park
·
3 br
·
Sleeps 10
·
Lake · Waterfront · Fitness Center ·
From
$270/nightProperty
House · 3 Beds · 2 baths
Amenities
Lake
Waterfront
Fitness Center
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Other spaces
Workspace, Kitchen
Spacious Lovely 2-bedroom vacation home with pool
No reviews
·
Winter Park
·
3 br
·
Sleeps 6
·
Dishwasher · Oven · Kitchen ·
From
$135/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Furnished
Swimming Pool
Other spaces
Kitchen
Cozy 1/1 Unit w/ Balcony
No reviews
·
Winter Park
·
1 br
·
Sleeps 4
·
On Site Laundry · Private Pool · Balcony ·
From
$120/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Private Pool
Pool
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Other spaces
Balcony, Kitchen
Winter Park Central ! luxurious, convenient, free covered parking!
10
Excellent
·
Winter Park
·
1 br
·
Free Parking · Lake · Waterfront ·
From
$181/nightProperty
Condo · 1 Bed · 2 baths
Amenities
Free Parking
Lake
Waterfront
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Wifi
Other spaces
Balcony, Kitchen
Showing 1 - 50 of 52 results
Updated: March 27, 2023
Learn about vacation rentals in
Winter Park
Explore 54 vacation rentals near Winter Park, Florida. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Winter Park, you can see photos of Winter Park vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Winter Park vacation rentals in specific areas. Whether you’re looking for a Winter Park staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Winter Park is $77 per night and the highest price is $480 per night.
21 of the vacation rentals near Winter Park are
apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation
units is $137 per night. There are
currently 10 vacation units under this
price. 29 of the vacation rentals near Winter Park are houses.
The average bathroom count for a vacation house near Winter Park is
2. The average price for vacation houses near Winter Park is $268 per night. There are 15 vacation homes under this price. The most common
amenities for vacation rentals near Winter Park are: furnished, wifi, and air conditioning. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
17 available
2 bed rentals
23 available
3 bed rentals
9 available
4+ bed rentals
5 available
Getting around Winter Park
Walking
6/10
Some shops and stores are within a few minutes.
Car
8/10
Commuting is easy with multiple accessible routes and plenty of parking.
Transit
3/10
There are a few mass transit options within the area.
Points of interest in Winter Park
Groceries
6/10
At least one grocery store within a 15-minute walk
Shopping
6/10
Variety of shops within walking distance
Cafes
4/10
Some cafés within walking distance
Restaurants
6/10
Some restaurants within walking distance
Parks
6/10
Moderate amount of park space nearby
Nightlife
3/10
Few or no bars within walking distance
Vacation Rentals in Winter Park, FL FAQ
How many vacation rentals in Winter Park are available?
There are currently 54 vacation rentals in Winter Park available. Our vacation rentals in Winter Park include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Winter Park?
Yes, right now there are 27 pet friendly vacation rentals in Winter Park. A pet friendly vacation rental in Winter Park means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Winter Park with a pool?
Yes there are vacation rentals with a pool available in Winter Park, FL. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Winter Park with internet access?
As of March 27, 2023, there are vacation rentals with internet access available in Winter Park, Florida. Check out more enjoyable destinations on Vacations by Zumper.
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