Vacation Rentals in Winter Park, FL
PRICE PER NIGHT
ACCOMMODATION TYPES
Top-Rated Vacation Rentals in Winter Park, FL
Book a vacation rental in Winter Park that has the highest visitor rating. Here are 6 of the best vacation rentals in Winter Park.
Cozy Comfort Just 2 Blocks From Park Ave!
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 4
·
Pool · Hot Tub · Fitness Center ·
From
$185/nightProperty
House · 2 Beds · 1 bath
Amenities
Pool
Hot Tub
Fitness Center
Swimming Pool
Wifi
Furnished
Other spaces
Workspace
Amazing location- walk to everything
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 5
·
Kitchen · In Unit Laundry · Balcony ·
From
$359/nightProperty
Condo · 2 Beds · 2 baths
Amenities
In Unit Laundry
Residents Lounge
Fireplace
Fitness Center
Waterfront
Air Conditioning
Oven
Lake
Other spaces
Kitchen, Balcony, Workspace
Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
10
Excellent
·
Virginia Heights
·
3 br
·
Sleeps 6
·
Fireplace · Furnished · In Unit Laundry ·
From
$327/nightProperty
House · 3 Beds · 3 baths
Amenities
Fireplace
Furnished
In Unit Laundry
Dishwasher
Wifi
Swimming Pool
Private Pool
Pool
Other spaces
Workspace, Kitchen
Sunset Cove Luxury 2BR/2BA Condo Winter Park! FREE GARAGE, Wi-Fi
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 5
·
In Unit Laundry · Wifi · Dishwasher ·
From
$169/nightProperty
Condo · 2 Beds · 2 baths
Amenities
In Unit Laundry
Wifi
Dishwasher
Fitness Center
Air Conditioning
Oven
Swimming Pool
Free Parking
Other spaces
Balcony, Kitchen
A curated stay in the Historic College Quarter
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 4
·
Oven · Wifi · Air Conditioning ·
From
$219/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Oven
Wifi
Air Conditioning
Dishwasher
In Unit Laundry
Fitness Center
Furnished
Other spaces
Kitchen
GREAT LOCATION 🏡
10
Excellent
·
Winter Park
·
3 br
·
Sleeps 6
·
In Unit Laundry · Oven · Fitness Center ·
From
$180/nightProperty
House · 3 Beds · 3 baths
Amenities
In Unit Laundry
Oven
Fitness Center
Wifi
Hot Tub
Air Conditioning
Furnished
Dishwasher
Other spaces
Kitchen
Our Recommended Vacation Rentals in Winter Park, FL
We analyzed vacation rentals in Winter Park from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Winter Park to help you find a deal for your next trip.
Orlando Area Vacation Rental ~ 21 Mi to Disney!
No rating
·
Winter Park
·
2 br
·
Sleeps 4
·
Air Conditioning · Kitchen · On Site Laundry ·
From
$80/nightProperty
House · 2 Beds · 1 bath
Amenities
Air Conditioning
On Site Laundry
In Unit Laundry
Oven
Furnished
Wifi
Other spaces
Kitchen
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
No rating
·
Winter Park
·
3 br
·
Sleeps 8
·
Kitchen · In Unit Laundry · Private Pool ·
From
$320/nightProperty
House · 3 Beds · 2 baths
Amenities
In Unit Laundry
Private Pool
Dishwasher
Air Conditioning
Residents Lounge
Pool
Wifi
Swimming Pool
Other spaces
Kitchen, Workspace
Charming Winter Park Pool Home - Perfect Location
No rating
·
Winter Park
·
2 br
·
Sleeps 4
·
Business Center · Wifi · Furnished ·
From
$165/nightProperty
House · 2 Beds · 1 bath
Amenities
Business Center
Wifi
Furnished
Air Conditioning
Swimming Pool
In Unit Laundry
Budget-Friendly Vacation Rentals in Winter Park, FL
Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Winter Park starting at $77. Use the price filter at the top of the page to search for more specific prices.
Modern and Romantiv Villa
10
Excellent
·
Winter Park
·
1 br
·
Sleeps 3
·
Outdoor Space · Air Conditioning · Workspace ·
From
$77/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Wifi
Furnished
Other spaces
Workspace, Kitchen
Adorable 1 Bedroom in the perfect location!
No rating
·
Winter Park
·
1 br
·
Sleeps 2
·
Pool · In Unit Laundry · Wifi ·
From
$78/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Wifi
Furnished
Oven
Hot Tub
Dishwasher
Swimming Pool
Other spaces
Kitchen
Cozy Condo w/washer-dryer by Downtown,UCF, Full Sail Univ, Theme Parks, And MCO
No rating
·
Winter Park
·
1 br
·
Sleeps 3
·
Kitchen · Air Conditioning · Pool ·
From
$85/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Air Conditioning
Pool
In Unit Laundry
Swimming Pool
Furnished
Oven
Wifi
Other spaces
Kitchen
Adorable and espacious, 2 Beds, with great location
10
Excellent
·
Winter Park
·
2 br
·
Sleeps 6
·
In Unit Laundry · Air Conditioning · Furnished ·
From
$90/nightProperty
House · 2 Beds · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
Fitness Center
Other spaces
Kitchen
Perfect Private Winter Park Getaway Near Theme Parks!
No rating
·
Winter Park
·
1 br
·
Sleeps 2
·
Oven · Air Conditioning · On Site Laundry ·
From
$93/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Oven
Air Conditioning
On Site Laundry
Swimming Pool
Dishwasher
Pool
In Unit Laundry
Wifi
Other spaces
Kitchen
Family-Friendly Vacation Rentals in Winter Park, FL
Heading to Winter Park for your next family vacation? Check out these family-friendly vacation rentals, which have more bedrooms and more space for you and your loved ones. Use the filters at the top of the page to narrow your search and find what you need.
Cute and Cozy Apartment-B 1 Bedroom Duplex
No rating
·
Winter Park
·
1 br
·
Sleeps 2
·
Wifi · Furnished · Air Conditioning ·
From
$145/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Furnished
Air Conditioning
In Unit Laundry
Other spaces
Kitchen
Stylish Winter Park Flat: Minutes from Park Avenue
No rating
·
Winter Park
·
1 br
·
Sleeps 4
·
Furnished · In Unit Laundry · Free Parking ·
From
$99/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Furnished
In Unit Laundry
Free Parking
Pool
Wifi
Storage
Walk In Closets
Residents Lounge
Other spaces
Kitchen, Balcony
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations
No rating
·
Winter Park
·
1 br
·
Sleeps 6
·
Kitchen · Swimming Pool · Pool ·
From
$406/nightProperty
House · 1 Bed · 1 bath
Amenities
Swimming Pool
Pool
Fitness Center
In Unit Laundry
Fireplace
Wifi
Air Conditioning
Wheelchair Accessible
Other spaces
Kitchen, Balcony, Workspace
Expand your search criteria to see more vacation rentals near Winter Park.
Updated: December 1, 2023
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