Vacation Rentals in Winter Park, FL

19 rentals

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.
Walk In With Tooth Brush In Your Pocket In This Beautiful Naples Apartment
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 6
·
On Site Laundry · Residents Lounge · Outdoor Space ·
From
$115/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
On Site Laundry
Residents Lounge
Wifi
Swimming Pool
Air Conditioning
Furnished
Pool
Dishwasher
Other spaces
Workspace, Balcony, Kitchen
"TOMMY BAHAMAS CONDO"
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 2
·
Mountains · Outdoor Space · Furnished ·
From
$166/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Mountains
Furnished
Elevator
Wifi
Pool
In Unit Laundry
Dishwasher
Residents Lounge
Other spaces
Outdoor Space, Kitchen
Luxurious 2 bedroom condo with lavish pool
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Furnished · Residents Lounge · Kitchen ·
From
$116/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Furnished
Residents Lounge
Pool
In Unit Laundry
Swimming Pool
Air Conditioning
Oven
Wifi
Other spaces
Kitchen, Outdoor Space
Best of the Best Summer 2024 Sale!!
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 6
·
Beach · Furnished · Oven ·
From
$68/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Beach
Furnished
Oven
Waterfront
Wifi
Air Conditioning
In Unit Laundry
Dishwasher
Other spaces
Outdoor Space, Kitchen
Quiet lovely 2-bed/bath condo in central Naples!
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 5
·
Dishwasher · Pool · Outdoor Space ·
From
$70/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Dishwasher
Pool
Oven
Beach
Swimming Pool
Residents Lounge
Air Conditioning
In Unit Laundry
Other spaces
Workspace, Balcony, Kitchen
Lush Villa in golfing community close to Beaches and Shopping. 2 Golf Courses,
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Pool · Oven · Air Conditioning ·
From
$116/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Pool
Oven
Air Conditioning
In Unit Laundry
Furnished
Residents Lounge
Wifi
Swimming Pool
Other spaces
Kitchen, Outdoor Space

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.
Low Rise (1-3) - NAPLES, FL

No rating

·
Winter Park
·
2 br
·
Swimming Pool · Dishwasher · In Unit Laundry ·
From
$158/night
Min stay: 365 nights
Property
Condo · 2 Beds · 2 baths
Amenities
Swimming Pool
Dishwasher
In Unit Laundry
Ceiling Fan
Air Conditioning
Assigned Parking
Low Rise (1-3) - NAPLES, FL

No rating

·
Winter Park
·
2 br
·
Air Conditioning · In Unit Laundry · Dishwasher ·
From
$113/night
Min stay: 365 nights
Property
Condo · 2 Beds · 2 baths
Amenities
Air Conditioning
In Unit Laundry
Dishwasher
Ceiling Fan
Low Rise (1-3) - NAPLES, FL

No rating

·
Winter Park
·
2 br
·
Air Conditioning · Dishwasher · Swimming Pool ·
From
$183/night
Min stay: 365 nights
Property
Condo · 2 Beds · 2 baths
Amenities
Air Conditioning
Dishwasher
Swimming Pool
In Unit Laundry
Low Rise (1-3) - NAPLES, FL

No rating

·
Winter Park
·
2 br
·
Swimming Pool · Ceiling Fan · Furnished ·
From
$150/night
Min stay: 365 nights
Property
Condo · 2 Beds · 2 baths
Amenities
Swimming Pool
Ceiling Fan
Furnished
In Unit Laundry
Dishwasher

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 $63. Use the price filter at the top of the page to search for more specific prices.
3 Miles to Beautiful Naples Beach Shopping and Paradise
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 6
·
Air Conditioning · Dishwasher · Beach ·
From
$63/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Air Conditioning
Dishwasher
Beach
Oven
Pool
Swimming Pool
In Unit Laundry
Furnished
Other spaces
Balcony, Kitchen
2021 Availability Winter Park Close to Pool1st Floor
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Pool · Oven · Walk In Closets ·
From
$85/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Pool
Oven
In Unit Laundry
Residents Lounge
Dishwasher
Furnished
Swimming Pool
Air Conditioning
Other spaces
Walk In Closets, Outdoor Space, Kitchen
Huge Heated Pool, 10 min to the Beach & Downtown 5th Ave
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Swimming Pool · Air Conditioning · Kitchen ·
From
$102/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Swimming Pool
Air Conditioning
Assigned Parking
Beach
Pool
Residents Lounge
Dishwasher
On Site Laundry
Other spaces
Kitchen, Balcony, Walk In Closets, Workspace
Golf club Villa located in beautiful Naples , 5 min from Beaches and Downtown
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 6
·
Kitchen · Pool · In Unit Laundry ·
From
$111/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen, Walk In Closets
Expand your search criteria to see more vacation rentals near Winter Park.
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Updated: February 29, 2024