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Vacations by Zumper

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.
Lush Villa in golfing community close to Beaches and Shopping. 2 Golf Courses,
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
On Site Laundry · Oven · Air Conditioning ·
From
$119/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
On Site Laundry
Oven
Air Conditioning
Furnished
Dishwasher
Residents Lounge
Wifi
Swimming Pool
Other spaces
Kitchen
Affordable Naples Florida Vacation Perfect Condo
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Outdoor Space · Air Conditioning · Hardwood Floor ·
From
$109/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Air Conditioning
Hardwood Floor
Furnished
Oven
Dishwasher
In Unit Laundry
Pool
Beach
Other spaces
Balcony, Kitchen
Price drop
Luxurious holiday condo with oversize pool
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Furnished · Residents Lounge · Kitchen ·
From
$104/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
Quiet lovely 2-bed/bath condo in central Naples!
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 5
·
Dishwasher · Pool · Outdoor Space ·
From
$75/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
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
$101/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Swimming Pool
Air Conditioning
Assigned Parking
Beach
Walk In Closets
Pool
Residents Lounge
Dishwasher
Other spaces
Kitchen, Balcony, Workspace
Best of the Best Summer Sale!!
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 6
·
Beach · Furnished · Oven ·
From
$64/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Beach
Furnished
Oven
Waterfront
Wifi
Air Conditioning
In Unit Laundry
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.
Naples at Winterpark!

No rating

·
Winter Park
·
2 br
·
Sleeps 4
·
Dishwasher · Fitness Center · Furnished ·
From
$150/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Dishwasher
Fitness Center
Furnished
Oven
Beach
Residents Lounge
Air Conditioning
Swimming Pool
Other spaces
Kitchen
2 Bedroom (620609) by Houzlet

No rating

·
Winter Park
·
2 br
·
Sleeps 4
·
Swimming Pool · Dishwasher · Furnished ·
From
$219/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Swimming Pool
Dishwasher
Furnished
On Site Laundry
Pool
In Unit Laundry
Beach
Storage
Other spaces
Kitchen
Price drop
Escape to Naples!

No rating

·
Winter Park
·
Studio
·
Sleeps 5
·
High Ceilings · Kitchen · Oven ·
From
$88/night
Check availability
Property
Condo · Studio
Amenities
High Ceilings
Oven
Air Conditioning
Fireplace
Dishwasher
Furnished
Swimming Pool
In Unit Laundry
Other spaces
Kitchen, Balcony
"TOMMY BAHAMAS CONDO"

No rating

·
Winter Park
·
2 br
·
Sleeps 2
·
Furnished · Outdoor Space · Beach ·
From
$99/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Furnished
Beach
Elevator
Wifi
On Site Laundry
Mountains
Pool
Residents Lounge
Other spaces
Kitchen
Price drop
Beautiful, updated 2/2 condo close to shops, restaurants and beaches
4

Good

·
Winter Park
·
2 br
·
Sleeps 5
·
Swimming Pool · Air Conditioning · Wifi ·
From
$258/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Swimming Pool
Air Conditioning
Wifi
Pool
Dishwasher
Furnished
Beach
In Unit Laundry
Other spaces
Kitchen

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
Beautiful lake view huge pool 4 miles to Gulf beaches
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
On Site Laundry · Dishwasher · Oven ·
From
$70/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
On Site Laundry
Dishwasher
Oven
Furnished
Wifi
Fitness Center
In Unit Laundry
Waterfront
Other spaces
Kitchen, Workspace
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
Walk In Closets
In Unit Laundry
Residents Lounge
Dishwasher
Furnished
Swimming Pool
Other spaces
Kitchen
Expand your search criteria to see more vacation rentals near Winter Park.
Home > Florida Vacation Rentals > Bonita Springs-Naples Vacation Rentals > Winter Park Vacation Rentals
Updated: September 22, 2023