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Vacations by Zumper

Vacation Rentals in Windermere, FL

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Windermere, FL

Book a vacation rental in Windermere that has the highest visitor rating. Here are 6 of the best vacation rentals in Windermere.
Price drop
Luxury 2BDR /Gated/Resort Style Pool/Gym/FastWifi
10

Excellent

·
Windermere
·
2 br
·
Sleeps 6
·
Outdoor Space · Air Conditioning · Fitness Center ·
From
$194/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Air Conditioning
Fitness Center
Pool
Swimming Pool
Furnished
Oven
On Site Laundry
Dishwasher
Other spaces
Kitchen, Balcony
Price drop
Welcome to the Farm House! Excellent Location, Pet Friendly!
10

Excellent

·
Windermere
·
3 br
·
Sleeps 10
·
Onsite Management · Wifi · Oven ·
From
$181/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Onsite Management
Wifi
Oven
Fireplace
Storage
Fitness Center
Walk In Closets
On Site Laundry
Other spaces
Workspace, Kitchen
Relaxing 1bedroom Condo by Universal & Disney 7min walk ICON park & Orlando eye
10

Excellent

·
Windermere
·
1 br
·
Sleeps 4
·
Wifi · Pool · Furnished ·
From
$113/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
Wifi
Pool
Furnished
Fitness Center
Air Conditioning
On Site Laundry
Dishwasher
Swimming Pool
Other spaces
Kitchen
Price drop
The Home of Sweet Peace
10

Excellent

·
Windermere
·
4 br
·
Sleeps 6
·
On Site Laundry · Outdoor Space · Fireplace ·
From
$450/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
On Site Laundry
Fireplace
Furnished
Oven
Wifi
Waterfront
Dishwasher
Air Conditioning
Other spaces
Kitchen
2BR Orlando Oasis: Balcony, Cozy, Great Amenities!
10

Excellent

·
Windermere
·
2 br
·
Sleeps 4
·
Furnished · In Unit Laundry · Oven ·
From
$149/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Furnished
In Unit Laundry
Oven
Air Conditioning
Swimming Pool
Fitness Center
Pool
Other spaces
Kitchen
Windermere CasaMirella · 2BR/Modern/Fast Wifi/Pool/gym/near Disney Parks
10

Excellent

·
Windermere
·
2 br
·
Sleeps 6
·
Swimming Pool · On Site Laundry · Balcony ·
From
$124/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Swimming Pool
On Site Laundry
Oven
Furnished
Fitness Center
Dishwasher
Residents Lounge
Assigned Parking
Other spaces
Balcony, Kitchen

Our Recommended Vacation Rentals in Windermere, FL

We analyzed vacation rentals in Windermere 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 Windermere to help you find a deal for your next trip.
Price drop
Rustic Hideaway - Modern Estate - Great Location + Pet Friendly!

No rating

·
Windermere
·
4 br
·
Sleeps 9
·
Fitness Center · On Site Laundry · Outdoor Space ·
From
$173/night
Check availability
Property
Apartment · 4 Beds · 4 baths
Amenities
Fitness Center
On Site Laundry
Walk In Closets
Air Conditioning
Ceiling Fan
Oven
Dishwasher
Wifi
Other spaces
Workspace, Balcony, Kitchen
Tranquil Oasis - Pool - Gym- Kid/Pet Friendly

No rating

·
Windermere
·
2 br
·
Sleeps 6
·
On Site Laundry · Residents Lounge · Outdoor Space ·
From
$222/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
On Site Laundry
Residents Lounge
Air Conditioning
Wifi
Fitness Center
Furnished
Swimming Pool
Other spaces
Kitchen, Balcony
Rent special
Landing Furnished Apartment at 2BR Windermere Fl Pool gym wifi Disney.4206.1389125

No rating

·
Windermere
·
2 br
·
Fitness Center · Package Service · Furnished ·
From
$122/night
Min stay: 30 nights
Property
Apartment · 2 Beds · 2 baths
Amenities
Fitness Center
Package Service
Furnished
Swimming Pool
Rent special
Landing Furnished Apartment at Casa Mirella.7209.1358332

No rating

·
Windermere
·
1 br
·
Package Service · Furnished ·
From
$89/night
Min stay: 30 nights
Property
Apartment · 1 Bed · 1 bath
Amenities
Package Service
Furnished

Budget-Friendly Vacation Rentals in Windermere, FL

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Windermere starting at $77. Use the price filter at the top of the page to search for more specific prices.
1BR 1BA Private Suite, Pool, Washer/Dryer, WiFi, Dog-Friendly, Fully Furnished

No rating

·
Windermere
·
1 br
·
Hardwood Floor · Cable · High Ceilings ·
From
$77/night
Min stay: 30 nights
Property
Apartment · 1 Bed · 1 bath
Amenities
Hardwood Floor
Cable
High Ceilings
Swimming Pool
On Site Laundry
Microwave
Assigned Parking
Furnished
Near Disney, amazing, private and comfortable room

No rating

·
Windermere
·
1 br
·
Sleeps 28
·
Air Conditioning · Furnished · Wifi ·
From
$79/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
Wifi
Rent special
Landing Furnished Apartment at Casa Mirella Lakeview.2109.1357721

No rating

·
Windermere
·
1 br
·
Furnished · Package Service ·
From
$93/night
Min stay: 30 nights
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Package Service
COZY & LUXURY Apt with LAKE VIEW, cable and fast WiFi near all Attractions!

No rating

·
Windermere
·
1 br
·
Sleeps 4
·
In Unit Laundry · Kitchen · Wifi ·
From
$98/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
In Unit Laundry
Wifi
Oven
Air Conditioning
Fitness Center
Furnished
Pool
Swimming Pool
Other spaces
Kitchen, Balcony, Workspace
Price drop
Cozy & Comfy Lakeview 1BD in Central Orlando

No rating

·
Windermere
·
1 br
·
Sleeps 2
·
Swimming Pool · Pool · Air Conditioning ·
From
$107/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Swimming Pool
Pool
Air Conditioning
On Site Laundry
Furnished
Residents Lounge
Fitness Center
Other spaces
Kitchen
Expand your search criteria to see more vacation rentals near Windermere.
Home > Florida Vacation Rentals > Windermere Vacation Rentals
Updated: September 24, 2023