Vacation House Rentals In Key West With Pool

Top-Rated Vacation Rentals in Key West, FL

Book a vacation rental in Key West that has the highest visitor rating. Here are 6 of the best vacation rentals in Key West.
Price drop
Smooth Sailing by Brightwild-Pool & Boat Dock
10

Excellent

·
Key West
·
4 br
·
Sleeps 10
·
Outdoor Space · Kitchen · Air Conditioning ·
From
$2,190/night
Check availability
Property
Apartment · 4 Beds · 5 baths
Amenities
Air Conditioning
Pool
Oven
Free Parking
Dishwasher
Wifi
Furnished
Swimming Pool
Other spaces
Kitchen
Price drop
Modern Keys by Brightwild-Waterfront w Dock
10

Excellent

·
Key West
·
4 br
·
Sleeps 10
·
Furnished · Private Pool · Air Conditioning ·
From
$2,190/night
Check availability
Property
Apartment · 4 Beds · 5 baths
Amenities
Furnished
Private Pool
Air Conditioning
Swimming Pool
Free Parking
Pool
Wifi
Oven
Other spaces
Kitchen
Price drop
Sophisticated Sunsets by Brightwild-Pool & Dock!
10

Excellent

·
Key West
·
4 br
·
Sleeps 12
·
Outdoor Space · Dishwasher · Free Parking ·
From
$2,435/night
Check availability
Property
Apartment · 4 Beds · 4 baths
Amenities
Dishwasher
Free Parking
Oven
Furnished
Private Pool
Swimming Pool
Wifi
Air Conditioning
Other spaces
Kitchen
Price drop
Contra House by Brightwild-Luxury Home With Pool
10

Excellent

·
Key West
·
4 br
·
Sleeps 12
·
Private Pool · Furnished · Kitchen ·
From
$2,822/night
Check availability
Property
Apartment · 4 Beds · 4 baths
Amenities
Private Pool
Furnished
Dishwasher
Wifi
Pool
Air Conditioning
Swimming Pool
Free Parking
Other spaces
Kitchen
Price drop
Keys Please by Brightwild
10

Excellent

·
Key West
·
3 br
·
Sleeps 6
·
Wifi · Furnished · Kitchen ·
From
$1,787/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Wifi
Furnished
Swimming Pool
Air Conditioning
Dishwasher
Private Pool
Free Parking
Oven
Other spaces
Kitchen
Price drop
Passover Cottage
10

Excellent

·
Key West
·
2 br
·
Sleeps 4
·
Dishwasher · Outdoor Space · Pool ·
From
$627/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Dishwasher
Pool
Furnished
In Unit Laundry
Air Conditioning
Wifi
Oven
Swimming Pool
Other spaces
Kitchen

Our Recommended Vacation Rentals in Key West, FL

We analyzed vacation rentals in Key West 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 Key West to help you find a deal for your next trip.
Price drop
Helen's Hideaway by Brightwild
8

Very good

·
Key West
·
2 br
·
Sleeps 6
·
Oven · Private Pool · Kitchen ·
From
$1,542/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Oven
Private Pool
Wifi
Dishwasher
Air Conditioning
Furnished
Swimming Pool
Free Parking
Other spaces
Kitchen
Price drop
Duval Street Suite overlooking Duval with parking and pool
8.5

Very good

·
Key West
·
1 br
·
Sleeps 4
·
Furnished · Outdoor Space · Dishwasher ·
From
$416/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Dishwasher
Pool
Wifi
Swimming Pool
Oven
Free Parking
Air Conditioning
Other spaces
Kitchen
Price drop
Poolside Paradise by Brightwild
6

Good

·
Key West
·
3 br
·
Sleeps 10
·
Swimming Pool · Wifi · Private Pool ·
From
$1,660/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Swimming Pool
Wifi
Private Pool
Air Conditioning
Furnished
Pool
Free Parking
Other spaces
Kitchen

Budget-Friendly Vacation Rentals in Key West, FL

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Key West starting at $87. Use the price filter at the top of the page to search for more specific prices.
Price drop
Curry House by Brightwild | Balcony & Pool - Rm #9
10

Excellent

·
Key West
·
1 br
·
Sleeps 2
·
In Unit Laundry · Wifi · Pool ·
From
$87/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
In Unit Laundry
Wifi
Pool
Swimming Pool
Air Conditioning
Private Pool
Furnished
Other spaces
Kitchen, Balcony
Price drop
Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK
10

Excellent

·
Key West
·
1 br
·
Sleeps 2
·
Kitchen · In Unit Laundry · Swimming Pool ·
From
$115/night
Check availability
Property
House · 1 Bed · 2 baths
Amenities
In Unit Laundry
Swimming Pool
Furnished
Oven
Free Parking
Pool
Wifi
On Site Laundry
Other spaces
Kitchen
Campbell Cottage in Key West

No rating

·
Key West
·
1 br
·
Sleeps 2
·
Residents Lounge · Furnished · Ceiling Fan ·
From
$115/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Residents Lounge
Furnished
Ceiling Fan
Storage
Pool
Wifi
Beach
Swimming Pool
Other spaces
Kitchen
MONTHLY RENTAL, OCT/FF OPEN, Old Town, Duplex, newly renovated, private backyard
10

Excellent

·
Key West
·
2 br
·
Sleeps 4
·
Workspace · Onsite Management · Kitchen ·
From
$120/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Onsite Management
Oven
Wifi
Swimming Pool
Dishwasher
In Unit Laundry
Fitness Center
Furnished
Other spaces
Workspace, Kitchen, Balcony
Ibis by AvantStay | Close to Duval Street w/ Shared Pool | Month Long Stays Only

No rating

·
Key West
·
1 br
·
Sleeps 2
·
Air Conditioning · Swimming Pool · Furnished ·
From
$124/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Air Conditioning
Swimming Pool
Furnished
In Unit Laundry
Pool
Dishwasher
On Site Laundry
Wifi
Other spaces
Kitchen
Price drop
Cottage by the Pool by AvantStay | w/ Balcony, BBQ & Shared Pool!
10

Excellent

·
Key West
·
2 br
·
Sleeps 4
·
Pool · Balcony · Swimming Pool ·
From
$134/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Pool
Swimming Pool
Air Conditioning
Dishwasher
Furnished
Oven
Wifi
In Unit Laundry
Other spaces
Balcony, Kitchen

Vacation Rentals With AC and/or Heat in Key West, FL

Whether you need air conditioning or central heating, these vacation rentals are for you.
Paris Mango: Waterfront Luxury Home with Ocean View & Heated Private Pool!
10

Excellent

·
Key West
·
4 br
·
Sleeps 8
·
Pool · Hot Tub · Furnished ·
From
$989/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Pool
Hot Tub
Furnished
In Unit Laundry
Storage
Ceiling Fan
Swimming Pool
Central Heat
Other spaces
Kitchen, Balcony
Nautical Wheeler: Waterfront Home with private Pool & lush landscaping
10

Excellent

·
Key West
·
4 br
·
Sleeps 8
·
Ocean · Kitchen · Swimming Pool ·
From
$1,017/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Ocean
Swimming Pool
Furnished
Walk In Closets
In Unit Laundry
Central Heat
Waterfront
Dishwasher
Other spaces
Kitchen, Balcony
Price drop
**THE ENCHANTED ROSE @ BEACHSIDE** Gorgeous Home & Pool + LAST KEY SERVICES…

No rating

·
Key West
·
3 br
·
Sleeps 10
·
Air Conditioning · Central Heat · Residents Lounge ·
From
$293/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Air Conditioning
Central Heat
Residents Lounge
Wifi
Oven
Swimming Pool
In Unit Laundry
Pool
Other spaces
Workspace, Kitchen
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Updated: October 1, 2023