Key West Cottage Rentals
· Apartment in Key West
Architects Cottage in fantastic Old Town location!
4 Beds · 3 baths · Sleeps 8 ·
Carpet · Ceiling Fan · Outdoor Space ·
From
$256/nightAmenities
Carpet
Ceiling Fan
Private Pool
Fitness Center
Dishwasher
Pool
Wifi
Oven
Other spaces
Kitchen
· Apartment in Key West
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
2 Beds · 2 baths · Sleeps 6 ·
Free Parking · Assigned Parking · Dishwasher ·
From
$363/nightAmenities
Free Parking
Assigned Parking
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
· Apartment in Key West
Cozy Cottage with Porch, WiFI, AC, & Amazing Walking Locale - Small Dogs OK
1 Bed · 2 baths · Sleeps 4 ·
Free Parking · On Site Laundry · Assigned Parking ·
From
$256/nightAmenities
Free Parking
On Site Laundry
Assigned Parking
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Pete's Cottages: Twin Cypress cottages steps from Duval
4 Beds · 2 baths · Sleeps 8 ·
Fitness Center · Dishwasher · Pool ·
From
$873/nightAmenities
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Pete's East Cottage: Cypress east cottage steps from Duval
2 Beds · 1 bath · Sleeps 4 ·
Fitness Center · Dishwasher · Pool ·
From
$429/nightAmenities
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Havana Lane: An updated classic conch cottage with still a rustic edge!
2 Beds · 2 baths · Sleeps 4 ·
On Site Laundry · Private Pool · Fitness Center ·
From
$1,129/nightAmenities
On Site Laundry
Private Pool
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Other spaces
Kitchen
· Apartment in Key West
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
1 Bed · 1 bath · Sleeps 2 ·
Fitness Center · Pool · Wifi ·
From
$392/nightAmenities
Fitness Center
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
· Apartment in Key West
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
4 Beds · 3 baths · Sleeps 8 ·
Ceiling Fan · Private Pool · Fitness Center ·
From
$1,343/nightAmenities
Ceiling Fan
Private Pool
Fitness Center
Dishwasher
Pool
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
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· Apartment in Key West
~ COPA CABANA ~ Classic Key West cottage just a stone’s throw from the water.
2 Beds · 2 baths ·
Ceiling Fan · Hardwood Floor · Private Pool ·
From
$209/nightAmenities
Ceiling Fan
Hardwood Floor
Private Pool
Fitness Center
Dishwasher
Pool
Wifi
Oven
Other spaces
Kitchen
· Apartment in Key West
Mango Cottage- 2 bedroom 2 bath with private pool
2 Beds · 2 baths · Sleeps 6 ·
High Ceilings · Assigned Parking · Private Pool ·
From
$633/nightAmenities
High Ceilings
Assigned Parking
Private Pool
Dishwasher
Pool
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
· Apartment in Key West
Pete's West Cottage steps from Duval
2 Beds · 1 bath · Sleeps 4 ·
Fitness Center · Dishwasher · Pool ·
From
$318/nightAmenities
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
4 Beds · 4 baths · Sleeps 12 ·
Outdoor Space · High Ceilings · Assigned Parking ·
From
$557/nightAmenities
High Ceilings
Assigned Parking
Private Pool
Fitness Center
Dishwasher
Pool
Wifi
Oven
Other spaces
Kitchen
· Apartment in Key West
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
2 Beds · 2 baths · Sleeps 6 ·
Assigned Parking · Private Pool · Beach ·
From
$369/nightAmenities
Assigned Parking
Private Pool
Beach
Fitness Center
Dishwasher
Pool
Wifi
Oven
Other spaces
Kitchen
· Apartment in Key West
TRANQUILITY - Meadows Monthly Rental - Private Pool - 3BDR/3BA - RealKeyWest
3 Beds · 3 baths ·
Private Pool · Beach · Fitness Center ·
From
$321/nightAmenities
Private Pool
Beach
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Other spaces
Kitchen
· Apartment in Key West
CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD/1BA RealKeyWest
1 Bed · 1 bath · Sleeps 2 ·
Hot Tub · Outdoor Space · Assigned Parking ·
From
$544/nightAmenities
Hot Tub
Assigned Parking
Beach
Fitness Center
Dishwasher
Pool
Wifi
Oven
Other spaces
Kitchen
· Apartment in Key West
Key West Treehouse in Old Town
1 Bed · 2 baths · Sleeps 4 ·
Workspace · Balcony · Beach ·
From
$239/nightAmenities
Beach
Dishwasher
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Balcony, Kitchen
· Apartment in Key West
Colony Sunset- Bright and airy cottage in the heart of old town Key West
1 Bed · 1 bath ·
High Ceilings · Fitness Center · Pool ·
From
$357/nightAmenities
High Ceilings
Fitness Center
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Old Town cottage just steps from Duval Street
1 Bed · 2 baths ·
On Site Laundry · Assigned Parking · Dishwasher ·
From
$300/nightAmenities
On Site Laundry
Assigned Parking
Dishwasher
Wifi
In Unit Laundry
Air Conditioning
Furnished
Storage
Other spaces
Kitchen
· Apartment in Key West
Margarita Cottage- 1 bedroom 1 bath with shared pool
1 Bed · 1 bath · Sleeps 2 ·
Private Pool · Pool · Oven ·
From
$444/nightAmenities
Private Pool
Pool
Oven
In Unit Laundry
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
· Apartment in Key West
Butterfly Garden Flat
1 Bed · 1 bath · Sleeps 2 ·
Hardwood Floor · Beach · Fitness Center ·
From
$143/nightAmenities
Hardwood Floor
Beach
Fitness Center
Dishwasher
Wifi
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
· Apartment in Key West
Downtown Cottage just off famous Duval Street-No Contact Check-In
2 Beds · 2 baths · Sleeps 6 ·
Smoking Allowed · Fitness Center · Pool ·
From
$279/nightAmenities
Smoking Allowed
Fitness Center
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Downtown Location in Historic District-No Contact Check-In
1 Bed · 1 bath · Sleeps 4 ·
Smoking Allowed · Workspace · Outdoor Space ·
From
$280/nightAmenities
Smoking Allowed
Pool
Wifi
Oven
Air Conditioning
Furnished
Swimming Pool
Elevator
Other spaces
Workspace, Kitchen
· Apartment in Key West
Open March 2023 Quaint Pool Cottage in the heart of Old Town Key West
2 Beds · 1 bath ·
Pool · In Unit Laundry · Air Conditioning ·
From
$227/nightAmenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
· Apartment in Key West
A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW
2 Beds · 1 bath ·
Workspace · Outdoor Space · Beach ·
From
$185/nightAmenities
Beach
Fitness Center
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
· Apartment in Key West
Maryann's Place - Large Monthly Studio (New Listing)
Studio · 1 bath · Sleeps 2 ·
High Ceilings · Fitness Center · Dishwasher ·
From
$207/nightAmenities
High Ceilings
Fitness Center
Dishwasher
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Havana Moon over Duval
2 Beds · 2 baths · Sleeps 6 ·
Deck · Balcony · Hardwood Floor ·
From
$639/nightAmenities
Hardwood Floor
High Ceilings
Private Pool
Beach
Dishwasher
Pool
Wifi
Oven
Other spaces
Deck, Balcony, Kitchen
· Apartment in Key West
New Unit coming to Compass Realty at the Key West Golf Club
3 Beds · 3 baths · Sleeps 6 ·
Pool · Wifi · In Unit Laundry ·
From
$260/nightAmenities
Pool
Wifi
In Unit Laundry
Air Conditioning
Furnished
Swimming Pool
Fitness Center
Other spaces
Kitchen
· Apartment in Key West
John Truman's Hideaway~ Walk to Duval Street from this splendid cottage!
1 Bed · 1 bath ·
Free Parking · On Site Laundry · Ceiling Fan ·
From
$402/nightAmenities
Free Parking
On Site Laundry
Ceiling Fan
Hardwood Floor
High Ceilings
Pool
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
· Apartment in Key West
Cockadoodle Cottage on Duval
2 Beds · 2 baths · Sleeps 6 ·
Balcony · High Ceilings · Beach ·
From
$504/nightAmenities
High Ceilings
Beach
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
· Apartment in Key West
Heart of Downtown Key West Cottage With Off-Street Parking
2 Beds · 1 bath · Sleeps 4 ·
Assigned Parking · Fitness Center · Dishwasher ·
From
$400/nightAmenities
Assigned Parking
Fitness Center
Dishwasher
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Old Town- Walk to everything- Banyan tree view
1 Bed · 2 baths · Sleeps 4 ·
Beach · Fitness Center · Dishwasher ·
From
$245/nightAmenities
Beach
Fitness Center
Dishwasher
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Charming Old Town Historic Cottage - Walk & Bike to Everything!
2 Beds · 2 baths · Sleeps 6 ·
Wifi · In Unit Laundry · Air Conditioning ·
From
$295/nightAmenities
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
3 blocks from waterfront and 1 block off Duval in Old Town Key West
1 Bed · 1 bath · Sleeps 4 ·
Hot Tub · Outdoor Space · Assigned Parking ·
From
$410/nightAmenities
Hot Tub
Assigned Parking
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Sea Breeze Cottage in Truman Annex Location! Location! Location!
3 Beds · 2 baths · Sleeps 6 ·
Waterfront · Workspace · Balcony ·
From
$500/nightAmenities
Waterfront
Beach
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Other spaces
Workspace, Balcony, Kitchen
· Apartment in Key West
Classic Historic Key West Cottage
2 Beds · 1 bath ·
Hardwood Floor · High Ceilings · In Unit Laundry ·
From
$275/nightAmenities
Hardwood Floor
High Ceilings
In Unit Laundry
Furnished
Storage
Other spaces
Kitchen
· Apartment in Key West
Clean/stylish Old Town Key West- Walk to Duval
1 Bed · 2 baths · Sleeps 4 ·
Assigned Parking · Beach · Fitness Center ·
From
$260/nightAmenities
Assigned Parking
Beach
Fitness Center
Dishwasher
Wifi
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
· Apartment in Key West
Casa Manana Key West Monthly: 2 BR, 2 BA Cottage in Key West, Sleeps 6
2 Beds · 2 baths · Sleeps 6 ·
Walk In Closets · On Site Laundry · Ceiling Fan ·
From
$302/nightAmenities
Walk In Closets
On Site Laundry
Ceiling Fan
Hardwood Floor
High Ceilings
Private Pool
Fitness Center
Dishwasher
Other spaces
Kitchen
· Apartment in Key West
Paradise in the off-season. Book for summer now!
2 Beds · 1 bath · Sleeps 4 ·
Smoking Allowed · Hot Tub · Dishwasher ·
From
$200/nightAmenities
Smoking Allowed
Hot Tub
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
· Apartment in Key West
Cozy studio cottage in Old Town Key West
1 Bed · 1 bath · Sleeps 4 ·
Waterfront · Beach · Pool ·
From
$200/nightAmenities
Waterfront
Beach
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
A Touch of Bermuda at Truman Annex
2 Beds · 2 baths · Sleeps 6 ·
Free Parking · Balcony · Outdoor Space ·
From
$400/nightAmenities
Free Parking
Beach
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
· Apartment in Key West
Southernmost Retreat: 2 Blocks from Duval in Old Town.
3 Beds · 2 baths · Sleeps 6 ·
Assigned Parking · Beach · Fitness Center ·
From
$575/nightAmenities
Assigned Parking
Beach
Fitness Center
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
2 Beds · 2 baths ·
Private Pool · Beach · Fitness Center ·
From
$816/nightAmenities
Private Pool
Beach
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Other spaces
Kitchen
· Apartment in Key West
ELIZABETH'S SECRET: 3/2-Old Town-Private pool-Parking - RealKeyWest
3 Beds · 2 baths ·
Private Pool · Beach · Fitness Center ·
From
$1,394/nightAmenities
Private Pool
Beach
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Other spaces
Kitchen
· Apartment in Key West
PAGITT HOUSE: Old Town - Private Pool - 3BR/2BA - Sleeps 6 - RealKeyWest
3 Beds · 2 baths · Sleeps 6 ·
Balcony · Assigned Parking · Fitness Center ·
From
$973/nightAmenities
Assigned Parking
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Other spaces
Balcony, Kitchen
· Apartment in Key West
"Tranquility " At Ann Street Gardens Steps From Duval
1 Bed · 1 bath · Sleeps 2 ·
Outdoor Space · Fitness Center · Dishwasher ·
From
$762/nightAmenities
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
1 Bedroom Cottage in the heart of Downtown. 1/2 block away from Duval Street
1 Bed · 1 bath · Sleeps 4 ·
Outdoor Space · Wifi · Oven ·
From
$653/nightAmenities
Wifi
Oven
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Royal Poinciana Cottage
1 Bed · 1 bath · Sleeps 2 ·
Pool · Oven · In Unit Laundry ·
From
$368/nightAmenities
Pool
Oven
In Unit Laundry
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
· Apartment in Key West
Colony Poolside: A charming bungalow near Duval Street
1 Bed · 1 bath · Sleeps 2 ·
Hardwood Floor · High Ceilings · Fitness Center ·
From
$342/nightAmenities
Hardwood Floor
High Ceilings
Fitness Center
Pool
Wifi
Oven
Air Conditioning
Furnished
Other spaces
Kitchen
· Apartment in Key West
Ann Street Cottage: A bright and airy home near Duval Street
1 Bed · 2 baths · Sleeps 2 ·
Workspace · On Site Laundry · High Ceilings ·
From
$476/nightAmenities
On Site Laundry
High Ceilings
Fitness Center
Dishwasher
Pool
Wifi
Oven
In Unit Laundry
Other spaces
Workspace, Kitchen
· Apartment in Key West
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
2 Beds · 2 baths · Sleeps 4 ·
Ceiling Fan · Balcony · Dishwasher ·
From
$1,035/nightAmenities
Ceiling Fan
Dishwasher
Pool
Wifi
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Other spaces
Balcony, Kitchen
Showing 1 - 50 of 51 results
Updated: March 16, 2023
Learn about vacation rentals in
Key West
Explore 1767 vacation rentals near Key West, Florida. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Key West, you can see photos of Key West vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Key West vacation rentals in specific areas. Whether you’re looking for a Key West staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Key West is $143 per night and the highest price is $1,394 per night.
The most common
amenities for vacation rentals near Key West are: furnished, kitchen, and air conditioning. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
488 available
2 bed rentals
737 available
3 bed rentals
254 available
4+ bed rentals
226 available
Getting around Key West
Walking
6/10
Grab your reusable bags–many shops and stores are within walking distance.
Car
10/10
Commuting is easy with multiple accessible routes and plenty of parking.
Transit
3/10
There are a few mass transit options within the area.
Points of interest in Key West
Groceries
7/10
At least one grocery store within a 15-minute walk
Shopping
6/10
Variety of shops within walking distance
Cafes
4/10
Some cafés within walking distance
Restaurants
6/10
Some restaurants within walking distance
Nightlife
4/10
Some bars within walking distance
Key West Cottage Rentals FAQ
How many cottage vacation rentals in Key West are available?
As of March 16, 2023, there are 51 cottage vacation rentals in Key West available.
Do any Key West cottage rentals have internet access?
There are 44 cottage rentals in Key West that have internet access.
Are there any pet friendly cottage rentals in Key West?
There are 13 pet friendly cottage rentals in Key West. A pet friendly rental allows pets such as dogs or cats. We recommend contacting the listing owner for more specific pet details.
Are there any cottage rentals in Key West with more than 1 bedroom?
There are 50 cottage rentals in Key West with more than 1 bedroom. Use the filters on Vacations by Zumper to find more specific rental properties.
