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Featured Vacation Rental

LA CASA DEL DORADO ~ Island Urban!
A Pet Friendly rental is a MONTHLY property that considers pets. Our nightly and weekly rentals are not pet friendly. There are many factors that decide whether a pet will be accepted at a property: Size, Breed, Flooring, # of Pets, etc. We require a $250 refundable pet deposit per animal and the cleaning fee may increase depending on the breed and size of the pet.
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RIPTIDES ~ Stylish Studio!
STYLISH STUDIO ONE BLOCK FROM DUVAL… Private studio on Simonton Street one block from Duval.    This home is perfect for a couple wh......
Property Code: Riptides
Bedrooms: 0 | Bathrooms: 1 | Max Occupancy: 2
Pets Allowed: No
PINEAPPLE COTTAGE~ Laid Back!
RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. Located one block from Duval with cha......
Property Code: Pineapple Cottage
Bedrooms: 1 | Bathrooms: 1 | Max Occupancy: 4
Location: Key West
Pets Allowed: No
SWEET CAROLINE~ So Good!
LIVE LIKE A LOCAL… “Sweet Caroline” is located inside a beautiful classic Key West home right in the heart of Old Town.   Enj......
Property Code: Sweet Caroline
Bedrooms: 1 | Bathrooms: 2 | Max Occupancy: 4
Location: Old Town
Pets Allowed: No
LA PORCHALADA~ Funky!
RELAXED LIVING... La Porchalada is a lovely one bedroom located in, what Key Westers consider to be, the best spot on the island! The condo offers ov......
Property Code: La Porchalada
Bedrooms: 1 | Bathrooms: 1 | Max Occupancy: 2
Location: Key West
Pets Allowed: No
SEAPORT SANCTUARY~ Romantic!
A QUIET BUNGALOW IN THE HISTORIC SEAPORT... Private one bedroom home in the heart of Old Town.  A great place for a couple's getaway where y......
Property Code: Seaport Sanctuary
Bedrooms: 1 | Bathrooms: 1 | Max Occupancy: 4
Location: Old Town
Pets Allowed: Yes
TIDES ON SIMONTON~ Easy Life!
ADORING COTTAGE ONE BLOCK FROM DUVAL… Private one bedroom cottage on Simonton Street one block from Duval.  Totaling one bedroom, one bat......
Property Code: Tides On Simonton
Bedrooms: 1 | Bathrooms: 1 | Max Occupancy: 4
Location: Old Town
Pets Allowed: Yes
TURTLE COVE ~ Leisure Living!
A SWEET RETREAT MINTUES AWAY FROM THE BEACH… Perfect apartment located in Old Town in the desired Casa Marina District.  Totaling one bed......
Property Code: Turtle Cove
Bedrooms: 1 | Bathrooms: 1 | Max Occupancy: 4
Location: Casa Marina
Pets Allowed: Yes
MANGO MARGARITA~ Upper Duval Hideaway!
LOCATION... Enjoy this convenient Old Town Location.  Located a block from Duval and a short walk or bike ride to everything Key West has to off......
Property Code: Mango Margarita
Bedrooms: 2 | Bathrooms: 2.5 | Max Occupancy: 6
Location: Old Town
Pets Allowed: No
BLUE BANYAN~Luxury Stay, Steps Away!
PERFECT LOCATION WITH HIGH END DESIGN... Conveniently located in Old Town, this luxurious single family home has a modern look with a comfortable fee......
Property Code: Blue Banyan
Bedrooms: 2 | Bathrooms: 2.5 | Max Occupancy: 6
Location: Old Town
Pets Allowed: Yes
ATLANTIC BREEZE~ Tropical Retreat by the Beach!
BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duval.  Updated condominium ......
Property Code: Atlantic Breeze
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Pets Allowed: No
THE QUARTERDECK~ Vibrant!
COMFORT AND VALUE IN TRUMAN ANNEX…. This newly renovated two bedroom condo is located in The Shipyard, a neighborhood of Truman Annex in the h......
Property Code: The Quarterdeck
Bedrooms: 2 | Bathrooms: 1 | Max Occupancy: 4
Location: Truman Annex
Pets Allowed: No
DANCING PALMS ~ Cheerful!
THE HEART OF OLD TOWN... A beautifully furnished and comfortable town home, located within the prestigious President`s Walk at Truman Annex. FURNI......
Property Code: Dancing Palms
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Truman Annex
Pets Allowed: Yes
LAZY DAZE ~ RELAX!
"LAZY DAZE" ON WHITE... Steps away from several art galleries as well as The Studios of Key West.  This is an artist dream location. &......
Property Code: Lazy Daze
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Pets Allowed: No
TORTOISE SHELL II~ Special!
CLASSIC KEY WEST.... Tortoise Shell II is an elegant two bedroom, 2 bath condominium one block off of famous Duval Street. Second floor unit with tre......
Property Code: Tortoise Shell II
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Key West
Pets Allowed: No
SEAHORSE COVE~ Perfection!
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private, single family home......
Property Code: Seahorse Cove
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Old Town
Pets Allowed: No
THE NEST~ Walk to it all!
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer.  Modern cottage with Old Town Key W......
Property Code: The Nest
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Old Town
Pets Allowed: Yes
TURQUOISE MERMAID~ Beach Chic!
VACATION... like a local in Old Town Key West just a few short blocks from the Historic Seaport area where you will find waterfront restaurants and qu......
Property Code: Turquoise Mermaid
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Key West
Pets Allowed: No
OFF CALL~ Paradise Found!
GATED COMMUNITY CLOSE TO BOATING AND GOLFING... “OFF CALL” is a beautiful townhome in the Coral Hammock community; totaling two bedrooms,......
Property Code: Off Call
Bedrooms: 2 | Bathrooms: 2.5 | Max Occupancy: 6
Location: Coral Hammock
Pets Allowed: No
LA CASA DEL DORADO ~ Island Urban!
GREAT LOCATION... Enjoy this newly renovated Conch cottage in Old Town.  Located on little lane tucked away just steps from Duval or a bike ride......
Property Code: La Casa Del Dorado
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Old Town
Pets Allowed: No
THE NAUTILUS - Walk to it all!
SURROUNDED BY HISTORY AND BEAUTY... Nestled in Truman Annex along President’s Walk you will find The Nautilus; a sophisticated unit with comfor......
Property Code: The Nautilus
Bedrooms: 2 | Bathrooms: 2.5 | Max Occupancy: 4
Location: Truman Annex
Pets Allowed: Yes
CONCH HEAVEN ~ Refreshing Old Town Charm!
OLD TOWN LOCATION... A beautifully furnished and comfortable home, located a short distance from Duval Street.  Have bikes delivered and you wil......
Property Code: Conch Heaven
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Old Town
Pets Allowed: Yes
IN GOOD SPIRITS~ It`s a Deal!
BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duval.  Warm and welcom......
Property Code: In Good Spirits
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Key West
Pets Allowed: No
MEMORY MAKER~Ideal location!
A STYLISH CARIBBEAN SURPRISE RIGHT OFF DUVAL... Private single-family home with peaceful porches totaling two bedrooms, two and half baths plus wet b......
Property Code: Memory Maker
Bedrooms: 2 | Bathrooms: 2.5 | Max Occupancy: 4
Location: Old Town
Pets Allowed: No
VILLAGE ROOSTER - Rustic Retreat!
BAHAMA VILLAGE TREASURE... This pet friendly Old Town Key West home is just steps from the award winning restaurants and charming boutiques of Petron......
Property Code: Village Rooster
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Key West
Pets Allowed: Yes
VILLA AZUL ~ Perfect Location!
COMFORT AND VALUE IN OLD TOWN…. This second floor two bedroom condo is located in The Shipyard, a Truman Annex neighborhood.  You will en......
Property Code: Villa Azul
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Truman Annex
Pets Allowed: Yes
“STONE`S THROW” 2Bd Conch Cottage with Pool - PERFECT LOCATION!
CLOSE TO THE FUN.... This Adorable Conch Cottage is a “Stone’s Throw” from everything that Key West has to offer!  Literally s......
Property Code: Stone`s Throw
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Old Town
Pets Allowed: No
PARROTDISE -Luxury Cottage in the Meadows!
MODERN LUXURY IN THE MEADOWS…. This private, two bedroom cottage is the perfect place to unwind for a couple or a small family. Sliding glass ......
Property Code: Parrotdise
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: The Meadows
Pets Allowed: Yes
SPARROW`S LANDING~Commodious!
Located in the peaceful neighborhood locals call The Meadows, this home is set away from the noise of Duval but a short bike ride to the action. Look ......
Property Code: Sparrow`s Landing
Bedrooms: 3 | Bathrooms: 3.5 | Max Occupancy: 6
Location: The Meadows
Pets Allowed: No
SEA LA VIE ~ Cozy Elegance
THREE STORY GRANDEUR…Located in the Casa Marina District in Old Town.  This home is elegant, yet quite the tropical delight with rustic mo......
Property Code: Sea la Vie
Bedrooms: 3 | Bathrooms: 3 | Max Occupancy: 8
Location: Old Town
Pets Allowed: Yes
CORAL CABANA~ Tropical Stay!
GATED COMMUNITY, CLOSE TO BOATING AND GOLFING... Coral Cabana, in the Coral Hammock Community is a gorgeous three bedroom, three bath townhome with o......
Property Code: Coral Cabana
Bedrooms: 3 | Bathrooms: 3 | Max Occupancy: 8
Location: Coral Hammock
Pets Allowed: No
THE SEASHELL~ Spectacular!
When only the best will do! The Seashell is the classic Old Town Key West home. Perfect setting for your dream island vacation. This beautifully lands......
Property Code: The Seashell
Bedrooms: 3 | Bathrooms: 3 | Max Occupancy: 6
Location: Old Town
Pets Allowed: No
LADY ADMIRAL~ Steps to Duval!
A SWEET SURPRISE JUST OFF DUVAL... Private single family home with off street parking totaling three bedrooms, two and half baths plus outdoor shower......
Property Code: Lady Admiral
Bedrooms: 3 | Bathrooms: 2.5 | Max Occupancy: 8
Location: Old Town
Pets Allowed: No
LOST SHAKER~ Relax!
THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West.  Located on Southard Street just steps from Duval's many......
Property Code: Lost Shaker of Salt
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 8
Location: Old Town
Pets Allowed: Yes
KEY LIME LIVIN`~ Isle Style!
A HIDDEN GEM... A modern two story revival (Conch house) totaling 3 bedrooms, two and a half baths with a private garden patio, a front porch, and a ......
Property Code: Key Lime Livin`
Bedrooms: 3 | Bathrooms: 2.5 | Max Occupancy: 6
Location: Old Town
Pets Allowed: No
CAPT JACK`S HIDEAWAY~ Old Town Gem!
QUIET LOCATION, COMFORTABLE SPACE…Located in Old Town, this home sits on a quaint little lane.  With limited homes on this lane, it is nic......
Property Code: Capt Jack`s Hideaway
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 6
Location: Old Town
Pets Allowed: No
SUNKISSED~ When Location is Key!
JUST OFF DUVAL... Private single family home with three bedrooms and two bathrooms.  Open the rear French doors to a private backyard oasis with......
Property Code: Sunkissed
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 8
Location: Old Town
Pets Allowed: No
LUNA VERDE ~ Beachside Unique!
Luna Verde.... This home is nicely situated in a quiet neighborhood just a few shorts blocks from Higgs Beach and White Street Pier.   Sleepi......
Property Code: Luna Verde
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 6
Location: Casa Marina
Pets Allowed: No
CASA DE VINO~ Comfort at a Steal!
GATED COMMUNITY, CLOSE TO BOATING AND GOLFING... Casa de Vino, in the Coral Hammock Community is a gorgeous three bedroom, three bath townhome with o......
Property Code: Casa de Vino
Bedrooms: 3 | Bathrooms: 3 | Max Occupancy: 8
Location: Coral Hammock
Pets Allowed: No
CARIBBEAN SOUL~ Has it All!
Quintessential Key West vacation home leaving nothing more to be desired. Framed by a white picket fence you will be welcomed to this classic 2 story ......
Property Code: Caribbean Soul
Bedrooms: 3 | Bathrooms: 3.5 | Max Occupancy: 6
Location: Casa Marina
Pets Allowed: Yes
CASA VERDE~ Live Comfortably!
LOCAL LIVING.... Spend time in Paradise in the perfect home. Casa Verde is a beautiful designer decorated three bedroom home with 2.5 baths in an ama......
Property Code: Casa Verde
Bedrooms: 3 | Bathrooms: 2.5 | Max Occupancy: 6
Location: Key West
Pets Allowed: Yes
SERENITY ~ Impeccable!
LOCAL LIVING.... Spend time relaxing in Paradise in the perfect home. Serenity is a beautifully decorated,  3 bedroom home, with 3 baths in an a......
Property Code: Serenity
Bedrooms: 3 | Bathrooms: 3 | Max Occupancy: 7
Location: Old Town
Pets Allowed: No
DRIFTWOOD DAYS ~ Relaxing!
PERFECT LOCATION WITH MODERN CHARM... A complete  renovation embraces a fresh, modern look that compliments the historical beauty of this home. ......
Property Code: Driftwood Days
Bedrooms: 3 | Bathrooms: 3.5 | Max Occupancy: 8
Location: Old Town
Pets Allowed: Yes
BOOMERANG BOAT HOUSE~ Charm!
Return to Equanimity.… “Boomerang Boathouse” is nestled in the peaceful neighborhood locals refer to as The Meadows.  Taste......
Property Code: Boomerang Boat House
Bedrooms: 4 | Bathrooms: 2.5 | Max Occupancy: 8
Location: The Meadows
Pets Allowed: Yes
MARGAUX`S HIDEAWAY ~ Stunning!
ESCAPE TO THIS PEACEFUL PARADISE... "Margaux's Hideaway", is a luxury vacation rental named for its ties to the famous actress, model an......
Property Code: Margaux`s Hideaway
Bedrooms: 4 | Bathrooms: 3 | Max Occupancy: 8
Location: Old Town
Pets Allowed: Yes
BOUGAINVILLEA HOUSE - Elegant Endeavor, 3Bd Grand Home with Guest House
GORGEOUS OLD TOWN HOME... Located in the Historic District of Key West just blocks from Duval Street.  It is a luxury two-story 3 bedroom, 3-bat......
Property Code: Bougainvillea House
Bedrooms: 4 | Bathrooms: 4 | Max Occupancy: 10
Location: Old Town
Pets Allowed: Yes
GARDEN OASIS~ Private!
WHEN ONLY THE BEST WILL DO... Located in the Casa Marina Area of Key West known for spacious and elegant fine homes; the Garden Oasis is no exception......
Property Code: Garden Oasis
Bedrooms: 4 | Bathrooms: 3.5 | Max Occupancy: 8
Location: Casa Marina
Pets Allowed: Yes
SOUTHERNMOST BELLE~ Grand!
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this home has a unique sense of p......
Property Code: Southernmost Belle
Bedrooms: 5 | Bathrooms: 4 | Max Occupancy: 10
Location: Key West
Pets Allowed: No
STARS & STRIPES ~ Magnificent Home In The Heart of Old Town!
ABUNDANCE IN OLD TOWN... Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring everyone together under one roof......
Property Code: Stars & Stripes
Bedrooms: 7 | Bathrooms: 4 | Max Occupancy: 20
Location: Old Town
Pets Allowed: No