Key West Rentals
From $645 per night (USD)HomeAway
"CONCH HEAVEN" ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/Heated Cocktail Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OLD TOWN LOCATION... A beautifully furnished and comfortable home, located a short distance from Duval Street. Have bik ...
From $645 per night (USD)HomeAway
From $495 per night (USD)VRBO
"CAPTAIN'S QUARTERS" ~ A Vintage Key West Retreat that is full of Charm!!
- Bedrooms:
- 3.5
- Bathrooms:
- 4
- Sleeps:
- 10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE Once you step through the threshold of this Old Town ...
From $495 per night (USD)VRBO
From $745 per night (USD)HomeAway
"SUNKISSED"~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
JUST OFF DUVAL... Private single family home with three bedrooms and three bathrooms. Open the rear French doors to a p ...
From $745 per night (USD)HomeAway
From $290 per night (USD)VRBO
Cuban Paradise- Sleeps 6 on Duval- One assigned parking space.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape the stress and cares of your daily life with a vacation to the wonderful Cuban Paradise! This roomy 2 bedroom co ...
From $290 per night (USD)VRBO
From $250 per night (USD)HomeAway
Charming Craftsman Home in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy one of the most vibrant locations that Key West has to offer. The tropics meet historic craftsman charm at this ir ...
From $250 per night (USD)HomeAway
From $650 per night (USD)VRBO
"GARDEN HIDEAWAY"~ Beautiful lush landscaped oasis located in the Casa Marina
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
PARADISE AWAITS... Newly renovation and furnished, charming home is located in one of the most desirable locations in Ke ...
From $650 per night (USD)VRBO
From $395 per night (USD)HomeAway
"MANGO MARGARITA"~ 2 bedroom/2.5 bath close to the excitement of Duval!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
LOCATION... Enjoy this convenient Old Town Location. Located a block from Duval and a short walk or bike ride to everyt ...
From $395 per night (USD)HomeAway
From $480 per night (USD)VRBO
"TIDES ON SIMONTON" ~ Perfectly located just off Duval and all the fun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ADORING COTTAGE ONE BLOCK FROM DUVAL… One bedroom cottage on Simonton Street one block from Duval. Totaling one bedroom ...
From $480 per night (USD)VRBO
From $157 per night (USD)HomeAway
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $157 per night (USD)HomeAway
From $240 per night (USD)VRBO
@@ New Ownerss many upgrades, Tropical retreat on the ocean@@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated ...
From $240 per night (USD)VRBO
From $1295 per night (USD)HomeAway
"BOOMERANG BOATHOUSE" ~ Relax in This Beautiful 4 Bedroom/4 Bath Location!
- Bedrooms:
- 3.5
- Bathrooms:
- 4
- Sleeps:
- 8
RETURN TO EQUANIMITY... “Boomerang Boathouse” is nestled in the peaceful neighborhood locals refer to as The Meadows. T ...
From $1295 per night (USD)HomeAway
From $525 per night (USD)VRBO
"STARS" ~4 bedroom, 2 Bath Condo, Pool Heat, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $525 per night (USD)VRBO
From $645 per night (USD)HomeAway
"MEMORY MAKER" ~This Property Was Featured on HGTV's show "Island Life"!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
A STYLISH CARIBBEAN SURPRISE RIGHT OFF DUVAL... Private single-family home with peaceful porches totaling two bedrooms, ...
From $645 per night (USD)HomeAway
From $680 per night (USD)VRBO
"SEAPORT SANCTUARY" ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A QUIET BUNGALOW IN THE HISTORIC SEAPORT... Private one bedroom home in the heart of Old Town. A great place for a coup ...
From $680 per night (USD)VRBO
From $550 per night (USD)HomeAway
"ISLAND TIME" ~ Fully Renovated Conch Home in a Great Old Town Location!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
EASE INTO ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pas ...
From $550 per night (USD)HomeAway
From $250 per night (USD)VRBO
"THE OLD SAPODILLA HOUSE" ~ Pet Friendly Home in Historic Bahama Village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PERFECT GETAWAY JUST STEPS FROM DUVAL... Private family home with poolside cottage totals three bedrooms and three full ...
From $250 per night (USD)VRBO
From $745 per night (USD)HomeAway
"CAPT JACK'S HIDEAWAY" ~ Vintage Conch Cottage Located on a Quiet Lane!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
QUIET LOCATION, COMFORTABLE SPACE… Located in Old Town, this home sits on a quaint little lane. With limited homes on t ...
From $745 per night (USD)HomeAway
From $745 per night (USD)VRBO
"LUNA VERDE" ~ 3 Bedroom, 2 Bath in a Quiet Neighborhood Near the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LUNA VERDE... This home is nicely situated in a quiet neighborhood just a few shorts blocks from Higgs Beach and White S ...
From $745 per night (USD)VRBO
From $1445 per night (USD)HomeAway
"MARGAUX'S HIDEAWAY"~ Extraordinary, luxury home in Old Town Key West!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ESCAPE TO THIS PEACEFUL PARADISE... "Margaux's Hideaway", is a luxury vacation rental named for its ties to the famous a ...
From $1445 per night (USD)HomeAway
From $1095 per night (USD)VRBO
"SPARROW'S LANDING" ~ Casual Sophistication Located in a Quiet Neighborhood!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
STEP INTO PARADISE... Located in the peaceful neighborhood locals call The Meadows, this home is set away from the noise ...
From $1095 per night (USD)VRBO
From $350 per night (USD)HomeAway
"SEAS THE DAY"~ Newly Built Townhome in Perfect Location with Community Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
IMMACULATE RETREAT JUST STEPS FROM IT ALL... Beautifully designed and decorated townhouse located in the Southernmost Ca ...
From $350 per night (USD)HomeAway
From $164 per night (USD)VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $164 per night (USD)VRBO
From $1455 per night (USD)HomeAway
"SEA LA VIE" ~Living in Complete Luxury in This Elegant Three Story Home!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
THREE STORY GRANDEUR… Located in the Casa Marina District in Old Town. This home is elegant, yet quite the tropical del ...
From $1455 per night (USD)HomeAway
From $250 per night (USD)VRBO
"BELLA VITA" ~2/1.5 located in the Truman Annex with a community pool!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
IDEAL LOCATION IN GREAT COMMUNITY... Enjoy your stay at the President`s Walk at Truman Annex. This well manicured commu ...
From $250 per night (USD)VRBO
From $1195 per night (USD)HomeAway
"THE SEASHELL" ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
CLASSIC KEY When only the best will do! The Seashell is the classic Old Town Key West home. Perfect setting for your dr ...
From $1195 per night (USD)HomeAway
From $745 per night (USD)VRBO
"ROYAL PALM" ~ Luxury 2 bed/ 2bath home in Old Town w/parking & private pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
HISTORIC RENOVATION OF A DARLING OLD TOWN HOUSE Enjoy Key West while staying in this historic Old Town location. Relax ...
From $745 per night (USD)VRBO
From $200 per night (USD)HomeAway
2 bedroom 2.5 bath town home in Old town Key West- Monthly Rental only
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
A CUT ABOVE II in OLD TOWN-PARK@YOUR DOOR Even though this is a 29 day rental-you can get together with friends or famil ...
From $200 per night (USD)HomeAway
From $59 per night (USD)VRBO
Key West-Coconut Beach Resort - Avail 11/14/20 to 11/21/20
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Book it before it's gone! 7 day rental - available from Saturday 11/14/20 to Saturday 11/21/20 only. Cozy and comforta ...
From $59 per night (USD)VRBO
From $125 per night (USD)HomeAway
Great Yearly Rental at 1800 Atlantic next available May 2021
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...
From $125 per night (USD)HomeAway
From $300 per night (USD)VRBO
"BEACH HOUSE"~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
PRESTIGIOUS TROPICAL RETREAT... Indulge in this spectacular two-story home situated in the premier gated community of hi ...
From $300 per night (USD)VRBO
From $150 per night (USD)HomeAway
Closer to Cuba than Walmart - Blu
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West. This nightly rental i ...
From $150 per night (USD)HomeAway
From $150 per night (USD)VRBO
CONNIE'S COTTAGE - Old-world charm and elegant tropical living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
28 Day minimum Rental: Old-world charm and elegant tropical living are waiting for you in this classic old town conch h ...
From $150 per night (USD)VRBO
From $184 per night (USD)HomeAway
Luxurious Keywest resort condominium unit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the Hyatt Windward Pointe and affords beautiful Atlantic Ocean views. This unit has two-bedrooms, 1 is a mast ...
From $184 per night (USD)HomeAway
From $140 per night (USD)VRBO
Quaint Old Town Key West Cottage with Heated Pool and Private Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Conch Escape is a 2 bedroom 2 bath cottage situated in a private gated compound of ten homes in Old Town Key West. Thes ...
From $140 per night (USD)VRBO
From $300 per night (USD)HomeAway
Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car, Great Value!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private b ...
From $300 per night (USD)HomeAway
From $200 per night (USD)VRBO
One bedroom, one bath in Old Town with off street parking- Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the White Street Gallery district, this beautiful, recently-renovated 1.5 bedroom, one bathroom condo is perf ...
From $200 per night (USD)VRBO
From $254 per night (USD)HomeAway
~CHAVEZ HOUSE~ World Class Luxury Home w/ Heated Pool In Heart of "Old Town"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About THE PROPERTY: The Historic Chavez House on Margaret Street! This 3 bedroom 2 bath two story eyebrow house was b ...
From $254 per night (USD)HomeAway
From $98 per night (USD)VRBO
MEADOWS MANOR - Monthly vacation rental with 3BD/2BA - Lovely covered porches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME TO MEADOWS MANOR! We are complying with the directives listed on the Monroe County website. Please be aware t ...
From $98 per night (USD)VRBO
From $500 per night (USD)HomeAway
Casa Margarita: Amazing Location W/ Private Pool, Huge Deck & Private Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
If you are looking for a peaceful luxury retreat that also is in the heart of Old Town Key West, Casa Margarita is the p ...
From $500 per night (USD)HomeAway
From $250 per night (USD)VRBO
CoCoMo - Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on quite Peacon Lane this one bedroom one bath new renovated cottage is your perfect Key West Hideaway. One bloc ...
From $250 per night (USD)VRBO
From $260 per night (USD)HomeAway
~ PETITE MAISON ~ Luxury Home Steps to Duval St w/ Private Parking. Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: Petite Maison is a designer Key West Guest Cottage that is located in the Gallery District of Duva ...
From $260 per night (USD)HomeAway
From $749 per night (USD)VRBO
~ CLOUD 9 ~ Perfect Home In Heart of Downtown KW w/ Heated Pool & Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
About THE PROPERTY: The Absolute Best Luxury Private Vacation Rental Home by Duval Street In Old Town. Just a half bl ...
From $749 per night (USD)VRBO
From $228 per night (USD)HomeAway
President's Lane Jewel
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This President's Lane jewel, is perfectly located on a corner lot. Unique features include a private entrance from Thoma ...
From $228 per night (USD)HomeAway
From $349 per night (USD)VRBO
"Cozy Old Key West Apartment"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This property recently fully renovated. Original house was built in 1892. 1 bedroom 1 bathroom apartment with hardwood f ...
From $349 per night (USD)VRBO
From $85 per night (USD)HomeAway
Palm Island Suite at Top Of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)HomeAway
From $180 per night (USD)VRBO
Colony Poolside: A charming bungalow near the historic cemetery
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter th ...
From $180 per night (USD)VRBO
From $200 per night (USD)HomeAway
Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes th ...
From $200 per night (USD)HomeAway
From $559 per night (USD)VRBO
Historic Seaport Luxury Home -1 Block to Duval St & Seaport Marina
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Location, Location, Location! This quintessential Key West Historic home is 4 bedroom 3.5 bathroom house is located ju ...
From $559 per night (USD)VRBO
From $240 per night (USD)HomeAway
~ Steamplant 209 ~ Luxurious Condo w/ Breathtaking Views & Rooftop Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 209! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)HomeAway
From $265 per night (USD)VRBO
Key West Gem - Large, Bright 2 BR Condo on Ocean w/ Olympic-size Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our spacious 2 Bedroom 2 Bath condo is an ideal setting for a perfect Key West vacation for up to 6 people. We have a fu ...
From $265 per night (USD)VRBO
From $500 per night (USD)HomeAway
Ohana Paradise At The Historic Seaport , Old Town. Private Home.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amaz ...
From $500 per night (USD)HomeAway
From $300 per night (USD)VRBO
Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Hidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion ...
From $300 per night (USD)VRBO
From $375 per night (USD)HomeAway
Fleming-O Quiet Retreat in the Heart of Old Town Key West Fantasy Fest Special
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Fleming-O (pronounced “Flamingo”) is located on one-way Fleming Street, only two blocks from world famous Duval Street a ...
From $375 per night (USD)HomeAway
From $160 per night (USD)VRBO
~ THE PINK HOUSE ~ Private Pool & Parking! Walk to Restaurants, Bars, Beach!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
About THE PROPERTY: The Pink House is a charming home and is not to be missed! Built in 2001, in the Classical Revival ...
From $160 per night (USD)VRBO
From $35 per night (USD)HomeAway
Hidden Beach Unit 1. The perfect place to stay in Key West for less
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hidden Beach Unit 1 - Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach ...
From $35 per night (USD)HomeAway
From $200 per night (USD)VRBO
ATLANTIC PARADISE - Overlooking the Atlantic Ocean, Amazing Pool+jacuzzi+BBQ
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time. How a ...
From $200 per night (USD)VRBO
From $500 per night (USD)HomeAway
Seaside Condo, 2 pools, close to Old Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Upon waking in the morning we hear the murmuring of tropical birds , feel the gentle sea breezes and the fragrance of j ...
From $500 per night (USD)HomeAway
From $240 per night (USD)VRBO
Old Town Harborside Luxury Key West Condo: Private Pool, Garage
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 212! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)VRBO
From $225 per night (USD)HomeAway
PACKER RETREAT - A beautifully renovated "Conch" house
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL NO CHILDREN UNDER 10 yrs of age.NO PETS Packer Retreat is a beautifully renovated "Conch" house w ...
From $225 per night (USD)HomeAway
From $158 per night (USD)VRBO
~POINCIANA GARDEN~ Updated Condo w/ Pvt Hot Tub & Parking In Perfect Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
About THE PROPERTY: Discover Poinciana Garden, an idyllic one-bedroom Key West vacation rental. Poinciana Garden is lo ...
From $158 per night (USD)VRBO
From $161 per night (USD)HomeAway
SANCTUARY ON SIMONTON - Monthly Rental in the Heart of Old Town
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM Open the door to this brand new home in the very center of Old Town Key West, and begin your perfect ex ...
From $161 per night (USD)HomeAway
From $35 per night (USD)VRBO
Oceanfront Hidden Beach Unit 2 - The best place to stay in Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlan ...
From $35 per night (USD)VRBO
From $200 per night (USD)HomeAway
~ LITTLE MISS MAGIC ~ Lovely Home w/ Sparkling Pool In PERFECT Location
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
About THE PROPERTY: "Little Miss Magic" lies in an absolutely perfect Key West location! Relax in the midst of a calm ...
From $200 per night (USD)HomeAway
From $400 per night (USD)VRBO
Luxury Galleon Resort & Marina 2 Bed/2 Bath Marina View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
From $400 per night (USD)VRBO
From $250 per night (USD)HomeAway
Family House- Two K bedrooms, 1.5 baths, Pvt.Spa in Garden Setting-Shared Pools!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 6
This two-story 1880's Cigar Maker's Cottage has been completely renovated and has a living room with 42' flat screen TV/ ...
From $250 per night (USD)HomeAway
From $183 per night (USD)VRBO
Cottage Charm Old Town Monthly Rental- Summer Special
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Your own private paradise awaits in this peaceful district just a few streets away from the buzz of Duval Street. The co ...
From $183 per night (USD)VRBO
From $225 per night (USD)HomeAway
Reynolds Retreat - A Great Monthly Getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Reynolds Retreat is quintessential Key West living. Located just a few blocks off Duval Street, ...
From $225 per night (USD)HomeAway
From $240 per night (USD)VRBO
Cockadoodle Cottage on Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West cottage architecture has been thoroughly "time-tested" in "island life and culture" in this somewhat infamous l ...
From $240 per night (USD)VRBO
From $178 per night (USD)HomeAway
La Casita
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful, fully furnished 2BD/2BA single family home is located in the prestigious Casa Marina neighborhood. Speci ...
From $178 per night (USD)HomeAway
From $170 per night (USD)VRBO
~ CAYO LIMÒN ~ Cute Home In Perfect Location w/ Parking & Heated Pool
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
About THE PROPERTY: Experience local living in the heart of it all! Cayo Limon - an absolutely amazing Key West home - ...
From $170 per night (USD)VRBO
From $450 per night (USD)HomeAway
Absolutely Paradise- A Tropical Getaway In Old Town
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 8
Absolutely Paradise ---This newly redecorated town home is the perfect place to enjoy the tranquility of an island vaca ...
From $450 per night (USD)HomeAway
From $1000 per night (USD)VRBO
~DREAMING ON DUVAL~ Luxury 5 Bed, 4.5 Bath & Private Pool- As seen on HGTV
- Bedrooms:
- 5.5
- Bathrooms:
- 5
- Sleeps:
- 12
Want to be close to the lively atmosphere of Duval but need the privacy of a place you could call home? Look no further, ...
From $1000 per night (USD)VRBO
From $634 per night (USD)HomeAway
Tropical~Tranquility
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Extraordinarily secluded and completely hidden from view on a sleepy artist’s lane is a special slice of Key West you wo ...
From $634 per night (USD)HomeAway
From $175 per night (USD)VRBO
TRANQUILITY - Quaint Cottage in Gated Compound with Shared Pool + Private BBQ
- Bedrooms:
- 2.5
- Bathrooms:
- 1
- Sleeps:
- 4
Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything yo ...
From $175 per night (USD)VRBO
From $214 per night (USD)HomeAway
Renovated Corner Unit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This Beautiful one bedroom one bathroom condo was formerly a two bedroom opened up to create a spacious living area. The ...
From $214 per night (USD)HomeAway
From $158 per night (USD)VRBO
~ POINCIANA TREETOP ~ Updated Suite w/ Private Parking In Great Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
About THE PROPERTY: Welcome to Poinciana Treetop, a sunny one-bedroom Key West vacation rental. The casual upstairs un ...
From $158 per night (USD)VRBO
From $45 per night (USD)HomeAway
Truman Annex Best Location in Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We stick to a Saturday check in during the in season months (Jan-April) Greetings from Paradise, where the temperature ...
From $45 per night (USD)HomeAway
From $370 per night (USD)VRBO
Key West Spa Villa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, ...
From $370 per night (USD)VRBO
From $103 per night (USD)HomeAway
Great location! Everything one would need. 3 month minimum
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
This quiet, lovely tropical cottage has lots of privacy where guests enjoy a small pond with a waterfall as well as a ga ...
From $103 per night (USD)HomeAway
From $275 per night (USD)VRBO
Butterfly Garden Flat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Completely hidden from the street, this authentic Butterfly Garden Flat, provides you with two private entrances off a l ...
From $275 per night (USD)VRBO
From $185 per night (USD)HomeAway
Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located only two miles from Duval 1800 Atlantic Blvd offers the best of both worlds; close to downtown without most of t ...
From $185 per night (USD)HomeAway
From $75 per night (USD)VRBO
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880's that was converted into indi ...
From $75 per night (USD)VRBO
From $874 per night (USD)HomeAway
Architects Cottage in fantastic Old Town location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
We have a wonderful MONTHLY rental to offer you: an historic 'conch' house has been completely redesigned and custom cra ...
From $874 per night (USD)HomeAway
From $370 per night (USD)VRBO
Villa Nouveau Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sometimes a Key West cottage that at first glance appears predictable from the outside, is full of abundant surprises wh ...
From $370 per night (USD)VRBO
From $279 per night (USD)HomeAway
Craig & Cindy Key West 3 Bedroom Waterfront Beachside Resort Condo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Our luxurious condo is part of the brand new spectacular Beachside Resort & Conference Center. Beachside is Key West an ...
From $279 per night (USD)HomeAway
From $359 per night (USD)VRBO
Exclusive Key West Beach Front
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Rare, one-of-a kind designer luxury condominium located in an exclusive gated Key West beachfront property. The Exclusiv ...
From $359 per night (USD)VRBO
From $240 per night (USD)HomeAway
Duval Square Retreat: A beautiful condo steps from the action
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and quieter end of Duval ...
From $240 per night (USD)HomeAway
From $144 per night (USD)VRBO
~ INN COGNEATO COTTAGE ~ Gorgeous Home w/Pool in the <3 of Key West. Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
About THE PROPERTY: Inn Cogneato is a newly renovated beautiful 2 bedroom 2 bath home located in one of the oldest par ...
From $144 per night (USD)VRBO
From $100 per night (USD)HomeAway
Sunset Suite - Gated Compound 1/2 Block Off Duval St. - Private spa!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Overlooking the gardens and 3 fountains, in a gated 5-unit compound, the entrance to our spacious Sunset Suite is throug ...
From $100 per night (USD)HomeAway
From $180 per night (USD)VRBO
BAHAMIAN REED Spacious Private Home, Shared Pool, Truman Annex, Close to All
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back ...
From $180 per night (USD)VRBO
From $190 per night (USD)HomeAway
~CASA KEY WEST~ Historical Home w/ Plunge Pool In PERFECT Location.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
About THE PROPERTY: As seen on HGTV's television series "ISLAND LIFE"! One of the Grand Dames of Key West, this two-s ...
From $190 per night (USD)HomeAway
From $175 per night (USD)VRBO
BOOK NOW FOR JAN FEB MAR 2021! Discount! Cancellation full refund 90 days prior.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Complex The Truman Annex is truly one of a kind in Key West. It is a gated community with impeccably kept grounds. ...
From $175 per night (USD)VRBO
From $600 per night (USD)HomeAway
4 Bed/4 Bath Retreat at the End of the Road
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located at the end of the Florida Keys connected by road, Key West is both an oasis of calm and the launching pad for an ...
From $600 per night (USD)HomeAway
From $550 per night (USD)VRBO
Louisa House: A comfortable four bedroom vacation hideaway
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southe ...
From $550 per night (USD)VRBO
From $400 per night (USD)HomeAway
Beach Club #408 - Unique Oceanfront living
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shore ...
From $400 per night (USD)HomeAway
From $79 per night (USD)VRBO
Alegre In Fabulous Key West Awaits - Free Bikes, Wifi & Parking
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Weekly And Long-term Rentals Located in picturesque Truman Annex in fabulous, sunny Key West, Alegre is close to all th ...
From $79 per night (USD)VRBO
From $150 per night (USD)HomeAway
Truman Annex, two blocks from Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful ...
From $150 per night (USD)HomeAway
From $225 per night (USD)VRBO
Ashe Splashe: A beautiful restoration of a historic Key West property
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL From the owners of South of Frances, here is another beautiful, historic restoration project. Th ...
From $225 per night (USD)VRBO
From $329 per night (USD)HomeAway
KW GULF FRONT/Gulf view Home with dock and pool.
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
On the entire island of Key West there are fewer than 50 private homes on open water and only a few with their own priva ...
From $329 per night (USD)HomeAway
From $325 per night (USD)VRBO
Sunshine Dream- Monthly Rental the first of the month to the end of the month.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunshine Dreams is a historic conch cottage located on a quiet lane in the center of Old Town. This one bedroom, one bat ...
From $325 per night (USD)VRBO
From $250 per night (USD)HomeAway
KEY WEST FOUND Historic Truman Annex, Downtown, Walk to Duval, Shared Pool
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true! Located in the his ...
From $250 per night (USD)HomeAway
From $300 per night (USD)VRBO
Starfish Monthly Rental 2 blocks from Duval street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This spacious 2 bedroom, 2 bath shotgun style home is your ideal Key West Vacation Home away from home. Walk down the hu ...
From $300 per night (USD)VRBO
From $125 per night (USD)HomeAway
Direct Ocean View from Your Condo-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom ...
From $125 per night (USD)HomeAway
From $250 per night (USD)VRBO
"Coconut Cabana" Old Town Tropical Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
An Old town Key West home, located in the Historic District and just one half a block off of world famous Duval Street. ...
From $250 per night (USD)VRBO
From $165 per night (USD)HomeAway
Colony Sunset- Bright and airy cottage in the heart of old town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in The Colony, a secluded compound just steps from Duval Street, Colony Sunset is a colorful and relaxing retrea ...
From $165 per night (USD)HomeAway
From $700 per night (USD)VRBO
Classic Key West Estate
- Bedrooms:
- 6.5
- Bathrooms:
- 7
- Sleeps:
- 14
Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation re ...
From $700 per night (USD)VRBO
From $240 per night (USD)HomeAway
~ STEAMPLANT 208 ~ Luxurious Condo w/ Breathtaking Views & Rooftop Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 208! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)HomeAway
From $160 per night (USD)VRBO
Sparkling clean Key West Family Home. Free Parking and WiFi
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated commun ...
From $160 per night (USD)VRBO
From $450 per night (USD)HomeAway
Hyatt Sunset Harbor Resort for ONLY Sunday to Sunday Week's stay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is for A WEEK'S Stay Only. Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant ...
From $450 per night (USD)HomeAway
From $475 per night (USD)VRBO
Royal Escape- 3BR/3BA, W/ Private Pool In Casa Marina Area-
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
If Cleopatra and Anthony had dreamed of a Key West hideaway this spacious three bedroom, three bath “Royal Escape” would ...
From $475 per night (USD)VRBO
From $260 per night (USD)HomeAway
Hidden Treasure-Pet-friendly, Close to Duval St., Outdoor Deck, Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find ...
From $260 per night (USD)HomeAway
From $160 per night (USD)VRBO
BAYVIEW HARBOR Large Outdoor Patio, Shared Pool, Walk to Duval Street+More
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for a peaceful retreat yet close to everything? Ideally located on Southard Street, within walking distance to ...
From $160 per night (USD)VRBO
From $230 per night (USD)HomeAway
Luxury and Spacious Condo on Duval Steet
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
We know that you will enjoy staying in this oasis of comfort in the paradise of Key West. Our Cuban Club Condo is a 1500 ...
From $230 per night (USD)HomeAway
From $215 per night (USD)VRBO
Conch Wind Private Condo, Shared Pool, Gated Community, Nestled in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stop searching, Conch Wind is the rental home in Key West you have been hunting for! This two story Conch Style town ho ...
From $215 per night (USD)VRBO
From $571 per night (USD)HomeAway
*** PRICE REDUCTION *** Penthouse Suite KW Galleon Resort, Avail 7/6-7/10/2021
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The Galleon Resort is the best location in Key West. We own week 26 and 27, so for 2021, that is from Saturday, June 26 ...
From $571 per night (USD)HomeAway
From $142 per night (USD)VRBO
~ SOLARIS COTTAGE ~ Enjoy Old Town Livin'. Dog friendly home!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
About THE PROPERTY: Welcome to Solaris Cottage, located on one of Key West’s most private slow lanes. This tranquil on ...
From $142 per night (USD)VRBO
From $275 per night (USD)HomeAway
A spacious "Penthouse" condo at The Banyan
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just steps from Duval Street, this secluded resort appears off the beaten path, yet is truly situated a stone's throw fr ...
From $275 per night (USD)HomeAway
From $85 per night (USD)VRBO
Nautical Keys Suite at Top Of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)VRBO
From $250 per night (USD)HomeAway
PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Open the door to Paradise Place and find yourself transported to a peaceful sanctuary. The downstairs living area is ...
From $250 per night (USD)HomeAway
From $232 per night (USD)VRBO
~ MARGARET TRUMAN SUITE ~ Updated Suite w/ Shared Pool In Perfect Location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
About THE PROPERTY: The Margaret Truman Suite is steps from Duval Street, the Lighthouse, Southernmost Point, the Hemi ...
From $232 per night (USD)VRBO
From $259 per night (USD)HomeAway
PET FRIENDLY! 3 Bedroom 3 bathroom home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
"FlipFlop Inn" is a beautiful 3 Bedroom 3 Bath home(each bedroom has its own private full bath), located in the luxu ...
From $259 per night (USD)HomeAway
From $195 per night (USD)VRBO
SOUTHARD GETAWAY Private Home, Family friendly, Shared Pool, Walk to All!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Imag ...
From $195 per night (USD)VRBO
From $375 per night (USD)HomeAway
Mango Cottage- 2BR/2BA Family-Friendly Old Town Private Home with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mango Cottage This recently-restored historic Conch house is an excellent vacation home. The kitchen and bathrooms have ...
From $375 per night (USD)HomeAway
From $200 per night (USD)VRBO
PAPAYA PLACE - Stunning Setting Overlooking the Atlantic Ocean, Pool+Jacuzzi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Atlantic Ocean is just at your reach when staying at Papaya Place! You can almost hear the waves of the ocean! This gre ...
From $200 per night (USD)VRBO
From $100 per night (USD)HomeAway
Harrison's Hideaway - Cottage, Pvt. Spa - 2 Shared Pools - Steps from Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Part of 4 exclusive units at Abbey Road, this free standing historic Cigar Maker's cottage is at 918-920 Center Street. ...
From $100 per night (USD)HomeAway
From $175 per night (USD)VRBO
Island Style- Pet-friendly Cottage 2 1/2 block off Duval- Shared pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Style---Resort style accommodations at an affordable price! Nestled among a colony of freestanding Conch style co ...
From $175 per night (USD)VRBO
From $225 per night (USD)HomeAway
A PLACE IN PARADISE Spacious, Private Home, Shared Pool, Walk to Everything!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE! You will experience true Key West liv ...
From $225 per night (USD)HomeAway
From $600 per night (USD)VRBO
Flirty Flamingo Key West
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $600 per night (USD)VRBO
From $100 per night (USD)HomeAway
McCartney's Manor- Luxury Private Cottage, Courtyard and Hot Tub!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Part of 4 exclusive units at Abbey Road, McCartney's Manor is in a private, gated compound. The state-of-the-art kitche ...
From $100 per night (USD)HomeAway
From $70 per night (USD)VRBO
Heart of Old Town, Truman Anx PRIVATE END UNIT 2BR king/twin/queen, Pool Grd FL
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
TRUMAN ANNEX: The ROOSTER RETREAT is a lovely 2 bedroom, (1 king/2 twins, and queen bed) 1 remodeled bathroom. Bright E ...
From $70 per night (USD)VRBO
From $300 per night (USD)HomeAway
Award Winning Home Next to Lighthouse! Newly Updated Private Pool, Gated Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This licensed vacation home was recently featured on Key West's 2017 historic home tour and is available to rent monthly ...
From $300 per night (USD)HomeAway
From $70 per night (USD)VRBO
The Galleria~Unit #11 Bikes & New Pool! Located in Bahama Village!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
The Galleria #11 – A Hidden Gem on Howe Street! small and no frills but affordable for Key West! recently renovate ...
From $70 per night (USD)VRBO
From $275 per night (USD)HomeAway
Abbey Road-Great for large group-Shared Pools-1/2 block from Duval Street!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Abbey Road - Gated Compound, Sleeps up to 12! Daily Housekeeping! Including Lennon's Lodge (Sleeps 6 with 8 person hot ...
From $275 per night (USD)HomeAway
From $250 per night (USD)VRBO
Casa De Cuba a Beach House - Cuban Flair Steps from Duval
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Location! Style! Elegance! This restored "beach" home is fabulous combination of everything a great vacation property sh ...
From $250 per night (USD)VRBO
From $118 per night (USD)HomeAway
SUITE CAROLINE - Luxury condo within steps to Key West's historic seaport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
28 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully res ...
From $118 per night (USD)HomeAway
From $523 per night (USD)VRBO
Tucked away near the Southernmost Point, Louisa's Hideaway is it!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. ...
From $523 per night (USD)VRBO
From $467 per night (USD)HomeAway
**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $467 per night (USD)HomeAway
From $59 per night (USD)VRBO
The Galleon Resort Best Resort Location in KW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This October condo is a 2BR, 2BA sunset/pool view sleeps 6. Condo has a full modern kitchen with granite/stainless, di ...
From $59 per night (USD)VRBO
From $357 per night (USD)HomeAway
Waterfront Luxury Home with private pool in exclusive Key Cove Landings!
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $357 per night (USD)HomeAway
From $322 per night (USD)VRBO
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $322 per night (USD)VRBO
From $207 per night (USD)HomeAway
Almost Paradise @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $207 per night (USD)HomeAway
From $614 per night (USD)VRBO
Catch of the Day @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
View passing ships and sunsets from your own deck or balcony in the Truman Annex's most prestigious building, the former ...
From $614 per night (USD)VRBO
From $400 per night (USD)HomeAway
3 bd Condo w/ boat slip Pelican Landing St Kitts
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $400 per night (USD)HomeAway
From $279 per night (USD)VRBO
Amberjack @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $279 per night (USD)VRBO
From $294 per night (USD)HomeAway
**CIELO AZUL @ THE BEACH CLUB** Oceanfront Condo / Pools + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $294 per night (USD)HomeAway
From $446 per night (USD)VRBO
**THE POLYNESIAN HOUSE @ CASA MARINA** Estate & Huge Pool + LAST KEY SERVICES...
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $446 per night (USD)VRBO
From $150 per night (USD)HomeAway
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen w ...
From $150 per night (USD)HomeAway
From $338 per night (USD)VRBO
ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
WELCOME TO ISLAND TIME! We are complying with the directives listed on the Monroe County website. Please be aware tha ...
From $338 per night (USD)VRBO
From $185 per night (USD)HomeAway
Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located only two miles from Duval 1800 Atlantic Blvd offers the best of both worlds; close to downtown without most of t ...
From $185 per night (USD)HomeAway
From $436 per night (USD)VRBO
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $436 per night (USD)VRBO
From $171 per night (USD)HomeAway
Sand Crab Cabana @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $171 per night (USD)HomeAway