Fleming Key Rentals
From $159 per night (USD)VRBO
Conch Republic House - Key West Millionaires Row
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
In the center of Key West's prestigious "Millionaires Row," Conch Republic House is a tranquil getaway for up to six in ...
From $159 per night (USD)VRBO
From $345 per night (USD)VRBO
little bodega in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Very nice 1 br/bath house on Solaris Hill centered 2 blks off Duvall St. in Old Town Key West. Enjoy bustling Duvall wi ...
From $345 per night (USD)VRBO
From $539 per night (USD)VRBO
**MODERN IN THE MEADOWS @ THE MEADOWS** Chic Private Home & Pool + LAST KEY SERV
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN IN THE ...
From $539 per night (USD)VRBO
From $783 per night (USD)VRBO
Newly Renovated Luxury Coastal Home in the Heart of Old Town Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to La Margarita, a newly renovated home with coastal charm only blocks away from Duval Street, the Historic Seap ...
From $783 per night (USD)VRBO
From $1253 per night (USD)VRBO
Tropical Tranquility - 4BR Luxury Villa In Old Town Key West w Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town ...
From $1253 per night (USD)VRBO
From $2186 per night (USD)Expedia
Key West Suites Hotel # 205
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used t ...
From $2186 per night (USD)Expedia
From $1738 per night (USD)VRBO
Key West Suites Hotel #201 on Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $1738 per night (USD)VRBO
From $425 per night (USD)VRBO
Charming Old Town Bungalow
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Charming two story, 3 Bedroom 3 Bathroom. Renovated home built in 1908, on a corner lot in Historical Old Town Key West. ...
From $425 per night (USD)VRBO
From $1200 per night (USD)VRBO
Secret Villa I @ Old Town with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa I - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own priv ...
From $1200 per night (USD)VRBO
From $528 per night (USD)Expedia
SERENDIPITY ~ Grand 4 Bedroom/4.5 Bathroom Home in Heart of Key West!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
TIME TO CREATE LIFELONG MEMORIES… Your long-awaited island retreat is sure to have all expectations exceeded within this ...
From $528 per night (USD)Expedia
From $1082 per night (USD)VRBO
3-Story spacious conch style home w/ private pool & dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
"Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropicall ...
From $1082 per night (USD)VRBO
From $363 per night (USD)VRBO
\"Island Time\" in Old Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Island Time" located in the heart of Old Town! This 2nd floor condo is perfect home base for your adventure ...
From $363 per night (USD)VRBO
From $373 per night (USD)VRBO
Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Single family home. (Not a condo.) We welcome kids, pets, partners, friends. Free off street parking for 2-3 vehicles. ...
From $373 per night (USD)VRBO
From $347 per night (USD)Expedia
Carriage House at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $347 per night (USD)Expedia
From $336 per night (USD)VRBO
Bunk Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $336 per night (USD)VRBO
From $235 per night (USD)Expedia
Old Town Key West classic with private saltwater pool & enclosed patio- by shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Petronia Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $235 per night (USD)Expedia
From $416 per night (USD)VRBO
TROPICAL PROPERTIES VACATION RENTAL-KEY WEST
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
****This property requires a minimum stay of 28 nights in the same calendar month**** Tropical Properties Vacation Rent ...
From $416 per night (USD)VRBO
From $669 per night (USD)Expedia
Luxury Waterfront at Galion Resort in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $669 per night (USD)Expedia
From $1428 per night (USD)VRBO
~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Villa Josine not only has curb appeal but also is a stunning example of a Key West eyebrow house. This arc ...
From $1428 per night (USD)VRBO
From $1148 per night (USD)Expedia
Secret Villa II @ Old Town: with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...
From $1148 per night (USD)Expedia
From $363 per night (USD)VRBO
Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Dade County pine house has a strong connection to the sea. It was built in 1910 by ship's carpenters and owned for ...
From $363 per night (USD)VRBO
From $2584 per night (USD)Expedia
Private Heated Pool & Near Duval - The Curry House
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 18
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $2584 per night (USD)Expedia
From $285 per night (USD)VRBO
Balcony, Pool, & Near Duval - Curry House Room 6
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Curry House offers three stories of historic Conch house charm, perfect for your getaway. This guesthouse featu ...
From $285 per night (USD)VRBO
From $389 per night (USD)Expedia
Balcony, Pool, Near Duval - Curry House Room 3 + 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Curry House offers three stories of historic charm, transporting you back in time. The guesthouse features priv ...
From $389 per night (USD)Expedia
From $285 per night (USD)VRBO
Balcony, Pool, & Near Duval - Curry House Room 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guesth ...
From $285 per night (USD)VRBO
From $280 per night (USD)Expedia
Balcony, Pool, & Near Duval - Curry House Room 8
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $280 per night (USD)Expedia
From $280 per night (USD)VRBO
Balcony, Pool, & Near Duval - Curry House Room 7
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $280 per night (USD)VRBO
From $290 per night (USD)Expedia
Balcony, Pool, & Near Duval - Curry House Room 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $290 per night (USD)Expedia
From $284 per night (USD)VRBO
Balcony, Pool, & Near Duval - Curry House Room 9
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $284 per night (USD)VRBO
From $285 per night (USD)Expedia
Curry House | Heated Pool, King Bed, 1st Floor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $285 per night (USD)Expedia
From $632 per night (USD)VRBO
Private Parking, Heated Pool - Sweet Caroline
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $632 per night (USD)VRBO
From $349 per night (USD)Expedia
Private Parking , Heated Pool - Key Lime Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $349 per night (USD)Expedia
From $349 per night (USD)VRBO
Heated Pool, Epic Location - Sugar Pie Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $349 per night (USD)VRBO
From $349 per night (USD)Expedia
Heated Pool, Epic Location - Honeybun Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $349 per night (USD)Expedia
From $395 per night (USD)VRBO
Private Parking, Heated Pool - Banana Split
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $395 per night (USD)VRBO
From $354 per night (USD)Expedia
Heated Pool, Private Parking - Creme Brulee Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $354 per night (USD)Expedia
From $619 per night (USD)VRBO
Luxury Waterfront Stay @ The Galleon, Mins from Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine waking up every morning in Paradise. With Balconies that overlook the marina and ocean. Private marina, private ...
From $619 per night (USD)VRBO
From $2695 per night (USD)VRBO
CLASSIC KEY WEST - Grand home in Old Town location
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
The Mansion, circa 1840’s is a lovingly restored and renovated three story Classic Folk Victorian home with seven bedroo ...
From $2695 per night (USD)VRBO
From $1115 per night (USD)VRBO
PERFECTION...STEPS FROM DUVAL ~
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The Villa is a newer built poolside home, situated steps away from famous Duval Street, the historic seaport and everyth ...
From $1115 per night (USD)VRBO
From $551 per night (USD)Expedia
New Listing- Modern & spacious historic home with private pool and parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover paradise at Brisa Azul (Blue Breeze), an exquisite historic home nestled in the heart of Old Town Key West. Thi ...
From $551 per night (USD)Expedia
From $3705 per night (USD)VRBO
WATSON HOUSE GRAND ESTATE on Simonton St
- Bedrooms:
- 11
- Bathrooms:
- 11
- Sleeps:
- 22
The Grand Estate is comprised of the Mansion and the Villa offering 11 bedrooms and baths. It is ideal for family gather ...
From $3705 per night (USD)VRBO
From $686 per night (USD)Expedia
Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the m ...
From $686 per night (USD)Expedia
From $334 per night (USD)VRBO
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You don’t oft ...
From $334 per night (USD)VRBO
From $520 per night (USD)Expedia
CROOKED PALM ~ 3 Bedroom, 3 Bathroom Luxury Home w/ Pool & Compact Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
LET THE REAL WORLD SLIP AWAY... Experience quintessential island serenity within this charming and newly renovated home ...
From $520 per night (USD)Expedia
From $788 per night (USD)VRBO
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $788 per night (USD)VRBO
From $534 per night (USD)VRBO
The Galleon Resort Best Resort Location in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $534 per night (USD)VRBO
From $304 per night (USD)VRBO
Anchors Away - Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Anchors Away offers traditional Conch style living and is located in the coveted Old Town Key West. This home is unbeata ...
From $304 per night (USD)VRBO
From $336 per night (USD)Expedia
Red Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $336 per night (USD)Expedia
From $717 per night (USD)VRBO
**SOUTHERNMOST BLISS @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERNMOST ...
From $717 per night (USD)VRBO
From $242 per night (USD)VRBO
ESCAPE ON FLEMING - A charming 2 bedroom home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM RENTAL ... This property is not allowed to accept pets. Break away from it all at Escape on Fleming. Thi ...
From $242 per night (USD)VRBO
From $424 per night (USD)VRBO
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Heated/Chilled Pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $424 per night (USD)VRBO
From $549 per night (USD)VRBO
Incredible 2BR Penthouse condo on Front Street with amazing amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...
From $549 per night (USD)VRBO
From $386 per night (USD)VRBO
QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
YOUR PIECE OF PARADISE… Residing in an attractive neighborhood at the highest point of Key West referred to as “Solares ...
From $386 per night (USD)VRBO
From $167 per night (USD)Expedia
NEWTON'S NEST ~ Adult Only, 1 Bedroom, 1 Bath Condo w/ Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
SIMPLISTIC ELEGANCE... Enjoy easy tropical living in this quiet refuge located within Old Town where you can roost and i ...
From $167 per night (USD)Expedia
From $394 per night (USD)VRBO
Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 story Townhouse is in "Old Town Villas". A Caribbean inspired community in the heart of Key West. Built in 2017. ...
From $394 per night (USD)VRBO
From $1299 per night (USD)Expedia
Oversized home for the whole family w/private pool & dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1299 per night (USD)Expedia
From $574 per night (USD)VRBO
Old Town 4 /4.5 house with private pool and 2 poolside cottages + outdoor shower
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Newly restored Key West property in old town. Blocks from Duval and the harbor. Private heated pool central AC washer dr ...
From $574 per night (USD)VRBO
From $1082 per night (USD)Expedia
Spacious home with pool & balcony - 1 block from Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Last Minute Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $1082 per night (USD)Expedia
From $900 per night (USD)VRBO
Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 9 - Nov 16
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Two story townhouse with two bedrooms, pull out couch, full kitchen, three bathrooms. Overlooking the harbor with full ...
From $900 per night (USD)VRBO
From $613 per night (USD)VRBO
Charming 3 bedroom blocks from Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming Conch Style home on Southard street is just a few blocks from Duval St and across from the old Harris Scho ...
From $613 per night (USD)VRBO
From $516 per night (USD)VRBO
Elizabeth Retreat: A three bedroom historic home in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just ...
From $516 per night (USD)VRBO
From $821 per night (USD)Expedia
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $821 per night (USD)Expedia
From $318 per night (USD)VRBO
Ashe Splashe: A beautiful restoration of a historic Key West property
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
28 DAY MINIMUM RENTAL From the owners of South of Frances, here is another beautiful, historic restoration project. Th ...
From $318 per night (USD)VRBO
From $239 per night (USD)Expedia
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
**This accommodation lies up a set of narrow, spiral stairs to a gorgeous room with dramatic, dormered ceilings within t ...
From $239 per night (USD)Expedia
From $235 per night (USD)VRBO
FUENTE ~ Adults Only, Spacious Poolview King Suite at Azul Mansion!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A DREAMY ESCAPE... Create your very own Key West story within the captivating, adults only Azul Queen Anne mansion which ...
From $235 per night (USD)VRBO
From $238 per night (USD)Expedia
CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
ISLAND SANCTUARY... The grand and adults only Azul Queen Anne mansion awaits the creation of your tropical sabbatical wi ...
From $238 per night (USD)Expedia
From $235 per night (USD)VRBO
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
PERFECT RECIPE FOR RELAXATION... Make the most of your island sabbatical within the exquisite and adults only Azul Queen ...
From $235 per night (USD)VRBO
From $244 per night (USD)Expedia
CLARO ~ Adults Only, Pool View King Room in Azul Mansion!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A WORLD APART FROM REALITY... Indulge in this tropical retreat that possesses all the desirable amenities to make the mo ...
From $244 per night (USD)Expedia
From $230 per night (USD)VRBO
FONTANA ~ Adults Only, Pool Access King Room at Azul Mansion!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
ISLAND SANCTUARY... Step up to the elegant, adults only Azul Queen Anne mansion for your dreamy island retreat. Built in ...
From $230 per night (USD)VRBO
From $231 per night (USD)Expedia
AMBROSIA ~ Adults Only, Poolside King Room in Azul Mansion!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
YOUR SOUTHERN SANCTUARY... Step foot inside the historic and adults only Azul Queen Anne mansion ready to capture your i ...
From $231 per night (USD)Expedia
From $234 per night (USD)VRBO
CORTEZ ~ Adults Only, Poolview King Room at Azul Mansion!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
FIND YOUR ZEN... The historic and charming Azul Queen Anne mansion sets the tone of your serene adults only retreat. Mar ...
From $234 per night (USD)VRBO
From $230 per night (USD)Expedia
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
ELEGANT ISLAND RETREAT... Awaken your tropical senses in this incredible, adults only retreat located within the histori ...
From $230 per night (USD)Expedia
From $245 per night (USD)VRBO
FLOR DE CANA ~ Adults Only, Poolview Queen Room at Azul Mansion!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
YOUR SOUTHERN SANCTUARY... Conveniently residing in the historic Old Town district of Key West, the dreamy and adults on ...
From $245 per night (USD)VRBO
From $234 per night (USD)Expedia
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
RELAX, UNWIND & ESCAPE... Immerse yourself within the charming, adults only Azul Queen Anne mansion built in 1899 by shi ...
From $234 per night (USD)Expedia
From $468 per night (USD)VRBO
Steps from Duval, Shared Pool – Sky Loft Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duv ...
From $468 per night (USD)VRBO
Click For PricingExpedia
The Queens Villa
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Former Fantasy Fest Queens private residence. I also own the number one hotel in Key West. Best location at the END of ...
Click For PricingExpedia
From $373 per night (USD)VRBO
CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Description: Welcome to Corazon, a stunning 2-bedroom vacation rental in the heart of Key West's Old Town neighborhood. ...
From $373 per night (USD)VRBO
From $3155 per night (USD)Expedia
Takeover at the Grand Maloney
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: The Grand Maloney Hotel is a boutique hotel located in the heart of downtown Key West. Our signature red brick, ...
From $3155 per night (USD)Expedia
From $1068 per night (USD)VRBO
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $1068 per night (USD)VRBO
From $192 per night (USD)VRBO
Cottage in Old Town Key West w/ Pool, Parking and Privacy. One block from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Down a hidden lane in the heart of Old Town Key West you will find Loco Court Cottages.The compound is located one block ...
From $192 per night (USD)VRBO
From $256 per night (USD)VRBO
Cottage in Old Town Key West w/ Pool, Parking and Privacy. One block from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Down a hidden lane in the heart of Old Town Key West you will find Loco Court Cottages.The compound is located one block ...
From $256 per night (USD)VRBO
From $368 per night (USD)VRBO
NEW LISTING 2nd Fl Condo w/private outdoor deck overlooking historic Fleming St.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Airy sun-filled apartment above an art gallery in 100 year old Old Town Conch home. Private cozy quiet & romantic hideaw ...
From $368 per night (USD)VRBO
From $926 per night (USD)VRBO
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Key West Wabi Sabi is a quintessential 1930s cottage that embodies the beauty and simplicity of island-life charm. If yo ...
From $926 per night (USD)VRBO
From $2172 per night (USD)Expedia
Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation re ...
From $2172 per night (USD)Expedia
From $1110 per night (USD)VRBO
Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a ha ...
From $1110 per night (USD)VRBO
From $1996 per night (USD)Expedia
Features.Key West Suites Hotel has an outdoor pool and fitness center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used ...
From $1996 per night (USD)Expedia
From $228 per night (USD)VRBO
SEA-NIC VIEW ~ 2 BR/2Ba Water-front views, Heated Pool Access and Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
IT'S A SWELL LIFE… Endless island treasures engulf this oceanfront haven which is your one stop destination for a comple ...
From $228 per night (USD)VRBO
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Beautiful views and close to Duval Street festivities and boat docks. Wks 29-30.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
Click For PricingExpedia
From $179 per night (USD)VRBO
Pearl in Paradise-Charming 2bed 2bath Old Town home w/ shared pool, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $179 per night (USD)VRBO
From $557 per night (USD)VRBO
Antigua Retreat- 2BR 2BA waterfront condo w/ pool & boat slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $557 per night (USD)VRBO
From $513 per night (USD)VRBO
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $513 per night (USD)VRBO
From $448 per night (USD)VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $448 per night (USD)VRBO
From $636 per night (USD)VRBO
~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are ...
From $636 per night (USD)VRBO
From $291 per night (USD)Expedia
Deluxe Queen & Pet Friendly - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $291 per night (USD)Expedia
From $291 per night (USD)VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $291 per night (USD)VRBO
From $291 per night (USD)Expedia
Deluxe Queen & Pet Friendly - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $291 per night (USD)Expedia
From $291 per night (USD)VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $291 per night (USD)VRBO
From $288 per night (USD)Expedia
Classic King & Private Balcony - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $288 per night (USD)Expedia
From $291 per night (USD)VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $291 per night (USD)VRBO
From $282 per night (USD)Expedia
Classic King, Pool - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $282 per night (USD)Expedia