Fleming Key Rentals
From $1573 per night (USD)VRBO
Relax in Style at Windsor Townhomes #4
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $1573 per night (USD)VRBO
From $2001 per night (USD)VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $2001 per night (USD)VRBO
From $605 per night (USD)VRBO
Escape to \"Casa Escondida\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the enchanting "Casa Escondida," a historic Conch Style home with a modern twist, nestled on a tranquil, seclu ...
From $605 per night (USD)VRBO
From $478 per night (USD)VRBO
The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Hideout, where luxury meets location. Look no further than "The Hideout" for upscale luxury and single- ...
From $478 per night (USD)VRBO
From $1614 per night (USD)VRBO
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1614 per night (USD)VRBO
From $1708 per night (USD)VRBO
Spacious Townhome on Windsor Lane 3\/3.5
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has ...
From $1708 per night (USD)VRBO
From $284 per night (USD)VRBO
ANNA MARIA HAVEN - Renovated 3bd\/3ba Conch Monthly rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This newly remodeled Conch house is located on Olivia Street in Old Town Key West just two and a half blocks from World ...
From $284 per night (USD)VRBO
From $1696 per night (USD)VRBO
Windsor Townhomes #6 - Large pool 3B\/3.5 bath, 3 blocks to Duval
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $1696 per night (USD)VRBO
From $948 per night (USD)VRBO
Spacious 2\/2 Waterfront Condo w\/Pool&Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip a ...
From $948 per night (USD)VRBO
From $250 per night (USD)Expedia
Charming + Circa 1889 Historic Eyebrow Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 Night Minimum. Welcome to "The Saltbox"! Featured in design magazines. 710 Ashe Street is a charming house circa 18 ...
From $250 per night (USD)Expedia
From $159 per night (USD)VRBO
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated insid ...
From $159 per night (USD)VRBO
From $240 per night (USD)VRBO
Old Town Key West Live like a local
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Live like a local! This vacation flat is located at Mile marker 1, and sits nestled above the street right on Truman Av ...
From $240 per night (USD)VRBO
From $145 per night (USD)VRBO
Mango Tree Key West Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
True Key West flavor! 1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on White St.with h ...
From $145 per night (USD)VRBO
From $1030 per night (USD)Expedia
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $1030 per night (USD)Expedia
From $1024 per night (USD)VRBO
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $1024 per night (USD)VRBO
From $166 per night (USD)Expedia
CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
SIMPLISTIC ELEGANCE... Enjoy easy island living in this quaint and cozy Key West gem located in the attractive community ...
From $166 per night (USD)Expedia
From $2064 per night (USD)VRBO
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $2064 per night (USD)VRBO
From $311 per night (USD)VRBO
Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Mojitoville is perfect for the discriminating guest who wants to enjoy close proximity to Key West's Historic Seaport wi ...
From $311 per night (USD)VRBO
From $1133 per night (USD)VRBO
\"Tranquility \" At Ann Street Gardens Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $1133 per night (USD)VRBO
From $373 per night (USD)Expedia
PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
PICTURE PERFECT PARADISE... This newly renovated 3 bedroom, 2 bathroom retreat is nestled in the highly sought-after, hi ...
From $373 per night (USD)Expedia
From $169 per night (USD)VRBO
SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $169 per night (USD)VRBO
From $430 per night (USD)Expedia
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $430 per night (USD)Expedia
From $230 per night (USD)VRBO
BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w\/ Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $230 per night (USD)VRBO
From $159 per night (USD)Expedia
LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $159 per night (USD)Expedia
From $686 per night (USD)VRBO
The Most Perfect Old Town Key West Location for a Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroo ...
From $686 per night (USD)VRBO
From $559 per night (USD)Expedia
THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $559 per night (USD)Expedia
From $326 per night (USD)VRBO
HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
ISLAND TIME AWAITS… Step up to this serene, tropical cottage inviting you in with a multitude of swaying palms, a privat ...
From $326 per night (USD)VRBO
From $181 per night (USD)Expedia
GILLEY'S PLACE ~ Fully Renovated 1 Bedroom, 1 Bath Cottage in Old Town!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
AN ESCAPE LIKE NO OTHER… Disconnect from the real world and reconnect with each other in this picture perfect, quaint co ...
From $181 per night (USD)Expedia
From $1710 per night (USD)VRBO
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West. Located on Southard Street just steps from Du ...
From $1710 per night (USD)VRBO
From $1688 per night (USD)Expedia
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 just 5 short blocks to Duval Street. Have bi ...
From $1688 per night (USD)Expedia
From $586 per night (USD)VRBO
ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pass by from ...
From $586 per night (USD)VRBO
From $1813 per night (USD)Expedia
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this O ...
From $1813 per night (USD)Expedia
From $2219 per night (USD)VRBO
STRIPES ~ Delightful Condo w\/Shared Pool in the Heart of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key W ...
From $2219 per night (USD)VRBO
From $4270 per night (USD)Expedia
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...
From $4270 per night (USD)Expedia
From $1950 per night (USD)VRBO
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $1950 per night (USD)VRBO
From $1497 per night (USD)Expedia
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 5
- 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 $1497 per night (USD)Expedia
From $265 per night (USD)VRBO
CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD\/2.5BA - RealKeyWest
- Bedrooms:
- 3
- 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 $265 per night (USD)VRBO
From $517 per night (USD)VRBO
Colony Poolside: A charming bungalow near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter th ...
From $517 per night (USD)VRBO
From $245 per night (USD)VRBO
SEA-NIC VIEW ~ Water-front views, heated pool access and dockage!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
IT'S A SWELL LIFE… Endless island treasures engulf this oceanfront haven which is your one stop destination for a comple ...
From $245 per night (USD)VRBO
From $190 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 $190 per night (USD)VRBO
From $783 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 $783 per night (USD)VRBO
From $586 per night (USD)VRBO
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 2
- 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 $586 per night (USD)VRBO
From $309 per night (USD)VRBO
~ BOHEMIAN HOUSE ~ Come enjoy this well-located, carefree home with a pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $309 per night (USD)VRBO
From $3353 per night (USD)Expedia
Classic Key West Estate - 7BR Mansion off Duval St w\/Pool & Guesthouse Sleeps 16
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation re ...
From $3353 per night (USD)Expedia
From $347 per night (USD)VRBO
Tropical oasis in a former author’s retreat. Sleeps 4.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Former residence of an author and decorated accordingly, this cute cottage is quintessential Key West. Perfectly maintai ...
From $347 per night (USD)VRBO
From $1586 per night (USD)VRBO
PINEAPPLE COTTAGE: 2BR\/2BA-Pvt Pool -1\/2 block to Duval- RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $1586 per night (USD)VRBO
From $681 per night (USD)VRBO
Charming 3 bedroom blocks from Duval Street
- Bedrooms:
- 3
- 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 $681 per night (USD)VRBO
From $476 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 $476 per night (USD)VRBO
From $251 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 $251 per night (USD)VRBO
From $574 per night (USD)VRBO
Old Town 4 \/4.5 house with private pool and 2 poolside cottages + outdoor shower
- Bedrooms:
- 6
- 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 $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 $400 per night (USD)Expedia
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 $400 per night (USD)Expedia
From $435 per night (USD)VRBO
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 $435 per night (USD)VRBO
From $2068 per night (USD)Expedia
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w\/ Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $2068 per night (USD)Expedia
From $910 per night (USD)VRBO
Modern and spacious historic home with private pool and off-street parking.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Brisa Azul (Blue Breeze) is located in the heart of Old Town Key West and will provide the perfect venue to experience t ...
From $910 per night (USD)VRBO
From $3227 per night (USD)VRBO
~ VILLA JOSINE ~ 4 B\/4.5 BA large designer home with pool in a great location
- Bedrooms:
- 5
- 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 $3227 per night (USD)VRBO
From $1406 per night (USD)VRBO
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 $1406 per night (USD)VRBO
From $450 per night (USD)VRBO
Bright and Comfortable 3 bedroom\/2.5 bath Classic Conch in the Meadows
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This Dade County pine house has a strong connection to the sea. It was built in the early 1900's by ship's carpenters an ...
From $450 per night (USD)VRBO
From $1224 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 $1224 per night (USD)VRBO
From $553 per night (USD)Expedia
SERENDIPITY ~ Grand 4 Bedroom\/4.5 Bathroom Home in Heart of Key West!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
TIME TO CREATE LIFELONG MEMORIES… Your long-awaited island retreat is sure to have all expectations exceeded within this ...
From $553 per night (USD)Expedia
From $783 per night (USD)VRBO
Newly Renovated Luxury Coastal Home in the Heart of Old Town Key West
- Bedrooms:
- 4
- Bathrooms:
- 5
- 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 $1751 per night (USD)VRBO
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 $1751 per night (USD)VRBO
Click For PricingVRBO
Penthouse Suite @ KW, Galleon Resort, Not Available in 2024-2025
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Galleon Resort is the best location - Old Town Key West, walking location to all the bars, many high quality restaur ...
Click For PricingVRBO
From $465 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 $465 per night (USD)VRBO
From $357 per night (USD)VRBO
Conch Republic House - Key West Millionaires Row
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $357 per night (USD)VRBO
From $457 per night (USD)VRBO
Colony Sunset- Bright and airy cottage in the heart of old town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in The Colony, a secluded, gated enclave just steps from Duval Street, Colony Sunset is a colorful and relaxing ...
From $457 per night (USD)VRBO
From $267 per night (USD)VRBO
Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, pool
- Bedrooms:
- 3
- 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 $267 per night (USD)VRBO
From $816 per night (USD)VRBO
Hyatt Sunset Harbor, overlooking the stunning and beautiful Gulf of Mexico.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
<p>A short distance from snorkeling, ecotours, and more, this smoke-free condo lets you experience it all. Duval Street ...
From $816 per night (USD)VRBO
From $928 per night (USD)VRBO
Near Duval - Tiki Bar - Private Beach - 2BR Condo - Old Town Key West - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $928 per night (USD)VRBO
From $540 per night (USD)VRBO
Galleon Resort & Marina available Feb8-15 2025
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
1 bed/1 bath overlooking Marina. King master bedroom. Sleeper sofa in living room. Jacuzzi tub in master bath with ceram ...
From $540 per night (USD)VRBO
From $278 per night (USD)VRBO
Paradise on Eaton- 3 bedroom 3 bath home w\/private pool near Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $278 per night (USD)VRBO
From $282 per night (USD)VRBO
Our Key West Dream in Seaport.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Family home for over 20 years, we would like to share our home to those that want to relax, see an amazing sunset, and e ...
From $282 per night (USD)VRBO
From $671 per night (USD)VRBO
BLUE ROOSTER ~ Spectacular 4 Bed\/4 Bath with Pool and Solarium in Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
OLD TOWN PARADISE.... Paradise awaits in a quiet Old Town location. This four bedroom home is set on a cozy lane that i ...
From $671 per night (USD)VRBO
From $333 per night (USD)VRBO
Ohana Paradise At The Historic Seaport , Old Town. Private Home.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amaz ...
From $333 per night (USD)VRBO
From $972 per night (USD)VRBO
★Family Friendly 2BR Condo at Heart of Old Town Key West- Sleeps 6!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $972 per night (USD)VRBO
From $201 per night (USD)VRBO
Conch Republic Studio - Key West Millionaires Row
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In the center of Key West's prestigious "Millionaires Row," Conch Republic Studio is a tranquil getaway for one or a cou ...
From $201 per night (USD)VRBO
From $736 per night (USD)VRBO
Architect's Personal Residence, Private Pool, 1 Blk. to Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Completed in 1992, this two bedroom two bath home was designed by a local architect for the relaxed Key West tropical li ...
From $736 per night (USD)VRBO
From $289 per night (USD)VRBO
OLD TOWN SUMMER’24! Private pool, stunning decor, 5-star reviews. NO PETS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sun yourself on the back patio, then cool off in the pool. Rinse off in the outdoor shower with hot/cold running water. ...
From $289 per night (USD)VRBO
From $196 per night (USD)VRBO
GOOD FEELIN ~ Charming 2 BR\/2 Ba Home Conveniently Located w\/ Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SPOIL YOURSELF… Come unwind in this tropical retreat allowing for your delightful Key West story to unfold. Sounds of sw ...
From $196 per night (USD)VRBO
From $187 per night (USD)Expedia
POSITIVE VIBES ~ Charming 2 BR, 1 Ba Cottage in Peaceful Area w\/ Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LOST ON ISLAND TIME… Treasure your time together within this charming Key West cottage tucked away on this peaceful and ...
From $187 per night (USD)Expedia
From $336 per night (USD)VRBO
GOOD VIBES ~ 2 Cottages w\/ 4 BR\/3 Ba w\/ Outdoor Oasis and Parking!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
MEMORIES TO LAST A LIFETIME… This unique set of 2 charming, Conch style homes provide the perfect compound setting for y ...
From $336 per night (USD)VRBO
From $1441 per night (USD)VRBO
NEW LISTING Old Town Private Pool in Garden Of Eden tropical spa-like Oasis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
( NEW LISTING SEE VRBO LISTING 1223004 for reviews on my other property ) Newly renovated, invitingly spacious, serenely ...
From $1441 per night (USD)VRBO
From $422 per night (USD)VRBO
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
CATCH YOUR SECOND WIND… Unplug in this newly renovated and elegant refuge, a place of tranquility with an island ambianc ...
From $422 per night (USD)VRBO
From $338 per night (USD)VRBO
Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...
From $338 per night (USD)VRBO
From $197 per night (USD)VRBO
Secret Casita: Relaxing 2BD\/2BA escape RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO SECRET CASITA! This hidden gem is a wonderful way to embrace the Key West laid-back lifestyle. This first-f ...
From $197 per night (USD)VRBO
From $266 per night (USD)VRBO
Studio overlooking historic Key West waterfront.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathr ...
From $266 per night (USD)VRBO
From $4724 per night (USD)VRBO
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 9
- Sleeps:
- 20
ABUNDANCE IN OLD TOWN... Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring eve ...
From $4724 per night (USD)VRBO
From $322 per night (USD)VRBO
~ MY HAPPY PLACE ~ A charmingly beautiful treasure in a perfect location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $322 per night (USD)VRBO
From $205 per night (USD)VRBO
Dreamworks Conch Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
PEACEFUL RETREAT... A quintessential Key West cottage in the heart of Old Town and only a few blocks away from Higgs Bea ...
From $205 per night (USD)VRBO
From $571 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 $571 per night (USD)VRBO
From $308 per night (USD)VRBO
ShangriLa Suite \/ Queen Studio \/ Sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $308 per night (USD)VRBO
From $349 per night (USD)Expedia
LA PUERTA ROSA~Charming 3 bed\/2 bath Conch Home in Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $349 per night (USD)Expedia
From $174 per night (USD)VRBO
Peaceful One Bedroom Retreat Located Blocks From Duval Street And The Harbor.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on o ...
From $174 per night (USD)VRBO
From $175 per night (USD)VRBO
Old Town. Spacious 1 bedroom, private heated pool, yard, deck, covered porch.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Old Town. Spacious 1 bedroom on 1st floor. Only 2 other condos in compound. On desirable Frances Street, just 3 blocks ...
From $175 per night (USD)VRBO
From $671 per night (USD)VRBO
Historic, Cozy, prime location with amazing pool and garden in Historic Seaport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a little piece of Key West Paradise? Well, this is it! This stunning cottage is only steps away from the His ...
From $671 per night (USD)VRBO
From $146 per night (USD)VRBO
Ocean-breeze Key West Cottage
- 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 $146 per night (USD)VRBO
From $1043 per night (USD)VRBO
Southard Love - 2.5 Blocks to Downtown, Walk to Beach. 4 Bedrooms, 3 Baths
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE Lane This home is a perfect example of WHY people c ...
From $1043 per night (USD)VRBO
From $1016 per night (USD)VRBO
The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please choose a Saturday check-in, all rentals will be in seven night increments. Thank you for your interest in bookin ...
From $1016 per night (USD)VRBO
From $267 per night (USD)VRBO
Oasis in Old Town - private heated pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 6
Our sweet ‘conch’ cottage in old town Key West has been completely redesigned and custom crafted by 2 architects as our ...
From $267 per night (USD)VRBO
From $382 per night (USD)VRBO
Heart of Downtown Key West Cottage With Off-Street Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minut ...
From $382 per night (USD)VRBO