Fleming Key Rentals
- From $167 per night (USD)
VRBO
LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $167 per night (USD)VRBO
- From $171 per night (USD)
Expedia
HEMINGWAY'S HIDEOUT ~ Sophisticated, Historic Old Town Cottage with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
ISLAND SOPHISTICATION AWAITS… Step up to this serene, tropical cottage inviting you in with a multitude of swaying palms ...
From $171 per night (USD)Expedia
- From $792 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 $792 per night (USD)VRBO
- From $322 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 $322 per night (USD)Expedia
- From $113 per night (USD)
VRBO
GILLEY'S PLACE ~ Fully Renovated 1 Bedroom, 1 Bath Cottage in Old Town!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
AN ESCAPE LIKE NO OTHER… Disconnect from the real world and reconnect with each other in this picture perfect, quaint co ...
From $113 per night (USD)VRBO
- From $284 per night (USD)
Expedia
BOOMERANG BOATHOUSE ~ Relax in This Beautiful 4 Bedroom\/2.5 Bath Location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
RETURN TO EQUANIMITY... “Boomerang Boathouse” is nestled in the peaceful neighborhood locals refer to as The Meadows. T ...
From $284 per night (USD)Expedia
- From $955 per night (USD)
VRBO
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $955 per night (USD)VRBO
- From $821 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 $821 per night (USD)Expedia
- From $212 per night (USD)
VRBO
ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pass by from ...
From $212 per night (USD)VRBO
- From $1011 per night (USD)
Expedia
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this O ...
From $1011 per night (USD)Expedia
- From $822 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 $822 per night (USD)VRBO
- From $1721 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 $1721 per night (USD)Expedia
- From $829 per night (USD)
VRBO
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Home in Desirable Downtown Location!
- 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 $829 per night (USD)VRBO
- From $648 per night (USD)
Expedia
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, 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 $648 per night (USD)Expedia
- From $286 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 $286 per night (USD)VRBO
- From $338 per night (USD)
VRBO
Colony Poolside: A charming bungalow near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter th ...
From $338 per night (USD)VRBO
- From $162 per night (USD)
VRBO
SEA-NIC VIEW ~ Price reduction for May thru July!!!
- 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 $162 per night (USD)VRBO
- From $155 per night (USD)
VRBO
Pearl in Paradise-Charming 2bed 2bath Old Town home w\/ shared pool, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
xEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and pri ...
From $155 per night (USD)VRBO
- From $387 per night (USD)
VRBO
Pelican Landing Antigua-2bedroom waterfront condo w\/boat slip, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $387 per night (USD)VRBO
- From $395 per night (USD)
VRBO
2 bdrm Condo w\/ boat slip Pelican Landing Harbor Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $395 per night (USD)VRBO
- From $418 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 $418 per night (USD)VRBO
- From $1853 per night (USD)
VRBO
Classic Key West Estate
- 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 $1853 per night (USD)VRBO
- From $793 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 $793 per night (USD)VRBO
- From $300 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 $300 per night (USD)VRBO
- From $247 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 $247 per night (USD)VRBO
- From $180 per night (USD)
Expedia
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 $180 per night (USD)Expedia
- From $209 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 $209 per night (USD)VRBO
- From $500 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 $500 per night (USD)VRBO
- From $600 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 $600 per night (USD)VRBO
- From $290 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 $290 per night (USD)VRBO
- From $500 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 $500 per night (USD)VRBO
- From $254 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 $254 per night (USD)Expedia
- From $358 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 $358 per night (USD)VRBO
- From $1071 per night (USD)
Expedia
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w\/ Private 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 $1071 per night (USD)Expedia
- From $544 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 $544 per night (USD)VRBO
- From $1698 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 $1698 per night (USD)VRBO
- From $1018 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 $1018 per night (USD)VRBO
- From $330 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 $330 per night (USD)VRBO
- Click For Pricing
VRBO
Walk to Duval St and Mallory Square - 2BR Condo at Heart of Old Town Key West
- 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 ...
Click For PricingVRBO
- From $1063 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 $1063 per night (USD)VRBO
- From $358 per night (USD)
VRBO
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 $358 per night (USD)VRBO
- From $1500 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 $1500 per night (USD)VRBO
- From $675 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 $675 per night (USD)VRBO
- From $148 per night (USD)
VRBO
Conch Republic House - Key West Millionaires Row
- Bedrooms:
- 3
- 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 $148 per night (USD)VRBO
- From $300 per night (USD)
VRBO
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, gated enclave just steps from Duval Street, Colony Sunset is a colorful and relaxing ...
From $300 per night (USD)VRBO
- From $217 per night (USD)
VRBO
Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $217 per night (USD)VRBO
- From $219 per night (USD)
VRBO
Paradise on Eaton- 3 bedroom 3 bath home w\/private pool near Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $219 per night (USD)VRBO
- From $261 per night (USD)
VRBO
Our Key West Dream in Seaport.
- Bedrooms:
- 3
- Bathrooms:
- 2
- 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 $261 per night (USD)VRBO
- From $787 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 $787 per night (USD)VRBO
- Click For Pricing
VRBO
Galleon Resort - Balcony Overlooking Marina w\/ Stair to Boardwalk, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WATERFRONT TWO BEDROOMS, 2 BATHS, FULL KITCHEN IN KEY WEST HISTORIC SEAPORT Condo type unit with an area of 1300 squar ...
Click For PricingVRBO
- From $274 per night (USD)
VRBO
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 $274 per night (USD)VRBO
- From $300 per night (USD)
VRBO
2-Story Waterfront Condo near Old Town + Pool and Boat Slip, Available Monthly
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Bay Villas is a charming 2-story waterfront condo located on Hilton Haven Road, a quiet cul-de-sac on Trumbo Point, whic ...
From $300 per night (USD)VRBO
- From $895 per night (USD)
VRBO
SEAPORT SERENITY at Galleon Resort near Mallory Square—King Suite-Beach-Pool-BBQ
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OCEANFRONT CASUAL LUXURY CONDO RENTAL 40 FT FROM THE WATER WITH BREATHTAKING & UNOBSTRUCTED VIEWS OF KEY WEST HARBOR AND ...
From $895 per night (USD)VRBO
- From $657 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the stunning and beautiful Gulf of Mexico.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
These are 7-night rentals, with check-in on Fridays, Saturdays and Sundays only. Discover a relaxing oasis overlooking ...
From $657 per night (USD)VRBO
- Click For Pricing
VRBO
Studio unit at the Galleon Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleon offers studio type units that can sleep two to four people depending on the unit. All units are air conditio ...
Click For PricingVRBO
- From $552 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 $552 per night (USD)VRBO
- Click For Pricing
VRBO
Galleon Resort 2bed\/2bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bed/2bath overlooking Marina. King master bedroom. Queen in 2nd bedroom. Sleeper sofa in living room. Jacuzzi tub in m ...
Click For PricingVRBO
- Click For Pricing
VRBO
The Galleon Resort Nov 2 - Nov 9, 2019\/ Boat Week 2019 Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Great unit for boat week in Key West. Saturday to Saturday availability. 2 bedroom condo at The Galleon Resort sleeps 6 ...
Click For PricingVRBO
- From $774 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 $774 per night (USD)VRBO
- From $75 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 $75 per night (USD)VRBO
- Click For Pricing
VRBO
THE GALLEON - UNIT B-42
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort, Unit B-42. Available Saturday Nov 9, 2019 thru Saturday Nov 16, 2019 (7 nights) . Sleeps six. Pool a ...
Click For PricingVRBO
- From $588 per night (USD)
VRBO
Architect's Personal Residence, Private Pool, 1 Blk. to Duval
- Bedrooms:
- 3
- Bathrooms:
- 2
- 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 $588 per night (USD)VRBO
- From $1260 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 $1260 per night (USD)VRBO
- Click For Pricing
VRBO
Island Song - Paradise in the Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Song is a 2-Bedroom, 2-Bath Paradise! Centrally located on Key West, this condo has the best backyard in town, t ...
Click For PricingVRBO
- From $499 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 $499 per night (USD)VRBO
- From $2000 per night (USD)
VRBO
The Admiral of the Seaport
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 12
The Admiral of the Seaport is a luxurious custom built estate located in the heart of Old Town Key West. Just 3 blocks ...
From $2000 per night (USD)VRBO
- From $299 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 $299 per night (USD)VRBO
- From $117 per night (USD)
Expedia
GOOD FEELIN ~ Charming 2 BR\/2 Ba Home Conveniently Located w\/ Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
SPOIL YOURSELF… Come unwind in this tropical retreat allowing for your delightful Key West story to unfold. Sounds of sw ...
From $117 per night (USD)Expedia
- From $140 per night (USD)
VRBO
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 $140 per night (USD)VRBO
- From $261 per night (USD)
Expedia
GOOD VIBES ~ 2 Cottages w\/ 4 BR\/3 Ba w\/ Outdoor Oasis and Parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
MEMORIES TO LAST A LIFETIME… This unique set of 2 charming, Conch style homes provide the perfect compound setting for y ...
From $261 per night (USD)Expedia
- From $846 per night (USD)
VRBO
Windsor Townhome #6- 3 bedroom 3.5 bath with private pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently ...
From $846 per night (USD)VRBO
- From $129 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 $129 per night (USD)VRBO
- From $183 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 $183 per night (USD)VRBO
- From $1667 per night (USD)
Expedia
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 8
- 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 $1667 per night (USD)Expedia
- From $205 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 $205 per night (USD)VRBO
- From $175 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 $175 per night (USD)VRBO
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VRBO
Welcome Aboard! Prime location in Key West on a 46' Luxury Catamaran
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Join us on a 46' luxury sailing catamaran, The Space Between, enjoying all the comforts of home and the added beauty and ...
Click For PricingVRBO
- From $393 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 $393 per night (USD)VRBO
- Click For Pricing
VRBO
Price Reduction!!! Penthouse Suite @ KW, Galleon Resort, Avail 6\/29 - 7\/6\/2024
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $388 per night (USD)
Expedia
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 $388 per night (USD)Expedia
- Click For Pricing
VRBO
Galleon Key West Resort - Waterfront Marina 2-Bedroom Suite + Beach + Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Best view in Key West! Sitting atop the Galleon Resort in a penthouse room with a clear view of the Galleon Marina and h ...
Click For PricingVRBO
- From $300 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 $300 per night (USD)VRBO
- From $163 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 $163 per night (USD)VRBO
- Click For Pricing
Expedia
Osprey- 1 Bed\/1 Bath Nightly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Ideally located at the Colony on Olivia Street. ...
Click For PricingExpedia
- Click For Pricing
VRBO
Charming House - 3 Bedroom 1 Bath with pool.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Quaint property on the edge of Old Town. Minutes walk to White street with cool galleries, yoga studios, restaurants and ...
Click For PricingVRBO
- From $200 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 $200 per night (USD)VRBO
- From $113 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 $113 per night (USD)VRBO
- From $800 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 $800 per night (USD)VRBO
- From $209 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 $209 per night (USD)VRBO
- From $249 per night (USD)
Expedia
LA PUERTA ROSA~Charming 3 bed\/2 bath Conch Home in Old Town Key West!
- Bedrooms:
- 2
- 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 $249 per night (USD)Expedia
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Expedia
Casa Loca- 3 bedroom | 2.5 bath | sleeps up to 8 with private pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Loca is perfect for guests who want to enjoy the finest Key West has to offer! The perfect location, less than one ...
Click For PricingExpedia
- From $150 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 $150 per night (USD)VRBO
- From $300 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 $300 per night (USD)VRBO
- Click For Pricing
Expedia
Hidden Oasis- 1 bedroom 1 bath in Old Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tucked among a colony of freestanding Conch style cottages, amid lush tropical landscaping, sits the newly renovated Hid ...
Click For PricingExpedia
- Click For Pricing
Expedia
Fleming-O 2 bedrooms | 1 bath | sleeps up to 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Fleming-O (pronounced “Flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and o ...
Click For PricingExpedia
- From $677 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 $677 per night (USD)VRBO
- From $234 per night (USD)
VRBO
Oasis in Old Town - private heated pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Our sweet ‘conch’ cottage in old town Key West has been completely redesigned and custom crafted by 2 architects as our ...
From $234 per night (USD)VRBO
- From $462 per night (USD)
VRBO
Pelican Landing Dominica-2bedroom waterfront condo w\/boat slip, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $462 per night (USD)VRBO
- From $467 per night (USD)
VRBO
Pelican Landing Falmingo-2bedroom waterfront condo w\/boat slip, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $467 per night (USD)VRBO
- From $250 per night (USD)
VRBO
The Palms -3 bedroom 2 bath home in The Meadows w\/ pool oasis & guest cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $250 per night (USD)VRBO