Fleming Key Rentals
- From $795 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 are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $795 per night (USD)VRBO
- From $1512 per night (USD)
Expedia
Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $1512 per night (USD)Expedia
- From $1555 per night (USD)
VRBO
Bayview Retreat: Spacious Luxury Waterfront Home with Private Pool and Dock!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1555 per night (USD)VRBO
- Click For Pricing
VRBO
Key West Like it should be! 3 Comfortable Units, Onsite Dining, 3 Swimming Pools
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- From $2922 per night (USD)
VRBO
Key West Experience like No Other! Pet-friendly, 3 Pools!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2922 per night (USD)VRBO
- From $1613 per night (USD)
VRBO
Authentic Key West Adventure! 3 Comfortable Units, 3 Pools, Pets Allowed!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1613 per night (USD)VRBO
- From $2115 per night (USD)
VRBO
Family and Friends Getaway! 4 Comfortable Units, 3 Pools, Onsite Dining!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2115 per night (USD)VRBO
- Click For Pricing
VRBO
Your Key West Getaway! 4 Roomy Units, Pets Allowed, 3 Pools, Onsite Dining!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- From $610 per night (USD)
VRBO
Large 2\/2 Waterfront Condo Great View Pool & Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $610 per night (USD)VRBO
- From $621 per night (USD)
VRBO
Downtown Waterfront 2\/2 Dock & Pool Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $621 per night (USD)VRBO
- From $1549 per night (USD)
VRBO
Downtown Waterfront Penthouse Pool, Parking, Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Bring your family & friends to this 2200sqft waterfront Penthouse condo. Endless water views from one of the t ...
From $1549 per night (USD)VRBO
- From $568 per night (USD)
VRBO
2\/2 Fully Updated Old Town Waterfront Corner Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this fully updated 1350sqft Waterfront corner condo home. Boat sl ...
From $568 per night (USD)VRBO
- From $450 per night (USD)
VRBO
The Elizabeth Suite at The Bayview House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We are pleased to introduce The Fleming Suite at The Bayview House , a 1-bedroom, 1-bathroom nightly rental. Located in ...
From $450 per night (USD)VRBO
- From $300 per night (USD)
Expedia
The Fleming Suite at The Bayview House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We are pleased to introduce The Fleming Suite at The Bayview House , a 1-bedroom, 1-bathroom nightly rental. Located in ...
From $300 per night (USD)Expedia
- From $159 per night (USD)
VRBO
Breezy Key West 1st-Floor Condo w\/ Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $159 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Our Piece of Paradise-
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $375 per night (USD)Expedia
- From $314 per night (USD)
VRBO
Midnight Cowboy by AvantStay | 3 Artistic Spaces
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
*Please note that this home is available for 28+ night stays only.* Midnight Cowboy is a one-of-a-kind Key West escape ...
From $314 per night (USD)VRBO
- From $164 per night (USD)
Expedia
Tennessee Williams by AvantStay | Funky Design + Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.*Tennessee Williams is a one-of-a-kind Key West escape ...
From $164 per night (USD)Expedia
- From $146 per night (USD)
VRBO
Old Town Key West Home w\/ Deck < 1 Mi to Duval St!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Ensure your next stop in Key West includes easy access to all of the island’s most iconic attractions when you book this ...
From $146 per night (USD)VRBO
- From $630 per night (USD)
Expedia
KAMP by Brightwild | Rooftop Penthouse On Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $630 per night (USD)Expedia
- From $624 per night (USD)
VRBO
Custom House Inn | Two 2nd Floor Suites On Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $624 per night (USD)VRBO
- From $605 per night (USD)
Expedia
Custom House Inn | Two Suites On Duval St
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $605 per night (USD)Expedia
- From $578 per night (USD)
VRBO
NEW Spacious 2\/2 Waterfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip a ...
From $578 per night (USD)VRBO
- From $280 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 $280 per night (USD)Expedia
- From $119 per night (USD)
VRBO
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated insid ...
From $119 per night (USD)VRBO
- From $677 per night (USD)
VRBO
SALTWATER SOPHISTICATION ~ Renovated 4 BR, 4.5 Ba Downtown Home w\/ Pool!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
PREMIER HISTORICAL RETREAT... Just steps from the Seaport District hosting the best waterfront restaurants and world fam ...
From $677 per night (USD)VRBO
- From $369 per night (USD)
VRBO
The Hollinsed House | Harvey`s Haven
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Harvey's Haven—a beautiful studio in the heart of Old Town Key West! Ideally located at the Hollinsed House o ...
From $369 per night (USD)VRBO
- From $345 per night (USD)
VRBO
Key Lime Cottage (Monthly)
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Located on the edge of Old Town near the art district on White Street the Key Lime Cottage offers great accommodations f ...
From $345 per night (USD)VRBO
- From $518 per night (USD)
VRBO
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 $518 per night (USD)VRBO
- From $689 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 $689 per night (USD)VRBO
- From $182 per night (USD)
VRBO
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 $182 per night (USD)VRBO
- From $137 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 $137 per night (USD)VRBO
- From $1450 per night (USD)
VRBO
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $1450 per night (USD)VRBO
- From $267 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 $267 per night (USD)VRBO
- From $600 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 $600 per night (USD)VRBO
- From $1184 per night (USD)
VRBO
Windsor Townhome #3 - Green Gecko
- 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 $1184 per night (USD)VRBO
- From $302 per night (USD)
VRBO
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 $302 per night (USD)VRBO
- From $350 per night (USD)
VRBO
A Bit of Heaven- Monthly Rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Bit of Heaven This quintessential Key West eyebrow home is located in Old Town's prime Historic District sitting just ...
From $350 per night (USD)VRBO
- From $108 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 $108 per night (USD)VRBO
- From $500 per night (USD)
VRBO
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $500 per night (USD)VRBO
- From $200 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 $200 per night (USD)VRBO
- From $218 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 $218 per night (USD)VRBO
- From $675 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 $675 per night (USD)VRBO
- From $286 per night (USD)
VRBO
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 $286 per night (USD)VRBO
- From $170 per night (USD)
VRBO
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 $170 per night (USD)VRBO
- From $143 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 $143 per night (USD)VRBO
- From $285 per night (USD)
VRBO
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 $285 per night (USD)VRBO
- From $1006 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 $1006 per night (USD)VRBO
- From $819 per night (USD)
VRBO
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 $819 per night (USD)VRBO
- From $232 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 $232 per night (USD)VRBO
- From $1109 per night (USD)
VRBO
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 $1109 per night (USD)VRBO
- From $899 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 $899 per night (USD)VRBO
- From $1850 per night (USD)
VRBO
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 $1850 per night (USD)VRBO
- From $1164 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 $1164 per night (USD)VRBO
- From $961 per night (USD)
VRBO
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 $961 per night (USD)VRBO
- From $209 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 $209 per night (USD)VRBO
- From $380 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 $380 per night (USD)VRBO
- From $299 per night (USD)
Expedia
Tropical oasis in a former author’s retreat. Sleeps 4.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Former residence of an author and decorated accordingly, this cute cottage is quintessential Key West. Perfectly maintai ...
From $299 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Charming 2bed 2bath in Old Town w\/ shared pool, reserved parking, open layout
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Pearl in Paradise! Our charming vacation rental in Old Town Key West! This delightful two-bedroom, two-ba ...
From $179 per night (USD)VRBO
- From $441 per night (USD)
VRBO
2 bdrm Condo w\/ boat slip Pelican Landing Antigua
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $441 per night (USD)VRBO
- From $396 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 $396 per night (USD)VRBO
- From $445 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 $445 per night (USD)VRBO
- From $210 per night (USD)
VRBO
SEA-NIC VIEW ~ Price reduction for April-May!!!
- 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 $210 per night (USD)VRBO
- From $1975 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 $1975 per night (USD)VRBO
- From $713 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 $713 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 $294 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 $294 per night (USD)VRBO
- From $206 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 $206 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 $275 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 $275 per night (USD)VRBO
- From $460 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 $460 per night (USD)VRBO
- From $344 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 $344 per night (USD)VRBO
- Click For Pricing
VRBO
PAGITT HOUSE: Old Town - Private Pool - 3BR/2BA - Sleeps 6 - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME TO PAGITT HOUSE! Experience the original Key West by staying at this historical treasure! Pagitt House is a ...
Click For PricingVRBO
- From $353 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 $353 per night (USD)VRBO
- From $1181 per night (USD)
VRBO
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 $1181 per night (USD)VRBO
- From $649 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 $649 per night (USD)VRBO
- From $1525 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 $1525 per night (USD)VRBO
- From $1075 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 $1075 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
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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 ...
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- From $1100 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 $1100 per night (USD)VRBO
- From $367 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 $367 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 $155 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 $155 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 $347 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 $347 per night (USD)VRBO
- From $227 per night (USD)
VRBO
30 night stay, in Historic downtown, 2bed 2.5bath, shared pool\/jacuzzi, porch
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps ...
From $227 per night (USD)VRBO
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VRBO
3bed 2bath Conch house on Eaton St w\/ private pool near historic seaport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This traditional cottage, in the heart of Old Town, was built by a shipbuilder in the early 1900’s. It has all the charm ...
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- 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 $712 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 $712 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 ...
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- From $278 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 $278 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 $795 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 $795 per night (USD)VRBO
- From $639 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 $639 per night (USD)VRBO
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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 ...
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- From $569 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 $569 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 ...
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- 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 ...
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