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From $470 per night (USD)
VRBO
Historic 2BR Old Town Key West w/ hot tub & front porch
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
# Eyebrow Suite @ Eyebrow House Welcome to the Eyebrow Suite, a stunning luxury vacation rental nestled in the vibrant ...
From $470 per night (USD)
VRBO
From $691 per night (USD)
VRBO
Oceanfront Splendor @ the Key West Beach Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
29 NIGHT MINIMUM RENTAL ... This property is not allowed to accept pets. Enjoy endless views of the tranquil waters of ...
From $691 per night (USD)
VRBO
From $436 per night (USD)
VRBO
Escape to the wonderful Cuban Paradise!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon bec ...
From $436 per night (USD)
VRBO
From $787 per night (USD)
VRBO
Key West 3BR townhome w/ private pool & grill
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Palm Royale at Windsor Townhomes, your ideal tropical escape in the heart of Key West, Florida. This stunning ...
From $787 per night (USD)
VRBO
From $300 per night (USD)
VRBO
ESPERANZA SUITE Monthly Rental close to Duval
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Esperanza Suite is a bi-level suite with a very spacious upstairs king bedroom with a writing desk and chair and a color ...
From $300 per night (USD)
VRBO
From $570 per night (USD)
Expedia
THALIA'S RETREAT @ Duval Square 2bd/2ba townhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parkin ...
From $570 per night (USD)
Expedia
From $1045 per night (USD)
VRBO
No secrets at Pilar's Secret - Just a great location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Pilar’s Secret is hidden away in the heart of Old Town Key West just half a block off the famous Duval Street. This secl ...
From $1045 per night (USD)
VRBO
From $268 per night (USD)
VRBO
Deckside Suite - Efficiency at its finest!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get ...
From $268 per night (USD)
VRBO
From $296 per night (USD)
VRBO
Rent at PORCHSIDE PARADISE - Steps to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Porchside Paradise is located in the front section of the Conch Republic Cottages. This beautiful home-away-from-home fe ...
From $296 per night (USD)
VRBO
From $395 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 $395 per night (USD)
VRBO
From $511 per night (USD)
VRBO
Tropical Village: The Southern Cross - Quiet & gated. Pool/Porch/Pet friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
There are stars in the southern sky! The Southern Cross takes its name from the “crux” constellation that guided sailors ...
From $511 per night (USD)
VRBO
From $1508 per night (USD)
Expedia
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1508 per night (USD)
Expedia
From $921 per night (USD)
VRBO
A contemporary island gem that was formerly used as a bottling plant,
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A contemporary island gem that was formerly used as a bottling plant, this modern and spacious home is now a desirable t ...
From $921 per night (USD)
VRBO
From $525 per night (USD)
VRBO
Key West at Ocean’s Corner!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Whether you want to explore the historic sites, enjoy the nightlife, or relax in nature, you’ll find it all during your ...
From $525 per night (USD)
VRBO
$Escape to \Oasis on 18th\ w/ a Private Heated Pool$
From $453 per night (USD)
VRBO
Escape to \"Oasis on 18th\" w/ a Private Heated Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to your own private paradise at ""Oasis on 18th,"" a luxurious three-bedroom, three-bathroom haven nestled within ...
From $453 per night (USD)
VRBO
From $512 per night (USD)
VRBO
Beach Club #112 - Unique Oceanfront living
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $512 per night (USD)
VRBO
From $1483 per night (USD)
VRBO
Hotel Room Galleon Resort, Pool, Hot Tub, In Town!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios h ...
From $1483 per night (USD)
VRBO
From $1953 per night (USD)
VRBO
2/2 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 $1953 per night (USD)
VRBO
From $981 per night (USD)
VRBO
Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $981 per night (USD)
VRBO
From $1760 per night (USD)
VRBO
Sunset Harbor Resort & Spa, Hot Tub, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1760 per night (USD)
VRBO
$Escape to \Casa Escondida\$
From $676 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 $676 per night (USD)
VRBO
From $328 per night (USD)
Expedia
SWEET LIKE SUMMERTIME ~ 3 BR/2Ba Home w/ Pool and Yard!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CLASSIC CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in Bahama Village. This cla ...
From $328 per night (USD)
Expedia
From $291 per night (USD)
VRBO
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $291 per night (USD)
VRBO
From $648 per night (USD)
Expedia
POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
EXQUISITE MODERN FAMILY COMPOUND... If a large home with all the modern luxuries is a must for your next island getaway, ...
From $648 per night (USD)
Expedia
From $356 per night (USD)
VRBO
Waterfront Condo Dock Pool Near Duval St
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Relax above it all in this spacious top-floor waterfront condo in downtown Key West, offering added privacy an ...
From $356 per night (USD)
VRBO
From $429 per night (USD)
Expedia
OASIS SOUTH~Stunning 5 BR/3 Ba w/ Pool!
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
BRING THE WHOLE GANG... If you and your large band of loved ones are looking for the perfect gathering in southernmost ...
From $429 per night (USD)
Expedia
From $332 per night (USD)
VRBO
McCartney`s Manor - Deluxe K Suite W/Pvt. Spa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cool pastel, Caribbean inspired decor with original art throughout by Robin Hix. Blue tooth speaker, Alexa Echo, full ki ...
From $332 per night (USD)
VRBO
From $202 per night (USD)
Expedia
CASA DE CANAL ~ Beautiful Renovated 3 BR, 2 Bath Canal Front Home w/Dockage!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
KEY WEST BOATER'S BONANZA... This waterfront gem is a dream for boating and fishing enthusiasts. Indulge in all your nau ...
From $202 per night (USD)
Expedia
From $301 per night (USD)
VRBO
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 $301 per night (USD)
VRBO
From $150 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 $150 per night (USD)
VRBO
Click For Pricing
VRBO
GARDEN HIDEAWAY ~ Gorgeous 4 BR, 3 BA w/private heated pool and lush gardens!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
PARADISE AWAITS... This charming home is located in one of the most desirable locations in Key West, Casa Marina. Garden ...
Click For Pricing
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 $892 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the Gulf of Mexico; 2 bd villa!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at Hyatt Sunset Harbor! **Reservations are available in weekly (7 ni ...
From $892 per night (USD)
VRBO
From $506 per night (USD)
VRBO
Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our Key West Condo, the Key West Cabana. This spacious well appointed 2 bedroom, 2 full bath condo that’s ri ...
From $506 per night (USD)
VRBO
$\Tranquility \ At Ann Street Gardens Steps From Duval$
From $798 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 $798 per night (USD)
VRBO
From $410 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 $410 per night (USD)
Expedia
From $815 per night (USD)
VRBO
Hyatt Residence Club - Key West, FL - 2 Bedroom Unit - Beach House Location!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience a tropical getaway designed in classic Key West style, o ering manicured gardens and panoramic views of the G ...
From $815 per night (USD)
VRBO
From $454 per night (USD)
VRBO
💲 HUGE DISCOUNT for 28 day OCEAN FRONT! 90 FT BALCONY💰
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Please contact the owner for stays less than 28 days before you try to book. Military Vouchers are Welcome! In Key We ...
From $454 per night (USD)
VRBO
From $408 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 $408 per night (USD)
VRBO
From $515 per night (USD)
VRBO
Enjoy More Privacy in a Truman Annex End Unit Townhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $515 per night (USD)
VRBO
From $832 per night (USD)
VRBO
Quintessential Key West Resort! Hyatt Windward Pointe two bedroom. Book now!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at Hyatt Windward Pointe! **Reservations are available in weekly (7 ...
From $832 per night (USD)
VRBO
From $1562 per night (USD)
Expedia
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Bedrooms:
6
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 $1562 per night (USD)
Expedia
From $320 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 $320 per night (USD)
VRBO
From $381 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 retreat is nestled in the highly sought-after neighborhood of The Meado ...
From $381 per night (USD)
Expedia
From $163 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 $163 per night (USD)
VRBO
From $890 per night (USD)
Expedia
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 $890 per night (USD)
Expedia
From $501 per night (USD)
VRBO
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Our Home Away from home. Our condo is located in the LaBrisa complex which is a GATED COMMUNITY across from ...
From $501 per night (USD)
VRBO
From $182 per night (USD)
Expedia
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 $182 per night (USD)
Expedia
From $161 per night (USD)
VRBO
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
COZY VALUE IN TRUMAN ANNEX… This 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the ...
From $161 per night (USD)
VRBO
From $908 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 $908 per night (USD)
VRBO
From $537 per night (USD)
VRBO
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
YOUR OCEANFRONT OASIS AWAITS... This remarkable and magical retreat is sure to provide all the R & R you need to refresh ...
From $537 per night (USD)
VRBO
From $491 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 $491 per night (USD)
Expedia
From $216 per night (USD)
VRBO
EL JARDIN 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 $216 per night (USD)
VRBO
From $156 per night (USD)
Expedia
LA ENTRADA ROSA ~ 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 $156 per night (USD)
Expedia
From $394 per night (USD)
VRBO
SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Annex Home w/Private Heated Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $394 per night (USD)
VRBO
From $469 per night (USD)
Expedia
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BEACHES ON BOTH SIDES... This two bedroom condo located at 1800 Atlantic Condominiums near the airport, beaches, restaur ...
From $469 per night (USD)
Expedia
From $236 per night (USD)
VRBO
SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
IMMACULATE RETREAT... Beautifully designed townhouse located in the Southernmost Cabana Community of Key West just steps ...
From $236 per night (USD)
VRBO
From $630 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 $630 per night (USD)
Expedia
From $461 per night (USD)
VRBO
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BEACHES ON BOTH SIDES... This newly renovated two bedroom condo is close to the airport, beaches, restaurants and minute ...
From $461 per night (USD)
VRBO
From $268 per night (USD)
Expedia
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 $268 per night (USD)
Expedia
From $163 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 $163 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Foundry 7 - History in Paradise - 2BD/2Bath - Truman Annex - Pool access
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Foundry 7 – A Rare Gem in Key West’s Prestigious Truman Annex! Step into paradise at Foundry 7, a spectacula ...
From $392 per night (USD)
VRBO
From $187 per night (USD)
VRBO
THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Shipyard Unit!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
COMFORT AND VALUE IN TRUMAN ANNEX… This newly renovated 2nd floor two bedroom condo is located in The Shipyard, a neighb ...
From $187 per night (USD)
VRBO
From $422 per night (USD)
Expedia
GARDEN OASIS ~ Great Casa Marina Location with True Island Elegance!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
WHEN ONLY THE BEST WILL DO... Located in the Casa Marina Area of Key West known for spacious and elegant fine homes; the ...
From $422 per night (USD)
Expedia
From $1053 per night (USD)
VRBO
Jasmine Place - Right there with Hemingway - 2BD/2Bath - Private Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
WELCOME TO JASMINE PLACE! Jasmine Place is a beautiful and enchanting home conveniently located next door to the Ernes ...
From $1053 per night (USD)
VRBO
From $385 per night (USD)
Expedia
CLOUD 9 ~ 4 Bedroom, 3.5 Bathroom with Off Street Parking and Pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
NO PASSPORT REQUIRED… A lovingly restored island retreat with luxurious coastal flair, this home’s aesthetic beauty draw ...
From $385 per night (USD)
Expedia
From $585 per night (USD)
VRBO
Waterfront Key West Home with Pool-Hot Tub on Riveria canal! 28 NIGHT MIN STAY.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
28 NIGHT MIN STAY REQ. PLEASE DO NOT SUBMIT A BOOKING REQUEST FOR ANYTHING LESS. Large 3 Bedroom / 2 Bath private resid ...
From $585 per night (USD)
VRBO
From $616 per night (USD)
Expedia
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 $616 per night (USD)
Expedia
From $1195 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 $1195 per night (USD)
VRBO
From $719 per night (USD)
Expedia
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
LOCATION LOCATION LOCATION... Enjoy this convenient Old Town Location. Located a block from Duval and a short walk or b ...
From $719 per night (USD)
Expedia
From $730 per night (USD)
VRBO
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated 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 $730 per night (USD)
VRBO
From $727 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 $727 per night (USD)
Expedia
From $708 per night (USD)
VRBO
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
JUST OFF DUVAL... Private single family home with three bedrooms and three bathrooms. Open the rear French doors to a p ...
From $708 per night (USD)
VRBO
From $364 per night (USD)
Expedia
SEA LA VIE ~ Living in Complete Luxury in This Elegant Three Story Home!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
THREE STORY GRANDEUR… Located in the Casa Marina District in Old Town. This home is elegant, yet quite the tropical del ...
From $364 per night (USD)
Expedia
From $352 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 $352 per night (USD)
VRBO
From $757 per night (USD)
Expedia
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Bedrooms:
2
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 $757 per night (USD)
Expedia
From $868 per night (USD)
VRBO
LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A SWEET SURPRISE JUST OFF DUVAL... Private single family home with off street parking totaling three bedrooms, two and h ...
From $868 per night (USD)
VRBO
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Expedia
SUNCATCHER~4 Bedroom, 4 Bathroom in Old Town with Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
ONLY THE BEST WILL DO… An exceptional opportunity to immerse yourself in island life within this renovated, classic Key ...
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Expedia
From $361 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. Perfect monthly r ...
From $361 per night (USD)
VRBO
From $797 per night (USD)
VRBO
CASABELLA@DUVAL SQUARE Lovely 2 Bedroom 2.5 Bath Townhome in a great location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Duval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool a ...
From $797 per night (USD)
VRBO
From $385 per night (USD)
VRBO
Colony Poolside: A charming bungalow near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter th ...
From $385 per night (USD)
VRBO
From $507 per night (USD)
VRBO
Beach Club #103 - Unique oceanfront living with breathtaking views
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $507 per night (USD)
VRBO
From $497 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 $497 per night (USD)
VRBO
From $235 per night (USD)
Expedia
SEA-NIC VIEW ~ 2 BR/2Ba Water-front views, 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 $235 per night (USD)
Expedia
From $2392 per night (USD)
VRBO
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 $2392 per night (USD)
VRBO
From $172 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 $172 per night (USD)
VRBO
From $597 per night (USD)
VRBO
Duval Square Condo-2 bedroom 2.5 bath, w/pool, parking, on Duval St
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $597 per night (USD)
VRBO
From $429 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 $429 per night (USD)
VRBO
From $343 per night (USD)
VRBO
Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes th ...
From $343 per night (USD)
VRBO
From $243 per night (USD)
VRBO
Reduced Pricing!!! A Slice of Paradise! @ the Shipyard Palms!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
In the heart of Old Town, with the beautiful community of private homes and condominiums of Truman Annex, this Shipyard ...
From $243 per night (USD)
VRBO
From $583 per night (USD)
VRBO
Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
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 $583 per night (USD)
VRBO
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Expedia
Home away from home!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located in the gated community of the Key West Golf Club, enjoy your morning coffee in the enclosed back porch overlooki ...
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Expedia
From $420 per night (USD)
VRBO
Corazon - Palm Tree Paradise- Private Pool - 2BD/2.5Bath - Prime Location!
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 $420 per night (USD)
VRBO
From $213 per night (USD)
Expedia
ALMOST HEAVEN ~ Stunning 2 Bedroom, 2 Bathroom Condo with Community Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
UNWIND IN PARADISE… Let you worries wash away in this peaceful retreat located within the 1800 Atlantic community offeri ...
From $213 per night (USD)
Expedia
From $263 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 $263 per night (USD)
VRBO
From $728 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 $728 per night (USD)
VRBO
From $590 per night (USD)
VRBO
Luxury two floor apartment in prime location of famous Duval Street
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This Modern & Spacious 2 story Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Sho ...
From $590 per night (USD)
VRBO
From $548 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 $548 per night (USD)
VRBO
From $626 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 $626 per night (USD)
VRBO
From $698 per night (USD)
VRBO
Serenity now. Private Home. Pool. On the water.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
LOCATION LOCATION! Located on the only canal in Key West, with a protected bird sanctuary across the canal. A short Ub ...
From $698 per night (USD)
VRBO

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