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From $630 per night (USD)
VRBO
LIFE IN THE SLOW LANE at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming unit has a whimsical nautical feel with the blue and white décor. There are two master suites, one on t ...
From $630 per night (USD)
VRBO
From $720 per night (USD)
Expedia
SALTWATER ANGLER at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
From $720 per night (USD)
Expedia
From $427 per night (USD)
VRBO
Island Breezes at The Truman Annex in Key West@ the Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park ...
From $427 per night (USD)
VRBO
From $739 per night (USD)
Expedia
A HARBOUR ROOST at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $739 per night (USD)
Expedia
From $386 per night (USD)
VRBO
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Be Still – Your Private Island Oasis in Key West Nestled on an oversized corner lot just a few blocks from W ...
From $386 per night (USD)
VRBO
From $520 per night (USD)
Expedia
**ASCENSION** @ The Truman Annex Compass Realty
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stepping through the white picket gate into this town home located in the gated Truman Annex community, in the heart of ...
From $520 per night (USD)
Expedia
From $500 per night (USD)
VRBO
DANCING PALMS at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come stay at this bright and airy 2 bedroom, 2 full bath town home in the renowned Truman Annex in Old Town. Leave the c ...
From $500 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful views and close to Duval Street festivities and boat docks. Wks 29-30.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
Click For Pricing
Expedia
From $890 per night (USD)
VRBO
OCEAN BREEZE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! ...
From $890 per night (USD)
VRBO
From $493 per night (USD)
Expedia
SAGO PALM at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $493 per night (USD)
Expedia
From $215 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 $215 per night (USD)
VRBO
From $713 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 $713 per night (USD)
VRBO
From $562 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 $562 per night (USD)
VRBO
From $433 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 $433 per night (USD)
VRBO
From $605 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 $605 per night (USD)
VRBO
From $583 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 $583 per night (USD)
VRBO
From $383 per night (USD)
VRBO
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for compute ...
From $383 per night (USD)
VRBO
From $216 per night (USD)
Expedia
Studio Apartment in the Casa Antigua, Hemingway's 1st Key West Hotel Residence
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Beautiful vacation home where you can relax and unwind with a friend and take you shoe off and enjoy nature. gorgeous s ...
From $216 per night (USD)
Expedia
From $403 per night (USD)
VRBO
PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $403 per night (USD)
VRBO
From $472 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $472 per night (USD)
VRBO
From $758 per night (USD)
VRBO
~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are ...
From $758 per night (USD)
VRBO
From $354 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. Perfect monthly r ...
From $354 per night (USD)
Expedia
From $474 per night (USD)
VRBO
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We want you to know that your safety and comfort while in Key West is our utmost priority. Cleaning supplies are availab ...
From $474 per night (USD)
VRBO
From $1107 per night (USD)
Expedia
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $1107 per night (USD)
Expedia
From $676 per night (USD)
VRBO
CEASAR'S PARADISE - A MODERN LUXURY RETREAT W/ 4+ Bedrooms/ 5.5 Baths
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Modern sophistication is the design aesthetic in this newer built home in Old Town Key West with designer touches throug ...
From $676 per night (USD)
VRBO
From $767 per night (USD)
Expedia
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, ...
From $767 per night (USD)
Expedia
From $750 per night (USD)
VRBO
VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
28 Night Minimum Stay Required. This beautiful island retreat is secluded away on a quiet Old Town lane and features 5 l ...
From $750 per night (USD)
VRBO
From $766 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 $766 per night (USD)
VRBO
From $510 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 $510 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Prime location, stunning views from 2 decks—walk or ride to explore the island!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Walk everywhere from this little part of Paradise, you will never need a car. Located in beautiful Old Town, you are vi ...
From $436 per night (USD)
Expedia
From $730 per night (USD)
VRBO
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroo ...
From $730 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nice quiet landing a few blocks from the action on Duval Street. This is a Saturday-Saturday weekly home for the rest of ...
From $202 per night (USD)
Expedia
From $1096 per night (USD)
VRBO
Waterfront 4 Bed 4 Bath Home in Key Cove Landings
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1096 per night (USD)
VRBO
From $288 per night (USD)
Expedia
GOLF VILLA - Monthly Rental - 2BD/2BA -Community Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Golf Villa, your perfect Key West getaway in the highly sought-after Key West Golf Club neighborhood! Immerse ...
From $288 per night (USD)
Expedia
From $371 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
From $371 per night (USD)
VRBO
From $1065 per night (USD)
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 ...
From $1065 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Sea Breeze at 1800 Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Sea Breeze at 1800 Atlantic — Your Luxurious Oceanfront Escape in Key West Discover the ultimate blend of co ...
From $376 per night (USD)
VRBO
From $629 per night (USD)
Expedia
Newly Renovated Condo - St. Martin Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $629 per night (USD)
Expedia
From $548 per night (USD)
VRBO
Fully Updated 2/2 Condo! The Grand Cayman Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $548 per night (USD)
VRBO
From $859 per night (USD)
Expedia
Casa Rosa: 4BR/4BA house, pool, near Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida. *Saturday-to-Saturday ...
From $859 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $450 per night (USD)
VRBO
From $410 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 $410 per night (USD)
Expedia
Click For Pricing
VRBO
Indoor / Outdoor Living in Old Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our home is down a quiet lane in the heart of Key West. Walk to Duval Street, organic “fast food,” yoga, beer, fishin ...
Click For Pricing
VRBO
From $523 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 $523 per night (USD)
VRBO
From $1165 per night (USD)
VRBO
**CASA AMARILLA @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $1165 per night (USD)
VRBO
From $323 per night (USD)
Expedia
**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR/2BA Cottage + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You have many ...
From $323 per night (USD)
Expedia
From $198 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 $198 per night (USD)
VRBO
From $475 per night (USD)
VRBO
Foundry 7 - Historic Luxury in the Heart of Key West
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 $475 per night (USD)
VRBO
From $330 per night (USD)
VRBO
THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $330 per night (USD)
VRBO
From $612 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 $612 per night (USD)
Expedia
From $1115 per night (USD)
VRBO
JASMINE PLACE:1 block to Duval - Private Pool - Parking! - RealKeyWest
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
WELCOME TO JASMINE PLACE! Jasmine Place is a beautiful and enchanting home conveniently located next door to the Ernes ...
From $1115 per night (USD)
VRBO
From $487 per night (USD)
Expedia
Classic Key West living w/ a full kitchen, balcony, & shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Baya House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $487 per night (USD)
Expedia
From $386 per night (USD)
VRBO
~Reel Paradise~Beautiful private townhouse in a small gated community.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $386 per night (USD)
VRBO
From $1121 per night (USD)
Expedia
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
PROPERTY: Enjoy your coffee on the front porch or listen to the birds while gliding on the swing. Either way, you will a ...
From $1121 per night (USD)
Expedia
From $1165 per night (USD)
VRBO
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 $1165 per night (USD)
VRBO
From $1559 per night (USD)
Expedia
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 $1559 per night (USD)
Expedia
From $1220 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 $1220 per night (USD)
VRBO
From $939 per night (USD)
Expedia
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 $939 per night (USD)
Expedia
From $326 per night (USD)
VRBO
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 $326 per night (USD)
VRBO
From $469 per night (USD)
Expedia
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 $469 per night (USD)
Expedia
From $1239 per night (USD)
VRBO
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 $1239 per night (USD)
VRBO
From $1368 per night (USD)
Expedia
LADY ADMIRAL ~ Sweet cottage & guest house with private 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 $1368 per night (USD)
Expedia
From $1025 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 $1025 per night (USD)
VRBO
From $3316 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 $3316 per night (USD)
Expedia
From $1080 per night (USD)
VRBO
SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Annex Home w/Private Heated Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $1080 per night (USD)
VRBO
From $407 per night (USD)
Expedia
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through April 2026. A ...
From $407 per night (USD)
Expedia
From $517 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 $517 per night (USD)
VRBO
From $1114 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 $1114 per night (USD)
Expedia
From $680 per night (USD)
VRBO
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through April 2026. A ...
From $680 per night (USD)
VRBO
From $420 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 $420 per night (USD)
Expedia
$\LA DOLCE VITA\, OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!$
From $381 per night (USD)
VRBO
\"LA DOLCE VITA\", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
'La Dolce Vita' is located in Old Town, Key West!! Just 3 short blocks to Southernmost Beach and Southernmost Point ...
From $381 per night (USD)
VRBO
From $332 per night (USD)
Expedia
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ADORIABLE RETREAT ONE BLOCK FROM DUVAL… One bedroom gem on Simonton Street one block from Duval. One bedroom, one bathr ...
From $332 per night (USD)
Expedia
From $613 per night (USD)
VRBO
Hyatt Windward Pointe 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hyatt Windward Pointe in Key West is a tranquil resort offering a luxurious escape on the island’s serene southeast coas ...
From $613 per night (USD)
VRBO
Click For Pricing
Expedia
Luxurious top floor, end unit, within premier resort on the Atlantic Ocean.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax in style at the Hyatt Windward Pointe Resort. This is the best location within the resort: Top floor, end unit. Lo ...
Click For Pricing
Expedia
From $286 per night (USD)
VRBO
Gulf Getaway | Condo w/Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 ...
From $286 per night (USD)
VRBO
From $881 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 $881 per night (USD)
VRBO
From $642 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 $642 per night (USD)
VRBO
From $566 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 $566 per night (USD)
Expedia
From $1066 per night (USD)
VRBO
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $1066 per night (USD)
VRBO
From $1074 per night (USD)
Expedia
Washer & Dryer, Near Downtown - The Mesa House
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $1074 per night (USD)
Expedia
From $776 per night (USD)
VRBO
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $776 per night (USD)
VRBO
From $239 per night (USD)
Expedia
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 $239 per night (USD)
Expedia
From $153 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 $153 per night (USD)
VRBO
From $417 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 $417 per night (USD)
Expedia
From $179 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 $179 per night (USD)
VRBO
From $541 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 $541 per night (USD)
Expedia
From $954 per night (USD)
VRBO
Balcony & Near Downtown - Cloud Suite on Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Cloud Suite On Duval is a beautifully updated 2 bed, 2.5 bath upper level condo located right in the heart of w ...
From $954 per night (USD)
VRBO
From $397 per night (USD)
Expedia
GARDEN HIDEAWAY ~ Beautiful lush landscaped oasis located in the Casa Marina!
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 ...
From $397 per night (USD)
Expedia
From $335 per night (USD)
VRBO
THE MANGO TREE COTTAGE - Old Town Key West, Steps to Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Mango Tree Cottage – Old Town Key West Gem! Location, Location, LOCATION! Welcome to The Mango Tree Cottage, your ...
From $335 per night (USD)
VRBO
From $457 per night (USD)
Expedia
A PEACE OF PARADISE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with fla ...
From $457 per night (USD)
Expedia
From $797 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 $797 per night (USD)
VRBO
From $313 per night (USD)
Expedia
**SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SERENITY ON S ...
From $313 per night (USD)
Expedia
From $351 per night (USD)
VRBO
PEAK OF DUVAL | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $351 per night (USD)
VRBO
From $844 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 $844 per night (USD)
VRBO
From $2064 per night (USD)
VRBO
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 $2064 per night (USD)
VRBO
From $389 per night (USD)
VRBO
Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
Bedrooms:
1
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 $389 per night (USD)
VRBO
From $530 per night (USD)
VRBO
Roosters Perch at Truman Annex- LOW SUMMER RATES!!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Roosters Perch in Truman Annex, Porter Lane! This spacious corner duplex is flooded with natural light and b ...
From $530 per night (USD)
VRBO
From $683 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 $683 per night (USD)
VRBO
$\Tranquility \ At Ann Street Gardens Steps From Duval$
From $671 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 $671 per night (USD)
VRBO
From $262 per night (USD)
Expedia
Avail Oct 25 &26. fantasy fest parade Oct 25. grab it now before gone!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR STORM POLICIES ...
From $262 per night (USD)
Expedia

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