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From $480 per night (USD)
VRBO
Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool
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 $480 per night (USD)
VRBO
From $1589 per night (USD)
Expedia
Oversized home for the whole family w/private pool & dock
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1589 per night (USD)
Expedia
From $488 per night (USD)
VRBO
HIGH TIDE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
If you have high expectations, you are going to enjoy staying at High Tide. You are within walking distance to restaura ...
From $488 per night (USD)
VRBO
From $497 per night (USD)
Expedia
A CONCH ESCAPE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Location, location, adorable two bedroom, one bath second floor condo overlooking the Truman Waterfront Park is the per ...
From $497 per night (USD)
Expedia
From $447 per night (USD)
VRBO
A SUNSET VIEW at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $447 per night (USD)
VRBO
From $606 per night (USD)
Expedia
GYPSY'S PALACE in the Truman Annex - Stunning ocean views!!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Fabulous waterfront two level condo in the beautiful Historic Mills Place Hospital Building in the Truman Annex awaits! ...
From $606 per night (USD)
Expedia
From $894 per night (USD)
VRBO
Spacious home with pool & balcony - 1 block from Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Last Minute Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $894 per night (USD)
VRBO
From $488 per night (USD)
Expedia
ARCHIPELAGO l at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $488 per night (USD)
Expedia
From $466 per night (USD)
VRBO
Location, Beauty & Comfort @ Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $466 per night (USD)
VRBO
From $1217 per night (USD)
Expedia
Oceanfront 4-Bed 3-Bath home with pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
4 Bedroom, 3 Bathroom, Sleeps 8 Luxurious furnishings and spacious interiors centered around the expansive water views p ...
From $1217 per night (USD)
Expedia
From $564 per night (USD)
VRBO
Alluring corner unit w/ full kitchen & pool - close to beach/ nightlife
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Seaclusion Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $564 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Wonderful Condo in Key West w/Free WiFi, Lanai, A/C, Shared Hot Tub & Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tradewinds at Smathers Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $267 per night (USD)
Expedia
From $932 per night (USD)
VRBO
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $932 per night (USD)
VRBO
From $453 per night (USD)
Expedia
Steps from Duval, Shared Pool – Sky Loft Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duv ...
From $453 per night (USD)
Expedia
From $3802 per night (USD)
VRBO
Takeover at the Grand Maloney
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Summary: The Grand Maloney Hotel is a boutique hotel located in the heart of downtown Key West. Our signature red brick, ...
From $3802 per night (USD)
VRBO
From $368 per night (USD)
VRBO
NEW LISTING 2nd Fl Condo w/private outdoor deck overlooking historic Fleming St.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Airy sun-filled apartment above an art gallery in 100 year old Old Town Conch home. Private cozy quiet & romantic hideaw ...
From $368 per night (USD)
VRBO
From $1354 per night (USD)
VRBO
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get the gang ...
From $1354 per night (USD)
VRBO
From $176 per night (USD)
Expedia
Sailor's Sanctuary - A Renovated Condo in Old Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Renovated ground floor apartment in Truman Annex. Steps from Duval Street! Enjoy all that the beautiful gated community ...
From $176 per night (USD)
Expedia
From $2074 per night (USD)
VRBO
Historic Old Town Key West - Main House, 4 beds, 1 Sleeper Sofa, Accommodates 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
OVERVIEW The 'Main House' is a two-story, four (4) bedroom, one and a half (1.5) bathroom renovated historic home. The ...
From $2074 per night (USD)
VRBO
From $1028 per night (USD)
Expedia
BLUE LAGOON at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second ...
From $1028 per night (USD)
Expedia
From $1136 per night (USD)
VRBO
ARCHIPELAGO in the Truman Annex
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everyt ...
From $1136 per night (USD)
VRBO
From $878 per night (USD)
Expedia
SUNSET DALITE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! | This gorgeous cond ...
From $878 per night (USD)
Expedia
From $862 per night (USD)
VRBO
AQUA BREEZE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $862 per night (USD)
VRBO
From $475 per night (USD)
Expedia
SHADY NOOK at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This 2 bedroom, 1 bath condo is a blend of Key West charm, modern comfort and unbeatable location! You'll enjoy bright, ...
From $475 per night (USD)
Expedia
From $482 per night (USD)
VRBO
ROYAL POINCIENA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in the heart of Old Town within the sought-after Shipyard community, this inviting second-floor condo offers the ...
From $482 per night (USD)
VRBO
From $930 per night (USD)
Expedia
A GULFSTREAM DRIFT at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise h ...
From $930 per night (USD)
Expedia
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 $1814 per night (USD)
VRBO
Features.Key West Suites Hotel has an outdoor pool and fitness center
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 ...
From $1814 per night (USD)
VRBO
From $383 per night (USD)
Expedia
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)
Expedia
From $216 per night (USD)
VRBO
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)
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 $474 per night (USD)
Expedia
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)
Expedia
From $1107 per night (USD)
VRBO
**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)
VRBO
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)
VRBO
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)
VRBO
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 $436 per night (USD)
VRBO
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)
VRBO
From $730 per night (USD)
Expedia
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)
Expedia
From $202 per night (USD)
VRBO
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)
VRBO
From $1096 per night (USD)
Expedia
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)
Expedia
From $288 per night (USD)
VRBO
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)
VRBO
From $371 per night (USD)
Expedia
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)
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 $450 per night (USD)
Expedia
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)
Expedia
From $859 per night (USD)
VRBO
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)
VRBO
Click For Pricing
Expedia
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
Expedia
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 $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 $487 per night (USD)
VRBO
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)
VRBO
$\LA DOLCE VITA\, OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!$
From $381 per night (USD)
Expedia
\"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)
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 $1066 per night (USD)
Expedia
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)
Expedia
From $1074 per night (USD)
VRBO
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)
VRBO
From $776 per night (USD)
Expedia
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)
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 $335 per night (USD)
Expedia
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)
Expedia
From $457 per night (USD)
VRBO
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)
VRBO
From $797 per night (USD)
Expedia
**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)
Expedia
From $313 per night (USD)
VRBO
**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)
VRBO
From $351 per night (USD)
Expedia
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)
Expedia
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 $612 per night (USD)
Expedia
The Secret Grotto
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Welcome to The Secret Grotto — Your Luxurious Tropical Escape! Step into this stunning 3,220-square-foot sanctuary nest ...
From $612 per night (USD)
Expedia
From $948 per night (USD)
VRBO
The Gideon Lowe House - Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegance. Sophistication. Perfection. Welcome to the Gideon Lowe House, a historic treasure in the heart of Old Town Ke ...
From $948 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Keys to Paradise – Your Cozy Retreat in the Heart of Key West! Located in the charming Shipyard Condominium ...
From $457 per night (USD)
Expedia
From $1258 per night (USD)
VRBO
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $1258 per night (USD)
VRBO
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Expedia
Oceanfront Condo at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You won't find a better steal than a high-season stay in this beautiful and spacious second-floor condo on the Hyatt Win ...
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Expedia
From $262 per night (USD)
VRBO
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)
VRBO
From $905 per night (USD)
Expedia
Waterfront Home in Key Cove Landings
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $905 per night (USD)
Expedia
From $1072 per night (USD)
VRBO
Waterfront luxury home with private pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your ...
From $1072 per night (USD)
VRBO
From $938 per night (USD)
Expedia
Luxury Waterfront Home with private pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $938 per night (USD)
Expedia
From $1292 per night (USD)
VRBO
Modern Waterfront Luxury Home with Heated Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for a luxury escape on the water, Paris Mango is your island gem. Named after Jimmy's "Last Mango in P ...
From $1292 per night (USD)
VRBO
$Sept.mid wk.spec.117. lod +\n10 min walk beach, close to all +\nfull kitch& patio$
From $255 per night (USD)
Expedia
Sept.mid wk.spec.117. lod +\n10 min walk beach, close to all +\nfull kitch& patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
SUMMER SPECIAL August and September Most dates @ 107. lodging plus extras per night. With 4 night stay 5th night FREE ...
From $255 per night (USD)
Expedia
From $1131 per night (USD)
VRBO
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $1131 per night (USD)
VRBO
From $1197 per night (USD)
Expedia
Conch style home in Oldtown with private pool AND dock!
Bedrooms:
3
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 $1197 per night (USD)
Expedia
From $1335 per night (USD)
VRBO
Luxury Waterfront Home with Private Pool and Dock!
Bedrooms:
3
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 $1335 per night (USD)
VRBO
Click For Pricing
Expedia
Two Bedroom Condo, Key West, Ocean View 3054374
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hyatt Residence Club Key West – Windward Pointe Two Bedroom Condo – Partial Ocean Views Partial ocean views and lavish ...
Click For Pricing
Expedia
From $710 per night (USD)
VRBO
Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home - Stay spacious in Key West. Boat ...
From $710 per night (USD)
VRBO
$Downtown Key West 2BR/2BA•Pool, Dock, Pet \Aruba\$
From $791 per night (USD)
Expedia
Downtown Key West 2BR/2BA•Pool, Dock, Pet \"Aruba\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Enjoy true space in Key West! This 1,200 sq ft waterfront condo offers a full kitchen, dining area, living room ...
From $791 per night (USD)
Expedia
From $1744 per night (USD)
VRBO
St. Johns Waterfront 4BR Penthouse•Pool•Dock•Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring the whole crew to this 2200 sqft waterfront penthouse—perfect for families & large groups! With 4 bedroom ...
From $1744 per night (USD)
VRBO
$Old Town \Eleuthera\ • 2BR Waterfront Corner Condo$
From $702 per night (USD)
Expedia
Old Town \"Eleuthera\" • 2BR Waterfront Corner Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just ...
From $702 per night (USD)
Expedia
From $162 per night (USD)
VRBO
Sunny Apartment with a Large Deck and Great View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming 1 bedroom second floor apartment with a large deck space for dining, sunbathing or watching sunsets. In residen ...
From $162 per night (USD)
VRBO
Click For Pricing
Expedia
Hyatt Residence Club Windward Pointe Key West 2br/2ba/6ppl
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT Windward Pointe. Sleeps 6 people. 2 bedrooms (1King/1Quee ...
Click For Pricing
Expedia
From $369 per night (USD)
VRBO
Pool & Parking, & Pet Friendly - Hidden Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Hidden Oasis is a 28-night minimum rental, offering contemporary luxury in the heart of Midtown, Key West. It’s ...
From $369 per night (USD)
VRBO
From $294 per night (USD)
Expedia
Charming, updated home near Duval St. with enclosed patio & walkable location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Coral Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $294 per night (USD)
Expedia

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