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From $1902 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 $1902 per night (USD)
VRBO
From $879 per night (USD)
Expedia
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 $879 per night (USD)
Expedia
From $657 per night (USD)
VRBO
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 $657 per night (USD)
VRBO
From $681 per night (USD)
Expedia
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 $681 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Hidden Beach Unit 1. The perfect place to stay in Key West for less
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Hidden Beach Unit 1 - Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach ...
From $538 per night (USD)
VRBO
From $345 per night (USD)
Expedia
SHADY NOOK at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Two blocks away from Duval Street with direct access to Thomas Street through the rear gate. Has free hook up for intern ...
From $345 per night (USD)
Expedia
From $244 per night (USD)
VRBO
A PALM TREE PARADISE @ the Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A Palm tree Paradise***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***Stay on the only 18-hole golf club in the Florida Key ...
From $244 per night (USD)
VRBO
From $376 per night (USD)
Expedia
ROYAL POINCIENA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $376 per night (USD)
Expedia
From $911 per night (USD)
VRBO
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 $911 per night (USD)
VRBO
From $491 per night (USD)
Expedia
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 $491 per night (USD)
Expedia
From $657 per night (USD)
VRBO
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 $657 per night (USD)
VRBO
From $378 per night (USD)
Expedia
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 $378 per night (USD)
Expedia
From $681 per night (USD)
VRBO
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 $681 per night (USD)
VRBO
From $323 per night (USD)
Expedia
A SANCTUARY HOME at the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Sanctuary Home*****PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***** | Stay on the only 18-hole golf club in the Florida ...
From $323 per night (USD)
Expedia
From $442 per night (USD)
VRBO
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautiful gated home is located on an oversized corner lot a few blocks from White Street Pier and Higg's Beach wit ...
From $442 per night (USD)
VRBO
From $466 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 $466 per night (USD)
Expedia
From $420 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 $420 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 $538 per night (USD)
VRBO
Oceanfront Hidden Beach Unit 2 - The best place to stay in Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlan ...
From $538 per night (USD)
VRBO
From $677 per night (USD)
Expedia
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 $677 per night (USD)
Expedia
From $457 per night (USD)
VRBO
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 $457 per night (USD)
VRBO
From $3892 per night (USD)
Expedia
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 $3892 per night (USD)
Expedia
From $1996 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 $1996 per night (USD)
VRBO
From $287 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 $287 per night (USD)
Expedia
From $426 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 $426 per night (USD)
VRBO
From $469 per night (USD)
Expedia
~ 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 $469 per night (USD)
Expedia
From $418 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 $418 per night (USD)
VRBO
From $635 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 $635 per night (USD)
Expedia
From $608 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 $608 per night (USD)
VRBO
From $632 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 $632 per night (USD)
Expedia
From $744 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 $744 per night (USD)
VRBO
From $390 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 $390 per night (USD)
Expedia
From $632 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 $632 per night (USD)
VRBO
From $210 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 $210 per night (USD)
Expedia
From $823 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 $823 per night (USD)
VRBO
From $187 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 $187 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 $256 per night (USD)
Expedia
Sea Breeze at 1800 Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sea Breeze at 1800 Atlantic is a two bedroom / two bathroom fully furnished condo located in the East Tower on the top f ...
From $256 per night (USD)
Expedia
From $548 per night (USD)
VRBO
Balcony, Pool, & Pet Friendly - 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 $548 per night (USD)
VRBO
From $630 per night (USD)
Expedia
Newly Updated! 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 $630 per night (USD)
Expedia
From $450 per night (USD)
VRBO
BEACHFRONT-Coconut Beach Resort, 7 nights, May 10-17, or May 31-June 7, only.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Private tropical Paradise on the Atlantic Ocean in Key West, Florida. This condo unit is a 1 bedroom, with 2 full bathro ...
From $450 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
$Amazing Stay w\/ Fantastic View in Key West! 3 Convenient Rooms, Outdoor Pool$
From $697 per night (USD)
VRBO
Amazing Stay w\/ Fantastic View in Key West! 3 Convenient Rooms, Outdoor Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $697 per night (USD)
VRBO
From $242 per night (USD)
Expedia
Your Next Getaway is Here! Deluxe Fantastic View Two Queen Beds, Outdoor Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $242 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 $721 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 $721 per night (USD)
Expedia
From $1064 per night (USD)
VRBO
4x Pool View Two Queen Beds at The Gates Hotel Key West, Onsite Swimming Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1064 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Standard Two Queen Beds at The Gates Hotel Key West, Onsite Pool, Bike Rental!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $246 per night (USD)
Expedia
From $987 per night (USD)
VRBO
Key West Dream! 4 Serene Units, Pool, Restaurant, Parking, Gym!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $987 per night (USD)
VRBO
From $1064 per night (USD)
Expedia
Escape to the Keys! 4 Amazing Units, Pool, Restaurant, On-Site Bar, Parking!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1064 per night (USD)
Expedia
From $532 per night (USD)
VRBO
2x Pool View Two Queen Beds Rooms at The Gates Hotel Key West!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $532 per night (USD)
VRBO
From $987 per night (USD)
Expedia
4 Standard 2 Queens Rooms at The Gates Hotel Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $987 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Welcome to a Sun-Soaked Paradise! Discover the History and Soul of Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $266 per night (USD)
VRBO
From $494 per night (USD)
Expedia
Key West Dream! 2 Awesome Units, Pool, Restaurant, Bar, Bike Rentals, Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $494 per night (USD)
Expedia
From $246 per night (USD)
VRBO
Key West Getaway! Pool, Restaurant, Bar, Gym, Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $246 per night (USD)
VRBO
From $740 per night (USD)
Expedia
3 units, 2 Queens Rooms With Garden View at The Gates Hotel Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $740 per night (USD)
Expedia
From $532 per night (USD)
VRBO
Tropical Experience! 2 Gorgeous Units, Restaurant, Bar, Pool, Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $532 per night (USD)
VRBO
From $798 per night (USD)
Expedia
4x Pool View Two Queen Beds at The Gates Hotel Key West, Onsite Swimming Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $798 per night (USD)
Expedia
From $899 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 $899 per night (USD)
VRBO
From $246 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 $246 per night (USD)
Expedia
From $968 per night (USD)
VRBO
Perfect Key West Staycation Perfect For Your Family! Four Relaxing Rooms, Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $968 per night (USD)
VRBO
From $277 per night (USD)
Expedia
~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 $277 per night (USD)
Expedia
From $689 per night (USD)
VRBO
~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 $689 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Looking for Relaxing Location for Your Next Getaway? Premium Ocean View Room
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $260 per night (USD)
Expedia
From $429 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 $429 per night (USD)
VRBO
$\LA DOLCE VITA\, OLD TOWN!! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!$
From $405 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 $405 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
From $357 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo w/ a patio at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $357 per night (USD)
Expedia
From $233 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 $233 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 $691 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 $691 per night (USD)
VRBO
From $917 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 $917 per night (USD)
Expedia
From $362 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 $362 per night (USD)
VRBO
Click For Pricing
Expedia
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For Pricing
Expedia
From $737 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 $737 per night (USD)
VRBO
From $393 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 $393 per night (USD)
Expedia
From $964 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 $964 per night (USD)
VRBO
From $431 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 $431 per night (USD)
Expedia
From $254 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 $254 per night (USD)
VRBO
From $275 per night (USD)
Expedia
THE MANGO TREE COTTAGE - Old Town Key West, Steps to Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Location, Location, LOCATION!!! Perfectly located in Old Town Key West, this beautifully remodeled 3 bedroom, 2 bathroom ...
From $275 per night (USD)
Expedia
From $307 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 large corner duplex is full of natural light and windows. ...
From $307 per night (USD)
VRBO
$Spec.@135 + extras 6-30 to 7-3 Close to beach plus kitchen\n$
From $194 per night (USD)
Expedia
Spec.@135 + extras 6-30 to 7-3 Close to beach plus kitchen\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $194 per night (USD)
Expedia
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VRBO
One bedroom in the heart of downtown w/ kitchen
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Truman at Duval - Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
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VRBO
From $611 per night (USD)
Expedia
The Secret Grotto
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Welcome to The Secret Grotto! This spacious 3,300 square foot home is located on nearly a 5,000 square foot lot and fea ...
From $611 per night (USD)
Expedia
From $807 per night (USD)
VRBO
The Gideon Lowe House - Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $807 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Keys to Paradise - Shipyard Truman Annex - LOWEST RATES JUNE-SEPTEMBER!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex! This quaint, we ...
From $339 per night (USD)
Expedia
From $857 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 $857 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 $828 per night (USD)
VRBO
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 $828 per night (USD)
VRBO
From $834 per night (USD)
Expedia
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 $834 per night (USD)
Expedia
From $897 per night (USD)
VRBO
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 $897 per night (USD)
VRBO
From $852 per night (USD)
Expedia
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 $852 per night (USD)
Expedia
From $936 per night (USD)
VRBO
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 $936 per night (USD)
VRBO
From $1082 per night (USD)
Expedia
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 $1082 per night (USD)
Expedia
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Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
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Expedia
$June Spec 129.+\n6-15 til 6-19 NEWLY Redone. Not shown in current pics\n$
From $172 per night (USD)
Expedia
June Spec 129.+\n6-15 til 6-19 NEWLY Redone. Not shown in current pics\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
New Pics coming soon. GREAT LOCATION Close to beach and All! REASONABLE RATES. W. KITCHEN AND PATIO Come splash in ...
From $172 per night (USD)
Expedia
From $723 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 $723 per night (USD)
VRBO
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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 ...
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Expedia
From $658 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 $658 per night (USD)
VRBO
$Downtown Key West 2BR/2BA•Pool, Dock, Pet \Aruba\$
From $535 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 $535 per night (USD)
Expedia

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