Key West Rentals
From $1188 per night (USD)VRBO
Ultimate Key West Adventure! 3 Serene Units, Pool, Parking, Bar, Restaurant!
- 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 $1188 per night (USD)VRBO
From $491 per night (USD)VRBO
King Bed Accommodation at The Gates Hotel Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $491 per night (USD)VRBO
From $2310 per night (USD)VRBO
Paradise Found! 4 Awesome Units, Pool, Parking, Restaurant, Bar, 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 $2310 per night (USD)VRBO
From $2270 per night (USD)VRBO
Escape to the Keys! 4 Great Units, Pool, Restaurant, On-Site Bar, Gym, 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 $2270 per night (USD)VRBO
From $489 per night (USD)VRBO
Escape to the Beach! Pool, Restaurant, Gym, Bike Rentals, Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $489 per night (USD)VRBO
From $1147 per night (USD)VRBO
Exciting Tropical Vacation! 2 Great Units Near The Key West Lighthouse, Pool!
- 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 $1147 per night (USD)VRBO
From $1122 per night (USD)VRBO
Paradise Getaway! 2 Beautiful Units! Shuttle, Gym, Parking, and On-Site Bar!
- 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 $1122 per night (USD)VRBO
From $1122 per night (USD)VRBO
Tropical Experience! 2 Amazing 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 $1122 per night (USD)VRBO
From $1732 per night (USD)VRBO
Key West Escape! 3 Gorgeous Units, Pool, Restaurant, Bike Rental, Gym, Parking!
- 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 $1732 per night (USD)VRBO
From $1694 per night (USD)VRBO
Beach Adventure Awaits! 3 Amazing Units, Pool, Parking, Gym, Bar and Restaurant!
- 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 $1694 per night (USD)VRBO
From $561 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 $561 per night (USD)VRBO
From $573 per night (USD)VRBO
Best Vacation Awaits! Near Key West Butterfly, Pool, On-site Bar
- 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 $573 per night (USD)VRBO
From $506 per night (USD)VRBO
Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $506 per night (USD)VRBO
From $2270 per night (USD)VRBO
Tropical Escape! 4 Amazing Units for Large Groups, Pool, 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 $2270 per night (USD)VRBO
From $181 per night (USD)VRBO
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This freshly ...
From $181 per night (USD)VRBO
From $1140 per night (USD)Expedia
Poolside Paradise- Updated Home in PERFECT Spot!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: This 3 bed 2 bath home with a private amazing pool is located right off the quieter end of Duval St. The home c ...
From $1140 per night (USD)Expedia
From $414 per night (USD)VRBO
Poolside Retreat- Tropical Cottage with Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled g ...
From $414 per night (USD)VRBO
From $230 per night (USD)Expedia
Upscale end unit home @ Truman Annex close to Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $230 per night (USD)Expedia
From $334 per night (USD)VRBO
New listing! Newly-remodeled family home w/ a private, heated pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $334 per night (USD)VRBO
From $1525 per night (USD)VRBO
Old Town Retreat near Upper Duval St
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel wh ...
From $1525 per night (USD)VRBO
From $343 per night (USD)VRBO
Dog-friendly condo with shared pool, hot tub, and more - walk or bike to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Paradise Escape 407 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $343 per night (USD)VRBO
From $600 per night (USD)Expedia
Sea Breeze Cottage in Truman Annex Location! Location! Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the beautiful Truman Annex. Get ready ...
From $600 per night (USD)Expedia
From $261 per night (USD)VRBO
Location, location, location - Walk to the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $261 per night (USD)VRBO
From $255 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 the heart of Old Town Key West and just steps to Duval Street in the heart of the Historic ...
From $255 per night (USD)Expedia
From $431 per night (USD)VRBO
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We understand that these are unprecedented times and no one knows what tomorrow will bring. Here in Key West we believe ...
From $431 per night (USD)VRBO
From $410 per night (USD)Expedia
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
From $410 per night (USD)Expedia
From $1145 per night (USD)VRBO
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1145 per night (USD)VRBO
From $120 per night (USD)Expedia
New listing! Inviting condo with a private deck and shared swimming pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Shangri La Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $120 per night (USD)Expedia
From $410 per night (USD)VRBO
3 blocks from waterfront and 1 block off Duval in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
From $410 per night (USD)VRBO
From $296 per night (USD)Expedia
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $296 per night (USD)Expedia
From $225 per night (USD)VRBO
Galleon Resort available. 2/19/21-2/26/21
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
From $225 per night (USD)VRBO
From $241 per night (USD)Expedia
**BANYAN ROSE @ BEACHSIDE** Modern Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Nestled under ...
From $241 per night (USD)Expedia
From $850 per night (USD)VRBO
Coconut Palm- Island Home with NEW Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Coconut Palm is the perfect place for your beautiful tropical getaway in Key West. It is located just one block ...
From $850 per night (USD)VRBO
From $658 per night (USD)Expedia
Lazy Lane 261- Second Floor Home with Balcony!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Lazy Lane at the picturesque Shipyard Condominiums is just a few steps away from Fort Zachary Taylor Beach and ...
From $658 per night (USD)Expedia
From $926 per night (USD)VRBO
Casa Key West- Rooftop Pool Access & Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: This bright, spacious three bedroom condominium is the perfect Key West getaway. Located at Duval Square it is ...
From $926 per night (USD)VRBO
From $488 per night (USD)Expedia
Sea Breeze- Walking distance & Off-Street Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Sea Breeze is the perfect location for your tropical getaway! This two bedroom is located in the heart of Old T ...
From $488 per night (USD)Expedia
From $1325 per night (USD)VRBO
Coastal Comfort; Waterfront Luxury Home with private pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1325 per night (USD)VRBO
From $588 per night (USD)Expedia
Top Floor Ocean Views from every window Newly Renovated
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Key West Paradise Found hes been renovated for 2020 an ...
From $588 per night (USD)Expedia
From $293 per night (USD)VRBO
Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR/2BA in Old Town!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*** Located in the Old Town neighborhood. This exclusive residential area of Old Town Key West is really an extension of ...
From $293 per night (USD)VRBO
From $599 per night (USD)Expedia
Penthouse Level Ocean Views- Live the Dream
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY You feel the excitement the moment you arrive. The war ...
From $599 per night (USD)Expedia
From $1312 per night (USD)VRBO
Havana Daydream; Spacious Waterfront 4 Bedroom Home With Private Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life i ...
From $1312 per night (USD)VRBO
From $605 per night (USD)Expedia
Penthouse Level Ocean Views from every room Tropical Excellence
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Ocean views from every room with floor to ceiling wind ...
From $605 per night (USD)Expedia
From $1169 per night (USD)VRBO
Banana Breeze: Oceanview home with private pool and lush landscaping
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
"Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasi ...
From $1169 per night (USD)VRBO
From $600 per night (USD)Expedia
Hemingway Hideaway in Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Perfectly positioned townhouse in Truman Annex At Historic Foundry building. Hemingway Hideaway in Truman Annex is a de ...
From $600 per night (USD)Expedia
From $799 per night (USD)VRBO
NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Let us help make your dreams come true: Enjoy your tr ...
From $799 per night (USD)VRBO
From $250 per night (USD)Expedia
Sunset & Ocean View in Key West's Truman Annex, Bikes, Pool, Free WiFi & Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nice quiet vacation landing a few blocks from the action on Duval Street. This Saturday-Saturday home in Key West has: - ...
From $250 per night (USD)Expedia
From $225 per night (USD)VRBO
Beach House with Ocean View-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
If you are looking to stay in accommodations of high standards. This is the one for you! As you enter this large one bed ...
From $225 per night (USD)VRBO
From $187 per night (USD)Expedia
Old Town Island House Near a grocery store, beach, bike rental shop, Restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Two Story Apartment in central Old Town Key West location. Only a 5 min bike ride to Duval. 1 King size bed on 3rd flo ...
From $187 per night (USD)Expedia
From $291 per night (USD)VRBO
Castaway Cove - Kayaks, Heated Pool & Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Just steps from the coastal waterway and mangrove tunnels to explore, Castaway Cove has 4 kayaks included with ...
From $291 per night (USD)VRBO
From $307 per night (USD)VRBO
GREEN SPOT @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastef ...
From $307 per night (USD)VRBO
From $307 per night (USD)VRBO
ANOTHER THREE HOUR TOUR in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $307 per night (USD)VRBO
From $335 per night (USD)Expedia
Truman Annex Condo, Close to Beach & Duval with 2 Bikes, Upper level, Free WIFI!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! The Conch Retreat Condo is located in the Beautiful Shipyard of ...
From $335 per night (USD)Expedia
From $368 per night (USD)VRBO
**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Spanning an e ...
From $368 per night (USD)VRBO
From $368 per night (USD)Expedia
Conch House in the Historic District
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $368 per night (USD)Expedia
From $241 per night (USD)VRBO
Salt Pond Hideaway #133- Condo w/ Resort Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This spacious, airy rental is the perfect location for your Key West getaway! If you are looking to kick back a ...
From $241 per night (USD)VRBO
From $393 per night (USD)VRBO
ISLAND SPA in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing ...
From $393 per night (USD)VRBO
From $350 per night (USD)VRBO
Luxury Galleon Resort & Marina 2 Bed/2 Bath Marina View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
From $350 per night (USD)VRBO
From $307 per night (USD)VRBO
BLUE HEAVEN in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $307 per night (USD)VRBO
From $429 per night (USD)VRBO
A BELLA CAPRI at the beach - SUMMER SPECIAL
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...
From $429 per night (USD)VRBO
From $336 per night (USD)VRBO
OYSTER'S PEARL in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard back ...
From $336 per night (USD)VRBO
From $391 per night (USD)VRBO
**SOUTHERN STAR @ THE MEADOWS** 4BR Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERN STAR ...
From $391 per night (USD)VRBO
From $2421 per night (USD)Expedia
**THE LIME & THE COCONUT @ OLD TOWN** 6BR/6BA Compound + LAST KEY SERVICES..
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $2421 per night (USD)Expedia
From $550 per night (USD)VRBO
LATITUDE ADJUSTMENT at the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renov ...
From $550 per night (USD)VRBO
From $350 per night (USD)VRBO
ANOTHER DAY IN PARADISE in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $350 per night (USD)VRBO
From $829 per night (USD)VRBO
A SUNSET BREEZE Beautiful private home with pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Du ...
From $829 per night (USD)VRBO
From $350 per night (USD)VRBO
A SUNSET POOLSIDE in the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing FIRST FLOOR end unit features two bedrooms and TWO ensuite bathrooms with walk in showers. Each bedroom has ...
From $350 per night (USD)VRBO
From $408 per night (USD)VRBO
ARCHIPELAGO ll in the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This newer renovation is a gorgeous 2 bedroom, 2.5 bath townhouse. The kitchen and baths are new and living room, dining ...
From $408 per night (USD)VRBO
From $895 per night (USD)Expedia
Spacious, waterfront condo w/ a full kitchen, shared pool, & furnished balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunset at Harbour Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $895 per night (USD)Expedia
From $150 per night (USD)VRBO
The Marguerite, 603 #3 Elizabeth Street, Old Town Key West monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
One bedroom, One Bathroom apartment in Old Key West. It is located upstairs with an outside entrance and has dormer ceil ...
From $150 per night (USD)VRBO
From $152 per night (USD)Expedia
Poolside Paradise in Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the best of Key West! Poolside Paradise is located in the Key West Golf Club. Our townhome is located direc ...
From $152 per night (USD)Expedia
From $844 per night (USD)VRBO
Commodore's Cove - Perfect Location! Pvt Hot Tub!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Commodore's Cove offers the best of Key West: a prime location and the amenities of home. Up to 12 can stay at ...
From $844 per night (USD)VRBO
From $1874 per night (USD)Expedia
Commodore's Compound - Epic Home with Pvt Hot Tub!
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 24
Summary: Welcome to Commodore's Compound - an incredible 8 bed, 7 bath home in prime location - just 1 short block from ...
From $1874 per night (USD)Expedia
From $867 per night (USD)VRBO
Seaport Suite- 2nd Story Hideaway w/ Balcony!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Situated in the heart of Old Town Key West, Seaport Suite is the perfect vacation spot for large groups of up t ...
From $867 per night (USD)VRBO
From $307 per night (USD)VRBO
SEASCAPE in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $307 per night (USD)VRBO
From $179 per night (USD)VRBO
@ March 2020 Key West Condo on the Ocean, bike ride to Old Town Key West@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated 2 bedroom 2 bath condo with island views located on the Atlantic ocean. Top of the line finishes. ...
From $179 per night (USD)VRBO
From $1009 per night (USD)Expedia
Helen's Hideaway- Hidden Oasis with Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This corner hideaway is in a prime location, has a private heated pool and parking! Just 1 block from Duval nes ...
From $1009 per night (USD)Expedia
From $336 per night (USD)VRBO
TROPICAL VINEYARD in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $336 per night (USD)VRBO
From $336 per night (USD)VRBO
ALHAMBRA in the Truman Annex Compass Realty
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $336 per night (USD)VRBO
From $415 per night (USD)VRBO
SAILOR'S STORY in the Truman Annex
- Bedrooms:
- 3
- 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 $415 per night (USD)VRBO
From $393 per night (USD)Expedia
AQUA OASIS in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $393 per night (USD)Expedia
From $571 per night (USD)VRBO
CONCH ISLAND @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $571 per night (USD)VRBO
From $399 per night (USD)Expedia
*Casa-Amelia-Key-West* 1/2 block off Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your home away from home! Casa Amelia is a charming Conch house in the historic Gato Cigar Village. Wake up ...
From $399 per night (USD)Expedia
From $495 per night (USD)VRBO
Peachy Keen (New Listing) Wifi - Private Pool near Truman Annex - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful home has 4 bedrooms and 3 baths. There is a private and heated pool, a separate entrance for one of th ...
From $495 per night (USD)VRBO
From $2421 per night (USD)Expedia
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Large Pool + LAST KEY SERVI
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The vacation ...
From $2421 per night (USD)Expedia
From $357 per night (USD)VRBO
ADRIFT in Key West at the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stunning, Modern Nautical-themed 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completel ...
From $357 per night (USD)VRBO
From $195 per night (USD)Expedia
Luxurious Key West Pool Home block from Duval! Pool & Patio Recently Renovated!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Old Town refuge barely a block from world famous Duval Street with glimpse of Key West Light House! Located in the Histo ...
From $195 per night (USD)Expedia
From $522 per night (USD)VRBO
FOREVER YOUNG in the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $522 per night (USD)VRBO
From $336 per night (USD)VRBO
ABOUT TIME in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $336 per night (USD)VRBO
From $307 per night (USD)VRBO
HAVANA VIEWS in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $307 per night (USD)VRBO
From $293 per night (USD)VRBO
SAND CRAB CABANA in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $293 per night (USD)VRBO
From $731 per night (USD)VRBO
Blue Moonshine on the Atlantic many luxury finishes. Your Key West Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full siz ...
From $731 per night (USD)VRBO
From $441 per night (USD)Expedia
Quiet, elegant, Key West Condo close to the Ocean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all ...
From $441 per night (USD)Expedia
From $207 per night (USD)VRBO
The Estela, Old Town Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away just 1 block from the action of Duval Street lies our newest space located at 613 Fleming Street. Find your ...
From $207 per night (USD)VRBO
From $900 per night (USD)Expedia
Licence #CND5403426 Apt A-401, 2022 IS THE FINAL YEAR.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2022 IS THE FINAL YEAR. This property will be listed with All Florida Keys Vacation Rentals Effective Jan 1st 2023. ...
From $900 per night (USD)Expedia
From $350 per night (USD)VRBO
Licence #CND5403292 Apt A-403, 2022 IS THE FINAL YEAR.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2022 IS THE FINAL YEAR. This property will be listed with All Florida Keys Vacation Rentals Effective Jan 1st 2023. ...
From $350 per night (USD)VRBO
From $350 per night (USD)Expedia
Direct Ocean View from Your Condo-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom ...
From $350 per night (USD)Expedia
From $350 per night (USD)VRBO
Downtown Cottage just off famous Duval Street-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $350 per night (USD)VRBO
From $413 per night (USD)Expedia
Condo 2 br, Ocean view from Balcony, Top Floor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This condo is privately owned and managed. No condo fees. Condo's features two bedrooms, with a king bed in the master b ...
From $413 per night (USD)Expedia
From $179 per night (USD)VRBO
Private Home- Sun-filled Pool- Neighborhood Water Inlet-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and c ...
From $179 per night (USD)VRBO
From $594 per night (USD)VRBO
Portside Villa⚓️☀️🐬
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Portside Villa, a multi-million dollar old town treasure Vacation Townhouse for rent by the month Welcome to the m ...
From $594 per night (USD)VRBO