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This is a truly rare find! And we know as we have been searching high and low for 5 years across Key West until we were ready to commit to this absolutely stunning property!
This is a privately owned townhouse within the exclusive resort of Santa Maria Suites. Not only is it rare to find a...
La Dolce Vita is just steps to Duval Street!
'La Dolce Vita' is beautiful and is a totally renovated condo.
Please check out our calendars for availability, photos and video.
Everything is brand new from floor to ceilings! 14 foot high ceilings with back lit crown molding in...
Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer....
Up to four guests can enjoy all the fun of Key West at this updated home complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! Dogs are allowed...
This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical...
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Amenities & Details
About this property
This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet...
b01NXzFfTXNhother traveller has booked this property
Amenities & Details
Private Outdoor Pool (Heated)
About this property
A Key Escape
Escape to the Florida Keys for a relaxing vacation in this three-bedroom, two-and-a-half bath home for eight (six comfortably) with a private pool and walking distance to the beach and Duval Street. And your favorite canine friend is also welcome for a small nightly fee.
Private Historic Bahama Conch Home in Old Town Key West.
Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga...
Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions!
CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located...
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower.
NjVuXzFfMmVsother traveller has booked this property
Amenities & Details
Shared Outdoor Pool (Unheated)
About this property
The Galleria - Andy's Attic
Take your romantic getaway at this bright studio condo in the heart of Key West's historic Old Town! Free WiFi, a deck, and a kitchenette will have you feeling right at home less than a mile from the beach.
Visit Fort Zachary Taylor State Park & Beach, about a mile...
Tropical Village Hideaway
Treat your group to a tropical getaway at this dog-friendly Key West retreat. Featuring room for up to six guests and a cute canine companion (for a small nightly fee), street parking, a private hot tub, and a shared pool, your vacation promises to be one to remember....
Privacy meets convenience at this beautiful Key West vacation rental, which features a two-bedroom, two-bathroom home, a separate studio cottage, a private pool, and room for up to eight guests. The family dog is also welcome to join you for an additional nightly fee.
Old Town Garden Villas - Bermuda Suite
Book your romantic escape to this dog-friendly Key West home. With access to a shared pool and a great location on Duval Street, you'll be able to slip into vacation mode in no time.
Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am...
Old Town Garden Villas - Andros Suite
Book your well-deserved getaway to this dog-friendly Key West home. With a prime central location near Duval Street and access to a shared pool, this home will let up to four guests and your happy puppy (for a small nightly fee) unwind in style.
Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home. This tropically inspired three level property has all the updated amenities for you and your guests to enjoy, plus be within walking distance of the Southernmost Point, the Hemingway...
Old Town Garden Villas - Little Havana Suite
Slip into vacation mode at this dog-friendly Key West cottage. Featuring room for up to four people, two levels, a shared pool, and easy access to all of the seaside action, this home promises to make your next vacation fun-filled and hassle-free!...
Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental
Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!
Enjoy the great location of this beautiful 2 bedroom 2.5 bath vacation home key west located in the gated rooftop community...
Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home.
Papa's Hideaway #3 - For Whom the Bell Tolls
Enjoy that next romantic getaway in Key West at this adorable and colorful ground-floor studio complete with a well-equipped kitchenette and view of the well-maintained courtyard and shared heated pool. Please note that off-street parking is available at...
Old Town Garden Villas - Caribbean Suite
Book your romantic retreat to this dog-friendly Key West cottage. Enjoy the shared pool and a great location off of Duval Street.
Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am
Located a few blocks from the Florida Keys...
Pescado Penthouse On Duval
Stay in style in the heart of Key West, where your balcony overlooks the colorful main drag! This home has dog-friendly accommodations for a small nightly fee.
This condo faces historic Duval Street, where you'll find some of Key West's most exciting shopping and...
Tropical Village -Southern Cross
Treat the whole family to a seaside adventure when you book your getaway to this dog-friendly Key West cottage. Boasting a prime location close to beach activities and attractions, as well as a shared pool, this home welcomes up to six guests and a canine companion...
Casa Cubana * Duval Square R14
Find a colorful, comfortable escape in the heart of Key West at this two-bedroom condo, where you'll enjoy a private deck and balcony, a community swimming pool, and easy access to beaches and downtown.
This well-appointed condo sits in the heart of historic Key...
Truman * Duval - Unit B
Enjoy this one bedroom apartment for your next getaway to Key West! Perfect for couples, this romantic spot is newly remodeled and will provide everything you need for a quick weekend escape! Beach towels are provided for your use.
Located in the heart of...
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.
This charming home features a gorgeous, open floor plan, a heated, outdoor pool, beautiful landscaping, an adorable front porch for...
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.*
This four-bedroom Key West home has just what you need for an awe-inspiring Florida beach getaway, including a private heated pool,...
Kate's Krawl Off Duval
The sunny paradise of Key West beckons, and this dog-friendly home is the perfect place to stay, with a private patio ensuring relaxation is never far away.
Located just steps from desirable Duval Street, this home makes it easy to experience all the best attractions in...
Truman * Duval - Studio A
Suprise your special someone with a stay at this charming and colorful Key West retreat! Set right in the heart of downtown, this home offers the perfect opportunity to enjoy a sun-kissed vacation you'll never forget.
Located steps from the intersection of Truman Avenue...
Enjoy the tropical ambience of this studio-style Key West cottage, where you'll find a private patio, dog-friendly accommodations, and a perfect location for dining, shopping, and exploring the local beaches and nightlife.
This sweet yellow cottage is located in a small complex that...
You'll settle into island life instantly at this two-bedroom, two-and-a-half-bathroom townhouse in Key West. With a private pool and lush garden in the backyard, a full kitchen, and a great location near the beach, comfort is never far away from your explorations.
Located on the...
This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer.
Quaint and charming, with a view of the...
Take a remarkable retreat to Key West with this one-bedroom, one-bathroom cottage with a shared pool, and a great central location on the island!
Sitting in a quiet location just off Truman Avenue and a few blocks down from Duval Street, you'll be within walking distance of any...
A Tropical Paradise on the Atlantic Ocean in Key West, Florida, this one-bedroom, one-bathroom suite is located at the historic Coconut Beach Resort.
Hidden from the street, on the quiet side of the island is the perfect blend of old island architecture, lush vegetation and walkways flowing onto...
After a long day cool off in your private pool, enjoy cold Mojitos on the covered porch and cook up some fresh grouper on the grill! Welcome to your dream vacation home!
The Amelia home is a 2 bedroom 2.5 bath retreat with sparkling private pool that is only four blocks from the Atlantic Ocean...
If you're planning your next family friendly group getaway or a large family reunion, this grouping of six separate Key West homes is the perfect spot for everyone to spread out and enjoy some privacy in a quiet residential neighborhood. Featuring street parking, a private pool,...
Enjoy a complimentary weekly boat ride around Key West on a 33' Cruisers Yacht with your stay. A tropical and light beachy property right on Duval St. perfect for all the entertainment during Fantasy Fest. This location is centered on Duval St. so either direction there is happening entertainment...
Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.
Key West Pinks, parties and drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway to Key West is...
Tropical Village Utopia
Get away from the stress of the daily grind with a trip to this contemporary Key West home. Offering street parking, access to a shared pool, room for up to four guests, and a charming island-themed ambiance, this home will make it easy to slip into vacation mode. The family...
Leeward Isle Key West Retreat – Location is everything! A hidden gem in the heart of Old Town Key West.
Nestled in a quiet and private gated oasis of only 13 properties, this townhome community is located right in the heart of Old Town. It’s the perfect location to stay and explore Key West....
Unwind in the heart of Key West's historic district with a dip in condo's hot tub ! The back patio here offers room to grill out and relax with your group after a long day enjoying all the island has to offer.
This suite is located on historic Duval Street, where you'll find some...
Tropical Village - Poolside Paradise
If you're looking for the perfect romantic escape for your next getaway, then look no further than this romantic Key West cottage. Featuring room for two guests to enjoy a shared pool and a location that puts you within easy reach of all of the local...
Casa Key West * Duval Square R32
Experience the beachy retreat you've been searching for at this dog-friendly Key West condo, where you'll enjoy a private balcony, a shared swimming pool, and a wonderful location for exploring.
Beautifully positioned to overlook the gardens of Duval Square, this...
This one-bedroom, one-bathroom condo in Key West, featuring entertainment, a wrap-around balcony, and beach access nearby! The family dog is also welcome to join you for an additional nightly fee.
Located on the corner of Duval Street and Amelia Street, you'll be close to all the...
Book this wonderful ground level Old Town cottage with all of the comforts of home and start your vacations off on the right foot! It features an open floor plan with doors that open to back patio to create indoor/outdoor living. Kick back in the living room area and watch your...
Do not look any further! Your perfect vacation home rental is right here! Offering private pool with lounge chairs and covered outside porch. You can also bring your Fido!
A distinctive private Key West vacation home with sparkling pool, Tropical Dreaming is the classic example of the best of...
If you're looking for a convenient home base for your Key West adventure, consider this two-bedroom, one-bathroom vacation rental. Up to six guests will enjoy the convenient location, a private hot tub, a fully equipped kitchen, and more! The family dog is also welcome to join...
Enjoy a complimentary boat ride weekly around Key West on a 33' Cruisers Yacht with your stay. A hidden Shangrila right on Duval St. perfect for your entertainment during Fantasy Fest. This location is centered on Duval St. so either direction there is some fun to be had during the day or night....