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Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, a private pool, a furnished patio, two full...
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...
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...
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...
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....
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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.
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...
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...
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...
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.
R2p4XzNfMnVuother travellers have booked this property
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...
Enjoy your private front porch in this quiet neighborhood in Old Town Key West.
Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home.
There is a potential deck work scheduled for sometime in August and part of September which will not affect pool usage...
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.
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....
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
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...
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...
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...
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...
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....
bVlwXzFfYXowother 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...
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.
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!...
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...
Duval Square Penthouse R19
Surround yourself with the historic charms of Key West at this dog-friendly penthouse, a spacious South Florida escape with a private hot tub, a deck and balcony for evening cocktails, and access to a lovely community swimming pool.
You'll find this comfortable condo...
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...
Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle townhome within easy walking distance to everything!
Meticulously decorated with art from local galleries and artists, you’ll be greeted by the super-sized sea turtle...
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...
Located right around the corner from Banana Cafe and Duval Street ,but still offering plenty of privacy, this cozy cottage with fully fenced yard makes a perfect rental for a small family or few friends trying to make the best of Key West!
An absolute jewel of a Key West vacation home a few...
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,...
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...
Duval Street Retreat
Stay in style in the heart of Key West's historic downtown, where you're steps from the beach and all Duval Street has to offer! Your back patio houses a private hot tub, dog-friendly accommodations, and grill, perfect for lounging with the group after a long day of play....
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...
Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool.
Ecco Domani means 'Here Tomorrow' which is where you'll want to be when you see what you're missing. A beautiful 3 story home with private pool, off...
Casa Bonita * Duval Square R1
Experience all that Old Town Key West has to offer at this beautiful, roomy condo located right off Duval Street. Featuring a large, shared swimming pool, lush, tropical gardens, private, covered parking, and space for up to six lucky guests, this vacation rental is...
*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...
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...
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...
Perfectly located and fully remodeled in 2018, Octopus's Garden is steps from Duval Street and the home of Ernest Hemmingway.
The homes historical outer appeal gives way to a modern designed interior that is furnished to perfection!
This stunning 3 bedroom / 3 bathroom features a formal...
*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,...
You will love this quiet tree-top studio in the heart of Old Town Key West. Located just a block away from the Historic Light house and Hemingway house and very close to Duval Street. This is a cosy studio ideal for one person or a couple looking for a reasonable Key West get-away. There is...
The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street.
Once here, you can settle in like a local as everything is within walking or biking distance. Imagine walking around the corner to grab a delectable key lime pie at Blue...
CONCH WIND - Stop searching, Conch Wind is the rental home in Key West you have been hunting for!
This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound. Plenty of space, beautifully furnished with all attention given to your comfort and...
As you step through the natural wooden gate onto the brick pathway, you will be embraced by this private garden oasis. Tranquility will overcome you as you pass Buddha, smile at the 'just perfect size' pool and you ring the bronze temple bell each time you enter and channel Hemingway's 'For Whom...
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...
Casa Caribe * Duval Square R9
Bask in the allure of old town Key West at this dog-friendly condo, where you'll have a private hot tub and deck, a community swimming pool, and enviable access to beaches, shops, and wonderful restaurants.
Located mere steps from Duval Street and verdant tropical...
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...
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...
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...
Yellowfin Ledge On Duval
Explore Key West with this conveniently located, dog-friendly condo as your home base!
Duval Street's famous array of bars, shopping, and eateries is just outside your door. Explore the neighborhood's historic sights like the Ernest Hemingway House, about five blocks...