2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
This 2 bedroom, 2.5 bath rooftop town home is located within the quaint community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located right in the heart of old town Key West. Park your car in the ...
Property Type
Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
About this property
These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall.Inside, the comfortable ...
Property Type
Key West House
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
This charming one bedroom cottage is the perfect hideaway.The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, ...
Property Type
Key West House
4 BR | 4 BA | Sleeps 8 | Quick View
Key Amenities
About this property
On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool, or combines for a wonderful four bedroom retreat.Downstairs there is a large, open floor plan with living ...
Property Type
Key West House
2 BR | 1 BA | Sleeps 4 | Quick View
Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park
Key Amenities
About this property
$500 OFF ANY OF THESE WEEKS ONLY Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My over sized two bedroom, one bathroom ...
Property Type
Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island.Enjoy full use of direct TV channels, free current video library ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
This charming Key West cottage is just a short walk to a selection of great restaurants, art galleries, and shopping.Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets). The house can comfortably ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Open the door to Paradise Place and find yourself transported to a peaceful sanctuary.The downstairs living area is decorated with warm wood floors, blue and sand accents and provides plenty of space for entertaining. French doors lead out to a large covered and private patio area. The kitchen features ...
Property Type
Key West Condo
4 BR | 4 BA | Sleeps 8 | Quick View
Key Amenities
About this property
This huge penthouse condo, located just steps from the action of Duval Street, has been recently upgraded. This four-bedroom, 4.5 bath condo is in the heart of the action at Duval Square, a charming brick-paved and tree-lined courtyard just south of Truman Avenue. The residential units are on the second ...
Property Type
Key West Condo
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Tucked away near the quite end of Duval Street, you'll find this stylish, newly renovated, three bedroom, three bath home. Thoughtful details are luxuriously appointed to appeal to the traveler looking for privacy, style and elegant design.Walk up the brick drive and enter the gate to the palm tree-lined ...
Property Type
Key West House
4 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall.Inside, the comfortable ...
Property Type
Key West House
5 BR | 4 BA | Sleeps 10 | Quick View
Key Amenities
About this property
Luxury on Duval Street in historic Key West? Luxury is not a word most people associate with Duval Street... until you look at Dreaming On Duval! There are very few private homes on this famous street, let alone a single-family, free-standing vacation rental that is just steps away from everything Key ...
Property Type
Key West House
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Located in The Colony, a secluded compound just steps from Duval Street, Colony Calypso is a peaceful retreat. Enter the home through the tranquil and inviting living space, accented with sage green walls, new tile floors and pops of color from local artwork and photography. A vaulted ceiling with exposed ...
Property Type
Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
About this property
2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, the main 2/2 house features an indoor/outdoor ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Havana Lane recalls a time in Key West's colorful history when cigar makers populated the neighborhood, gathering on their porch stoops to cool off and socialize with friends. Very close to the colorful Key West Cemetery, this classic Conch cottage embodies the essence of rustic charm while offering modern ...
Property Type
Key West House
We absolutely LOVED it! One Havana Lane will be forever in our best memories of our time spent in the Keys! The pool was perfect and we enjoyed the few entertaining iguanas. The house was laid out so that ...
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored ...
Property Type
Key West House
4 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
An absolutely perfect location, just a half a block off Duval Street and within walking distance to amazing restaurants, turquoise beaches and the Southernmost Point in the United States. Louisa House has it all for the perfect Key West vacation.A historic home with elegant curb appeal, Louisa House ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Southard Street Downstairs Queen Conch is a two bedroom two bathroom retreat in a house consisting of three vacation suites. Open floor plan with French doors that open to the large shared sunny pool surrounded by beautiful landscaped garden.
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Unique oceanfront living only 65 feet from the Atlantic!The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit.The huge oceanfront balcony can be accessed from both the living/dining ...
Property Type
Key West Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Located in The Colony, a secluded compound just steps from Duval Street, Colony Sunset is a colorful and relaxing retreat. Walk up the flagstone path and enter the home through the vivid and cheerful living space, accented with cerulean blue walls and splashes of tropical art. A vaulted ceiling with ...
Property Type
Key West Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter the home through the serene and inviting living space, accented with blue and white decor, wood floors and pops of color from nautical-themed accents and artwork. A vaulted ceiling with ...
Property Type
Key West House
Studio | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location.The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics ...
Property Type
Key West Studio
4 BR | 4 BA | Sleeps 10 | Quick View
Key Amenities
About this property
Cock-a-doodle-do Vacation Rental, named for Key West's beloved chicken population, is a mid-town oasis! 5 minute drive to Old Town or take Uber for just $ 10!A meticulously updated pool home with beautifully lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, ...
Property Type
Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
About this property
This mid-town Key West home is beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in the attached pavilion with ornate iron and ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Located in the heart of Old Town, Duval Square is a charming brick-paved and tree-lined courtyard complex located at the quieter end of Duval Street. The residential units are located upstairs, while quaint shops and restaurants occupy the courtyard below.This recently upgraded unit is tastefully ...
Property Type
Key West Condo
Studio | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perched on the very edge of the turquoise waters of the Atlantic. Located on the quiet end of a waterfront townhome community, this property features simply the best views you will find in ...
Property Type
Key West Condo
Studio | 1 BA | Sleeps 2 | Quick View
Distance to beach: 0.5 miles to South Beach
Key Amenities
About this property
This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $45 * WiFi included * King size bed * Check-out cleaning included * Outdoor table and two chairs * spacious shower * excellent loctaion for walking Old Town * Duval Loop bus passes this adress for free ...
Property Type
Key West Condo
This little gem had everything we needed and was just perfect for a getaway for two. We appreciated the tips left by the owner, giving recommendations for dining and activities, and it was fun to have ...
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Located just steps from famous Duval street, this two-story town home is located in quaint, cobble stoned Duval Square. You are within the heart of the historic district and can walk almost everywhere. Although close to Duval, the home is a quiet escape from the hustle bustle.This town house community ...
Property Type
Key West Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
The Horse Conch is a one bedroom one bathroom suite in a house consisting of three vacation suites. Decorated with tropical color palette and has a queen bed. Accessed from the second floor covered porch that overlooks the shared gardens and pool below.
Property Type
Key West House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Everything your would need to assure your Key West Vacation is a success is here at my Sunset Marina Ocean Front Condo. The best value-added feature of this property is it's unique location. Sunset Marina Residences are situated on a very narrow strip of land stretching out into the Gulf of Mexico. My ...
Property Type
Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Recently renovated in February 2018, Villa Serena is the perfect space for your relaxing vacation.The downstairs living area is decorated in soothing cobalt and beachy sand tones and provides plenty of space for ...
Property Type
Key West Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Distance to beach: 0.3 miles to Ft. Zachary Taylor Beach
Key Amenities
About this property
2 Story 2 Bedroom 2 1/2 Bath Townhome in Truman Annex Location, Beauty and Comfort! Kokomo Key has what you are looking for! This upscale home has been meticulously designed with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully landscaped ...
Property Type
Key West Townhome
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. The two one bedroom suites are located on the second floor, ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly ...
Property Type
Key West Condo
6 BR | 6.5 BA | Sleeps 16 | Quick View
Distance to beach: 0.3 miles to Ft Zachary Taylor
Key Amenities
About this property
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...
Property Type
Key West Villa
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perched on the very edge of the turquoise waters of the Atlantic. Located on the quiet end of a waterfront townhome community, this property features simply the best views you will find in ...
Property Type
Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
About this property
These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall.Inside, the comfortable ...
Property Type
Key West House
1 BR | 1 BA | Sleeps 3 | Quick View
Distance to beach: 0.3 miles to Ft. Zachary Taylor
Key Amenities
About this property
Beautifully Remodeled -1BR/1BA End Unit Shipyard Condo in Truman Annex Location, Beauty and Comfort! Southard Breezes has what you are looking for! This gorgeous home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and ...
Property Type
Key West Condo
1 BR | 2 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds: relaxing and taking advantage of all that Key West has to offer. Within 2 blocks ...
Property Type
Key West House
Studio | 1 BA | Sleeps 2 | Quick View
Distance to beach: 0.5 miles to South Beach
Key Amenities
About this property
This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $45 * King size bed * WiFi included * check-out cleaning included * 2 wall AC units * flat screen TV * Shared gas grill * porch with ...
Property Type
Key West Condo
2 BR | 1.5 BA | Sleeps 4 | Quick View
Key Amenities
About this property
In the heart of old town Key West, nestled within the secluded and lush community of private homes and condominiums of Truman Annex, this Shipyard Condominium has convenient access to both the gorgeous Fort Zachary State Park Beach and historic old town Key West.This colorful and whimsically decorated ...
Property Type
Key West Condo
2 BR | 3 BA | Sleeps 6 | Quick View
Distance to beach: 0.5 miles to Higgs Beach
Key Amenities
About this property
"MONTHLY" RENTAL ONLY: Old Town Tropical Oasis, Private Pool, Hot Tub, Private Driveway. Meticulously restored and maintained home featuring: 2 bedrooms + den with sleep sofa (can be a 3rd bedroom) and 3 full en suite bathrooms. Our favorite part of this property is the lush & extremely ...
Property Type
Key West House
4 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discriminating travelers for over 10 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenitites and ideal location the perfect spot to enjoy all that Key West has to offer.Why ...
Property Type
Key West House
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
n the heart of Old Town and convenient to just about everything, this condo is set above a quaint brick and tree-lined courtyard that includes shops and restaurants. This three bedroom, two bath unit is in one of the only "stand-alone" buildings in the Duval Square complex. Simply walk down ...
Property Type
Key West Condo
Loved the location,place was very nice and relaxing. We really enjoyed ourselves. Would stay here again in a heartbeat.
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
La Brisa Beach Condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly ...
Property Type
Key West Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 4 miles to Smathers
Key Amenities
About this property
MONTHLY RENTALS ONLY We purchased Bougainvillea Villa in late 2014 as our future retirement home. The villa was built in the early 1960’s and our neighbors tell us that at one time Jimmy Buffett’s manager owned and lived in the home. It has always been a private home, and was renovated and ...
Property Type
Key West House
Nothing is missing from this very clean and very well organized beautiful home situated on a wide lagoon. For us, the highlight is the superb view of the wide lagoon from the window wall across the entire ...
4 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths. Enjoy breathtaking views of the ocean ...
Property Type
Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Unique oceanfront living only 65 feet from the Atlantic!The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit.This is one of the most elegant and colorful 2 bedroom units in the Key ...
Property Type
Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water as few do in Key West. The breathtaking view can be seen as soon as you enter this spacious 2 bedroom condo. It has just been purchased and newly refurnished ...
Property Type
Key West Condo
Studio | 1 BA | Sleeps 3 | Quick View
Distance to beach: 22 yards to Public use + Private views Waldorf Astoria Resort
Key Amenities
About this property
Get yourself dates before flights! Art studio is smaller available monthly till mid October phone for inquiry,, Key West has wind! Upon request Happy to hold you first in queue- a short while! Ocean view studios 2? In town, of Key West? YES! Best Stay In Key West! 3 blocks from Duval St! But ...
Property Type
Key West Studio
We chose this listing because we wanted to have the true key west experience!! The house definitely makes you feel like a true local. Each morning enjoying coffee on the patio and the ocean waves lull us ...
Stay steps from the sand in your Key West vacation rental
Relaxing, laid-back Key West calls to beach bums who prefer their landscape pristine and untouched. Key West is famous for watersports, nightlife, beaches and historic sites. Don’t miss Duval Street, one of the most energetic strips of shops, bars and cafes in Florida. Whether you prefer culture or the outdoors, Key West has plenty to offer in a relaxed, welcoming atmosphere.
From a romantic bungalow for a couple to a house that can fit your entire family and more, the Key West house rentals are endless. When staying in one of our Key West vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our condos and villas even come with special amenities like a set of bicycles, chef’s kitchen, and in-home theater. Use the filters to narrow down your choices and choose the property that calls to you, just like Key West does.
Key West, Florida travel advice
Thanks to economic boom and a bustling cigar industry, this area's became quite a hot spot by the turn of the 20th century. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches. History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street. Located closer to Cuba than to Miami, Key West offers endless Latin and Cuban cultural influences from the cuisine to the music and art. Running four miles long and about two miles wide at its widest, this is a small island. The popular Old Town makes up about half of this area.
Climate
Abundant sunshine and gentle breezes make Key West one of the most popular tourist destinations in Florida. With over 320 sunny days per year you’ll most likely get the weather you want, no matter when you visit. Be sure to bring plenty of sunscreen and beach umbrellas as the UV rays can be quite strong here. The sea temperature is almost bath water and you’ll love the turquoise-blue color.
Top activities and attractions
Even getting to Key West is an adventure. The Overseas Highway is one of the most beautiful drives in the country. Completed in 1938, it connects a string of cays and coral rock with 113 miles of concrete roadway. The aptly named Seven Mile Bridge is the longest and most scenic of the entire route.
Key West’s diverse and unique ecosystems are a result of the convergence of two major bodies of water. There’s endless entertainment to be had on the ocean. You’ve got the deep blue Atlantic and its Gulf Stream current to the south and the shallow flats of the Gulf of Mexico to the west. From deep sea fishing to parasailing and even just body surfing, you’ll love a day out on the water in Key West.
Hop on the Conch Tour Train for a fun way to see the surrounding area. You’ll get a narration of the city’s past from an experienced tour guide as you cruise around the streets. Walking tours are one of the best ways to see the city, too. Peek in at the area’s intriguing architecture, courtyards, and gardens.
On the presidential side of life, don't miss a tour of the Harry S. Truman Little White House, a command center during World War I and II as well as the winter home of President Harry S. Truman. Fort Zachary Taylor Historic State Park is a great place to swim, snorkel, and catch the sunset.
Dining and Nightlife
Over 300 restaurants and bars make this city one of the most fun places to be in southern Florida. For those with a sophisticated palate, try the highly-rated Bien restaurant to indulge in Latin & Cuban flavors. For great sandwiches and service, eat at the cleverly named Munch Box to break up your day of adventure. For Korean food that will make you scream “WOW”, pop in to Garbo’s Lunchbox. And lastly, for those who love to brunch, visit Key Plaza Creperie for delicious breakfast foods.
At night, Duval Street is the place to be. The Green Parrot is Key West’s oldest bar but it’s still a rockin’ atmosphere. Famed local Ernest Hemingway loved to get sauced at Sloppy Joe’s bar. (Don’t miss the Ernest Hemingway Home & Museum to get a closer look at what made this famous author tick.) For those who like the legitimate arts, take in a performance at Key West’s Fringe Theater, the Red Barn Theatre, or the Waterfront Playhouse.
For the kids, take the family to Mallory Square, where you’ll find local performers, plenty of fried food, and gorgeous sunset views.
Key West vacation homes on FloridaRentals.com
Vacation rentals in Key West on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!
