Key West Vacation Rentals by Owner
Book Your Key West Vacation Rental Home Here and Save!
Many properties to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities that will make your Florida visit enjoyable.
Vacation Rentals by Owner in Key West Florida.
We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for places to rent in Key West, Florida.
The Galleon Resort in Beautiful Key West. Amazing Views! Over 500 Reviews!
Key West Hotel resort 
5.0 Star Review
RESERVATIONS AVAILABLE IN SEVEN NIGHT INCREMENTS ONLY WITH CHECK-INS on SATURDAYS
Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resor.......read more
Key West
2 Bedroom(s) - 2 Bath(s)
Hotel resort Rental Sleeps 6
Your Condo by the Beach with Ocean View
Key West Condo 4.9 Star Review
The Jungle Breeze condo at LaBrisa Condominiums.
*Ocean View
*Free WiFi
* Free Covered Parking
* Final cleaning included in price
* KING size bed.
* Accommodates 2 adults
* Recently renovated this condo features all new flooring and a brand new kitchen
* Full size washer and dryer.
This is not a hotel; it is a privat.......read more
Key West
1 Bedroom(s) - 1 Bath(s)
Condo Rental Sleeps 2
NEW LISTING! Waterfront townhouse w/ pool, fenced backyard & deck - dogs ok
Key West Private vacation home
*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 stunning property overlooking the Gulf of Mexico boasts panoramic views from nearly every room and the private pool. Designed with hand scraped bamboo floors and a beautiful wraparound deck w.......read more
Key West
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6
"BEACH HOUSE"~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
Key West Private vacation home 5.0 Star Review
PRESTIGIOUS TROPICAL RETREAT...
Indulge in this spectacular two-story home situated in the premier gated community of historic Truman Annex. Escape to a sun-kissed dream as soon you enter this picturesque community, surrounded by swaying palm trees inviting you to enter your island vacation home which is tucked away on a quiet lane. Totaling 4 b.......read more
Key West
4 Bedroom(s) - 4 Bath(s)
Private vacation home Rental Sleeps 8
Simonton Studio, an Old Town get-away for 2
Key West Apartment 4.9 Star Review
The Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West. So, get out there and live it up in Key West and come home to a king size bed and everthing you need to fix your own cocktails and prepare some shrimp on the shared propane grill in the Courtyard.
Located in a .......read more
Key West
Studio
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
key west Condo 4.9 Star Review
Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all three bedrooms, the kitchen and the living room. Birds of various types, boating activities, lush oasis gardens are just a few reasons why people keep returning to our paradise property. "Click" on \'more information\' also "click".......read more
key west
3 Bedroom(s) - 3 Bath(s)
Condo Rental Sleeps 8
William Skelton Home - Heart of Key West - Save 10% on Your 5+ Night Stay!
Key West Private vacation home 4.9 Star Review
The William Skelton "Pink House" is located just steps from Duval Street in the heart of Old Town Key West. At this very spacious and historic home, you\'ll enjoy 6 comfortable bedrooms, a private backyard pool, two spacious living rooms, shaded outdoor patios and porches, and so much more.
A perfect choice for family reunions, weddings, an.......read more
Key West
6 Bedroom(s) - 4 Bath(s)
Private vacation home Rental Sleeps 14
BOTTOMS UP BUNGALOW - 2 Bedroom / 2 Bathroom With PRIVATE POOL
Key West Private vacation home 5.0 Star Review
Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West.
This pristine Florida Bungalow is 2 bedrooms, 2 bathroom single family home and offers all the amenities you need to make this your perfect vacation. Including off-street parking, swimming pool, quaint gazebo equipped with wet bar and custom seating. Th.......read more
Key West
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6
Villa Fleur at Shipyard Condominiums
Key West Condo 4.8 Star Review
Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and dining area. The living room features comfy furniture and a panel TV. One queen bedroom and one twin bedroom. Enjoy outdoor dining on the brick patio surrounded by a tropical landscape.
Villa Fleur is located in the Shipyard Co.......read more
Key West
2 Bedroom(s) - 1 Bath(s)
Condo Rental Sleeps 4
BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard.
Key West Private vacation home 4.8 Star Review
You will love our newly renovated 2 bed/ 2 1/2 bath private townhome in a secure community. Perfect location. This property doubles as our second home when we are in town. Renovations include new wood flooring, fresh paint, new kitchen with stainless appliances and granite tops. All furnishings and accessories are new. Private courtyard with sunde.......read more
Key West
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Key West Condo 4.9 Star Review
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you\'ll get without sacrificing a good night\'s sleep. This two bedroom Villa Vista is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.
The number one reaso.......read more
Key West
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4
Rare Penthouse 2 bed/2bath additional King in loft
Key West Condo 4.6 Star Review
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath jacuzzi, have front row seats to the variegated lights of Mother Nature\'s Sunrises, have the convenience of a fully equipped kitchen, two sitting areas for extra comfort and flexibility and for countless hours to enjoy the view.......read more
Key West
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 8
Peaceful Setting Amongst The Active Island Life Style
Key West Condo 4.9 Star Review
Enjoy the New and Completely Renovated bathrooms to this tropical residence. This is quiet, peaceful living on the Atlantic Ocean. The spectacular view can be seen immediately upon entering the condo. The floor to ceiling glass walls provide a full sea panorama from the living room, dining room, kitchen and master bedroom. The 31 foot oceanfront ba.......read more
Key West
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Key West Condo 5.0 Star Review
This wonderful 2 bedroom downstairs unit is owner\'s second home and has just been beautifully and professionally decorated. Fresh paint throughout, all new hardwood flooring, new kitchen with granite counter tops, stainless steel appliances, and brand new designer furnishings make this a home away from home. A large rear courtyard with a wood sun .......read more
Key West
2 Bedroom(s) - 1 Bath(s)
Condo Rental Sleeps 5
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
Key West Private vacation home 5.0 Star Review
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a private wonderland on the quieter end of Duval Street. Enjoy morning coffee or people watching on the elevated, partially covered front porch. The home’s backyard oasis includes a covered rear patio, a pool with waterfall feature an.......read more
Key West
5 Bedroom(s) - 5 Bath(s)
Private vacation home Rental Sleeps 10
Key West Suites Hotel - Adam Scott Rote Suite
Key West Apartment 4.8 Star Review
Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both Duval and Southard Streets.
The building once housed the Chrysler/Deso.......read more
Key West
1 Bedroom(s) - 1 Bath(s)
Apartment Rental
Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)
Key West Condo 4.7 Star Review
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. If the dates you need are not available check my other Key West vacation rental (Henry\'.......read more
Key West
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 5
Craig & Cindy Truman Annex Foundry Townhouses (2 bedrooms 2 1/2 baths)
Key West Private vacation home 5.0 Star Review
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West....Truman Annex. We offer 2 Foundry Townhouses practically adjacent to each other. Truman Annex is a six block gated community right at the entrance to Ft. Zachary Beach, 2 blocks from Duval Street, and right next to the nightl.......read more
Key West
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Key West Condo 5.0 Star Review
Partial list of rental amenities at Craig & Cindy\'s Truman Annex Shipyard Condos include:
2 bedrooms 1 bath {queen and 2 twins (or we can convert the 2 twins to a king bed with a king converter) plus a sleeper sofa in the living room.
Fully equipped kitchen with upgraded appliances and cooking accessories.
Washer & dryer with iron.......read more
Key West
2 Bedroom(s) - 1 Bath(s)
Condo Rental Sleeps 4
Old Town Key West Condo - MONTHLY RENTALS ONLY
Key West Condo 5.0 Star Review
Our condo is located is in the heart of Key West\'s Old Town. This neighborhood is filled with historic homes dating from the period when Key West was the wealthiest city in the United States. The condo is in a historic home with three other condo units. The location is ideal to explore Key West by foot or bike. Great restaurants are within a f.......read more
Key West
2 Bedroom(s) - 3 Bath(s)
Condo Rental Sleeps 4
Things to Do while on Vacation In Key West Florida
Key West is just about the perfect vacation destination in Florida. As cliché as it sounds, there truly is something for everyone. Whether you are looking to party like a rock star or seeking a relaxing vacation in nature, Key West has what you are looking for. Whether you are interested in bar hopping, beach hopping, dolphin watching, bird and wildlife watching, or some of the best people watching around; Key West is a must-visit spot in Florida.
Duval Street
You truly can’t visit Key West without experiencing Duval Street. This 1.2-mile street is the main thoroughfare and has so much to offer. Click here to see the live feeds of Duval Street from the world-famous Sloppy Joes, coined a Key West tradition. There are more than 100 bars and dozens of shops and boutiques along this stretch. If you love live music be sure to visit the Green Parrot Bar and The Hogs Breath Saloon, both locations are well-known for hosting phenomenal national act.
The Ernest Hemmingway Home and Museum
If you enjoy literature and history, you will want to plan a visit to Hemingway Home & Museum. The estate was built in 1851 and is the most popular tourist attraction in Key West. Ernest Hemingway lived there from 1931 to 1939 and wrote some of his most popular literary works on the estate.
Mallory Square – Sunset Celebration
One of Key West’s most popular activities is the Sunset Celebration at Mallory Square Dock. People visit from all over the world to catch these exquisite sunsets and experience this nightly arts festival. There are street performers, food vendors, art installations, and extraordinary shopping options.
Key West Butterfly and Nature Conservatory
If you are a nature-lover, you will want to plan a visit to The Key West Butterfly & Nature Conservatory. Click here to check out the live webcams set up at the conservatory. You can walk among hundreds of butterflies and beautiful, colorful birds inside their habitat.
Dry Tortugas National Park
You can also take a ferry ride on the Yankee Freedom to visit Fort Jefferson Dry Tortugas National park. Take a guided tour and learn about life at the fort in the 1860s. The park is 100-square-miles and, aside from the fort, is known for is gorgeous blue waters, coral reefs, and wildlife watching.
Discover the Best Deals for Key West Vacation Rentals in the Florida Keys.
We have 2,3 or 4 Bedroom beachfront Vacation Rental Homes with ocean view or a Beach House for the entire family. Book Direct Here!
Key West, Florida is known for water sports, lively nightlife, beaches, historic sites and its pastel, conch-style architecture. Located at the southernmost point in the Florida Keys and the United States, visitors can enjoy the Ernest Hemingway Home and Museum, tour the Harry S. Truman Little White House, explore beautiful tropical gardens or visit Mallory Square, a waterfront plaza just west of Duval Street where its “Sunset Celebration” is one of the most popular things to see and do in Key West.