Key West Vacation Rentals in the Florida Keys
Book Places to Stay and Vacation Home Rentals in Key West, Florida Keys Directly Online Here and Save!
We have many choices for Key West, Florida Keys Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer for your visit to Florida.
Your Condo by the Beach with Ocean View
Key West Condo 
4.9
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
1 Bedroom(s)
1 Bath(s) Sleeps 2
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
Key West Private vacation home 5.0
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
4 Bedroom(s)
4 Bath(s) Sleeps 8
BOTTOMS UP BUNGALOW - 2 Bedroom / 2 Bathroom With PRIVATE POOL
Key West Private vacation home 5.0
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
2 Bedroom(s)
2 Bath(s) Sleeps 6
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
key west Condo 4.9
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" o.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
Villa Fleur at Shipyard Condominiums
Key West Condo 4.9
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
2 Bedroom(s)
1 Bath(s) Sleeps 4
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Key West Condo 4.9
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 reason .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Simonton Studio, an Old Town get-away for 2
Key West Apartment 4.9
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
Studio
1 Bath(s) Sleeps 2
Key West Rooster
Key West Condo 4.9
Please call or text if you’d like to book our home
702 232... 3750
When booking our home please include a brief description of who you’ll be traveling with and what brings you to the area with your reservation request. We like to know who will be staying in our home ?
Welcome to your front row seat of the New Truman Waterfron.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
Key West Private vacation home 4.8
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
5 Bedroom(s)
5 Bath(s) Sleeps 10
Peaceful Setting Amongst The Active Island Life Style
Key West Condo 4.8
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
2 Bedroom(s)
2 Bath(s) Sleeps 4
Rare Penthouse 2 bed/2bath additional King in loft
Key West Condo 4.7
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 views.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 8
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Key West Condo 5.0
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 d.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 5
Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)
Key West Condo 4.8
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's.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 5
Key West Suites Hotel - Adam Scott Rote Suite
Key West Apartment 4.8
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
1 Bedroom(s)
1 Bath(s) Sleeps 6
Location, location, location in the heart of Old Town!
Key West Private vacation home
Tricksy's Place located in the heart of Old Town, Key West is a perfect retreat to relax, and the perfect starting point to explore all that our beautiful tropical island has to offer. Only one block from Duval St., a short walk to the Southernmost Point, Hemingway House, Key West Lighthouse, and more. Stay in and cook an elegant meal in our modern.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 6
Old Town Key West Condo - MONTHLY RENTALS ONLY
Key West Condo 4.9
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 fi.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 4
Lush retreat minutes away from both Mallory Square & Duval Street.
Key West Condo
f bedrooms, full kitchen, screened in patio with a relaxing pool, and dock area perfect for sunset over the Gulf of Mexico. Free covered parking. A great place to rest from your frolicking fun times!.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
The Maria Luz, a Key West Monthly Rental
Key West Apartment
The Maria Luz a is located in a Historic Conch house from the early 1900’s updated and decorated by its owner.
Features original hardwood floors, updated bathroom. The galley-style kitchen is fully stocked with all the necessary essentials. Other features include also features WIFI, cold A/C, private washer and dryer in the unit.
You c.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 2
The Cordelia, a Key West Monthly Rental
Key West Private vacation home
The Cordelia is located in a Historic Conch house from the early 1900’s updated and decorated by its owner. Features original hardwood floors, new bathroom and chic decor items. The galley-style kitchen is equipped with white quartz countertops, a black retro tile backsplash, and stainless-steel appliances; fully stocked with all the necessary e.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 2
The Gisela, a Key West Monthly Rental
Key West Private vacation home
The Gisela is located in the rear of an adorable Conch Cottage. Finished with a soft and neutral color scheme that will take your breath away. Enter through your private entrance into the living room with features high ceilings and a spectacular light filled living space. 45-inch flat-screen TV with cable and streaming services. Between the kitch.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 1
The Rex, a Key West Monthly Rental
Key West Private vacation home 5.0
Enjoy a stylish experience at this centrally-located apartment. Just a short walk from some of Key West best restaurants and shopping. This 1 bedroom, 1 bath has been beautifully furnished, features stainless steel appliances, private washer and dryer in unit, private porch with a view of a lush courtyard........read more
1 Bedroom(s)
1 Bath(s) Sleeps 2
Hyatt Residence Club Sunset Harbor-Old Town- Heart of Key West, Sleeps 4!
Key West Apart-hotel
Tropical Key West welcomes you to a classic Florida condominium, offering a one bedroom unit with plush queen bed, fully equipped kitchen, dining area, living room with sleeper sofa, TV, stereo and DVD player, and private balcony with pool or harbor views. Walk to Duval St. and Mallory Square! You will be in the middle of it all while you enjoy the.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 4
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Key West Private vacation home 4.6
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 sundec.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 8
Stunning tropical home in Old Town Key West with private pool and hot tub
Key West Private vacation home
Spacious home with open floor plan. Completely renovated in 2018. Large heated pool and hot tub in a quiet tropical oasis. Located 2 blocks from the famous Duval with restaurants, shopping & live music........read more
7 Bedroom(s)
7 Bath(s) Sleeps 8
Welcome to the Shady Palms - Private Pool - RealKeyWest
Key West Private vacation home 5.0
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throughout the house to open up and let in the Key West sun. Relax in the living with a large screen TV or sit on the front porch to read a book and relax with the breezes or if needed, the porch fan. The kitchen is perfect to cook your.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 6
Superb Location, Affordably Priced
Key West Apartment 4.8
This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. This pet friendly accommodation is the perfect location for exploring Key West. You can walk to the Hemmingway House, the Butterfly Conservatory and stroll Duval St with it's many restaurants, shops, galleries and museums. .......read more
1 Bedroom(s)
1 Bath(s) Sleeps 2
Villa Nomade at Shipyard Condominiums
Key West Condo 4.9
Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. The living room is furnished with comfy furniture and a 50"TV. The bedrooms have queen beds. Enjoy outdoor dining on the deck surrounded by a tropical landscape.
Villa Nomade is located in the Shipyard Condominiums at the Truman.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
Key West Apartment 4.3
WELCOME TO LITTLE CASITA!
If looking for the perfect couple’s retreat, look no further!
This one bedroom, one bath historic apartment is located just blocks from Key West’s famous Duval Street & Historic Seaport where you’ll find restaurants, shops, and bars. The residential neighborhood will make you feel like a local!
.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 2
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
Key West Condo 4.8
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. The one bedroom Villa Porta is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. Please email us even if the av.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 4
Hidden Treasure- 2 bedroom 2 bath with shared pool
Key West Cabin 4.7
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high-end amenity that you could possibly desire. Two master bedrooms, two full .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
A Touch of Bermuda at Truman Annex
Key West Cottage 4.8
50% OFF I JUST HAD A CANCELLATION FOR THE WEEK OF DECEMBER 2-9. Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private townhome (one of only .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Escape to The Gumbo Limbo Cottage, a charming 2BR, 2.5BA vacation rental
Key West Private vacation home 5.0
Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.
As soon as you step inside, you'll b.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 4
Mulligan's Place - New Listing - Beautiful 3/2 Golf Course Home
Key West Private vacation home 5.0
Welcome to this Key West Tropical charmer located only 15 minutes away from Downtown Duval Street. This townhome is located in a gated community called the Key West Golf Club.
This pleasant, bright and spacious townhome comes with a large backyard space for entertaining or just lounging around and is located on a quiet cul de sac. This townhome .......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Caroline On My Mind-New Listing-Light, Bright and Airy!
Key West Condo
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting experience. The location is highlighted as a key factor, emphasizing the significance of its surroundings.
As you enter "Caroline on My Mind," you'll notice a stairway adorned with wainscoting, leading you to the entry. The ho.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Your own Private Resort! 50ft Dock on Canal w/ Pool and RV Hookup!
Key West Private vacation home 5.0
Discover your private paradise in the Keys! This exquisite waterfront home offers a unique opportunity to experience the beauty of the area with your own private beach, resort-style tiki hut, pool, and a 50ft dock. Just 15 minutes away from Duval Street, this is your ultimate getaway.
Highlights of your stay:
*A 1/3-acre property wit.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
Key West Condo 4.9
This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880's that was converted into individual condominiums many years ago, located just one block from Duval Street in the Heart of Old Town Key West. Our casual atmosphere allows you to chill out and enjoy having the best of Key West within easy walking distance of al.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
Cozy studio cottage in Old Town Key West
Key West Cottage 5.0
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to restaurants, docks, and Duvall St. Easy to get to everything yet quiet and secluded........read more
1 Bedroom(s)
1 Bath(s) Sleeps 4
La Casa de Luna- 1 bedroom 1 bath steps off Duval street
Key West Apartment 4.7
Located in the heart of historic Old Town Key West, just steps away from world-renowned Duval Street, La Casa de Luna is a ground level one bedroom, one bathroom condo that is part of a large house with a relaxing veranda. Easy walking distance to all your favorite restaurants and bistros.
Open the door to the full kitchen with refrigerato.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 4
2 BEDROOM SUITE, KEY WEST, HYATT BEACH HOUSE RESORT, SLEEPS 6!
Key West Hotel resort
Welcome to your own private sanctuary among the lush landscape of Key West - envision old-fashioned screen-enclosed porches, gardens bursting with tropical flowers and crystal clear water views. Hyatt Beach House Resort’s breathtaking gulf coast setting is matched only by the top-tier amenities and meticulous attention to detail that Hyatt is ren.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Feel the Island Winds From Casita In The Clouds: 2 Bed/2 Bath - Monthly
Key West Apartment 5.0
WELCOME TO CASITA IN THE CLOUD!
Your search for the perfect island getaway has ended!
This large 3 story, two bedrooms, two bath apartment boasts all the amenities you’d expect from your island home. Upon entry, you’ll be greeted by a loving foyer with a set of stairs leading you to the surprisingly spacious living room, ki.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w/ Pool, Spa & Exercise Room!
Key West Private vacation home 5.0
OLD TOWN CLASSIC...
This beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding location of Southard and Ashe Streets, this upscale abode is just minutes from Duval's many restaurants and bars. You are within walking and biking distance to museums, shopping, and Fort Zachary Taylor beach. Come inside this bri.......read more
3 Bedroom(s)
4 Bath(s) Sleeps 6
SEA FOREVER ~ Downtown Ocean View Home w/ 3 BR, 3.5 Ba w/ Pool!
Key West Private vacation home 5.0
MODERN TROPICAL JEWEL WITH STUNNING OCEAN VIEWS…
This contemporary and spacious custom-built gated home will beguile your senses, luring you inside with the finest of amenities and stunning design. Just a stone's throw away from the infamous Whitehead Southernmost Buoy, you are truly seated in the heart of paradise in this small gated communit.......read more
3 Bedroom(s)
4 Bath(s) Sleeps 6
VILLAGE ROOSTER ~ Quaint Cottage in Bahama Village Steps from the FUN!
Key West Private vacation home 3.8
BAHAMA VILLAGE TREASURE...
This charming Old Town home is just 3 blocks from the world-famous Duval Street, award-winning restaurants and delightful boutiques of Petronia Street in colorful and historic Bahama Village. Let your island soul unwind in this small but mighty abode that exudes Key West charm!
***PRIMARY GUEST MUST BE AT LEAST 25 Y.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Key West Private vacation home 5.0
****This property requires a minimum stay of 28 nights in the same calendar month****
***Brand New Pool with waterfall, saltwater, heater, and a chiller to maximize comfort!
Tropical Properties Vacation Rentals invites you to our beautiful historic home located in Historic Old Town Key West. This home is located just two blocks f.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Castaway Duval street Townhome
Key West Private vacation home 4.5
"Welcome to Duval Square" a secluded and gated community located on
upper Duval St; these properties are some of the most prestigious
on the island, which offer lush tropical landscaping, swimming pool
and private jacuzzi. This location is perfect for either complete
seclusion or if you prefer to view the many sights from above. Y.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 6
SERENITY ~ Relax in Ultimate Luxury and Comfort in Old Town Key West!
Key West Private vacation home 4.3
LOCAL LIVING....
Spend time relaxing in Paradise in the perfect home. Serenity is a beautifully decorated, 4 bedroom home, with 3 baths in an amazing location. Enjoy sunny Key West weather by spending time relaxing outdoors or soaking in the private pool.
***GUESTS MUST BE 25 YEARS OF AGE OR OLDER
FURNISHINGS..
Newly designer de.......read more
4 Bedroom(s)
3 Bath(s) Sleeps 8
Key West dream townhouse * Sleeps 6 * Like new! Old Town * Perfect location
Key West Private vacation home 5.0
This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 2 1/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 6
Hyatt Windward Pointe 2 Bedroom
Key West Apartment
★Excellent Key West Location - Oceanside Property - 2-Bedroom - 2-Bathroom - Sleeps 6.
★Very Clean - Very Nice Property.
Guests can enjoy the beautiful ocean breeze right next to the property. Guests may also enjoy the relaxing pool and the fully-equipped health and fitness center.
LOCATION:
Enjoy the white sands of the .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6