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.
The Galleon Resort in Beautiful Key West. Amazing Views! Over 500 Reviews!
Key West Hotel resort 
5.0
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
2 Bedroom(s)
2 Bath(s) Sleeps 6
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
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
3 Bedroom(s)
3 Bath(s) Sleeps 6
"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
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
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".......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
William Skelton Home - Heart of Key West - Save 10% on Your 5+ Night Stay!
Key West Private vacation home 4.9
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
6 Bedroom(s)
4 Bath(s) Sleeps 14
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
Villa Fleur at Shipyard Condominiums
Key West Condo 4.8
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
BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard.
Key West Private vacation home 4.8
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
2 Bedroom(s)
3 Bath(s) Sleeps 6
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 reaso.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Rare Penthouse 2 bed/2bath additional King in loft
Key West Condo 4.6
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
2 Bedroom(s)
2 Bath(s) Sleeps 8
Peaceful Setting Amongst The Active Island Life Style
Key West Condo 4.9
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
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 .......read more
2 Bedroom(s)
1 Bath(s) Sleeps 5
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
Key West Private vacation home 5.0
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
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)
Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)
Key West Condo 4.7
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
2 Bedroom(s)
2 Bath(s) Sleeps 5
Craig & Cindy Truman Annex Foundry Townhouses (2 bedrooms 2 1/2 baths)
Key West Private vacation home 5.0
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
2 Bedroom(s)
3 Bath(s) Sleeps 6
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Key West Condo 5.0
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
2 Bedroom(s)
1 Bath(s) Sleeps 4
Old Town Key West Condo - MONTHLY RENTALS ONLY
Key West Condo 5.0
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
2 Bedroom(s)
3 Bath(s) Sleeps 4
SEAPORT SKYLINE at Galleon Resort near Mallory Square—Beach, King Suite
Key West Condo
OCEANFRONT CASUAL LUXURY CONDO RENTAL 40 FT FROM THE WATER WITH BREATHTAKING & UNOBSTRUCTED VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO. (These views are also available from the master bedroom, living area and kitchen all day, every day)
2nd FLOOR OCEANFRONT CONDO RENTAL
Oceanfront privacy and luxury at The Galleon Resort in Old To.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
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
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
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 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
Waterfront Retreat, New Year’s Eve, 7 Nights, Sleeps 6, Beach, Boat Docks, Hyatt
Key West Condo
Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary amongst the lush landscape of Key West. Envision old-fashioned screen-enclosed porches, gardens bursting with tropical flowers and crystal-clear water views. Enjoy the privilege of a private white sand beach, furnished with thick-cushioned chairs, picnic tables, ba.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR/2BA Condo & Pool + LAST KEY SERVICE
Key West Condo 5.0
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
OLD TOWN OASIS is back! After three years out of the rental program, this luxurious condo has returned, with all the same elegance enjoyed by many guests since 2004, and with many improvements.
You’ll be staying right near the o.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Old Town Getaway
Key West Private vacation home 5.0
Newly redecorated by a one of Key West top interior designers!!
Elegant and adorable cottage on one of the nicest lanes in Old Town Key West. Vaulted ceilings, designer kitchen with granite countertops, stainless steel appliances and bar area with open and airy floor plan. Lots of light with large windows and skylights. Private yard with deck an.......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
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
Welcome to the Shady Palms - Private Pool - RealKeyWest
Key West Private vacation home
Step into this beautifully restored and redoracated 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 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.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 6
Villa Nomade at Shipyard Condominiums
Key West Condo 4.8
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
Heart of Key West - 2BR Waterfront at the Galleon Resort
Key West Condo 5.0
Welcome to the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, restaurant and bar and much more on site.
Relax in the hot tub or sauna during your stay or work out in the on-site fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
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 .......read more
1 Bedroom(s)
1 Bath(s) Sleeps 4
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
Key West Apartment 5.0
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
Superb Location, Affordably Priced
Key West Apartment 4.9
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
BRAND NEW HOT TUB JUNE 2022 aboard Houseboat Haven
Key West House boat 2.0
Summary:
Experience Key West in a new way: aboard a luxury houseboat! The brand new hot tub aboard Houseboat Haven was replaced this June 2022!
From watching sunrise on the dock to watching sunset from the balcony, or enjoying one of the best happy hours in town, you won\'t even need to leave the Marina. Come aboard & see why life really is b.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
New Listing - Beautiful 3/2 Golf Course Home
Key West Private vacation home
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
New Listing-Key West Charmer!
Key West Private vacation home
This home was built in 1933 and was an original Key West shotgun house and has been beautifully restored. The house has been decorated uniquely and has a tranquil and beachy vibe.
Upon entry you have a front closed in office space or reading room. This room looks out to the lush landscape and is perfect for an early morning coffee or an afternoo.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 4
Caroline On My Mind-New Listing-Light, Bright and Airy!
Key West Condo
When they say it\'s all about the location, this home says it all!
Welcome to this beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street.
A stairway decorated with wainscoting will lead you to the entry of "Caroline on My Mind," where you will notice this hidden gem has an open, comfortable living area, al.......read more
2 Bedroom(s)
2 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
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
A Touch of Bermuda at Truman Annex
Key West Cottage 4.9
KEY WEST REMAINS AN OASIS IN FLORIDA SO 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 seven available for rent).......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Artist’s Retreat - Old Town Key West
Key West Private vacation home
Exquisitely designed and perfectly located in Old Town Key West Southernmost Point area, Artist’s Retreat is a breathtaking Key West hideaway.
This double lot home expands approximately 1800 square feet and was custom built to perfection!
Offering 3 bedrooms, 2 bathrooms, vaulted ceilings and custom hardwood floors throughout. Th.......read more
3 Bedroom(s)
3 Bath(s)
Your own Private Resort! 40ft Dock on Canal w/ Pool and RV Hookup!
Key West Private vacation home
The grounds of this home will take your breath away. This is a unique opportunity to experience the Keys with your own private beach, resort tiki hut, pool, 40ft dockage right on the gorgeous Florida Bay with a front row seat for sunset every night. Just 15 min from Duval!
Where you will be staying:
Our beautiful resort style home sit.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Cozy studio cottage in Old Town Key West
Key West Cottage
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
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 a.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
Key West Condo 4.8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
When your vacation is set around your experiences on the water, where you choose to spend your time on land should be convenient and comfortable. Whether it be a day at the sandbar… reeling in a big catch… kayaking through the mangr.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
Key West Condo 4.9
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
SET SAIL celebrates the experiences of the Keys, both on the water and on land. The ideal complementary home base for your water-based excursions awaits in this condo just steps from the marina. SET SAIL is a well-appointed first floor .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6