Vacation Rentals By Owner In Key West, FL

Key West Suites Hotel brbrWelcome 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. brbrThe building once housed the Chrysler/Desoto car dealership, a furniture store, and later a clothing store when the Beatles came to make a purchase which caused the cashier to pass out on the floor. It has since been refurbished into a beautiful art gallery, two restaurants, a bar, and the newly renovated apartments upstairs. The stately solid concrete building is extremely quiet so that you can’t really hear much of Duval despite being right on Duval. brThis in an unbelievable place and is priced right for what you get and the location. Absolutely everything is new, it was gutted and redone top to bottom. The floors and kitchen and bathroom were completely ripped out and rebuilt. All the top end appliances are brand new. The floor is completely new, the ceiling fans, new, lights, new, the bathroom with huge slab tile and solid glass partition, all new and amazing. When you walk in you are overwhelmed with a Wow factor! The biggest comments I hear from tenants is great location, much larger than I could imagine, clean, and silent. You may need a white noise machine to sleep because of how quiet it is. Someone who wants to be in old town on Duval in a luxury space this is more than awesome. brbrThe (201-814, 202-677,203-677, 204-677, 205-867) sq.ft. studio apartment boasts 10-foot ceilings with fans, 2 King beds (Sealy Posturepedic) plus a Queen size pull out leather sofa bed, huge 55-inch Samsung 4k smart tv, HD cable, Keurig coffee maker, full kitchen with pots, pans, plates etc., fridge with ice maker, stove/range, full length mirror, large window looking onto Duval and Southard street, complimentary extreme speed xfinity Wi-Fi and a huge luxury shower for rinsing off your salt of the sea. brbrThe corner of Southard and Duval is right downstairs, and from there you can reach in near equal distance Fort Zachary state park beach, Mallory Square, Hemmingway’s house, and the Southernmost point. There’s also great eating next door, the noodle shop Kojin, Thai and the best sushi Miso Happy, Cuban coffee queen for breakfast and lunch, keys coffee across the street with excellent sandwiches, Mr. Z's cheesesteaks across the street, the best vegetables at the Café across the street, fine dining within a block, great live music venue bars also within a block, and a quarter mile from ft Zachery state park.brbrYou must be able to bring your own luggage up two flights of stairs as it’s on the second floor, and there is no elevator to the historic building. brThe clean fee of $175 is a pass-through charge, it’s what the cleaners charge me, so unfortunately, it’s not negotiable. brbrYou won’t need a car, but if you do have one Parking is public on the street at metered spaces. You must provide your own parking. The cheapest way to park is to first unload your car at Key West Suites Hotel after paying the meter, then park and pay at the City owned “Park and Ride” corner of Grinnell and Caroline Street, then simply walk everywhere. You can walk from the garage to the unit or keep the parking stub and ride their free shuttle or the free Duval Loop bus. Just Google Duval Loop Bus Key West and it should come up, and on their bus route map it also shows the City Parking lots around Key West. Most of the street parking and lots cap out at 10 hours and have to be refilled every 10 hours or so, but some lots let you refill every 24 hours. It's about $32 to $36 per day to park. There’s usually plenty of parking though close to very close to the unit. brbrThere are plenty of bike racks all around the building, neighboring streets and pretty much all over town. Some people rent bikes, some rent scooters, some rent electric cars, but you can also walk everywhere in old town from the unit. Scooters and electric cars are treated the same as cars parking wise. There aren’t electric outlets near the unit to the street so make sure any electric vehicles have enough charge for you stay. brKey West allows Uber and Lyft besides the town cabs for which there are several companies. brbrParking:brParking is public on the street at metered spaces. You must provide your own parking. The cheapest way to park is to first unload your car at Key West Suites Hotel after paying the meter, then park and pay at the City owned “Park and Ride” corner of Grinnell and Caroline Street, then simply walk everywhere. You can walk from the garage to the unit or keep the parking stub and ride their free shuttle.

Apartment

Features.Key West Suites Hotel has an outdoor pool and fitness center

Key West, Florida, United States

Bed

Bath

Sleeps

$964.9

4 Bedroom, 3 Bathroom, Sleeps 8brLuxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Mother Ocean. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on private driveways leading to the house.brThis home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with a sectional leather couch around a large HD flat screen Smart TV. There is a dining table with seating for up to 6 diners, with additional seating for 4 at the kitchen bar. brThe master bedroom has a King sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has two twin beds that can be converted to a king with ample notice, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is also on the 2nd floor with a full size bed, flat screen TV, and also with balcony access. On the main floor there is a fourth bedroom with twins bed. There is a full bath down the hall for convenience.brOut back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. brAMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8 adults.brbrDockage is not available at this home's development.brbrRATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).brbrDOG FRIENDLY. Please contact us to confirm specific pet policies.

Oceanfront 4-Bed 3-Bath home with pool

Key West, Florida, United States

Bed

Bath

8

Sleeps

$686.92

NEW LISTING! brbrDREAMY OLD TOWN RETREAT…brThis Upper Duval classic abode exudes historic charm in quintessential Key West flair, yet offers the sleek comforts of modern island vibes. Cradled in an exceptional location, enjoy an ideal walkable lifestyle to the excitement of Duval Street, the white sands of the Atlantic Ocean, eclectic galleries and fine dining. Unwind and exhale in this southernmost gem that will exceed your expectations!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brFind your island zen as you enter a sun-dappled open concept layout, brimming with tropical sunshine flooding through French Doors and oversized windows, soaring ceilings, rich hardwood floors and iconic Dade County Pine walls. A state-of-the-art kitchen is your inner chef's dream, stocked with all the tools for creating a sumptuous feast for friends and loved ones. This exquisite interior is fashioned to soothe your senses and ease you into blissful serenity. Enjoy Youtube TV live streaming for binge-watching all your favorite shows. You will find the washer/dryer on the back deck in a shed just beyond the fence off the driveway. brbrSLEEPING ARRANGEMENTS:brEach of the 3 bedrooms offers ensuite privacy and plush king beds for the ultimate restorative slumber. The spacious primary suite boasts a gleaming walk-in shower and double vanity. The adjacent guest room has a shower/tub combination, perfect for soaking after a day of adventures. The private poolside cottage features a full bath with a walk in shower and a full refrigerator for added comfort and convenience.brbrOUTDOOR LIVING…brThe interior of the home flows seamlessly to a grand outdoor tropical oasis, designed for relaxing or entertaining. Sink into the sparkling pool (comes heated during the cooler months) surrounded by a spacious deck that is embraced by lush greenery and foliage. Dine under the splendor of sultry stars and nautical breezes.brbrPARKING...brThis home offers an off street parking space.brbrPETS...brThis is a DOG friendly home, NO CATS. Please include the size and breed when inquiring.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrTRANQUILITY RESIDES HERE...brVirtual Tour Url: https://my.matterport.com/show/ m=2PhrccNBKwu

SANDY CHIC ~ NEW LISTING! Upscale 3 BR/3.5 Ba Home w/ Pool and Parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$757.06

DOCKSIDE CATAMARAN STAY IN KEY WEST • 2014 Lagoon 52 • THE PERRY HOTEL & MARINAbrbrWelcome aboard our 2014 Lagoon 52 catamaran, permanently docked at The Perry Hotel & Marina. This is a DOCKSIDE-ONLY stay that combines life on the water with access to a full-service marina and resort.brbrPLEASE NOTE UP FRONT:brbrThis is not a hotel roombrAir conditioning is NOT availablebrThis is a real boat with real marine limitationsbrbrGuests who enjoy boats, marinas, and unique accommodations tend to love it. Guests expecting a traditional, climate-controlled stay should choose alternative accommodations.brbrTHE SETTINGbrbrThe vessel remains stationary at the dock for the duration of your stay. You’ll enjoy waterfront views, ocean breezes, and direct access to marina amenities.brbrCABINS & LAYOUTbrbrSix cabins total (three per hull):brbrPort SidebrbrBow Cabin: Double bedbrMidship Cabin: Bunk beds (best for children or additional guests)brStern Cabin: Double bed with EXTERNAL-ONLY ACCESSbrbrStarboard SidebrbrBow Cabin: Double bedbrMidship Cabin: Double bedbrStern Cabin: Double bed with EXTERNAL-ONLY ACCESSbrbrStorage is limited, as expected on a vessel, but the layout is functional for a dockside stay.brbrGALLEY & ONBOARD FEATURESbrbrThe vessel is connected to shore power and water when systems are functioning.brbrKitchen Includes:brbrElectric oven and cooktopbrCookware, utensils, dishesbrRefrigeration and coolersbrbrDue to marine space constraints, some items are stored under seating or bunks.brbrImportant:brThere is a BBQ on board that is not available for guest use.brbrMARINA AMENITIES (IMPORTANT)brbrGuests have access to:brbrResort-style poolsbrRestaurants and barsbrFitness centerbrMarina restrooms and showersbrLaundry facilities (paid)brParkingbrbrThese amenities are an integral part of the stay and serve as reliable alternatives to onboard systems when needed.brbrLOCATION & TRANSPORTATIONbrComplimentary shuttle to Old Town Key WestbrUber and Lyft readily availablebrGolf cart rentals nearbybrHOUSEKEEPING & EXPECTATIONSbrPlease avoid tracking sand into cabinsbrThis is a marine environment; minor quirks and maintenance needs can occurbrThis is not a hotel with on-demand, immediate onsite servicebrTHE EXPERIENCEbrbrThis is a practical, character-rich boat stay. You are staying on the water, not in a resort suite. The marina amenities are intended to complement the onboard experience.brbrIMPORTANT INFORMATION — PLEASE READ CAREFULLYbrDOCKSIDE ONLYbrbrThe vessel does not leave the dock under any circumstances.brbrREQUIRED ORIENTATIONbrbrGuests must watch a short orientation video prior to arrival covering access, toilets, electrical systems, and vessel-specific features.brbrAIR CONDITIONINGbrbrAir conditioning is NOT available on this vessel.brbrThere is no AC provided. Guests should plan accordingly.brbrDuring summer months in Key West, temperatures and humidity can be extremely high, and the interior of the vessel can become very warm, including overnight.brbrGuests who require air conditioning for comfort should not book this property.brbrWATER & ELECTRICITYbrbrAs a marine vessel, onboard systems (including water and electricity) depend on marina connections and marine infrastructure.brbrTemporary interruptions can occurbrThese conditions are part of staying on a boatbrbrMarina facilities (showers, restrooms, etc.) are the intended backup in these situations.brbrMARINE SYSTEMSbrToilets are marine systems and must be used properlybrPlumbing and electrical systems differ from residential propertiesbrImproper use can cause outages or disruptionsbrNO REFUNDS FOR SYSTEM CONDITIONSbrbrBy booking, you acknowledge that:brbrAir conditioning is not providedbrOnboard systems (water and electricity) may be intermittently unavailablebrThese conditions are not grounds for refunds or partial refundsbrMarina and hotel amenities are provided as the appropriate alternativebrWORKING VESSEL DISCLAIMERbrbrThis is a real, functioning vessel, not a hotel installation. Layout, access points, and systems reflect that reality.brbrACKNOWLEDGMENTbrbrBy booking, guests confirm they understand:brbrThis is a dockside boat staybrIt operates differently from traditional accommodationsbrThey are comfortable with a marine environment and its limitations

House Boat

SeaLab: 6 Cabin / 6 Head 52 ft Catamaran with Hotel Pools and a Captains Lounge

Key West, Florida, United States

Bed

Bath

Sleeps

$1245.79

Charmayne's Cottages | Your Private Group Oasis in the Heart of Key WestbrbrExperience the ultimate Key West getaway at Charmayne's Cottages—a private collection of six vibrant and charming units located just steps from iconic Duval Street. Perfect for family gatherings, group retreats, or multiple couples traveling together, this unique property offers the ideal blend of shared space, privacy, and unbeatable access to everything the island has to offer.brbrThe Ambiance:brCharmayne's Cottages features six individually styled units, each bursting with personality and island charm. With a mix of cozy studios, a spacious two-bedroom suite, and comfortable one-bedrooms, this property can accommodate up to 14 guests. Some units include full kitchens with stainless steel appliances, others offer convenient kitchenettes or mini-fridges—ideal for everything from quick bites to group meals. Enjoy inviting living spaces, air conditioning, cable TV, and free WiFi across all units, along with cozy outdoor areas to sip coffee or soak up the spectacular Key West sun!brbrGuest Perks:brEnjoy stress-free, contactless check-in with personalized entry codes for each unit—perfect for larger groups arriving at different times. Unit D includes a private on-site parking space, and all other units have access to nearby paid parking options. Beach towels are included for easy beach days, and pet-friendly accommodations mean your furry companions can join the fun too!brbrNeighborhood Highlights:brLocated just off Truman Avenue, you'll find Charmayne's Cottages at the center of it all. Explore Key West on foot from this unbeatable location—walk to the Southernmost Point, Hemingway Home and Museum, Key West Lighthouse, and the Butterfly and Nature Conservatory. Duval Street's legendary nightlife, vibrant dining scene, and quirky boutiques are just a stone's throw away.brbrTransportation Tips:brPlease note that this property includes one designated parking space. Paid parking is available nearby for additional vehicles. We also offer other creative parking solutions, just ask! Key West is a pedestrian- and bike-friendly island, so feel free to explore on foot or rent bicycles, scooters, or golf carts for maximum flexibility. We're happy to offer local tips and transportation recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- All units include air conditioning, cable TV, and WiFi.br- Two exterior security cameras are in place for added safety.br- Guests must be 25 years of age or older to reserve the property.br- Units are located on both the first and second floors.br- There is one dedicated off-street parking space available for use.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrWhether you're gathering with loved ones, reuniting with friends, or planning a group escape, Charmayne's Cottages is your dream destination for an unforgettable stay in paradise. Book the entire property today and enjoy the perfect blend of comfort, style, and location in the heart of Key West!brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Charmayne's Cottages | Private Group Oasis!

Key West, Florida, United States

Bed

Bath

Sleeps

$505.5

THE PROPERTY: Enjoy a soothing cup of coffee on the private patio or take anbrearly morning walk on Mallory Square. This Adult Only home is convenientlybrlocated down a private path and contains sought after features including DadebrCounty Pine and hardwood floors. In addition to modern updates in the kitchenettebrand bath, you will enjoy the charm of old-world Key West. As you enter the home’sbrsunny living room, you will find a sofa, side chairs, and a smart TV. Several windows, skylight, brand vaulted ceiling transform the space and provide an open, airy feeling. French doors brprovide views of palm trees and the patio. brbrOverlooking the living room is the open loft sleeping space with a window and a queen bed under the eaves. Dual night tables, lamps and a reading chair add to the comfort of this second-floor area. Please note the ceilings are sloped. brbrA primary king bedroom is located towards the rear of the home. This first-floor bedroom is adorned with bedside tables and sconce lighting. A window air conditioning unit, ceiling fan and wardrobe storage add to the comfort of this space. A French door provides access to the sunlit brick patio. Just steps from the bedroom is an updated bathroom with single sink vanity and tiled, walk-in shower. Close by is a delightful kitchenette complete with a small fridge, sink, two-burner cooktop, regular drip coffee maker, microwave, and storage. A small table and two chairs are in place for convenience.br brPlease note this home has no washer/dryer at this time. Look no further than Gardenia brCottage for charm, comfort, and convenience!brbrBED CONFIGURATION: One king bed is located on the first floor and one queenbrbed is located on the open second-floor loft.brbrOUTDOOR AMENITIES: A large, shared pool is available for Gardenia Cottage guests; it isbrlocated at the back of the complex and is surrounded by swaying palms and tropicalbrlandscaping. Loungers are in place for your use.brbrPARKING: No designated parking. Limited on-street parking may be available in thebrneighborhood.brbrLOCATION: Historic Old Town, walkable to Duval Street, shops, bars, and restaurants.brEnjoy entertainment and a sunset celebration on nearby Mallory Square.brbrPETS: This home is NOT pet-friendly. (If you have pets, please browse through ourbrmany homes that are pet friendly).brbrSMOKING: This is a STRICT NON SMOKING HOME AND COMPLEX.brbr***Guests must be 25 years of age or older to rent; please note this is an 18 and olderbrcomplex.brbr***Gardenia Cottage is independently managed by Historic Key West Vacation Rentals.brAt this time, it does not participate in any of the amenities and activities offered at the resort***brbr***Outdoor only security camera(s) are in use at this property, and may be used to verify guest occupancy and guest safety. Security camera(s) are not present inside the property.***br***Managed by Historic Key West Vacation Rentals***

Cottage

~GARDENIA COTTAGE~18+ Adult Only cottage near Duval St

Key West, Florida, United States

Bed

Bath

Sleeps

$508.57

THE PROPERTY: Flamingo Cottage is one of several cottages nestled down a gatedbrwalkway. brbrUpon entering this two bedroom/one bathroom home, you will discoverbrthe living room adorned with coveted Dade County pine walls, a vaulted ceiling,brFrench doors, and natural light, all giving the space a sense of openness. Abrsectional sofa, small glass table with guest chairs, hardwood floors and ceiling fanbrprovide a comfortable space for relaxing after a day spent exploring the island. Abrkitchenette is equipped with a microwave, sink, countertop, regular drip coffee maker, brand small beverage refrigerator. Off this area is a first-floor bedroom, complete with two nightstands,brlamps and French doors which lead to that Florida sunshine! Just outside this bedroom is an updatedbrbathroom with tiled walk-in shower and single sink vanity, as well as a small closet. Please note this home brhas no washer/dryer at this time. brbrThe unique second-floor loft overlooks the living room and provides additional sleeping space. This funbrarea has a window and a bed under the eaves that is flanked by two nightstandsbrwith lamps. Cozy up to an enjoyable book on the reading chair under the skylight. Please note ceilings are sloped.brbrIf you are looking for a laidback island getaway in a well located home, let it be Flamingo Cottage!brbrBED CONFIGURATION: One queen bed is located on the first floor and one queenbrbed is located on the open second floor loft.brbrOUTDOOR AMENITIES: A large, shared pool is available for Flamingo Cottage guests; it isbrlocated at the back of the complex and is surrounded by swaying palms and tropicalbrlandscaping. Loungers are in place for your use.brbrPARKING: No designated parking. Limited on-street parking may be available in thebrneighborhood.brbrLOCATION: Historic Old Town, walkable to Duval Street, shops, bars, and restaurants.brEnjoy entertainment and a sunset celebration on nearby Mallory Square.brbrPETS: This home is NOT pet-friendly. (If you have pets, please browse through ourbrmany homes that are pet friendly).brbrSMOKING: This is a STRICT NON SMOKING HOME AND COMPLEX.brbr***Guests must be 25 years of age or older to rent; please note this is an 18 and olderbrcomplex.brbr***Flamingo Cottage is independently managed by Historic Key West Vacation Rentals.brAt this time, it does not participate in any of the amenities and activities offered at the resort***brbr***Outdoor only security camera(s) are in use at this property, and may be used to verify guest occupancy and guest safety. Security camera(s) are not present inside the property.***br***Managed by Historic Key West Vacation Rentals***

Cottage

~FLAMINGO COTTAGE~ 18+ Adult Only cottage near Duval St

Key West, Florida, United States

Bed

Bath

Sleeps

$335.39

The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens offers the quintessential indoor/outdoor vacation experience you've come to the island to enjoy.brbrAnn Street Gardens is a 16+ compound. Regretfully, NO Children under 16 allowed. There is a coin operated Washer & Dryer on the south side of the cottage for use by the units in the compound. $1.00 per load, per machine, at time of writing.brbrThis residence has one bedroom, one full bath, a small kitchen, a living area, and a dining space. But first you'll want to open the doorway from the living room onto the delightful enclosed patio, which then opens to the main attraction-an exquisitely maintained poolside paradise. The shared, heated (in season) pool and landscaped garden area are reserved for the exclusive use of residents of the small enclave your cottage is part of. Chairs, small tables, chaise lounges, and wicker chairs around glass-top tables dot the landscape. Hidden in among the surroundings are more tables and chairs. From any spot you can observe sunshine playing through palm fronds creating a pattern of shadow and bright sparkle over the pool surface. If you look up, you're likely to spot a flock of water birds flying over. Swim, float, sit on the side, and dangle your feet in the refreshing water. Maybe relax in the sun to develop a tan. Or select the shade of a tree for your resting spot where your biggest decision might be whether to read or nap or ponder where you'll go for your next meal.brbrIf you're in the mood for total privacy, you can enjoy the same glorious Key West weather from your enclosed brick patio, part of which is covered and part open to the sky. This area is sizable, really like another room of the cottage, almost doubling the livable square footage. Closest to the house is a small round table with lamp and two chairs under a generous overhang. A little further, in an uncovered area, is a gas grille. Antique bricks under foot and artful arrangements of plants and vases enhance the garden atmosphere. Up two stairs brings you to the second covered area with vaulted ceiling where you'll find a table suitable for serving a meal for one to four. Directly across is a cushioned wicker rocker and large rattan sideboard with six drawers. Above, a Caribbean style ceiling fan with light creates a gentle air flow and illumination for the evening hours. This is definitely the spot where you could barbeque some fresh fish and enjoy it al fresco with a glass or two of chilled wine. Or maybe go out to dinner and return to the patio to spend a few balmy hours sipping cognac under a canopy of stars. brbrThe inside of Ann Street Gardens starts with the living area that includes a wall of glass overlooking the patio. This and other oversized windows throughout fill the cottage with lovely filtered sunlight and views of tropical greenery. The conversation setting includes a deep couch that also serves as a pull-out full bed, an ottoman that doubles as a coffee table, end tables with lamps, and an overstuffed armchair. The opposite wall holds a large flat-screen TV perfectly placed for viewing from the couch or chair. Under that is a brightly painted hutch that adds color, an artistic touch, and storage space. At the end of the room you'll find a small dining table and two chairs nicely placed beside a wall of glass that give you a congenial view as you enjoy a meal here.brbrNearby a doorway opens into the bedroom with queen bed flanked by bedside tables with lamps. Above the bed, a Casablanca-type ceiling fan provides air circulation and light. The room is embellished with art work, two windows, and wall mirror that reflects the romantic scene back onto itself. A flat-screen TV is nicely positioned on an opposite wall for watching the news or latest episode of Nurse Jackie from the bed. An armoire in one corner offers plenty of space for your hanging items and four drawers for folding items. Near the rear wall is the entrance to the en suite full bath, which features colorful tile flooring, shelving, and a well-lit mirror over the sink so you can easily check on your tan lines.brbrThe kitchen is small but perfectly functional with storage drawers, stove, refrigerator, microwave, toaster, coffeemaker, and blender. Again windows on two walls and a cloud white color scheme make this room light and airy and a pleasure to be in. brbrYour vacation accommodations are just the beginning-the whole of America's only Caribbean island awaits. Since Ann Street Gardens provides off-street parking, you'll find it ever so convenient to leave the car and walk or bike everywhere. For example the Historic Seaport and Boardwalk is over just one block. Follow the wooden walkway along the Key West Historic Seaport to find tall ships offering day and sunset cruises out into the Gulf of Mexico or take an all-day ferry excursion to the Dry Tortugas. If you're interested in watersports, you'll find diving, fishing, parasailing, snorkeling, and jet skiing close at hand. If you get hungry, a dozen or so restaurants of varying levels of informality ring the harbor. Maybe sit under a banyan tree filled with tiny white lights at funky Schooner Wharf while you eat a fresh Mahi sandwich, listen to local musicians, and gaze out at a harbor full of boats of all descriptions. Or for a higher vantage point, try the rooftop bar at Turtle Kraals. brbrFrom the Seaport, the world famous Duval Street with its tours, museums, shops, restaurants, and bars is only a block away. Before you walk too far, be sure to check your cell phone for sunset time so you don't miss the daily celebration at Mallory Square. And leave time to hang around for the after party as artists and street performers entertain the crowd with carnival acts, food, and drink. Maybe you've already heard about Dominique and his Flying House Cats, a feline troupe of alley cats that jumps through hoops of fire, walks tightropes, and performs other astounding circus feats.brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.

Cottage

Ann Street Gardens - Downtown Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$260.21

City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Vahevala, your charming Mid Town Key West retreat! brbr brbrThis private home is your oasis, boasting a refreshing pool and an ideal proximity to both pristine beaches and the vibrant Duval Street. At Vahevala, you'll find the perfect blend of relaxation and excitement. Unwind and savor the moment by the pool, cocktail in hand, as you soak up the sun and tranquility of your ultimate relaxation retreat. Indulge in relaxation on the nearby Smathers Beach, embrace the charm of a leisurely stroll along Duval Street, and capture memories with a selfie at the iconic Southernmost Point. Your Key West getaway at Vahevala is ready to make your dreams of sun, fun, and relaxation a reality. brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: Queen Bed brbr brbrBedroom 2: Queen Bed brbr brbrBedroom 3: Murphy Wall Bed (Full Size) brbr brbrFamily Room: Sofa, Smart TV brbr brbrLiving Room: Sofa, Chair brbr brbrKitchen: Nicely Equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Private Pool (heated to ~85 degrees Nov-Apr) brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Off Street Driveway Parking for 1 Vehicle brbr brbr- Linens and towels provided brbr brbr- 0.5 miles to Higgs Beach/White Street Pier brbr brbr- 1.0 miles to Smathers Beach brbr brbr- 1.2 miles to Upper Duval Street brbr brbr- 1.3 miles to Southernmost Point brbr brbr- 1.9 miles to Key West Historic Seaport brbr brbr- 2.2 miles to Lower Duval Street brbr brbr- 2.3 miles to Fort Zachary Taylor State Park Beach brbr brbr- 2.4 miles to Mallory Square Sunset Pier brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited on premises to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, two exterior security cameras monitor the front door and carport. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beaches & Duval Street!

Key West, Florida, United States

Bed

Bath

Sleeps

$432.73

Welcome to Your Private Tropical Waterfront RetreatbrbrLive like a local in this peaceful, private Key West hideaway tucked along the Riviera Canal. This home blends tropical charm with comfort, offering everything you need for an extended stay in paradise. Thoughtfully designed and newly remodeled, it’s perfect for couples, small families, or friends seeking a serene, authentic Key West experience.brbrWith a large private pool, lush native landscaping, and a beautiful outdoor shower, this property embodies the relaxed island lifestyle. It’s a pet-friendly waterfront home ideal for those who want privacy and comfort while being just minutes from Key West’s beaches, restaurants, and attractions.brbrThe SpacebrbrThis cozy home offers three bedrooms, 1.5 baths, and bright, open living spaces that flow easily from indoors to outdoors. You’ll find everything you need for a comfortable long-term stay, including high-speed Wi-Fi, a fully equipped kitchen, and a washer/dryer.brbrLiving Room:brBright and cheerful with beautiful windows that let in plenty of natural light, the living room is furnished with two soft leather sofas, a Stress-less leather recliner, and a large Samsung Frame TV. A bookshelf holds books and games for relaxing evenings, and the open floor plan connects seamlessly to the kitchen and dining area.brbrKitchen & Dining:brThe open kitchen is fully equipped for long stays, with quality cookware, utensils, a coffee maker, blender, and full-size appliances. A large dining table comfortably seats six — perfect for shared meals, morning coffee, or a friendly board game.brbrPrimary Bedroom:brYour private retreat features a king bed, a comfortable mattress, and soft linens for a restful night’s sleep. The room is filled with natural light, cooled by a ceiling fan, and offers plenty of storage for extended stays. Local art and simple coastal décor create a peaceful atmosphere, and a smart TV adds modern comfort.brbrSecond Bedroom:brA cozy queen bedroom with a comfortable mattress, soft bedding, and a desk for a private workspace — ideal for remote work. Includes a small closet, dresser, and a smart TV.brbrThird Bedroom:brBright and welcoming with a queen bed, large closet, small dresser, vanity, natural light, and a smart TV — the perfect spot to unwind after a day of exploring the island.brbrBathrooms:brThe home has 1.5 baths — a full bathroom with a spacious shower and modern fixtures, plus a convenient half bath. Outside, enjoy a private outdoor shower surrounded by tropical greenery — a true Key West delight.brbrOutdoor LivingbrbrThe outdoor space is the star of this property. Step into your own private oasis with a large pool, surrounded by lush, native landscaping for total privacy. There’s plenty of seating for lounging, dining, or reading in the shade.brbrEnjoy the grill for outdoor cooking, the fire pit for cozy evenings under the stars, and the outdoor shower for rinsing off after a swim. This peaceful setting is perfect for morning coffee, afternoon sunbathing, or sunset cocktails.brbrThe home sits on a quiet canal that can accommodate a boat up to 50 feet, giving easy access to both the Atlantic Ocean and the Gulf of Mexico — a prime location for boaters, fishermen, and island hoppers.brbrAmenities at a GlancebrbrTropical, private, and pet-friendly waterfront homebrbrLarge private pool surrounded by native landscapingbrbrOutdoor shower, grill, and fire pitbrbrCanal access for boats up to 50 ftbrbrThree bedrooms (1 king, 2 queens)brbr1.5 bathroomsbrbrFully equipped kitchen and dining for sixbrbrHigh-speed Wi-Fi and Samsung Frame TVbrbrSmart TVs in every bedroombrbrWasher and dryerbrbrAmple storage and workspacebrbrBright natural light and terrazzo flooringbrbrPeaceful residential neighborhood, close to everythingbrbrLocationbrbrLocated on the Riviera Canal, the home offers a peaceful residential setting with quick access to everything Key West has to offer. You can bike anywhere — the beaches, local cafés, waterfront restaurants, and Old Town are just a short ride away.brbrIt’s the perfect location for those who love boating, fishing, or simply soaking up the tropical lifestyle. Whether you spend your days out on the water, exploring local shops, or lounging by the pool, you’ll return to your own quiet retreat each evening.brbrPet FriendlybrbrWe know pets are family! This home is pet friendly for well-behaved dogs (with a small additional fee). The fenced outdoor area and shaded spaces make it a comfortable spot for furry companions to enjoy, too.brbrRates & StaysbrbrDiscounts available for longer staysbrbrMinimum 28-day rentalbrbrUtilities and maintenance includedbrbrProfessionally managed with local supportbrbrGuest AccessbrbrYou’ll have exclusive use of the entire home, pool, and outdoor areas — everything is completely private. Parking is available for one car in the driveway and free parking in street.brbrAdditional NotesbrbrThis home is best suited for small families or groups of friends seeking a quiet, comfortable, and authentic stay. It’s not suitable for parties or large gatherings.brbrWhether you’re escaping winter, working remotely, or simply craving sunshine and calm, this tropical private waterfront home offers the perfect base for a month in paradise.brbrRelax, recharge, and experience Key West like a local.

Key West Lush Tropical Canal front Retreat 3BR Private Pool, Bring Boat & Pet

Key West, Florida, United States

Bed

Bath

Sleeps

$682.8

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrExperience the blend of historic charm and modern conveniences at TASTE OF HAVANA. This 2-bedroom, 2-bathroom cottage located ON world-famous Duval Street offers a front-row seat to the vibrant energy of Key West while providing a private pool and off-street parking for those who appreciate the finer things that come with island living. From the prime location and desirable amenities to having Last Key Realty’s unrivaled Guest Services & In-house Concierge, every detail of TASTE OF HAVANA is curated for an unforgettable island escape.brbrTHE LOCATION...brbrIf you've heard of Key West, you undoubtedly know of the famous 'Duval Street' with its selection of fabulous restaurants, shops, and nightlife. With a prime Duval Street address, TASTE OF HAVANA is truly the choice location for a group that wants to be in the heart of it all. You can enjoy unrivaled people watching from your porch or hop down your steps to any of the attractions within walking distance, including the Southernmost Point, Hemingway House, and famous spots like Sloppy Joe's, and any number of delicious restaurants. Should you decide to venture off the island, you do have one off-street parking space available. brbrTHE LIVING AREA...brbrStep inside to the cozy living space defined by eclectic Cuban décor. The plush sofa sits in front of the flat screen TV for those nights your group stays in. The living room flows into the fully equipped kitchen and dining nook.brbrTHE POOL & BACKYARD...brbrThe true TASTE OF HAVANA lifestyle is found outdoors. Out front, the private patio overlooking Duval Street is the ultimate vantage point for people-watching or enjoying a sunset cocktail as the town comes to life. When you are ready to escape the bustle, retreat to your backyard oasis. Tucked behind lush, tropical landscaping, you’ll find the saltwater pool, heat-optional for year-round enjoyment. This fully fenced sanctuary includes comfortable poolside loungers and a large propane grill, perfect for an al fresco BBQ.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom - with a King bed, flat-screen TV, full closet, and an en-suite bathroom with a walk-in shower.brbr** Guest Bedroom - with a King bed, flat-screen TV, full closet, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TV in Living Roombr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & Cable TV includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked condo also includes, but is not limited to the amenities on this list:brbr** Private Pool with Available Pool Heatbr** Designated Off-street Parking Space for 1 Vehiclebr** Propane BBQ GrillbrbrOther notes:br** Interim housekeeping provided upon requestbr** This property will accommodate up to 4 adultsbr** Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**TASTE OF HAVANA @ DUVAL STREET** Cozy Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$589.46

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrHAVANA ESPECIAL is a charming, single-level 2-bedroom cottage located directly on the world-famous Duval Street in Old Town Key West. This inviting retreat features two private suites and a fully equipped kitchen, ensuring a comfortable stay just steps away from the island's best dining, shopping, and entertainment. Guests can enjoy the quintessential Key West experience from the classic front porch, an ideal spot for people-watching, while the inclusion of a rare private parking space provides ultimate convenience in this vibrant historic district. Combined with Last Key Realty’s Five-Stra Guest Services & In-house Concierge, your trip to the tropics is sure to be one you treasure for a lifetime.brbrTHE LOCATION...brbrIf you've heard of Key West, you undoubtedly know of the famous 'Duval Street' with its selection of fabulous restaurants, shops, and nightlife. With a prime Duval Street address, HAVANA ESPECIAL is truly the choice location for a group that wants to be in the heart of it all. You can enjoy unrivaled people watching from your porch or hop down your steps to any of the attractions within walking distance, including the Southernmost Point, Hemingway House, and famous spots like Sloppy Joe's, and any number of delicious restaurants. Should you decide to venture off the island, you do have one off-street parking space available. brbrTHE LIVING AREA...brbrInside, the home opens into an inviting living area with vibrant Cuban-inspired accents and a unique island flair. The plush sofa faces the flat-screen TV, providing the perfect space for relaxing on quiet evenings at home. The living area connects seamlessly to the home's fully-equipped kitchen and a quaint dining nook.brbrTHE HOT TUB & OUTDOOR SPACE...brbrThe exterior spaces of HAVANA ESPECIAL offer distinct ways to enjoy the island lifestyle. The front porch serves as a premier lookout over Duval Street, providing a front-row seat to the local parade of characters and the perfect backdrop for an evening drink as the night's energy builds. For a more secluded experience, the rear courtyard transforms into an open-air dining room, complete with a propane grill and patio seating ideal for sharing a fresh seafood dinner. The hot tub is a perfect place to end your day with a relaxing soak under the stars.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom - with a King bed, flat-screen TV, full closet, and an en-suite bathroom with a walk-in shower.brbr** Guest Bedroom - with a Two Tin Beds OR One King bed, flat-screen TV, full closet, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TV in Living Roombr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & Cable TV includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked condo also includes, but is not limited to the amenities on this list:brbr** Designated Off-street Parking Space for 1 Vehiclebr** Propane BBQ Grillbr** Hot TubbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 4 adultsbr** Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**HAVANA ESPECIAL @ DUVAL STREET** Cottage & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$779.9

Our spacious Fountaine-Pajot gem, S/V Devine Sailing, features an upper lounge with 360 degree view along with a forward deck with a spacious and comfortable seating area.brRelax in the salon lounge area with a flat screen TV and our selection of movies and USB capabilities.brbrFull kitchen with all the amenities. Full sized BBQ on the aft of the boat to grill your catch of the day'!brbrFive cabins with queen berths, each cabin has en-suite bathroom with shower, electric toilet and vanity. Dry shower stalls in starboard and port forward cabins. All cabins have new bedding, air conditioning, two fans, 110v outlets and dimmable recessed lighting. brbrThe flybridge deck is perfect for those sunset cocktails while you watch the sun dip below the horizon.brbrCrew have their own separate shower and separate bathroom.brbrThe yacht stays docked, the entire reservation, at the Perry Hotel, which invites you to complimentary use of two stunning waterfront swimming pools, live music, three restaurants, gym. complimentary shuttle service, & more. brbrEnhance your stay with a custom charter experience—from sunset sails to full-day excursions or under the stars on one of our overnight luxury sea charters.brbrDue to local regulations, it is required that you choose at least one of the following options during your reservation: a four-hour excursion, a 6-hour excursion, an eight hour excursion, or a 24-hour excursion.brbr- 4-hour excursion: $1900+tax & gratuitybr- 6-hour excursion: $2350+tax & gratuitybr- 8-hour excursion: $2875+tax & gratuitybr- 24-hour excursion: $3370+tax & gratuitybrbrPlease note that the cost of the excursions must be paid directly to our company at the time of booking. The prices listed above include the captain's fee and fuel, however, does not include gratuity. Contact us directly to start planning your unforgettable day on the water.brbrWe look forward to welcoming you aboard and making your dream vacation a reality!

House Boat

5 Cabin Catamaran Sailboat Devine Sailing at The Perry Hotel Marina & Resort

Key West, Florida, United States

5

Bed

5

Bath

10

Sleeps

$1591.08

Ahoy! We invite you to ditch the overpriced hotels and stay on our two luxury yachts at the Stock Island Yacht Marina.brbrWe provide a private, luxury resort style experience where you get tons of benefits for your stay while avoiding the crowds and high prices typical of Key West hotels. brbrWe can help you arrange for an optional ocean excursion during your stay. We do trips as short as sunset cruises or multi-day adventures. All VRBO guests get discounted rates on ocean excursions!brbrWith your booking, you get two comfortable boathouses (docked side-by-side) to stay on with full access to these resort amenities:brbr- Private Beach (one of the only in Key West!)br- Fitness Centerbr- Saunabr- Tiki Barbr- Parking onsitebr- Full time conciergebr- Discounted ocean excursionsbr- High speed internetbr- Transportation options for going to and from Key West (10 minutes drive)br- Waterfront fun like fishing and snorkelingbrbrOur two yachts are called:brbrSomewherebrGrand AdmiralbrbrSomewhere - 4 bedroom super spacious catamaran.brbr- 4 Bedroomsbr- 4 Queensize Bedsbr- 4 Full Bathsbr- Full KitchenbrbrGrand Admiral - 2 bedroom yacht. Extremely comfy and cozy. Plenty of room. brbr- 2 Bedroomsbr- 2 Fullsize Bedsbr- 1 Pull Out Single Bedbr- 2 Full Bathsbr- Full KitchenbrbrWe can accommodate groups of up to 13 people for this listing. brbrIf you have a smaller sized group, don't hesitate to reach out to us to book one boat instead of two. You can book Somewhere or Grand Admiral individually. See our other listings on VRBO or message us for more information. brbrSend us a message here and we will find the best option for your group size and budget. brbrHave a group of more than 12 or want a superb ultimate luxury experience brbrCheck out our largest grandest vessel, Atlantia. Separate listing on VRBO. Or reach out directly and we will show you.brbrSee you out there on the beautiful, serene waters of Key West Florida!

House Boat

Lux Yacht Stay Private Resort Style with Amenities! Pool, fitness center, beach

Key West, Florida, United States

Bed

Bath

Sleeps

$572.39

Welcome to our stunning 4-bedroom vacation home in the heart 15 minutes from Key West! Nestled in the beautiful mangroves, this property offers the perfect escape for your next getaway.brbrAs you step inside, you'll be greeted by a fully stocked kitchen, complete with a stove, oven, refrigerator, grill, and all the necessary appliances and utensils to whip up delicious meals. Gather around the dining table or enjoy a barbecue on the outdoor patio, surrounded by the lush tropical landscape.brbrWhen it's time to unwind, cozy up by the outdoor firepit or enjoy a movie night on the smart TV with satellite/cable channels. For the fitness-minded, you'll have access to the on-site fitness room and equipment. And don't forget to take advantage of the free WiFi, washing machine, and dryer for a hassle-free stay.brbrJust a short 20-minute drive away, you'll find the vibrant Duval Street, where you can explore the local shops, restaurants, and the famous Florida Keys Beaches. For a round of golf, the Key West Golf Club is just an 11-minute drive from your doorstep.brbrProperty features ample parking for your RV and 30 Amp service via external outlet. Waste removal services available nearby.brbrWhether you're seeking a relaxing retreat or an adventure-filled vacation, our 4-bedroom vacation home is the perfect destination. Book your stay today and experience the beauty and charm of the Florida Keys!

Private Paradise, Waterfront Home - 15 minutes from Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$188.05

Summary:brConveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 bath perfect for your next island getaway. brbrIn addition to its prime location, this storybook corner unit features 2 private balconies off of each bedroom and a back deck equipped with all of your outdoor dining necessities. Close enough to everything, but just far enough away Gulf Getaway allows you to enjoy the peaceful serenity of Key West.brbrThe Space:brOn the second floor you will find the 2 bedrooms, each featuring a queen size bed, attached full bathroom and balcony. Perfect for accommodating 4-6 guests, additional sleeping arrangements can be found in the queen pullout couch on the first floor.brbrThe open first floor plan with a half bath is perfect for relaxing after a long day. Equipped with an LG cable tv, complimentary Wifi and French doors leading out to the back deck, the natural sunlight in Gulf Getaway keeps the space bright and airy. From an espresso maker, to a Keurig and smoothie maker, the rooster-themed kitchen is stocked with all of your cooking and drink necessities. There is also a hose outside for washing off sand from the beach and a private back entrance to make accessing the back patio a breeze.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit. brShared Community Features: This home also includes access to the neighborhood pool- exclusive to Truman Annex homes and has lounge chairs perfect for sunbathing. brHow to Access: the bedrooms are located on the second floor with stair access only.brbrThe Neighborhood:brExplore all that Key West has to offer including Truman Annex’s brand new Waterfront park and pier overlooking the Gulf. On Thursdays catch the sunset farmers market at the park or bring the kids to the splash pad for a fun-filled waterpark adventure. Just a 2 block stroll from the world-famous Duval Street, Gulf Getaway is walking distance to endless shopping and dining options.brbrGetting Around:brParking Information: There is assigned parking provided for 1 vehicle. We can provide you with recommendations for parking additional vehicles upon request.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrOther Things to Note:br- In the upstairs hall closet, you will find a stackable washer and dryer.br- Pets Policy: Pets are welcome!brOur requirements are as follows: br•40lb maximum per petbr•$250/per staybr•2 pet maximumbr- This home has a 28-night minimumbr- Mid-stay cleans are available upon request.

Gulf Getaway | Condo w/Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$190.18

Full renovation completed in November 2024. This beautiful townhouse has a perfect location in Truman Annex. Truman Annex is an exclusive gated community within Old Town Key West. Coastal Soul is within walking distance to anything you will want to do...dining, music, bars , shopping, art galleries and more. brCoastal Soul is two story townhouse. The entrance to the main level contains a covered front porch with table and chairs for two. The front door from this porch provides access to the main level which is the living area. The living area contains a fully equipped kitchen with ceiling fan, coffee maker, pots, pans, plates, glasses and silverware. This level also includes a half bathroom, a dining area and living room (with a ceiling fan) and an entertainment center with a 55” flatscreen television. Double French doors from the living room open to the tropical rear yard containing a spacious deck with a table and seating for four. The community pool is just steps from the rear yard gate. The second floor level has two bedrooms and a 2 full bathrooms. The master bedroom is furnished with a queen size bed, has a vaulted ceiling with a ceiling fan, an over sized closet as well as a television. French doors from the master bedroom lead to your own private balcony. The en suite bathroom contains a shower, a vanity complete with amenities such as a blow dryer, soap and towels. The washer and dryer are located in the hallway & is a great amenity for guests. The second bedroom has a full size bed and a closet as well as its own entrance to a private full bathroom. The townhouse has central air conditioning. There are also 2 beach chairs for your use. This unit also has a dedicated off street private parking space.(please see added information for maximum size vehicle in parking info)The townhouse is also a short walk to Fort Zachary Taylor State Park (best beach in Key West) and Waterfront Park. Thank you for your interest in our tropical retreat, the perfect vacation place. brbr**Front door exterior RING doorbell added for security purposes

Truman Annex 2 bedroom 2.5 bath Townhouse- Newly renovated. Steps to pool

Key West, Florida, United States

Bed

Bath

Sleeps

$847.12

Summary:brbrUpscale monthly 4 bedroom, 4 bathroom residence near the waterfront in Key WestbrbrbrbrThe Space:brbrWelcome to Blanco Luxury Villa, a refined monthly retreat in the heart of Old Town Key West, just steps from the waterfront and ideally positioned for guests who value life on the water as much as life in the city.brbrbrbrLocated within Old Town Villas, a secured, gated townhouse community, this beautifully appointed 4-bedroom, 4-bath luxury townhome offers elevated island living for discerning guests — including experienced boaters and anglers seeking a prestigious Old Town address close to marinas, the harbor, and open-water access.brbrbrbrBlanco Luxury Villa is your sophisticated base for a waterfront lifestyle. It features high-end finishes, curated décor, and upscale furnishings throughout, designed to complement long days on the water and relaxed evenings ashore. Spanning three above-ground levels, the home offers space, privacy, and comfort rarely found this close to the harbor.brbrbrbrGround Level: Secure off-street garage parking for one vehicle, ideal for staging gear and supplies, with both front and rear entry access.brbrbrbrFirst Living Level: An elegant yet comfortable main living space — perfect for hosting friends after a day on the water. The gourmet kitchen is fully equipped with premium appliances and quality cookware, well-suited for preparing fresh catches or refined dinners. A dedicated dining area seats six. This level also includes a queen bedroom with direct access to a full bathroom, offering flexibility for guests.brbrbrbrUpper Levels: The second and third floors feature three king bedrooms, each with a private en-suite bath, delivering hotel-level comfort and separation for families, couples, or crew.brbrbrbrResort-Style Amenities: Guests enjoy access to a beautifully maintained, seasonally heated community pool, an ideal place to unwind after offshore runs, harbor cruising, or a full day exploring Old Town.brbrbrbrArts, Dining & Culture: Blanco Luxury Villa places you at the center of Key West’s celebrated arts and culinary scene, when the island comes alive with gallery nights, live performances, literary events, and seasonal festivals — all within walking or biking distance.brbrbrbrNearby highlights include:brbr- Duval Street - Just one block away, offering fine dining, chef-driven bistros, wine bars, galleries, and live music venuesbrbr- The Key West Aquarium and Mallory Square - located directly on the waterfront and within easy reach of the harborbrbr- Museums and galleries — close to the harbor yet tucked into Old Town’s walkable corebrbr- Simonton Street Beach, just a few blocks away, perfect for a sunset strollbrbr- The Ernest Hemingway Home and Museum, less than a mile away, reflecting the island’s literary heritagebrbrbrbrDesigned for Serious Boaters & Anglers: Blanco Luxury Villa is ideally positioned for guests whose lifestyle revolves around the water. Located just minutes from Key West Harbor, the home offers convenient proximity to marinas, charter docks, fuel, provisioning, and marine services — making early departures and smooth returns effortless. Whether you’re running offshore at first light, cruising the harbor, or heading out for a sunset ride, this Old Town location allows you to enjoy the boating lifestyle without sacrificing luxury, security, or walkable access to dining and culture.brbrbrbrImportant Rental Details:brbr- Minimum 29-day stay required.brbr- No smoking permitted.brbr- Pets considered with manager approval and $250 non-refundable pet fee.brbr- Primary renter must be 25+ years old.brbr- Maximum overnight occupancy: 8 guests.brbr- Garage parking limited to one vehicle. There is also a small lot for visitors. brbr- Primary guest must sign a rental agreement.brbrbrbrWhy You’ll Love It: Blanco Luxury Villa offers a rare opportunity to enjoy upscale monthly living near the waterfront in Old Town Key West — where days revolve around the harbor and open water, and evenings return you to refined interiors, cultural energy, and exceptional dining.brbrbrbrFrom early mornings preparing for offshore runs to evenings spent savoring Old Town’s acclaimed restaurants or attending winter performances, this exceptional townhome delivers a sophisticated balance of luxury, water access, and walkable island living — a true home base for discerning boaters, anglers, and long-stay guests.brbrbrbrGuest Access:brbrGuests have exclusive access to the entire townhome, including the garage and all community amenities. Access is private, secure, and reserved solely for registered guests.brbrbrbrThe Neighborhood:brbrLocated in a gated Old Town enclave near the waterfront, the neighborhood offers a rare blend of privacy and walkable access to Key West’s harbor, dining, galleries, and cultural attractions.brbrbrbrGetting Around:brbrMost Old Town attractions, dining, and waterfront areas are easily reached on foot or by bike. Taxi and rideshare services are available, and garage parking is provided for one vehicle.brbrbrbrOther Things to Note:brbrThis property is offered as a 29-day minimum stay. A signed rental agreement is required. The primary guest must be at least 25 years old. Small pet considered with manager approval and $250 nonrefundable pet fee. House rules, occupancy limits, and community guidelines apply to ensure a refined and respectful residential experience.brbrbrbrInteraction with Guests:brbrWe respect our guests’ privacy while remaining readily available before, during, and after your stay should assistance be needed. Contactless check-in.

Condo

Blanco Luxury Villa

Key West, Florida, United States

Bed

Hyatt Vacation Club at Windward Pointe!!! Located in Key West, this villa is a dream. With two cozy bedrooms featuring a king and a queen bed, guests can enjoy restful nights. The villa includes two bathrooms, one with a relaxing jetted bathtub. A nice living room offers a sofa bed, perfect for extra guests or lounging. Comfort is key here, with heating and air conditioning to keep the temperature just right. Whether you’re unwinding after a day of exploring or spending time with loved ones, this superb villa provides a perfect home base. We think our place will help you experience everything Key West has to offer.

Bath

8

Sleeps

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Villa

Gorgeous 2-bedroom villa with AC in vibrant Key West

Key West, Florida, United States

Bed

Bath