Vacation Villa Rentals By Owner In Key West, FL

The Caribbean Suite on the 2nd floor of the Carriage House building at the Hollinsed House is a tropical 2BR/1BA with king beds, full kitchen, living room (with futon)and dining area. This large unit has two balconies with one stretching across the front overlooking the pool and garden area and one located off a bedroom.brAll of our units offer you free access to Wi-Fi since we know you need some of the pleasures from back home. We know you'll enjoy your stay with us. Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon as you enjoy the wonderful weather that Key West offers!! We offer spacious rooms and suites that are designed to fit anyone's budget and taste.brbrOur off street parking is limited to 2 cars total. If the parking spaces are already taken, you may park on either side of the street, as we are located on a ONE way street. Please do not park in spaces marked RESIDENTIAL PARKING (it is painted on the pavement in white letters) unless you have Monroe County license plates and a Key West Parking Permit sticker. You risk the chance of being ticketed. Please be courteous and do not block anyone's driveway.

Apartment

Apartment at The Hollinsed House

Key West, Florida, United States

Bed

Bath

Sleeps

$171.99

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis property is a 30 night minimum. Boat slips available for rent! Inquire with us. brbrFEATURES:brBedrooms: 2 (1 king and 2 twins-can be converted to a king)brBathrooms: 2brLocation: Sunset Marina Gated CommunitybrSquare Feet: 1171brParking: 1 assigned covered parking space (NO ELECTRIC VEHICLES/SCOOTERS/BIKES ALLOWED)brAmenities: Wifi, TVs, in-unit laundry, balcony, shared pool, near the golf course, boat slip availablebrbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Boater's Dream 2Bed 2Bath Condo, 30 night stay w/ water views, balcony, pool

Key West, Florida, United States

Bed

Bath

Sleeps

$182.29

Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the back yard and the pool! brbrThe large foyer and living area with high ceilings convey a spacious and open coastal feel! The dining table and chairs are custom designed with specialty hardwoods and the owner spared no expense with local original art and other high quality art pieces. The kitchen and is stocked with everything you need! brbrThe quaint den off the living room can be closed off with the accordion doors and curtains. It has an antique desk and comfortable chair. Free WIFI is provided! The couch is a queen sleeper sofa and there is also a small closet for personal items. brbrAlso provided are beach/pool towels, beach chairs and two bikes! brbrThere is not designated parking at this property.

Old Town! Spacious Condo in Historic Home w/Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$383.4

This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renovated to accommodate an individual couple, family, or vacationing couples that each desires the privacy of their own bedroom suite with full, private baths. This two bedroom, two and one half unit will comfortably sleep up to six is located in the beautiful community of Truman Annex. This gated community offers the security and tranquility that you would expect on a vacation, yet you are just steps from exploring all that Key West has to offer. Location, location, will be neighbors with the Harry Truman Little White House where President Truman spent many summer days vacationing during his Presidency. The famous Duval Street scene and surrounding blocks encompassing hundreds of restaurants/pubs/shops are only minutes away by foot. Mallory Square, with its nightly entertainment and picturesque sunsets which make Key West a popular destination are just three blocks away. Swimming, snorkeling, parasailing, fishing, and the heated pool are nearby for your enjoyment. Fort Zachary Taylor State Park and one of the best beaches in Key West are just 1/4 mile away. Bicycle and golf cart rentals are aplenty as there is no need for a car. If driving down the scenic Florida keys and keeping the vehicle for your stay, you have the luxury of a reserved, private parking space during your stay. The first floor features a comfortable living room with 60 inch HDTV, sleeper sofa,and half bath. The impeccably appointed kitchen has all housewares items such as pots, pans, and towels. Cable service and high speed wireless internet are available on each floor. The second floor Master Suite has king sized bed, 40 inch HDTV, ensuite bath and french doors that open to private balcony overlooking the tropical landscaping on Front Street. The hallway has a washer/dryer. The third floor suite features two twin beds which can be converted to king size bed depending on your needs. Private ensuite bath and large windows overlooking Front Street as well as a 32 inch HDTV complete this relaxing room. Whether this is your first visit to Key West, or returning for your 'Latitude Adjustment', this newly renovated home at The Foundry in Truman Annex is just what the doctor ordered! brbrPlease note: This property has a 28 night minimum stay

A LATITUDE ADJUSTMENT @ THE TRUMAN ANNEX

Key West, Florida, United States

Bed

Bath

Sleeps

$183.9

Discover a piece of paradise with a beautiful conch home located in the historic district of Key West.brbr4-bedrooms, 2 baths and an open concept kitchen/dining area. Enjoy a nice sunny day on the patio or a rainy night on the front porch. Multiple fruit trees with outdoor security cameras (located: Front entrance, back near deck, and in the back house) for peace of mind. brbrGuests will be given their space for the duration of the stay. If guests would like to receive additional cleaning during their stay, they will need to email or text me.brbrGuests will be charged an additional $500 per cleaning, which will need to be paid prior to cleaning service being complete. House is cleaned using COVID cleaning protocols after each stay.brbrGuests who book will have access to the entire inside of the house. In addition to the front porch and back patio.brbrA long-term tenant resides in the back house, and the side efficiency is occupied by a seamstress for their business.brbrIncludes:brUtilitiesbrStackable washer and dryerbrFree Wi-FibrSmart TVbrbrbrOff-street parking for a compact vehicle or smallerbrbrGuests are within less than 1.2 miles walking distance of:br1. Duval Streetbr2. Fort Zachary Taylor Beachbr3. Mile Marker Zerobr4. Sloppy Joe’sbr5. 801 Bourbon Barbr6. Margaritaville br7. Mallory SquarebrbrAnd so much more.brbrThe rules:br1. Max capacity 7br2. Follow the city noise ordinancebr3. All dishes and towels must be cleaned and placed back in the designated areabr4. Guests need to adhere to local laws and noise ordinances. All fines incurred will be paid by the guest.brbrGuests can walk to pretty much any location in Key West. If guests need to go grocery shopping at either Winn Dixie or Publix, they should order a Lyft, Uber, or Taxi.brbrbr

Quiet Conch House in Historic District

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, have central air conditioning, off street parking, and pool access. This second floor Shipyard Condo has big, beautiful French doors in the living room AND each bedroom. They open onto both front and back balconies with views of the treetops and Old Town Key West. Elegantly furnished, Blue Heavens spa-like atmosphere features vaulted ceilings, ceramic floors and full amenities, including flat screen TV’s and wireless internet access. The living room has a sleeper sofa for guests. After a full day of taking in the island’s many wonderful experiences, come back to the comforts of home. The manicured landscaping, verdant palms, and white picket fences give the Shipyard and Truman Annex a lovely park atmosphere. All this tranquility makes it hard to imagine that Duval Street, Key West’s central artery of entertainment is only two blocks away. New flat screen TV's in living area and primary bedrooms. brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Blue Heaven at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$158.76

Live steps from everything that makes Key West unforgettable. This first‑floor Shipyard condo blends comfort with island charm, offering a bright interior, tile floors, and seamless indoor‑outdoor living through double doors that open to a lush private patio. The gated Truman Annex community provides resort‑style amenities, including a sparkling pool and dedicated parking. From morning walks to the beach to evenings on Duval Street, this location puts the best of Old Town right outside your door.brPlease note: This property requires a 28 night minimum stay

Oyster's Pearl at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$2144.26

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrAccording to the classic song, the best remedy for a belly ache is to put de lime in de coconut and drink 'em bot' up. Last Key Realty now has the best remedy for finding comfortable accommodations for a large group vacationing in Key West: Reserve THE LIME AND THE COCONUT and let us handle de rest! THE LIME AND THE COCONUT is a compound of two side-by-side private homes with a total of six bedrooms, six bathrooms, and an unbeatable location. The benefits of reserving these two homes are plenty:brbr** Two brand new fully-equipped kitchensbrbr** Two spacious living areasbrbr** Two private poolsbrbrLet the combination of Last Key Realty's Five-Star Guest Services and THE LIME AND THE COCONUT be just what the doctor ordered for your group's Key West vacation.brbrTHE LOCATION...brbrImagine being just steps from all of the shops, restaurants, and sites of Key West. Walk just one block to reach the world-famous Duval St, or take a short stroll down Simonton St to watch sunsets from the Historic Seaport. Not only will you be within walking distance of restaurants and entertainment, but you'll also be within a mile of Fort Zachary Taylor State Park, home to Key West's best beach.brbrTHE LIVING AND KITCHEN AREAS...brbrIt's apparent that these homes are special before you even enter them thanks to the gingerbread trim and whimsical front porch swings that grace the façade of each home. Inside, you'll be pleasantly welcomed to newly restored versions of Key West conch homes with bright colors, tall ceilings, and modern furnishings. Each living area boasts a large flat screen SMART TV, which can be enjoyed from the comfort of plush living room furniture. Both living room sofas pull out to an additional Queen bed for extra guests. The kitchens are fully equipped with stainless-steel appliances, along with all of the tools needed to prepare a meal at home. Each home has an indoor dining area, with seating for 6.brbrYOUR PRIVATE POOLS...brbrYour two private pool areas are fully fenced, with a large opening between the two fences that allows you to pass from house to house. Both pools are 6 X 9, perfect for dipping or congregating around for happy hour. Each pool can be heated to your liking and features a soothing waterfall. Comfortable patio furniture provide outdoor lounging options for the whole group. The two outdoor dining sets will comfortably seat 6 when you want to enjoy a meal outside.brbrTHE ACCOMMODATIONS...brbrEvery bedroom of THE LIME AND THE COCONUT is a suite with a private en suite bathroom.brbrHouse 1 - THE LIMEbrbr** First floor Master Suite: King bed and en suite bathroom.brbr** Second Floor Master Suite: King bed and en suite bathroom.brbr** Second Floor Third Bedroom: Two Twins OR one King bed and en suite bathroom.brbrHouse 2 - THE COCONUTbrbr** First Floor Master Suite: King bed and en suite bathroom.brbr** Second Floor Master Suite: King bed and en suite bathroom.brbr** Second Floor Third Bedroom: Two Twins OR one King bed and en suite bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryer br** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen SMART TVs in All Bedrooms and Living areasbr** Fully Equipped Kitchens with Gourmet Appliancesbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home includes, but is not limited to, the amenities on this list:brbr** 2 Private Pools with available Pool Heatbr** 2 Kuerig Coffee Makersbr** 2 Queen Sleeper SofasbrbrOther Notes:br** In person welcome when possible, after hours check in availablebr** Interim housekeeping and grocery delivery/provisioning provided upon requestbr** This property will accommodate up to 16 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** These homes do not include designated parking for vehiclesbr** 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.

**THE LIME & THE COCONUT @ OLD TOWN** 6BR/6BA Compound + LAST KEY SERVICES..

Key West, Florida, United States

8

Bed

7

Bath

16

Sleeps

$298.71

Summary:brbrTropical 3BDR/3BA Home with Large PoolbrbrbrbrThe Space:brbrTucked within lush tropical gardens, this stunning two-story vacation home is designed like a luxury resort or yoga retreat — a place where nature, comfort, and tranquility come together in perfect harmony.brbrbrbrStep through the doors into a light-filled open-concept living space where the living room, dining area, and kitchen flow effortlessly together, creating the ideal setting for easy entertaining or peaceful relaxation. The modern interior is styled with zen-inspired décor and natural materials, giving the home a calming, spa-like feel from the moment you arrive.brbrbrbrOn the first floor, you’ll find two beautifully appointed guest bedrooms, each with its own private bathroom, offering both comfort and privacy. Upstairs, the entire second level is dedicated to the master suite — a luxurious retreat featuring a spacious king-bedroom, a spa-inspired bathroom with both shower and soaking tub, a walk-in closet, and a private porch with plush lounge seating overlooking the gardens and the pool.brbrbrbrOutdoors, the property is nothing short of magical. The pool, designed to resemble a natural pond, is surrounded by peaceful terraces and tropical greenery, creating a soothing oasis for relaxation. The lower terrace offers sun loungers perfect for lazy afternoons, while the upper terrace features a dining area ideal for open-air meals. Fire up the high-end stainless steel grill for a casual cookout, or simply unwind surrounded by the sounds and scents of nature.brbrbrbrEvery window in the home frames a view of the surrounding gardens, turning the lush landscape into a living backdrop and enhancing the home’s serene atmosphere. Whether you’re practicing morning yoga by the pool, sharing meals under the stars, or simply soaking in the peaceful ambiance, you’ll feel as though you’ve escaped to a private luxury spa retreat — but with all the comforts of home.brbrbrbrAdditional amenities include a garage for guest use and plenty of thoughtful touches throughout the home to make your stay effortless and restorative.

Cool Change

Key West, Florida, United States

3

Bed

3

Bath

6

Sleeps

$372.99

Welcome to 734 Passover Lane, a charming one-bedroom cottage nestled in the heart of Key West’s historic district. This idyllic retreat offers the perfect blend of tranquility and convenience, making it an ideal choice for those seeking an authentic Key West experience.brbrPrime LocationbrbrSituated just steps away from the renowned Key West Historic Seaport, guests can immerse themselves in the vibrant maritime atmosphere, enjoying world-class dining, eclectic shopping, lbrbrSituated just steps away from the renowned Key West Historic Seaport, guests can immerse themselves in the vibrant maritime atmosphere, enjoying world-class dining, eclectic shopping, lbrbrNewly redecorated by a one of Key West top interior designers!!brElegant 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 and outdoor shower. The quintessential Key West get-away only 3 blocks away from Duval Street yet quiet and serene. Book this quaint Key West cottage today.

Cottage

This cottage is a 1 bedroom(s), 1 bathrooms, located in Key West, FL.

Key West, Florida, United States

Bed

Bath

Sleeps

$454.02

Fully renovated and furnished 2 bedroom,1 bath cottage in a lovely tropical setting across from the cemetery in Old Town Key West. Only the finest finishes (marble, stainless, dade county pine) in the historical style meant for this special home. Small private cocktail pool, 2 separate outdoor spaces, fully furnished including antiques, screened porch, Comcast cable and Wi-Fi, outdoor shower, central air and heat, washer/dryer, barbeque. Parking space available by request.

Paradise found! 2 br/1 bth restored Old Town home with private cocktail pool

Key West, Florida, United States

Bed

Bath

Sleeps

$127.44

PLEASE NOTE the pool will be closed during the month of AUGUST for repair/resurfacing. Please contact our office if you wish to reserve during this time as we will be offering discounts.brbrThis cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket fences give the Annex a lovely park-like atmosphere. Don't be surprised if you see exotic birds like the snowy egret taking a stroll right in the Shipyard gardens. All this tranquility makes it hard to imagine that Duval Street, Key West's central artery of entertainment is a mere two blocks away.brbrThe two-story white wooden structure at Shipyard has a condo below and above. Yours is above and features front and back balconies. Either is ideal for enjoying what locals call sweet weather, a cup of coffee, or that newspaper or novel you brought along. If you're thinking of a swim, a heated pool with spacious patio is just steps away. For your convenience and comfort, the Shipyard Residents Only pool area provides chaise lounges, high-speed internet, bathrooms, and shower. If you prefer the real beach, the sun and sea breezes at Fort Zachary Taylor are right in the neighborhood. At the beach, have a sandwich and beer at the snack bar or rent an umbrella and chairs to watch the world of swimmers, divers, sailors, kayakers, and jet skiers pass by.brbrBut wait, you aren't even unpacked yet. Enter your vacation home from the front porch, unlock the door to your left, and head up the carpeted stair case. At the top you'll find a welcoming, fluid open floor plan that combines the kitchen, dining area, and living room. A door at the back of the kitchen opens to the front balcony and the living room door leads to the back balcony. The galley kitchen has everything you need to cook a meal at the stove. There's plenty of cupboard space above and every appliance conveniently tucked in below. brbrNext to the kitchen, the dining area provides a round, glass-topped table, colorful table linens, and four chairs. Sitting here you can enjoy the view out the French doors to the back balcony with blue sky and palm trees beyond. Or take your meal outside using the balcony's dining table and chairs. The living area features a bamboo couch, coffee table, and arm chair, all the same warm honey color as the Travertine tile floors. Colorful fish add tropical decoration to the walls. A Casablanca fan whirs above, circulating air throughout. In fact white ceiling fans cool every room whether you're using the central air conditioning or not. A corner-situated TV provides convenient viewing from the couch or chair. Need more seating Just bring in the dining area chairs. brbrJust off the living/dining area are the master bedroom, which features a queen bed, chest of drawers, wall-mounted TV, and plenty of natural light from a large window; a full bath; and a second bedroom with twin beds. Each bedroom offers plenty of closet and drawer space for your flip-flops, shorts, swimwear, sunglasses, camera, hat, you name it. brbrOnce you've settled in, the free-spirited fun of America's only Caribbean island awaits you at the Historic Seaport, on Duval, at the Southernmost Point, or at the beaches along the Atlantic. Check out the tours, museums, water sports, shopping, bars, and over two hundred restaurants, many with open-air seating, some right on the water. While your condo comes with reserved parking, you don't really need a car. From your central location, everything is easily accessible by foot, bike, pedicab, or taxi. Strolling Duval, you might find yourself posing for a photo-op with a pirate, a six-foot-tall drag queen, a Hemingway look-alike, or maybe even Jimmy Buffet in person. brbrWhen you've had enough for one day and head back to your condo to relax and plan for the next day, make one last stop at the Green Parrot for a little live music, a libation, and free popcorn among writers, artists, locals, and visitors. At the corner of Southard and Whitehead (the first and last bar on Highway 1), it's right on your way back to the Shipyard.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.

Shipyard - 2/1 Condo in Shipyard @ Truman Annex

Key West, Florida, United States

Bed

Bath

Sleeps

$969.75

This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort and contemporary convenience.br brThe first floor offers a spacious living room appointed in a soothing green-and-beige palette where you can sink into a fiery coral couch flanked by a classic glass-top coffee table and oriental-style rug. Wicker and wood occasional chairs complete the scene. Open all the windows and doors to invite the soft tropical ambience inside. Or sit in air-conditioned comfort to chat with family or friends while a classic ceiling fan swirls lazily above. Use the Cable TV/DVD player, which you'll also find in the bedrooms above, to view a movie or watch a favorite show. If you're thirsty or hungry, the spotless kitchen and dining table that seats six are just steps away and waiting to be used.brbrMaybe you're ready to lounge outside on the expansive front porch, back porch, or one of the two upstairs verandas. Out back, across the terracotta brick patio, you can refresh in the swimming pool ringed by foliage and shimmering under a cloudless Key West sky. Afterwards check out the pool cabana with bedroom, bath, and inviting open-air shower. When you're ready to call it a night, you can retire to one of the two airy, comfortable bedrooms upstairs in the main house, each with full bath, or enjoy total privacy in the stand-alone cabana.br brYou've heard the term location-location-location. The home you've rented is perfectly placed for experiencing the many charms of Key West. You could start by stepping just across Caroline Street to B.O.'s Fish Wagon for lunch or dinner. As one blogger put it, the place looks like a hurricane just dumped a pile of flotsam on a street corner. In reality, B.O.'s is a favorite locals' hangout where you can order an award-winning fish sandwich as written up in The New York Times. Or, ringing the seaport just beyond B.O's, are a dozen or so eating establishments such as Raw Bar, Turtle Kraals, Schooner Wharf, and Conch Republic.brbrSince the coral island of Key West only spans fourteen short blocks of real estate from the Gulf to the Atlantic Ocean, plenty of other culinary delights-from five-star to street food vendors-are all incredibly close and accessible by foot, bike, scooter, car, pedicab, or trolley. Your choice. Many have Happy Hours from late afternoon to early evening when drinks and appetizers can be enjoyed for half price. And don't miss Mallory Square's sunset celebration where locals and visitors gather to witness and applaud as the sun sinks below the horizon. Once in a while you'll glimpse a brilliant green flash at the exact moment the sun disappears. Hang around for the party as artists and street performers entertain the crowd. Or join the throngs on Duval, browse in an art gallery, or visit the Hemingway House, Truman White House, or Key West Light House and Keeper's Quarters Museum.br brOn the other hand, maybe right now you want to move at a slower pace, on what's famously called island time. To get started, pick up libations and appetizers at Faustos Food Palace, which has been in the same location on Fleming Street since 1936. Expect to shop among writers, artists, families, locals, and visitors. While at this historic grocery store, grab a free copy of Paradise, a publication that comes out every Thursday listing upcoming special events: the music scene, movies, plays, gallery openings, and special events.brbrBring your purchases and reading material back to those comfy lounge chairs by your private heated pool. Snack, swim, sip, read. But don't forget to lather on a bit of sun screen first. If you begin to feel drowsy, let a relaxing siesta overtake you. Maybe when you wake, you'll be motivated to BBQ at your grille or cook something succulent in your fully equipped kitchen. Making the right choices in life are important and you'll know, as your time in paradise comes to a close, that renting the Kemp House has been one of those rights. If a vacation means to escape, relax, lounge, take a break, get away, this has been the absolute right place to do it.brbrThe Property may only be used for residential accommodations. No special events, parties, or functions of any kind are permitted on the Property. If 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.

Kemp House - in the Historic Seaport Area Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$159.33

Impressive. Distinctive. Comfortable. The perfect spot for your tropical get away. This second floor, two bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships, cruise ships, pleasure boats, party boats, and sport boats as you sun yourself or take a swim. The inviting pool is surrounded by lush tropical foliage and has plenty of comfy patio furniture for your lounging comfort. The water is temperature-controlled, and the facility is for the exclusive use of Harbour Place guests. brbrTwo stories up (by elevator or stairs), the balcony of this professionally decorated condo has limited water views from the balcony off the living/dining area. While in another part of the residence, the Master bedroom balcony offers wonderful views of Truman's Little White House Museum where United States Presidents and many other world heads of state have resided over the years. Weddings and other stately ceremonies frequently take place on the lawn under the huge presidential shade trees. brbrBanana Key is beautifully appointed in all new and striking furniture and accessories featuring the lush colors of Key West-ocean blue, sand beige, vegetation yellow and green, with accents of orange and magenta. As you enter from the carpeted and soundproof hallway, you find yourself in the elegant foyer. To the immediate right is one of the two bedrooms. This one has twin beds with fluffy bedding and three large windows to let in plenty of sunlight and moonlight. The white oak floor is dotted with colorful area rugs while a Casablanca-type ceiling fan whirs above circulating air and adding ambience. A three-level dresser, a full closet, a cushioned chair, bedside table with sea shell reading lamp complete the scene. A flat screen TV is perfectly positioned for comfortable viewing from the beds. Immediately to the right of this this room is a full bath with mirrored shower doors, a linen closet stuffed with nubby towels, and tile floor.brbrA right turn from the foyer puts you in a hallway that leads past the washer/dryer closet into the kitchen but not without a door on the right that opens into the Master bedroom with full en suite bath. The four poster king bed has been crafted in a handsome dark wood and dressed in a flower and seashell motif comforter. Nearby a leather loveseat and ottoman offer a place for upright relaxation. A dark wood dresser and ceiling fan continue the striking wood tone throughout the room. In popping contrast to the dark are the cloud white walls and a wall of windows with slatted blinds. Best of all, a glass door opens to a small balcony with seating for two. The one-of-a-kind view is of palm trees framing the Truman White House and grounds. Although you didn't come on vacation to sleep, this room is a true temptation.brbrThe next room is the galley kitchen with double sinks and all the appliances and cabinet space you could wish for. Contemporary spot lighting dots the ceiling in case you want to prepare a meal after dark. A wide and decorative pass-through from the kitchen to the dining area is convenient and adds openness and architectural interest. The square dining table and four high-backed chairs are as ideal for a game of cards or Trivial Pursuit as for a meal. brbrRight beyond is the living room space delineated by a stunning blue & sand hued area rug and blue curved sectional couch that can seat up to six. A glass-top coffee table, green banana plants, and a tropical ceiling fans make this the heart of the living space where you'll sit to watch TV or movies on the flat screen. Also available is cable, high-speed internet, DVD player, and shelf sound system. Ambient light fills the room from the many windows and from the glass door out onto the long balcony outfitted with deck chairs and glass-top table.brbrWhile your condo comes with reserved and covered parking, you'll probably find you don't really need a car. From your central location, everything is easily accessible by foot or bike. Steps from your door enjoy the manicured landscaping, verdant palms, and interconnecting pathways that give your Truman Annex neighborhood its park-like atmosphere. Stroll out the private gates to find yourself immersed in the sights and sounds of the fabulous Duval Street, the island's main artery for tours, museums, and shops of all descriptions. Of course there are bars galore and over two hundred restaurants, many with open-air seating, some right on the water. Don't miss the Butterfly & Nature Conservatory, the Key West Aquarium, and especially the nightly sunset celebration where visitors and locals alike gather in Mallory Square to applaud as the sun slip below the horizon. 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.

Banana Key

Key West, Florida, United States

Bed

Bath

Sleeps

$752.42

Escape to the heart of Key West's historic district and immerse yourself in the vibrant island lifestyle. This 4-bedroom vacation home offers a tranquil oasis just steps away from the lively Duval Street and the stunning Florida Keys Beaches. brbrAs you step inside, you'll be greeted by a spacious living room, where you can unwind and plan your adventures. The fully stocked chef's kitchen, complete with a stove, oven, refrigerator, and a range of modern appliances, invites you to unleash your culinary creativity. Enjoy your meals al fresco on the balcony or gather around the dining table, savoring the flavors of the island.brbrRefresh yourself in the outdoor pool or soak in the bubbling hot tub, both perfect for unwinding after a day of exploring. Stay connected with the free WiFi, and enjoy the convenience of the in-unit washer and dryer. For entertainment, dive into the selection of books and games for kids, or simply relax in front of the smart TV with satellite or cable channels.brbrJust a 10-minute walk away, discover the vibrant Mallory Square, where you can witness the stunning sunset and immerse yourself in the local culture. With this vacation home as your base, you'll be perfectly positioned to experience the best of Key West's historic charm and natural beauty.

Key West Premium Location - Luxury 4BR/4BA – Private Pool by Historic Seaport

Key West, Florida, United States

Bed

Bath

10

Sleeps

$365.23

Summary:brbrYour Island Hideaway in the Heart of Old Town Key West with a Private PoolbrbrbrbrThe Space:brbrWelcome to Windsor Blue— Your Island Hideaway in the Heart of Old Town Key WestbrbrbrbrTucked away on charming Windsor Lane and perched atop historic Solares Hill, Windsor Blu offers the perfect blend of classic Key West character and modern comfort. This beautifully updated 2-bedroom, 2-bath retreat is your personal slice of paradise — just a short walk to Duval Street and all the best restaurants, shops, and attractions of downtown Key West.brbrbrbrThis home is well designed to share with two couples, with plenty privacy. One bedroom and one bathroom downstairs, and one bedroom and one bathroom upstairs.brbrbrbrStart your mornings with coffee on the breezy front porch surrounded by lush island greenery. Inside, you’ll find a light-filled living space with warm hardwood floors, thoughtful architectural touches, and plenty of room to relax after a day of adventure.brbrbrbrThe kitchen is fully equipped with stainless steel appliances, granite countertops, and island seating — perfect for enjoying fresh seafood or a margarita happy hour. The main floor bedroom features full-size bunk beds and exposed ceiling beams, making it ideal for families or friends. Upstairs, a cozy king suite offers privacy, spacious closets, and a modern in suite bath.brbrbrbrStep outside to your private cocktail pool, complete with a soothing waterfall, and enjoy al fresco dining under the stars. With one off-street parking space, a quiet corner lot, and tropical vibes in every direction, Windsor Blue is the ultimate home base for your next Key West getaway.

Windsor Blue Private Pool and Off Street Parking

Key West, Florida, United States

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Bath

Sleeps

$190.05

2 Bedrooms 2.5 Bathrooms. Comfortably Sleeps 4, Max occupancy 6. 1240 total sq. ft.brBedroom nr. 1: 1 King bed, with a balcony.brBedroom nr. 2:, 1 Queen bed. brExtra Sleeping: Queen size fold out sofa couch in the living room, opens to a large patio. brbrWelcome to Duval Street Place - the best location in Key West! Just steps from the exceptional shops and restaurants of the world-famous Duval Street. Within a few minutes walking distance there are many great attractions like the Hemingway House and Museum, Historical Lighthouse, Southernmost Point, and Butterfly and Nature Conservatory. Many other enjoyable sites are also within easy reach on foot: Key West Aquarium, Key West Shipwreck Treasure Museum, Mel Fisher’s Maritime Museum, Harry S. Truman Little White House, and many more! Head to Mallory Square and join the crowds for a nightly sunset celebration. Rent a bicycle, scooter, or an electric cart from a nearby shop and explore the entire island at your pace, or relax at Fort Zachary Taylor Park with the prettiest beach in Key West. brbr28 Day Minimum Rental Only - get a month for the price of a week! A shared pool with plenty of chaise lounges is 45 feet away, adjacent to a large, covered picnic pavilion. A dedicated parking space is located under the building. This two-story town home is on the second floor, nestled above popular restaurants and delightful shops, and is accessible via a secured stairway or elevator either from the garage or entrances outside of the building. If you have additional vehicles you will have to find street parking, as parking in the exterior lot is strictly for Duval Square Mall patrons per the HOA. If you choose to rent mopeds or electric carts, please be sure they all fit in your parking space in the garage. There are bicycle parking racks both inside the garage and outside of the building. New impact windows and doors.brbrUnfortunately, pets are not allowed at this home. brCentral A/C, free WiFi, and cable TV.brUltra-quiet window AC in master bedroom for supplemental temperature control. brWasher and dryer inside the unit. brNo smoking, please.brYou must be 25 years or older to rent this property.brThe rental is non-transferable.

Duval Sq., Old Town, very walkable, full kitchen, pool, parking, 2 BR/2.5 BA.

Key West, Florida, United States

2

Bed

2

Bath

6

Sleeps

$4,136

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrDOS CASITAS is the perfect property for a group of friends or a family that wants to experience Key West together in comfortable neighboring accommodations. DOS CASITAS is a cleverly named combo of two side-by-side private homes with a total of five bedrooms, five bathrooms, and an unbeatable location - half a block off Duval Street on Catherine Street. The backyards connect via a gate, allowing your group to access both homes and gather around the private pool or hot tub. Also included with the rental of DOS CASITAS is Last Key Realty's Five-Star Guest Services & Complimentary Concierge, ensuring you have everything you'll need for the perfect Key West group vacation.brbrTHE LOCATION…brbrIf you decide to pull yourself away from these charming homes, you’ll realize that the best Key West restaurants, live entertainment, and attractions are all within a few blocks of your front door. While you won’t need a car to get around from this fabulous location, there are two driveways (one at each home) to accommodate two vehicles. If you don’t have a vehicle but want to explore the island in a fun way, Last Key Realty’s concierge service can assist with a golf cart, scooters or bike rentals.brbrTHE LIVING AREAS & KITCHENS…brbrCASITA 1 - (aka the Duke of Catherine) was built to be the perfect vacation rental! The living area is open and spacious, feeling light and airy with a gentle tropical vibe. There is a large flat-screen Samsung Frame TV in the living room watchable from the large sofa, which pulls out to a queen sleeper for those extra guests, and the two chairs. The open floor plan seamlessly flows between the living area and the kitchen, creating even more open space and making the home feel even larger. The dining table seats 8 comfortably and the kitchen is fully equipped with every appliance and tool the chef in your group will need.brbrCASITA 2 - (aka Casa Amarilla) has a comfortable living area featuring a large flat screen TV and double French doors that open right up to the tranquil pool area. Off the living area is the fully-equipped kitchen, which includes all of the comforts of home, with plenty of counter and cabinet space. The high-top dining table located just off the kitchen seats 6 comfortably.brbrTHE OUTDOOR SPACES…brbrThe backyards of DOS CASITAS connect via a gate, so your group can easily access each property and mingle with one another.brbrCASITA 1 - The fully fenced backyard features outdoor seating for 6, a propane grill, and a spacious hot tub..brbrCASITA 2 - The fully fenced backyard features a heat optional pool, an outdoor shower, a propane grill, and an outdoor dining set with seating for 4.brbrTHE ACCOMMODATIONS...brbrCASITA 1brbr** Sunset Suite: Located on the First Floor with a King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Ocean Suite: Located on the Second Floor with Two Twin beds OR One King bed, a flat-screen TV, a built-in armoire, a trundle bed with two twin mattresses, and an en-suite bathroom with a walk-in shower.brbr** Queen-sized sleeper sofa in the living room.brbrCASITA 2 - Every bedroom in this lovely home is located on the first floor. No stairs necessary!brbr** Master Bedroom: King bed, large flat screen TV, and en suite bathroom with a walk-in shower. Pocket doors separate this bedroom from Bedroom #2.brbr** Second Bedroom: Queen bed, flat screen TV, armoire, French Doors to the pool area, and access to the shared bathroom off the living room. Pocket doors separate this bedroom from the Master Bedroom.brbr** Third Bedroom: Two Twin beds OR One King bed, flat screen TV, and access to the shared bathroom off the living room.brbrTHESE LAST KEY VACATION HOMES INCLUDE:brbr** 2 Washer & Dryersbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room & All Bedroomsbr** 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 and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, these fully stocked homes also include, but are not limited to the amenities on this list:brbr** Fully Fenced Yardsbr** Private Pool (Heated for an Additional Fee)br** Private Hot Tubbr** 2 Propane BBQ Grillsbr** Off-Street Parking for 2 Vehiclesbr** 2 Queen Sleeper SofasbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 14 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** 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.

**DOS CASITAS @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES

Key West, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

ONLY THE BEST WILL DO…brAn exceptional opportunity to immerse yourself in island life within this renovated, classic Key West style home bordering the desirable Old Town/Casa Marina district. Enjoy a private, lush estate showcasing colorful foliage from every corner and slip inside to your breathtaking home away from home!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brA prestigious glance to this historic home greets you as you pull up to two off-street parking spaces secured by an electric gate with a spacious porch just beyond. A grand entrance into this heavenly retreat displays rich Dade County Pine, large windows inviting natural lighting in, hard wood flooring throughout and an open floor plan for the ideal family gathering. Enjoy a seating area outfitted with cozy furnishings for game night and smart TVs with streaming available. A formal dining area lies steps away with seating for 8. A cheery living room nearby includes a flat screen TV for lazy days - that's if you can resist the temptation of the stunning poolside views beyond the French doors. A fully equipped, gourmet kitchen has been updated with stainless steel appliances, granite counters and bar top seating for 2 to gather around for happy hour. A washer and dryer room is just off the living room area.brbrSLEEPING ARRANGEMENTS…brStep up to the second level to find 3 comfortable guest rooms. There are two king suites with en suite full bathrooms with soaking tubs and walk in glass showers. Steps away is another guest room with twins beds that can convert to a king upon request. The fourth bedroom lies on the third story furnished with two full beds, mini fridge and an en suite full bathroom with a shower. Enjoy a good book seated at the cozy reading nook or out on the rooftop deck in one of the loungers with incredible views. All rooms come with flat screen TV's. Another full bathroom with a shower and outdoor access is also located on the first level for guests using the downstairs sleeper sofas.brbrOUTDOOR LIVING… brExperience your very own slice of Paradise in the outdoor tropical oasis equipped with a retractable awning, an outdoor dining table for 4 and plenty of loungers for well deserved R & R. Island time doesn't get any better than unwinding in the heated, saltwater pool with a calming spillover feature. brbrPARKING...brOff street parking is offered making coming and going a breeze!brbrPETS...brPets are welcome at this home and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. 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!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). brbrTIME TO UNWIND...

SUNCATCHER~4 Bedroom, 4 Bathroom in Old Town with Pool!

Key West, Florida, United States

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