Vacation Home Rentals By Owner In Key West, FL

Receive 1 FREE night for booking for booking a minimum of 30 nights!! Total renovation completed in 2020! This 4-bedroom contemporary home is waiting for your arrival! The Guava Duff (named after the delicious Bahamian dessert my Grandmother Yvonne used to make) was my grandparents’ home, and the renovation was done with the same tender love and care that Mama Yvonne used to make Guava Duff, by my friends and family, and the result is stunning. We took the walls down to the studs, replaced all the plumbing electrical, and windows, then finished it with contemporary flooring, fixtures, appliances and furnishings. It has an open floor plan for the Living room, dining area and new kitchen and boasts 4 separate bedrooms and two full baths. brbrEnjoy a great night’s sleep in our beautifully appointed main bedroom with King sized bed, sumptuous pillows, ensuite bathroom complete with a walk-in full body shower and double sinks. Chest of drawers/tv/two closets and with brand new soundproof windows throughout the house, central air as well as ceiling fans will have you sleeping like a baby! The other end of the house has two bedrooms with queen beds and one bedroom with a twin bed and foldaway bed if needed. Hall bathroom conveniently located near the bedrooms with a walk-in shower. The family area is ample for watching TV, discussing your day in Key West or just sitting back and enjoying on-line content with free Wi-Fi. Head out onto the extra-large front porch to chill, grill, watch people go by, or to watch a rugby or soccer game happening at the brand-new Monroe County Bernstein Park right across the street. Hungry The gourmet kitchen is well equipped with everything you need to create island meals. Dishwasher for easy clean up! Tile throughout the home. Good sized laundry room with full-sized front-loading washer and dryer as well as a laundry sink and door to the side porch. Beach towels also included. Unlike many rental properties on the island, we offer lots of parking at no extra charge. If you have your own boat, there is space to park in front of the house. There are also inexpensive boat slips within 1/2 mile. brbrThis convenient location gives you breathing room from all of the hustle and bustle on the island with a large fully fenced yard. Less than a mile away from great local restaurants and convenience stores including El Siboney, Hogfish Bar and Grill, Hurricane Hole, Roostica, Dolphin Cafe, El Mocho, Dion’s Quick Mart, Jolly’s Liquor Store and CVS. We are also within walking distance of three fine dining great restaurants located at the Perry Hotel and the Stock Island Marina Village- one of the top 50 marina’s in the nation! 10 minutes to Old Town Key West, 14 minutes to Duval St. and 9 minutes to Smather’s Beach!brbrSo welcome to the Guava Duff where you will feel both at home and comfortable and have your own space to enjoy that sweet Key West chill. brbrFeatures of this Property:br• Fully renovated with modern 1100 sq ft of living space/100sq ft front porchbr• Sleeps 8: 1 K, 2 Q, 1 Twin, 1 Foldaway Bedbr• 2 Designer bathrooms with walk-in showersbr• Family Room with sofa/loveseat/ TV- basic cable br• Full gourmet kitchen with dishwasherbr• Parking is FREE- can accommodate at least 4 vehiclesbr• Walking Distance to local Restaurants, Convenience Storesbr• Brand New City Park Across the Street with a Walking Track and Playgroundbr• Free Wi-Fibr• Washer/Dryer/Laundry Sinkbr• Boat Slip with full service just up the street

The GUAVA DUFF - Beautiful KW home with space to chill & lots of FREE PARKING!!

Key West, Florida, United States

Bed

Bath

Sleeps

$629.69

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrStep into VOGUE VILLA, a stylish island escape where timeless Key West charm meets a confident dose of modern luxury. Behind its classic Old Town exterior and welcoming porch, the home has been fully reimagined into a chic retreat layered with curated comforts, designer touches, and a fabulously eclectic aesthetic that feels both relaxed and runway-ready. Teamed with Last Key Realty’s Five-Star Guest Services & Complimentary Concierge, your month in VOGUE VILLA will be the perfect blend of island living and contemporary luxury.brbrTHE LOCATION…brbrVOGUE VILLA is located on Southard St, a half block from the entrance to Truman Annex and the Green Parrot. (Worry not, part of the renovation includes soundproofing in the walls - you won’t hear a thing!) This location is truly the heart of Old Town, steps from all of the shops, restaurants, and sites of Duval Street and the Historic District. Take a short stroll or ride your bike to Duval and experience the best of Key West, such as local favorites like Green Parrot, Sloppy Joe’s, and Virgilio’s. Although you won’t need a vehicle to get around from this prime location, there is off-street parking available in the private driveway for up to 3 vehicles.brbrTHE LIVING AREA…brbrThis home was completely rebuilt from the ground up and it shows in every carefully chosen detail. The tasteful decor perfectly blends island life with modern luxury. The open floor plan and high ceilings in the living room and kitchen make the room feel even grander than it is. There’s comfortable seating and a large flat screen TV waiting for you in the living room.brbrThe kitchen is outfitted with everything you need, including all modern appliances and seating for 8 at the large kitchen table. The beautiful kitchen island has seating for 6 and is the perfect spot for an evening cocktail or a little remote work!brbrTHE BACKYARD OASIS…brbrVOGUE VILLA checks all the boxes, including having an absolutely incredible outdoor space. Step outside to your stunning private pool, framed by lush tropical surroundings providing both ambience and privacy. Whether you’re lounging poolside with a morning coffee or hosting sunset cocktails in your private tiki, this home was designed to make memories. There is a full bath that opens directly onto the pool area, perfect for rinsing off after a refreshing dip.brbrTHE ACCOMMODATIONS…brbr** Master Suite - Located on the First Floor with a King bed, flat screen TV, closet, and en-suite bathroom with walk-in shower and soaker tubbrbr** Bedroom 2 - Located on the First Floor with a King bed, large flat screen TV, closet, access to the hallway bathbrbr** Bedroom 3 - Located on the Second Floor with a King bed, large flat screen TV, en-suite bathroom with a walk-in showerbrbr** Full-sized Sleeper Sofa for 1 in the upstairs DenbrbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Air Conditioningbr** 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, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Private Yardbr** Private Heated Poolbr** Propane BBQ Grillbr** Off-Street Parking in Driveway for up to 2 Full-size SUVsbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 7 adultsbr** Pets Allowed

**VOGUE VILLA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$503.18

This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everything, 2 kitchens, 2 living rooms, 2 dining areas, and back patios. Two of the bedrooms have queen size beds, two bedrooms have 2 twin beds,which can be converted to King beds with a converter kit upon request and there are 2 sleeper sofas. The community pool is just out your back door. brbrPlease note: This property has a 28 night minimum stay

Archipelago at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$348.75

Two Bedroom and 2 and Half Bath beautiful condo in great private Coral Hammock community, close to Golf Course and short Bike ride to beaches and Key West famous downtown. Access to pool in private Coral Hammock community.brHouse has all new bedding, 3 flat screen tv's with cable and internet (wireless), access to pool, rental bikes available close by, bike ride to town and all nightlife and beaches, marina and of course golf. Perfect for family and friends to visit. Full kitchen, quiet and clean. One Bedroom has two twin beds, one bedroom has a queen bed, the couch in living room pulls out for a full size bed.

Key West - Stock Island

Key West, Florida, United States

Bed

Bath

Sleeps

$459.16

Welcome to Be Still – Your Private Island Oasis in Key WestbrbrNestled on an oversized corner lot just a few blocks from White Street Pier and Higgs Beach, Be Still is a beautifully gated home offering the perfect blend of privacy, luxury, and island charm. With ample parking—including gated off-street spaces—this spacious retreat is ideally positioned between Old Town and New Town, making every part of Key West easily accessible.brbrMAIN HOUSE – 3 Bedrooms | 2 BathroomsbrbrPrimary SuitebrKing-size bed, 43” smart TV, en-suite bathroom with Jacuzzi tub, spacious closet, and private access to the pool deck.brbrGuest Bedrooms (2 & 3)brEach features a queen-size bed, 43” smart TV, and large closets.brbrBATHROOMSbrBoth bathrooms include whirlpool/Jacuzzi tubs and modern fixtures.brbrGOURMET KITCHEN & LIVING SPACEbrbrSolid wood cabinets, Corian countertops, and fully stocked with kitchen essentialsbrbrBuilt-in work station—ideal for remote work or e-learningbrbrSpacious dining area and laundry room conveniently located off the kitchenbrbrBright and open living room with large windows, lush garden views, and a 55” smart TVbrbrSunroom with vaulted clear heart pine ceilings, wall-to-wall windows, and French doors that open to the garden—perfect for relaxing with a book or winebrbrOUTDOOR LIVING & ENTERTAINMENTbrbrStep through the atrium doors from the primary suite or living area into your private pool deck and entertainment space:brbrHeated pool with waterfall (available Nov 16 – May 1, $20/day upon request)brbrWet bar with wine coolerbrbrGrill area with lighting for evening cookingbrbrSurrounded by mature trees, lush tropical landscaping, and a full privacy fencebrbrGUEST COTTAGE – 1 Bed | 1 Bath + LoftbrbrThe charming 1.5-story guest cottage features:brbrPrivate street entrance and two dedicated parking spotsbrbrBrick walkways, private deck, and separate washer/dryerbrbrLoft sleeping area with twin beds (convertible to king upon request)brbrFull kitchen, bathroom, dining and sitting areabrbrCentral HVAC and eco-smart water heaterbrbrIdeal for weekend visitors or additional family during your staybrbrADDITIONAL FEATURESbrbrLED lighting throughout the homebrbrEcoSmart point-of-use water heatersbrbrRecently updated high-efficiency central A/C unitsbrbrVaulted ceilings and premium wood finishesbrbrFully enclosed for total privacy and tranquilitybrbrExperience Key West LivingbrbrBe Still is the perfect setting for families, couples, or friends to gather and enjoy the laid-back, beautiful lifestyle Key West is known for—whether you're here to unwind or entertain.brbrLOCATION HIGHLIGHTS:brbrA short walk to Higgs Beach, White Street Pier, galleries, and cafésbrbrQuick drive or bike ride to Duval Street, Mallory Square, and historic Old TownbrbrWe invite you to relax, recharge, and create unforgettable memories at Be Still, your personal slice of paradise in Key West.

BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage

Key West, Florida, United States

Bed

Bath

Sleeps

$266.4

This charming unit has a whimsical nautical feel with the blue and white décor. There are two master suites, one on the second floor featuring a queen bed and one on the third floor which offers 2 twins that can be converted to king on request. This historic 3 level Bostonian style town home is located in the red brick Foundry building in the Truman Annex community. There is a refreshing community pool just across the street. This property also includes one assigned parking space. Conveniently located just 2 blocks from Duval Street and 1/4 mile from Ft Zachary Taylor State Park and beach. Also within walking distance is Mallory Square, known for its breathtaking sunsets and celebration, the Harry Truman Little White House Museum and the beautiful Truman Waterfront park with a splash zone, workout paths and gorgeous views of the harbor.brbrPlease note: This property has a 28 night minimum stay

Life in the Slow Lane at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$537.46

VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attractions and the famous Fort Zachary Taylor Beach. This home has 2 master ensuites with king beds, and there is a total of 4 bedrooms and 3 baths. The second level offers open living and kitchen area, master bedroom with ensuite bath and a great view of the ocean. From the second floor you can enjoy the fantastic view of the harbor and sunsets from the balcony that also has a spiral staircase that leads to the private pool area. Downstairs you have the 2nd king master bedroom with ensuite bath that leads directly to the pool and 2 additional guest bedrooms and full bath. The first guest room has a queen bed and the second guest room has two twin beds that can be converted into a king. Don't miss out on this home as it is one of the few Private Homes in Key West that has a view of the water and located in the Prime Location area here at the Truman Annex Community! brbrPlease note: This property has a 28 night minimum stay

DOLPHIN WATCH at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$681.27

Summary:brbrLuxury queen bungalow suite with twin beds in the loft and a private porch with amazing views. Share two oasis pools, pergola, outdoor bar and grill.brbrbrbrThe Space:brbrEscape the Ordinary...brbrbrbrThe Key West Lighthouse Suite is a cozy queen bungalow home with a double twin loft that sleeps up to 4 guests. This beautifully appointed stand-alone suite remodeled in 2024 is a perfect romantic retreat or ideal for those traveling with children. The suite is directly in front of one of our two new oasis pools with rear pool views. There is also a private front porch with Key West Lighthouse and partial Duval Street views on a quiet Key West Lane.brbrbrbrSuite Amenities:brbrbrbr• Luxury queen-size bed with premium linensbrbr• Upstairs loft with 2 twin beds - can be set up as king upon request - with premium linensbrbr• Luxury well-appointed furnishings and artworkbrbr• Private bathroom with a glass showerbrbr• Private secure entrancebrbr• Spacious front porch with views of the Key West Lighthouse and Duval Streetbrbr• Smart TVs with the latest Roku device for apps and streamingbrbr• High-speed Fiber Wi-Fibrbr• Well-equipped kitchen with refrigerator and icemakerbrbr• Parking space for one vehiclebrbr• Hardwood flooring throughout the suitebrbr• Washer and dryer combo unitbrbr• Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Key West Lighthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds — close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind. This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr• Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr• Brand-new spacious pool decks around each poolbrbr• Six luxury teak chaise loungers with umbrellas and pillowsbrbr• Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr• Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr• A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr• Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr• Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr• Covered bar kiosk for enjoying a cocktailbrbr• Key West tropical foliage throughout the property with lighted step-stone pathsbrbr• Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr• Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3 two-bedroom suites, 2 one-bedroom suites, 1 one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr• The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr• The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr• The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr• Key West Lighthouse Museum, 2-minute walkbrbr• Ernest Hemingway Home and Museum, 2-minute walkbrbr• Blue Heaven Restaurant, 5-minute walkbrbr• Southernmost Point Buoy, 8-minute walkbrbr• Key West Butterfly Conservatory, 8-minute walkbrbr• Sloppy Joe’s Bar, 12-minute walkbrbr• Key West Amphitheater and Park, 12-minute walkbrbr• Mallory Square Sunset, 12-minute walkbrbr• Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!

Key West Lighthouse Suite

Key West, Florida, United States

Bed

Bath

Sleeps

$346.28

Summary:brbrPerfectly Appointed 2BDR/2BA Conch Style HomebrbrbrbrThe Space:brbrWelcome to Your Old Key West Oasis! Experience the charm of Old Key West in this stunning traditional Conch-style home. The spacious downstairs living area boasts a large entertainment space with soaring 12-foot ceilings, creating an airy and inviting atmosphere. The fully equipped kitchen flows seamlessly into the dining and living areas, perfect for gathering with friends and family. Step through the back kitchen door to discover your oversized garden, a tranquil retreat shaded by a beautiful Poinciana tree—ideal for relaxation or casual outdoor dining. Upstairs, you'll find two comfortable bedrooms that provide a peaceful escape after a day of exploring. This property showcases the distinctive features of Conch architecture, including exquisite stained glass details, adding character and charm to your stay. Enjoy the outdoors on one of the two porches on each floor, where you can soak up the vibrant Key West lifestyle. Whether you're sipping coffee in the morning or enjoying a sunset cocktail, this home is a perfect blend of comfort, style, and authentic local flavor. Embrace the spirit of Old Key West—your slice of paradise awaits!

Key Lime Hideaway

Key West, Florida, United States

Bed

Bath

6

Sleeps

Select Dates for Price

Your home away from home in Key West with 3 bedrooms. This adorable townhome features a cozy sofa bed, a comfortable queen bed, and a luxurious king bed. Enjoy the convenience of AC, WiFi, and a washing machine during your stay. Relax in the tranquil atmosphere of this property, complete with a fitness room and two beautiful swimming pools for your use. We look forward to welcoming you to our place.

Charming 3-bedroom townhome with WiFi, AC in fantastic Key West Golf Course

Key West, Florida, United States

Bed

Bath

Sleeps

$310.28

Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gated community of Truman Annex, very near Harry Truman’s Little White House and right in the heart of Old Town Key West; a great spot to watch the October Fantasy Fest Parade as it weaves its way past the front door. Amberjack is within easy walking distance of Mallory Dock, where the sunset is celebrated everyday: Duval Street with its shops, restaurants and entertainments, and Fort Zachary Beach where there is a beachside café and awesome snorkelling. In less than a 2 minute walk there is a deli/convenience store, Coffee Tea Café, Green Parrot Bar and Eaton Bikes where you can hire bikes daily or weekly at a reasonable rate. If cycling is not for you and you don’t want to hire a car, Pirate Scooters (located opposite the Green Parrot Bar) will hire you an electric car. The property does have an allocated off street parking space. Amberjack provides everything for a relaxing vacation. Fully air conditioned throughout with ceiling fans in all rooms. Downstairs there is a large living/dining/kitchen area and a half bathroom. The living area boasts a Cozy sofa that opens in to a luxurious queen bed with a ceiling fan above, two further comfy chairs, a Flatscreen TV/DVD, CD stereo, I Pod docking station and Wi Fi Broadband. There is a fully equipped kitchen and a dining table that seats four with two comfortable stools at the kitchen bar. The patio is furnished with table, chairs, parasol and electric grill; perfect for Al Fresco dining on a balmy Key West evening. Outdoor Grill. The shared pool is just 25 footfalls from the patio gate. Upstairs you will find the laundry area, with stackable washer/dryer, and two bedrooms, one queen and one twin (that can be easily converted in to a king) both with en suite bathrooms, TV’s and balconies with tables and chairs. brbrPlease note: This property has a 28 night minimum stay

Amberjack at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$687.93

bOverview/bbrbrImagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they`ll say hi to one another even if they`ve never met. This is your neighborhood during your stay at the Caribbean Cottage vacation rental. One of the best vacation rental locations on the island - without a doubt. Around the corner `Grand Vin` wine bar stands ready for an evening wine tasting session while `Flamingo Crossing` ice cream parlor offers up a new flavor of home made glace.brbrBrimming with genuine island charm, our Caribbean Cottage, with private pool, was originally built in the early 1900`s. Artistically renovated to maintain the original wood planked polished floors and vintage hand-hewed beams, the owners added bright blue tile (accented with marble), and Bahama style wooden window shutters tat compliment the historic interior. Original pine walls were painted with elegant historic colors of olive and cream and adorned the sash style windows and French linen curtains. Reserved for owner`s use only for many years, original artwork from their private collection is displayed throughout for you to enjoy.brbrThe living room is a generous cottage size with plenty of room to gather. On the side closest to the kitchen, a dining table is placed to create a roomy eating area. The adjoining `butler-pantry` style kitchen is spacious, has a charming French-Caribbean style ambiance, and is fully equipped and easy to cook in.brbrThe interior lay-out of this cottage maximizes privacy with the bedrooms and bathrooms on one side and common living areas on the other. The cottage has two full bedrooms and two full bathrooms.brbrBedding in this vintage cottage includes a king size bed in the master bedroom, and a queen size bed in the other. The master bedroom boasts a beautiful rich wooden armoire, and French doors lead from the bedroom to a pretty outdoor sitting area for reading and lounging. For extra sleeping, the living room has a comfortable queen sleeper sofa.brbrFrom the outside front, the cottage has charming curb appeal with a large beautiful Royal Poinciana tree and the Key West quintessential white picket fence, and of course the porch to sit and watch the world go by. The general design and layout of the cottage lends itself perfectly for versatile use. It is ideal for up to four, and can sleep up to five people comfortably.brbrIf you are looking for a truly authentic Key West experience, this cottage could be the perfect one for you. This charming property is located in the Upper-Duval Street historic neighborhood - a special section of Key West offering many up-scale attractions and interesting features including excellent gourmet restaurants, art galleries, boutiques, a high-end wine tasting store, an award winning home made ice cream shop, a coffee and tea house, South Beach around the corner, and .just a short walk to down to Mallory Square.brbrThere is off-street parking for one full size car, but from here you really never need to get in your car. Upper Duval Street is right out your front door, so forget the hassle of parking and enjoy walking or biking everywhere. Enjoy the island to the fullest, and then come home to relax in the pool.brbrbBedding Summary:/bbr - Master bedroom - King size bedbr - 2nd Bedroom- Queen size bedbr - Living Room - Queen sleeper sofabrbrbIMPORTANT: How payments work/bbrVRBO collects only their service fee. Reservation payments are paid directly to VHKW in two installments in accordance with the terms of your rental agreement (sent for review upon reservation). Payments to VHKW by credit card are subject to an additional 2.95% merchant processing fee.brbrbAmenities:/b Private pool with bricked courtyard garden, fenced yard, fully equipped kitchen. A/C, washer / dryer, smart TV, wifi. Linens and towels are provided.brbrbActivities:/b Shopping, restaurants, nightlife, museums, sailing, boating, snorkeling, diving, theatre, night life, family activities. Everything is within walking distance. Cafe neighborhood features art galleries, wonderful eateries and internationally famous fine restaurants, coffee house, fine gift and clothing stores. Right out your gate find Grand Vin Wine Bar, where you`ll enjoy a broad selection of wine by the glass and Flamingo Crossing, the award winning homemade ice cream store with some of the best ice cream you`ll ever eat. Key West South Beach is a 3 minute walk up the street at most Upper end of Duval St.brbrbArea:/b Upper Duval or `Uptown Key West` has evolved into the `elegant end of Duval` and offers an exceptional variety of restaurants, beautiful boutiques, and art galleries. Walk to South Beach in 3 minutes and the Southernmost Point of the United States is just down the street and around the corner. Walk to the Mallory Square Sunset Celebration in 15 to 20 minutes.brbrbParking:/b Off-street parking for one car.brbrbRestrictions:/b Smoke free house. No Pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrbNote:/b If you love this cottage but need to sleep more than 4 in beds, you can rent it with the one bedroom Vintage Luxury Cottage. You can combine a rental of both cottages and sleep 8 by renting the Fantasy Resort Villa. When rented together, you have two private swimming pools.

Key West Caribbean Cottage - On Duval St w Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$497.99

FLAWLESS SETTING, PERFECT LOCATION…brTucked away on a hidden lane right in the middle of Old Town, this luxurious private, single family home strikes just the right balance of Key West charm and South Beach flair. Enjoy modern, open living space totaling two bedrooms and two bathrooms that extends into a spa-like outdoor area including a patio with flat screen TV, heated pool, outdoor shower, and a European grill. Enjoy being steps away from the energy of downtown yet quickly escape to your own quiet, private oasis.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrFURNISHINGS…brModern, stylish furnishings throughout with hints of local Key West décor. Feel immediately relaxed just by stepping through the front door of this unique retreat.brbrSLEEPING ARRANGEMENTS…brQueen guest bedroom and full bathroom on the first floor. Master king bedroom and full bathroom on the second floor. brbrDETAILS AND AMENITIES…brModern, chic decor pairs beautifully with the wood floors, vaulted ceilings, and rare Dade County pine. Walk through the hallway to the kitchen, which is well equipped with stainless-steel appliances, a keurig coffee maker, breakfast bar, chic farm sink, and full-sized wine cooler. Lounge in the living room furnished with a flat screen TV and comfortable stylish seating. Open the fully retractable French doors to create a seamless, open-air extension to the cabana area; a beautiful private oasis that feels like you are in your own tropical resort. Enjoy the private-heated pool, elegant seating areas, and lush landscaping. brbrPOOL AND OUTDOOR LIVING…brLounge in the sun, float in the pool, or relax in the cabana with a cocktail. Go for a night swim under the stars with the warm glow of poolside lanterns and adjustable mood lighting. Add your own soundtrack with a wireless indoor and outdoor speaker system that you can control right from your mobile phone. The cabana is equipped with an outdoor shower, a grill, dining table, flat screen TV, and couches for visiting, all which is surrounded by bamboo accents, tropical foliage and modern furniture. Park your bike right outside the front door just like an island local with your own personal bike rack. The perfect setting for your perfect getaway! Stay in and indulge yourself in your own private oasis or hit the town with just a few steps - the ultimate stress-free vacation spot that you'll never want to leave.brbrPETS...brPets are considered and a pet fee is required. Please provide size, age and breed prior-to or upon booking. 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)brbrPARKING...brThere is one off street parking space in the driveway of this home.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). brbrLOCATION AND AMBIENCE…SPOIL YOURSELF!

SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!

Key West, Florida, United States

Bed

Bath

Sleeps

$311.49

Stepping through the white picket gate into this town home located in the gated Truman Annex community, in the heart of Old Town, you will find old-world charm along with high-end amenities. The open main floor has a beautifully renovated kitchen, a large sectional-sleeper and a 65 inch television. Upstairs are 2 ensuites each with well appointed recently updated full bathroom. A full size washer, dryer and gas grill are available. Just one hundred feet from the pool, this town home boasts 4 separate outdoor spaces. You will find the spot-on location to all Old Town Key West has to offer. An off street parking spot is included.brbrPlease note: This is a monthly only rental- 28 nights or more

Ascension at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$328.28

Come stay at this bright and airy 2 bedroom, 2 full bath town home in the renowned Truman Annex in Old Town. Conveniently located two blocks from Duval Street with all of the restaurants, bars, shops and night life; two blocks from the historic Truman Little White house; a short bike ride to Fort Zachary Beach State Park, the locals “best beach”; 2.5 blocks to Mallory Square for the nightly “Sunset Celebration”. brWalk into the bright and airy first floor living area with an open floor plan, well-appointed kitchen, one full bathroom, LARGE dining table and lovely sitting area which opens to the partially covered back patio for the Florida outdoor living experience. Upstairs are two bedrooms separated by a full bathroom. The master has one King size bed, French doors open to a balcony with a spot to enjoy your morning coffee. The second bedroom has two twin beds that can be moved together upon request to form one King bed. Full size washer and dryer are located upstairs. The living room and both bedrooms have flat screen TV’s for your viewing pleasure. Stay comfortably and enjoy the beauty of Key West.brAlso, enjoy a dip in the private hot tub on your back patio or refresh with a swim in the “Presidents Walk” community pool, located around the corner from the house. Leave the car at the covered carport and enjoy all that Key West has to offer. brbrPlease note: This property is monthly rental -This property has a 28 night minimum stay

DANCING PALMS @ The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$328.28

The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located less than a half mile from one of the best beaches on the island. The Presidents Walk properties are two level townhouses which have private courtyards on the first level and balconies on the second level. Outdoor Grill. Each bedroom has one queen size bed. All properties are outfitted with washer/dryer, pots and pans, towels and linens, have central air conditioning, off street parking and pool access. brbrPlease note: This property is monthly rental - This property has a 28 night minimum stay

Sago Palm at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$2696.07

This isn't just a house, this is your own private mini resort in Key West, Florida. THERE IS NO OTHER PROPERTY THAT COMPARES TO THIS IN KEY WEST- 500 FEET OCEANFRONT. This is the property used by MTV to film the 2006 Real World Key West. 500 feet of oceanfront, 8 bedrooms (sleeps 18) , 4 1/2 baths,11 plasma TVs, pool table (and ping pong), tennis court (optional), racket ball court (optional with Guest House), 2 paddle boards, 2 kayaks, basketball hoop, off street car parking, 60 foot long deep boat dock, 100 foot shallow boat dock, plus secondary protected dock for storms and weather. This property is by far the best Key West has to offer! Off season specials available. Perfect for large family getaways, small business retreats. Call early as it gets filled quickly.brTHE RESORT COMPOUND CONSISTS OF THE LARGE 8 Bedroom House used by the Real World Key West series SLEEPS 18 and an additional optional guest house, SLEEPS 4, (called the Racket Ball House) literally built around a racket ball court with 2 waterfront bedroom. The additional house is rented as an additional option if wanted. PLEASE NOTE THAT THIS PROPERTY IS ONLY REPRESENTED BY THE OWNER ANDREW LIPPI. ANY OTHER PERSON INCLUDING A CRAIGSLIST LISTING IS NOT AUTHORIZED AND PROBABLY A SCAM.

Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort

Key West, Florida, United States

Bed

Bath

Sleeps

$1056.38

Located in the heart of Old Town Key West, just steps from restaurants, shops, and local attractions, this well-appointed three-bedroom townhome offers a comfortable and convenient retreat. The home features one king bed and two queen beds, making it ideal for families or groups.brRelax in the living room, which includes a comfortable sofa bed, or enjoy the ease of two full bathrooms, each equipped with a shower and hair dryer. Air conditioning throughout the home ensures a cool and comfortable stay year-round.brWhether you’re unwinding indoors or heading out to explore everything Key West has to offer, this townhome provides an excellent home base for your visit.

3-bedroom townhome in beautiful Key West with AC and charm

Key West, Florida, United States

3

Bed

Bath

8

Sleeps

$192.99

Embrace the Enchantment of Old Key West Charm!brbrEscape to the enchanting world of Key West Hideaway, where history meets comfort in a vacation rental that whispers tales from 1928. Nestled in a quiet gated community of seven houses, this meticulously curated conch house invites holiday travelers, business professionals, and wandering nurses to experience the allure of Old Town Key West like never before.brbrBedroom Bliss:brbrMaster Bedroom - Lavender Haven: Unwind in the cozy master bedroom with a California king-size bed adorned with a lavender quilt set, golden curtains, and rattan furniture. This space features a large captivating beach scene painting, echoing the serene charm of grassy beaches from the US Northeast. Unique solid oak French doors open into this relaxing retreat.brbrVersatile Retreat - Study Turned Bliss: The central bedroom/workspace beckons with pastel green quilts, a serene blue desk, and a daybed that transforms into a king-size bed. Original double French doors lead to a room decorated with beach-themed accents and a whimsical pineapple-shaped lamp.brbrBath Haven:brIndulge in the spa-like large bathroom featuring a shower-bath combo, a wooden vanity cabinet with cerulean blue accents, and star-adorned cabinet knobs. The beachy charm continues with blue starfish decorations and convenient blue shelves above the toilet.brbrPorch Delight:brSip your morning coffee or unwind on the screened porch, adorned with a small teal metal table, teal chairs, and a swing. Breathe in the island breeze and let the soothing ambiance of Key West embrace you.brbrLiving Room & Kitchen Extravaganza:brStep into the heart of the home—a spacious living room and kitchen area. Vaulted ceilings, exposed beams, and whitewashed Dade County pine walls create a sense of openness and tranquility. The entire ceiling can be illuminated with LED lights for setting the perfect mood. The fully equipped kitchen features an induction stove and oven with an air fryer, microwave, toaster and dishwasher. The kitchen area is seamlessly integrated into the living space, making it ideal for gatherings. There are wine glasses and champaigne glasses available for your romantic moments or celebrations. brbrPoolside Paradise:brThe pièce de résistance is the large pool shared by the friendly gated community of seven conch houses. Dive into the refreshing waters, bask in the Florida sun, or simply revel in the serenity of your private escape.brbrTropical Gardens:brSurrounding the property are exotic tropical plants, including palm trees, pineapple trees, coconut trees, and a charming herb garden with Tree Spinach, Rosemary and Thai Basil, enhancing the lush and serene environment.brbrAdditional Amenities:brThe property also includes several bikes for exploring the island, a convenient washer and dryer unit, and a gas grill for outdoor feasts.brbrAt Key West Hideaway, we invite you to unlock the door to a furnished vacation rental that transcends time, offering a perfect blend of historic charm and comfort. Your Key West Hideaway conch home is situated at the far end of the property, providing additional privacy and serenity. Your escape to Key West begins here, where memories are made, and every detail whispers the promise of a truly unforgettable stay.

Charming 2-bedroom House in Historic Key West with Pool

Key West, Florida, United States