Vacation Rentals By Owner In Key West, FL

Our sweet ‘conch’ cottage in old town Key West has been completely redesigned and custom crafted by 2 architects as our home away from home and we offer it as a MONTHLY rental when we aren’t using it ourselves. It is located in a wonderfully private yet centrally located neighborhood on a hidden lane. as our home away from home. This intimate house boasts many fun and thoughtful features which will help make your stay in Key West special. It has a lovely small freeform heated pool (with a salt water system that feels like natural water and a built-in bench), and a relaxing patio in a private backyard - complete with outdoor eating area and a wonderful outdoor shower (with hot and cold water!). Swim, eat, and watch butterflies and birds under the palms....brbr This is a classic compact 'Conch' house, typical of old Key West. This house is in a truly quiet, residential neighborhood just a few short blocks to Duval Street, the boisterous hub of town. Although on the cozy side, we designed it to be light and airy and is decorated with lovely modern furnishings, wireless broadband internet service (reaches the pool area as well), living/dining/kitchen area and it even has a second comfortable living room complete with a smart TV. Both downstairs bedrooms also feature flat panel smart TVs. brbrThe house is perfect for your retreat both inside and out. Inside it's cool with tile floors, central air, cathedral ceilings, a full, modern kitchen, 2 bedrooms plus a comfortable carpeted loft with 2 twin beds in one room and a double futon in the other (accessed via a steep stair). We also have 2 lovely tiled bathrooms - one with a creatively tiled tub/shower and the other with a tumbled marble tiled shower. All beds are comfortable with new mattresses! Our home is strictly non-smoking. brbrWe have provided everything you’ll need to make you feel right at home including a small collection of books, a fully stocked kitchen, a gas grille (with gas provided) and cooling ceiling fans in every room. Call us for current availability and rates for your stay. We are open to accepting pets and have a separate pet fee (if pets accepted) with an additional mid-monthly cleaning required. brbrAll you need to bring to this lovely island is your bathing suit, a pair of shorts and flip flops and come enjoy the beauty and diversity that Key West has to offer! brbrHere's a quick To Do list I sent to someone recently: 'So much to do here! Taking a sand bar trip out to the reef (about 5 miles out) is great - can combine it with sunset, parasailing is awesome, best beach for swimming/snorkeling is Ft. Zachary Taylor - not perfect sand (lots of coral) but lovely place with beach chairs for hire too, great dining all over - definitely try our local fine dining restaurant Lola’s for a splurge (2 seatings per night- call for reservations), we also love El Siboney - a locals Cuban place, really tasty croissants at Moondog Cafe, great place for cafe con leche/breakfast is 5 Brothers on Southard/Grinnell, La Te Da has fabulous high class drag shows and dinner, rent bikes from Eaton St bikes (they’ll deliver and pick up) or rent a scooter or golf cart for the day. That's for starters. Don't need to bring many clothes or fancy shoes - very casual and carribean. Flip flops work well here day and night!brp.s. At the house we've left a couple of binders stuffed with menus and things-to-do and places-to-go while you're in town. We hope you find Key West as enchanting as we do!brbrKeywords: House, private house, house rental, bungalow, cottage, pool,single family house

Cottage

Oasis in Old Town - our special home

Key West, Florida, United States

Bed

Bath

Sleeps

$816.61

The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded and private. The raised vaulted ceiling creates an open living environment. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double hung sash. All linens and towels are furnished. The house has a Starlink high speed wi-fi network, streaming internet TV, a 32 Sony SMART HDTV, and a 26 Samsung SMART HDTV. The house has central air conditioning (three (3) zones), a ceiling fan, and a stacked LP washer and dryer. There is a stainless steel propane barbecue located on the pool deck.brbrThe house can comfortably accommodate a maximum of five (5) guests – who are comfortable sharing an open social living environment.brbrFIRST FLOORbrThe kitchen, living/dining room, small bedroom, bathroom. There is a queen sleeper sofa in the living room, and a 32 Sony SMART HDTV, in the living room. There is a full bed in a small bedroom located between the kitchen and the living room. The bathroom, located off the small bedroom, has been recently completely renovated – it has a vaulted ceiling, recessed lighting, oak cabinets, and black granite vanity top.brbrKITCHENbrThe kitchen has serve thru access to the dining/living room. The kitchen ceiling is vaulted with recessed LED lighting. There is a stainless steel gas range, a stainless steel refrigerator, microwave, Braun coffee maker, garbage disposal, Krupps toaster, pots & pans, all basic cooking utensils; and dishes, flatware, glasses (service for 6). There are (2) French doors providing access to the rear deck where the washer and dryer are located.brbrLOFT SLEEPING AREAbrA ladder is used to access the loft sleeping area. The loft has a full size bed, and a 26 Samsung SMART HDTV.brbrCOMMON ELEMENTSbrThe five (5) house compound is private and secure with a 25' x 10' heated pool including a 5' x 10' heated Jacuzzi. In addition, there is a 10' x 8' heated Jacuzzi. There are brick walkways, and a 40' x 10' sun deck, including a stainless steel propane barbecue, chaise lounges for sunbathing and relaxing; and tables and chairs for dining. Throughout the property there is Starlink secured wireless internet access, and CCTV security monitoring. The design of the property lends itself perfectly for small gatherings with friends and family.brbrLANDSCAPINGbrThe landscaping is lush including various palm species, Poinciana, Spanish limes, avocado, bananas, hibiscus, bougainvillea, halliconias, bromeliads, and orchids, brick walkways.brbrEXCELLENT LOCATIONbrThe house is located in Old Town Key West at the corner of Thomas and Angela Streets - (2) blocks west of the center of Duval Street in one of the oldest sections of Key West; (4) blocks east of Fort Zachary Taylor State Park/Beach, the best beach and picnic area in Key West. The gated compound is within easy walking or biking distance to everything in Old Town Key West, Duval Street, and the best entertainment and dining on the island.brbrCHICKENS & ROOSTERSbrThe City of Key West protects chickens and roosters, and considers them as part of the history and charm of Key West. As a result, Key West and many of the islands throughout the Florida Keys have free-range chickens and roosters. You will definitely see and hear chickens and roosters during your stay in Key West. Some visitors to Key West love them, and some visitors hate them - personally, I enjoy them best roasted, with plantains, and black beans and rice!brbrCRITTERSbrAlso, please remember that you are in the tropics and most life forms typically thrive in the tropics. Please don' t be surprised or alarmed if you see a lizard, or an insect.

Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5

Key West, Florida, United States

Bed

Bath

Sleeps

$587.09

Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and all that Key West has to offer. brbrThe house is furnished in a coastal cottage décor. The living room has a sofa and seating area that overlooks a quiet deck, that is perfect for drinking your morning coffee. Kitchen is fully equipped with everything you could need, microwave, toaster and coffee maker. Dining area with table and seating for 4 or you can eat outside on the deck under the beautiful banyan tree. The banyan tree provides shade to the side deck. The master bedroom has a King size bed with an armor, desk and TV. The 2nd bedroom has two twin beds (that can be made into a king, when request). The home has 2 bathrooms, perfect for those that don’t want to share. Home has high speed Wi-Fi, cable, central air and ceiling fans in every room, linen for all bedding.

Little Paradise, Historic Harbor Old Town Key West 2/1.5

Key West, Florida, United States

Bed

Bath

Sleeps

$851.78

Please choose a Saturday check-in, all rentals will be in seven night increments.brBedding configuration may vary, depending upon your travel week and the villa available, please inquire prior to booking.brThank you for your interest in booking with Dash Realty Group, Windermere Florida. brDash Realty Group is registered in Florida as a licensed Fla. Seller of Travel Ref. No. ST42435.brbrOverlooking the Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resort's observation deck guarantees a stunning view from sunrise to sunset, and even to gaze at the stars. Rent a boat for a private viewing of the Keys or take a jetski for a spin right from the resort's marina. Work up a sweat at the on-site exercise room and afterwards, relax your body and mind in the sauna.brbrThe resort's 90-slip marina accommodates boats up to 150 feet and hosts a variety of water activities. After you've had your fill of fun on the water, stretch out on the private beach or outdoor pool. If you want to venture out and explore the island, there are local attractions, art galleries, shopping and restaurants within walking distance of the resort's doorstep.brbrA two-bedroom suite sleep up to six, and include a full kitchen, dining area and decked out living area. Villa is furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West.brbrThe Galleon Resort is perfectly positioned, sitting only two blocks from Duval Street - a legendary road that boasts top-notch restaurants, dazzling nightlife and non-stop soirees. Party until dawn at a carnival, swing by a cuban cigar stand or bring your camera to the exotic butterfly conservatory, all located on this versatile street that's earned its reputation. At the northwest end of Duval Street lies Mallory Square, a plaza which is famous for its Sunset Celebration - tourists gaze at the sunset while arts and crafts displays and entertainers amuse the gatherers. Key West's oldest attraction, the Key West Aquarium is a hit with families - everyone will enjoy scoping out the menagerie of rainbow-hued fish.brbrLarge waterfront swimming poolbrPrivate beachbrBoardwalkbrObservation deck with a 360-degree panoramic viewbrof Key West ... one of a kindbrDock CafébrTiki BarbrSaunabrDiving & SnorkelingbrSun BathingbrSunset CruisesbrExercise Roombr24 hour securitybrWireless InternetbrbrThe Galleon's Marina offers dockage space to accommodate boats and yachts up to 140 feet. Outside of being the most highly protected harbor for your vessel, they also offer exclusive marina and resort amenities when renting a boat slip in the Marina. Wet slips are available for both seasonal and transient rentals.brbrFishing Charters, Sunset Cruises, Parasailing, Snorkeling, Dolphin Watching, Glass Bottom Boat Jet Ski Rental, Scooter rentals, all available onsite or nearby.brbrTHE BOOK IT NOW FEATURE IS A REQUEST FOR RESERVATIONS, NOT A CONFIRMED STAY. Please do not reserve your airfare until you have communicated with us and have an executed rental agreementbrbrBooking through VRBO is fast and easy. Dash Realty Group will email you the updated confirmation once you book thru VRBO. Please note that VRBO provides an instant quote that may not be accurate and may require us to send an adjusted price quote and adjusted dates based on what is available for your requested dates.brThis is based on higher demand weeks and resorts that may be higher than the initial quote. The VRBO calendar does help provide instant availability and estimated price quote. However, because availability and rates vary constantly, the calendar feature and instant quote feature is not always 100% accurate. brbrThe photos are a good representation of what your villa will look like. Layouts may vary. The resort updates and maintains the villas at this resort and your villas is assigned upon check-in.

The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!

Key West, Florida, United States

Bed

Bath

Sleeps

$408.71

VINTAGE ISLAND PARADISE...brTucked within luxuriant foliage lies this timeless, adult only, tropical sanctuary in the midst of Old Town Key West. Elegant architectural design with an unmatched collection of artwork, this mature retreat creates a blissful ambiance. A well known ficus tree among the infinite landscape makes this the legendary Ficus House.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE. THIS HOME IS NOT SUITABLE FOR CHILDREN.brbrDETAILS AND AMENITIES...brAn enchanting front porch greets you with seating for 5 overlooking this pristine paradise. Step inside to find impeccable interior design and every conceivable amenity one could desire. A rich, aesthetic wood wall and floor planking enhance the historical character, which also flows into a chic, updated kitchen/dining room blending the appliances and cabinetry. A large kitchen table fills the space allowing for a fun, interactive cooking experience. Steps away is a light-filled sunroom lined by large doors that can be perched open to create a welcomed indoor/outdoor space. A stunning living room off the kitchen offers cozy furnishings with a flat screen smart TV equipped for your own personal login for streaming. brbrSLEEPING ARRANGEMENTS...brThe gorgeous master suite overlooks the pool area and comes with a queen bed, TV and an en suite full bathroom with a rain shower. The 2nd guest room comes equipped with a large office desk with 2 monitors for those working remotely as well as a queen Murphy bed. Open the doors off this room to a private deck with seating for 2, free weights and an invigorating outdoor shower. The guests occupying this room can utilize the nearby powder room off the living area. Beyond the pool lies a private guest cottage showcasing cathedral ceilings, two twin XL beds that convert to a king, a TV, bathroom with shower and a convenient mini fridge and keurig to allow for morning cups of coffee under the cottage porch awning. A sofa sleeper resides in the living room area and a washer and dryer can be found just on the other side of the cottage.brbrOUTDOOR LIVING...brFenced in for ample privacy, this picturesque dream sets the tone for your much-needed tranquil seclusion. The heated, volleyball style pool is the focal point of an expansive red brick patio enveloped by swaying palms. This area becomes illuminated after sunset creating a magical space for evening cocktails as you star gaze in the loungers. Dine al fresco after grilling out on your gas grill and soak up the island breeze during happy hour. A quaint neighborhood calling for afternoon strolls, this home is peacefully located yet blocks away from all the adored attractions. brbrPETS...brNo pets please.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...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.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...brReservations cancelled at least 60 days prior to arrival will receive a full refund. Cancellations less than 60 days prior to arrival may receive a refund if we are able to re-rent the dates. brbrTHE HEART OF KEY WEST...

THE FICUS HOUSE ~ Adult Only, Lush 3 BR, 2.5 Ba Gem with Pool and Cottage!

Key West, Florida, United States

Bed

Bath

Sleeps

$182.33

Enjoy the lovely Key West ocean breeze from your private Tree House. This is the quietest area of Old Town but only4 blocks to the beach, 3 blocks to Duval, you will not find a better or quieter location to enjoy all that Key West has to offer. Its less than 4 blocks to Blue Heaven, Santiago's, Moon Dog Cafe. br This storied and historic 1883 Conch home has been lovingly and thoughtfully renovated to perfection. Gleaming Dade County Pine floors and walls, period windows, period bath fixtures will welcome you to the Tree House , a Conch Classic centrally located in Old Town. The Tree House is super private and safe nestled with in a fenced and gated compound with lovely landscaping. The house is furnished with fine furnishings from Tommy Bahama, Lexington and Century. It is outfitted with fine linens and kitchenware.br The renovated second story home is over 1000 sq ft of indoor living space , plus a huge balcony with a dining area for 4 , plus couches. There is also a lovely front porch for taking the sunset or chatting up the locals. br The house is configured with two bedrooms with queen beds, a pull out queen sofa in the living room, and a twin day bed in the front entry perfect for a child or overnight guest.br The Tree House can be configured with the downstairs 1 bedroom1 bath Conch Haven for large groups sleeping 11 comfortably.br Smoking is allowed on the porches and small pets are welcome.

Old Town Beauty built in 1883

Key West, Florida, United States

Bed

Bath

Sleeps

$502.77

***This unit holds a City of Key West Transient License and will be permitted to continue offering weekly rentals beyond 2025*** brbr brbrWelcome to Cocktails & Dreams, an impeccably updated second-floor condo located in the coveted Shipyard Condominiums! brbr brbrPositioned at one of Key West's prime locations, this residence offers you an unparalleled Key West experience. Just a short 2-block stroll from the vibrant energy of Duval Street, Cocktails & Dreams places you at the heart of Key West's renowned dining, nightlife, and shopping. Explore a plethora of restaurants, bars, and unique boutiques, immersing yourself in the dynamic spirit of the island. Venture to Truman Waterfront Park for a day of family enjoyment, creating cherished memories. If relaxation is your goal, the soft sands and inviting turquoise waters of Fort Zachary Taylor Park are only moments away, offering a tranquil escape. When the allure of the complex beckons, retreat to your private front or rear balcony. Begin your day with a cup of coffee and the soothing morning breeze, or unwind in the afternoon with a cocktail as you soak in the island vibes. For those seeking refreshment, the community pool (closed August 2026 for renovations) offers a delightful way to beat the heat. Take a leisurely dip, enjoy the sun's warmth, and relish the ease of having your relaxation needs met right on-site. Inside, Cocktails & Dreams is meticulously updated, providing you with modern comfort amidst the vibrant island atmosphere. Discover a harmonious blend of convenience and style that enhances your Key West stay. Whether you're an adventurer or a leisure seeker, Cocktails & Dreams places all the wonders of Key West within your grasp. Uncover the magic of this island paradise, knowing you have a comfortable haven to return to. Discover the essence of Key West living at Cocktails & Dreams. Experience the luxury of convenience and the allure of the island lifestyle. Book your stay now and let your Key West dreams come to life! brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom 1: Queen Bed, Smart TV brbr brbrBedroom 2: Two Twin Size Beds, Smart TV brbr brbrLiving Room: Sofa With Pull Out Bed, Two Chairs, Smart TV brbr brbrKitchen: Nicely Equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Pool (Pool will be closed August 2026 for renovations) brbr brbr- One Designated Parking Space brbr brbr- Keurig, Drip Coffee Maker, Toaster brbr brbr- Linens and towels provided brbr brbr- ~3 blocks to Duval Street brbr brbr- 0.3 miles to Fort Zachary Taylor State Park Beach brbr brbr- 0.7 miles to Southernmost Point brbr brbr- 0.8 miles to Mallory Square Sunset Pier brbr brbr- 0.9 miles to Historic Seaport brbr brbr- 2.6 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPet Policy: Pets are not permitted for guest bookings less than 30 days per the HOA. For guest bookings 30 days or more, up to one dog 25 LBS or less will be considered with a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMilitary Discount: A 10% discount is offered to active duty, retired, or reserve armed forces personnel with a valid military ID. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, one exterior security camera monitors the front door. The camera is for security purposes only and does not monitor any private interior or outdoor living spaces.

Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!

Key West, Florida, United States

Bed

1

Bath

4

Sleeps

$347.13

Summary:brbrQuintessential Downtown Key West CottagebrbrbrbrThe Space:brbrDowntown Key West 3BDR/2BA Home

Conch Republic Cooler

Key West, Florida, United States

Bed

Bath

Sleeps

$309.57

This delightful retreat is a free standing newly renovated cottage with lovely private deck, front porch, and a dedicated private off-street parking space.brbrIt's perfectly located in the heart of Old Town. We are right next to the Truman Annex neighborhood and only two blocks from the world famous Duval Street. No other location on the Key can deliver you this close to shopping, fine art galleries, nightlife, restaurants, historical sites, beaches, and the “Duval Crawl”.brbrbrTHE SPACEbrThe cottage offers a modern island décor with hand-selected artwork and furnishings that create an curated aesthetic. Perfect for a weekend getaway or long season stays. The unit is perfect for couples or families that want to experience everything Key West has to offer!brbrOur lush retreat is equipped with a fully equipped kitchen with new appliances and dishwasher, full size washer & dryer, private bedroom with queen bed and spacious closet, restroom with tub/shower, and an open floor layout for dinning/living spaces. It also features a sofa bed (queen) in the living room, a dinning table set for 4, and 2 Smart TVs 60 & 50 (bring your UN/PW for Netflix, Amazon or other platforms you enjoy). A foldable work desk is thoughtfully placed in the bedroom, providing a designated space for remote work or planning your day's activities.brbrOutside, the cottage offers a private front porch where you can enjoy a morning coffee and watch island life pass by. For those looking to kick back and relax, the renovated outdoor private deck is surrounded by tall tropical trees and equipped with cozy lounge chairs. The deck is equip with string lights for lovely exterior evenings with your love ones.brbrEnjoy Island life in this hidden gem that combines the comforts of home with the conveniences of a vacation rental, ensuring you have a restful and enjoyable stay during your Key West escape.brbrbrLOCATIONbrWhether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located cottage.brbr15 minutes car ride from the airport.brbr4 to 8-minute walk to the best historic sights Key West has to offer such as the Truman Little White House Museum, Truman Waterfront Park, Mallory Square, the Ernest Hemingway Home and Museum and the Key West Lighthouse.brbr8-minute walk to Fort Zachary Taylor Historic State Park and its crystal clear and white sand beach area. The Clarence S. Higgs Memorial Beach is also reachable by an easy 8-min bike ride.brbrAround the corner from the city's renown culinary expressions as Blue Heaven, Rams Head Southernmost, and Moondog Cafe.brbrWe suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight.brbrbrGUEST ACCESSbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrOTHER THINGS TO NOTEbrOur cottage is one of four resident cottages in a gated unit complex. You'll likely meet our neighbors. Feel free to say Hi! We ask our guests to please keep in mind this is a residential community with full-time residents. Be respectful avoiding high levels of noise throughout day and night hours, and please park your vehicle in the assigned spot.brbrThis is a private property with no shared facilities/common areas with our neighbors.brNo smoking on any part of the premises and no pets allowed.brbrGuests have access to a 24/7 support team.brbrOur housekeeper, Crystal, cleans and disinfects all surfaces in the bedroom and bath according to Vrbo and Center for Disease Control guidelines.

Tropical Cottage

Key West, Florida, United States

Bed

Bath

Sleeps

$2640.94

Welcome to the Pagitt House built in 1933 and interior completely restored and upgraded in 2025! Located on Elizabeth Street just steps to all the Key West Historic Seaport and Key West hot spots! brbrAs you walk thru the white picket fence up the stairs to the Pagitt House you will see the covered and shady front porch that invites you to relax and enjoy the sights and sounds of Key West. It is a perfect place to people watch as they walk by. brbrWith a spacious floorplan spread amongst two floors and HUGE rear pool & entertainment area, this home is great for family and friends to come and relax and enjoy Key West in their own private sanctuary. brbrHOME DETAILS:brbr- 2100 Square Foot - Historical Home with Modern Interior Remodel! br- Small assigned parking - for compact car or golf cart only. SUV will not fit and no other assigned parking. brbrFloor 1: br- Living Room - with flat screen TVbr- Kitchen w/ Island Dining Room br- Primary Suite - King size bed with flat screen tvbr- Ensuite Bathroom - Shower & Tubbr- 2nd Primary Suite br- Ensuite Bathroom w/ shower br- Powder Roombr- Laundry Room brbrFloor 2:br- Bedroom 2 - Queen bed with flat screen TVbr- Bedroom 3- 2 Twin beds with flat screen TVbr- Bathroom 2- Full bath with shower in hallway for shared guest use brbrBack Deck - br- Large Pool Deck w/ Sun loungers with ample sunlight! br- 10 x 20' Pool - Heated in seasonal months 11/15-4/15 for additional charge inquire with management if you would like to heat. br- Covered Outdoor Sitting Area / Cabanabr- Washer & Dryer brbrWe hope to welcome you to Pagitt House during your next stay in beautiful Key West! brbrNOTE: THIS PROPERTY DOES HAVE A SMALL PARKING SPACE LOCATED IN THE ALLEY OF THE HOME. IT WILL ONLY FIT A SMALL COMPACT CAR OR SINGLE GOLF CART. ANYTHING LARGER WILL NOT FIT AND NEED TO PARK ALONG THE ROAD IN A UNASSIGNED SPACE WHICH CAN BE DIFFICULT TO FIND AND ANYTHING METERED IS EXPENSIVE. BEACUSE OF THIS WE DO NOT RECOMMEND BRINING ANY KIND OF VEHICLE TO THIS LOCATION.

PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!

Key West, Florida, United States

Bed

Bath

Sleeps

$358.88

Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.br brCastaway Cove offers all of the creature comforts you are used to at home including a full kitchen with cooking/dining essentials, Keurig & drip coffee machines and dishwasher. Meals can be enjoyed indoors on the peninsula countertop (up to 4) or outside on the private patio (up to 4). br brA Master Suite with ensuite bathroom, queen bedroom with bathroom attached (also accessible from living room) and a pull-out sofa in the living room can accommodate up to 6 guests for a restful night of sleep after a day of island exploration. Our guests also enjoy central AC, Free Wi-Fi, multiple smart TV's with cable and streaming capabilities, and in-unit washer and dryer.br brThe Sunrise Suites community offers our guests access to the following shared amenities:br-Heated Pool & Hot Tubbr-Sunbathing decks & loungers br-Fitness Center br-Tennis Courts br-Free parking on a first come, first serve basis (not assigned, not covered, proximity to unit not guaranteed)br-Walking Paths/Biking Trails br-Corner Store a quick 5 minute walk away

Castaway Cove: 2/2 Condo near the beach with shared pool and hot tub

Key West, Florida, United States

Bed

Bath

Sleeps

$1258.51

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThe moment you arrive at PALMS ON DUVAL, located a few steps from World Famous Duval Street in the heart of Key West, you will feel the laid-back island vibes take over as your vacation officially begins. Tucked away in an unbeatable Old Town location on a dead-end street, this charming three-bedroom, three-bathroom, one-story home offers the perfect blend of energy and escape.brbrStepping inside, you will be welcomed by a bright, inviting interior designed for relaxation, complete with comfortable bedrooms, a fully equipped kitchen, and a serene private pool area waiting just beyond the back doors. Best of all, you are mere steps from the shops, restaurants, and nightlife of Duval Street, yet comfortably removed in your own private oasis. Your stay also includes Last Key Realty’s Five Star Guest Services & Complimentary Concierge, known for creating truly memorable Key West vacations.brbrTHE LOCATION...brbrLocated less than 20 steps off of Duval Street (we counted!), PALMS ON DUVAL is an Old Town dream: you’re practically on Duval St, just a few blocks from the Southernmost Point, Fort Zachary Taylor State Park, or any other Old Town attraction you may want to explore. You'll be a short walk or bike ride to all that Old Town Key West has to offer. The best part is you’re on the “quiet” end of Duval St, which means you can easily head down to the fun, but you don’t have to worry about it keeping you up at night. While you won’t need a vehicle from this prime location, the private driveway serves as your off-street parking space in case you decide to rent a car or golf cart.brbrTHE LIVING AREA & KITCHEN…brbrAt PALMS ON DUVAL, the comfortable living area invites you to settle in and stay awhile, featuring a large flat screen TV, plush seating, and sliding glass doors that glide open to the covered lanai and tranquil private pool area. Natural light pours in, creating an airy, relaxed atmosphere that makes it easy to unwind after a day in the sun. The living area also includes a queen-size sleeper sofa, perfectly suited for any guests who might pop by and decide to extend their stay.brThe fully equipped kitchen offers all the comforts of home. Whether you are preparing a quick breakfast before heading out or crafting a full evening meal, you will have room to spread out and enjoy the process. There is seating at the stylish kitchen island for casual bites and conversation, or you can step outside to the beautiful covered lanai where a large dining table awaits, ready for relaxed dinners and lingering conversations in the open air.brTHE POOL...brbrStep through the back doors into your fully fenced private backyard oasis, complete with a dip pool that can be heated on request. Lounge in the chaises situated poolside and let the sunshine do its work. After a salty beach day or a refreshing swim, rinse off in the convenient outdoor shower. The spacious yard also features a large propane BBQ grill, perfectly poised for grilling up the day’s fresh catch.brbrTHE ACCOMMODATIONS...brbrAll three bedrooms in this lovely home are 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.brbr** Second Bedroom: King bed, flat screen TV, and en suite bathroom with a walk-in shower.brbr** Third Bedroom: King bed, flat screen TV, and en suite bathroom with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central A/Cbr** Ceiling Fansbr** Flat Screen 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 & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Lushly Landscaped Private Yardbr** Private Pool with Available Pool Heatbr** Outdoor Showerbr** Propane BBQ Grillbr** Off-Street Parking for 1 VehiclebrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** No Pets Allowed br** 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.

**PALMS ON DUVAL @ OLD TOWN** Private Home w/ Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$572.95

Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 baths and private patio with tropical views. Amenities include: Central AC, Dishwasher, Washer/Dryer, Color Cable TV, VCR, CD Player, Ceiling Fans, Sleeper Sofa, Community Pool, Sleeper Sofa, Full Kitchen, brbrThis and all of my places rent only Saturday to Saturday in the winter months.br br

Truman Annex unit 254

Key West, Florida, United States

Bed

Bath

Sleeps

$481.04

On the entire island of Key West there are fewer than 50 private homes on open water and only a few with their own private dock. Enjoy kayaking the crystal clear waters or relax in the private heated pool during the day, watch the sunset from the new dock and then enjoy the fine restaurants and Key West nightlife. Our renovated Gulf front, Key West home is nestled in a quiet, gated, private community in a secluded from the hustle and bustle. Enjoy the nightlife, fabulous restaurants, diving, fishing, parasailing and countless other activities which Key West offers and then, upon passing through the gate, return to your private retreat. Guest parking and a private, covered parking space is provided.br The home has a fully equipped kitchen with granite counter tops, stainless steel double sink, smooth top stove, new stainless french door refrigerator and new stainless dishwasher. Enjoy your coffee and breakfast on the back porch with breathtaking views of the crystal clear water. The large living area has gorgeous newly finished wood floors with two leather couches and big screen TV where you can relax, watch a movie or the game and still enjoy tropical views. The dining table is large enough to comfortably seat 6 for dinner if you choose to relax at home.br This wonderful home has 3 bedrooms and 2 1/2 baths spread out over 2 floors. The master bedroom and master bath are located on the second floor with its own private balcony overlooking the pool and spectacular open water. The master bedroom has a King size bed with new mattress, 2 closets and a flat screen TV. New wood look tile is throughout the upstairs with porcelain tile in the bathrooms. A second large bedroom is upstairs with a queen size bed, two closets and bathroom.br The downstairs bedroom has a full size bed and a half bathroom nearby. The utility closet downstairs has new full size washer and dryer. br Open the sliders and step out onto the new shaded deck and enjoy spectacular Gulf views, sunbathe with your favorite cocktail or take a dip in the private heated pool. Tropical landscaping, wireless internet, A/C, cable TV and a fully equipped kitchen will make you want to make this your home away from home. This hidden gem is an ideal private getaway from the noise but yet close enough to enjoy the night life. Kayak the crystal clear water, bring your boat or rent one from the nearby marinas or have your charter guide pick you up at the dock. Rent bikes, scooters or a golf cart and take a leisurely ride to Duval Street, Old Town, the renowned restaurants, lively bars, beaches, marinas, historic landmarks and shopping. brSmall pets considered with pet fee. Power boats ' with dock fee.br

Key West GULF FRONT Home with Private Dock and Heated Pool.

Key West, Florida, United States

Bed

Bath

Sleeps

$325.54

WHERE LIFE IS PURE…brThis dreamy 3 bedroom, 2 bathroom island getaway is sure to captivate the true essence of Key West charm within its tranquil setting. Peacefully located with convenience to everything, this home truly has it all making your Key West love story one never to forget! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brPull up to the first floor of this island beauty showcasing lush, vibrant foliage surrounding this quaint abode. Step onto a private front porch, perfect for a morning cup of coffee as you daydream of your island adventures. Slip inside to a bright and cheery living space with natural lighting inviting you in. Whip up your meals in a fully equipped kitchen with stainless steel appliances which can be enjoyed at the table for 4. Cozy living room furnishings surround a flat screen TV, perfect for movie and game nights. brbrSLEEPING ARRANGEMENTS…brTotaling 3 bedrooms, this home is perfect for bringing all your loved ones together in Paradise. A queen guest room with a TV and a full guest room both share a bathroom with a shower. The queen primary suite comes with a TV and an en suite bathroom with a shower. brbrOUTDOOR LIVING…brYour tropical fantasies will come alive outside in the lush backyard area with delightful foliage surrounding an outdoor shower and private pool that comes heated in the winter months. The pool is NOT shared with the guests upstairs. Grill up your fresh catch of the day to be enjoyed at the outdoor dining table. This home is just a short stroll or bike ride from Duval St., Historic Seaport and the beautiful beaches of Key West! brbrPARKING...brOff street parking for 2-3 vehicles is available making coming and going a breeze! brbrPETS...brSmall dogs are considered at this home on a case by case basis. A pet fee is required.brbrMULTI MONTH RESERVATIONS...brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay clean brPool/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). brbrLIVE LIKE A LOCAL…

THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Condo Centrally Located w/ Pool!

Key West, Florida, United States

3

Bed

Bath

6

Sleeps

$1047.32

Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom, a full kitchen with everything needed for on board meal prep, spacious living areas down below and above on the decks. The boat is in great condition and has been well maintained inside and out. Purpus is docked in a first class marina with access to free parking, restaurants, bars, ship store, pools, ice cream shop and laundry. Charter options available for additional fee.brbrLuxury sailing catamaran Purpus is as comfortable as she is seaworthy. This Bali 4.1 is an ideal build. The yacht has a spacious indoor/outdoor salon, sized for the entire party to be together. For sun and fun, a spacious cushioned bow lounge lets everyone enjoy an exciting view of the water. brbrPurpus is designed for water sports fun. Aft on both hulls steps lead directly into the sea, which makes getting on and off the yacht a breeze. brbrSailing catamaran Purpus has an ideal layout and is meticulously maintained. Purpus is available for family style charters and retreats for friends.

House Boat

Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$409.92

MINIMUM STAY 29 DAYS/28 NIGHTS Welcome to Conch Republic and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My oversized two bedroom, one bathroom condominium or casita as Cubans would call it, is located on picturesque Southard Street, the main entrance to the best location on the island, the Truman Annex where you can walk to just about everything you want to see or do. I am confident you would like this vacation home away from home. It is impeccably designed, meticulously maintained and you are surrounded with restful colors on the wall and art work from my many visits to Cuba on educational and humanitarian trips. I have everything you need for a worry free island vacation. Top mattresses, high thread linens, thirsty bath towels, large deep beach towels, high speed WIFI, reserved and secure parking and cable TV. Your comfort is my first priority and between my home itself and the large back deck shaded with a large umbrella, you can rest assured that you will enjoy your stay. The furniture and beds are very comfortable. The kitchen fully equipped from the Bosch dishwasher to the exotic micro wave and the Keurig coffee maker. Need a hair dryer Got it. Iron In above the large front loading washer and dryer. Beach chairs On the large back deck. Ask me about other amenities. And yes, there is the mandatory blender. This is my personal home so I would like to deal with you directly on email and telephone before we make a booking. Guests must come and go on a Saturday for the most part. Now on to more detail. Oh one more thing. If your party is looking for additional space, check out my cottage five doors down which is # 361238 here on VRBO. BONUS OFFER I HAVE SOME NICE OPENINGS IN SUMMER AND FALL A ALLOW ME TO OFFER A GIFT CERTIFICATE TO ONE OF KEY WEST'S BEST RESTAURANT BLUE HEAVEN

A Touch Of Cuba In Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$634.6

Introducing Glimmer Glass, an oceanfront two bedroom, two bath condominium at the Key West Beach Club, the premier Key West oceanfront development! Decorated with the cool tones of the ocean that laps outside, light glimmers off the water into the space. brbrThis third floor fully air conditioned home has a spacious living / dining area that offers abundant space to entertain or simply relax. A large screen tv surrounded by comfortable seating allows for that streaming movie night or your favorite sporting event. A Sonos sound system provides surround sound for your movie or simply to stream your favorite music. Expansive sliding glass doors open directly to a large balcony with two sitting areas and teak table for outdoor dining (up to 6 people) overlooking the beach and ocean. Sun streams into the balcony each morning, transitioning to the glow of sunset off to the west in the evening. brbrThe large cook’s kitchen with newer appliances, including a Viking refrigerator with an ice maker, is ready to prepare meals to entertain friends and family. The range has a double oven for the ease of baking. A water filtration system has been installed on the kitchen sink, so pack your water bottles and skip the case of water at the grocery store. The coffee station features both a regular drip coffee maker and a Keurig so the options are covered. A stacking washer/dryer unit is also in the kitchen area, so you can pack less brbrThe two oversized bedrooms with king size beds (or one with two twins) features luxury cotton bedding. The main bedroom has a contemporary tropical feel with a king woven sleigh bed set against the backdrop of teal grasscloth. Sliding doors access the balcony to go straight from waking up to watching sunrise! A large walk-in closet will allow you to unpack for your vacation stay. The principal bathroom has a large walk-in shower of beautiful blue tiles with plantation shutters that can be opened to enjoy the ocean view while showering. The second bedroom is large with either a king bed or two (extra long) twins, backing up to a woven leather headboard wall. A built-in wall of shelves also provides a desk area for the working vacation. The hall door closes off to make the second bathroom ensuite or it serves as the general powder room for the common area. The second bath also has a comfortable walk-in shower.brbrThe breezeway entry can be utilized as an office for 1 or 2 people at the same time. French doors can close this off from the kitchen if privacy is needed for that work call or zoom that can be avoided on vacation.brbrThe Key West Beach Club complex provides a resort-like atmosphere complete with 2 heated swimming pools, jacuzzi, workout room, outdoor barbecues, dedicated covered parking, elevator and a tennis court! All securely inside a gated entrance with beautiful landscaping. Due to the tide schedules, the beach may disappear during normal beach hours. This is not a beach that people normally lay out on.brbrThere are very few direct ocean front residences in Key West with direct beach and ocean front access. Listen to the ocean waves lapping on the beach just steps away. Glimmer Glass has this and more! brbrReady for a night out Glimmer Glass is a short walk to Salute restaurant on the Beach and the features of the Casa Marina Resort or 10 minute bike ride from all the activities, attractions and excitement of Duval Street. Still close enough, but far enough away to enjoy the “getaway from it all” feeling! brbrStay for a week or two or a month or two! This home is a perfect retreat to feel the ocean breezes and soak in the beauty of the Key’s ocean literally feet from your balcony!

Glimmer Glass oceanfront condo by Rent Key West Hideaways

Key West, Florida, United States

Bed

Bath

4

Sleeps

$299.75

Charming Canalfront 3-Bedroom Home with Office, Dock, Kayaks & Park Access – Just 13 Miles from Key West!brEscape to the Florida Keys in this beautifully landscaped, ground-level 3-bedroom, 2-bath vacation home, ideally located just 13 miles from Key West. Nestled along a serene canal, this spacious and comfortable retreat is perfect for families, boaters, remote workers, and outdoor enthusiasts.brInside, you'll find a dedicated office and a bonus air-conditioned storage room, offering flexibility for longer stays or working remotely. The master suite features a king-size bed and direct access to the backyard—enjoy your morning coffee overlooking the emerald green canal right from your bedroom.brThe guest bedrooms include one with a queen bed and another with a twin and full bed, accommodating a variety of sleeping arrangements. Each bedroom has its own mini-split AC and heat unit for personalized climate control.brThe dining area features a beautiful wood table with seating for six, and the living room includes a Samsung Smart TV, ready for you to log into your favorite streaming platforms. There is a Bonavita Drip coffee maker at this home for you to enjoy your favorite brew.brOut back, enjoy a large yard, a refreshing outdoor shower, and a shed stocked with 2 kayaks, a canoe, and 2 bikes for guest use. The wood dock comfortably accommodates boats up to 20' with a 3' controlled draft—perfect for fishing or easy access to open water.brJust a short walk away, you'll find a community park with great amenities including pickleball and tennis courts, volleyball, basketball, bocce ball, a playground, and a large open field for games and gatherings.brYou're also less than a 5-minute drive to South of the Seven, a fantastic local restaurant loved by visitors and locals alike. And for your morning caffeine fix or an afternoon pick-me-up, take a quick stroll to the infamous Baby's Coffee—home of the southernmost coffee roasters in the U.S.brThis pet-friendly home welcomes one hypoallergenic dog under 25 pounds with prior approval and a non-refundable pet fee of $250. Maximum occupancy is 6 guests. Parking is available for up to 2 vehicles, plus space for a boat trailer. There's also a bait freezer in the laundry room for anglers, plus high-speed Wi-Fi and all the comforts of home. Whether you're kayaking through mangroves, exploring Key West, biking to nearby spots, or playing pickleball at the park, this canalfront gem offers the perfect blend of relaxation and recreation in the Florida Keys.brbrThis is a 28-night minimum rental per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. ***The renter will be asked to send a photo of their drivers license upon booking. There is a 4% credit card processing fee. All reservations subject to final approval from the local Rental Manager. Online bookings accepted with approval from the Rental Manager within 24 hours. The vacation rental contract must be signed and returned after speaking with the Rental Manager for the reservation to be confirmed. brTo ensure that you are protected, as well as the owner, we require a $55 Damage Waiver Insurance Policy.

Charming 3BR canal home close to Key West with kayaks, bikes and park access.

Key West, Florida, United States

3

Bed