Vacation Home Rentals By Owner In Key West, FL

SPOIL YOURSELF…brCome unwind in this tropical retreat allowing for your delightful Key West story to unfold. Sounds of swaying palm trees beneath sunny skies will draw you into this picturesque dream you’ve been craving for within this quaint Old Town sanctuary. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENTITIES…brStep onto a lovely front porch pulling you out of reality and into island time washing all your worries away. Inside you will be greeted with cheery surroundings and cool wood flooring within this cozy space bringing the everyone together. An updated kitchen featuring stainless steel appliances and granite counters graciously opens up to a living room equipped with comfortable furnishings and a flat screen TV. Enjoy bar seating for 4 or take your treats outside to dine together welcomed by a sweet tropical breeze. brbrSLEEPING ARRANGEMENTS…brFind a spacious queen bedroom equipped with a flat screen TV and a bathroom with a shower/tub combination that also opens up to the hallway for convenience. Perched above this room is a loft with a queen bed. Beyond the outdoor living space lies a roomy 1-bedroom cottage with a flat screen TV, full kitchen, en suite bathroom with a shower/tub combination and a queen bed. Enjoy a queen sofa sleeper in the cottage for additional visiting guests. brbrOUTOOR LIVING…brCome unwind in this desirable outdoor space offering a wonderful place to lounge and enjoy the simple treasures of island life. Grill up your fresh catch of the day and sip on your cocktail beneath the stars. Enjoy an outdoor shower to wash the day away. This home is just a short bike ride to all the beloved Key West attractions. brbrPARKING...brThis home allows parking for one vehicle.brbrPETS...brPets are considered up to 30 pounds and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrCOME AND STAY A WHILE…

GOOD FEELIN ~ Charming 2 BR/2 Ba Home Conveniently Located w/ Parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$207.35

LOST ON ISLAND TIME…brTreasure your time together within this charming Key West cottage tucked away on this peaceful and vibrant lane in the iconic Old Town district. As you step inside a lifetime of memories are created as your loved ones come together for a unique and blissful getaway. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brShowcasing a nautical lifestyle with modern amenities, this retreat allows you to truly live in the present. Enjoy a front porch boasting island views at every corner as you wave hello to friendly neighbors passing by. Within the home you will find an updated and fully equipped kitchen with stainless steel appliances and granite counters. Enjoy bar seating for 3 or take your treats outside and dine al fresco in the welcoming breeze. The adjacent living area is complete with cozy furnishings and a flat screen TV for movie nights. brbrSLEEPING ARRANGEMENTS…brFind a king bedroom with a flat screen TV located at the front of the home which can also be accessed from the front porch. Steps away is another guestroom outfitted with a queen bed and a flat screen TV. A full bathroom with a glass shower resides just outside both guestrooms. brbrOUTDOOR LIVING…brIndulge in island time within this lush and vibrant outdoor setting beckoning you in for more. Unwind with a good book on the plush outdoor furniture and stroll around by foot in this peaceful neighborhood. brbrPARKING...brThis home allows parking for one vehicle.brbrPETS...brPets up to 30 pounds are considered and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). brbrTIME TO LIVE IN THE PRESENT…

POSITIVE VIBES ~ Charming 2 BR, 1 Ba Cottage in Peaceful Area w/ Parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$617.63

This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroom downstairs has a queen bed and also has it's own bathroom. There is a queen sleeper sofa with a screen divider for privacy if needed. Pool is just across the way in the center of the complex. Propane grill on back porch. Has a Kuerig and a regular coffee pot. brClose to the Golf Course and marina and public boat ramp - 2 miles from beaches.br

Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach

Key West, Florida, United States

Bed

Bath

Sleeps

$161.41

Summary:brbrOld Florida canalfront getaway close to Key WestbrbrbrbrThe Space:brbrEscape to this Old Florida-style cottage offering a quintessential retreat for fishing enthusiasts and nature lovers alike. Located just a short distance from the vibrant energy of Key West, this charming monthly rental promises tranquility and adventure in equal measure.brbrbrbrBoasting 100 feet of concrete dockage, complete with electric and water hookups, as well as a convenient fish cleaning station, this cottage is a haven for anglers seeking the thrill of the catch. An added bonus is the presence of a 600-pound ice machine and bait and fish freezers, ensuring that every fishing expedition is well-equipped and memorable. It's worth noting that this rental is best suited for shallow draft boats, as the canal entrance has approximately 2 feet of depth.brbrbrbrStep inside to discover a cozy interior with rustic charm. The quaint kitchen is equipped with the essentials but no dishwasher. This cottage features two bedrooms, each furnished with a comfortable queen bed, providing a peaceful sanctuary for rest and relaxation after a day of exploring the waters. Window air conditioners ensure a comfortable indoor climate, while ceiling fans circulate the refreshing sea air.brbrbrbrWhether you spend your days casting lines off the dock, exploring nearby Key West attractions, or simply unwinding in the peace and quiet of Baypoint, this monthly vacation rental offers a perfect blend of serenity and adventure for your coastal getaway. Experience the laid-back charm of the Florida Keys from this idyllic waterfront retreat.brbrbrbrThe primary guest must sign a rental agreement. This is a 28-day minimum rental per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 4 people. All guests need to be registered with the property manager. No smoking. Up to 2 pets permitted with manager approval and $250 nonrefundable per-pet fee. There's a cap on electric ($250) and water/sewer ($150) .

Fish Camp | Old Florida canalfront getaway

Key West, Florida, United States

Bed

Bath

Sleeps

$617.63

br br This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroom downstairs has two twin beds which could be converted into a king upon request and also has it's own bathroom. There is a queen sleeper sofa with a screen divider for privacy if needed. Pool is just across the way in the center of the complex. Propane grill on back porch. Has a Kuerig and a regular coffee pot. brClose to the Golf Course and marina and public boat ramp - 2 miles from beaches.br

Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach

Key West, Florida, United States

Bed

Bath

Sleeps

$481.02

Tropical 2 bedroom, 2.5 bathroom, 2 level Key West townhome to be your home away from home! No detail has been overlooked in this comfortably decorated vacation rental. Located in one of the islands newest gated community’s, Coral Hammock, you are close to all that Key West has to offer. If you’re looking to kick back and relax in a homey atmosphere, Casa Caribe is the place for you! brbrOn the first floor, the kitchen is vibrant with fresh white cabinetry. Full kitchen appliances allow for either complete at home dining or even for quick and easy meals. Ceramic tiles cover the first level, giving you a classic Key West look. There is also a powder room on the main floor for convenience. brbrInterior walls throughout the house have been painted with soft and fun, tropical colors which ties in a true island ambiance. The deck extending from the living area is complete with comfortable wicker style furniture, which serves as the perfect spot to relax and enjoy the deck’s amazing view of the pool and lush landscaping of the complex. brbrThe second floor leads to the two main, airy bed and bathrooms. There are dual masters on either side of the home, separated by an in house laundry with a new washer and dryer, keeping you fresh and lightly packed while on vacation. Both masters have spacious bathrooms, which are tastefully decorated with bright accessories, mirrors and lush textiles. The first master bedroom is a retreat for your soul with a king size bed. Two large windows on adjacent walls along with a full size glass door leading to the second floor deck (also overlooking the pool) illuminate the room with Key West’s happy, natural sunlight. The second bedroom, queen size bed clothed with 600 thread count linens. Two large windows above the bed frames allow for a bright and refreshing space.brThe carpets have been replaced with wood flooring in bedrooms, hall and stairs.brThis home is fully stocked and ready to go for your convenience. Pack a few swimsuits and leave your worries at home, we have you covered with all of the amenities you need for your home away from home.brbrLiving Room:brTV with free cable and WiFi Internet accessbrDark blue sleeper sofa and love seat, perfect for lounging with your favorite bookbrWarm, tropical décor setting the mood for island lifebrbrKitchen:brBright and fresh cabinets and counter topsbrFull kitchen appliances including stove, microwave, refrigerator, and dishwasherbrFully stocked with flat ware, dinner ware, cups, mugs, utensils, pots and pansbrCoffee Pot brBlender (perfect for morning smoothies and evening margaritas!) brBasic necessities for your meal prep including spices, condiments, etcbrbrDining Room:br6-chair dining room tablebr2 stools set at the breakfast bar off the kitchenbrbrMaster Bedroom:brKing size bedbrPillow top mattressbr600 Thread count linensbrNight standsbrClosetbrPrivate bath stocked with fresh linensbrTV with cablebrbrSecond bedroom:brQueen bedbr600 Thread count linensbrNight standbrClosetbrPrivate bath stocked with fresh linensbrTV with cablebrbr1st Floor Porch:brTropical outdoor patio setbrbrGarage/ground level:brCovered parking for 1 carbrStreet parking for additional vehiclesbrBBQ area just steps away from the poolbrbrbrCommunity Features:brLarge heated pool with lounge chairsbrClubroom available for large parties (with a small fee)brFully equipped fitness centerbrLush tropical landscaped grounds perfect for evening walksbrGated community brbrSurrounding amenities:brCasa Coral is just north of the island, about 4 miles from famous Duval Street. This puts you just far enough away from the infamous Key West nightlife that you can enjoy an evening out, and come home to your relaxing and quite tropical get away. brbrFor your daytime adventures, the community sits directly across the street from the islands only public golf course, is on the next block up from a public boat ramp, is lined by a bike path to take you around the whole island, and is next to some of the best local dining where you can enjoy fresh seafood, Cuban cuisine and more!brbrJump on a bike and ride along South Roosevelt Blvd to enjoy the spectacular views along Smathers Beach, or take your car for a ride along North Roosevelt where all the islands shopping is just minutes away. Close to several water activities including jet ski rentals, catamaran adventures, glass bottom boat tours, historic old town Key West tours, and so much more.brbrCasa Caribe is owned and rented by Key West natives, who grew up and have now raised their family on the island. They are the perfect couple to give you advise on the best of the local spots for dining, dancing, shopping, sight seeing and activities! This townhome retreat is truly your ideal vacation package, and we can’t wait to welcome you!br

Casa Caribe Beautiful tropical 2 bedroom sleeps 6

Key West, Florida, United States

Bed

Bath

Sleeps

$324.83

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: Located in the heart of Old Town Key West on a teeny tiny quiet lane, this two-story home with a first-floor bedroom is ideal for the entire family. Elders will enjoy the convenience of single-story living in the four-poster queen bedroom with hall bath, armoire storage and a window seat overlooking Curry Lane. You can enjoy the second floor’s primary king bedroom with large closet, as well as the spacious ensuite bath with dual sinks, walk in shower and claw foot tub. Your guests or young adults may enjoy the privacy of their own pool house with an ensuite half bath and delightful outdoor shower. brbrThe first floor is also where you will find the spacious family room adorned with hardwood floors and rattan, Bahamian, and British Colonial style furniture. An updated kitchen with granite countertops and stainless-steel appliances includes everything you need to prepare meals or snacks. Adjacent to the kitchen is the dining area with seating for six. Two large sets of French doors in the family room provide access to the outdoors and pool area. Here you will find a seasonally heated pool, lounge chairs, a gas grill, and an outdoor dining table under a covered loggia. Access to the outdoor shower and half bath in the pool house is also found here. Surrounded by palm trees, a large mango tree, and lush landscaping, you will find peace and serenity in this spacious island home in paradise. brbrBED CONFIGURATION: The first floor has a queen bedroom with hall bath. The second floor has a king primary ensuite with additional daybed. The pool house has a queen bed and an ensuite half bath with attached outdoor shower. brbrOUTDOOR AMENITIES: Lush landscaping surrounds the amazing pool. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Dine outdoors under the covered loggia with table, chairs, and a large mango tree! A gas grill and lounge chairs are also provided for your enjoyment. brbrPARKING: There is one parking space for a small car which is a real perk in Key West. Additional parking may be found on neighboring side streets. Please note this home is on a small lane. brbrLOCATION: Old Town, North of Truman Avenue and near The Meadows neighborhood. Numerous tourist attractions are located here as well as several restaurants and shops. The area boasts historic and conch style homes and is 4 blocks from the Historic Seaport District and Art Gallery District on White Street.brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Guests must be 25 years of age or older unless accompanied by an adult. brbr***Managed by Historic Key West Vacation Rentals***

~ VILLA AZUL ~ Enjoy this historic home with pool house and parking.

Key West, Florida, United States

Bed

Bath

Sleeps

$489.19

Behind the front privacy fence lies this beautifully renovated 3 BD/3.5 BA home. Complete with a tropical private pool sanctuary. Owners have lovingly thought of every detail including 6 bikes and a GEM electric car (details on GEM car below). The front porch welcomes you with wide glass slider doors to an indoor/outdoor cozy living/kitchen area with everything needed. There is an option to grill/eat out side porch. Living rm has a smart TV equipped for personal streaming. Home is centrally located and walkable to beach & Duvall str.brbrQuiet, Casa Marina area. We are 2-3 blocks from Higgs beach as well as the famous Louie`s Backyard RestaurantbrbrADDED BONUSbrGEM electric car 4-seater with trunk to get everywhere on the island. Ask host for options to include this in your booking.brbr** Pictures are always being updated @visitsouthofreality over on IG

Casa Marina Cottage+ private pool+walk to Duvall st.

Key West, Florida, United States

Bed

Bath

Sleeps

$859.44

Summary:brbrFamily-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else that Old Town Key West has to offer.brbrbrbrStep out on the deck of The Mesa House and breathe in the ocean breeze! This well-furnished home provides plenty of space to relax, ideal for families or groups. You're within walking distance of the docks, as well as the nightlife of Duval and the Key West Seaport. Stop by Cuban Coffee Queen for a cafécito or the seaport for water adventures!brbrbrbrThe Space:brbrThe Mesa House is made up of two condos that can be rented separately for smaller groups. Up to 10 guests can stay here in three bedrooms. Two full kitchens make meals easy for everyone.brbrbrbrCentral air conditioning keeps everybody comfortable. Four cable TVs and free WiFi are provided.brbrbrbrMesa House UnobrbrBedroom 1: KingbrbrExtra Sleeping: queen pullout couch in the living areabrbrbrbrMesa House DosbrbrBedroom 1: King brbrBedroom 2: Two TwinsbrbrExtra Sleeping: queen pullout couch in living area brbrbrbrBook The Mesa House for your group's next Key West vacation!brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrThis home is located in the heart of Key West's action, with plenty of dining and entertainment within walking distance, including historic Duval Street. Stroll a few blocks north to the docks, where snorkeling, boating, and other aquatic adventures await you.brbrbrbrHalf a block from Duval Street, The Mesa House, is steps away from Key Wests most famous bars and kitchens. Local’s favorite restaurants, such as First Flight, Bagatelle and Two Friend’s patio are less than a 5 minute walk from your front door. Got a sweet tooth Keep an eye out for Kermit’s Key Lime Pie Shop in the Historic Seaport known for the best Key Lime Pie in Key West, or grab some homemade fudge and candy from River Street Sweets.brbrbrbrForgot something or need a quick fix Shorty’s Market has your last minute necessities for your weekend getaway. Just 2 blocks away you can also find Fausto’s food market for locally sourced groceries.brbrbrbrGetting Around:brbrOne of the best parts of staying in Key West is how close in proximity you are to everything, this small little 2x4 island offers a variety of ways to get to and from your destination! Don’t feel like walking Peddle your way to breakfast, or take a bike ride along the water at sunset, by renting from Fury or Island Bicycles who offer both pick up & drop off of bike services! Feel like you’re on island time when you rent from Minty’s where you can enjoy exploring Key West on a scooter or golf cart! In addition to these non-traditional modes of transportation, you can also Uber, Lyft or Taxi to your next destination. Pink Taxi is an easy, reliable and affordable way for getting to your rental from the airport. brbrbrbrUnfortunately, there is no on-site parking for this unit. brbrFor overnight parking here are some parking lots:brbr• 204 Simonton Street (This is directly next to your unit and the most affordable on the island!)brbr• Caroline Street Outdoor Parking Lotbrbr• Park N Ride Old Town Garagebrbr• Fleming Street Overnight Pay to Park lotbrbrStreet parking information:brbr• There are pay-to-park spots and meters and it is free from 12AM - 8AM. With a 3 day limit.brbr• The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only” and visitors are NOT permitted to park in them.brbrbrbrOther Things to Note:brbrThere is no parking provided for this unit. However there is a pay-to-park overnight lot located directly next to your unit.brbrNo pets or smoking allowed.brbrPrivate washer and dryer

The Mesa House - One block from Duval St

Key West, Florida, United States

Bed

Bath

10

Sleeps

$252.7

**NEW PHOTOS COMING SOON!**br**NEW LISTING**brbrBRING YOUR SANDY FEET AND FLIP FLOPS ...brDive into ultimate island nirvana in this delightful cottage, just right for one or two couples, seeking sweet refuge. The relaxed ambiance of this cozy nest is tucked into an ideal Old Town neighborhood, conveniently located 3 blocks from the quiet end of Duval, a short stroll to Higgs Beach, Southernmost Point, French bakeries and Cuban coffee!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE. THIS IS AN ADULTS ONLY PROPERTY.brThis is a non-smoking property - inside and out.brbrDETAILS AND AMENITIES...brSet back from the street behind a gray picket fence, enter the main house that invites you to drop your bags and sink into pleasing comforts. Savor morning cups of coffee or an evening beverage while you relax on the front porch and immerse yourself in the colors and serenity of the garden. Catch the soothing ocean breezes and fragrant blooming jasmine. Inside, you are greeted by the authentic charm and character of a true Key West abode, complete with Dade County Pine, original Hunter ceiling fans, and mahogany and tile floors. The kitchen is compact but efficient, fully equipped for cooking and baking, and opens to the living room. Enjoy a large desk with work space in the front room. brbrSLEEPING ARRANGEMENTS...brThere are two ground floor bedrooms - one queen bed in the front and one double bed in the back of the house. Both feature ensuite bathrooms with walk-in tile showers, granite-top vanities, and closets. The back bedroom is private and opens directly onto the deck and pool. There is also a treetop suite that is accessed via an outdoor stairway on the deck. It has a double bed with an ensuite bathroom, and can be used as a detached office or studio space. brThis home accommodates 4 people max. brbrOUTDOOR LIVING...brAmple outdoor living space makes this cozy home feel spacious and comfortable. The back deck is visible from inside the home through French doors so that - day or night - you feel connected to the tropical outdoor ambiance. Enjoy your breezy covered porch, overlooking a sparkling pool that is surrounded by lush and soothing greenery. Toss your fresh catch of the day on the BBQ grill and dine al fresco at the large outdoor dining table. brbrPARKING...brThere is not an off street parking space for this home, however curbside parking is always available near the front gate.brbrPETS...brThis is not a pet friendly home.brbrBOOKING DATES...brThis home is offered only 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.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrLOSE YOURSELF ON ISLAND TIME…

ZEN GARDEN RETREAT~NEW! Adult Only 2 BR with Treetop Suite/Writer Studio!

Key West, Florida, United States

Bed

Bath

Sleeps

$788.35

Escape to Your Key West ParadisebrbrWelcome to your home away from home in the heart of beautiful Key West. This spacious 3-bedroom, 3-bathroom retreat combines modern comfort with the laid-back charm of island life, offering the perfect backdrop for your unforgettable getaway.brbrRelax in StylebrStep into a bright and airy living space designed for comfort and relaxation. Sink into the cozy sofa bed or unwind in one of the three beautifully appointed bedrooms, featuring one luxurious king bed and two inviting queen beds. Each room is a sanctuary of calm, complete with plush linens and thoughtful details to make you feel right at home. The bathrooms are equipped with everything you need, from a rejuvenating shower to a relaxing soak in the tub.brbrYour Island OasisbrPrepare meals in a fully equipped kitchen or head out to discover Key West’s world-class dining scene. When you’re not exploring, enjoy the peaceful outdoor spaces that make this property truly special. Sip your morning coffee on the porch as you listen to the tropical breeze rustling the palms, or gather with loved ones in the comfortable living area after a day of adventure.brbrPerfect Location, Endless AdventuresbrThis charming home is just minutes from Key West’s most iconic attractions. Stroll down lively Duval Street, soak up the sunset at Mallory Square, or discover hidden treasures in the local boutiques and galleries. Ready for some ocean fun Snorkeling, sailing, and pristine beaches are all within easy reach.brbrYour Hosts, Your GuidesbrWe’re here to ensure your stay is as seamless and enjoyable as possible. Whether it’s recommending the best seafood spot in town or sharing a hidden local gem, we’re just a message away.brbrBook Your Escape TodaybrWhether you’re planning a family getaway, a romantic retreat, or a trip with friends, this Key West home has everything you need for the perfect stay. Don’t wait—your island paradise is ready to welcome you!

Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

Key West, Florida, United States

Bed

Bath

8

Sleeps

$607.31

Welcome to WINDWARD SOUTH — Your Peaceful Retreat in the Heart of Old Town Key WestbrbrDiscover the perfect blend of comfort, charm, and tropical elegance at Windward South, a beautifully appointed 2-bedroom, 2.5-bathroom home ideally situated in the highly sought-after Old Town Key West neighborhood. This inviting getaway places you just steps from iconic sites such as world-famous Duval Street, the Ernest Hemingway Home and Museum, art galleries, historic architecture, top-rated restaurants, lively pubs, and the vibrant energy that defines Key West.brbrA Warm and Inviting First FloorbrStep inside to a bright and thoughtfully designed main level that immediately welcomes you with warmth and style. The spacious living room provides plush, comfortable seating—perfect for enjoying mornings with coffee, unwinding after island adventures, or spending time together in the evenings. Two sets of French doors fill the space with natural light, creating a relaxing tropical ambiance.brbrAdjacent to the living room is a formal dining room, ideal for shared meals, puzzles, games, or relaxing gatherings. The fully equipped kitchen offers everything you need for effortless vacation cooking and also opens to the backyard through another set of beautiful French doors.brA cozy guest suite is located on this level, offering convenience and comfort for guests who prefer to avoid stairs. A stylish powder room adds convenience for everyone staying at or visiting the home.brPrimary Suite: A Luxurious Second-Floor SanctuarybrbrAscend the spiral staircase to discover a truly exceptional feature of Windward South: the entire second floor is dedicated to the expansive primary suite.brThis serene retreat offers complete privacy and comfort, making it an ideal sanctuary for rest and rejuvenation. The suite features a luxurious king-size bed, generous natural light, and sophisticated island-inspired décor. The spacious layout provides room to relax, refresh, and recharge in total comfort. A beautifully appointed en-suite full bathroom completes the space, offering both convenience and a sense of indulgence. This private level of the home makes the primary suite the perfect haven for couples or anyone seeking quiet relaxation during their stay.brbrOutdoor Living at Its FinestbrStep outside to your own private tropical oasis. The backyard features a lagoon-style swimming pool, ideal for cooling off during warm Key West afternoons. Seasonal pool heating ensures that you can enjoy soothing swims year-round.brComfortable outdoor seating invites you to lounge under the sun, enjoy morning coffee in the breeze, or gather for evening cocktails and conversation. A gas grill makes outdoor cooking easy and enjoyable, whether you're preparing fresh seafood or grilling a casual meal with family and friends.brbrComfort, Convenience & Everything You Need! Parking is simple and stress-free with space for two vehicles in the driveway and in front of the home—an invaluable perk in the heart of Old Town.brThe home stays cool and refreshing thanks to efficient air conditioning and heating, ensuring comfort in every season. Whether you're getting ready for the day or winding down after exploring the island, every space feels soothing, cozy, and thoughtfully designed.brbrYour Key West Escape Starts HerebrWindward South is more than a vacation rental—it’s a place to unwind, reconnect, and create unforgettable memories. With its ideal location, comfortable living spaces, serene outdoor oasis, and beautifully designed suites—including the private second-floor primary retreat—this home offers everything you need for a brilliant getaway.brbrWhether you're visiting for romance, relaxation, adventure, or celebration, Windward South is ready to welcome you with the comfort and charm that make Key West unforgettable.brbrMake your vacation one for the books with a stay at Windward South.

WINDWARD SOUTH- Delightful 2-bedroom house with Pool in Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$777.66

Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic Designer Octagon House of Key West, makes a grand architectural statement. Often featured in notable publications with photos of its famous octagon shape front porches, the main structure of the house is in fact rectangular in shape with a multi-sided front. But it is the captivating five-sided front that distinguishes it from the many other remarkable centurion Victorian homes of Key West. Truly a home of fine distinction, it also has an eminent restoration history that began in 1976. Most recently in 2018, it received a sensational interior design makeover that brought it to current 5-Star Quality Resort Amenities standards.brbrA LITTLE BIT OF HISTORY:brbrOften referred to as `The Calvin Klein House,` in truth the iconic Designer Octagon House of Key West was an avant-garde preservation project accomplished by designer superstar Angelo Donghia during 1976 – 1978. Because of Donghia`s stellar status in the design world, this single renovation project was transformative for Key West during the 1970`s when creatives were beginning to turn neglected wooden centurion relics into elegant homes.brbrThe recipient of many prestigious awards during his lifetime and posthumously, Angelo Donghia was one of America`s most influential interior and furniture designers during the mid 1960`s through the mid 1980`s, with a celebrity client list with the likes of Ralph Lauren, Neil Simon, Diana Ross, Liza Minnelli, and elite projects such as the Metropolitan Opera House in New York and Omni International Hotels in Miami. His time spent in Miami in the 1970`s peaked his interest in Key West where he could easily escape from the bustle of the city for respite on an island accepting of artistic individuality and alternative lifestyles. `It`s a cross between Nantucket and Papeete, in Tahiti. It`s not a prissy resort, like Nantucket, but there`s some of Nantucket`s old elegance mixed with Key West raunchiness.`brbr`I`m a free spirit and a gambler,` is how Donghia described himself in interview, and when he got to Key West in the 1970`s he was taken with the hundreds of historic wooden houses and craftsmen who were beginning to restore them. When he found the unique octagon house on Eaton Street, it had been standing for over 90 years. Originally built in 1885 by Richard Peacon, the island`s principle grocer at the time, it had fallen into serious decay during economic downturns. As one of his cousins shared with me, Donghia was somewhat reluctant to do the project because of the neglected state of house. But dreamer that he was, in 1976 he purchased it for $45,000, and spent two years restoring it. He turned it into a spectacular show piece putting his indelible signature on the southernmost city.brbrHis approach to the eccentric octagon house had a casual point of view that highlighted renovation and preservation, and the décor reflected his own classic minimalist design style that earned him the nickname the `man with the gray flannel sofa.` Using tailor`s suiting fabrics, such as canvas, silk, linen and flannel, he `dressed` the rooms much like a tailor. An often-published photo of the living room displays this famous style that would become permanently embraced in the interior design world – white bleached wooden walls and floors, sofa and chairs in simple white canvas coverings, rattan furniture set on a natural fiber rug. Donghia`s renovation project was impeccable to the point where the house sold in 1981 to Calvin Klein for nearly $1 million – 15 times the original purchase and a record price at the time. Today we owe thanks to Angelo Donghia for saving this iconic home while raising the bar on historic home renovation in Key West. brbrbrBedding Summary:brbrbrFirst Floor (Bedroom One) - 1 King size bedbrbrSecond Floor – (Bedroom Two) – 1 Queen size bedbrbrSecond Floor - (Bedroom Three) Master Bedroom – 1 King size bedbrbrSecond Floor – (Bedroom Four) - 1 Queen size bedbrbrbrAmenities: Impeccable renovation with extraordinary designer decor. Expansive exotic back yard resort-style gardens, large swimming pool, outdoor back porch living room, mature tropical landscaping, expansive octagon verandahs, privacy fences. Fully equipped luxury kitchen, central a/c, 43-inch flat screen TV in living room, a 43-inch TV in the master bedroom, and 70-inch TV in the poolside pagoda. Full-size front-loading washer / dryer is set on the covered back porch, tropical style, hidden by a curtain. Linens and towels are provided. Catering can be arranged. Maid service can be scheduled.brbrActivities:Heart of Key West`s designated Historic Seaport District. Walk to all old town features, no need for a car. Close to Duval St., close to Mallory Square Sunset Celebration,and a few short streets from Historic Seaport (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife. Conveniently located to Fausto`s Food Palace for gourmet grocery shopping with excellent wine selection, sushi deli, and butcher. Close to shopping, art galleries, and a wide variety of outstanding restaurants and coffee shops. Close to the beach.brbrArea:This estate home is situated on famous Eaton Street, just one block from the docks of the Key West Historic Seaport. This tiny district is where the founding fathers and mothers built the first shipping docks and warehouses, restaurants and grand homes, including this one. Today these homes stand as one of the largest and most impressive collection of turn-of-the-century architecture in the U.S.A. Today this district includes famous waterfront restaurants and bars, retail stores, museums, fishing and sailing charters, a large variety of historic homes.brbrParking:There is a bricked driveway to the left of the house as you face the front. There is room to park more than one car if you park end to end. Once you`re here, park your vehicles and enjoy walking or biking everywhere—you`ll see more that way.brbrRestrictions:30-day minimum stay. Ideal for families and groups to unite but is not suitable for staging loud parties. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. Smoke free house.No pets please.brbrNotes:This property is ideal for professionals, corporate groups, and executives who have discerning tastes looking for a spacious and luxurious accommodation.

Designer Octagon House of Key West - w Private Pool - Blocks off Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$707.39

Enjoy all of Key West's exciting activities from the privacy and comfort of your own two-story, historic home in Old Town, Key West. brbrHidden behind lush tropical foliage, this 4 Bedroom (three suites on ground level), 2 Bathroom (+ 2 half baths) masterpiece awaits your arrival. This upscale home has many features such as open living and dining areas, eat-in kitchen, high ceilings, and wrap-around porches which overlook the completely private and heated swimming pool. brbrTake a short bike ride through the streets of Old Town and arrive at Duval Street's amazing restaurants, bars, shopping and art galleries.brbrNote: This house will be listed For Sale on October 1, 2025.

Eliza's Secret - Elegant Tropical Oasis with Private Pool & Guest House

Key West, Florida, United States

Bed

Bath

7

Sleeps

$410.43

brWelcome to Coconut Cottage – Your Luxurious Key West Escape in Bahama VillagebrbrExperience the best of Old Town Key West at Coconut Cottage, a stunning new construction nestled in the vibrant Bahama Village neighborhood. This beautifully appointed 2-bedroom, 2-bathroom home offers an open-concept floor plan, upscale finishes, and an unbeatable location just blocks from iconic attractions, dining, and beaches.brbrThe Primary Suite:brEscape to the entire second floor dedicated to your comfort. The spacious suite features a king bed, a cozy sitting area with a sofa sleeper, a private lanai, and a dedicated workspace. The ensuite bathroom boasts a luxurious soaker tub, walk-in shower, dual vanity, and a large walk-in closet. Zoned central AC keeps this sanctuary perfectly comfortable year-round.brbrGuest Bedroom & Baths:brThe first floor offers a charming guest bedroom with a queen bed and easy access to a stylish hallway bathroom with a custom vanity and beautiful shower.brbrLiving & Entertaining Spaces:brThe open living room and kitchen flow seamlessly to the outdoor entertainment area and pool deck. The kitchen shines with stainless steel appliances, quartz countertops, and a breakfast bar with seating for three. Relax with your favorite shows on the 65 smart TV or dine indoors or outdoors for up to four guests.brbrOutdoor Oasis:brStep through the fully retractable sliding doors to your private tropical retreat. Lounge by the heated (available seasonally) 7’ x 12’ plunge pool with a soothing waterfall feature, surrounded by lush foliage. Enjoy the pool deck with loungers, outdoor dining, and seating areas — perfect for soaking up the Key West sunshine or stargazing at night.brbrExtras You’ll Love:brbrOff-street parking for up to 2 cars — a rare find in Old Town!brbrJust 2 blocks from the lively 1000 block of Duval StreetbrbrMinutes from Southernmost Point, Fort Zachary Taylor Beach, and Truman Annex Waterfront ParkbrbrSecurity cameras on front and side for your peace of mindbrbrPlease Note:brThis is a seasonal rental available for stays of 28 days or longer. Sorry, no pets allowed.brbrReady to book your slice of paradise Coconut Cottage is the perfect blend of comfort, style, and location for your next Key West getaway!

COCONUT COTTAGE- Island Vibes & Cozy Stays W/ Pool & Parking - OLD TOWN KEY WEST

Key West, Florida, United States

Bed

Bath

Sleeps

$1323.92

THE PROPERTY: Enjoy your stay in the tropics at the highly touted Queen Conch complex, which includes 3 separate rentable units: Horse Conch, Rooster Conch, and Sea Conch. You can rent each unit individually, but by renting “Queen Conch” you will enjoy all 3 units and ultimate privacy during your Key West vacation.brbrHorse Conch is located on the second floor, overlooks the pool, and shares a balcony with Rooster Conch. The unit includes one king bedroom (no TV in the bedroom), closet and dresser storage, as well as an ensuite bath with pedestal sink and walk in shower. The open concept living area includes plenty of seating, a flat screen TV and an updated kitchen with stainless steel appliances and table seating for four. brRooster Conch is also located on the second floor, overlooks the pool, and shares a balcony with Horse Conch. The unit includes one king bedroom with a TV, closet, and dresser storage, as well as an ensuite bath with pedestal sink and walk in shower. The open concept living area includes plenty of seating, a flat screen TV and an updated kitchen with stainless steel appliances and table seating for four.br brSea Conch is the larger first-floor unit where you can enjoy people watching on the charming front porch. The home includes one king and one queen bedroom with ensuite baths, pedestal sinks and large walk-in showers. The open concept living area is spacious and includes a flat screen TV, plenty of seating and easy access to the pool area. The kitchen with stainless steel appliances and an abundance of cabinets is fully equipped for the chef in your family. Enjoy meals al fresco via a wall of French doors or in the home’s spacious dining area with table seating for eight. Sea Conch provides you with a wonderful place to entertain during your stay in paradise. brbrAdditional details may be found in each of the rental’s individual property descriptions, however, all units that make up Queen Conch are flooded with natural light and contain cheerful Key West Décor. Enjoyable open concept living is provided in each unit complete with pops of color, flat screen TVs, hardwood floors, and plenty of seating. White kitchens with stainless steel appliances make meal prep a breeze. French doors open onto the covered balcony or decks, allowing you to enjoy indoor/outdoor living. A gas grill is provided for cooking up your catch of the day or burgers for the kiddos. The outdoor pool area is secluded and lushly landscaped for a truly tropical experience. Don’t delay, come out of your ‘shell’, and rent the stunning Queen Conch today! brbrBED CONFIGURATION: By renting Queen Conch, you will enjoy a combined total of four bedrooms, four baths and three pull out sofas that provide sleeping spaces for 14. Sea Conch has one king and one queen bedroom. Rooster Conch and Horse Conch each have one king bedroom. brbrOUTDOOR AMENITIES: The complex boasts lush tropical landscaping and palm trees. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The pool area is adorned with a dining table, umbrellas, and loungers. A gas grill allows you to cook your catch of the day or a great burger! A washer/dryer is in a shed on the left side of the home near the pool.brbrPARKING: Queen Conch offers 1 designated off street parking spot for 1 vehicle. brbrLOCATION: Many Key West attractions are located nearby, as well as numerous restaurants, shops, and galleries. The neighborhood boasts historic conch-style homes. Enjoy café con leche down the street at Cuban Coffee Queen or lunch at 5 Brothers Sandwich Shop. Walk to dinner at Blue Heaven, Caroline’s Cafe, or Sloppy Joe's. You will have many choices located within a 10-minute walk!brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that allow pets.)brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~QUEEN CONCH ~ Amazing location with pool and room for family and friends!

Key West, Florida, United States

Bed

Bath

Sleeps

$290.99

Meticulously restored and maintained 2 bedroom (+ den/3rd bedroom with sleep sofa), 3 full bath home in the heart of Old Town. Relax in an outdoor tropical oasis with dining under the pergola, heated pool with waterfall, outdoor shower, Azek decking, fire pit, gourmet outdoor kitchen, a large front porch with swing, and beautiful landscaping with lighting. Many custom touches including chef's kitchen with granite, wine refrigerator, original Miami Dade pine floors, coffer ceilings, and interior washer/dryer. The extra large lot has a private driveway providing highly desirable off street parking. Master bedroom with queen bed has its own bath with spa shower and separate claw foot tub. Guest bedroom with queen bed has its own bath with spa shower. Den with comfortable full size pull out sofa bed opening to pool area has its own bath with beautiful stone shower. WiFi, AC/heat, ceiling fans. Perfect place to relax and escape. Easy walking distance to the beautiful, historic Basilica of St. Mary Star of the Sea , White Street Art District, Higg's Beach, the White Street Pier, Duval Street, and wonderful restaurants, including Salute on the Beach, Seven Fish, El Siboney Cuban Restaurant, Louie's Backyard and many more. Walk, bike or drive to everything Key West has to offer. Wonderful neighbors to make you feel welcome and at home. Well-behaved small dog considered.

Welcome to Parrot Dice! An Old Town tropical oasis with a private heated pool.

Key West, Florida, United States

Bed

Bath

Sleeps

$376.11

TOP NOTCH LIVING…brNestled in the exclusive Casa Marina district, this newly constructed sanctuary sits only a few blocks from the world famous Duval Street in one of the most desirable neighborhoods of Key West, a serene enclave that's close to vibrant attractions such as the Casa Marina, Resort, Higgs Beach and world class dining and shopping.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brThis impeccable abode offers a spacious 1,743 square feet of modern living with 4 beautifully appointed bedrooms and 3.5 bathrooms. Enter the elevated first floor into the open plan living area that seamlessly connects living, kitchen and outdoor spaces and begs for entertaining with cherished family and friends. The inviting eat-in kitchen features stainless steel appliances, quartz countertops and a separate coffee/bar station with a craft ice maker and beverage/wine fridge. For your convenience, a powder room is located on the first floor and a full size washer and dryer closet is located on the second floor. Youtube TV is available for binge-watching your favorite shows together. brbrSLEEPING ARRANGEMENTS…brTotaling 4 bedrooms, there is a queen bedroom with an ensuite bathroom with a shower on the first level, which is perfect for guests who don't wish to climb stairs. On the second level you will find another king bedroom that shares a full shower bathroom with the twin bedroom (can be converted to a king bed upon request). The 4th bedroom offers a king bed and has its own ensuite shower bathroom. brbrOUTDOOR LIVING…brLuxuriate and unwind in your private pool (comes heated in the cooler months) and deck with al fresco seating a table top propane grill. The floor-to-ceiling sliding glass door of the living room opens up to merge indoor and outdoor living in pure Key West style.brbrPARKING ...brThere is 1 private off street parking space.brbrPETS...brThis is a pet friendly home and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrTHE HEART OF KEY WEST LIVING…

INTO THE BLUE~GRAND OPENING RATES! Pristine 4 BR/3.5 BA Home w/Private Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$234.7

Down a hidden lane in the heart of Old Town Key West you will find Loco Court Cottages. The compound is located one block off Duval Street but is private and serene. The compound consists of three stand-alone cottages alongside a tranquil shared pool. brbrUnit 1 is a One bed, One bath house with an open kitchen and living room and high ceilings. The kitchen is equipped with a refrigerator, oven, induction cooktop, coffee maker, toaster, blender and microwave. Walk out of your living room and bedroom onto a private outdoor patio and dining area with a gas grill. A private washer and dryer is also provided. brbrIn the shared space you will find a spacious heated pool, lush tropical landscaping and ample deck space for sunbathing. brbrThis property is located within short walking distance to some of the best restaurants on the island, including Little Pearl, Lola's Bistro and Antonia's. brbrThis cottage is part of a three-unit property with a shared pool and space for bicycle parking. Parking may be available. Please contact the owner if you require a parking space.

Cottage in Old Town Key West w/ Pool, Parking and Privacy. One block from Duval!

Key West, Florida, United States

1

Bed

1

Bath