Vacation Rentals By Owner In Key West, FL

Summary:brbrRunaway Bills- 2 BDR Main house with 1 BDR Cottage and pool in the Key West downtown.brbrbrbrThe Space:brbrThis charming and stylish Conch home is tucked away on a quiet lane in the heart of Old Town Key West, offering the perfect island retreat. Surrounded by historic architecture and vibrant neighborhoods, this inviting property is just a short stroll from the famous Duval Street, placing you within easy walking distance of restaurants, galleries, shops, and nightlife.brbrbrbrThe main house features two comfortably sized bedrooms, each with king beds, and one full bathroom. Beautiful hardwood floors throughout create a warm coastal character that blends perfectly with the relaxed Key West atmosphere. The fully equipped chef’s kitchen is ideal for guests who enjoy cooking, while the open living area flows seamlessly to a covered outdoor dining space overlooking the pool and deck, perfect for entertaining or relaxing.brbrbrbrAcross the pool, a separate pool house cottage provides additional privacy and includes a third bedroom with a full-size bed, a half bath with toilet and sink, and a private outdoor shower, creating a unique tropical guest suite.brbrbrbrThe fully fenced backyard surrounds a refreshing swimming pool and sun deck, offering a private oasis where guests can unwind after a day exploring the island.brbrbrbrPets are welcome with a non-refundable pet fee, and the property includes the rare convenience of two assigned parking spaces.brbrbrbrAdditional Featuresbrbrbrbr• Central air conditioning and ceiling fans throughoutbrbr• Washer and dryerbrbr• Wireless high-speed internetbrbr• Linens, bath towels, and pool towels providedbrbr• Fully stocked kitchen with cookware, dishes, flatware, and glasswarebrbr• Starter supply of paper and cleaning productsbrbr• Outdoor showerbrbr• Optional housekeeping services availablebrbrbrbrSleeping ArrangementsbrbrbrbrRoadside Bedroom – King BedbrbrMiddle Bedroom – King BedbrbrLiving Room – FutonbrbrPool House Bedroom – Full BedbrbrbrbrThis peaceful yet centrally located home offers the best of Key West living—a private tropical setting just minutes from the island’s most iconic attractions.brbrbrbrGuest Access:brbrE- lock code will be providedbrbrbrbrThe Neighborhood:brbrThe home is located in the heart of Old Town Key West, one of the island’s most charming and historic neighborhoods. Known for its colorful Conch-style homes, tropical landscaping, and laid-back island atmosphere, Old Town captures the authentic spirit of Key West.brbrbrbrJust a short walk away is the world-famous Duval Street, where you’ll find an exciting mix of restaurants, cafés, art galleries, boutiques, and lively nightlife. Guests can enjoy everything from waterfront dining and sunset cocktails to local music and cultural attractions.brbrbrbrThe neighborhood is also close to beautiful beaches, historic landmarks, and parks, including Fort Zachary Taylor Historic State Park, known for its scenic shoreline and excellent snorkeling. Despite being near all the activity, the surrounding streets remain quiet and residential, offering a peaceful retreat after a day exploring the island.brbrbrbrWith its walkable streets, tropical charm, and vibrant local culture, Old Town Key West is truly the perfect place to experience the island lifestyle. brbrbrbrGetting Around:brbrGetting around Key West is easy and part of the fun of visiting the island. Most guests enjoy walking or biking, as many of the main attractions, restaurants, and shops are within a short distance. From the home, you can easily stroll to Duval Street and explore Old Town at a relaxed pace.brbrbrbrBicycles and golf carts are also very popular ways to get around and can be rented nearby. Taxis and rideshare services are readily available, and the Duval Loop shuttle provides a convenient free service throughout much of Old Town. With the island being just a few miles long, it’s simple to explore everything Key West has to offer. brbrbrbrInteraction with Guests:brbrSelf check in

Runaway Bills

Key West, Florida, United States

Bed

Bath

6

Sleeps

$700.87

2 Blocks to Hemingway Home | Designated Workspace | Laundry MachinesbrbrOld Town Key West has a character all its own, and this Bahama Village vacation rental captures it completely. Vintage furnishings, tropical art, a record player, and a guitar set a laid-back, creative tone inside, while a brick patio, gas grill, and string lights await outside. Walk 2 blocks to the Hemingway Home, or settle into your built-in workspace for the week. Island life, on your schedule — book your extended escape!brbr-- THE PROPERTY --brbrINDOOR LIVINGbr- 3 Smart TVsbr- Sitting/storage areabr- Laundry machinesbr- Central A/Cbr- Full futonbr- Eclectic style & decorbr- 1,100 sq ftbrbrOUTDOOR LIVINGbr- Covered front porch w/ loveseat & chairsbr- Brick backyard patiobr- Outdoor dining table w/ chairs & umbrellabr- Deck w/ gas grillbr- Shared yard (2 separate units on-site)br- Gated white picket fencebrbrEAT-IN KITCHENbr- Refrigerator, stove/oven, microwave, blender, toasterbr- French press coffee maker (starter coffee provided)br- Cooking essentials, dishware & flatwarebrbrACCESSIBILITYbr- Single-story home, few exterior steps to accessbrbrPARKINGbr- Street parking around the cornerbr- Car not required if flying into Key Westbrbr-- THE LOCATION --brbr- Classic Conch cottage in Bahama Village — a walkable, character-rich neighborhood steps from Key West's most iconic landmarksbr- 2 blocks to the Ernest Hemingway Home and Museumbr- Under a half-mile to the Southernmost Point of the Continental U.S.A.br- Under a mile to Old Town Key West: Duval Street, the Truman Little White House, the Key West Butterfly and Nature Conservatory, local galleries, restaurants & barsbr- 1 mile to Fort Zachary Taylor Historic State Park Beachbr- 3 miles to Smathers Beachbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires a few exterior steps to accessbr- There are 2 other units on the same property; one of which is used by the owner periodically, and the other is behind this unit and is rented monthly by someone who runs the city, but is very quiet. There is a shared yardbrbrSECURITY CAMERA INFORMATIONbr- 4 exterior devicesbr- Location: doorbell, perimeter of homebr- Coverage: entry & perimeter

Walk to Southernmost Point! Conch Cottage w/ Patio

Key West, Florida, United States

Bed

Bath

Sleeps

$2489.04

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrKey West is known for having amazing properties, but one home stands tall above the rest with its six majestic Royal Palm trees. HOUSE OF THE ROYAL PALMS features a spacious exterior that will make even the most high-end influencer envious. You’ll be spoiled with multiple seating areas, an oversized covered porch, and a swimming pool, all set under those Royal Palms. This estate features two homes: Inside the main house, you’ll discover a home that is as luxurious as it is modern, with an open living room and dining room, an industrial kitchen, high ceilings, and sleek, modern touches throughout. Two of the four primary bedroom suites can be found in the main house. The guest house features the other two suites and a laundry room. Best of all, HOUSE OF THE ROYAL PALMS includes Last Key Realty’s first-class Five-Star Guest Services & Complimentary Concierge, so whether you’re staying for a long weekend or spending a few weeks in paradise, you can rest assured your stay will be unforgettable.brbrTHE LOCATION…brbrIf you decide to pull yourself away from this beautiful home, you’ll realize that the best Key West restaurants, live entertainment, and attractions are all within a few blocks of your front door. While you won’t need a car to get around from this fabulous location, there is off-street parking in the driveway for one vehicle. If you don’t have a vehicle but want to explore the island in a fun way, Last Key Realty’s concierge service can assist with a golf cart, scooters or bike rentals.brbrTHE POOL AREA…brbrUpon entering through the front gate of the property, the six Royal Palms overhead and the pristine gardens welcome you to this private oasis. The spacious exterior and refreshing private pool will certainly be a primary gathering place for your group. Spend those hot South Florida days cooling off in the pool or switch on the pool heater in the cooler months. The entire property is fenced in and landscaped for maximum privacy. Treat your group to a poolside BBQ using the propane grill and outdoor dining table. Just off the pool area is an outdoor shower, a staple for any Key West rental home.brbrTHE LIVING AREA & KITCHEN…brbrThe living area boasts soaring ceilings, comfortable seating options, and a large flat-screen TV. The high ceilings have several skylights, allowing the room to fill with natural light. Multiple French Doors open to the spacious covered porch that sits next to the pool area. The indoor dining table comfortably seats eight, so plenty of room for everyone to gather. The fully equipped kitchen is massive, with enough prep room for a full team of chefs. The kitchen features modern appliances and every cooking tool needed to prepare meals at home. There’s a convenient powder room located just off the living room.brbrTHE ACCOMMODATIONS…brbr** Bedroom Suite #1 - Located in the main house with a King bed, a flat screen TV, a closet, direct access to the porch and pool area, and an en-suite bathroom with a walk-in shower.brbr** Bedroom Suite #2 - Located in the main house with Two Twin beds OR one King bed, a flat screen TV, a closet, direct access to the porch and pool area, and an en-suite bathroom with a walk-in shower.brbr** Bedroom Suite #3 – Located on the First Floor of the Guest House with Two Twin beds OR one King bed, a flat screen TV, a closet, a private patio overlooking the pool area, and an en-suite bathroom with a walk-in shower.brbr** Bedroom Suite #4 – Located on the Second Floor of the Guest House with Two Twin beds OR one King bed, a flat screen TV, a seating area, a closet, a private balcony overlooking the pool area, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen 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** Off-Street Parking for 1 Vehicle in the Drivewaybr** Propane BBQ GrillbrbrOther notes:brbr** Interim housekeeping provided upon requestbr**This property will accommodate up to 8 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**HOUSE OF THE ROYAL PALMS @ OLD TOWN** Estate Near Duval + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$590.09

Welcome to “The Flight Deck” — Your Tropical Getaway in Key WestbrbrLocation: Coral Hammock Community, Stock Island – Just 4 miles from Downtown Key WestbrbrNestled in the sunny paradise of Key West, Florida, “The Flight Deck” is a spacious 3-bedroom, 3-bathroom townhouse located in the private and gated Coral Hammock community. Ideally situated on Stock Island, this home offers the perfect balance of relaxation and convenience—just minutes from the excitement of downtown, yet tucked away in a peaceful, residential setting.brbrProperty OverviewbrbrSpacious Two-Level LayoutbrPerfect for families or groups, this home features:brbrTwo Primary Suites (Upstairs): Each suite includes a king bed, en-suite full bathroom, smart TV, and access to a shared private lanai.brbrGuest Bedroom (Main Level): Offers two twin beds (can be converted to a king upon request) with a full bathroom just steps away in the hallway.brbrComfortable Living and Dining AreasbrbrBright, open-concept living room with sofa (includes a sleeper), armchairs, and a flat-screen smart TVbrbrFormal dining area with seating for up to 8 guestsbrbrWell-equipped kitchen with modern appliances and ample storage for longer staysbrbrOutdoor LivingbrbrPrivate lanais on both levels: one off the upstairs bedrooms, and one off the living room and downstairs bedroom — perfect for morning coffee or evening relaxationbrbrCommunity FeaturesbrbrLarge Shared Pool with plenty of loungers and shaded seating areasbrbrOn-site Fitness Center available for guest usebrbrCovered Parking for two vehiclesbrbrFull-size Washer and Dryer located inside the unitbrbrPrime Stock Island LocationbrbrConveniently located near local favorites, all within walking distance:brbrKey West Golf Club (directly across the highway)brbrHogfish Bar & GrillbrbrRoostica Wood-Fire PizzeriabrbrDolphin DelibrbrStock Island Marina & Yacht ClubbrbrMurray’s MarinabrbrThe Perry Hotel & MarinabrbrGetting to downtown Key West is quick and easy—just a 4-mile drive or bike ride with paved pedestrian and bike paths leading straight into the city. Uber and taxi services are readily available to and from the property.brbrAdditional DetailsbrbrSleeps up to 8 guests comfortablybrbr3-night minimum stay requiredbrbrNo pets allowedbrbrHigh-speed Wi-Fi and central air conditioning throughoutbrbrYour Island Retreat AwaitsbrbrWhether you're planning a family vacation, a group getaway, or a seasonal escape, “The Flight Deck” offers the space, comfort, and location to make your Key West stay unforgettable.

The Flight Deck - 3 Bedroom / 3 Bathroom with Shared Pool & Fitness Center!

Key West, Florida, United States

Bed

Bath

Sleeps

$236.12

Completely updated condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with flair and detail. Open design with new flooring, coastal hues and furnishings -feels spacious and decadent. The kitchen boasts new stainless appliances, and a show-stopping chandelier. After a day of frolicking, slip into the new bed featuring cozy organic bedding. The double French doors lead to a huge deck- perfect for morning coffee, or happy hour entertainment. The Shipyard includes a heated pool, assigned parking, security, and tree shrouded walking paths. The condo is perfectly placed in the very desirable Truman Annex offering a tranquil neighborhood, yet so close to the newly developed Truman Waterfront Park, Fort Jefferson State Park and its popular beaches, and the excitement of Duval St.brPlease note: The minimum rental period is 27 nights

Condo

Ahoy Mate! with Compass Realty at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

4

Sleeps

$444.32

This listing is for a room within a hotel.brbr✦ Your room is 200 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. Pets allowed: $50/night, no restrictionsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

Hotel

Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier

Key West, Florida, United States

Bed

Bath

Sleeps

$518.3

Your Key West adventure begins at this 2-bedroom condo. Inside, guests find two king beds that promise restful nights The condo features two bathrooms, each equipped with a hair dryer for added convenience. Stay comfortable with air conditioning throughout the unit, and keep up with your routine in the fitness room just steps away. Beautiful swimming pool on property. 4 adult max , no children , no pets of any kind owner has serious allergie.

Condo

1800 ATLANTIC 2-bedroom condo with Particle Ocean view in Key West Florida

Key West, Florida, United States

Bed

Bath

Sleeps

$357.9

THE PROPERTY: Enjoy your stay with us at Robinson Crusoe Cottage, part of the quaint Conch Cottages property, which includes 3 separate rentable units: Robinson Crusoe Cottage at the rear, Royal Poinciana Cottage on the right, and Margarita Cottage on the left. You can rent each unit separately or rent Conch Cottages to enjoy all 3 units and ultimate privacy during your Key West vacation.brbrA brick walkway paves the route through the front gate and to your private rear entrance. Here you will find lovely palm trees and lush landscaping. A shared, seasonally heated pool is also located in the rear of the property and is adorned with decking and loungers. Surrounded in sunshine, the pool is the perfect place for relaxing while working on your tan. Enjoy cocktails poolside or outdoor dining. A grill is provided for the chef in your group. No chef, no worries. You can walk or bike to nearby El Siboney, a well-known Cuban restaurant. Inside the cottage is an updated kitchen with refrigerator, microwave, toaster, and coffee maker. Preparing meals or a quick snack is easy in this well-equipped kitchen. *Please note this cottage has no dishwasher. The large living area is complete with a TV, pull-out sleeper sofa, end tables, and a dining table. Your queen bedroom is adorned with nightstands, bedside lighting, a TV, and closet. Its updated bath includes a large single vanity and sink and a tiled, walk in shower. Great for entertaining friends or keeping an eye on the kids, this open concept cottage has everything you need to enjoy a blissful stay. brbrBED CONFIGURATION: There is one queen bed in the bedroom and a sleeper sofa in the main living area. brbrOUTDOOR AMENITIES: A shared, seasonally heated pool and lounge chairs are provided for your enjoyment. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The pool house has a shared washer and dryer for guests. A grill and dining table are provided for outdoor meals in the sunshine. brbrPARKING: There is no designated parking space however, street parking may be available in the surrounding neighborhood. brbrLOCATION: Located in the heart of Historic Old Town, you can walk or bike to Duval Street, shops, bars, and restaurants. Enjoy nearby entertainment on Mallory Square. 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***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~ROBINSON CRUSOE COTTAGE~ Delight in island vibes in this home with a pool.

Key West, Florida, United States

Bed

Bath

Sleeps

$319.48

THE PROPERTY: Enjoy your stay with us at Margarita Cottage, part of the quaint Conch Cottages property, which includes 3 separate rentable units: Margarita Cottage on the left, Royal Poinciana Cottage on the right and Robinson Crusoe Cottage in the rear. You can rent each unit separately or rent Conch Cottages to enjoy all 3 units and ultimate privacy during your Key West vacation.brbrStroll the streets of Key West by day and relax in your own cottage at night. Or enjoy the seasonally heated pool by day and the sights and sounds on Duval Street at night. Either way, this quaint cottage provides all you need to soak up island vibes anytime. brbrAs you enter the home via the main gate, you will find a full kitchen with updated appliances including a refrigerator, microwave, toaster, and coffee maker. *Please note this cottage has no dishwasher. A queen bed with a dresser, smart TV, night stands and bedside lamps allow for a comfortable sleep. The bedroom provides access to your private front porch from which you can enjoy morning coffee and people watching. The tiled bathroom has a pedestal sink and walk-in shower. A hall closet provides storage for your luggage and an instant water heater. Out back is a beautifully refreshing shared pool. Your deck has a grill and an outdoor dining area with a bistro table and chairs. Enjoy the lush landscaping and tropical breezes while napping or reading a book. Work on your suntan poolside or converse with friends and family; the options are limitless. Don’t wait, book your island getaway at Margarita Cottage now! brbrBED CONFIGURATION: There is one queen bed that sleeps 2. brbrOUTDOOR AMENITIES: A shared, heated pool and lounge chairs are provided for your enjoyment. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The pool house has a shared washer and dryer for your use. Grill your catch of the day while enjoying dinner under the stars, surrounded by nature and swaying palm trees. brbrPARKING: There is no designated parking space however, street parking may be available in the surrounding neighborhood. brbrLOCATION: Located in the heart of Historic Old Town, walk or bike to Duval Street, shops, bars, and restaurants. El Siboney Cuban restaurant is just around the corner. Enjoy nearby Key West nightlife or entertainment on Mallory Square. 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***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise.

Key West, Florida, United States

Bed

Bath

Sleeps

$290.71

THE PROPERTY: Enjoy your stay with us at Royal Poinciana Cottage, part of the quaint Conch Cottages property, which includes 3 separate rentable units: Royal Poinciana Cottage on the right, Margarita Cottage on the left, and Robinson Crusoe Cottage in the rear. You can rent each unit separately or rent Conch Cottages to enjoy all 3 units and ultimate privacy during your Key West vacation.brbrAfter breakfast in bed, stroll outside for a dip in the shared pool! Complete with a new deck and lounge chairs, this is an ideal spot to enjoy island life. Surrounded by palm trees and lush greenery, a sense of tranquility will wash over you in no time. Inside the home, you will enjoy a restful sleeping space with a queen bed, nightstands, and smart TV. An updated ensuite bath is complete with pedestal sink and tiled walk-in shower. The bedroom also provides access to your private front porch from which you can enjoy evening cocktails and island breezes. A hall closet provides storage for your luggage and an instant water heater. The updated kitchen includes a refrigerator, microwave, toaster, and coffee maker. *Please note this cottage has no dishwasher. Your private deck includes a grill and outdoor bistro set. If you prefer not to cook while on vacation, you can walk to nearby El Siboney, a local Cuban restaurant. Walk a few blocks further and you will find yourself on Duval Street where you can enjoy additional restaurants, bars, galleries, and world-class shopping. Vibrant Key West nightlife and stunning sunsets on Mallory Square are also within walking distance. This home provides you with a comfortable place to relax as well as a vantage point from which you may explore the island. Either way, you can’t go wrong. We welcome you to enjoy yourself at Royal Poinciana Cottage soon! brbrBED CONFIGURATION: There is one queen bed in the cottage. brbrOUTDOOR AMENITIES: A shared, heated pool, lounge chairs and a grill are provided for your enjoyment. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The pool house has a shared washer and dryer for guests. Dine under the stars or enjoy a peaceful night swim on the island. brbrPARKING: There is no designated parking space however, street parking may be available in the surrounding neighborhood. brbrLOCATION: Located in the heart of Historic Old Town, you can walk or bike to Duval Street, shops, bars, and restaurants. Enjoy nearby entertainment on Mallory Square. 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***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~ROYAL POINCIANA COTTAGE~ Come and indulge yourself in some KW sunshine!

Key West, Florida, United States

Bed

Bath

Sleeps

$895.36

THE PROPERTY: Enjoy your stay with us at the quaint ‘Conch Cottages’ property, which includes 3 separate rentable units: Margarita Cottage, Royal Poinciana Cottage, and Robinson Crusoe Cottage. You can rent each unit separately or rent ‘Conch Cottages’ to enjoy all 3 units and ultimate privacy during your Key West vacation.brbrFriends that travel together, stay together and you can travel together here! As you enter the property via the main gate, Margarita Cottage is on your left , Royal Poinciana Cottage is on your right and Robinson Crusoe Cottage is between them in the rear. The Margarita and Royal Poinciana Cottages have full kitchens with a refrigerator, microwave, toaster, and coffee maker. *Please note neither has a dishwasher. Each of these studio cottages has a smart TV, dresser, night stands and a queen bed, providing you with comfortable sleep. Each studio bedroom provides access to a private front porch from which you can enjoy morning coffee and people watching. A tiled bathroom with pedestal sink and walk-in shower can be found in each studio cottage. Each hall closet provides storage for your luggage and houses an instant water heater. brbrRobinson Crusoe cottage is the largest of the cottages. Its kitchen has everything you need including a refrigerator, microwave, toaster, and drip coffee maker. *Please note it does not have a dishwasher. The open-concept room includes a pull-out sofa, end tables, a dining table, and TV. It has a traditional queen bedroom and hall bath with walk-in shower. The bedroom has a TV, nightstands, bedside lamps, and a closet. brbrOut back is the shared seasonally heated pool as well as a grill and dining table for each unit. All three cottages have natural light and lush landscaping in a fabulous location. Venture out on your own or with your group because you won’t want to miss some of the top things to do in Key West. Visit the Ernest Hemingway Home and Museum, Fort Zachary Taylor State Park and Beach, and the Southernmost Point, to name a few. Enjoy family time around the pool or conversation with friends, you can’t go wrong no matter what you choose. Book your friends and family getaway at Conch Cottages today! brbrBED CONFIGURATION: There is one queen bed in Margarita Cottage. There is one queen bed in Royal Poinciana Cottage. There is one queen bed in the bedroom and a sleeper sofa in the main living area in Robinson Crusoe Cottage. brbrOUTDOOR AMENITIES: A shared, seasonally heated pool and lounge chairs is provided for your enjoyment. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The pool house has a shared washer and dryer for guests. Three grills and dining or bistro tables are provided for outdoor meals in the sunshine. brbrPARKING: There is no designated parking space however, street parking may be available in the surrounding neighborhood. brbrLOCATION: Located in the heart of Historic Old Town, you can walk or bike to Duval Street, shops, bars, and restaurants. Enjoy nearby entertainment on Mallory Square. 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***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!

Key West, Florida, United States

Bed

Bath

8

Sleeps

$333.24

A Cayo Hueso Retreat - This lovely, fully furnished, townhouse has 3 bedrooms and 2.5 baths . The master suite has a king bed and offers an ensuite bathroom with walk in shower. A screened in balcony leads out for evening drinks to relax and unwind or morning coffee to start the day as you look over the greens and pond views. The two guest bedrooms upstairs offer full and twin beds (which can be converted to King on request) and share an additional full bathroom in the hallway with tub/shower combo. Dressers, and closets are provided for storage. A rear screened in porch from the living room overlooks the golf course and offers tranquil nature and water views with al fresco dining for up to 6. This home offers a fully equipped kitchen with dishwasher and microwave. Flat screen Smart TVs in the living room and each bedroom with cable and complimentary Wi-Fi service. Amenities include two community pools, on-site gym, and parking for up to two vehicles. Please note this home is offered for 28 night minimum rentals.

A Cayo Hueso Retreat at the Key West Golf Club

Key West, Florida, United States

Bed

Bath

Sleeps

$141.42

- Walkable to Duval Street and beaches. br- Heated Pool shared by just four units.br- Private Parking spot.br- Two private outdoor spaces – greet the sunrise on the covered balcony, toast the sunset on a second, tree‑top perch.brbrEscape to the heart of Old Town Key West, where historic charm meets easy island living. This cozy cottage offers two private outdoor spaces, a shared heated pool, and the rare convenience of assigned parking - all just minutes from Duval Street, the beach and local favorites. Whether you're here to explore or unwind, this is your home base for a relaxed Key West Getaway.brbrThe space:br- Primary bedroom: Queen bed.br- Bath: Shower, plush towels, starter toiletriesbr- Living area: Spacious open concept with library, dedicated Wi‑Fibr- Kitchen: Full‑size range, fridge, dishwasher, basics stockedbr- Outdoor: Covered balcony (bistro set), open balcony (loungers), shared tub and pool, tropical gardensbr- Parking: 1 assigned off‑street spot (rare in Old Town)brbrbrLocale:brStroll to Higgs Beach (0.3 mi) for sunrise yoga and beach walk, brunch at various great Old Town restaurants (0.2mi), and Mallory Square sunsets (1.0 mi). Historic Seaport, galleries, and live music are all within walking or a short bike ride.brbrReady for a month of island living Click Request to Book and start counting down to Key West!

Back to the Island. Central to Old Town hot spots Pool, balconies, parking

Key West, Florida, United States

Bed

Bath

Sleeps

$1048.49

Relax in this tropical poolside townhouse in the heart of Key West. Wake up surrounded by lush tropical landscaping and enjoy morning coffee on balconies overlooking the shared pool. Three levels provides for unparalleled privacy. Shopping and restaurants are within walking distance, prepare a gourmet meal in the fully equipped kitchen, or grill poolside. Take a dip in the pool or walk to the beach. Feel secure in the gated 3 unit compound with covered off street parking.brbrThe Cathouse on Catherine, hosted by Nautipussy is a townhouse located in the White Street Gallery district. Three units comprise this private gated mini compound. The large 40X16 pool is the focal point of the property with plenty of outdoor seating, dining and lounging. brbrOn the first level, you'll enter into the open floor plan - living room with sofa sleeper, 55 Inch smart tv, the dining area, and a U shaped kitchen features stainless appliances, solid countertops, icemaker, coffee maker, microwave and toaster. The washer and dryer and a 1/2 bathroom are also conveniently located on the first level. Double french doors open from the dining area to a private deck on the side of the home. brbrA classic oak stairway to the 2nd level brings you to a king bedroom with 40 inch smart tv, a full size bathroom and an open area with desk and two XL twin beds that will sleep an additional two persons, and a 50 inch smart tv. Double french doors open to a covered porch overlooking the pool.brbrThe stairs to the 3rd level bring you to two additional bedrooms. A king bedroom with 40 inch smart TV and a third bedroom with two queen beds and 40 inch smart TV have a shared Jack & Jill bathroom that adjoins between the two rooms. Enjoy streaming on all the smart TVs.brbrThe outdoor area is great to entertain or lounge around the pool. There are two tiki bars, plenty seating for al fresco dining, and a gas grill all for your exclusive use. There is also a charcoal grill available.brbrThis property is ideal for large family gatherings, multiple vacationing families, and bachelor/bachelorette parties.brbrThe city tennis courts are just two blocks away. You are also within 2 blocks of a grocery store and several restaurants. Duval Street with it's many attractions, restaurants and nightlife is only a 15 minute walk (less than a mile away), or enjoy a 15 minute walk to the beach.brbrThe Cathouse on Catherine hosted by Nautipussy welcomes you!

The Cathouse, an Old Town tropical poolside oasis with huge, heated pool

Key West, Florida, United States

Bed

Bath

Sleeps

$256.67

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: This beautifully remodeled townhouse invites its guests to enjoy the peace and serenity of island life. Decorated with new art and accessories, this warm and inviting home is tucked back inside a gated community. Newly painted inside and out, the townhome features new hardwood flooring, hurricane doors and windows, air conditioning and a Trex-covered front porch that is the perfect place to enjoy afternoon cocktails. Other recently added amenities include a new washer and dryer, new sofa and new water heater.brbrAs you enter the gate, you will pass by the shared pool and gardens. Step inside to the spacious living room with plenty of seating, a new sofa and area rug as well as a large screen TV. You will also find a conveniently located half bath in this area.brbrMoving on toward the rear of the home, you will enter the dining area and a newly remodeled kitchen, adorned with tiled floors, white cabinetry, black granite countertops and stainless-steel appliances, including a new microwave. The sleek kitchen is open to the hardwood floored dining area which allows you to mingle with guests while preparing gourmet delights. From here, the sprawling wall of glass provides access to your private, fenced patio with Trex decking, BBQ grill and garden. Enjoy the sunshine, read a book, or prepare a meal for friends.brbrThe home’s second floor features 2 bedrooms and a bunk room, as well as 2 full baths. The primary bedroom includes an ensuite bath, beautifully updated with marble, tile and a large glass shower. Enjoy your favorite program on the new, large screen TV. A closet with louvered doors provides plenty of storage for clothing or luggage. French doors lead to a covered porch where you can enjoy your morning coffee and views of the tropical gardens and courtyard.brbrThe windows in the ample second bedroom provide plenty of sunshine. White decor, a TV, closet, and a dresser compliment the room. The third sleeping space includes bunk beds that will be sure to appeal to your children or the “grands.” This room does not have a closet but does have a small dresser and clothes tree for storing items for the little ones. The second bedroom and bunk room share a completely renovated bath with a shower/tub combination.brbrThis gated community is tucked back away from the hustle and bustle of downtown Key West but close enough to it, should you decide to venture out. Duval Street and all it has to offer is just a short walk, Uber, or bike ride away. Or you can choose to rest and relax in the privacy of this tranquil townhome.brbrBED CONFIGURATION: All bedrooms are on the second floor in this two-story townhome. Bedroom one boasts a king size bed and updated ensuite bath. Bedroom two includes a queen bed and access to the hall bath. A third room includes bunk beds and access to the hall bath.brbrOUTDOOR AMENITIES: A shared pool with courtyard furniture and gardens adorn this small complex. Your home includes a fenced garden area with BBQ grill and seating. The porches in the front of the home and primary bedroom are covered and provide a respite from the summer sun.brbrPARKING: There is a designated parking space for one vehicle, which is a great feature in Key West, where parking is limited.brbrLOCATION: This townhouse is in Old Town, Key West, in a private enclave in the Historic District. It is near the southern end of Duval Street, the Casa Marina area, and the White Street Galleries. From here you can also walk or bike to Higgs Beach, coffee shops and restaurants.brbrPETS: Pets are not allowed in this home. Please view our many other homes that are pet-friendly.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***

~Reel Paradise~Beautiful private townhouse in a small gated community.

Key West, Florida, United States

Bed

Bath

5

Sleeps

$659.41

PROPERTY: Enjoy your coffee on the front porch or listen to the birds while gliding on the swing. Either way, you will acclimate to the Key West vibe in no time. brbrLocated on a teeny tiny quiet lane, this beautifully renovated home is trimmed with a white picket fence and boasts solid surface floors and an open concept living room/kitchen. The gourmet kitchen is equipped with everything you need to prepare meals or to snack around the large kitchen island with seating for four. Plenty of cabinets, granite counters and stainless-steel appliances round out the kitchen. The living room with TV, ceiling fan, and comfortable furnishings has seating for everyone. From here you may spill out onto the deck via the expansive glass doors. Once outside, you can chill in your private hot tub and wash your cares away. brbrEach bedroom is superbly furnished and includes an ensuite bath with glass walk in shower. The primary bedroom enjoys a unique ambiance provided by obscure lighting in the vaulted ceiling. The room is also flooded with natural light and adorned with plantation shutters, beautiful bedding, dresser, TV, closet, and bedside wall lighting. The second bedroom is also beautifully furnished and includes bedside wall lighting, ceiling fan, TV, dresser, and your own entrance to the deck. Vacationing in this home will prove to be enjoyable, relaxing, and have you wanting to come back before you even leave. brbrBED CONFIGURATION: Each king bedroom has an ensuite bath, bedside wall lighting and beautiful furnishings. brbrOUTDOOR AMENITIES: Private wrap around deck with hot tub and outdoor shower. Comfortable seating, an umbrella dining table with chairs and a gas grill are provided for your enjoyment. Your own washer/dryer is in the outdoor laundry closet. brbrPARKING: One on-site parking space is available for a small car. Please note this home is on a tiny, one-way lane. brbrLOCATION: Located on a quiet lane in Old Town, less than 2 blocks from Duval Street. From here you can walk to many of Key West’s attractions, shopping, restaurants, and bars. A short walk away is the stop for the Duval Loop (a free bus service) to assist you in getting around downtown.brbrPETS: This home is not pet friendly. Please browse our other pet friendly properties.brbrSMOKING: This is a non-smoking home and property. This includes the HOT TUB area.brbr***Guests must be 25 years of age or older unless accompanied by an adult. brbr***Managed by Historic Key West Vacation Rentals***

~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.

Key West, Florida, United States

Bed

Bath

Sleeps

$261.93

ISLAND TIME AWAITS…brStep up to this serene, tropical cottage inviting you in with a multitude of swaying palms, a private front porch and a picture-perfect white picket fence. Situated in the midst of Key West, this home pulls you into the timeless, historic feel of Old Town Key West and away from our real world worries. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brFollow the side hall beyond the bedrooms to an open concept Great Room that overlooks the pool deck filled with tropical vegetation. Snack inside at the breakfast bar for 3 in the fully equipped kitchen or enjoy the evening's breeze outside at the dining table for 4. Wood floors, ceiling fans and natural lighting throughout create a light and airy feel throughout this Key West retreat. Tropical décor paired with vaulted ceilings and wooden beams create an inviting ambiance with endless character. brbrSLEEPING ARRANGEMENTS…brFeaturing 2 bedrooms with two ensuite bathrooms, this home allows for privacy amongst family or couples traveling together. Both bedrooms come with a queen size bed, storage for clothing, a flat screen TV and full bathrooms with the front room having a walk in shower and the 2nd bedroom having a shower/tub combination. brbr OUTDOOR LIVING…brLet your worries wash away out on your private pool deck area surrounded by lush landscaping making you feel like you are truly immersed in Paradise. Catch some shade under the porch's awning and soak up the peaceful surroundings. Allow the sunny afternoon to flow into a cool, breezy evening as you swim under the stars in the private heated pool and grill up your fresh catch of the day. A washer/dryer is available in an enclosure off the back patio area, and the owner also provides 2 bikes for your use. This Old Town gem is just a short distance from all the action on Duval St. yet tucked away for a peaceful evening’s rest. brbrPETS...brSmall dogs are considered for this home and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)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...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).brbrVACATION NEVER FELT SO GOOD...

HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!

Key West, Florida, United States

Bed

Bath

4

Sleeps

$283.2

A 3/2 home in the historic district of Old Town Key West with soaring ceilings and a ton of character. Walk to Duval, but nestled in a quiet neighborhood next to St. Mary Star of the Sea. Each bedroom features a private balcony. We believe the house was built in the late 1800’s. It was moved in the 30’s when the land it sat on was taken for use by the Navy. The land it originally sat on is where the post office is now near the corner of Fleming and Whitehead. The home features original Miami Dade pine floors and walls with soaring ceilings.

Old Town Historical Charm

Key West, Florida, United States

Bed

Bath

Sleeps

$321.32

Summary:brbrDoc's Paradise @Key West Golf ClubbrbrbrbrThe Space:brbrEnjoy the ultimate month-long Key West Vacation in the comfort of a gated community of Key West Golf Club. This 3BDR/3BA detached, two-story Conch Style Townhouse is nestled at the end of quiet Spoonbill Way. The main living floor offers an open floor plan Kitchen, Dining, and Living Room and extends to the screened outdoor porch.brbrThe third bedroom/office is on the first floor and has a full bathroom with a standing shower. Crown moldings, high ceilings, and Brazilian cherry wood floors complement the two en-suite bedrooms on the upper floor. Beautiful balconies allow the private enjoyment of the lush greenery. Key West Golf Club amenities include two pools, a private gym, and 24-hour manned/gated security in a park-like setting.brbrbrbrDoc's Paradise Features:Master bedroom with Queen Bed, Guest Bedroom with Queen bed, Downstairs Office with Full-size BedbrbrThree full bathrooms with stand-up showers and a tubbrbrBonus screened-in porch and a private gardenbrbrParking for 2 vehiclesbrbr2 shared pools and a gymbrbrbrbrWasher/DryerbrbrCentral A/CbrbrCeiling FansbrbrSmart televisionsbrbrFully equipped kitchenbrbrStarter supply of paper productsbrbrStarter set of cleaning productsbrbrLinens and towels providedbrbrWireless high-speed Internet accessbrbrInterim housekeeping provided upon requestbrbr2 bikesbrbrpack and playbrbrbrbrThis property will accommodate up to six adultsbrbrGuests must be 25 years of age or older unless accompanied by an adultbrbrThis is a non-smoking home and propertybrbrbrbrA RENTAL AGREEMENT IS REQUIRED TO BE SIGNED

Doc`s Paradise

Key West, Florida, United States

Bed