Vacation Villa Rentals By Owner In Key West, FL

$357.48

Southern Escape at Truman Annex - 2 Bed / 2.5 Bath with Parking & Shared Pool

Key West, Florida, United States

brWelcome to Southern Escape — Your Perfect Key West Getaway!brbrNestled in the heart of the Truman Annex Foundry building, Southern Escape is a beautifully remodeled 2-bedroom, 2.5-bath townhome designed with your comfort and relaxation in mind. This stylish retreat comfortably sleeps up to 6 guests, featuring a king bed in the primary suite and two twin beds in the guest room — which can easily convert to a king upon request.brbrEnjoy bright, sun-filled living spaces with light wood floors, quartz countertops, stainless steel appliances, and plush furnishings. The open floor plan includes a cozy living room with a sleeper sofa and a large 55” flat-screen TV, perfect for unwinding after a day of exploring.brbrLocation is everything: Just 3 blocks from the vibrant Duval Street, 2 blocks to the serene Truman Waterfront, and a short walk to Fort Zachary Taylor Beach, Southern Escape puts you right in the center of Old Town Key West’s best attractions — no car needed!brbrHome highlights:brbrFirst Floor: Open living and dining area with ample natural light, updated kitchen with full-size appliances, and a convenient half bath.brbrSecond Floor: Primary suite with king bed, workspace, flat-screen TV, ensuite bathroom, private balcony, and in-suite laundry (full-size LG washer/dryer).brbrThird Floor: Guest bedroom with twin beds (convertible to king), ensuite bathroom, and plenty of storage.brbrOutdoor Spaces: Fenced courtyard, front lanai with seating, gas grill, and a shared pool with lounge chairs and restrooms. Towels provided!brbrParking: One assigned parking spot included.brbrNeed more space Book our sister property, Banana Wind (Unit 18), just steps away for your larger group.brbrWhether you’re here to relax by the pool, stroll through Old Town, or explore Key West’s famous sights, Southern Escape offers the perfect home base for an unforgettable vacation.brbrBook your stay today and experience the best of Key West living!

2

Bed

2

Bath

6

Sleeps

$519.57

/ Nightly

Private Vacation Home

SERENITY ON SUNRISE ~ 5 BR/5.5 Bath New Town Home w/ Pool & Dockage!

Key West, Florida, United States

MASTERPIECE CANAL ESTATE ON ELEGANT LANE...brLocated on Key West's only canal system in quiet New Town, this expansive sanctuary with a detached guest cottage sets you in the ultimate lap of luxury. Nestled in a garden of mature lush vegetation from every angle, this timeless pool home is saturated with privacy for your large group, offering endless opportunities to unwind in unmatched island splendor. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brNo detail has been spared to indulge your every whim in this sleek and modern residence. Enter into your immense living and dining area that is punctuated by a wall of glass, inviting your outdoor oasis to merge with your opulent indoor space. A chef's kitchen with high-end appliances and culinary tools (including a beverage fridge, Scotsman nugget ice machine, blender, crock pot and Nutribullet) will inspire lofty meals prepared for your cherished family and friends. Ample and plush seating accompanied by an electric fireplace will encourage many satisfying hours spent relaxing and unwinding in this one-of-a-kind abode. For your convenience, a spacious washer and dryer area and powder room reside in the bedroom hallway. brbrSLEEPING ARRANGEMENTS...brEnjoy perfect slumber in one of the 4 main house bedrooms all with gorgeous modern en suite shower bathrooms, the primary suite also equipped with an automatic bed with a split mattress top and a large soaking tub. This home offers 2 king guest rooms, a queen guest room, and a twin guest rooms (twins do NOT convert to a king). The large separate guest cottage features its own living area with a sleeper sofa, full kitchen, washer/dryer, shower bathroom and king bedroom for completely independent living from the main house (not wheelchair accessible).brbrOUTDOOR LIVING...brAn exquisite screened porch offers al fresco dining and entertaining for your large group. Your sparkling pool (comes heated in the winter months and can be chilled upon request in the warmer months) with outdoor shower and oversized dock (outfitted with cleats for more than one boat) are framed by a backdrop of mangroves where you may spot a variety of southernmost wildlife. A fishing and boat lover's nirvana!brbrPARKING....brThis home has off street parking available for 4 vehicles.brbrPETS...brThis is NOT a pet friendly home.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)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!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.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). brbrHEAVEN IN WONDERLAND...

Bed

Bath

Sleeps

$258.52

/ Nightly

Condo

A Sunrise Lookout-B605

Key West, Florida, United States

***60 DAY MINIMUM STAY IS REQUIRED***A perfect beach getaway in Key West! See the Sunset and stroll the sidewalks at this fabulous location away from the crowds but an easy 5 minute ride to the historic Old Town district. This fully turn key condo has all the amenities you would desire in a home away from home. Start your stay on the island in this 6th floor, 2 bedroom, 2 bath condo (elevator access to 6th floor). A spacious open kitchen has a selection of kitchen supplies to match your culinary skill. Well equipped with a variety of glassware, place settings and service pieces. You can also relax and watch tv in the open living room after a day of fun in the sun. Full-size washer and dryer is also included in the unit.brWalk across the street along the beach for a refreshing morning or evening stroll on Smathers Beach. Bring your rackets and tennis balls to take advantage of the onsite tennis courts or just enjoy the on site pool. Parking for up to 2 standard size vehicles are available. ***60 DAY MINIMUM STAY***br**NO PETS**

Bed

Bath

Sleeps

$2,863

/ Nightly

Private Vacation Home

**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrKey West has a unique way of appealing to anyone and everyone that visits the island, and it's easy to see why: the laid-back way of life, the historic charm and walkability of Old Town, and the overall 'good vibes' that the island has to offer those needing an escape from the day to day hustle and bustle of the real world. These same appealing characteristics can be found in this recently renovated Old Town home, offered for vacation rental exclusively by Last Key Realty. GOOD VIBRATIONS has four bedrooms, each complete with its own en-suite bathroom for ultimate privacy, a spacious living area, a private heat-optional saltwater pool, a fully equipped kitchen, off-street parking, and best of all a location that simply cannot be beat, on a quiet lane just half a block from the world-famous Duval Street. This home paired with Last Key Realty's unrivaled Guest Services will have you feeling those GOOD VIBRATIONS for your entire stay in Paradise!brbrTHE LOCATION...brbrIf you decide to pull yourself away from this wonderful home, you'll realize that the best restaurants, live entertainment and attractions are all within a block or two. Yet, this home is tucked away down a quiet nondescript lane that you wouldn't be able to find without directions. While you won't need a car to get around from this fabulous location, there is a designated off-street parking space if you decide to bring one, plus plenty of room for bicycles or scooter rentals, all coordinated by Last Key Realty's concierge service upon request.brbrTHE LIVING AREA...brbrGOOD VIBRATIONS was designed to enjoy Key West in style, while sleeping the whole gang under one roof. The open living area is ideal for gearing up to head out or for unwinding after a day of exploring Old Town. The living room has a large flat screen SMART TV that can be enjoyed from the cozy living room furniture, including a pull out couch, or on the island-inspired dining table. The fully equipped kitchen is next to the living room, with every appliance and tool needed to prepare a meal at home in between enjoying the array of Old Town restaurants within walking distance of your front door.brbrYou'll find the fully equipped kitchen next to the living room, with every appliance and tool needed to prepare a meal at home in between enjoying the fabulous array of Old Town restaurant options within walking distance of your front door.brbrYOUR PRIVATE SALTWATER POOL...brbrThe living area opens up to the fully fenced private pool area, with equal amounts of sunshine and shade all day. The saltwater pool can be heated in the cooler months and is surrounded by comfortable chaise lounges and chairs for relaxing outdoors. Pleasant outdoor artwork decorates the fence and there's an outdoor shower for rinsing off after a swim or a day at the beach. The BBQ grill and outdoor dining set are perfect for a poolside cookout.brbrTHE ACCOMMODATIONS...brbr• Coral Suite: Located on the First Floor with Two Twins OR One King bed, a flat screen TV, direct access to the Pool Area, and an en-suite bathroom with a walk-in shower.brbr• Chemistry Suite: Master Bedroom: Located on the Second Floor with a King bed, a large flat screen TV, a balcony overlooking the Pool, and an en-suite bathroom with a combination tub & shower.brbr• Vintage Suite: Located on the Second Floor with Two Twin beds OR One King bed, a flat screen TV, and an en-suite bathroom with a walk-in shower.brbr• Golfer Suite: Located on the Second Floor with Two Twins OR One King bed, a flat screen TV, a balcony overlooking the Pool, 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 and full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Fully Fenced and Lushly Landscaped Private Yard br• Private Saltwater Pool with available Pool Heatbr• Outdoor Showerbr• Assigned Off-street Parking Space (with restrictions - NO LARGE VEHICLES) Propane BBQ GrillbrbrOther notes:brbr• Interim housekeeping provided upon request br• This property will accommodate up to 10 adults br• 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.brbrNEED MORE SPACE...brbrLast Key Realty manages neighboring homes on either side of Good Vibrations with passthrough gates to the pool areas that can be unlocked to accommodate larger groups in combinations of these homes. Find these homes on the Last Key Realty website, or inquire for details.

Bed

Bath

Sleeps

$1983.54

/ Nightly

Private Vacation Home

Coastal Comfort & 3/4 Time Compound

Key West, Florida, United States

This compound is comprised of two homes in exclusive Key Cove Landings, by combining Coastal Comfort and 3/4 Time, two 4-bedroom homes! brThe perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on the driveways in front of the homes.brKey Feature:br6 en'suite bedrooms in addition to a bedroom in each home off the living room, each with two twin beds.brThe homes have the same large open floorplan with spacious seating areas. brThe master bedrooms have King-sized beds, large flat-screen HD TVs, and en-suite bathrooms complete with a glass showers, large Jacuzzi tubs and separate room for the facilities. Second bedrooms have King-sized bed, flat-screen HD TVs, large walk-in closets, and glass sliding doors providing access to the waterfront balcony. The bathrooms are en-suite. The third bedrooms are also on the 2nd floor with en-suite bathroom. brWe suggest looking at each individual listing for more specific information on each of the homes that comprise this Key Cove Landings compound.brAMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 16.brbrThis compound does not include dockage.brbrRATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

8

Bed

7

Bath

16

Sleeps

$459.7

/ Nightly

Private Vacation Home

Waterfront Boater's Paradise on deep water canal, boat dock, ocean access

Key West, Florida, United States

Tropical WATERFRONT getaway. A Boater's Paradise. This charming 4 bedroom (1 King, 3 Queens), 2 bath house is located on a deep-water canal with direct ocean access. This coastal retreat is a boater's dream featuring a seawall and dock that can accommodate most any size boat. Embrace outdoor living with kayaks, paddleboards and plenty of space for entertaining. Grill, Outdoor Shower. Located on Stock Island, just 15 minutes from downtown Key West, this property combines serene seclusion with easy access to shopping and dining.

Bed

Bath

Sleeps

$196.25

/ Nightly

Condo

Ocean View Monthly Rental at 1800 Atlantic- Open Nov, December & January

Key West, Florida, United States

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.brbrbrWelcome to our paradise! We invite you to enjoy our modern, 1,400-square-foot, two-bedroom, two-bathroom condo, which has been completely renovated. This condo is one of the nicest in the complex. Music is available in every room, including the master bathroom. We’ve thought of everything, including flat-screen TVs in both the master bathroom and the kitchen. You can relax on the forty-foot balcony while watching the ocean and using the free Wi-Fi. This will truly feel like your second home.brbrKey West offers a wide array of activities for everyone. You'll find so much to do that you'll have no choice but to return to our Island Paradise.brbrExplore many excellent restaurants, enjoy talented musicians, listen to live bands, and visit famous museums, from Mel Fisher to Ernest Hemingway. You can fish, dive, jet ski, or simply relax on the beach and unwind. Don’t miss our famous sunset celebration! For local knowledge and advice, give us a call—we'd be happy to share our island secrets with you.

Bed

Bath

Sleeps

$276.95

/ Nightly

Private Vacation Home

~ THE PINK HOUSE ~ Saline pool, lush privacy and 2 ensuites with balconies.

Key West, Florida, United States

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: Enjoy beverages on the balconies or a splash in the pool, as you being to unwind and enjoy your vacation. Filled with sunshine and happiness, this two-story pink gem provides space and privacy for families or friends. brbrWith two first floor living rooms, two ensuite bedrooms and two private balconies, everyone can enjoy their own slice of heaven. When it’s time to come together, the open concept gourmet kitchen and seating areas on the first floor, provide room for entertaining. Complete with a sleeper sofa, TV, dining table, and bar seating, the comfortable kitchen area allows everyone to be in the conversation. The chef in your group will enjoy preparing gourmet treats in the beautifully equipped kitchen with white cabinets, granite countertops, stainless steel appliances and a slide-in gas range. brbrFrench doors open out onto the back deck and cocktail pool, and exemplify indoor-outdoor Key West living. It is here that you will make wonderful memories. Rounding out the first floor is a convenient powder room, cool tile floors and a desk, should you or the kiddos need to get a bit of work done. The Pink House is indeed a classic treasure not to be missed! brbrBED CONFIGURATION: Two light and airy queen ensuite bedrooms are located on the second floor. Adorned in colors of the sea, each room has a beautifully updated bath, TV, ceiling fan, dresser, and French doors that access your own private balcony-one in the front of the home and one at the rear of the home. A sleeper sofa is available for a guest.brbrOUTDOOR AMENITIES: Private saline cocktail pool with a small sitting pool surrounded by lush foliage. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Lounge chairs, an outdoor shower, deck, gas grill and dining table are provided for your enjoyment. brbrPARKING: A luxury in Key West, this home includes parking for 2 vehicles. brbrLOCATION: Ideally located just 3 blocks from Duval Street and north of Truman Avenue in Historic Old Town. From here you can walk or bike to several galleries, attractions, and restaurants. brbrPETS: This home is NOT pet-friendly. (If you have pets, please browse through our many homes that are pet-friendly.)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***Please note that the cleaning fee includes a full mid-stay clean***brbr**Managed by Historic Key West Vacation Rentals**

Bed

Bath

Sleeps

$241.72

/ Nightly

Private Vacation Home

~ CASABLANCA ~ Fabulous home w/ private pool/parking, in a quiet location.

Key West, Florida, United States

THE PROPERTY: Between the welcoming front porch and the private pool, you will be sure to enjoy fresh air and sunshine during your stay. This unpretentious home is comfortably furnished and ready to welcome you and your fur baby. The living room looks out to the covered front porch and has lots of natural light. Wall AC, TV, a queen sleeper sofa, and a work desk may be found in the living room. Solid surface floors adorn the home and make it easy to keep clean. The cozy kitchen is complete with all that you need to prepare meals or snacks. The dining area is located just outside the kitchen and has table seating for four. The spacious king bedroom includes an ensuite bath with pedestal sink and tiled walk in shower with glass door. It also has 2 nightstands, TV, wall AC and French doors that lead out to your 20’x10’ private pool. Wake up and start your day with coffee and a swim. Take your bike or walk to Duval Street and enjoy all the excitement that make Key West unique. When you are done for the day, come home to relax and unwind in your private pool in a peaceful part of town. brbrIf you are vacationing with another couple or family, you may rent the other side of this duplex, which sleeps two and has a private hot tub. Look up Casablanca Too to do this individually or look up Casablanca Grande” to rent both sides of this duplex home simultaneously.brbrBED CONFIGURATION: Wake up in the morning in your king sized bed. There is also a queen size sleeper sofa in the living room for guests. There is a cool wall AC in each room.brbrOUTDOOR AMENITIES: From your bedroom, you can open the French doors and step out to the backyard’s mature foliage and private pool. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. You will also enjoy the back deck with outdoor dining set and umbrella, gas grill and chaise lounge chairs. Your washer and dryer are in a shed off to the right of the patio.brbrPARKING: This home includes off street parking for one mid-size car. brbrLOCATION: Historic Old Town, North of Truman Avenue and close to The Meadows, a residential district. Walk to Duval Street in 15 minutes or take a 5-minute bike ride to Higgs Beach or the Southernmost Point. Fausto’s Food Palace, The Best Coffee in Town, Bayview Park, and the Key West Cemetery are also just a short walk away.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***Staying for a month or longer Request a quote for a minimum of 28 nights to see our discounted monthly rates.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

Bed

Bath

Sleeps

$290.62

/ Nightly

Condo

Casa Coastal East – Morning Sunrises, Evening Vibes, Island Home in Key West

Key West, Florida, United States

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.brbrCasa Coastal East brStylish, Remodeled 2BR Condo with Oversized Balcony & Resort AmenitiesbrbrWelcome to Casa Coastal East, your tranquil island retreat at the exclusive 1800 Atlantic in Key West. This beautifully remodeled 2-bedroom, 2-bath condo features an open layout, brand-new kitchen and bath upgrades, and designer furnishings from Royal Furniture of Key West. Local artwork by renowned photographer Alan Maltz adds a unique and authentic island touch.brbrThe spacious master bedroom includes a king-size bed, while the guest bedroom features a queen bed and a built-in desk—ideal for remote work. A full sleeper sofa in the living room offers additional sleeping space. All rooms open onto a large private balcony where you can relax and enjoy the tropical breeze.brbrKey Features:br Remodeled kitchen and bathroomsbr King bed (master), queen bed (guest), and full sleeper sofabr Built-in workspace with high-speed Wi-Fibr Sliding glass doors to a private oversized balconybr Washer/dryer in unitbr Modern interior with local art and new furnishingsbrbrResort Amenities Include:br Olympic-size heated poolbr 20-person jacuzzibr Three tennis courts (one clay)br Tropical gardens & private sunbathing beachbr Secure parking and elevator accessbrbrLocated just minutes from downtown Key West and next to Smathers Beach, you’ll be close to museums, live music, water sports, restaurants, festivals, and more.brbrExperience the perfect blend of comfort, style, and island charm at Casa Coastal East – your home away from home in paradise.

2

Bed

2

Bath

4

Sleeps

$898.4

/ Nightly

Private Vacation Home

~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.

Key West, Florida, United States

THE PROPERTY: Nancy & Carl invite you to share their love of the island in their enchanted 3-bedroom home. Live like a local in this unique Key West property. Designed for relaxation and indoor-outdoor living, this home exudes local architecture, art, and joie de vivre. From its welcoming front porch to its private back yard, you will know from the start, that you are in a special place. brbrThe living room is comfortably furnished with plenty of seating for family and friends. From here you can open the expansive French doors and enjoy the patio area or take a dip in the cocktail pool. The kitchen is nearby and equipped with a gas range, stainless steel refrigerator, granite island and grey and white custom cabinets. You will find all that you need to entertain family and friends. If you are not dining at a local restaurant, you can opt for a meal at the handsome dining room table or dine al fresco, just outside the kitchen door; the choice is yours. A convenient half bath with stone vessel sink, washer and dryer and a folding counter, round out the first floor. The beautiful staircase at the front of the home will lead you to the bedrooms. If you are looking for the epitome of Key West, look no further than Southard Comfort! brbrBED CONFIGURATION: All three bedrooms are located on the second floor, have vaulted ceilings and are characteristically Key West. The primary bedroom with king bed includes a TV, dresser, ceiling fan, closet, and skylight as well as an ensuite bath with tiled shower and vessel sink. The second bedroom has a queen bed, nightstands, a dresser, closet, TV, and plenty of natural light. The third bedroom is also bright and includes a queen bed, dresser, closet, and TV. A shared Jack and Jill bath with access from the second and third bedrooms is adorned with louvered pocket doors, a tiled, walk-in glass shower as well as two separate vanities with granite countertops. brbrOUTDOOR AMENITIES: The cocktail pool with figurine water feature is located right off the living room to provide you with easy indoor-outdoor living. The pool is heated seasonally (November through April) or can be chilled during warmer months, for an additional fee which will be assessed at the time of booking (heater) or request for the chiller. Rinse off in the outdoor shower after a dip in the pool or a day at the beach. Enjoy outdoor dining on the patio area with umbrella table and chairs and gas grill.brbrPARKING: This home comes with your own private driveway with space to park one vehicle-a real Key West treat!brbrLOCATION: Old Town, North of Truman Ave, just 4 blocks to the Historic Seaport area and 6 blocks to the excitement of Duval Street. brbrPETS: This home is NOT pet-friendly. (If you have pets, please browse through our many homes that are pet-friendly).brSMOKING: 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***

Bed

Bath

Sleeps

$307.72

/ Nightly

Private Vacation Home

~ SEA VISTA ~ A waterfront dream with private heated pool and boat launch.

Key West, Florida, United States

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: Dreaming of putting your toes in the sand or sipping coffee on your dock Then this is the vacation home for you! The lush backyard is gated and leads out to the warm Gulf of Mexico. Just steps from the water’s edge, this unique paradise has a dock for your shallow-draft fishing boat. There are several outdoor areas of enjoyment including a dining table, loungers, and covered porch with comfortable furnishings. brbrIndoors, you will find a large living room with plentiful seating and a TV. Via large French doors, this room has views of the covered porch, pool area and sea. A bonus room/study with pocket doors and NEW twin beds is located near the living room. The dining area has ample table seating for 6. In the kitchen you will find everything you need to prepare meals or cook up your catch of the day. Stainless steel appliances, a slide-in range and solid surface countertops provide the conveniences of home. Peninsula seating allows you to socialize with your guests. The open-concept first floor is perfect for entertaining and embodies the indoor-outdoor Florida lifestyle. brbrThree bedrooms are located on the second floor and have their own TVs and ceiling fans. A primary king ensuite with soaking tub and walk-in shower offers a wide balcony and commanding water views. A queen bedroom and a full/double bedroom share a hall bath with a tub/shower combination as well as direct access to the treetop balcony.br brThis private paradise is a boater’s dream. Not a boater Then enjoy the pool, direct water access and breathtaking sunsets right from your backyard. Gulf Pointe’s Sea Vista embodies life on the turquoise waters of Key West. brbrBED CONFIGURATION: The primary ensuite bedroom has a king bed and balcony. Two additional bedrooms, one with a queen bed and one with a full/double bed, share a full bath and balcony. There are twin beds in the first-floor bonus room/study.brbrOUTDOOR AMENITIES: Just beyond the property’s fence and rarely available in rentals, there is dock access for a shallow draft, 21-foot maximum boat. Enjoy your private deck, outdoor shower, and stunning gulf views. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. A gas grill, outdoor dining table with umbrella and comfortable loungers complete your outdoor experience. brbrPARKING: There is a dedicated, covered parking spot for one car. brbrLOCATION: Midtown East in the gated community of Gulfview Pointe. Close to restaurants, retail shopping, and amenities. The energy of Duval Street, the magic of the Historic Seaport, and the beauty of the Atlantic Beaches are short bike rides away.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.***

Bed

Bath

Sleeps

$423.22

/ Nightly

Private Vacation Home

~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.

Key West, Florida, United States

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: As you enter the carport and begin to unwind, you will be greeted by beautiful porches and tropical greenery. Drop your luggage at the door and go for a swim. Around back, a private pool awaits you. Later, you can cozy up to a bedroom of your choice. brbrThe first-floor queen ensuite bedroom includes a desk, dresser, ceiling fan and access to the pool. The second floor is home to three additional bedrooms. The first is a king suite with TV, wet bar, and walk-in/walk-through closet with access to the washer/dryer. Its ensuite bath has a large soaking tub with a laminar flow filler that fills from the ceiling, and a spacious walk-in shower with multiple heads. The room also provides access to a private balcony. The second is a queen suite with nightstands, ceiling fan, TV, dresser, and glass doors leading to the sun deck. The third bedroom on the second floor includes twin beds that may be converted to a king. This bedroom accesses a full bath from the hallway. It also has access to the second-floor balcony in front of the home that overlooks Fleming Street. This balcony wraps around the side of the house and connects to the sun deck. Its spiral stairs will lead you down to the pool area. brbrBack downstairs you will pass the half bath on your way to the open concept great room. Here you will find sunshine, happiness and the home’s living room and kitchen. Stainless steel appliances, a triple sink, and granite counters round out the gourmet kitchen. The adjoining living room has a queen sleeper sofa, plenty of seating for your family and friends, a large screen TV, ceiling fans, and storage. From this area you will also find table seating for six, a wet bar with wine fridge, and access to the pool area via the expansive wall of windows. This home embodies the Key West lifestyle and is yours to enjoy while here on the island. brbrBED CONFIGURATION: This home has 4 beautifully appointed bedrooms. A queen ensuite bedroom is located on the first floor for those who may not prefer stairs. Three additional bedrooms are located on the second floor. They include one king ensuite, one queen ensuite and one twin bedroom. The twin beds may be converted to a king size bed and have access to a full bath in the hall. brbrOUTDOOR AMENITIES: A small sitting pool spills into the larger pool and will cool you down after a day exploring the island. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. There is a deck and outdoor dining area for al fresco meals. brbrPARKING: There is designated parking for 2 vehicles in the carport.brbrLOCATION: Old Town, North of Truman. Many tourist attractions are located here as well as restaurants, shops, and galleries. Just 5 blocks to Duval Street or the Marina and walkable for those who like to park their car and chill. The neighborhood boasts historic homes, shotgun, and conch style homes.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 not allowed.brbrSMOKING: This is a non-smoking home. brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Managed by Historic Key West Vacation Rentals***

4

Bed

4

Bath

8

Sleeps

$407.37

/ Nightly

Condo

Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts

Key West, Florida, United States

Tropical Luxury in Key West – 2-Bedroom, 2-Bath OasisbrbrWelcome to your beautifully decorated two-bedroom, two-bath retreat overlooking a lush tropical courtyard and garden. Recently renovated, the bathrooms offer modern comfort, with the master bath featuring both a luxurious tub and a walk-in shower.brbrThe spacious master bedroom includes a king-sized bed, while the guest room comfortably accommodates with a queen bed and a twin. For additional sleeping space, the living room features a queen sleeper sofa. Each of these rooms opens onto a large private balcony, perfect for enjoying peaceful island breezes.brbrRelax in the Olympic-sized heated pool or unwind in the spectacular Jacuzzi. 1800 Atlantic is also home to the only clay tennis court in Key West—ideal for tennis enthusiasts.brbrLocated just a 10-minute bike ride or a short walk from all of Key West’s top attractions, this property offers both convenience and serenity. Free secured parking is available for guests who choose to rent a car.brbrYou'll also enjoy high-speed internet and a dedicated workspace—perfect for blending work and leisure. And if you're looking for dining recommendations, we’d be happy to share our favorite world-renowned local restaurants.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Bed

Bath

Sleeps

$343.13

/ Nightly

Private Vacation Home

Cozy Piece of Key West History

Key West, Florida, United States

PERFECTLY located, 100 y-o Conch House, w AAA+ front-porch, and 3 full baths to go w 3 BRs... brand-new kitchen, completely renovated since 2015... outstanding back yard w gas grill.... house and yard are enclosed by barrier of FL palms, for privacy... 4 blocks from the historic and delicious Blue Heaven, where Hemingway boxed, and 4 blocks from his historic house.... this house is a great place to spend 30+ days in the best of The Sunshine State!

Bed

Bath

Sleeps

$278.81

/ Nightly

Private Vacation Home

~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!

Key West, Florida, United States

THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West charm and contemporary touches. To explore the second-floor home, search for “Poinciana Treetop,” or book “Poinciana Paradise” to reserve the entire home for family or friends.brbrWalkable to many shops and attractions, you will feel like a local in no time. Enjoy coffee or cocktails on your covered front porch. Prepare meals in the bright and snug kitchen with built in corner hutch, open shelving, and gas range. With so many local dining options, you won’t even mind being without a dishwasher. The open living area includes brand new mini-split AC, ceiling fan and comfy couch. The primary bedroom includes an ensuite bath, TV, nightstands, closet, brand new mini-split AC, and ceiling fan. Not to be missed is the bedroom access to the lush outdoor area. Sun yourself in the shared yard or take a jaunt to the beach. When the day is over, you may find yourself relaxing under the stars and enjoying conversation with friends. brbrBED CONFIGURATION: The king bedroom has an ensuite bathroom with a mini-split AC and tub/shower combination. There is a sleeper sofa in the living room for a child or guest. brbrOUTDOOR AMENITIES: Open the French doors from your bedroom and step out onto the first-floor porch. The backyard features a shared gas grill, washer and dryer, lush garden, back deck with chaise lounge chairs, and outdoor dining set. *Please note this property no longer has a hot tub.*brbrPARKING: There is on-site parking for one small car as well as a bicycle rack for your convenience. Please note this home is on a tiny one-way lane. brbrLOCATION: Historic Old Town, North of Truman and 2 blocks from the excitement of Duval Street. A majority of the best Key West attractions are located here as well as numerous restaurants, shops, and galleries. The neighborhood boasts historic homes, shotgun, and conch style homes. You will enjoy being right in the middle of everything!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***

Bed

Bath

Sleeps

$365.62

/ Nightly

Condo

Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach

Key West, Florida, United States

2 Bedroom, 2 Bath Garden View Condo – 1800 Atlantic, Key WestbrbrEscape to paradise in this beautifully renovated garden-view condo just steps from the Atlantic Ocean. Located in the highly sought-after 1800 Atlantic complex, this spacious 2-bedroom, 2-bath retreat offers comfort, luxury, and resort-style amenities.brbrBedrooms & Living SpacebrThe primary bedroom feature luxurious king bed and guest bedroom a King, while a commercial-grade sleeper sofa adds extra sleeping space in the living room. The open-concept living area is outfitted with Smart TVs throughout for your entertainment.brbrGourmet KitchenbrThe custom kitchen features granite countertops and modern appliances—perfect for dining in after a day of exploring.brbrAmenities & Featuresbrbr Assigned secure parking spacebr Three tennis courts, including one of the only clay courts in Key Westbr Five picnic pavilions with BBQ grillsbr Lush botanical courtyard with native trees and vibrant flowersbr Olympic-size heated pool with ocean viewsbr 20-person oceanfront hot tubbr On-site library for quiet momentsbr High-speed internet in the unit and courtyardbrbrLocationbrbr Situated directly on the Atlantic Oceanbr Adjacent to Smathers Beach—just a short walk br Only 1.5 miles from Historic Downtown Key WestbrbrWhether you’re exploring Duval Street, relaxing by the ocean, or taking sunset photos in the courtyard gardens, this condo is your perfect Key West home base.brbrPlease note: Minimum stay requirements may vary by season.brbrbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Bed

Bath

Sleeps

$273.32

/ Nightly

Condo

Sea La Vie, Elegant Key West 2BR/2BA | Renovated Condo at 1800 Atlantic

Key West, Florida, United States

Beautifully Renovated 2nd Floor Condo with Ocean & Preserve Views – 28-Day Minimum StaybrbrWelcome to your home away from home! This beautifully renovated 2nd-floor unit features luxurious finishes throughout and offers the perfect blend of comfort and style. Step out onto the expansive 40-foot private balcony, where both bedrooms and the living room open to stunning views of a serene nature preserve and the Atlantic Ocean.brbrThe condo is fully equipped with all the modern conveniences needed for a relaxing and enjoyable vacation, including high-speed Wi-Fi. Each of the two spacious bedrooms is outfitted with a King bed, and for added flexibility, the guest bedroom can be arranged with two Twin beds upon request.brbrThis is a non-smoking unit designed for your comfort and peace of mind.brbrLocated just a short walk or bike ride from the island’s top amenities, you’ll also be less than 1.5 miles from the historic district—home to renowned restaurants, charming shops, and vibrant nightlife. Whether you’re seeking adventure or tranquility, this location has something for everyone.brbrFeel free to call us or stop by for local tips and recommendations—we’re happy to share our favorite spots with you.brbrWe’re confident that once you stay here, you’ll want to return year after year.brbrPlease note: This property requires a minimum stay of 28 days.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

2

Bed

2

Bath

6

Sleeps

$1441.18

/ Nightly

Condo

Very Rare-The Galleon 3 King Bd, 3 Bath w/ 4th king bd in loft + sleeper sofa

Key West, Florida, United States

The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is spacious and very beautiful. The decor is everything you would desire in a Key West accommodation: tropical, clean lines and filled with every need possible.brbrThis Unit was built for the Developer and is unique with many extra features which includes a private sun-deck. It is a Penthouse Unit with 3 private bedrooms, an additional King bed in the loft and a queen pull-out sleeper sofa in the living room. brbrA full kitchen in the main unit and a small efficiency kitchen in the lock-out unit. The over sized balcony which streches the width of the entire unit gives you a panoramic view of the yachts, ocean and tarpon swimming among the floating docks below. The amenities are varied making family needs ideal from fishing off the dock to catch dinner, sunbathing by the pool, treasure hunting on the beach, jet skiing to a near by island, taking a short 5 minute drive to Play Key West Goldf Club (A Reese Jones Design) or chartering a boat for a day of fishing.brbrbrThe Resort: The Galleon Resort has it all ! Whether you just need to rent the efficiency (see our other add) or the two or three bedroom this is much cheaper than going to any of the 5 Hotels in the Marina/Malory Sq Area.. Go for the Resort Lifestyle!

Bed

Bath

Sleeps

$300.14

/ Nightly

Private Vacation Home

~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.

Key West, Florida, United States

THE PROPERTY: This one bedroom, one bath, first-floor duplex is conveniently located in Old Town. Walkable to so many Key West activities, you won’t need a car, just a pair of sandals or a bicycle. Tucked down a quiet one-way lane, this casual home is comfortably furnished. It sits just a block and a half from Duval Street yet it’s oh so tranquil. As you enter the front door from your covered porch, you will be welcomed by natural light, sunny walls, and Florida furnishings. The living room opens to the dining area that leads to the kitchen. The living room houses a sofa, chair, split unit AC and a large screen TV. Open to the dining area, you will find table seating for four and eclectic splashes of art. The kitchen includes a full-size refrigerator, dishwasher, gas range, microwave and all the tools necessary to cook meals or prepare snacks. brbrThe bedroom is located off the living room. It’s soothing white walls are peppered with art. The room is cozy and comfortable, and includes dresser storage, a reading chair, bedside lamps, and a ceiling fan. A garment rack provides easy access to your clothing. You can enter the lushly landscaped, shared outdoor space from your bedroom. The snug bathroom with a tub/shower combination is more than adequate for rinsing off after a day in the sunshine. Homey and low-key, Solaris Cottage is a unique place to enjoy a laid-back vacation on beautiful Key West. brbrSOLARIS COTTAGE occupies the front section of this first-floor duplex home. SOLARIS GARDEN occupies the back section of this duplex home. For information on renting both parts of this duplex, please see SOLARIS PAIR-A-DISE. brbrBED CONFIGURATION: The queen bedroom is furnished with a dresser for storage, a ceiling fan and reading chair. brbrOUTDOOR AMENITIES: Open the doors from your bedroom and step out to the shared side deck under a giant Banyan tree. Step outside the kitchen door and you will find the shared infrared grill as well as the shared outdoor washer and dryer.brbrPARKING: There is no designated parking for this rental, however, there is usually parking available on nearby Petronia and Angela Streets. To avoid a parking ticket, please be sure that you don’t park in a spot labeled residential, as these are assigned to full-time residents.br brLOCATION: The property is on a tiny, one-way lane in Old Town, North of Truman Avenue and just a block and a half from Duval Street. Leave your car at home because you are just a short walk or bike ride to many tourist attractions, bars, restaurants, shops, and galleries including Mallory Square, known for breathtaking sunsets and performers. 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***

1

Bed

1

Bath

2

Sleeps

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