Vacation Rentals By Owner In Key West, FL

Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval Street. Stay in a traditional Conch Style Home that features Mexican tile floors, spacious master bedroom with queen size bed, guest bedroom with full size bed and one couch sleeper sofa. Two full size bathrooms and inside washer/dryer. Central air conditioning, flat screen tv's and free wifi and open style full kitchen and living room. Pool on property. There is an additional cottages for rent upon availability. Vrbo #481491. Free off street parking spot. Cottage is popular with many repeat renters so reserving sooner than later is recommended.

Cottage

Conch Republic Consul General's Cottage.-Historic District

Key West, Florida, United States

Bed

Bath

Sleeps

$360.8

This condo has been grandfathered in to allow for weekly rentals. One of only a few with City approval. This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in the Truman Annex, a gated community of private homes and condominiums. Located inside the Truman Annex is Truman's Little White House Museum, Eco-Discovery Center, Water Park for small children and Fort Zachary State Park. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin beds that are easily converted to a king sleeper, a sofa sleeper, full kitchen, living room, washer/dryer and two private balconies one overlooking the swimming pool and the other facing the courtyard. Free assigned parking spot and Free Wi-fi. Steps from famous Duval Street, sunset celebration and all the downtown action one desires. High demand book early.

Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$533.25

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions. brbrTwo of the Queen bedrooms share an en-suite bath easily assessable from either bedroom. It features a very large walk-in shower. The 3rd bedroom features a full sized bed, walk in shower and private entrance. The quaint living room has a new L Shaped Sofa that provides plenty of additional sitting room for kicking back and chill time.brbrEach bedroom and the living room are equipped with brand new HIDEF Samsung 4K Smart TV’s. In addition, we have recently upgraded the cottage to include FREE 300 Mbps ATT Hi Speed Business Internet, new orthopedic mattresses, and cozy linens – towels to make your stay relaxed and pleasant. There is also a brand new Central Air Conditioning system to help keep you comfortable and snug, especially during the warmer summer months!brbrAdjacent is a completely equipped kitchen that has granite counter tops, glass cooktop stove, microwave and refrigerator. Even wine and champagne glasses are included! A bicycle lock-up in the courtyard is available.brbrBlocks from the marina district, and an easy walk (.7 miles) to Ft. Zachary Taylor where Australian Pines tower over the beach. There is on street parking available (Hemmingway House .28 miles, Duval Street 1 block, Marina District 7 blocks, beach .7 miles).brbrThere is a health food store located directly across the street called 'The Sugar Apple' which serves fresh fruit smoothies, lunch, and offers a variety of health food. A CVS is located one block away. A bike and scooter rental location is one block away. brbrA 3-night minimum stay required and strict No Smoking policy applies. Please contact owner for exception to 3 night minimumbrbrPlease note rates are subject to change and are higher during Event Periods such as Fantasy Fest, Gay Pride, Memorial Day, Christmas Week, New Year's Week, Thanksgiving, etc. Longer stays than 3 days may be required during event periods.brbrNOTE: There is No Dedicated Parking included with this rental. Directly on Simonton Street are (4) spaces and available on first come basis. We do recommend keeping the car parked and walk, bike or use the bus service, The Duval Loop. The Duval Loop provides FREE Hop on, Hop off bus service, operates every day, and stops a half block from the cottage. https://www.cityofkeywest-fl.gov/326/Duval-LoopbrbrIMPORTANT: We strongly recommend purchasing travel insurance to protect against illness, medical emergencies, weather-related issues, or other unexpected circumstances. While travel insurance can be purchased during the booking process, you may want to consider other reputable travel insurance providers, such as Travel Guard (AIG), Nationwide, Allianz, Berkshire Hathaway and Red Sky. We encourage you to review their coverage options and rates to find the best fit for your needs.brbrFor those traveling during Florida's hurricane season (June 1 – November 30), travel insurance is especially important. Please note that NO refunds will be issued for weather-related disruptions or early departures.

Cottage

The Dancing Rooster: 2 Blocks from Duval in Old Town.

Key West, Florida, United States

Bed

Bath

Sleeps

$493.63

ALLOW THE PERFECT VACATION TO UNFOLD...brThe epitome of laid-back, island living is found within this classic, Conch style home bringing endless charm to your tropical vacation. Steps from high end galleries, bars and restaurants, yet tucked away on a quaint and colorful lane, this home entails all the desired amenities that will truly immerse you into the Key West spirit. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES...brA friendly front porch awaits your morning cup of coffee, so you can plan out your day while you gaze beyond at tropical surroundings and neighbors passing by. Inside you will find an inviting space with cozy furnishings and a flat screen TV to gather around on a lazy afternoon. A fully equipped kitchen is accompanied by an indoor dining area and bar seating to enjoy meals together. Perch the French doors open to bring the breezy outdoors inside. YouTube TV is offered so you can stream your favorite shows. brbrSLEEPING ARRANGEMENTS...brThis newly renovated gem totals 2 king bedrooms and two en suite bathrooms - one with a shower and the other with a shower/tub combination. Each room is equipped with a cozy kings bed and a flat screen TV. A queen sofa sleeper allows for additional sleeping arrangements in the living room. brbrOUTDOOR LIVING...brEscape reality and explore this extraordinary hideaway! Your own private, lush backyard oasis is the perfect setting for your tranquil escape from reality. Complete with outdoor dining, a gas grill and peaceful surroundings for unwinding under the stars, this backyard dream immerses you into your island home away from home. brbrPARKING...brAlthough just steps to all the action, this home comes with 1 off street parking space making coming and going a breeze. brbrPETS...brDogs are considered but no cats permitted and a pet fee is required. brbrDISTANCES TO BEACHES...brSouth Beach is 0.2 mibrHiggs Beach is 0.8 mibrSmathers Beach is 2 mibrFort Zachary Taylor Beach Is 1.4 mibrAll beaches have beach chair and umbrella rentals.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 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrCREATE YOUR ISLAND STORY...

ISLAND DAZE ~ Adorable 2 Bedroom, 2 Bathroom Cottage 1/2 block to Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$238.85

Escape to the vibrant heart of Key West and stay at the charming Claude Monet Suite, located just a few blocks from famous Duval Street. This micro-efficiency studio offers a cozy retreat for up to four guests, with access to a tranquil pool and spacious sundeck. Once a creative hub for traveling artists, The Galleria has now been transformed into a relaxing oasis for visitors looking to unwind and soak in the unique charm of Key West.brbrThe Ambiance:brPerfect for couples or small groups, the Claude Monet Suite features a comfy Queen bed and a newly installed full-size sleeper sofa. After a day of beachcombing or sightseeing, relax on the cozy two-seater couch while enjoying cable TV or streaming your favorite shows with free WiFi. The kitchenette is equipped with everything you need to prepare light meals or snacks, including a microwave, mini fridge, basic kitchen utensils, and a Keurig coffee maker. Start your mornings with breakfast before heading out to explore all that Key West has to offer.brbrGuest Access:brEnjoy a seamless stay with our easy, contactless check-in process. Guests will receive two personalized access codes for both the hallway and the room, ensuring quick and convenient entry. As a guest of the Claude Monet Suite, you'll have access to the heated pool, sundeck, on-site laundry facilities, bike rack, and a gas grill, perfect for a laid-back barbecue in the sunshine.brbrThe Neighborhood:brLocated in the heart of Bahama Village, this studio places you in one of Key West's most historic and colorful neighborhoods. Just a short walk or bike ride will take you to the iconic Southernmost Point, Hemingway House, and the Key West Lighthouse. You'll also be steps away from the best local dining spots, like Blue Heaven, Santiago's Bodega, and Firefly, offering a true taste of island life. Whether you're here for culture, history, or nightlife, you'll find it all within easy reach.brbrGetting Around:brWhile on-site parking is not available, free limited street parking can be found on a first-come, first-served basis near the Galleria complex. Key West is highly walkable, and many attractions are just minutes away. If you prefer, you can rent a bike, scooter, moke, or golf cart to explore the island. Uber, Lyft, and local taxi services are also readily available. Need advice on transportation Feel free to ask us for recommendations!brbrOther Things to Note:br- Please keep in mind that this unit is cozy and may feel small for some guests, but it offers everything you need for a comfortable stay - 254 sqft. br- We've recently added a new pullout couch for extra comfort, making it a great option for additional guests.br- There's also a shared washer and dryer located on the first floor, right next to the pool area. br- Pets are welcome! We allow up to two pets, with a 40lb weight limit per pet, for a fee of $20/pet per night.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, driveways, pool, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Apartment

Claude Monet Suite | Cozy Studio with Pool & Patio

Key West, Florida, United States

Bed

Bath

4

Sleeps

$956.25

Make yourself at home in this 3-bedroom Key West house. The enchanting space features a king bed, queen bed, and twin bed, perfect for families or groups. Two bathrooms with refreshing showers add convenience to your stay. Guests enjoy a welcoming atmosphere with heating and air conditioning to keep things comfortable year-round. Fenced backyard, corner lot and plenty of parking. One block from Atlantic Blvd and short walk to the beach. Whether you’re relaxing indoors or exploring nearby, this fantastic house offers a cozy retreat. It’s easy to see why you’ll be able to unwind at our place.

Tranquil tropical 3-bedroom house with AC in vibrant Key West.

Key West, Florida, United States

Bed

Bath

Sleeps

$524.19

Summary:brbrWelcome to The Watson House, a historic gem at 522 Simonton Street, where old-world luxury seamlessly blends with modern elegance in Old Town Key West. This expansive two-story, 4-bedroom, 4.5-bath retreat is ideally situated just steps from Duval Street and the iconic Conch Harbor. The main-floor master suite boasts a king bed and luxurious ensuite bath. The spacious living room and additional seating area lead into an open-plan kitchen and living space, seamlessly extending to the outdoor terrace through 20-foot retractable glass doors. The gourmet chef’s kitchen is equipped with top-of-the-line appliances. Upstairs, you’ll find three more ensuite bedrooms: one with a queen bed, another with a full bed, and a kids’ room offering a queen bed and bunk bed. Assigned parking is a valuable bonus. Outside, indulge in the outdoor kitchen with a built-in grill, and unwind in the pool, illuminated by LED lights, or relax in the jacuzzi. This is Key West living at its finest!brbrbrbrThe Space:brbrThe Watson House offers a spacious, historic home with four bedrooms and 4.5 bathrooms. The main floor features a master suite, large living and seating areas, and an open kitchen with retractable glass doors leading to an outdoor terrace. Upstairs, three ensuite bedrooms include a mix of queen, full, and bunk beds. The property boasts a gourmet kitchen, assigned parking, an outdoor grill, a pool with LED lights, and a relaxing jacuzzi.brbrbrbrGuest Access:brbrPrivate Entry Key will be available when check in.brbrbrbrThe Neighborhood:brbrLocated in the heart of Old Town Key West, the Watson House at 522 Simonton Street sits in one of the most desirable and walkable neighborhoods on the island. Just steps from world-famous Duval Street, guests are surrounded by the vibrant culture, restaurants, art galleries, and nightlife that make Key West so iconic.brbrbrbrThe home is also a short stroll to the historic waterfront at Conch Harbor Marina, where you can enjoy boating, fishing charters, waterfront dining, and beautiful sunset views. Nearby you'll also find charming cafés, boutique shops, historic landmarks, and the island’s best beaches and parks.brbrbrbrDespite being in the center of everything, the surrounding streets maintain the classic charm of Old Town with colorful conch houses, lush tropical landscaping, and a relaxed island atmosphere. Guests can easily explore the area by foot, bicycle, or golf cart, making this location perfect for experiencing the very best of Key West. brbrbrbrGetting Around:brbrMost visitors get around Old Town Key West by walking, biking, or using golf carts, as everything is close by. Taxis, rideshares, and the Duval Loop shuttle are also convenient options for exploring the island. brbrbrbrInteraction with Guests:brbrPlease call Hana, the property manage

Luxury Residence in Old Town Key West w Pool

Key West, Florida, United States

4

Bed

Bath

10

Sleeps

$158.86

Key West Happy Hideaway is exactly that! Your perfect little hideaway nestled in the beautiful and lush landscaping of the highly sought-after Key West Golf Club neighborhood! Enjoy living the island lifestyle in this charming newly renovated in Fall 2024 town home with two bedrooms, one an half bathrooms, and 4 outdoor areas! There are two balconies with seating on the front of the house and two screened porches on the back of the back of the house!brbrAs you step into the villa, you'll be greeted by a bright and open living space that includes the kitchen, dining and living areas! The dining area has a table for four and the living room features a sleeper sofa, two comfortable chairs (one with a leg rest) and a flat-screen TV. The half bath is located in this area. Sliding glass doors open onto the covered screened patio that has a plush couch and a dining table with two comfy wicker chairs with seat cushions. The patio has a private cozy feel because of all the beautiful landscaping - no golfers on the course glancing onto the property, and you won't get golf balls flying into the house.brbrJust off the screened porch is the fenced back yard area with a brand new Webber grill! Steps outside fence and around the landscaping to a delightful little pond. Have a seat on the bench and enjoy peaceful moments listing to the water fountain and enjoying the view! Just a few steps from the property is one of the two community pools! So convenient!brbrThe fully equipped kitchen has new appliances and everything you need to enjoy cooking delicious meals during your stay. Additionally, there is a staced washer and dryer in the unit. We provide all linens, bath and pool/beach towels, two beach chairs, a beach bag and a small cooler.brbrBoth bedrooms are located on the second floor as well as the full bathroom with a large shower. The master bedroom has a queen size bed, ample closet space and a private screened balcony with two comfortable chairs with pull-out leg rests. The perfect spot for reading, napping, coffee, an evening cocktail or glass of wine! The second bedroom has a full size bed, some closet space, the washer and dryer and it's own balcony with seating. brbrAs a guest of the Key West Golf Club, you'll have access to a range of amenities at no extra charge! The community features 24-hour security, a Rees Jones designed golf course, two large pools, and a fitness center in the clubhouse. Whether you want to work out, swim, walk or play a round of golf, you'll have plenty of fun and healthy options! The beaches are less than 10 minutes away or you can ride bikes along the ocean on the wide sidewalk!brbrAs you likely already know, Key West has near endless option for dining, musis, adventures and entertainment! The Tennessee Williams Fine Art Center, Lower Keys Medical Center, Key West Tropical Forest and Botanical Garden are right in the neighborhood! Old Town Key West, the beaches, marinas, grocery stores, pharmacies are a short drive or even a bike ride away! Stock Island, just across US1 has fantastic dining options, too (The famous Hog Fish Grill, The Docks (my fav) Hurricane Hole, Matt's Stock Island Kitchen and Bad Boy Taqueria at The beautiful Perry Hotel, Roostica and El Siboney)brbrThis property must be rented for 28 or more required by The City of Key West.

Key West Happy Hideaway! Beautifully Renovated! 2 BDR/1.5 BA, GOLF, POOL, GYM

Key West, Florida, United States

Bed

Bath

Sleeps

$732.8

This charming getaway in the prestigious Porter Court is located in the award winning Truman Annex in Old Town Key West. Beautifully appointed with relaxation and fun in mind, this property has recently been updated. The master bedroom features a king bed and a twin. The second bedroom overlooking the pool includes a private deck, a queen sized bed, and an en suite full bathroom. The first floor includes a washer and dryer and a powder room. There are 19 town homes nestled around a central crystal blue pool. We like to call this the 'gated community within a gated community' as this compound has security gates for access. It's the perfect spot to decompress and let life's worries slip away, and enjoy your own little piece of paradise. There is assigned parking and quick & easy access to Duval/Old Town/nightlife/restaurants/beaches and water activities. brPlease note: This property is monthly rental - the minimum rental period is 29 nights/30 days, except for February, which is 28 nights!!!

Porter Paradise at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$358.74

This charming two bedroom, two and one half bath town home has recently been updated and added to our rental program!brFreshly painted and refurnished, this adorable property is located very close to the pool & includes a lovely rear deck and gardens. The master bedroom has a king sized bed, convenient writing desk overlooking the pool and a private cocktail deck. The guest bedroom features a queen bed.brBoth bedrooms have beautifully appointed baths ensuite.brThis very quiet private location, in the historic Mills Place complex, enjoys a very large refreshing pool with both sunny and shady areas. Also included here is an assigned off-street parking space and several bike racks.brThe Truman Annex is an award-winning gated community located in the center of Old Town Key West.brbrPlease note: This property is monthly rental -This property has a 28 night minimum stay

An Island Retreat at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$276.13

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrFEATURES:brBedrooms: 2 (1 king, 1 queen, sofa sleeper recommended for children ONLY)brBathrooms: 2 brLocation: Sunrise SuitesbrSquare Feet: 772brParking: 2 parking spaces includedbrAmenities: Wifi, TVs, in-unit laundry, shared pool, close to beaches, private balconybrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Apartment

Sunrise 103-2BR/2BA condo near beaches with pool, parking, balcony

Key West, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

Welcome to Island Time Casa, your ultimate family-friendly retreat nestled in the heart of Key West’s prestigious Casa Marina district. This spacious condo boasts three beautifully-appointed bedrooms and three and a half modern bathrooms, accommodating up to ten guests with ease, making it the ideal choice for multi-family gatherings or multi-generational vacations. brbrExperience the charm of Key West with sunny porches and breezy balconies that are perfect spots for sipping morning coffee, enjoying leisurely family meals, or watching breathtaking island sunsets. Inside, you'll find a full kitchen equipped with all the essentials to cook up delicious meals, coupled with a cozy dining area that invites family and friends to gather around. brbrThe convenience of an in-unit laundry adds to the comfort, ensuring sandy towels and swimming suits are dealt with effortlessly. Step outside to enjoy the exclusive amenities such as a shimmering pool, tennis courts for the sport enthusiasts in the family, and a grill area for the quintessential vacation barbecue. brbrIsland Time Casa is suitably located within walking distance to all local attractions including the Southernmost Point, and the vibrant scenes of Duval Street. Leave your car behind in our free parking area and explore the neighborhood by foot or bike, embracing the laid-back island life. Take peaceful walks, build sandcastles on the beach, or simply soak in the salt air — every moment is a treasure at Island Time Casa. brbrThe property promises a blend of relaxation and accessibility, providing the perfect backdrop for creating lifelong family memories. Whether you’re here to unwind or explore, you're officially on Island Time.brbrPlease note: All cancellations are subject to a cancellation fee, which varies depending on the cost of your booking.

Island Time Casa – Modern Key West Oasis w/ Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$938.79

'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE LanebrbrThis home is a perfect example of WHY people come to Key West to stay for a month or more! Live the island lifestyle outside enjoying the front porch, the second floor balcony, and the side lounge area with cocktail pool.brbrThe weather in Key West is absolutely amazing and this home maximizes the indoor outdoor living experience Key West has to offer.brbrDid we mention the home is walking distance to everything Key West has to offer brbrThe perfect blend of Historic architecture and the casual beachy cottage feel will make you, your family, and your friends feel comfortable and pampered.brbrThe extra large square footage assures everyone their own private space while the living room and open concept living area allow everyone to come together.brbrSimply tell your friends and family to meet you at the corner of Southard Street and Love Lane, one of Key West’s premier Old Town addresses. This spectacular, three-story, historic and award-winning home has been fully renovated to meet the most discerning tastes. Dappled sunlight plays across the Dade County pine in the cool, comfortable, inviting interior spaces and brightens the touches of warm tropical colors in the high-end furnishings and finishes.brbrSouthard Love is a home made for family gatherings or a lazy season away with friends. Its first floor primary suite opens through French doors to the large front porch that suggests a cup of coffee and a good book while people watching along Southard. The first floor includes a gourmet kitchen, the primary bedroom and bath, a guest room and bath and expansive living areas for playing games, gathering with friends or simply curling up and enjoying a peaceful evening. brbrWalk through the French doors from the living area and the kitchen to a private deck and classic Key West cocktail pool, surrounded with lush landscaping and tall, artistic privacy fences. The deck and its pool are made for entertaining and star-gazing.brbrUpstairs on the second floor is the private alternate primary suite with soaring ceilings, beautiful windows and elegant primary bath with a walk-in shower. But, it’s the master suite hammock porch that will capture your imagination. Fitted with deep, comfortable hammocks, leave the set of 3 French doors opens to the perfect island breeze. Enjoy the privacy of the porch, in the perfect blend of indoor and outdoor living. This primary suite with its beautiful, unique and private indoor-outdoor spaces will convince you to return year after year.brbrThere is more to explore on the third floor. The large, light-filled room under the eaves could become a child’s hideaway or an adult’s getaway space. You have the option of two twin beds or join them together as a king bed, providing flexibility for your family or your guests.brbrSouthard Love with its four bedrooms, three bathrooms and multiple indoor-outdoor areas is a gracious family home that welcomes its guests from the moment they turn the key in the vibrant sunny, yellow front door. It is a home to be enjoyed, to be shared and to be loved. brbrSouthard Love is located perfectly for a long stay in Key West. Simply park your car and unlock your bike or scooter. It’s two blocks (.2 miles) to all that Duval Street has to offer and 4 blocks (.4 miles) the Historic Seaport. There’s the added advantage of the designated bike lane, which runs the length of Southard, making it a straight shot across Southard to the beaches at Fort Zachary Taylor State Park. Fausto’s grocery is close enough to walk and there are wonderful neighborhood restaurants just blocks away.

Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths

Key West, Florida, United States

4

Bed

Bath

7

Sleeps

$160.21

Escape to Your Private Key West Oasis – Steps from the Hemingway HousebrExperience the true island lifestyle in this charming, secluded cottage tucked away in the heart of Old Town. Perfect for couples or solo travelers, this hidden gem offers a peaceful sanctuary just blocks from the Southernmost Point and the world-famous Duval Street.brbrThe SpacebrYour private retreat features a bright living area, a beautifully designed sleeping loft, and a fully equipped kitchen for home-cooked meals. Relax on your inviting porch to catch the tropical breeze, or take a refreshing dip in the sparkling pool located just steps from your front door.brbrGuest AccessbrEnjoy effortless entry via private front and side access. For those exploring by bike, convenient parking is available at nearby street posts and racks.brbrImportant NotesbrTo maintain our serene environment, this is a strictly smoke-free property (indoors and out).brbrNote: This property requires a 28-day minimum stay—perfect for those looking to truly immerse themselves in the Key West community.

Cottage

Charming 1BR Cottage : Steps from Hemingway House & Old Town

Key West, Florida, United States

Bed

Bath

Sleeps

$450.91

This luxurious recently renovated condo features a wonderful contempory interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests only. Must be 25 and older.brbrThe spacebrOur place is good for couples, business travelers and families with kids.

Tropical Escape at Sunrise

Key West, Florida, United States

Bed

Bath

5

Sleeps

$504.78

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrIt is not so often that something new is built in Old Town, the historic district of Key West known for quintessential conch homes and walkable streets. But recently a spectacular development called Old Town Villas was constructed smack dab in the middle of Old Town. SEAPORT SENSATION is one of the newly built breathtaking townhomes at Old Town Villas that allows you to enjoy the luxury of brand-new construction in the prime location you've been searching for. Typically, a prime location comes with noise, but not with this newly constructed home - you cannot hear a sound from inside! Other benefits of renting SEAPORT SENSATION include:brbr** Three spacious bedrooms, each with an en suite bathroombrbr** A private elevator reaching ground floor to top floorbrbr** Access to the large community poolbrbrAlso included with your rental is Last Key Realty's Five Star Guest Services, known for providing memorable Key West vacations. You couldn't fathom a better vacation home to experience all that Old Town Key West has to offer.brbrTHE LOCATION...brbrOld Town Villas is a unique gated community just developed in a prime area of Old Town Key West. There are 20 townhomes with one large shared pool, all accessible by electronic gates to which you will have your own key. You'll be in the epicenter of Key West, just steps from local favorites like A&B Lobster, Sloppy Joe's, and Schooner Wharf. Ride bikes to Fort Zachary Taylor State Park Beach, just a half-mile down the road. While you won't need a car to get around, your private two-car garage provides off-street parking.brbrTHE COMMUNITY POOL...brbrSoak up the sun at the large Community Pool, located just steps away from your front door. There are chaise lounges surrounding the pool for your comfort and a large cabana with restrooms for your convenience.brbrTHE LIVING AREAS & KITCHEN...brbrUse the private elevator to access every level of this home without the use of stairs. The first living level features a sitting room, dining area, and a top of the line gourmet kitchen. The sitting room has a large flat screen SMART TV, comfortable seating options, and a balcony. The gourmet kitchen has beautiful granite countertops and is fully equipped with stainless steel appliances and all of the tools needed to prepare a meal from home.brbrHop in the elevator (or get your steps in using the stairs) and head up to the top floor where you'll find the main living area with soaring vaulted ceilings, a large flat screen SMART TV, and plenty of comfortable seating. This living room also includes a full wet bar, a convenient half bathroom, and a large outdoor terrace, complete with outdoor seating and dining.brbrTHE ACCOMMODATIONS...brbr** First Master Suite: Located on the Third Floor with a King bed and an en-suite bathroom with dual sinks, a garden tub, and a shower.brbr** Second Master Suite: Located on the Third Floor with a King bed and an en-suite bathroom with a large glass shower.brbr** Third Bedroom: Located on the Second Floor with Two Twins OR One King bed and an en-suite bathroom with a shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat & A/Cbr** Ceiling Fansbr** Flat Screen State-of-the Art HD TVs in all bedrooms and main living areabr** Fully Equipped Chef's Kitchen with Stainless Steel Appliancesbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Private Elevatorbr** Off-Street Parking in Private 2 Car GaragebrbrOther notes:brbr** In person welcome when possible, after hours check in availablebr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** This property will accommodate 8 adults

**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$495.3

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrIf you’re looking for a Florida Keys home that rivals the seaside homes found in ‘Coastal Living’ magazine, look no further! COASTAL LOVING is an inviting two-story private home that offers a relaxing vacation setting and comfortable accommodations. This easy living home combines a classic Key West design with the finest modern updates and conveniences. If you ever decide to pull yourself away, you'll find that you are in the very heart of Old Town - with the best restaurants, live entertainment and attractions all within minutes of your front door. In addition to a phenomenal location, this home also offers the following amenities:brbr+ Private Heated Poolbr+ Spacious Indoor & Outdoor Livingbr+ Covered Off-Street ParkingbrbrYour rental includes Last Key Realty’s renowned Five-Star Guest Services, known for making memorable Key West vacations. So leave the worries to us, kick back, relax, and enjoy the reality of living in the pages of Key West’s very own version of “Coastal Loving.”brbrTHE LOCATION...brbrCoastal Loving is situated in a prime location of Old Town Key West, just a quick walk or bike ride to all of the favorite spots of the Historic Seaport and Duval St. While the front of the house opens facing Eaton Street, the home itself and particularly the pool area are set back closer to a tiny lane where you will access your covered carport and your private entry gate. Boaters will enjoy the proximity to both Conch Harbor and Garrison Bight marinas, both just a few blocks away.brbrTHE LIVING AREA and KITCHEN...brbrIn true Old Town Key West fashion, this home features beautifully restored Dade County Pine walls and oak floors, with a crisp coastal style and fun local art splashed throughout. The spacious living area boasts a large flat screen TV and has plenty of comfortable seating options for the whole gang. Open to the living area is the fully-equipped kitchen, with high-end stainless-steel appliances and every tool needed to prepare a meal at home. A unique feature of this home is the back wall of sliding doors that, when open, creates a spacious indoor/outdoor living area and dining space.brbrTHE POOL AREA...brbrThe entire pool area is fully fenced and surrounded by lush tropical landscaping for maximum privacy. The private heated pool gets plenty of sun throughout the day, with comfortable lounging options on the pool’s deck. When you’ve had enough sun, escape to the covered patio or shaded cabana next to the pool. Other bonuses of the pool area include a propane BBQ grill and ample landscape lights, making it an ideal place for your group to gather both day and night.brbrTHE ACCOMMODATIONS...brbr+ Bedroom #1 – Located on the First Floor with Two Twins OR One King bed, a flat screen TV, and an en-suite bathroom with a walk-in shower.brbr+ Bedroom #2 – Located on the First Floor with a Queen bed, a flat screen TV, and an en-suite bathroom with a walk-in shower.brbr+ Bedroom #3 – Located on the First Floor with a Queen bed.brbr+ Master Suite – Located on the Second Floor with a King bed, a flat screen TV, a walk-in closet, and an en-suite bathroom with his and her sinks and a large shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr+ Washer & Dryer br+ Central Heat & A/C br+ Ceiling Fans Throughoutbr+ Flat Screen HD TVs in Living Room and Bedrooms br+ Fully-Equipped Kitchen br+ Basic Stock of Spices br+ Starter supply of paper products br+ Starter set of cleaning products br+ Linens and Towels provided br+ Wireless high-speed Internet access and full cable is included br+ Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr+ Fenced & Lushly Landscaped Backyard br+ Private Heated Pool br+ Propane BBQ Grill br+ Off-Street Covered Parking for 1 VehiclebrbrOther Notes:brbr+ In person welcome br+ All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br+ Additional interim cleanings available br+ This property will accommodate 8 adults br+ Small Dogs Only - Max of 2 pets and an additional fee of $200 per pet

**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...

Key West, Florida, United States

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Bath

Sleeps

$344.14

Eleanor's Place Key Wes is a renovated, elevated, and a charming 2 Bedroom 2 Bath cottage in the heart of Key West! brbrIt was featured on HGTV's Island Life!brbr**NOTE: FOR CONSECUTIVE MULTIPLE MONTHS BOOKINGS PLEASE SEND US A MESSAGE FOR A DISCOUNTED QUOTE!**brbrTHE PROPERTY: Eleanor's Place Key West has everything you might want on your monthly vacation to Key West.brbrLOCATION: The cottage is in historic Old Town Key West, just steps to Duval, beaches, restaurants, attractions, and an olympic size pool!brbrVIRTUAL TOURS: Search Eleanor's Place Key West Cottage Rental on youtube for virtual tours.brbrBED CONFIGURATION: Queen Bed on main floor with wall mounted TV - and King Bed in upstairs loft with ensuite bath. (Spare blowup mattress also available.)brbrLIVING SPACE: The living and dining room are open concept with large windows and ample light. The living room has a new sectional sofa, and the dining room has a table for four. The wall mounted TV can be angled to face either the living room or the dining room. brbrKITCHEN: The chef’s kitchen is spacious, includes a breakfast bar, stainless steel appliances including a dishwasher and convenient full size laundry machines. brbrBATHROOMS: There are two full bathrooms. One is located on the main floor and the other is an upstairs ensuite in the King loft bedroom. brbrOUTDOOR SPACE: The house features a beautifully lush side yard with an inviting patio, made from reclaimed bricks. Enjoy comfortable patio seating, barbecue, and overhead lighting under the stars. brbrPARKING: Side driveway and street parking.brbrCLEANING: The cottage is professionally cleaned prior to each check-in. We kindly ask guests to clean their linens prior to checking out. We also have a monthly gardening service. brbrREVIEWS: Sadly the only review we've received from this platform was our first and only less than 5 star review - the review expressed disappointment in the comfort of the living room furniture, which has since been replaced. The furniture in question was temporary as it was all we could get at the time we purchased during the pandemic - this sofa has since been replaced by a comfortable sectional sofa as seen in the new photos.brbrAs many of our guests are repeat or booked privately or through other platforms, our other five star reviews are not visible here. However you can read more reviews on Google by searching Eleanor's Place Key West. The AI Summary of our ALL 5-Star Google reviews is Eleanor’s Place, a renovated historic cottage in the heart of Key West’s Old Town, is highly rated for its modern amenities, 5-star cleanliness, and pet-friendly, two-bedroom, two-bathroom setup. Located near Duval Street, the property is frequently praised for its convenient location and fully equipped, comfortable living spaces. brbrThank you for your understanding. brbrPETS: This home is dog-friendly. Some restrictions apply. brbrNOTES: br***Due to Key West Bylaws, a minimum stay of 28 nights is required. Guests check in on the 1st of each month. To book more than one month in a row and enjoy discounted pricing, please contact us.***

Eleanor's Place Key West - Dog Friendly in Old Town Key West

Key West, Florida, United States

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Bath

Sleeps

$621.85

Discover this 3-bedroom gem in Key West. This tranquil townhome offers a wonderful escape for guests. With 1 king bed and 2 queen beds, everyone will feel welcomed in this cozy space. Enjoy the convenience of AC, WiFi, and a washing machine during your stay. Relax in the fitness room or unwind in one of the 3 bathrooms equipped with a shower and bathtub. Enjoy your time in Key West at our townhome. 2 parking spaces under the house

Funky Chicken Cottage with shared pool, 3 bed 3 bath minutes from Key West

Key West, Florida, United States

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Bath