Vacation Home Rentals By Owner In Key West, FL

Welcome to Casa Del Sol, a colorful and effortless island stay! From the moment you step in the front door, you will take notice of the open-concept layout, bohemian furnishings, and lovely tropical theme. The living room's oversized sofa and large Smart TV offer the perfect combination for family hangouts. The adjacent full kitchen boasts a turquoise backsplash, stainless steel appliances, and granite countertops. After you whip up delicious dishes in this space, dine as a family around the wooden dining table. brbrEqually bright and beautiful, the home's bedrooms come adorned with high-quality linens, tasteful artwork, and TVs. Additional interior perks include a private washer/dryer, central air-conditioning, and a collection of board games. brbrOutside, enjoy the fresh sea breeze from the front porch or on the patio. Being nestled in a prime location, Key West's many amusements are at your fingertips! Get out and explore Hemingway Home and Museum, Key West Butterfly and Nature Conservatory, Smathers Beach, Florida Keys Eco-Discovery Center, and Fort Zachary Taylor Historic State Park. brbrThings to KnowbrCheck-in time: 4:00 PM.brCheck-out time: 10:00 AM.brAll guests shall abide by the good neighborpolicy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.brNo smoking is permitted anywhere on the premises.

Bohemian island home full of color and modern amenities - in a great location

Key West, Florida, United States

Bed

Bath

Sleeps

$561.45

Experience the very best of Key West living at this unique Old Town Truman Avenue Eyebrow home. Tucked away in a small, gated community, this luxury two-bedroom retreat showcases tranquil tropical decor and comes well-appointed with all the modern essentials of home. Whether you're visiting with the kids or sneaking away for a romantic couple's escape, you're sure to find everything you need for carefree vacation comfort. Prepare anything from morning coffee to full family dinners in the well-equipped kitchen and dine together at the nearby table. The private deck comes furnished with a gas grill and outdoor dining table if you want to enjoy some fresh Florida breeze with your meal. You can also bust out your favorite board games or settle outside on the large front porch and get some fresh Florida air. Enjoy access to a heated outdoor pool - the ideal place to unwind after exciting days out. In the evenings, relax in the airy living area while streaming shows and movies on the smart TV.brTHINGS TO KNOW:brEnjoy central walkability with Southern Most Point, the Lighthouse, the Key West Butterfly and Nature Conservatory, and the Ernest Hemingway Home and Museum, all within blocks from home. Experience unforgettable live entertainment and explore local galleries, shops, bars, and restaurants along Duval Street, just a short walk from home. Additionally, Fort Zachary Taylor State Park is only a mile west, where you'll find historic sites, beaches, and walking trails.brThis property is managed by Seven Keys Vacations by Casago.

Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining

Key West, Florida, United States

Bed

Bath

Sleeps

$487.06

Enjoy modern Key West vibes with this home's bright accent colors, eye-catching tile work, and of course the sparkling private pools! Make no mistake, there are two heated saltwater pools that you're free to enjoy all throughout your stay, both surrounded by lush greenery. Rinse off in the outdoor shower if you're coming back from the beach! This single-level home is a duplex with two different sections, so the group can spread out and enjoy their own space or just enjoy double the amenities. Open up the wide glass sliding doors and enjoy seamless indoor/outdoor living with plenty of seating options (including poolside!).brbrBoth full kitchens are stocked with equipment so that you can cook up something delicious, and each flows perfectly with their living room and outdoor relaxation areas. Don't worry, there's enough dishes, glassware, and cutlery to help you enjoy those meals. Central air conditioning will keep everything mellow. Throughout the house, guests can rest in bright bedrooms with unique art and quilt-style bedding that definitely shows off the Key West spirit. The bathrooms feature tile work that's just as stunning as the kitchen's - each standalone shower features intricate tile work on the floor and wall. Selfie-friendly ambient light mirrors will help you start off the day with a sunny disposition. Luxury amenities pair up with bright, eye-catching details in this vacation home!brbrWhat's nearby:brIf you're looking to head straight to the beach, Higgs Beach is just half a mile away. The Southernmost Point of the continental United States is just over a half-mile away - take a picture and then enjoy some conch fritters at the Southernmost Beach Cafe. Take in a bit of history at the Ernest Hemingway Home and Museum just under one mile from the home. But if you're looking for a different kind of escape less than one mile away, take a walk through a sanctuary of colorful birds and over 50 species of butterflies at the Key West Butterfly & Nature Conservatory.brbrThings to know:brFour twin beds are pushed together to make two king-sized beds in the photosbrSnowbird-friendlybrLuggage dropoff allowedbrGuests must stay for a minimum of 28 nightsbrBeach towels are available for guest usebrStep-free access to common areabr*Island Retreat and Island Hideaway are smaller properties within Tropical Vibes, each with their own private pool. They can be rented separately or together.brThis property is managed by Seven Keys Vacations by Casago.

Bright Key West House with Private Pool, Gas Grill, W/D, Central AC, & Free WiFi

Key West, Florida, United States

Bed

Bath

Sleeps

$983.71

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.*brbrThis four-bedroom Key West home has just what you need for an awe-inspiring Florida beach getaway, including a private heated pool, rooftop patio with a fantastic ocean view, and easy access to the beach and major attractions.brbrYou'll be a few steps from Southernmost Point, and you can walk to Key West Butterfly Garden, Key West Light House, and Southernmost Mansion, and Fort Zachary Taylor State Park is only a mile away. Famous Duval Street is also a short walk away, full of stellar restaurants and shops.brbrThe home's interior is spacious with interesting decor, and you'll have free WiFi, flatscreen cable TVs, a private washer/dryer, and private parking. There is a grill on the poolside patio, and an amazing rooftop patio, fully furnished for the absolute enjoyment of panoramic views of the ocean, sunrise, and sunset. brbrBook this gem today and ensure the best Florida vacation you can imagine!brbr*Please contact us for our special Snowbird rates!brbrThis property is managed by Seven Keys Vacations by Casago.

Fresh Getaway w/ Private Pool & Rooftop Patio - Great Location, Steps from Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$1101.38

Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher shop, this charming building has a rich and captivating history. In the 1930s, while Hemingway was living a few houses down, it was home to a popular Cuban bodega. From the 1980s through the turn of this century, potter Charles Pearson created ceramic masterpieces which are still collected today. If you keep a watchful eye, you will find some of his ceramic fish adorning buildings and homes in the neighborhood still. brbrIts current guardians have spent nearly a decade painstakingly bringing the building back to life, with Dog Tired Studio gallery up front as the proud face of the building. Julia Whitehead, the patron mermaid of the building, has been keeping an eye over this landmark since she first surfaced here in the 1800s, and she invites you to come and live like a local, just steps from Duval, in the shadow of the lighthouse.brbrMade up of three individual one-bedroom apartments, the suites are the perfect choice for several couples or families traveling together. Each of the three features a full, modern kitchen, AC splits, TV, and free WiFi. brbrAt charming Coral Cove, you'll find an updated, modern space with colorful, beachy decor and a cozy bistro table on your enclosed patio. In the upstairs Seagrass Suite, enjoy peaceful mornings with coffee on your private balcony, with a view of the Key West Lighthouse. Interior space combines modern updates with antique accent pieces, eclectic art, and cheerful pops of color. brbrFinally, at Mermaid's Retreat, you'll find a beautifully updated space, with colorful, eclectic decor and abundant natural light. Balconies off both the living room and bedroom upstairs are ideal for languid afternoons with a good book and some sweet tea. When bedtime calls, three serene sanctuaries offer a restful night's sleep. It's time to make that Key West getaway a reality at Julia Whitehead Guest Suites - all that's left to do is book. brbrTHINGS TO KNOWbrA booklet inside the apartment features the full story of Julia Whitehead Guest Suites. brThere is no parking available at this property.

Historic Old Town home with three apartments, balcony, & lighthouse view

Key West, Florida, United States

Bed

Bath

Sleeps

$190.26

Beautifully situated among the palms and right on a canal that leads out to open water, this three-bedroom home on Big Coppitt Key is the perfect Florida Keys escape for boating enthusiasts, anglers, and families and friends in search of waterfront relaxation. This single-story home provides a canal-front dock where you can park your boat, two kayaks to take out each morning, and incredibly close proximity to open water two doors down. After a day spent boating and fishing, you can rinse off in the outdoor shower, toss the day's swimsuits in the washer/dryer, and cool of in the bright, tiled, and air-conditioned living space. There's a gas grill on the patio to sear your fresh catch for dinner, a fully appointed kitchen where you can prepare all the side dishes, and a lovely screened-in porch where you can dine al fresco, sip cocktails, and enjoy the glow of the sunset. Use the free WiFi to make plans for tomorrow's adventures, gather around the flatscreen TV in the living room for movie night, and sleep soundly in one of three bedrooms. The master suite features a king-size bed, sliding doors that open to the patio, and an en suite bathroom. The second bedroom has a queen-size bed and the third has two twin beds; the two rooms share the hallway bathroom.br brWhat's nearby:brThis canal-front home is located in a great neighborhood of Big Coppitt Key, with a number of eateries and conveniences a few blocks away on Overseas Highway. The heart of historic Key West is an easy, nine-mile drive west, where you'll find such legendary attractions as the Key West Historic Seaport, the Ernest Hemingway Home and Museum, Southernmost Point, Mallory Square, and the lively shops, restaurants, and bars that line Duval Street.brbrThings to know:brFull kitchenbrOne small dog is welcome for a nightly feebrConstruction equipment/vehicles are prohibited from being parked on sitebrNo smoking and no parties, pleasebrThere is a 28-night minimum stay for this propertybrbrThis property is managed by Seven Keys Vacations by Casago.

Waterfront, Single-Story Home on a Canal w/ Dock, Kayaks, AC - 1 Small Dog OK

Key West, Florida, United States

Bed

Bath

6

Sleeps

$161.37

Experience the best of Key West living! This classic cottage comes fully updated with modern amenities while boasting a prime, central location with easy access to Key West's iconic attractions and historic sites. Suitable for up to eight guests, this spacious three-bedroom home is a perfect for choice a family's Southernmost holiday. Partial AC units are featured in every room of the house, providing cooling comfort from the sub-tropical heat. The front family room is an ideal gathering place with a wall-mounted smart TV to stream your favorite shows and movies during some downtime or evenings at home. The updated kitchen comes equipped with full-size appliances, including a dishwasher, for easy at-home cooking and cleanup. The dinette can sat four. A private paradise awaits in the enclosed backyard -- enjoy the surrounding, native foliage while entertaining guests on the furnished deck. With seating for six at the patio table, this is also an ideal option for al fresco dining!brbrThings to KnowbrFree WiFibrbrThis property is managed by Seven Keys Vacations by Casago.

Bright Keys Cottage with Enclosed Yard, Deck, Porch, Partial, AC, & WiFi

Key West, Florida, United States

Bed

Bath

Sleeps

$171.68

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.*brbrIf Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit of being right in the heart of the island!brbrYou'll be in the center of Key West within walking distance to restaurants, bars, and shops, as well as all the well-known sites, including famous Duval Street. Take a stroll to Ernest Hemingway House and Museum then head to Southernmost Point Beach for an afternoon of lounging on the sand, soothed by the sound of the crashing waves. Fort Zachary Taylor Historic State Park and the National Marine Sanctuary are a mile to the west, and Mallory Square, which offers more shopping and dining, is a mile to the north. The family dog is also welcome to join you here for an additional nightly fee.brbrAfter a fun day of exploring, head home to your tastefully decorated getaway to freshen up, then treat yourself to a mouthwatering seafood dinner at The Little Pearl. Or stay in and work your magic in the full kitchen and enjoy your feast at the small dining table or relax in the living room and watch some a cable show or movie on the flatscreen. The free WiFi will help you get around and create your ideal itinerary, and the private washer and dryer will keep your clothes and humble abode sand free.brbrBook this adorable home today, and get ready for your rejuvenating Key West getaway!brbrThis property is managed by Seven Keys Vacations by Casago.

Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything

Key West, Florida, United States

1

Bed

1

Bath

Sleeps

$241.45

Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a private pool completely surrounded by a rustling wall of palm trees, this upscale rental offers a private, tranquil getaway right in the bustling heart of Key West.brbrThis home lies just two blocks away from Higgs Beach and the Edward B Knight Pier, putting you in a prime location to enjoy one of Key West's best stretches of surf and sand. You'll also be just over a mile from many of Key West's most popular attractions, including the Southernmost Point, the Ernest Hemingway House, and the island's many bars and restaurants.brbrBack home, escape the crowds with a relaxing soak in your private pool, then mix yourself a tropical cocktail and stretch out in the hammock for a lazy afternoon nap. When you get hungry, wander inside to fix dinner in the fully equipped kitchen, then enjoy your meal out on the deck or in front of the flatscreen TV. Free WiFi, central A/C, and a private washer/dryer are also provided for your convenience.brbrThere's no better way to experience Key West than a stay at this first-class home. Book today!brbrThings To Know:brThis property is managed by Vacasa Florida LLC.brPlease note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.

Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$216.11

This home is just perfect for your Keys getaway! The open floor plan and well-appointed kitchen will make your stay more than comfortable. French doors off the living room and primary bedroom offer beautiful views of the private pool and the lush tropical landscape in the enclosed yard. You will enjoy the private outdoor living area, including the patio table and chairs, lounge, gas BBQ grill, outdoor shower, pool floats, and heated saltwater pool accented with underwater lighting. This beautiful home has everything you need to make your next Key West vacation memorable. You won't want to leave, and you will definitely want to come back.brbrThis classic Key West home is centrally located in Old Town, not far from the Southernmost Point of the United States. Numerous restaurants, sandwich shops, and a local grocery store are just a few blocks away. While in the area, stay active playing pickleball and tennis at the nearby courts as well as some classic shuffleboard. Tour the world-famous Duval Street, known for shopping, dining, and entertainment. Enjoy the beautiful sunsets at Mallory Square or dine at one of the many restaurants along the waterfront in the Historic Seaport District. Be sure to visit the nearby Key West's Butterfly Museum and Nature Conservatory, easily one of the area's best attractions.brbrTHINGS TO KNOWbrThe king bed may be separated into two twins upon request.brThis property is managed by Seven Keys Vacations by Casago.brNon-Reserved Street Parking Only. The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only,” and visitors are NOT permitted to park in them.

Old Town Key West classic with private saltwater pool & enclosed patio- by shops

Key West, Florida, United States

Bed

Bath

Sleeps

$269.2

Rate reduced to a off season price point. This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and conveniently located on the Island. This home welcomes you with a white picket fence! It has been nicely upgraded down to the wood floors and crown molding trim. Open living room and dining room concept, separate office with sleeper couch and windows that invite in the Key West sunshine. Each bedroom takes on a personality of it's own with all new furniture and flat screen televisions. Large kitchen with room for two or more cooks and indoor laundry room for convenience. Front and backyard is completely fenced for privacy, with heated pool. Relax in sun chairs while you cook out on your gas grill. Fun outdoor shower allows you to connect to Nature. Large outdoor patio set for those outdoor meals. Enjoy your stay in a great home with plenty of Sunshine! Neighborhood has small walkable bridge that shows nature's natural aquarium. Nice area to kayak, fish or watch nature at it's best. Sorry no pets.

Private Home- Sun-filled Pool- Neighborhood Water Inlet

Key West, Florida, United States

Bed

Bath

8

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

6

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

6

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

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

$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

$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

Bed

Bath

7

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

Bed