33040, Florida, United States Vacation Rental Homes By Owner - Page 4

Please contact the owner for stays less than 28 days before you try to book. brMilitary Vouchers are Welcome! brIn Key West - Not Islands Away *br** Ocean Front**Ocean View From Every Room *90' Scenic Balcony Huge 2200 Sq Ft under air. This is a $1.5 Million Dollar Property!br***SPECIAL REDUCED RATES FOR ANNUAL, OR OTHER LONG-TERM RENTALS ***brOCEANFRONT… There is nothing like it. To me, it means being directly on the shoreline with nothing between you and the sensation of the ocean. Totally different from Ocean View, which could mean having to lean over your balcony and look up the side of the building while your partner holds your legs so you don’t fall, all to see a partially obstructed or distant view of the ocean.brOceanfront is like a “front-row-center” at a concert. Going VIP… nothing else comes close; everyone else takes a seat behind you. It’s why you spend all your money to go on a tropical vacation. Everyone wants it… only 1% actually enjoy it. brFor a small island, Key West has very few oceanfront properties. Not only is this suite Oceanfront, it is also one of the largest oceanfront suites in Key West. You are literally about 20 yards to the shoreline. brFrom your 90 ft. long wrap-around balcony, you will enjoy magnificent unobstructed ocean views. The patio is so long, you can view the sunrise from one end and the colorful sunset from the other. brThis suite is located in the most private, secluded, and most desirable portion of the building, away from the pool area and the noise and traffic of Roosevelt Boulevard. Directly in front of you, take in the sights, sounds, and smells of the ocean. To the far right, is Berg Nature Preserve. The only sounds you will hear are those of the ocean birds and windsurfers cutting along the waves. Being in such a secluded area, away from the city lights, the sky is so dark you feel you can touch the stars. Enjoy a nightcap off the master balcony with a loved one, while gazing up at a full moon.brAll bedrooms and the living room have spectacular views of the ocean as you can see from the pictures. There are newly installed reinforced sliding glass doors, which can be left open to allow the tropical trade winds to flow freely throughout your living space. brAs mentioned, this is one of the largest oceanfront suites in Key West, so there will be plenty of room for you and your guests to have their own space. This 3 bedrooms 2 bath suite is furnished with one king-size bed, one queen, and 2 single beds that can be combined to make a king (upon advance request). All 3 bedrooms have a magnificent ocean view like none other. There are also 2 single roll-away beds and an oversized sectional in the living room.brUpgrades include free high-speed wireless internet access, so bring your wireless devices, laptops, and computers. All bedrooms are equipped with new flat screen “smart” television with Hi-Definition Cable. The master bathroom is equipped with a “spa design” shower with a body sprayer. The Master bath includes his and hers separate vanity areas, along with large walk-in closets. brThere is also a new washer and dryer for your convenience. For an additional charge, daily or weekly housekeeping can be provided.brYou don’t have to eat out every night. The eat-in gourmet kitchen is large, fully equipped with high-end appliances, including name brands such as Sub-Zero and Jenn air. Also included are a microwave, blender, toaster oven, coffee maker, toaster, table settings, dishes, and pots and pans. Take a scooter ride to pier fish markets and bring home some fresh jumbo gulf shrimp and stone crabs for dinner tonight as you enjoy the sunset from your outside patio. brAmenities: there is really no need to leave the property. Grab your towel and flip flops and head downstairs. Take a dip in the 70 ft. heated Olympic pool, located just feet from the water’s edge. Recline on the deck and work on your tan. Relax your muscles in the oversized 12 people-in-ground heated Jacuzzi. Take in the well-manicured lush landscape including all varieties of orchards and tropical flowers. BBQs are situated near the shaded pavilion for your convenience. Bathrooms, lockers, and Hot Stone saunas are conveniently located poolside.brA few steps to the left of the property is Smathers Beach, Key West’s longest beach where plenty of activities are located including volleyball, sailboat rentals, and parasailing. brFor a nominal fee, local bike rental companies will drop off “Beach Cruisers” at your doorstep. Ride the numerous bike paths and trails, peddle along the beach, or take a 10-minute ride down to Duval Street and do some afternoon shopping and lunch.brOn your vacation, I suggest you do something different and rent a Scooter or electric car. They are a fun and exciting way to explore the island. brAlso, enjoy a round of tennis. The property is one of Key West’s only clay tennis courts. Also available free of charge are two lighted hard courts and handball courts.brOne covered off-street parking space is provided, and ample guest parking spots are located outside. The property is very safe and secure with a full-time, around-the-clock security patrol.brThe property is located with close access to the airport and car rental area and about two miles to Malory Square, Duval Street, the shopping district, and the cruise ship port.brCheck-in time is 4 pm. Check-out is 10 am. brYou must be 25 or older to rent this unit. Not available to spring break students. Please indicate the ages of all renters in correspondence. brbrbr

HUGE DISCOUNT for 28 day OCEAN FRONT! 90 FT BALCONY

Key West, Florida, United States

Bed

Bath

Sleeps

$344.56

Just a few houses off Duval, this wonderful 2 Bedroom, 2 Bath retreat occupies the ground level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. A large covered front porch welcomes you to sit and watch the Key West world go by, imagining what life was like in the early days of the Southernmost City. Inside, you’ll find a carefully updated restoration featuring tall ceilings and pickled oak floors. The centerpiece of the kitchen area in the great room is a full-sized surfboard, serving as a unique lighting fixture. Sliding glass doors fully retract into the walls, opening onto a spacious covered rear porch that sits right at the edge of your pool deck, offering the ultimate indoor/outdoor living space. A complete renovation was finished in the summer of 2024, giving you a fresh space with large windows, quiet and efficient central air conditioning, and ceiling fans throughout.brbr ** This is a Monthly Rental Only ** br Due to local regulations we can only rent this property for a minimum of 28 Days. brbrAfter a day of island exploration, refresh and unwind in one of the two comfortable bedrooms, each featuring a king-size bed and a flatscreen Smart TV. Both bedrooms have en-suite custom-tiled bathrooms with glass-enclosed rain and handheld showers, deluxe vanities with undermounted sinks, and floor LED lighting. Just before entering the front bedroom, you’ll find a Samsung washer and steam dryer laundry niche in the hallway. The living room includes a queen-size sofa sleeper, allowing the unit to accommodate up to six guests. Of course, all linens and towels are provided, along with a hairdryer, iron, and ironing board. brbrBring your gourmet chef to enjoy the latest Samsung Bespoke range with an air fry oven and a French door Bespoke refrigerator with a pull-out freezer and in-door beverage center. Under the large Quartzite dining island, there is a drawer microwave and two-drawer dishwasher from GE’s designer Café line of appliances. We’ve also included a combo Keurig “K” cup and full-pot coffee maker in the dedicated coffee bar, and an on-end rowboat converted into your wine center. Additionally, there’s a wide array of specialized appliances for your enjoyment. You’ll find a complete selection of glassware, including several types for your favorite wine, along with a full set of dishes, silverware, and all the necessary utensils.brbrThe counter seating accommodates four guests around the large 10-foot Quartzite island dining area. Right outside the kitchen door on the back porch, there’s a true infrared gas grill and a dining table with seating for four to enjoy meals by the poolside. The following small appliances are also available for your use: Toaster Oven, Coffee Maker, Bean Grinder, Blender, NutriBullet, Waffle Maker, Panini Sandwich Press, Crock Pot Slow Cooker, Rice Cooker.brbrbrDesigned for Your Extraordinary Stay.brStylish Old Town Getaway with Pool, Steps from Duvalbrbr Key West, FloridabrbrGuests: Up to 6 GuestsbrBedrooms: 2brbr Beds: 2 King bedbrbrAbout Virginia VerandabrbrJust a few houses off Duval, this wonderful retreat occupies the ground level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. A large covered front porch welcomes you to sit and watch the Key West world go by, imagining what life was like in the early days of the Southernmost City.brbrInside, you’ll find a carefully updated restoration featuring tall ceilings and pickled oak floors. The centerpiece of the kitchen area in the great room is a full-sized surfboard, serving as a unique lighting fixture. Sliding glass doors fully retract into the walls, opening onto a spacious covered rear porch that sits right at the edge of your pool deck, offering the ultimate indoor/outdoor living space. A complete renovation was finished in the summer of 2024, giving you a fresh space with large windows, quiet and efficient central air conditioning, and ceiling fans throughout. brSleeping and Bath Arrangements brbrAfter a day of island exploration, refresh and unwind in one of the two comfortable bedrooms, each featuring a king-size bed and a flatscreen Smart TV. Both bedrooms have en-suite custom-tiled bathrooms with glass-enclosed rain and handheld showers, deluxe vanities with undermounted sinks, and floor LED lighting. Just before entering the front bedroom, you’ll find a Samsung washer and steam dryer laundry niche in the hallway. The living room includes a queen-size sofa sleeper, allowing the unit to accommodate up to six guests. Of course, all linens and towels are provided, along with a hairdryer, iron, and ironing board. brKitchen Facilities brbrBring your gourmet chef to enjoy the latest Samsung Bespoke range with an air fry oven and a French door Bespoke refrigerator with a pull-out freezer and in-door beverage center. Under the large Quartzite dining island, there is a drawer microwave and two-drawer dishwasher from GE’s designer Café line of appliances. We’ve also included a combo Keurig “K” cup and full-pot coffee maker in the dedicated coffee bar, and an on-end rowboat converted into your wine center. Additionally, there’s a wide array of specialized appliances for your enjoyment. You’ll find a complete selection of glassware, including several types for your favorite wine, along with a full set of dishes, silverware, and all the necessary utensils.brbrThe counter seating accommodates four guests around the large 10-foot Quartzite island dining area. Right outside the kitchen door on the back porch, there’s a true infrared gas grill and a dining table with seating for four to enjoy meals by the poolside. The following small appliances are also available for your use: Toaster Oven, Coffee Maker, Bean Grinder, Blender, NutriBullet, Waffle Maker, Panini Sandwich Press, Crock Pot Slow Cooker, Rice Cooker. brLiving Room brbrIf you’re in Key West during that special sporting event or television broadcast, you can enjoy it on the big-screen Smart TV in the living room. Watch from the couch or the accent chair, or rotate the TV slightly to view it from the counter stools. The living room is also a comfortable space for conversation. There is another seating area in the rear of the great room, complete with two barrel chairs and side tables, located next to the coffee and wine area. The couch opens into a queen-size bed to accommodate two extra guests if needed. brbrThe large 8’ x 28’ covered rear porch is accessible from both the rear bedroom and the great room via 8-foot tall, 6-foot wide sliding glass doors that fully retract into the walls, providing seamless indoor/outdoor living. Just outside the great room doors, you’ll find the Tru-Infrared Gas Grill, conveniently located near the pool deck. The porch also includes comfortable chairs outside the bedroom for a cozy conversation area, and a dining table with four armchairs for outdoor meals. All of this overlooks the beautifully landscaped backyard, which features a large pool with a Dominican Coral Stone pool deck and a waterfall.brbr brbrYou’ll love refreshing yourself in the newly built 10’ x 20’ pool, completed in 2024. This custom-designed concrete pool features a deep end with a ladder, entry/exit steps, and wrap-around benches in the shallow end. The pool is heated during the cooler months for your comfort. The gentle sound of the babbling waterfall soothes the senses, while the surrounding tropical plants create the quintessential Key West experience.brbrAfter swimming, dry off and catch some sun on the Dominican coral stone pool deck, which stays cool even in full sun. The backlit, mirror-polished stainless steel palm tree makes for a great backdrop for personal photos. Behind the stainless palm mural wall, you’ll find a convenient half-bath and an outdoor bamboo shower with a vintage surfboard holding your shower controls. This beautiful outdoor area and pool are only shared with the upper two-bedroom unit of the house, Virginia Vista. brbrBeing less than a block from Duval Street puts you in the perfect location to easily walk to many of the best attractions Key West has to offer. You are also located about halfway between the Southernmost Point Buoy and the Key West Lighthouse and Hemingway’s House, just a short stroll either way on Whitehead Street.brbr You’re not just on vacation now… You’re LIVING IN KEY WEST!br We sincerely want you to enjoy the vibe that has captivated so many of us here forever!brbr KEY WEST… CLOSE to PERFECT, FAR from NORMAL!brbr ** This is a Monthly Only rental ** br Due to local regulations we can only rent this property for a minimum of 28 Days. brbr

VIRGINIA VERANDA, Stylish Old Town 2 B/R, 2Bath, with Pool, Steps from Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$638.03

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrWelcome to CASA DEL MONO, a spacious coastal retreat where island living unfolds at an easy, graceful pace. It’s the kind of place that invites you to slow down, settle in, and stay awhile. With five bedrooms and four bathrooms, plus expansive wraparound porches upstairs and down, this beautifully appointed home offers plenty of room to spread out while still feeling effortlessly connected. Light-filled interiors, playful jungle themed decor, and thoughtfully curated spaces create a calm, sophisticated atmosphere where days drift easily from poolside lounging to evening conversations under the palms. Paired with Last Key Realty’s Guest Services & In-house Concierge, your month at CASA DEL MONO will be memorable and relaxing.brbrTHE LIVING AREA & KITCHEN... brbrWhen you enter CASA DEL MONO, you’ll feel right at home. This luxurious home features an open-concept first floor, that connects the multiple living rooms, kitchen, and dining area, making the ample space feel even bigger. Plush sofas in the living room invite you to sink in and get comfy. There will be no fighting over what to watch on the large flat screen TV, because if the first living room is spoken for, the rest of the group can gather in the second living room, which also has a large flat screen TV in addition to having seating, a mini bar, beverage refrigerator, and prep sink!brbrThe first living room flows right into the dining area, which features seating for 6 at the table and 4 at the kitchen island bar. In the fully equipped kitchen you have any and every appliance you may need. Every tool the chef of your group needs to prepare their signature dish will be on hand just in case. The office nook under the stairs is the perfect place to get work done during vacation, equipped with a computer and WiFi printer.brbrTHE BACKYARD & POOL… brbrYou’ll swear you’ve rented your own private resort when you enter the tranquil backyard CASA DEL MONO has to offer. From the shaded seating under the lanai, to the soft astroturf beneath your feet, to the serene blue waters of the pool, CASA DEL MONO has it all. Just off the pool is a pool cabana, complete with a/c and seating, the perfect retreat for some quiet reflection or afternoon scrolling. Outdoor TVs by the pool and under the lanai allow for endless entertainment. Fire up the propane grill and treat your group to a poolside BBQ on the covered lanai. A convenient passthrough window connects the lanai and kitchen, making entertaining a breeze. This impressive backyard space wouldn't be complete without an outdoor shower, a Key West staple.brbrTHE LOCATION... brbrCASA DEL MONO is located in a quiet residential area of Midtown, less than a half mile from Higgs Beach, where you can lay on the beach, dine at Salute! or jog with your dog to the Dog Park. Plenty of parking is available for any number of vehicles, mopeds, and bicycles. Best of all, you’re just a few blocks from Old Town and all its attractions.brbrTHE ACCOMMODATIONS... brbr** Bedroom #1: Located on the first floor, featuring a King bed, flat-screen TV, closet, direct access to the covered lanai, and direct access to the full first floor bathroom with a walk-in shower.brbr** Master Suite: Located on the second floor, featuring a King bed, large flat-screen TV, private balcony, and an en-suite bathroom with double sinks, a walk-in shower, and a soaking tub.brbr** Bedroom #3: Located on the second floor, featuring a Queen bed, two closets, access to the upstairs balcony, and an en-suite bathroom with a walk-in shower.brbr** Bedroom #4: Located on the second floor, featuring Two Twin beds (rope suspended), closet, and access to the jack-and-jill bathroom with a walk-in shower.brbr** Bedroom #5: Located on the second floor, featuring Two Twin beds OR One King bed, closet, and access to the jack-and-jill 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 Rooms & Backyardbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge ServicebrbrIn 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 Heated Poolbr** Pool Cabanabr** Off-Street Parking for 2 Medium-Sized Vehicles in the Drivewaybr** Propane BBQ Grillbr** Outdoor Showerbr** Outdoor TVsbr** Sonos Sound SystembrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 10 adultsbr** No Pets Allowedbr** 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.

**CASA DEL MONO @ MIDTOWN** Stunning Private Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

5

Bed

4

Bath

10

Sleeps

$409.44

Escape to Above The Horizon, a stunning 3-bedroom retreat in the exclusive gated Truman Annex — just one block from the energy of Duval Street and moments from the waterfront at Truman Waterfront Park and beautiful Fort Zachary Taylor State Beach. Enjoy tropical garden views, two balconies, and a heated pool next to your garden patio in the heart of Old Town.brbrAbove The Horizon blends island charm, comfort, and history, offering the perfect sanctuary for an extended stay along one of the most beautiful streets in Key West. This lovely 3‑bedroom, 2 bath, multi‑level condo is just moments away from live music, waterfront sunsets, farmers markets, dining, and beach adventures — yet worlds away in your own peaceful oasis.brbrInside, the condo feels bright and open with vaulted ceilings, elegant island décor, and breezy tropical views. The main level features a king‑size master suite, a twin bedroom, laundry facilities, a spacious living and dining area, and a fully equipped kitchen. Upstairs, the aery spacious queen loft suite offers a private balcony surrounded by lush scenery, with a peek of the ocean — the perfect spot to sip wine as the sun fades into the horizon. brbrStart your day with coffee surrounded by blooming orchids in your private bistro garden, enjoy a refreshing dip in the heated pool just steps from your patio, or bike a few minutes to Fort Zachary Taylor Beach, known as Key West’s best. In the evenings, watch the sunset from the the Truman Waterfront, explore local restaurants and live entertainment, or simply unwind on your balcony under a blanket of stars.brbrPart of the original 1844 U.S. Naval Base Hospital, Above The Horizon offers an authentic connection to Key West’s storied past while providing every modern comfort — including parking, multiple verandas, and serene garden views.brbrWhether you’re here to relax, explore, or reconnect, Above The Horizon is more than a vacation rental — it’s your home in paradise.brbrPlease note: This property will require a minimum of a 28 night stay.

Luxury Truman Annex Condo I 3BDR I Pool & Parking I Walk to Duval & Beach

Key West, Florida, United States

3

Bed

Bath

Sleeps

$988.82

Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Southern Comfort. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The 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 house.brKey Feature: br3 en'suite bedrooms each with porch accessbrThis home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with plush couches around a large HD flat screen Smart TV. One of the couches also pulls out to a Queen-sized sleeper sofa for additional guests. There is a dining table with seating for up to 6 diners, with additional seating for 4 at the kitchen bar. brThe master bedroom has a King size bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a King size bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The bathroom is en-suite. The third bedroom is also on the 2nd floor with twin beds, flat screen TV, balcony access and en-suite bathroom. On the main floor there is a fourth bedroom with twin bed. There is a half bath down the hall.brOut back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. The backyard is complete with a large propane grill for a poolside BBQ. 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 8 guests.brbrDockage is not available at this home's development.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).brbrDOG FRIENDLY. Please contact us to confirm specific pet policies.

Luxury Waterfront Home with private pool

Key West, Florida, United States

Bed

Bath

Sleeps

$138.89

True Key West flavor! br1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on White St.with hardwood flooring ,high ceilings ,furnished and full gourmet kitchen. Beautifully decorated!brNear by local grocery store and few steps away great Cuban coffee and sandwich shop.You will find yourself within walking or biking distance to all Key West has to offer. brbrBedroom has queen size bed with memory foam mattress and fine linens.brThis unit has two Smart TV's and Washer / Dryer.brbrPrivate Patio/Outdoor Area.brThe health and safety of our guest is very important- current cleaning CDC guidelines has been implemented at our property.br* Cleaning service weekly or bi-weekly available on request*brbrMinimum stay 28 days

Mango Tree Key West Cottage

Key West, Florida, United States

Bed

Bath

Sleeps

$2269.4

br**28 day minimum rental due**brbrMake yourself at home in this 8-bedroom Key West waterfront estate. brbrA housekeeper is available Monday-Friday at no additional chargebrbrWith 10 bathrooms, there’s plenty of space for everyone to enjoy privacy and comfort. The bedrooms feature a mix of 1 king bed, 1 bunk bed with trundle, and 6 queen beds, perfect for families or groups. brbrGuests can stay comfortable year-round thanks to heating and air conditioning throughout the property. brbrAn outdoor kitchen at the pool house, swim up bar, fire pit, dock and fish cleaning station makes a great area to do what you should do in key west - be outside.brbrA well equipped fitness room invites you to keep up with your workouts while away. brbrThis beautiful and welcoming estate offers a marvelous setting for relaxation and fun. You’re sure to make fantastic memories with a stay at our place.

Key West Waterfront Estate with guest home - with housekeeper!

Key West, Florida, United States

8

Bed

10

Bath

17

Sleeps

$540.0

Welcome to Our Home Away from home. Our condo is located in the LaBrisa complex which is a GATED COMMUNITY across from Smather's Beach.brALL PHOTOS ARE CURRENT AND ACCURATELY DEPICT OUR SPOTLESS HOME.brRENTAL CALENDAR SHOWS NIGHTLY RATES- discount given for 7 or more nights.brbrOur tropical oasis is waiting for you to kick back and enjoy. Perfect for large families (the master bedroom has 2 full sized beds (that could accommodate 4 people), second bedroom has a queen sized bed, living room has a sleeper sofa. brbrFully equipped kitchen makes dining out an option rather than a necessity (gas grill bron site for barbeques). Wi-fi (bring your lap top), 3 flat screen TV's keep you in touch. You don't have to leave the property to enjoy the heated pool, whirlpool spa, sauna, tennis court, lounges and covered patio. Pool and whirlpool are available to guests 24 hours a day, great to take a midnight swim! brbrStep across the street and onto famous Smather's Beach (voted #6 of Florida's 10 best beaches by the travel channel)where you can relax in the shade of a palm tree or join in the many activities available. Smather's Beach is the largest in Key West; it boasts chair and raft rentals, food vendors, snorkeling, sailing, parasailing, paddleboarding and kayaking.brbrKeywords: Condominium, La Brisa Community, Sanitized

GATED OCEANFRONT CONDO AT SMATHER'S BEACH

Key West, Florida, United States

Bed

Bath

Sleeps

$1294.51

Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boasts a large two car garage with stairs leading up to the main floor consisting of a sprawling kitchen appointed with all the tools even the most experienced chefs would envy. brJust in front of the kitchen is a large wood dining table to seat 6 comfortably while overlooking past the living room and towards the water. There is a kitchen bar which allows for additional seating as well. brThe Living rooms is comfortably situated with a pull out sofa and large HD flat screen with full HD cable. brWish to enjoy the tropical air Lounge on your private balcony and watch the charter fishing fleet depart or return amidst their daily catch. Enjoy the spectacle and camaraderie while they unload the catch of the day with just a short walk from your oasis. brOn the next floor are two master suites with en suite bathrooms. Each suite has it's own balcony and walk in closets. All your luxury linens exceed the highest of standards and we aim to provide you with the comfort to make your stay not only memorable, but heavenly as well. brBring the whole family! The top floor has a loft with 4 twin beds, which can be arranged to make two King beds (with notice) and a central bathroom. The top floor also has a private room with two twin beds as well and can also be joined to make one King bed. Whether its kids or adults, this home provides numerous options to accommodate the widest of sleeping accommodations necessary, not often found in ole Key West. br2023: New custom dining table, new couches and chairs, new carpeting as well as new LVT on stair treads and landings! brThe heated pool is located in the rear yard which is situated a mere distance to the water and your own private boat slip. You can choose to walk from the main floor balcony down your private steps to your private liana or through a private door from the garage. Either way, seclusion is what you have to relax in when at Bayview Retreat!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).brbrDOG FRIENDLY. Please contact us to confirm specific pet policies.

Luxury Waterfront Home with Private Pool and Dock!

Key West, Florida, United States

4

Bed

3

Bath

10

Sleeps

$1112.64

A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old Conch House, but with all the amenities of a new luxury home. brSituated on the edge of Old Town Key West near everything Key West has to offer, your home boasts tall ceilings, large rooms, an expansive and well appointed kitchen with custom cabinets as well as a heated pool and private boat slip. brEnjoy the convenience of two off-street parking spaces or simply bike to Duval St. Bayview Park is only a block away and was built on the premise that at one time it overlooked the bay before expanding Key West to include New Town. brbrEnter to a shotgun view (reference to old Key West homes which would allow, if fired, a shotgun shot to pass from the front door to the back door with out interruption) of the downstairs through which you can view the custom kitchen, dining area, living and lastly, back yard. The kitchen has custom cabinets and stainless steel appliances as well as all teh tools you'll need to prepare the finest of cuisine! brJust in front of the kitchen is a large wood dining table seating 6 comfortably. brThe Living rooms is comfortably situated with a pull out sofa and large HD flat screen with full HD cable. brbrWish to enjoy the tropical air Lounge on your private porch take a dip in your private heated pool. brbrOn the next floor are two master suites with en suite bathrooms in each. Each suite has it's own balcony and walk in closets. All your luxury linens exceed the highest of standards and we aim to provide you with the comfort to make your stay not only memorable, but heavenly as well. brbrBring the whole family! The top floor has a loft with 4 twin beds, which can be arranged to make two King beds (with notice) and a central bathroom. The top floor also has a private room with two twin beds as well and can also be joined to make one King bed. Whether its kids or adults, this home provides numerous options to accommodate the widest of sleeping accommodations necessary, not often found in ole Key West. brWe hope to have you as our guest at Eisenhower's Retreat!br brRATES: 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).

Conch style home in Oldtown with private pool AND dock!

Key West, Florida, United States

Bed

Bath

Sleeps

$200.11

This is an amazing second floor two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away from it all. Enjoy mornings out on the rear deck overlooking the refreshing community pool. Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and close to all of the Old Town Key West attractions. The properties are also located 1/4 mile from one of the best beaches on the island. All properties are outfitted with washer/dryer, pots & pans, towels & linens, condo has central air conditioning, off street parking and community pool access. brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Poolside Hangover at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$264.76

Sophisticated 2 bedroom, 1 bathroom Key West Home just steps from the white sand and salty hues of Smathers Beach, short bike ride to Higgs beach, famous Louie’s Backyard, Mile Marker One, and all that Key West has to offer. Conveniently located near Key West Golf Club for those looking to sharpen their golf game. This home has recently been completely remodeled and available for select dates! brbrHome comes equipped with gas grill, two bikes, two fishing poles, beach chairs and cooler. Our retreat is perfect for a month of relaxation, working remote and exploring Key West !

Perfect 2 BR Escape Near Smathers Beach w Bikes, fishing poles & Beach Chairs!

Key West, Florida, United States

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Bath

Sleeps

$1670.63

Summary:brbrDiscover your dream Key West getaway at Lunara Bay - a collection of 26 Luxury homes in a gated community! Ebberly Estate is a 6BR, 6.5BA pet-friendly home blending island charm with modern elegance, just minutes from downtown. Dock boats up to 40’ at private slips, relax in your private pool, access the FYT gym, and enjoy curated itineraries from our local guest experience team.brbrbrbrThe Space:brbrExperience seamless indoor-outdoor living here! Ideal for entertaining with the open-concept layout, fully equipped kitchen,the poolside lounging, ping pong games, grilling, and multiple dining areas – ensuring unforgettable moments.brbrOutside, a spacious fenced grass yard offers safe play for children and freedom for furry friends to roam.brbrbrbrSleeping arrangements include:brbrBedroom 1: King bed, walk-in closet, double vanity en-suite, balcony accessbrbrBedroom 2: King bed, walk-in closet, double vanity en-suite, balcony accessbrbrBedroom 3: King bed, en-suite bathroombrbrBedroom 4: King bed, en-suite bathroom, balconybrbrBedroom 5: Two twin bunk beds (no door)brbrBedroom 6: Double bed, en-suite bathroombrbrbrbrGuest Access:brbrOur self check-in makes the process seamless. brbrbrbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrbrbrBoating & Private Dock Slip:brbrWe encourage boating. Here's what you need to know in order to do so safely:brbr- Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip.brbr- There is no power or pump out service to the slips.brbr- The Florida Keys are a notoriously difficult place to navigate.brbrbrbrThe Neighborhood:brbrWelcome to Lunara Bay!brbrNestled in a gated community less than a mile from Key West, Lunara Bay offers a family-friendly atmosphere with a local park just a short walk away—perfect for spending time with loved ones.brbrbrbrExplore & Dine Nearby:brbrEnjoy fresh seafood and local flavors at Hogfish Grill, Roostica, or Chico’s Cantina. Visit Hurricane Hole for happy hour and scenic waterfront views. Rent a boat for a day at Stock Rock Café or embark on a kayak tour with Lazy Dog.brbrbrbrBoating & Marina Access:brbrMany homes offer private boat docking or slips available at the onsite marina. A public boat ramp is conveniently located across the highway - Key Haven Boat Ramp.brbrbrbrNeed personalized recommendations Ask your GEM for their top things to do and places to go!brbrbrbrGetting Around:brbrTravel by car, boat, or plane to our luxury estate. The driveway allows parking for up to 4 vehicles and your boat trailer. brbrbrbrIf you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. brbrbrbrRent a golf cart, scooter, moke or bikes for the day to explore the area. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Extend your stay 7+ nights for 10% off your entire stay!brbr- Elevate your stay and ask us about our Private Chauffeur services.brbr- Private washer/dryerbrbr- Located in gated communitybrbr- Free gym access at FYTbrbr- Pets are welcome! Our requirements are as follows: brbr•40lb maximum per petbrbr•$250/staybrbr•2 pet maximumbrbrbrbrInteraction with Guests:brbrYour dedicated GEM is at your service to answer any questions or curate unforgettable experiences tailored to your dreams in the Keys.

The Ebberly Estate at Lunara Bay

Key West, Florida, United States

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Bath

Sleeps

$160.44

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.brbrLocated facing the tranquil lush courtyard at 1800 Atlantic. This spacious family retreat features a renovated kitchen. Both bedrooms and the living room open onto the expansive private balcony facing the tropical oasis.brFull size washer dryer & wireless. Guest bedroom features a queen bed. The Master Suite is set up more family style with a king, double and twin bed. Come and relax in this retreat and enjoy all the amenities of 1800 Atlantic. There is an olympic size heated pool. 20 person jacuzzi out by the pool. 3 Tennis courts one of which is clay. Fitness center and much more. We have secure parking and security. brWe have a small sunning beach area on property and are literally a 5 minute walk to Smathers Beach , Key West's largest beach. 2 miles from Downtown Key West and the Historic district.

Smith Families Southernmost 2 Bedroom retreat, Key West style beach vacation

Key West, Florida, United States

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Bath

Sleeps

$450.0

This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-minute walk will take you to the iconic Duval Street, the heart of Key West.br brThe unit located on the second floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is complete with new appliances and all you need to cook and serve your favorite dishes. The bedrooms all have ceiling fans, new furniture and a large TV in each room. In the living room, there is plenty of seating with a new comfortable sofa bed and a 55 inch TV.brbr28 NIGHT MINIMUM STAYbrbrmore information at: sweetcarolineseaportbrbrConciergebrbrOur Concierge affords travelers an astonishing level of personal services. Upon your arrival, our concierge will introduce you to the best of Key West.brbrWith our local knowledge, we create a true connection between Key West and our guests by personalizing each and every experience.brbrYour personal concierge is Kelsey.

Sweet Caroline Historic Seaport Key West Home Rental Floor 2

Key West, Florida, United States

Bed

Bath

Sleeps

$109.71

Studio Apartment for Rent in Key WestbrbrThis cozy studio apartment is located in a quiet, gated community on Grinnell Street in Old Town, Key West. It's perfect for those seeking privacy and tranquility while still being close to all the attractions that Key West has to offer, including the night life on Duval Street, beaches, and restaurants.brbrProperty Details:br- Queen-sized bedbr- Newly updated bathroom with smart toilet and bidet (LED nightlight, heated seat, and auto-open features)br- Large-capacity Cuisinart Digital AirFryer Toaster Oven and microwave for easy meal preparationbr- Bright and airy with Dade County Pine walls and five large windows providing natural lightbrbrShared Amenities:br- Access to a large pool shared with several vacation homesbr- Lounge chairs provided for relaxing by the poolbrThe studio offers the perfect combination of quiet relaxation and convenience, situated in a peaceful part of town but still close to everything.

Serene Key West Studio with Poolside Peace

Key West, Florida, United States

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Bath

Sleeps

$780.71

Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the main house - it is in a back cottage, separated by a pool. On the other hand, this is the perfect layout for two couples or families with older children, as this setup offers much more privacy. brbrKey West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. brbrThis 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open floor plan with original Dade County pine walls and ceilings. The main house has hard wood flooring throughout and houses the master suite, a fully equipped gourmet kitchen and the living and dining area. Inside the house are all the comforts of home, with every room providing its own unique feel. brbrThree sets of French doors lead from the living and dining area onto your own private lanai and pool area. Bask in the sun and listen to the tranquil sounds of falling water, which is the backdrop of the heated pool. Tropical plants and flowers are abundant and offer complete privacy for guests. The back gardens and pool area were designed to create a calming effect, which pervades the mind, body and spirit.brbrThe detached cottage offers a 2nd bedroom and bath with a private open-air shower – what better way to enjoy your morning shower than amidst flowering bougainvillea trees! The cottage also features 20 ft vaulted ceilings and two sets of French doors which open to the garden and pool area. Guests tell us they love having the detached cottage, as it offers couples traveling together much more privacy.brbrKey West Oasis is located in the historic Old Town district, close to restaurants, bars, Duval Street etc. To give you an idea of what is located around the house, check out the distance to the following:brbr The Bike Shop Rentals, Famous Sandy's Café, and Faustos Supermarket, 1 blockbr Shakti Yoga, Key West Cakes Bakery, The Local BUtcher & Market - 1.5 blocksbr Liquor/beer store, 2 blocksbr El Siboney Cuban Restaurant, 4 blocksbr Key West Cemetery, 3 blocksbr Duval Street, 8 blocksbr Higgs Beach, 9 blocksbr Key West Bight Marina, 10 blocksbr

Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard

Key West, Florida, United States

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Bath

4

Sleeps

$171.04

brOutdoor patio, Full kitchen and Close to the beach brbrbrbrWKLY SPECIALS @ br12% OFF Wklybr& REDUCED RATES brbr This is a very good value at abrGREAT LOCATION Close to beach and All!brREASONABLE RATES. W.FULL KITCHEN AND PATIObrPlease read reviews. People have left and judge for yourself..brKey West is old and historic whenbrThe homes were built-in this area. Parking was always on the sides of the street and is FREE.brA great way to see the island however, is by bicycle plus there are so many different kinds of vehicles you can rent it is amazing.brbrSO.........brbrCome splash in the surf. Come soak up the heat of the Sun. Come feel salt water mist on your skin as you take a sunset sail! Come listen to the beat of the reggae drums. Come feel the loose sand in your feet as you sway to its rhythm. Feel alive and vibrant.brCARPE DIEM!.brYou will be staying at Varela Street Retreat. Only a beautiful half-mile walk from the beach.br My place has a full kitchen with full size refrigerator and stove. A complete dining area and a living room/bedroom combination and bathroon. You also have your own large private patio.The 1/2 mile walk straight down the street to the public beach is lovely.brThe beach also has a nice small restaurant onsite.brYou will love staying in this great location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm, friendly and diverse group. Here you will absorb the ambiance that made Key West what it is today.brVarela St. Retreat is located in historic Old Town away from the bustle on famous Duval Street. It is only half a mile to the closest beach and a 7 minute walk to Duval Street. It is less that one block to the White Street art gallery district, the grocery, the laundry, the largest city park,restaurants, shops, bike rental shop and more.brGo ahead, kick your feet up and make yourself at home! You are about to enter Varela St. Retreat. Here you will meander back a secluded stone pathway to reach your very own private, spacious stone patio complete with lush overhanging tropical vegetation.brA table and chairs and plantsbrawait you. You can dine out and soak up the warm inviting Florida sunshine,chat with your friends or just catch up on some reading. The front room of your apartment is a combination of a full kitchen and a separate dining/office area. The back room has a queen-size bed and a living area complete with a sleeper sofa. The bathroom has a stall shower. The apartment has all new ceramic tile and wood laminate flooring.brVarela St. Retreat offers FREE parking right on the sides of the street in designated areas. First come first serve. brbr Also, ask me about a pool hook up if needed. So please come and make Varela St Retreat your temporary home while away from home!brbrKeywords: House

Summer Special@129 Sun. thru Wed. ngts.lodging Only 129. + extras.

Key West, Florida, United States

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Bath

Sleeps

$180.0

Close to beach, Full Kitchen and front porch. Very Reasonably Pricedbrbr with 12% OFF Lodging + extras.WKLY staysbr br brCome enjoy the Sun, Surf and Sand of the Tropical island paradise of Historic, fun filled Key West.brYou will love staying in this great location where 90% of the people are localsbrThey each have an interesting Key West tale to tell and are a warm, friendly and diverse group. Here you will absorb the ambiance that made Key West what it is today. Varela St Retreat is located in the historic Old Town section away from the hustle and buste of noisy Duval St. brThere is free parking on the sides of the street in designated areas.brIt is only 1/2 mile to the closest beach and a 7 minute walk to Duval the main street. It is less than 1 block to the White Street art gallery district, the grocery, laundry, shops, restaurants, park and more. brGo ahead and kick your feet up and make yourself at home! You are about to enter Varela St Retreat. Here you will have your very own private full front porch to enjoy. It is a good place to eat, exchange local gossip or just plain curl up and read a good book. brThe apartment features a luxurious oversized shower, full kitchen, internet, cable and more. brbrKeywords: House

Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras

Key West, Florida, United States

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Bath