Home Vacation Condo Rentals By Owner In Key West, FL

Showing 140 Of 527 Vacation Rentals
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Exceptional(9)

$438.63

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Island Time | Luxury Beach Condo w/ Pool & Hot Tub

Key West, Florida, United States

Summary:brIsland Time is a newly renovated, 2 bed 2 bath condo located in the gated La Brisa Condominium complex. Situated directly across the street from the Atlantic Ocean, you are just steps away from world famous Smathers Beach (the most beautiful beach in Key West) and breathtaking water views. Experience unparalleled tranquility on your private balcony with salt pond views, or relax and socialize at the sparkling, resort-style pool and hot tub to pass the time. Head downtown, a short 10 minute drive or bike ride away, and enjoy vibrant Duval St and all that comes with it.brbrThe Space:brStep inside Island Time and feel your worries and stress fade away. The newly updated kitchen space, part of the open floor plan, is a chef's dream and provides a. all the amenities you need to cook up a proper meal for you and your group. Just of the kitchen, sits the entrance to the guest bathroom and bedroom that sleeps up to four guests - with two full beds. Here, you will also find the laundry closet that is equipped with a full size washer & dryer. brbrMaking your way back into the main space, you arrive in the living area that provides ample natural light. The living area also offers a Queen-sized pull out sleeper sofa that can comfortably sleep up to 2 adults. The private balcony with outdoor seating is located just off the living room and gives you a secluded feel with the view of Key West's nature. Finally, to your right, you will find the spacious, luxurious master bedroom that includes a king size bed, walk-in closet and ensuite bathroom.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrThe Neighborhood:brLa Brisa condominium complex is located in the Midtown Neighborhood of Key West along the island's southern coast. You can smell the ocean breeze from the property which is a short distance to Smathers Beach - Key West's largest and most popular beach. One of the quieter areas of Key West, this neighborhood is just a short walk to the nearest dog park and the White Street Pier. Take the back roads through the Casa Marina area and see some of the island's most beautiful homes. Looking for a nearby bite to eat Check out one of our local favorites: Salute on The Beach.brbrGetting Around:brGetting around this island is easy and fun! With your close proximity to Key West International Airport, arrive with ease. Take a short ride share, taxi, or rent a car or golf cart right when you exit the airport. Key West offers a short distance to most attractions, restaurants, bars, and shops. From your front door, you should expect to get to the center of downtown in 10 minutes or take a shorter route to the Historic Seaport where you can find more available parking.brbrOther Things to Note:brAmenities include: shared pool and hot tub, BBQ grills, sauna, tennis courtsbrQuiet Hours are from 11:00PM to 8:00AMbrLaundry/Towels are not allowed to be hung out over the balconybrThis unit features smart TVs & Youtube TVbrTrash chutes are available for use
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Exceptional(29)

$423.25

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The Tortuga at Sunrise Suites - Balcony & Pool

Key West, Florida, United States

Summary:brbrWelcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 minutes from Duval Street's attractions, this two-bedroom condo complex features uniquely designed units. Enjoy access to a shared hot tub, heated pool, walking paths, biking trails, a tennis court, and on-site laundry facilities—everything you need for a relaxing stay!brbrbrbrThe Space:brbrTwo bedroom two bathroom suite with private balcony overlooking the salt marshes!brbrBedroom 1: King bed, walk-in closet & en-suite bathroom brbrBedroom 2: Queen bed with attached bathroombrbrLiving Area: Queen pull-out couch and a quiet private balcony brbrbrbrAll of your cooking essentials included along with brand new kitchen counters the Tortuga Suite is ready for cooking all your vacation meals.brbrThere is central AC, private parking for 1 vehicle at this unit as well as internet, TV, and cable.brbrbrbrGuest 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.brbrbrbrThe Neighborhood:brbrTortuga Suite is located inside of the Sunrise Suites Resort Community located about 10 minutes away from the World Famous Duval Street and its vibrant restaurants, art galleries and nightlife. Inside the community you can find a corner store, spa, walking and biking trails. It is also located just a short drive away from the nightly Sunset Celebration and entertainment at Mallory Square.brbrbrbrGetting Around:brbrThere is 1 parking spot available per apartment. However, the spots are not marked. They are available on a first-come first-serve basis so we can not guarantee close proximity to your unit. brbrbrbrA second parking spot is a possibility and based off of parking lot vacancy. Should you see an additional spot, you may park free of charge.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber or taxi. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Private stackable washer and dryer - To get you started we supply detergent and dryer sheets.brbr- This unit is located close to the airport.
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Exceptional(5)

$531.0

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Craig & Cindy Key West Truman Annex 2 bedroom 2 bath Shipyard Condo at MM 0!

Key West, Florida, United States

Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include:brbr2 bedrooms 2 full bathroom {queen and 2 twins (or we can convert the 2 twins to a king bed with a king converter) plus a sleeper sofa in the living room.brbrFully equipped kitchen with upgraded appliances and cooking accessories.brWasher & dryer with iron & ironing board.brAll towels and linens, including beach towels.brCentral air & ceiling fans.brSecond floor condo with outdoor balconies (or ask us about renting both an up and down Shipyard condo for even more room)brLarge shared Shipyard pool located just steps away.brFlat Panel TV's and entertainment center.brHigh speed internet with Wi-Fi.brAssigned parking spot for 1 car.brbrLocated in prestigious Truman Annex at Mile Marker 0 - location, location, location. Shipyard Condos are right at the entrance to Ft. Zachary Beach and next to Mallory Square and those famous nightly Sunset Festivals and just two blocks from Duval Street and all of the shops, restaurants, night clubs and museums. While we provide a parking spot, you will not need a car! brbrExcept for festivals such as Fantasy Fest, Meeting of the Minds, and Powerboat Races, we generally require Saturday-Saturday rentals so if your dates are not Saturday-Saturday please email us with your dates prior to booking so that we can check our calendar to see if an exception is possible. brbrSHIPYARD 202-3 IS A RARE TWO BEDROOM TWO BATH (MOST SHIPYARD CONDOS ARE 1 BATH) AND IS 25% LARGER THAN A STANDARD SHIPYARD CONDO.brbrWe have many other Key West Truman Annex vacation rental listings that can be accessed via VRBO. Let us know if you have a particular interest or property size in mind.
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Exceptional(153)

$221.07

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OLD TOWN, STEPS TO DUVAL! LA DOLCE VITA' SLEEPS 2-4! 3 BLOCKS TO SOUTHERNMOST!

Key West, Florida, United States

STEPS TO DUVAL STREET! WALK EVERYWHERE--TO ALL RESTAURANTS, SHOPS AND BARS OF OLD TOWN! You wont need a car with this location!brbrLA DOLCE VITA is located in Old Town, Key West!! Just 3 short blocks to Southernmost Beach and Southernmost Point in the heart of the Historic District.brbr Please check out our calendar for availability & photos and our video.br brThe condo is totally renovated! It has a dramatic high 14 ft ceilings, a granite countertop, galley style kitchen, stainless steel appliances refrigerator w/ great ice maker, 2 burner glass cooktop, large microwave. It has cherry wood floors, queen size bed w/ memory foam mattress, 75 inch flat screen Smart TV in living room, 35' flat screen Roku TV in bedroom, ceiling fans, full bathroom, crown molding throughout w/ recessed lighting on dimmer switches.brbrThis condo is on the second floor and has a shared porch with 2 sitting chairs on a large wrap around balcony where you can sit w/ your favorite drink and listen to the sounds of Key West. :))brbrWalk everywhere! You don’t need a car with this location!! Walk to all bars, restaurants and shopping! Just a few blocks from Southernmost Beach! You are only steps to Duval Street!!brbr 'La Dolce Vita' is on the second floor of an old Victorian, Key West style building with wraparound balcony.brbrA short bike ride away in the Historic Seaport at Conch Harbor is Dante's pool & Raw Bar at 951 Caroline Street. They have a large swimming pool, restaurant, full bar, Tiki bar and it is open to the public (pets are welcome). brbrA block away at 300 Catherine Street is the Community Center which has a large pool, picnic tables, basketball courts & a playground. It i s open to the public. Weekend hours vary. Phone # 305-809-3876.brbrA few short blocks away is Southernmost Beach on the Atlantic Ocean which is free to the public. There is Southernmost Cafe which offers breakfast, lunch and dinner and Happy Hour!brbrA few blocks away is Fort Zachary Taylor Beach. It is Key West's most beautiful beach. It is approximately a 20 minute walk and there is a fee to enter the park/beach. brbrYou will NOT need a car with this location! Park it and leave it! WALK EVERYWHERE! :)brbrIf you would like to purchase any of the artwork in the condo, please inquire. Thanks! :)
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Exceptional(28)

$276.42

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Great Location- Remodeled Condo- Old Town-Truman Annex Close to all attractions

Key West, Florida, United States

Hello, I am Francine -- new owner who recently listed the condo on VRBO. This is why I do not have yet any rating and if you are anything like me -- you are looking for best rating. However, if you trust me and are looking for a relaxing and attractive place while still being in the middle of the action, this place does exist at the Shipyard Condominiums. brbrIt's located in the prestigious gated community of Truman Annex in Key West’s old town area which is 2 blocks from Duval Street, close to the beach and all the Old Town Key West attractions and great restaurants. You can walk to the grocery store (Fausto's), have drinks at the Green Parrot (2 blocks away) and enjoy Fort Zachary Taylor State Park which is around the corner. brbrI just renovated this 2 bedrooms /1 bath condo which is outfitted with washer/dryer, all new appliances in the kitchen, pots/pans, towels, linens, have central air conditioning, pool access and assigned parking inside the gated community. brbrThis end unit condo is on the ground floor and has big, beautiful French doors in the living room and master bedroom. They open onto the private back deck with has outdoor patio furniture. You also have a fully equipped modern kitchen, renovated bathroom, and flat screen TV’s in the living room and wireless internet access. The master bedroom has a king size bed and the guest bedroom has a queen size bed and each bedroom has flat screen TVs. brbrAfter a full day of taking in the island’s many wonderful experiences, come back to the comfort of this home. The manicured landscaping, verdant palms, and white picket fences give the Shipyard and Truman Annex a lovely park atmosphere. All this tranquility makes it hard to imagine that Duval Street, Key West’s central artery of entertainment is only two blocks away. brbrI am looking forward to welcoming you to this lovely sunny condo.brPlease reach out if you have any questions - +1 914 648 8943. Best, Francine
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$293.36

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**DEEP BLUE DREAMS @ THE ANNEX** Oceanside Condo & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrAs soon as you enter, you'll feel like you stepped into a dream. Welcome to DEEP BLUE DREAMS, a modern coastal retreat in the heart of Truman Annex, Key West’s most exclusive neighborhood. This freshly updated 2 bedroom, 2.5 bathroom condo brings a new level of style to island living — sleek and modern, yet relaxed and inviting, with subtle touches of deep ocean blue that inspire its name. brbrJust steps from the waterfront, you’ll enjoy the best of both worlds: the quiet elegance of a gated community and the excitement of Old Town only moments away. Walk to Fort Zachary Taylor State Park and its iconic beach, or head to Duval Street, where world-class dining and entertainment await. Paired with Last Key Realty’s 5-star Guest Services and complimentary Concierge, a stay at DEEP BLUE DREAMS will be so memorable you'll be dreaming about it for years to come.brbrTHE LIVING AREA…brbrDEEP BLUE DREAMS features high ceilings, contemporary furnishings, and a cool color palette accented by deep sapphire walls — a nod to the ocean just beyond. The living room offers ample space to unwind, with a plush leather sofa and matching chairs that you’ll just sink into. A large Smart TV provides entertainment for evenings in, while the glass doors open to a private balcony perfect for morning coffee or a sunset cocktail.brbrThe fully equipped kitchen has everything a home chef could want — stainless appliances, quartz countertops, and all the cookware you’ll need when you’re not dining out at one of Key West’s top restaurants. Gather your group for a home cooked meal at the dining table that seats 4. A convenient powder room is located just off the living area.brbrTHE POOL & THE BEACH…brbrThe Community Pool is waiting outside; large, heated, and lined with comfortable chaises for relaxation. The pool deck overlooks the Gulf of Mexico, offering front-row seats to Key West’s world-famous sunsets. For those who prefer the beach, Fort Zachary Taylor State Park is just a short stroll away, offering swimming, snorkeling, and shaded picnic areas beneath the pines.brbrTHE ACCOMMODATIONS…brbrPrimary Bedroom – King bed, Smart TV, large closet, and an en-suite bath with a glass-enclosed shower and modern finishes.brbrGuest Bedroom – Two Twins or One King (your choice), Smart TV, large closet, balcony access, and easy access to the hall bath with a tub/shower combo.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Smart TVs in Living Room & Bedroomsbr** Fully Equipped Kitchenbr** Basic Stock of Spicesbr** Starter Supply of Paper Productsbr** Starter Set of Cleaning Productsbr** Linens and Towels Providedbr** Wireless High-Speed Internet & Full CablebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Large Heated Community Poolbr** Covered Off-Street Parking for 1 Car (vehicle restrictions apply — no vehicle over 18’ long or 80’’ wide)br** Two Twin Rollaway BedsbrbrOther notes:brbr** Interim housekeeping available upon requestbr** Accommodates up to 6 guestsbr** No Pets Allowedbr** Suitable for families and responsible adult groups only. Groups expecting to host late-night gatherings or make excessive noise should seek alternative accommodations.
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Exceptional(1)

$159.77

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Old Town Studio Cottage with Full Kitchen, In-Unit Laundry & Shared Pool

Key West, Florida, United States

Charming Studio Retreat with Pool Access in Old Town Key West. Escape to island living at this delightful studio located in the heart of Key West’s Old Town. Tucked away on Grinnell Street, this cozy hideaway offers everything you need for a relaxing stay. Step inside to find a bright and inviting space, complete with a fun, well-equipped kitchen perfect for whipping up tropical cocktails or a light meal after a day of exploring.brEnjoy access to a shared swimming pool, where you can lounge in the sun or cool off under the palms. The studio’s thoughtful design makes the most of its space, giving you comfort and convenience just steps from Duval Street, local dining, galleries, and nightlife. Whether you’re here for a quick getaway or an extended island escape, this Grinnell Street gem offers the perfect blend of comfort and Key West charm. Classic Old Town neighborhood atmosphere.br✨ Features:brStudio layout with queen bedbrFun, colorful kitchen with essentialsbrShared swimming pool & sun deckbrClose to Duval Street, shopping & restaurantsbrbrAGE 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 EXCEPTIONSbrbrDiscover the charm of Old Town Key West in this inviting 1-bedroom, 1-bathroom studio apartment. Just 10 minutes from lively Duval Street, this cozy retreat offers the perfect balance of comfort and convenience. Enjoy a full kitchen for at-home meals, a private washer and dryer, and access to a refreshing shared pool for sunny afternoons. Whether you’re here to explore the island’s history, nightlife, or beaches, this studio is the ideal home base for your Key West getaway.brbrTHINGS 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.
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$360.72

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Azure Vista Penthouse

Key West, Florida, United States

Summary:brbrOcean View Penthouse in Downtown Key WestbrbrbrbrThe Space:brbrOceanfront Penthouse at Historic Mills Place – Truman AnnexbrbrWelcome to Oceanfront Truman Annex Penthouse, an exceptional vacation retreat perched in the heart of Mills Place, the most desirable section of Key West’s prestigious Truman Annex. This rare and spacious penthouse condo offers one of the most spectacular views in all of Key West, overlooking the turquoise waters of the Gulf and the bustling harbor where cruise ships gracefully arrive and depart right outside your window.brbrbrbr Unmatched Ocean Views & Spectacular SunsetsbrbrWith four exposures and three private balconies, this home is designed to capture the island’s natural beauty from every angle. Watch breathtaking sunsets over the ocean each evening as you unwind in the expansive living room or enjoy dinner on the main west-facing balcony. Floor-to-ceiling windows flood the living area with light and provide panoramic views of the water, creating an unforgettable backdrop for your stay.brbrbrbr Spacious Interior with Soaring CeilingsbrbrThe penthouse features a grand open living space with 18-foot cathedral ceilings and oversized windows on three sides, making the interior feel light, airy, and endlessly inviting. The fully equipped chef’s kitchen, elegant dining area, and large living room provide the perfect setting for cooking, entertaining, or simply relaxing with loved ones.brbrbrbr Luxurious Bedrooms & Private RetreatsbrbrThe primary suite offers a serene escape with its own private balcony, spa-like en suite bathroom complete with a separate shower and jacuzzi bathtub, and ocean-facing windows. A sleeper sofa in the primary suite adds flexibility for additional guests. The second bedroom is furnished with a plush queen size bed, ensuring everyone enjoys a restful night’s sleep.brbrbrbr☀️ Resort-Style Amenities & Prime LocationbrbrGuests have access to a large, fully equipped pool just steps from the condo, perfect for cooling off after a day in the sun. The home’s prime location means you’re just two blocks from iconic Duval Street, with its world-class restaurants, galleries, and nightlife, and only a short walk or bike ride to Fort Zachary Taylor State Park, home to one of Key West’s most beautiful beaches.
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$324.96

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Helluva Happy Place

Key West, Florida, United States

Summary:brbrEscape to Old Town Key West - 3 Bedroom 2.5 Bathroom Townhome with a Private PoolbrbrbrbrThe Space:brbrEscape to Old Town Key West and indulge in a monthly retreat at our charming 3-bedroom, 2.5-bathroom townhome. Nestled in the heart of the historic district, this hidden gem offers not only a tranquil oasis but also easy access to Key West's vibrant attractions.brbrbrbrStep into your temporary abode and discover a spacious layout designed for comfort and relaxation. With three bedrooms, there's ample space for your family or group of friends to unwind. The master bedroom features a plush king-size bed and an en-suite bathroom, while the other bedrooms offer cozy accommodations and convenient access to a shared bathroom.  Enjoy the streaming tv's in every bedroom.brbrbrbrAfter a day of exploring, take a refreshing dip in your private sparkling pool. Lounge on the poolside deck with a cold drink in hand, soaking up the warm Florida sun. This beautiful outdoor area has a fire table in the backyardbrbrbrbrConvenience is key, and our townhome boasts off-street parking, ensuring hassle-free arrival and departure. Plus, with a fully equipped kitchen, you have the option to whip up your favorite meals or dine out at some of Key West's best restaurants, all within walking distance.brbrbrbrSpeaking of walking distance, you'll find yourself just moments away from a myriad of attractions, including beaches, eclectic shops, and lively entertainment venues. Whether you're seeking outdoor adventures or cultural experiences, you'll find it all right at your fingertips.brbrbrbrDon't miss out on the opportunity to experience the magic of Key West from the comfort of our inviting townhome. Book your monthly stay now and start counting down the days to your unforgettable getaway.
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Exceptional(30)

$621.98

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**SUITE SANCTUARY @ THE BEACH** Oceanfront Condo & Pool + LAST KEY SERVICES...

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrSUITE SANCTUARY is a luxurious penthouse condo that overlooks the ocean and is certain to be your haven from everyday life. This newly renovated condo features many delights throughout, from the vaulted ceilings to the fresh tile floors reminiscent of a walk on the beach. The large balcony offers a place to relax and enjoy the warm Florida weather while watching the ocean lap at the shore. SUITE SANCTUARY is located in an upscale private community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants and activities. A stay at SUITE SANCTUARY is the dose of reality that will remind you just how sweet life can be.brbrTHE LIVING AREA...brbrA unique feature of SUITE SANCTUARY is the vaulted ceilings – in a lovely white wood that sets the tone for this gorgeous beachside condo. The floor-to-ceiling sliding glass doors allow plenty of natural light to fill the living area. There's a large flat-screen TV to enjoy on those nights you feel like curling up and watching your favorite show. The living room features a large comfortable sofa, that pulls out to a Queen sleeper for extra guests, and two armchairs. The fully-equipped kitchen has stainless steel appliances and all of the tools the chef in your group will need to prepare a meal. There's an indoor dining table for six with additional seating at the kitchen bar. The outdoor dining table, which seats six, is perfect for when you decide to stay in and enjoy an ultimate sunset dinner.brbrTHE POOL, THE BEACH & TENNIS...brbr1800 Atlantic offers Resort-style amenities, including an extra large Community Pool right downstairs. There are chaise lounges surrounding the pool for your comfort, and a cabana with restrooms for your convenience. From the pool, there's a walking path that leads to the on-site beach. The on-site beach offers a relaxing setting, with chaise lounges and soft sand. There is no direct water access from this beach, but Smathers Beach, Key West's largest public beach, is located within walking distance right next door. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. You'll also have access to the newly built fitness center and Key West's only clay tennis courts, both located on-site.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom: King bed, a large flat screen TV, direct access to the balcony, and an en-suite bathroom with an oversized shower.brbr** Second Bedroom: Two Twin beds OR One King bed, a flat screen TV, direct access to the balcony, and access to the full second bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable 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** Community Jacuzzi Accessbr** Assigned off-street carport for 1 car (Parking Garage has a low clearance of 6'2)br** Key West's only clay tennis courtsbr** Handball courtsbr** Fitness Centerbr** Dry Saunasbr** Picnic areas with BBQsbr** Recreation rooms available for private partiesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** This complex has both visitors and locals living here, we expect our guests to be mindful & respectful of the posted rulesbr** 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.
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