Home Vacation Condo Rentals By Owner In Key West, FL

Showing 60 Of 527 Vacation Rentals
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Exceptional(2)

$334.84

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~AZUR PALM~ Oceanfront elegance with pools, peace, and a designer interior!

Key West, Florida, United States

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrPROPERTY: As you open the door to this amazing home via its tiled, arched portico you will be greeted by seas of blue! Off the entry hall is a stunning white kitchen with tray ceiling, upgraded appliances, quartz countertops and counter seating for four. The kitchen affords views of the ocean and overlooks the dining area with glass table and seating for six. brbr The living room is accented in aquatic colors with an abundance of seating as well as a built-in wall unit with TV. A wall of sliders leads to the covered, oceanfront balcony with a table for alfresco dining, large sofa, and loungers. The primary king bedroom is light and bright with dresser storage, TV and an ensuite bath with a glass, walk-in shower. The bedroom opens to the balcony where you can enjoy morning coffee while listening to the sounds of the sea. The second bedroom has twin beds, two chairs and an ensuite bath with a glass, walk-in shower. Sliders allow light in while window shades provide privacy if needed. brbrLuxurious finishes, tile floors, gorgeous lighting and ceiling fans adorn the stylishly furnished rooms. Enjoy the cool breezes and breathtaking sunsets and sunrises from your balcony. If you have been longing to indulge in a vacation with a view and be lulled to sleep by the sounds of the sea, this upscale oceanfront home is waiting for you! brbrBED CONFIGURATION: There is a king bed in the primary bedroom and two twin beds in the second bedroom that may be converted to a king. There is a sleeper sofa for the occasional overnight guest. brbrOUTDOOR AMENITIES: There are tennis courts, a fitness center, two shared grill areas and two shared, heated pools. The pools are heated seasonally. The beach is just a few yards away. brbrPARKING: There is one assigned parking space in the garage with elevator access. brbrLOCATION: Near the White Street Pier, Higg’s Memorial Beach Park, and the Key West Nature Preserve. Within walking or biking distance of shops, restaurants, and the delights on Duval Street. brbrPETS: This home is NOT pet-friendly. (If you have pets, please browse through our many homes that are pet-friendly.)brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult***brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Managed by Historic Key West Vacation Rentals***brbrNote: Check-ins to KWBC must occur before 9 pm.
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$303.38

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A Sunset Celebration at the Key West Golf Club

Key West, Florida, United States

This lovely, fully furnished, townhouse has three bedrooms that sleeps up to 6 and two full baths . The spacious upstairs bedrooms offer one King bed in the master with dresser, a roomy closet, and an ensuite full bath featuring a walk in shower. One shared full bath with shower/tub combo is in the hall. A unique screened porch with full glass bifold doors opens and extends the living space overlooking the golf course and pond for tranquil nature and wildlife views. This home has a well equipped kitchen with dishwasher and microwave. Flat screen Smart TVs in the living room and each bedroom with streaming Direct TV content. Complimentary Wi-Fi service is provided as well. A propane grill to cook your surf and/or turf of the day is in your raised deck backyard. This home is located within the Key West Golf Club Community and offers a private gated entrance with 24 hour security services providing a safe environment for an evening neighborhood walk or use of the large, heated waterfall pool and the exercise room/gym. These complimentary amenities are located just a short walk across from your front porch. An additional pool is located across the street from the guarded entrance to the community. Both pool locations offer complimentary open Wi-Fi access. This home provides a serene vacation setting when a tropical escape is needed but still just a few moments away from the sights and entertainment of Historic Duval Street in downtown Key West.
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Exceptional(10)

$792.18

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Alligator Reef Light Suite

Key West, Florida, United States

Summary:brbrLuxury 2BD/1BA Suite with Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Porch with Amazing Views.brbrbrbrThe Space:brbrEscape the Ordinary...brbrbrbrThe Alligator Reef Lighthouse Suite offers two queen bedrooms and was completely refurbished in 2024, sleeping up to 6 guests. This beautifully appointed ground floor suite, located in a renovated 1930s Historic Key West building, offers a private exterior entrance and a spacious private front porch with Key West Lighthouse and partial Duval Street views tucked away on a quiet Key West Lane. The Suite is located steps away from the two brand new oasis pools and brand-new amenities on the property.brbrbrbrSuite Amenities:brbrbrbr•           Luxury queen beds with premium linensbrbr•           Queen sleeper sofabrbr•           Fully equipped kitchen with granite countertopsbrbr•           Spa quality stone rain shower bathroombrbr•           Hardwood flooring throughout the suitebrbr•           Spacious front porch with lighthouse and partial Duval St. viewsbrbr•           Smart TVs with the latest Roku device for apps and streamingbrbr•           High-speed Fiber Wi-Fibrbr•           Washer and dryerbrbr•           Luxury well-appointed furnishing and artworkbrbr•           Reserved parking space for one vehiclebrbr•           Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Alligator Reef Lighthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind.  This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr•           Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr•           Brand-new spacious pool decks around each poolbrbr•           Six luxury teak chaise loungers with umbrellas and pillowsbrbr•           Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr•           Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr•           A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr•           Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr•           Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr•           Covered bar kiosk for enjoying a cocktailbrbr•           Key West tropical foliage throughout the property with lighted step-stone pathsbrbr•           Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr•           Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3, two-bedroom suites, 2, one-bedroom suites, 1, one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr•           The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/1BA), and Tortugas Harbor Suites (1BD/1BA) are located at 419 Truman Ave. in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr•           The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr•           The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr•           Key West Lighthouse Museum, 2-minute walkbrbr•           Ernest Hemingway Home and Museum, 2-minute walkbrbr•           Blue Heaven Restaurant, 5-minute walkbrbr•           Southernmost Point Buoy, 8-minute walkbrbr•           Key West Butterfly Conservatory, 8-minute walkbrbr•           Sloppy Joe’s Bar, 12-minute walkbrbr•           Key West Amphitheater and Park, 12-minute walkbrbr•           Mallory Square Sunset, 12-minute walkbrbr•           Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!
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Exceptional(14)

$558.03

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SombreroReef Light Suite

Key West, Florida, United States

Summary:brbrLuxury 1BD/1BA Suite with Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Porch with Amazing ViewsbrbrbrbrThe Space:brbrEscape the Ordinary...brbrbrbrThe Sombrero Reef Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 guests and was completely refurbished in 2024. This beautifully appointed second floor suite, located in a renovated 1930’s Historic Key West building, offers a private exterior entrance and a spacious front porch offering Key West Lighthouse and partial Duval Street views tucked away on a quiet Key West Lane. The Suite is located steps away from the two brand new oasis pools and brand-new amenities on the property.brbrbrbrSuite Amenities:brbrbrbr•           Luxury king bed with premium linensbrbr•           Queen sleeper sofabrbr•           Fully equipped kitchen with granite countertopsbrbr•           Spa quality stone rain shower bathroombrbr•           Hardwood flooring throughout the suitebrbr•           Spacious second floor porch with lighthouse and partial Duval St. viewsbrbr•           Smart TVs with the latest Roku device for apps and streamingbrbr•           High-speed Fiber Wi-Fibrbr•           Washer and dryerbrbr•           Luxury well-appointed furnishing and artworkbrbr•           Reserved parking space for one vehiclebrbr•           Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Sombrero Reef Lighthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind.  This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr•           Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr•           Brand-new spacious pool decks around each poolbrbr•           Six luxury teak chaise loungers with umbrellas and pillowsbrbr•           Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr•           Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr•           A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr•           Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr•           Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr•           Covered bar kiosk for enjoying a cocktailbrbr•           Key West tropical foliage throughout the property with lighted step-stone pathsbrbr•           Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr•           Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3, two-bedroom suites, 2, one-bedroom suites, 1, one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr•           The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr•           The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr•           The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr•           Key West Lighthouse Museum, 2-minute walkbrbr•           Ernest Hemingway Home and Museum, 2-minute walkbrbr•           Blue Heaven Restaurant, 5-minute walkbrbr•           Southernmost Point Buoy, 8-minute walkbrbr•           Key West Butterfly Conservatory, 8-minute walkbrbr•           Sloppy Joe’s Bar, 12-minute walkbrbr•           Key West Amphitheater and Park, 12-minute walkbrbr•           Mallory Square Sunset, 12-minute walkbrbr•           Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!
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$127.44

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Cubana Casita - Downtown Key West

Key West, Florida, United States

Cubana Casita is an easy-access ground floor condo with one bedroom and 1½ baths. This special home's 'from the ground up' interior remodel was completed in 2023 and features new everything. It starts with the white stucco building that houses this condo and others. The three-story building was constructed in 1910 for Dr. J. G. Campbell, a surgeon dentist specializing in gold crowns, bridges, and plate work. Locals talk of how the structure was used as a spy headquarters during WWII but, of course, no records seem to exist to confirm that. brbrEnter Cubana Casita from your private front door on Fleming Street, named after one of Key West's four original founders and one of the most historic streets in Key West. From the rear of the condo sits your own private patio. Enjoy your meals alfresco or just relax with a glass of wine and a great book. Your gated patio leads to one of the most delightful, secluded, and quiet courtyards and pools in town. brbrKey West is a magical walking town. Cubana Casita is located just two blocks from the world-famous Duval Street. Close enough for an easy walk but far enough to offer quiet and serenity. Out your front door it's only a short walk to the local grocery / liquor store, some of the island's best restaurants, bars, galleries, and shops. brbrThe lovingly curated remodel was designed by two artists and combines modern fixtures, technology, and functionality with Cuban and Latin American influences. Don't let the casita's handmade charm fool you. Modern convenience and technology powers this home, including 300 Mbps upload & download speed fiber internet. More than enough to support multiple devices and stream without disruptive connectivity issues.brbrYou'll live like a local in this well-appointed home. Inside, the air-conditioned layout features an open concept living / dining room / kitchen area, master suite with remote workspace and one and half bathrooms. The living room is anchored by a 7' x 7' corner sofa with a rustic coffee table and matte black propeller-style ceiling fan for plenty of air circulation.brbrThe condo has a 55 LED Smart TV in the living room and 40” LED Smart TV in the bedroom. The televisions are equipped with the YouTube TV streaming service which includes 100+ channels, including all of the typical cable TV channels plus the ABC, CBS, NBC, Fox and PBS network affiliates from Miami (our broadcast TV market). You can also stream your TV subscriptions or log into your Netflix or Amazon Prime TV subscriptions, directly from the TV’s. A portable Bluetooth speaker is provided to enable you to stream your Key West soundtrack from your streaming music services on your Smartphone.brbrA Cuban-style distressed dining table is part of the open-concept living space and has four Hemmingway inspired black leather & wood chairs. One of the chairs doubles as a chair for the workspace in the bedroom.brbrThe new kitchen (2023) is fully outfitted with everything you'll need to eat and drink like a local. All stainless-steel appliances frame the kitchen's hickory cabinets. A toaster oven and large microwave offer convenience and a new induction range / oven (equipped with air fryer), offer choices for ambitious cooks. A quiet dishwasher rounds out the new kitchen. brbrIn the entry hall is the conversation piece red half bathroom, featuring a handmade red Cuban wood vanity, vessel sink, local artwork and extra storage. The entry hall makes practical use of the space with a 7' long black bamboo bench and hand forged coat hooks made in a Havana foundry. It's a great resting spot to gather and stage everything for your daily comings and goings.brbrThe star of the show in the master bedroom suite is the handmade Cuban tile and the four-post queen bed, draped with gauze scarves, creates a comfy shabby chic vibe that complements the ceiling fan and memory foam mattress that provide comfort for hot and cold sleepers alike. A 40 wall mounted LED Smart TV is an added treat on a slow-rise morning or lazy evening.brbrA 'work from anywhere' workspace is integrated into the master suite in the form of a 52 L-shaped desk, complete with ring light for Zoom meetings and ample outlets for your own mobile office gear and chargers. brbrThe master bathroom showcases a European glass shower and another handmade Cuban vanity with vessel sink. The vanity light was made by a local artist using reclaimed antique glass insulators and iron piping. Adjacent to the shower another local artist pays homage to Key West's famous neighborhood chickens with a hand drawn chalk art chicken on the gilded white chalkboard. Behind the art lies the on-demand water heater, so you'll never have to wait for an old water heater to get your hot shower.brbrLots of attention to detail make this home extra livable. Top-down island roman shades allow you to balance privacy with natural light. The home's lighting designer outfitted the space with dimmable warm LED lighting throughout, including dramatic spot lighting. Your private washer and dryer are located, conveniently, in a closet within your private patio area. brbrIf you like to swim or are a sun worshiper, you still haven't explored the best part of Cubana Casita; the courtyard and pool. The pool, for the exclusive use of Campbell Courtyard guests, is larger than your typical Key West dipping pool. It is temperature controlled in winter and generously sized by Key West standards. The pool/deck area is ringed with a white picket fence and plenty of foliage to create beauty, privacy, and the kind of tranquil peace of mind only nature can provide. Ample chaise lounges, chairs and a market umbrella seating area provide lots of space for enjoying the lush courtyard and pool. brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.
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Exceptional(27)

$236.12

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A Peace of Paradise at The Truman Annex in Key West

Key West, Florida, United States

Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This second floor end unit was completely remodeled with flair and detail. Open design with new flooring, coastal hues and furnishings -feels spacious and decadent. The kitchen sparkles with quartz countertops, mermaid backsplash, new stainless appliances, and a show-stopping chandelier. Relax on the Italian leather couch and enjoy the custom artwork designed for this property. After a day of frolicking, slip into the new bed featuring cozy organic bedding. The double French doors lead to a huge deck- perfect for morning coffee, entertaining or sunset enjoyment. The Shipyard includes a heated pool, assigned parking, security, and tree shrouded walking paths. The condo is perfectly placed in the very desirable Truman Annex offering a tranquil neighborhood, yet so close to the newly developed Truman Waterfront Park, Fort Jefferson State Park and its popular beaches, and the excitement of Duval St.brPlease note: This property has a 28 night minimum stay
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Exceptional(48)

$247.45

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COLORFUL COCKTAIL @ Truman Annex in Key West

Key West, Florida, United States

Welcome to your perfect Key West getaway! Nestled in the coveted Shipyard community of Truman Annex, this beautifully maintained 2-bedroom, 2.5-bath townhome offers the ideal mix of island charm and modern comfort — all just steps from the vibrant energy of Duval Street, the Southernmost Point, and Fort Zachary Taylor Beach.brbrThis two-story townhome features a bright and airy living space with tropical-inspired décor, a fully equipped kitchen, and a private back deck perfect for morning coffee or evening cocktails. On the first floor, you'll find one full bath and one half bath along with a guest bedroom with two twin beds (that can also be set up as a king upon request). Upstairs, you’ll find the master bedroom as well as a loft room with a full-size futon and another full bathroom.brbrRelax by the community pool, stroll through lush palm-lined streets, or explore world-class dining, shopping, and nightlife just outside your door. With gated entry, assigned (FREE) parking, and all the comforts of home, this is island living at its best.brbrWhether you’re here for relaxation, adventure, or a bit of both — this Shipyard gem puts you in the heart of it all!brbrPlease note: This property will require a minimum of a 28 night stay.
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Exceptional(19)

$329.49

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A Palm Oasis at Mills Place in the Truman Annex

Key West, Florida, United States

This charming two bedroom, two and one half bath townhome has recently been updated and added to our rental program!brFreshly painted and refurnished, this adorable property is located right on the pool and also 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 twin beds that can be converted to a king.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 27 night minimum stay
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Exceptional(2)

$1141.5

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The Lighthouse Penthouse Suite

Key West, Florida, United States

Summary:brbrTwo Luxury Suites Creating a 2BD/ 2BA Two Oasis Pools, Pergola, Outdoor Bar and GrillbrbrbrbrThe Space:brbrThe Lighthouse Penthouse Suite is a combination of two 1 BD/ 1 BA Suites delivering two luxury king bedrooms with two luxury bathrooms accommodating up to 8 guests. This listing includes the entire second floor of our historic 1930s Key West building featuring two of our luxurious suites, the Sombrero Reef and Tortugas Harbor Lighthouse Suites.. It also delivers a front porch with Key West Lighthouse and partial Duval Street views and an oversized rear porch offering Key West Lighthouse, breathtaking pool and amenity views, and a partial view of the famous Hemingway House tucked away on a quiet Key West Lane. The Suite is located only steps away from our two brand new oasis pools and property amenities.brbrbrbrSuite Amenities:brbrbrbr     •           Two luxury king beds with premium linens brbr     •           Two queen sleeper sofasbrbr     •           Two fully equipped kitchens with granite countertopsbrbr     •           Two spa quality stone rain shower bathroomsbrbr     •           Hardwood flooring throughout the suitesbrbr     •           Two amazing second floor porch with lighthouse, pool and partial Duval St. viewsbrbr     •           Smart TVs with the latest Roku device for apps and streamingbrbr     •           High-speed Fiber Wi-Fibrbr     •           Two Washers and dryersbrbr     •           Luxury well-appointed furnishing and artworkbrbr     •           Two private entrancesbrbr     •           Reserved parking space for two vehiclesbrbr •           Luggage hut to store luggage and belongings in before check in or after check outbrbr brbrLocation:brbrThe Lighthouse Penthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrbrbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbr brbrThe Lighthouse Suites Collection is truly one of a kind.  This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbr brbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, The Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbr brbrIn January 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites. brbr brbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink, and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbr brbrProperty Amenities:brbr brbr     •           Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr     •           Brand-new spacious pool decks around each poolbrbr     •           Six luxury teak chaise loungers with umbrellas and pillowsbrbr     •           Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr     •           Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr     •           A brand-new 200 SF teak pergola with a louvered open or closed ceiling  brbr     •           Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr     •           Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr     •           Covered bar kiosk with smart TV for catching a ballgame or enjoying a cocktailbrbr     •           Key West tropical foliage throughout the property with lighted step-stone pathsbrbr     •           Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr     •           Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more Suites for your stay. We have 2 two-bedroom Suites, 3 one-bedroom Suites, a 1 one-bedroom bungalow and our largest one-bedroom one and a half bath Honeymoon Suite, accommodating a maximum of 28 guests. Our property is perfect for weddings, other large gatherings, and events.brbr brbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbr brbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbr brbrWe can accommodate one vehicle per Suite. If you rent multiple Suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbr brbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbr brbr     •           The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbr brbr     •           The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbr brbr     •           The Carysfort Light Suite is a separate individual one bedroom/ one and a half bath home with its own exclusive off-street parking space, located at 217 Eanes Lane.brbr brbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbr brbr     •           Key West Lighthouse Museum, 2-minute walkbrbr     •           Earnest Hemingway Home and Museum, 2-minute walkbrbr     •           Blue Heaven Restaurant, 5-minute walkbrbr     •           Southernmost Point Buoy, 8-minute walkbrbr     •           Key West Butterfly Conservatory, 8-minute walkbrbr     •           Sloppy Joe’s Bar, 12-minute walkbrbr     •           Key West Amphitheater and Park, 12-minute walkbrbr     •           Mallory Square Sunset, 12-minute walkbrbr     •           Fort Zachary Taylor State Park & Beach, 12-minute walkbrbr brbr5. Can we check in earlier or check out later and can we leave our bags before check-in brbrCheck-in is at 4:00 PM, and check-out is at 10:00 AM. On your arrival day, our cleaning staff will be diligently preparing your suite to ensure everything is perfect for your stay. While standard check-in begins at 4:00 PM, we may be able to accommodate an earlier check-in on a case-by-case basis, depending on the previous guest’s departure. If you arrive early, we are typically happy to allow you to drop off your luggage and belongings so you can begin exploring the island. Late check-out may also be possible if no new guest is arriving that day, and this too is arranged on a case-by-case basis.brbrbrbrWe look forward to welcoming you to paradise!
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Condo

The Lighthouse Group Suite

Key West, Florida, United States

Summary:brbrTwo Luxury Suites Creating a 4BD/2BA with Lockout Door, Two Oasis Pools, Pergola, Outdoor Bar and Grill and a Private Front Porch and Back Patio.brbrbrbrThe Space:brbrEscape the Ordinary...brbrbrbrThe Lighthouse Group Suite combines two 2 BD/1 BA units into a spacious 4 BD/ 2 BA retreat featuring one luxury king bedroom, three luxury queen bedrooms, and two full bathrooms, along with two queen sofa beds—accommodating up to 12 max guests. Occupying the entire first floor of our historic 1930s Key West building, this suite brings together the American Shoal and Alligator Reef Lighthouse Suites through a convenient lockout door, allowing them to function as one seamless suite. Guests can relax on the front porch with views of the Key West Lighthouse and partial glimpses of Duval Street, or retreat to a private rear patio with additional Lighthouse views. Nestled on a quiet Old Town lane, the suite is just steps from our two brand-new oasis pools and resort amenities.brbrbrbrSuite Amenities:brbrbrbr•           One luxury king bed and three luxury queen beds with premium linensbrbr•           Two queen sleeper sofasbrbr•           Two fully equipped kitchen with granite countertopsbrbr•           Two spa quality stone rain shower bathroomsbrbr•           Hardwood flooring throughout the suitesbrbr•           Spacious front porch with lighthouse and partial Duval St. views and a spacious back porch for diningbrbr•           Smart TVs with the latest Roku device for apps and streamingbrbr•           High-speed Fiber Wi-Fibrbr•           Two washers and dryersbrbr•           Luxury well-appointed furnishing and artworkbrbr•           Reserved parking space for two vehiclesbrbr•           Two private entrances and an inner connecting lock out door in the suites for privacy or an open areabrbr•           Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Lighthouse Group Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind.  This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr•           Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr•           Brand-new spacious pool decks around each poolbrbr•           Six luxury teak chaise loungers with umbrellas and pillowsbrbr•           Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr•           Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr•           A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr•           Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr•           Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr•           Covered bar kiosk for enjoying a cocktailbrbr•           Key West tropical foliage throughout the property with lighted step-stone pathsbrbr•           Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr•           Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3, two-bedroom suites, 2, one-bedroom suites, 1, one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr•           The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr•           The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr•           The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr•           Key West Lighthouse Museum, 2-minute walkbrbr•           Ernest Hemingway Home and Museum, 2-minute walkbrbr•           Blue Heaven Restaurant, 5-minute walkbrbr•           Southernmost Point Buoy, 8-minute walkbrbr•           Key West Butterfly Conservatory, 8-minute walkbrbr•           Sloppy Joe’s Bar, 12-minute walkbrbr•           Key West Amphitheater and Park, 12-minute walkbrbr•           Mallory Square Sunset, 12-minute walkbrbr•           Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!
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$448.82

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Condo

Paradise on the Ocean at The Truman Annex in Key West

Key West, Florida, United States

This waterfront two bedroom condo is located in the Truman Annex, Key West's premier residential community. Enjoy endless sunsets from all of the rooms and the balcony. The primary suite features King bed and large beautifully appointed bath. The guest bedroom features twins which can be converted to a King bed if desired. Just let us know and the housekeeper will have it set up for you prior to arrival. Complimentary wireless internet is provided for your convenience. Each bedroom has a flat panel TV and the living room offers a conventional TV. All kitchen amenities included, so just pull some ice from freezer and make up a nice pitcher of tea while relaxing and watching the sailing ships along the island filled horizon.brHarbour Place has a large heated swimming pool directly on the ocean exclusively for Harbour Place residents. These are the largest condos in Truman Annex. This stunning unit has one assigned covered parking spot. Enjoy this location with only a couple of blocks walk to Duval Street, Mallory Square, and the world famous natural Fort Zachary Taylor State Park and Beach. brPlease note: This property has a 28 night minimum stay
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$135.71

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Condo

Campbell Cottage - Condo in the Heart of Downtown Key West!

Key West, Florida, United States

All the elements are here to make the perfect vacation cottage: one highly comfortable king bed, one full bath, an open floorplan with living-dining-kitchen areas, a front porch looking over the large Monaco-style pool, and a location very near world-famous Duval Street and the lively Historic Seaport featuring the scenic Harborwalk.brbrThe first steps into the cottage are up onto the porch that features two chairs and a small table. Above a ceiling fan provides light for night, air circulation, and sets a delightful tropical theme. A swath of cloud white organza billows at the front door as if to usher guests into a magical setting. The multiple windows throughout are likewise draped in the fabric that creates privacy and artistic interest. The décor colors are borrowed from the ocean: blue water, ivory shells, red corals, the sunlight, the sky. brbrA social area offers a couch with decorative pillows, a ratan chair, and a round coffee table. On the opposite wall hangs a flat screen positioned for easy viewing from the couch. It’s the perfect place for discussing the day’s plans or playing a round of Key West Monopoly. Maybe drink your coffee or cocktails here but out by the pool or on the front porch is also ideal. Of course, there’s cable and wireless high-speed internet. If you find you need an extra bed, the couch is also a full sleep sofa.brbrThe next area is defined by an artisan sideboard with storage space and four sturdy stool-chairs. This area can function as a dining table for meals or a space for doing computer work or a game area or craft project area or whatever you might need a table for. The space is well located beside the kitchen area. brbrThe kitchen is well equipped with everything you need to make a meal or warm up leftovers from dinner out the night before. And plenty of cabinet space above and below creates space to store stuff. There’s a coffee machine, toaster, dishes, glassware, silverware, a stove with a glass cooktop for easy cleanup, and a double sink. A back door just off the kitchen leads to a small patio and a washer/dryer for laundry. Parking, should you need it, is on street.brbrThe other side of the room includes an unexpected design element: a section of hollow glass brick forming part of the wall and reflecting soft ambient light. On the other side of this wall is the bedroom and full bath. The bed is a generous king and the perfect spot for a relaxing daytime nap and a comfortable sleep through the night. Nightstands with lamps are on either side and serve as a good place for the novel you’re reading and for your cell phone. A flat screen TV is on the opposite wall, a positioning that allows comfortable viewing from the bed. The closet provides space for hanging clothes and some shelf space for foldables. A cabinet under the tv provides even more shelf space. All the storage makes it easy to put things away and out of sight. A bladed ceiling fan whirring above adds a tropical ambience and circulates air throughout the room. Adjacent is the generous-sized full bath with a wall of mirror glass, spacious sink, shelves for towels, and a tub with a soothing shower.brbrThe inside of the cottage takes care of your vacation living needs very efficiently and very comfortably. Back outside, you can step off the porch onto the deck of the large, heated, residents-only pool and make yourself comfortable on one of the chairs or stretch out on a chaise lounge. The pool is large enough for swimming. Or for less movement, maybe you want to float looking up at puffy white cumulus against a blue-blue sky. In either case, don’t forget the suntan lotion. When you want shade, move to the table and chairs on the upper deck or back to the table and chairs on your own covered front porch.brbrBesides a delightful cottage and a spectacular pool, its perfect location is another element contributing to the appeal of the cottage. Despite its tranquility, the location is only two blocks off world-famous Duval Street and three blocks from the Historic Seaport, both must-experience destinations in the Southernmost City.brbrWhen you are ready to check it all out, head up Fleming three blocks to Margaret and turn left. At the corner of Margaret and Caroline you are about a hundred feet from the Historic Seaport and Harbor Walk. Follow the wooden boardwalk along the Gulf to find historic tall ships offering day and sunset cruises or take an all-day ferry excursion to the Dry Tortugas. If you’re interested in watersports, there’s all kinds—diving, fishing, parasailing, snorkeling, and jet skiing to name a few. If you get hungry, a dozen or so restaurants of varying levels of informality ring the harbor. brbrOr walk two blocks in the other direction to Duval Street to find tours, museums, shopping, more restaurants, more bars, and the Key West Aquarium. Your cellphone can identify sunset time, so you don’t miss the daily celebration at Mallory Square where locals and visitors alike gather to applaud as the sun sinks its fiery orange circle into the horizon. If you’re lucky, you’ll catch the elusive neon green flash at the last second. But it’s not yet time to put your day to rest; instead hang around for the party as artists and street performers entertain the crowd with magic, juggling fire, telling fortunes, and selling handmade items. brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Or check out info on the current music scene, movies, plays, gallery openings, and charitable events at milezerokeywest.com. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.
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$327.52

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Condo

The Courtyard - Condo in Downtown Key West!

Key West, Florida, United States

Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs, and shade umbrella above. Tropical foliage and a locked privacy fence surround the whole lushly landscaped compound. But don't be fooled-despite its beauty and quiet tranquility, the compound is only two blocks off Duval Street and three blocks from the Historic Seaport, both listed (among many other locations) as must-do's in any Key West vacation guide. brbrWhen most visitors arrive, the sparkling pool and surrounding deck juxtaposed against a ring of palms, ferns, and bougainvillea is what grabs their attention. Thoughts turn to swimming or paddling around in the refreshing, temperature-controlled water under the southern sun. Or maybe you imagine something even more relaxing like stretching out in one of the chaise loungers to nap or to cultivate your tan or to read a magazine. If you need more reading material or a DVDs for viewing, the Key West Library, the first branch in Monroe County's 50-year-old public library system, is right across the street. Maybe instead you picture yourself sitting under a shade umbrella with a glass of ice tea or some frothy cocktail. Maybe you'll email a selfie from here to friends back home. The best part of a vacation is that the choice of how to spend your time is all yours. There is assigned off street parking for one mid size or smaller car. (If your vehicle is too large to park in the space (vehicles must be less than 16 ft.) you will have to find on street parking.)brbrUp a few stairs from the winding walkway, you step onto the private, covered front porch of the cottage that looks like it could qualify for the cover of Cottage Style or Southern Living. Freshly painted wooden decking, two white wicker arm chairs with pillows, and a matching wicker side table offer a perfect place to enjoy a morning latte and a pastry from the Old Town Bakery. A wall-mounted lantern next to the front door provides illumination and a stylish accent piece to complete the picture. As you enter through the front door, the living area is to your left. It offers a cozy conversation cluster: couch, two armchairs, a coffee table, an area rug, and two lamps, each decorated with cheery hand-painted images of bright tropical fish. To the right are two armchairs and a round table next to a stereo and TV cabinet. Of course there's cable TV, wireless high-speed Internet, and a DVD player. Ceiling fans throughout help circulate air and add a beachy flair to the design scheme.brbrThe galley kitchen has blond cabinets, some with glass doors, set into clean white walls. Black accents in the appliances and artwork add the right touch of contrast. Everything you need to create a gourmet meal is handy. Or even if you feel less ambitious, the kitchen is highly functional and made even more so by a breakfast bar with accompanying chair stools. A window over the double sink ushers in plenty of ambient light, as do the sliding glass doors opening onto the back deck. Looking out, you see something amazing-a large tree trunk growing through the wooden deck planking and extending through the roof. Glancing up, you can see the top of the tree and all its leaves in canopy form above. The private deck comes complete with glass-top table and four chairs. The gas grill is nearby in case you get inspired to barbeque for lunch or dinner and enjoy your feast al fresco at the table, maybe with a glass of your favorite wine or a bottle of some craft beer. Or relax in the hammock chair suspended in one corner.brbrBack inside, next to the living room, is an inviting bedroom with queen bed and all the creature comforts like fluffy bedding, side tables, lamps, a ceiling fan, dresser, TV, and a generous closet for hanging clothes. A framed painting of a conch cottage adds fun Key West color to the room. The full bath is adjacent to the bedroom and also cleverly designed to be accessible through another door opening into the living room. Like the rest of the cottage, the dominant bath color is cloud white with colorful art accents on the walls. A shelf holds plenty of nubby white bath towels, hand towels, and wash cloths.brbrWhen you're unpacked and ready, slip on your flip-flops and head out to explore the rest of the Southernmost City. Walking just three blocks will bring you to the Historic Seaport and Harbor Walk. Follow the wooden board walk along the Gulf of Mexico to find historic tall ships offering day and sunset cruises or take an all-day ferry excursion to the Dry Tortugas. If you're interested in watersports, there's all kinds-diving, fishing, parasailing, snorkeling, and jet skiing. If you get hungry, a dozen or so restaurants of varying levels of informality ring the harbor. brbrOr walk two blocks in the other direction to Duval Street to check out tours, museums, shopping, more restaurants, more bars, and the Key West Aquarium, where you can pet a shark if you dare. Check you cell phone for sunset time so you don't miss the legendary celebration at Mallory Square, where locals and visitors alike gather to witness the sun sinking into the horizon. Be sure to applaud at the magical moment when the last round edge of fiery orange disappears. If you're lucky, maybe you'll catch the elusive neon green flash at the last second. Hang around to enjoy the carnival atmosphere as artists and street performers entertain the crowd with circus cats and magic tricks. Others juggle fire, tell fortunes, strum guitars, and sell handmade items. In between you can buy conch fritters and other small food items while pop-up sidewalk bars offer many varieties of cocktails, wine, beer, and soda. brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.
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$325.97

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Condo

Campbell Suite - In the heart of Old Town

Key West, Florida, United States

Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell Suite, a second & third floor condo with one bedroom and 1½ baths, is the perfect place to anchor your vacation. It starts with the pale-yellow stucco building that houses this suite and others. The three-story building was constructed in 1910 for Dr. J. G. Campbell, a surgeon dentist specializing in gold crowns, bridges, and plate work. Locals talk of how the structure was used as a spy headquarters during WWII but, of course, no records seem to exist to confirm that. The front staircase leads up one flight from Fleming, one of the most historic streets in KW. The back staircase overlooks and leads down to one of the most delightful, secluded, and quiet courtyards and pools in town. And if that's not enough, you are only two blocks from the world-famous Duval Street, home to everything exciting, historic, funky, and weird about this one-of-a-kind tropical island community.brbrUp one flight of stairs, the solid front door to the condo swings into an open floor plan flooded with ambient light. The wall to the right has a sliding glass door that opens to a small, covered balcony with two chairs and side table. Sitting here is a tree-house-like experience. Relax. View blue skies, rooftops, and large areas of swaying palms. If you've come to Key West for outdoor living, this might be your go-to spot for morning coffee or happy hour drinks. As is a common practice where space is at a premium and the weather temperate, the washer and dryer are located, conveniently, in a small closet to the right of the balcony seating area. brbrBack inside, a couch and chair offer a cozy setting for conversation while a ceiling fan whirrs above, gently moving air and adding a certain Bogie & Becall ambiance to the area. A flatscreen smart TV is located here for viewing from the roomy couch. In addition to regular cable channels, it offers streaming apps you can use if you have account(s). It's a great spot for catching up on some vintage movies filmed in the Keys like Beneath the Twelve Mile Reef (1954) or binge-watching a Keys TV series like Bloodline (2015-2017). Of course, there's high speed wireless internet, and central AC. A round table with two chairs offers a spot for eating or mapping out sightseeing destinations for the day. On the opposite wall is a book cabinet with reading material and a basket of beach towels for your inevitable trips to the water's edge. brbrA generous-sized kitchen offers everything you'd need for preparing a four-course meal. Or if your style runs more toward warming leftovers from some luscious restaurant meal, that's a snap, too. A large window over the sink is the visual center of the kitchen, pairing beautifully with the recessed spot lighting, a double sink, stainless appliances, a long prep counter, and copious wooden cabinets above and below. brbrAcross from the kitchen is the convenient and nicely appointed guest half bath. And beside that, a dramatic spiral staircase leads up to the bedroom level. At the top, the bedroom offers a comfy king bed, a full bath, a closet that accommodates hanging and folded items, and a full-length mirror. Like the living-room balcony below, the windows in this space allow views of lovely foliage swaying in tropical breezes. A chest of many drawers provides even more space for your travel accouterments, while an armchair with lamp makes a spot for reading or maybe just a quick sit-down to put on your Crocs or flip flops. Another smart TV is wall mounted and ready for your use. brbrIf you like to swim or are a sun worshiper, you still haven't explored the best part of this rental: the courtyard and pool. The pool, which is for the exclusive use of Campbell Courtyard guests, is larger than your typical Key West dipping pool. Rather, it is temperature controlled and generously sized by Key West standards. The pool/deck area is ringed with a white picket fence and plenty of foliage to create beauty, privacy, and the kind of tranquil peace of mind only nature can provide. Chaise lounges and chairs sit invitingly right next to the pool. Or if shade is more appealing, claim your spot under the market-umbrella seating area.brbrThe whole set up at Campbell Courtyard is alluring but there's more-a whole storied island awaiting your exploration: the emerald water of the Atlantic and of the Gulf of Mexico, beaches, conch-style houses, Civil War forts, museums, famous hangouts like Sloppy Joe's, Elvis look-alikes, a new waterfront park, and scary sharks at the Aquarium. From your central location on Fleming Street, most things are easily accessible by foot or bike or the free bus service called the Duval Loop. For example, the island's main artery-Duval Street, where you'll find shopping of all sorts, art galleries, tours, open-air restaurants, bars, and much more-is less than two blocks away. Or a few blocks in another direction you'll find the Historic Seaport with more restaurants, tall-ship sunset sails, more watersports opportunities than you could possibly take advantage of, and waterfront restaurants of varying degrees of informality. Set your timer so you don't miss the nightly sunset celebration at Mallory Square where visitors and locals alike gather to applaud as the sun slips below the horizon.brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.
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$446.49

/ Nightly
Condo

Duval Street Suite - Located on Upper Duval

Key West, Florida, United States

It's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. brbrFrom your private and expansive Bahamian-style wraparound balcony, you can sit back in a comfortable Adirondack chair, enjoy a beverage, and take in the day or evening scene below. Duval Street hosts colorful parades, conch train tours, pedicabs, locals, tourists, the rich and famous, kids headed for ice cream at Flamingo Crossing, and sun worshipers headed for the beach. When you've enjoyed watching enough of the goings-on for one sitting, disappear into the residence through any of six French doors. On the front side, four doors open into the living room; on the left side, one door opens into one of the baths; on the right side, one opens into the guest bedroom. brbrWith all four glass doors flung open to the balcony, the living/dining area is flooded with gentle light and tropical cross breezes. Even with the doors closed, this great room is delightfully open and airy thanks to an impressive cathedral ceiling. The lovely stone tile floors add elegance and warmth to the pallet of colors selected for the furniture and accents. A Casablanca-style ceiling whispers above. Below a deep-seated sofa offers comfort, firm support, and the option to convert into an extra queen bed. Flanking the couch are end tables with reading lamps. Close at hand, a wood and glass coffee table makes a convenient resting place for your guidebook or beverage. A comfy arm chair and a TV media chest with four roomy storage drawers complete the living room setting. Wireless high-speed internet, cable, stereo, and DVD player are at your fingertips when you want them. brbrTo the right is the dining area with an elegant glass-top table and six high-back chairs. Here and throughout the residence, cloud white walls make the perfect background for interesting and colorful art work chosen to embellish the ambience. To the left of the dining room is an updated kitchen with handsome blond cabinetry above and below offering plenty of storage space. The room is accented with white tiles and contemporary black appliances. All cooking and serving pieces are provided right down to the corkscrew. One end of the kitchen forms a convenient bar/pass-through to the dining area. brbrBehind the kitchen is the charming front door entry hall with a colorful Welcome sign and table for your keys and other paraphernalia. To the right is what at first looks like a half bath, and it can function that way. Yet immediately around the corner is a generous shower. Not only is this ever-so-convenient setup accessible from the entry hall but also through a door opening into the guest bedroom. The room has a queen bed guaranteed to yield a very restful sleep. Side tables with lamps, a ceiling fan, and a walk-in closet big enough for a whole wardrobe of vacation wear are among the amenities. Again you have the option to open a set of balcony doors to let the incomparable climate and beauty in. brbrSometimes a configuration just makes you feel good and that's certainly true of the master suite at Duval Street. It's in a private loft up highly polished stairs to the left of the living room. Here you'll find a king bed with en suite full bath, generous walk-in closet, and a dresser for your foldable items. And there's a surprise addition-a very private balcony where you can drink your morning latte, read the paper, or sun yourself in as little attire as you choose. No one else can see. This home is Pet (Dog) Friendly**(please see below or our FAQ page for rules and restrictions)brbrWhen you've spent time on your balcony and checked out the rest of your residence, perhaps it's time to explore Duval Street in person. A right turn will head you towards the shores of the Atlantic and a left turn will head you towards the Gulf of Mexico. In between are all the things that make the Conch Republic so famous: beaches, tours, museums, shopping, over two hundred restaurants, bars, and the Key West Aquarium where you can pet a shark if you dare. Or maybe you'd prefer to have your picture taken at the Southernmost Point buoy or pose with a parrot perched on your head. If the arts interest you, you've come to the right town for music, movies, plays, art galleries, lectures, artists in residence, and more. Don't miss the sunset celebration at Mallory Square or the opportunities for all kinds of water sports along the Historic Seaport boardwalk. brbrVisit the beach at Ft. Taylor State Park and claim your spot in the coral sand with a rented umbrella and chaise lounge or just by stretching out your colorful beach towel and plopping down. Maybe snorkel up close and personal with stingrays and tropical fish. When you get hungry or thirsty, a beach concession stand serves beer, food, and snacks. Eat on the deck under an umbrella overlooking the beach. Or bring your own food to enjoy at one of the picnic tables tucked in among shade trees. There are grills, washrooms, changing rooms, outdoor showers, and breathtaking sunsets.brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information. brbr**For Pet Friendly (dog) homes there are restrictions that include, but may not be limited to, the following: pet friendly means dogs, no other animal is permitted. Dogs are restricted to one (1) large dog or two (2) small dogs per stay. Due to Homeowner Insurance restrictions we are unable to accommodate the following breeds: Pit Bull Terriers, Staffordshire Terriers, Rottweilers, German Shepherds, Presa Canarios, Chows Chows, Doberman Pinschers, Akitas, Wolf-hybrids, Mastiffs, Cane Corsos, Great Danes, Alaskan Malamutes, Siberian Huskies nor any mixed breed that contain one of the preceding as part of that mix. Guest is responsible for an additional pet fee of $200.
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Exceptional(2)

$523.0

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Condo

A Beachy View at the Truman Annex in Key West

Key West, Florida, United States

Come and relax in this 2-bedroom 1 bath, first floor with 3 flat screen TV's, custom kitchen, backyard tropical paradise and shared pool right outside the back deck, with free high speed internet service.brConveniently located in the Shipyard Complex of the Truman Annex, right on Southard Street just steps from the active lifestyle of Duval Street, shopping, dining, and night life. Also steps from Mallory Square for gorgeous sunset views and the new Truman Waterfront Park. Assigned off street parking for 1 vehicle. brNO PETS.brPlease note: This property will require a minimum of a 28 night stay.
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$241.68

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SEA-NIC VIEW ~ 2 BR/2Ba Water-front views, Pool Access and Dockage!

Key West, Florida, United States

IT'S A SWELL LIFE…brEndless island treasures engulf this oceanfront haven which is your one stop destination for a complete Key West experience. Peacefully tucked away at the end of a private road, this community overlooks the lively Garrison Bight Marina nestled within nature’s surroundings, offering every imaginable amenity including convenience to shopping, dining and more! Imagine your worries washing away as you get lost in time mesmerized by the sparkling Gulf of Mexico, brimming a with water sports and yachts gently rolling in.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brThis quintessential island retreat is located on the 3rd floor of the complex, possessing a Key West vibe as soon as you step through the front door with tropical views all around. Find a spacious Great Room with an updated and fully equipped kitchen, featuring stainless steel appliances perfect for serving up your home-made meals to enjoy at the dining table for 4 or casually at the breakfast bar for 2. Settle into a good movie with comfy living area furnishings, a flat screen TV (with cable) and 2 sets of French doors that can be perched open for sultry island breezes. Tile flooring and ceiling fans throughout keep this space airy and cool.brbrSLEEPING ARRANGEMENTS…brSnuggle into a king bed within the primary suite with plush linens, a flat screen TV, en suite bathroom with a soaking tub and separate shower, single sleeper convertible ottoman and writing desk for those working remotely. Marvel over your oceanfront views right from your bed and ease the doors open to your private balcony with seating to enjoy your morning cup of coffee with views of the pool and dock. The 2nd guest suite has a queen size bed, steps to a hallway bathroom with a shower tub combo, flat screen TV and direct access to the 2nd veranda overlooking Garrison Bight Marina. Both rooms offer smart TVs so you can connect to your favorite live streaming apps. A queen sofa sleeper resides in the living room area.brbrOUTDOOR LIVING…brEnjoy the rare perk of a private 28 ft. boat slip on the dock just steps from this unit (trailers are not allowed to be stored on property – please inquire for local suggestions). This unobstructed slip allows for seamless navigation out to open turquoise waters. Clean your catch at the dock with a cocktail in hand as the sun sets in the distance and grill up your savory dinner. Dig your toes into the warm, sandy beach and find your serenity with just the sounds of the sea by your side. A refreshing dip in the community pool, a hammock swaying in the breeze and an evening beach bonfire are sure to calm your senses. brbrPARKING...brOne convenient parking spot is available making coming and going ideal.brbrPETS...brNo pets please!brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.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 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). brbrA TRULY REMARKABLE TROPICAL EXPERIENCE AWAITS!
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Exceptional(15)

$382.45

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Condo

Saltwater Angler at The Truman Annex in Key West

Key West, Florida, United States

Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating including large sectional. Twin size sleeper sofa. Dining room and alcove adjoin kitchen; two bedrooms, two full baths, powder room, laundry room. Master bedroom is huge with walk-in air-conditioned closet. Master bath has tub and separate shower, double sink vanity. Second bedroom has twin beds, one with trundle for third bed. Plentiful supply of bed and bath linens. Flat panel televisions in living room and each bedroom. Plenty of closet and storage space. Tile in foyer, halls, kitchen and baths; new laminate flooring in other rooms. Visitors with children are welcome to use children's toys and pool equipment found in master bedroom closet.brPlease note: This property has a 28 night minimum stay
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Exceptional(46)

$316.91

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Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Key West, Florida, United States

This condo is located approximately three miles from Duval and one mile from Smathers beach. Walking distance to the Ocean. Grocery stores, marina, and water sports nearby. Outdoor spa, Gym, Private balcony, Tennessee court.
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Exceptional(46)

$192.25

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Shady Nook at The Truman Annex in Key West

Key West, Florida, United States

This first floor 2 bedroom, 1 bath condo is a blend of Key West charm, modern comfort and unbeatable location!brYou'll enjoy bright, breezy interiors, serene outdoor spaces, a communal pool and walkable access to the best of down town. Perfect for a vacation escape. This is a ground level condo. One of the bedrooms has a queen size bed, the other has two twins - both bedrooms are equipped with a flat screen TV.brThe unit has free Wi-Fi, cable TV & streaming capabilities, one parking space, a fully equipped kitchen. Beach towels are included! The unit will accommodate up to 4 adults comfortably. The dining table only seats 2, however the patio set is set up with dining for 4 adults. brCome and enjoy the best of Key West!brPlease note: This property has a 28 night minimum stay
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