Home Vacation Condo Rentals By Owner In Key West, FL

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$669.38

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WATERFRONT PENTHOUSE! Galleon Resort Key West, Sleeps 6, Private Beach

Key West, Florida, United States

WEEK 39 PENTHOUSE UNIT D-51 ! 9/26--10/3/26.brEnjoy 7 nights in downtown Key West at The Galleon Resort!brbrThe Galleon Resort is located in the heart of Old Town Key West in the Historic Seaport District. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, hot tub, with a restaurant and tiki bar. Relax in the hot tub or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.brbrMel Fisher Museum, Mallory Square and Duval St are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum is 1 mile away.br.brWe have one week to offer in 2026 with guaranteed unit number as follows:brWeek 39, 9/26--10/3 is Unit D51 PENTHOUSE marina side unit. The 2nd bdrm here has two twins that can be pushed together to make a queen.brbrOverlooking the marina and historic seaport. This two bedroom condo sleeps six, and features a fully equipped kitchen. The primary suite has a king size bed, jetted tub, shower, two vanity sinks and large closets. The guest bedroom features either two twins and has access to the full guest bathroom with a shower. The living room has a TV with cable, dining area for six, and a queen sleeper sofa. Large balcony from the living room overlooking all of the boats & restaurants in the marina.brbrOther than the rent paid to VRBO, there will be a $80 resort fee to be collected by the front desk upon check in. This is in addition to the rent already paid. A $150 refundable security deposit is also secured on your credit card and is released by resort after checkout as long as no damages occur during your stay.brbrOne free mid week cleaning! Housekeeping changes linens and towels on Wednesday only at no additional charge. If daily housekeeping is desired, there is an additional fee imposed by the resort.brbrParking for one vehicle, per unit only. No oversized vehicles, RV's or trailers are allowed to park on property. Parking is extremely limited and multiple vehicles are not able to be accommodated.brbrMinimum Age: 21 years oldbrPet Policy: No PetsbrAn ID and credit card for a refundable security deposit will be required.brCheck-in is after 4 pm;brcheck-out by 10 am.brNo Smoking. Penalties will apply.brNon-Refundable Cancellation and Refund Policy:br$80 Resort Fee Due at Check-in *Pricing Subject to changebrGuest check-in certificate will be email to you directly from the resort once VRBO releases full payment to me, the owner.brPlease look over the lease document uploaded in VRBO.brbrNote that we do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service. Trip/Vacation insurance is highly recommended and may be included as part of VRBO's fees.brbrPictures are representative of the unit, layout and decor may vary.
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Exceptional(4)

$202.02

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Stunning Ocean View 2BR/2BA Condo in Exclusive 1800 Atlantic Community

Key West, Florida, United States

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.brbrbrbrbrStunning Ocean View 2BR/2BA Condo in Exclusive 1800 Atlantic CommunitybrbrWelcome to your beautifully renovated, second-floor oasis in the prestigious 1800 Atlantic community in Key West. This stunning 2-bedroom, 2-bathroom condo features custom tile work throughout, an expansive private balcony, and breathtaking views of the Atlantic Ocean and lush gardens.brbrThe primary suite includes a luxurious king-sized bed, while the guest bedroom offers two twin beds that can be converted into a king upon request—ideal for families or couples traveling together. A queen sleeper sofa in the living room adds extra sleeping space, and all rooms are furnished with brand-new beds for maximum comfort.brbrThe fully equipped kitchen, in-unit washer and dryer, high-speed internet, and cable TV ensure all the conveniences of home. A dedicated desk area allows you to send a postcard or take care of work while away.brbrStep out onto your private balcony and enjoy al fresco dining with ample seating and tranquil views of nature and the ocean. Relax in the Olympic-size heated pool, unwind in the large hot tub or sauna, or take advantage of the lighted tennis courts and nearby beach access.brbrLocated close to Key West’s vibrant nightlife, city center, and airports, this condo blends the perfect balance of serenity and accessibility. Ideal for families, couples, or business travelers, this property is available for monthly rentals.brbrResort-Style Amenities Include:br Heated Olympic-size pool & jacuzzibr Sauna & tennis courtsbr Lush tropical landscapingbr Secure, exclusive community settingbrbrYour tropical escape awaits—book your stay today!
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Exceptional(1)

$478.65

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Atlantic Parrot | Oceanfront Condo w/ Pool

Key West, Florida, United States

This vibrant beachfront condo is the perfect home base for soaking up the sun and sea breezes of Key West. Located directly along the shoreline, this colorful coastal escape pairs relaxed island style with unbeatable ocean views, creating an inviting retreat just moments from beaches, bike paths, and iconic island attractions. With resort-style amenities and a private balcony overlooking the water, this condo sets the tone for a memorable Florida Keys getaway.brbrThe Ambiance:brDesigned with an open and airy layout, this fourth-floor condo offers plenty of space to unwind after a day in the sun. Step out onto your private ocean-view balcony to enjoy morning coffee or sunset skies over the Atlantic. Inside, the living area is bright and welcoming, complemented by a fully equipped kitchen and updated furnishings. The cheerful décor and beachy palette reflect the laid-back rhythm of island living.brbrGuest Perks:brGuests enjoy access to a variety of shared resort amenities, including a large outdoor pool, relaxing hot tub, fitness center, and on-site tennis courts. A digital E-lock provides secure, contactless entry with a unique code for each stay. The condo includes air conditioning, WiFi, and one designated parking space in the building's garage (parking fees apply). Whether you're lounging poolside or heading out for a day of adventure, convenience is built into every detail.brbrNeighborhood Highlights:brWith the Florida Keys Overseas Heritage Trail right outside the building, exploring the island is effortless. Bike or walk to Smathers Beach just steps away, or head west to the popular spots at Higgs Beach, including the pier and historic West Martello Tower. Old Town Key West attractions like the Ernest Hemingway Home and Museum and Mallory Square are just a short drive away, offering endless dining, shopping, and cultural experiences.brbrGetting Around:brOne vehicle parking is available on-site for an additional fee, making day trips and excursions simple. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the property. This area is ideal for biking and walking, with direct access to scenic paths along the beach. Guests can easily reach beaches, parks, and attractions without needing to drive far. Feel free to ask for local recommendations!brbrOther Things to Note:br- This home is located in a noise-sensitive area and participates in a Good Neighbor programbr- Quiet hours are enforced from 10:00 p.m. to 8:00 a.m.br- No smoking is permitted anywhere on the premisesbr- No pets are allowedbr- Guests must be 25 years of age or older to rentbr- This rental is located on the 4th floorbr- One parking space is available for a feebrbrCheck-in time is 3:00 PMbrCheck-out time is 11:00 AMbrbrBook your stay today and enjoy beachfront living with resort-style amenities in one of Key West's most scenic coastal locations. Whether you're here to relax by the pool, bike along the shoreline, or explore the island's historic charm, this colorful oceanfront condo offers the perfect blend of comfort, convenience, and coastal adventure.brbrAt Colocada Vacation Rentals, we're committed to providing a smooth, relaxing, and unforgettable Key West experience. Have questions or need local tips We're always happy to help make your stay
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$182.96

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Authors Retreat - Downtown Key West

Key West, Florida, United States

This 2 bedroom, 1 ½ bath condo in the Campbell historic building offers a new translation for the word “vacation.” The vocabulary begins behind a white picket fence with a courtyard of cozy cottages nestled around a sparkling pool. The setting is perfect as a postcard: quiet yet located two blocks from Key West’s world-famous Duval Street. Walking, biking, a pedi-cab, or uber work nicely as ways to get around. A coveted parking space for one small vehicle (must be under 16 ft.) is provided. brbrThe story starts at the compound gate. Right inside is a bike rack and lots of green and flower plantings to remind you that you are in paradise. A few steps more bring you to the entrance of this residence. If you turn around, you get the full aha! view of the shared pool. Straight head is the small porch area and another larger, quite charming porch to the side. brbrOnce inside the door, you’ll find the living and dining area which has plenty of natural light, high ceilings, and a glass brick accent wall reflecting light back into the room. There’s plenty of comfy couch and chair seating to make a congenial conversation area. If you are more up for being entertained, there’s a smart TV w/ high speed internet access perfectly positioned for streaming from the seating arrangement. It is equipped with the YouTube TV streaming service which includes the typical expanded basic 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 accounts. The flatscreen TV sits on an artisan, three-shelf cabinet with ratan-weave doors. The shelves provide space for important things that you want close at hand but don’t want creating clutter in the open. Also in one corner is a table and chairs suitable for meals or for playing cards or board games. Overhead a ceiling fan creates tropical ambience and air circulation. Of course there’s central AC, high-speed internet, three flat-screen TVs, with efficient and attractive ceiling fans throughout. brbrNext in the floor plan is a guest half bath. Then comes the full bath opening out to the den. Here also is a second streaming TV sitting on a roomy storage cabinet. A wardrobe provides room for clothing and office supplies. A daybed provides extra seating or a comfortable accommodation for a third guest. An upholstered conference chair with arms provides the perfect place if someone wants to consult or chat. Also a bookcase stands nearby. It’s a compact, multifunctional room with many windows letting in plenty of Key West’s naturally beautiful light. brbrNext comes the King bedroom again flooded with natural light. A chest with many drawers stands ready to store whatever you need stored and serves as a perch for the third TV. A closet for hanging this and that is partially formed by the unique glass brick wall. brOn to the kitchen…all the appliances you’ll need for cooking and cleanup are supplied in stainless. Cabinets and shelving above and below help avoid clutter. Pots and Pans are artistically hung from the ceiling, as are utensils on the wall. The windows give glimpses of the soothing pool just outside. Faustos, a local grocery store since 1926, is less than a block away if you want foodstuffs to fill up the refrigerator or pantry. All appliances are new in 2024. Or maybe the kitchen will be mostly for warming left overs from meals out at one of the island’s myriad eating establishments.brbrIf you like to swim or are a sun worshiper, you still haven’t explored the best part of this condo: the courtyard and pool. The pool, which is for the exclusive use of Campbell Courtyard guests, is no small dipping or cocktail pool as is prevalent in Key West. Rather, it’s heated (in winter) and generously sized. The pool and deck area are ringed with a white picket fence and plenty of tropical foliage to create beauty, privacy, and a kind of tranquil peace-of-mind that only nature can provide. Chaise lounges and chairs sit invitingly next to the pool, as does a dining table and chairs. If shade is more appealing, claim your spot under the gazabo-style seating area at one end.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, an expansive waterfront park, and sharks for petting at the Aquarium. From your central Old Town location, most things are easily accessible by foot or bike or the Duval Loop bus. 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.brbrA few blocks in another direction you’ll find the Historic Seaport with tall ship sunset sails and water sport opportunities like diving, fishing, parasailing, snorkeling, jet-skiing, and more. Or try one of the waterfront restaurants that ring the harbor. Set your timer so you don’t miss the nightly Sunset Celebration at Mallory Square where visitors and locals alike gather to applaud gently as the sun slips below the horizon. It’s a MUST experience.brbrMaybe your taste runs more towards the arts. If so, you’re in the right place for music, movies, plays, art galleries, lectures, and more. If you like beaches, your accommodations are within biking distance to a favorite locals’ beach, Fort Zachery Taylor, where you can rent chairs, umbrellas, and snorkeling equipment. Bathrooms, showers, a snack bar, and picnic tables are also available. Or maybe you’ll decide to skip the beach in favor of exploring the adjacent Civil War-era fort, which was designated a National Historic Landmark in 1973.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. Campbell Courtyard COA does NOT allow renters to have pets.
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$287.54

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Sun, Sea, & Citrus - Bright 2-Bedroom Monthly Rental in Old Town Key West with Private Pool. Sleeps 5-6

Key West, Florida, United States

Our guests are in for a treat at such a bright and beautiful entire first-floor unit in Key West. This inviting two-bedroom bungalow is perfectly situated on a calm and quiet street in Old Town, yet just steps from the historic cemetery and a stroll from ever-buzzing Duval Street. You’ll also have your own off-street parking within the property’s gate, perfect for a smaller vehicle or your golf cart for further cruises (contact our concierge to help you arrange all your rental needs).brbrThe unit itself shines with fun color and vaulted, sunlit interiors. Rocking chairs await you on the front porch, and a sparkling private pool and grill are all yours to enjoy out back. The vibrant citrus orange kitchen is as energizing as a Cuban coffee, and comes fully equipped with a stainless steel refrigerator/freezer and all the cooking essentials. Gather around the dining table for a homemade meal or favorite Key West take-out, then mix a drink under the neon cocktail sign at your personal mini bar.brbrThe open living room is airy and easygoing, with a comfy pull-out sofa ready for weekend visitors or kids tagging along on a longer stay. On either side of the living space, you’ll find two king bedrooms, each designed for maximum comfort and reprieve. Both feature plush king-sized beds, smart TVs, closets, and split-unit ACs to personalize your climate control. The primary suite has immediate access to the pool deck and a sun-drenched en-suite bath. Another full bath is available to the other bedroom and common area.brbrBright, spirited, and simple, this Angela Street retreat is a fantastic place to call “home,” throughout your Key West trip. We look forward to making sure you have a great stay at Sun, Sea, & Citrus. brbrRestrictions: Smoking permitted only outside please. No pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.
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Exceptional(9)

$669.86

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TortugasHarbor 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 Views.brbrbrbrThe Space:brbrEscape the Ordinary...brbrbrbrThe Tortugas Harbor 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 1930s Historic Key West building, offers a private exterior entrance and a spacious front 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 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•           Amazing second floor porch with seating areas and pool and garden 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 Tortugas 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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Exceptional(14)

$823.15

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American Shoal Light Suite

Key West, Florida, United States

Summary:brbrLuxury 2BD/1BA Suite with Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Patio.brbrbrbrThe Space:brbrEscape the Ordinary....brbrbrbrThe American Shoal Lighthouse Suite offers separate King and Queen bedrooms and was completely refurbished in 2024 that can sleep up to 6 guests. This beautifully appointed ground floor suite, located in a renovated 1930’s Historic Key West building, offers a private exterior entrance and a spacious private outside patio area offering Key West Lighthouse 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 and queen beds with premium linensbrbr•           Full sized sectional couch with pull out bedbrbr•           Fully equipped kitchen with granite countertopsbrbr•           Spa quality stone rain shower bathroombrbr•           Hardwood flooring throughout the suitebrbr•           Spacious back porch with dining tablebrbr•           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 American Shoal 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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Exceptional(23)

$194.31

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**SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSERENITY ON SOUTHARD is a beautifully renovated 1 bedroom second floor condo with a full kitchen and washer and dryer. This condo is located in the Truman Annex, a gated community located in the heart of the island - just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have a peaceful retreat within a private gated community. Combined with Last Key Realty’s renowned Five-Star Guest Services, SERENITY ON SOUTHARD is an idyllic home base for your stay in paradise.brbrTHE LOCATION...brbrTruman Annex is a private, gated community right in Old Town, Key West. You'll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town, yet you'll benefit from the peace and quiet that Truman Annex is known for. Although you won't need a car to get around from this excellent location, there is a reserved off-street parking space.brbrTHE LIVING AREA...brbrThe living room of has a large set of French doors so you can enjoy those wonderful tropical breezes, and a large flat screen TV for those evenings when you need a break from the excitement of Old Town. The kitchen has everything you’ll need to prepare meals at home. Across from the kitchen is a versatile multi-level counter with bar seating and a work space with an office chair. You'll be able to dine outside on the sunny back deck using the outdoor dining set with seating for four.brbrTHE COMMUNITY POOL & FORT ZACHARY TAYLOR STATE PARK...brbrThe community pool is located just around the corner, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile from your front door. The entrance to Truman Annex is secured by a 24-hour staffed guard gate and you can use the residential entry gate keys to come and go on foot at night.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE ACCOMMODATIONS...brbr** Master Suite: King bed, flat screen TV, and access to the hall bathroom with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchen (no dishwasher)br** 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 includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Assigned Off-street Parking for 1 Car (with vehicle restrictions - no vehicle over 18’ long or 80’’ wide)brbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 2 adultsbr** No Pets Allowed
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Exceptional(13)

$703.06

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Grand Marina Suite - Poolside & Waterfront Condo

Key West, Florida, United States

Summary:brbrA beautiful oceanfront suite located at the best marina in the Keys. Situated on the glistening Atlantic Ocean, our Grand Marina Suite is a tranquil respite with on-site access to boat dockage and world-class fishing charters. Located minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate lodging experience unlike any hotel.brbrbrbrThe Space:brbrGrand Marina Suite is a full two-bedroom suite, with a full kitchen, living room and outdoor lanai. Each of the two bedrooms feature luxurious king sized beds and en suite bathrooms. There is a sleeper sofa in the living room. Outside of the Suite, our guests are encouraged to take advantage of our on-site pool, beach, sauna and fitness center.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrOur property is secluded and private yet minutes away from the excitement of Key West. This condo is located at the private Key West Harbour Marina, in Stock Island, the authentic and revitalized fishing and arts community located directly east of downtown Key West.brbrbrbrGetting Around:brbrArrive by boat, plane or car. On-site golf cart rentals are available, or take advantage of the many taxi and ride-sharing services available for short trips around Key West.brbrbrbrThere are assigned parking spots in front of the Harbour Residences marked as Condo 1, Condo 2, or Condo 3. You have 2 private parking spots located in front of your unit included with your stay.brbrbrbrOther Things to Note:brbr-For the purpose of creating a safe environment for our guests, the exterior of the building is monitored by security cameras.brbr-Please note the onsite restaurant is no longer open.brbr- Not pet friendly
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Bath 2

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$491.64

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

Key West, Florida, United States

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

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Exceptional(32)

$696.82

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Grand Marina Suite - Poolside & Waterfront Condo

Key West, Florida, United States

Summary:brbrA beautiful oceanfront suite located at the best marina in the Keys. Situated on the glistening Atlantic Ocean, our Grand Marina Suite is a tranquil respite with on-site access to boat dockage and world-class fishing charters. Located minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate lodging experience unlike any hotel.brbrbrbrThe Space:brbrGrand Marina Suite is a full two-bedroom suite, with a full kitchen, living room and outdoor lanai. Each of the two bedrooms feature luxurious king sized beds and en suite bathrooms. There is a sleeper sofa in the living room. Outside of the Suite, our guests are encouraged to take advantage of our on-site pool, beach, sauna and fitness center.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrOur property is secluded and private yet minutes away from the excitement of Key West. This condo is located at the private Key West Harbour Marina, in Stock Island, the authentic and revitalized fishing and arts community located directly east of downtown Key West.brbrbrbrGetting Around:brbrArrive by boat, plane or car. On-site golf cart rentals are available, or take advantage of the many taxi and ride-sharing services available for short trips around Key West.brbrbrbrThere are assigned parking spots in front of the Harbour Residences marked as Condo 1, Condo 2, or Condo 3. You have 2 private parking spots located in front of your unit included with your stay.brbrbrbrOther Things to Note:brbr-For the purpose of creating a safe environment for our guests, the exterior of the building is monitored by security cameras.brbr-Please note the onsite restaurant is no longer open.brbr- Not pet friendly
Bed 2

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Bath 2

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Exceptional(21)

$696.75

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Grand Marina Suite - Poolside & Waterfront Condo

Key West, Florida, United States

Summary:brbrA beautiful oceanfront suite located at the best marina in the Keys. Situated on the glistening Atlantic Ocean, our Grand Marina Suite is a tranquil respite with on-site access to boat dockage and world-class fishing charters. Located minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate lodging experience unlike any hotel.brbrbrbrThe Space:brbrGrand Marina Suite is a full two-bedroom suite, with a full kitchen, living room and outdoor lanai. Each of the two bedrooms feature luxurious king sized beds and en suite bathrooms. There is a sleeper sofa in the living room. Outside of the Suite, our guests are encouraged to take advantage of our on-site pool, beach, sauna and fitness center.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrOur property is secluded and private yet minutes away from the excitement of Key West. This condo is located at the private Key West Harbour Marina, in Stock Island, the authentic and revitalized fishing and arts community located directly east of downtown Key West.brbrbrbrGetting Around:brbrArrive by boat, plane or car. On-site golf cart rentals are available, or take advantage of the many taxi and ride-sharing services available for short trips around Key West.brbrbrbrThere are assigned parking spots in front of the Harbour Residences marked as Condo 1, Condo 2, or Condo 3. You have 2 private parking spots located in front of your unit included with your stay.brbrbrbrOther Things to Note:brbr-For the purpose of creating a safe environment for our guests, the exterior of the building is monitored by security cameras.brbr-Please note the onsite restaurant is no longer open.brbr- Not pet friendly
Bed 2

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Bath 2

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Exceptional(18)

$256.53

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Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool

Key West, Florida, United States

Welcome to Pierre's Perch, a beautiful second-floor studio that blends modern design with tropical charm! brbr brbrLocated in the historic Galleria, once a haven for Key West’s traveling artists, this tranquil oasis includes a peaceful pool area and a spacious sundeck perfect for unwinding. Nestled in the heart of Bahama Village, a vibrant, residential neighborhood just blocks from Duval Street, you’ll be surrounded by Bahamian-inspired charm and within walking distance to iconic attractions like the Southernmost Point, Key West Lighthouse, and the Earnest Hemingway Museum. Whether you’re here to relax, explore, or find inspiration, Pierre's Perch offers the perfect home base for your Key West adventure! brbr brbrSLEEPS MAXIMUM OF 2 GUESTS: brbr brbrBedroom: Queen Bed, Flat Screen TV brbr brbrKitchenette: Lightly Equipped (mini refrigerator/freezer, sink, two-burner stove, microwave and Keurig) brbr brbrAMENITIES: brbr brbr- Shared Heated (Nov-Apr) Pool brbr brbr- Shared Laundry brbr brbr- Shared Bike Rack brbr brbr- Shared Propane BBQ Grill brbr brbr- Keurig brbr brbr- Linen's and Bath/Beach Towels Provided brbr brbr- Street Parking available, no off-street/designated parking available brbr brbr- 2.5 blocks to Duval Street brbr brbr- 0.4 miles to Southernmost Point brbr brbr- 0.7 miles to Fort Zachary Taylor State Park/Beach brbr brbr- 1.1 miles to Mallory Square Sunset Pier brbr brbr- 1.2 miles to Key West Historic Seaport brbr brbr- 2.6 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrUnit Size: Please be aware, this unit is a cozy 115 sq. ft. studio—while compact, it provides all the essentials for a comfortable and enjoyable stay. brbr brbrAge and Occupancy Requirements: Booking tenant must be 25 years of age or older and must occupy the property for the entire duration of the booking. Furthermore, this property is exclusively available as a vacation rental and is not available for worker housing. brbr brbrNo Smoking: Smoking is strictly prohibited within the property to maintain a smoke-free environment for all guests. brbr brbrNo Pets: Pets are strictly prohibited within the property to maintain a pet-free environment for all guests. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of guests and property, exterior security cameras monitor all exterior areas of the complex. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.
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$1388.54

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GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

Key West, Florida, United States

YOUR OCEANFRONT OASIS AWAITS...brThis remarkable and magical retreat is sure to provide all the R & R you need to refresh your soul. Peacefully located in Key West Beach Club community just minutes to downtown and Duval Street. This sweet and newly renovated haven encompasses every conceivable amenity you could desire while in Paradise.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrPLEASE NOTE...brThis home has a 6 night minimum as required by the HOA of the community. The renter will be asked to send photos of all adult guests upon booking as required by the HOA.brbrDETAILS AND AMENITIES...brLocated at the top floor of this desirable community, this unit is sure to take your breath away as soon as you walk through the front door. Find a bright and open space with natural lighting pouring through a multitude of windows with cool tile and hardwood flooring throughout and soaring ceilings creating a cheery gathering space. A fully equipped kitchen allows for seamless mealtime prep with convenient bar top seating for 4 and an indoor dining table for 6. Cozy living room furnishings are steps away with a TV and breathtaking views of your ocean front porch beyond. Enjoy a writing desk for those working remotely! This home is 0.2 miles from Higgs Beach and 0.8 miles from Smathers Beach.brbrSLEEPING ARRANGEMENTS...brFind a primary suite steps from the living area with a king bed, TV, en suite bathroom with a shower and direct access to the outdoor balcony. Another king guest room resides on the 1st level with a TV and hallway bathroom nearby with a shower. Head up to the 2nd floor to find a room with 2 twins that can convert to a king with a TV and another king guest bedroom - both with TVs and a shared hallway bathroom with a shower. A sofa sleeper occupies the living area for additional sleeping arrangements. brbrOUTDOOR LIVING...brCatch a breath of fresh air out on your private and spacious outdoor balcony with priceless views of the sparkling, turquoise ocean beyond. Enjoy plentiful seating as you hear the tranquil ocean waves below and soak up island life. Two pools reside on property with a community grill, tennis court, fitness area and elevators to this unit. This property is just a stone's throw to White St. Pier, Salute on the Beach restaurant and a short drive, bike ride or Uber into town. Higgs Beach is down the walking path from this community 0.4 miles and Smathers Beach is 1 mile in the other direction! Pickle ball and tennis courts are across the street from Higgs Beach.brbrPARKING...brThere is access to one parking spot on property, and plenty of street parking is available in this area for any additional vehicles. No vehicles over 18' long or over 80 wide. brbrPETS...brThis is not a pet-friendly home.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrGuests are only allowed to check-in on premises between 8:00 A.M. and 11:00 P.M.brbrAN UNMATCHED EXPERIENCE...
Bed 4

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Exceptional(37)

$693.33

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Spectacular Ocean View Amazing quality- Massage Chair. Newly renovated

KEY WEST, Florida, United States

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.brbrbrbrBlue HavenbrbrAn Exquisite Oceanfront Penthouse in Key WestbrWelcome to Blue Haven — Your Premier Oceanfront EscapebrbrNestled on the pristine shores of Key West, Blue Haven is the ultimate luxury penthouse condominium, offering breathtaking direct ocean views and an unmatched vacation experience.brAbout the Penthousebrbr Completely remodeled with over $750,000 in upgradesbr Floor-to-ceiling windows framing panoramic ocean vistasbr Spacious open-concept living with designer touches and modern elegancebr Gourmet kitchen with custom cabinetry and top-tier appliancesbrbr Relaxation & entertainment: zero-gravity massage chair, 80” smart TV, Sonos sound system, Nintendo Switch, and board gamesbrbr Master suite & guest rooms with private balconies and ocean viewsbr Business-ready with fast internet and dedicated work-spacesbrbrAmenities & Featuresbrbr Direct ocean views from every roombr Full kitchen, dining, living areasbr 2 bedrooms (king bed & twin beds), 2 bathrooms, queen sofa bed, plus powered blow-up mattressesbr Air-conditioned throughoutbr Washer/dryer, hair dryers, smart TVs in bedroomsbr Assigned covered parking (standard size vehicle)brbr Access to 1800 Atlantic Complex amenities: botanical gardens, Olympic-size pool, 20-person Jacuzzi, tennis courts (clay & hard), fitness center, ping pong, library, grilling stations, and more
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Exceptional(21)

$493.78

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Truman's Hideaway | Top Location w/ Patio, Pool Access & BBQ | Month Long Stays

Key West, Florida, United States

*Please read before booking:*brConstruction on the Annex Building spalling project will begin on April 1st. The project is expected to take approximately four to five months to complete. Please be advised that work may be noisy at times, and scaffolding will be erected in front of certain units. Please exercise caution while crews are active on the property.brbr*Please note that this home is available for 28+ night stays only.*brbrIt’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch.brbrThis lovely Truman Annex condo rental in the exclusive Harbour Place condominium complex offers all the comforts of home with the special touches that make it a vacation worth remembering.brbrThe colorfully decorated living room/dining room area, showcases tropical art. A fully equipped kitchen has everything at hand if you decide to cook. A whimsical wall mural of dogs enjoying water sports adorns the master bedroom with king bed along with a cozy sitting area, perfect for curling up with a good book. A queen guest bedroom and a second bathroom with tub and shower are provided.brbrEnjoy the large shared pool with a spectacular view or head to close-by Fort Zachary Taylor State Park for a swimming/snorkeling adventure or a shady picnic by the sea.brbrTruman Annex is a gated community within the Old Town section of Key West within walking distance of anything you'll want to do while visiting -- Sunset Celebration at Mallory Square; Duval Street with its bars, restaurants, art galleries, and shopping; historic attractions such as the Hemingway House, Lighthouse Museum, Customs House, and the Mel Fisher Museum. So many options, so little time!brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- This home has access to a shared pool.br- This home is located in a gated community.br- This home features a sleeper sofa.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- The Harbor Place HOA is doing extensive renovations on the exterior of the Condominiums. They are attempting to soundproof the noise the best they can, and at times part of the deck adjacent to your rental may be unavailable for use. This will affect reservations between August and December 2023.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed w/ ensuitebrBedroom 2 / Queen bedbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.
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Exceptional(22)

$527.14

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Oceanview at 1800 Atlantic, short walk to Smathers Beach wish Island Paradise

Key West, Florida, United States

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.brbrbrOceanfront Luxury at 1800 Atlantic – 2-Bedroom, 2-Bath CondobrbrWelcome to your perfect Key West retreat! This beautifully appointed 2-bedroom, 2-bath condominium is fully tiled and designed for comfort and relaxation.brbrThe spacious primary suite features a king-size bed and an en-suite bathroom with a walk-in shower. The guest bedroom offers two twin beds that can be seamlessly converted into a king, making it ideal for families or couples. Both bedrooms — along with the living room — open onto a stunning 40-foot private balcony with direct views of the Atlantic Ocean.brbrEnjoy a fully equipped kitchen, perfect for preparing meals with ease, and the convenience of a full-size washer and dryer right in the unit. Step out onto the balcony to watch boats and water-sport activities glide across the water — the ultimate way to unwind.brbrResort-Style Amenitiesbrbr1800 Atlantic is packed with features to elevate your stay:brbr Olympic-size heated pool – perfect for laps or loungingbr 20-person Jacuzzi and poolside saunas – for total relaxationbr Lighted tennis courts, including the island’s only clay courtbr Fitness center, business center, and librarybr br Covered picnic areas with charcoal grills — ideal for grilling your fresh catch in the lush garden courtyardbrbrWhether you're looking to relax or explore, this condo offers the perfect blend of comfort, convenience, and coastal charm.
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Exceptional(31)

$590.59

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Sundown Refuge | Top Location w/ Outdoor Dining & Shared Pool | Month Long Stays

Key West, Florida, United States

*Please read before booking:*brConstruction on the Annex Building spalling project will begin on April 1st. The project is expected to take approximately four to five months to complete. Please be advised that work may be noisy at times, and scaffolding will be erected in front of certain units. Please exercise caution while crews are active on the property.brbr*Please note that this home is available for 28+ night stays only.*brbrView passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!brbrBalmy breezes, brilliant sunrises, and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex. You'll spend most of your time overlooking Florida Bay in one direction and Truman's Little White House in the other from the privacy of your own spacious deck.brbrThe living and dining areas are decorated in soothing tones of green and beige and tastefully furnished with a plethora of local artwork with all the necessities of home. You'll wonder how you'll ever leave!brThe master bedroom with a king bed and bathroom en-suite and the queen guest bedroom opens to the deck, offering lots of opportunities to congregate with a large group or keep it intimate with your morning coffee.brbrOnce you do leave the comforts of this home, anything you'll want to do is close by – the nightly Sunset Celebration at Mallory Square, dining and shopping galore on Duval Street, and many historic attractions within easy walking distance. Spend time relaxing by the refreshing pool or ride your bike to Ft. Zachary Taylor State Park for some swimming and snorkeling at Key West’s nicest beach. Life is good at Sundown Refuge!brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr​​​​​​​*Home Truths:*br- This home has access to a shared pool.br- This home is located in a gated community.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- The Harbor Place HOA is doing extensive renovations on the exterior of the Condominiums. They are attempting to soundproof the noise the best they can, and at times part of the deck adjacent to your rental may be unavailable for use. This will affect reservations between August and December 2023.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed w/ ensuitebrBedroom 2 / Queen bedbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.
Bed 2

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Bath 2

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Sleep 5

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