Vacation Condo Rentals By Owner In Key West, FL

Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and dining area. The living room features comfy furniture and a panel TV. One queen bedroom and one twin bedroom. Enjoy outdoor dining on the brick patio surrounded by a tropical landscape. brVilla Fleur is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former U.S. Navy property of Truman's Little White house. Just steps from Duval St. and located near the Ft. Zach beach and Hemingway's house, all of Old Key West's sites are within easy walking distance. Our private oasis can be your tropical retreat. brbrCOVID-19 UPDATE after May 1, 2020. Please note our 60 day refund policy. We will no longer offer a cash refund after the 60 day period has passed. We will offer a credit if local authorities issue travel restrictions that prevent your visit to Key West.

Villa Fleur at Shipyard Condominiums

Key West, Florida, United States

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$306.97

The Jungle Breeze condo at LaBrisa Condominiums.br*Ocean Viewbr*Free WiFibr* Free Covered Parkingbr* Final cleaning included in pricebr* KING size bed.br* Accommodates 2 adultsbr* Recently renovated this condo features all new flooring and a brand new kitchenbr* Full size washer and dryer. brbrThis is not a hotel; it is a privately owned condo facing the ocean with a view of swaying palms and turquoise waters. The Jungle Breeze condo is the perfect getaway for a romantic couple or a small family. The Jungle Breeze condo features a fabulous view of the ocean and the beach.brbrThe road construction around the condominium property mentioned in reviews has been completed as of February 2022, there are still road construction projects happening around the island but none that affect this property. brActivities and Attractions : At Smathers beach you will find available such activities as windsurfing, sail boarding, snorkeling and kayak or Jet Ski tours. Old Town, Key West and Duval St are about 1mile away and there you will find dozens of restaurants, famous bars, art galleries, museums, live theater, boutique shopping and tours available on both land and sea. Key West is a bicycle friendly town and this is a great option for touring our small island of 2 miles by 4 miles.brbrCovid 19 : the mask order in Key West has been rescinded but you will find some businesses do require a mask to enter their premises so please always carry a mask with you. Residents of LaBrisa Condominiums may be required to wear a mask on the elevator if there have been reported cases of Covid on the property. brThank you,brPam MacKenzie

Your Condo by the Beach with Ocean View

Key West, Florida, United States

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Bath

Sleeps

$354.91

We are moving to a monthly rental model and passing on the savings to you. Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always received great reviews on cleanliness. There will always be disinfectant wipes, liquid hand soap, dish detergent, laundry detergent, dishwasher tablets and a multitude of other cleaning supplies available for your use during your stay. It’s not just a place on the map, it’s a frame of mind, an Attitude…… come and let us share that Key West Attitude with you. This is not just a rental but OUR VACATION HOME too. You will find that it is a very well appointed. Included in your stay is the use of our 2 bicycles, there are Smart TV's in the living area and King bedroom and a Flat Screen in Queen bedroom all with HD Cable, Wi-Fi, secured high speed internet, secured assigned parking for 1 vehicle only, enjoyment of the common areas and the use of the pool, which is approximately 100 paces from the back gate. Located in the Ship Yard of Truman Annex a luxury community in the heart of Old Town Key West within walking distance to most places you want to visit. This is a 1st floor unit that boasts 2 sets of hurricane rated French doors opening onto a quaint private paradise with lots of palm trees for that private tropical oasis feeling. A dining table with seating for four and overhead fans await your arrival. Dimming lights to set the mood inside and out. This air conditioned/heated unit has been decorated using bright citrus accents and lively art work (most of it original and local). We have quality linens, and furnishings. The bathroom features a Couples Shower and a comfort height toilet, the vanity and over sized mirrored medicine cabinet offer lots of storage. In the well appointed kitchen you will find stainless steel appliances, high end ultra quiet dishwasher, Fridge with icemaker, smooth top stove and everything that you will need to prepare and serve a nice meal if you are so inclined. The King bedroom features a memory foam mattress on a custom bed frame that offers a storage area for luggage and other large items during your stay and a Smart TV. The Queen room features a Beauty Rest -Recharge Queen mattress for your comfort, Flat screen TV with double French doors onto the back deck. The Living/Dinning area offers a table with seating for four, leather sofa, 2 accent chairs, Smart TV with HD cable and small shelf stereo. You are located off the street in a lovely quiet part of the Shipyard only paces from the parking lot and pool. There is no vehicle traffic and the pedestrian traffic is limited . The back deck features over head fans, landscape lighting, a gas grill and dimming lights. Only a short walk from Duval St, Sunset at Mallory Square, Fort Zachary Taylor State Park and Beach, the infamous Green Parrot Bar, the Key West Coffee Butler Amphitheater and playground ... the list goes on.... enjoy the vibrant life of Key West and know that you have your very own sanctuary to return to. Experience Key West like a local on our personal bicycles 1 ladies and 1 men's equipped with quick adjust seats and lights…. this is definitely the best way to get around Key West, no need to fight for a parking spot, relax, wander the side streets and get that Key West Attitude like the locals. Please note that smoking and pets are NOT permitted in the condo. Smoking is permitted on the back deck. If you have any questions please don't hesitate to ask.

Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount

Key West, Florida, United States

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Bath

Sleeps

$851.89

Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all three bedrooms, the kitchen and the living room. Birds of various types, boating activities, lush oasis gardens are just a few reasons why people keep returning to our paradise property. Click on 'more information' also click on 'More info on Brad & Dee' to learn more about island. brbr1800 Atlantic is located in the middle of the Island on the Atlantic side. Two miles up is the Key West Airport and 2 miles south is the famous Mallory Square where the cruise ships dock. Off of Mallory Square is Duval Street where so many shops, bars, restaurants, and museums are located.brbrKey West is a small island but we still recommend you renting a car, scooters, or even rent bicycles to get around to see it all. There are so many unique and great places to eat at or visit for entertainment. brbrEvery evening down at Mallory Square they have a Sunset Celebration. This is where people with unique talented skills perform. Also down here are many fun vendors who set up shop. Everyone watches and waits to see the sun dip into the ocean. Now for the nightlife to wakeup and begin. brbrMallory Square and Duval Street.is the Center of where it all happens. There are lots of tourist shops available and in the evening many live bands play at the bars. Some people like to do the Duval Crawl where they go from bar to bar. Jimmy Buffet's first Margaritaville is located down here to remind all you Parrotheads that it's 5 O'clock somewhere. There are many historic museums to explore. Never a dull moment. There is so much Happening on this little Island that is only about 4 miles long and 2 miles wide. Grab your favorite drink and enjoy the SUN, SAND, SEA AND FIREBALL SUNSETSbrbrPLEASE NOTE: THERE WILL BE ONGOING CONSTRUCTION WORK AT THIS COMPLEX MAY 2025 UNTIL MARCH 2026 REPAIRING BALCONIES. THERE WILL BE NOISE AND DUST DURING THE WEEKDAYS

Panoramic 3BR/3BA Condo - Direct Beach Ocean Front

Key West, Florida, United States

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Bath

Sleeps

$605.77

Enjoy the New and Completely Renovated bathrooms to this tropical residence. This is quiet, peaceful living on the Atlantic Ocean. The spectacular view can be seen immediately upon entering the condo. The floor to ceiling glass walls provide a full sea panorama from the living room, dining room, kitchen and master bedroom. The 31 foot oceanfront balcony is accessed from both the living area and master bedroom. The master bedroom has a king size bed, walk-in closet, and en suite bath. the guest bedroom has two twin beds, closet and en suite bath.brbrIn addition to the sound of soothing ocean waves, the amenities of this tropical small resort include private screened and lighted tennis court, ocean front gym, two heated pools (large 50 foot main pool and a smaller free form pool), poolside grills and dining areas, covered parking, and privacy of a security gate.brbrThis 1400 sq ft unit is fully equipped. Located on the elevated first floor, close to the elevator and your assigned parking space. The property sleeps 4. Each bedroom and living room is equipped with a flat screen TV and the unit comes with free Wi-Fi.

Peaceful Setting Amongst The Active Island Life Style

Key West, Florida, United States

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Bath

Sleeps

$581.49

This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman Annex. You have the views of the Gulf and ships that pass by the windows as they arrive and leave port. The apartment has two balconies. You can see the sunset over the ocean every evening. The giant size living area features 18ft ceiling at the highest point and large windows on three sides on the room for breathtaking ocean view. There is a full kitchen, dining area and large living room. The guest bedroom is on the first floor with twin beds and full bath. The master bedroom has a queen size bed along with a full bath on the second floor.brbrPlease note: This property is monthly rental -This property has a 28 night minimum stay

Afternoon Delight at The Truman Annex in Key West

Key West, Florida, United States

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Bath

Sleeps

$195.06

Rooftop Renaissance vacation rental falls into a distinctive design category of Heritage Victorian - Meets Modern Luxury. This one-of-a-kind monthly rental is situated on two floors of one side of a grand historic home on Caroline Street. An exquisite 1BR 2BA luxury accommodation, it was redesigned to offer all the accoutrements of an upscale condominium. It provides pleasing views of tin roofs and treetops, and a peaceful Zen-pool Garden below. Located in the Key West Historic Seaport neighborhood, it`s a short two blocks from the famous harbor walk. Within a few minutes` walk enjoy a diversity of dockside restaurants, renowned bars, live music, and gaze at the sail and power boats!brbrThe interior is modern, classical, and island style all at the same time. Festive Caribbean blue walls throughout are contrasted with bright white trim. Ocean themed artwork adds to the tropical Island vibe. A distinctive black metal staircase, with wooden risers, joins the two levels of the condominium. The first level accommodates the living room /kitchen/dining spaces, and one full bathroom. Level two is solely reserved for the master bedroom suite.brbrbrbrGREAT ROOM; First LevelbrbrThe living room area has a stylish cream-colored L-shape sofa. On the wall opposite the sofa, is a handsome floor to ceiling storage cabinet that hides away a queen-size Murphy bed. This creates an additional sleeping space with its own bathroom.brbrSteps from the sofa, a doorless entrance leads to the U-Shape kitchen. Built-out with granite counter tops and white cottage style cabinets, the kitchen provides upscale stainless-steel appliances. It`s equipped to do some serious cooking, but a playful sign on the wall reminds you too, Relax, You`re in Key West! Two kitchen windows invite in the sunlight and provide pleasing views, including the outdoor private back deck.brbrAround the corner from the kitchen, the open-air back deck connects with the living room through French doors. Set for two, an adorable counter-height table with chairs and sun umbrella provides the perfect place for morning coffee and evening cocktails.brbrReturning to the living room, and facing the staircase, take note of the dining area, set with a tasteful white dining table and seafoam tone chairs. Now continue past the dining set, through the square arch, into the downstairs hall. Here you will find the laundry closet on one side of the hall, with full size stackable washer/dryer. On the opposite side there`s a full-size bathroom.brbrThe downstairs bathroom is made elegant with a classic white marble top vanity and jade jewel tone tiled shower. A large sash window provides plenty of natural light. Storage under the vanity top provides a convenient place to stow your cosmetics. Stepping back into the hall, our tour proceeds to the spiral staircase ascending to the master bedroom suite.brbrbrbrMASTER SUITE; Second LevelbrbrAt the top of the house, Rooftop Renaissance provides an exceptional romantic hideaway. Get ready for a WOWZA moment when you step into the bedroom. A masterfully reinvented attic, it`s an extraordinarily cool space. When I first walked into this room, I almost felt as if I could be in a tropical USSStarship Enterprise.brbrBold wing-shaped angular ceilings create a thrilling artistic space. Inset spotlights and twin shuttered skylightswash the blue and white room with light, creating intriguing shadows. The queen size bed commands the center of the room. A dressing bench is placed at the foot of the bed. Tidy nooks and crannies are expertly set with a desk, bureau, shelves, storage, and closets.brbrThe full-size master bathroom is stunning with a double size shower with indigo jewel tone tiles and frameless glass doors. The white marble vanity top is extended out past the sink, to create additional counter and drawer space for personal items. A fanciful feature is the sash window in the shower that frames a picturesque treetop view. Between the window, ceiling, and vanity lights, the space is perfectly lit.brbrbrbrBedding Summary:brbr1 Queen Size bedbrbr1 Queen Size sleeper sofabrbrAmenities: A shared Zen Garden swimming pool and in-ground spa are at the back of the property. Private open-air deck adjoining the living room. Stainless-steel kitchen appliances include oven with glass stove top, French door refrigerator with icemaker, dishwasher, microwave Keurig. Laundry closet with full-size w/d. Wi-Fi. Large TV. Lush tropical gardens and landscaping.brbrbrArea: Heart of Key West`s designated Historic Seaport District. There is so much to do right on the harbor. Walk to all Old Town features, no need for a car. Just two short streets from Duval St. (remember it takes 3 to 4 Key West streets to make a city block); two streets from the harbor where the boats are docked. Close to Mallory Square Sunset Celebration and Old Town Key West retailers.brbrActivities: Close to adventures and activities including sailing, boating, diving, museums, nightlife, music. Conveniently located near gourmet grocery shopping with excellent wine selection, sushi deli, and butcher. Close to shopping, art galleries, and a variety of national and international restaurants, coffee shops. Close to Simonton Beach. Be sure to stop by the Schooner Wharf Bar, the oldest and most authentic bar on the harbor. You may want to dine at the Half Shell Raw Bar, the original seafood restaurant on the harbor. If you want to come by boat, you can possibly arrange to dock here. Close to the beach.brbrParking: There is no off-street parking available at the property. If you bring a car to Key West we suggest that you park it in the City of Key West Old Town Parking Garage just up the street on Caroline Street. From this location you do not need a car. Enjoy walking or biking everywhere--you`ll see more that way.

Rooftop Renaissance - Upscale Condo in Old Town Key West. Perfect for Couples.

Key West, Florida, United States

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Select Dates for Price

*Please note that this home is available for 28+ night stays only.*brbr*This home has been recently upgraded with a remodeled kitchen, renovated upstairs bathrooms, new floors, and fresh furniture in the living room and outdoor area.*brbrLocated on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!brbrYou will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style town home in Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation in a quiet gated community surrounded by historic buildings and tropical flora or wander just a few block over to all the excitement of Duval Street.brbrDecorated to reflect the spirit of Key West, this 2-story condo will help you unwind and feel right at home. On the main level this property features a fully equipped kitchen, dining area, half bath and living room with French doors that open to a sunny private patio. There you'll find an outside dining area ideal for your own personal happy hour. Upstairs are two bedrooms each with their own private bath and balcony, perfect for when a little quiet time is needed. A Place in Paradise also features a washer/dryer and WIFI. A beautiful shared swimming pool is just around the corner, to take a dip and cool down surrounded by plenty of lounge chairs for sunning, relaxing or reading.brbrConveniently located to all the best Key West has to offer, it is only a short walk to Duval Street where you will enjoy the finest restaurants, bars, galleries and great shopping. The Sunset Celebration at Mallory Square, The Tropic Cinema movie theater, and Fort Zachary Taylor State Park and beach are all within easy walking distance. Just park your car under the reserved covered parking when you get here and you won't need it again!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 and is part of 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- This home offers a sleeper sofa as an additional sleeping option.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- 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 / Queen bed brBedroom 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.

A Place In Paradise | Key West Walkable w/ Shared Pool | Month-Long Stays

Key West, Florida, United States

Bed

Bath

6

Sleeps

$242.0

Summary:brbrPet Friendly! 2-Bedroom, 1-1/2 Bathroom Townhome at the Key West Golf ClubbrbrbrbrThe Space:brbr10brbrbrbrStep into our Island Oasis! A very spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the coveted gated community of the Key West Golf Club. With beach-style flooring throughout and charming shiplap accent walls in the living area and main bedroom. This home exudes the island life and Key West charm. The open concept living and dining areas flow seamlessly from the fully equipped kitchen to a large, screened deck. Looking through the glass wall with sliding doors is a peaceful view of the yard and serene butterfly garden. Upstairs, enjoy a private balcony off the front bedroom and another large screened in porch off the rear bedroom. Just around the corner is the expansive heated lagoon-style pool, perfect for a refreshing swim, enjoy your favorite book, or a cocktail. Our Island Oasis is just minutes away from some of the island's best hidden gem restaurants and island activities. Whether you're looking to explore the vibrant nightlife on Duval Street or enjoy the laid-back atmosphere of downtown, you're only a quick 10-minute drive away. Don’t forget your golf clubs or rent theirs. This is a perfect Oasis and ideal for those who want to be close to the action but still enjoy a peaceful retreat. Your island adventure awaits! Pet Friendly

2 Bedroom Townhome in Key West Golf Club

Key West, Florida, United States

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Bath

Sleeps

$175.89

Located in Key West 2 blocks from Duval and half a mile to Beach, enjoy what this 1-bedroom condo has to offer. This lovely property features a cozy bedroom with a queen bed and a comfortable living room with a sofa bed. Guests can relax in the peaceful atmosphere and take advantage of amenities like AC, WiFi, and a washing machine and dryer. You will have your own parking space and access to the common pool.

1-bedroom 2 blocks to Duval, close to beach, parking, and pool

Key West, Florida, United States

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Bath

3

Sleeps

$391.46

Large art-filled, two story Key West condo boasts 3 inviting bedrooms, including a king bed, queen bed, and an office or third bedroom for extra flexibility. Guests enjoy 2 full bathrooms, one with a large shower and one with bathtub. Furnished as a home not a vacation rental and filled with fine art, guests can settle in for longer stays and live like locals. Located within the prime Old Town Key West quadrant, a short stroll to and from the Duval downtown, Truman Ave., the Marina, White Street Arts walk, and more, and surrounded by flora and shade, there's no quieter place to unwind and rest, eat in or make home base for enjoying all Key West has to offer. Enjoy one of the largest pools on the island, heated and salt water, 2 TVs, stereo, coffee maker, blender, W/D, DW, etc. etc.. Feel free to reach out to us during your stay – we’re happy to suggest local spots to check out.

Art-Filled 1,700SF 3BR/2BA Old Town Key West Home with 2 Decks, Pool, Parking,++

Key West, Florida, United States

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Bath

Sleeps

$534.38

June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has its own marina, fishing charters on site, tiki bar that serves food and drinks while you watch the yachts cruise by, pool with hot tub, beach with swim platform, 6th floor observation deck, sun decks, sauna, gym, covered parking and linen change once per week-more often if desired. Best location to stay in key West! Right on Front St, walk to Duval St and Mallory Square.

The Galleon Resort Best Resort Location in Key West

Key West, Florida, United States

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Bath

Sleeps

$343.11

Book your well-deserved getaway to this dog-friendly Key West home. With a prime central location near Duval Street and access to a shared pool, this home will let up to four guests and your happy puppy (for a small nightly fee) unwind in style. brbrNotice: This is in a residential area, Quiet Hours are 10:00pm- 8:00ambrbrRight in the heart of the action, this home surrounds you with mouthwatering dining options, historical sites like the Ernest Hemingway Home and Museum, and of course, the Key West beaches. brbrBury your toes in the warm Florida sand while you catch up with a good book on by the waves. Book your spot on a deep-sea fishing adventure, or maybe explore the coast on a stand-up paddleboard. Toss a load in the shared washer/dryer then take your tropical cocktail out to the shared pool to catch some rays. Connect to the free WiFi and stream some gentle background music before whipping up a dish in the fully equipped kitchen. brbrWhether you're wandering through the charming shops, sampling the local fare, or slipping into vacation mode on the iconic beaches, this dog-friendly Florida Keys home makes it easy to enjoy it all.brbr**This is a pet friendly unit with a two dog limit and a 35 pound weight limit for each dog.**

Contemporary Dog-Friendly Cottage with Easy Beach Access & Shared Pool

Key West, Florida, United States

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Bath

Sleeps

$404.36

Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just three miles from vibrant Duval Street, and four miles from historic and majestic Mallory Square.brbrThe property features two pools, a hot tub, park-style grills, picnic tables, onsite bar, and much more.brThis spacious two bedroom condo features a king primary suite with hardwood flooring, a connecting ensuite full bathroom with shower and bath tub. The guest bedroom features a queen bed with wood flooring. The condo also features a full kitchen, with a full refrigerator, microwave, stove, oven, dishwasher, coffee maker (drip style), toaster, blender, dishes and utensils. The living room features a queen-size sleeper sofa, HD TV, a dining area and access to a private patio. This is a two-story condo and the bedrooms are upstairs.brbr*Must climb stairs — Stairs required to access the unit, Stairs may be required to access bedroomsbrbrGuest must be 25 yrs old to rent and check-in to this unit.brbrUnits are assigned in seven night increments, multiple week stays may be booked, room moves may be required.brOccupancy limits are strictly enforced.brbrNo RVs, campers or mobile homes may be parked on the premises. Parking is limited to two (2) vehicles per unit.brbrWelcome Center hours of operation are: Sunday to Thursday 9am – 5pm and Friday/Saturday 8am – 10pm. Late arrivals must call the welcome center for arrangements.brbrAn ID and a credit card is required upon arrival for a refundable security deposit.brbrWe 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.brbrGumbos is not currently operating as a bar or restaurant.brbrLaundry facilities located on top floor of buildings for a fee. Towel Exchange is not available.brbrPictures are representative of units on property. All feature similar layouts, decor and amenities. Property features most 2 story units. There exists a chance you may be assigned a single story unit. Specific unit is assigned at check-in by the front desk.

Waterfront Property - Marina Access - Spacious - Excellent Key West Condo

Key West, Florida, United States

Bed

Bath

6

Sleeps

$204.8

A TRUE CARIBBEAN PARADISE! Location! Location! Location! brStarting Jan 2026 , this beautiful cottage will become monthly! Stays will have to be 28- 30 days. Discount of 10% for monthly stays. Make plans to stay longer, relax or work remotely from paradise for a full month in 2026. brThe Conch Retreat Condo is located in the prestigious Truman Annex. This condo has 2 bedrooms, 1 bath, queen and 2 twins (or we can convert the twins to a king bed upon request). both TV's with cable.brFree parking spot comes with condo, however you don't need a car. Free High Speed Internet. There are 2 bicycles for your use with helmets. brFully equipped kitchen. Has everything you need for your stay. brThis upper floor condo has doors that open up to back deck where you can relax around the tropical trees. Great for your morning coffee and reading. Bathroom with walk in shower, medicine cabinet and storage cabinet. Vanity and shelves for storage. brWasher & dryer with iron & ironing board. brLiving/Dining area has table with seating for four. brFront balcony opens up from kitchen with seating. brAll towels & Linens including beach towels.brLarge heated Pool for Shipyard guests only. brYou are in a gated community off of street in a quiet community.brExplore the Waterfront/water park behind the complex. Amphitheater, splash park, playground. Stroll to the Waterfront Pier and enjoy the sunsets and sailboats. Mallory Square is famous for local vendors and amazing sunset celebrations. brRoad to Fort Zachary Beach is directly behind complex. You have opportunities for swimming, picnic, grilling, snorkeling, and fishing. Visitors can also enjoy a short nature trail and bicycling within the park. The beachfront Cayo Hueso Café offers snacks, cold beverages, beach sundries, and souvenirs. Two blocks to Duval where you will find shopping, restaurants, night clubs and museums. Visit the Historic Seaport District where you will find dining, entertainment or catch a sunset cruise. There is so much to see and do. My husband and I take pride in our vacation homes. It's our home away from home and want our guests to be comfortable and enjoy what Key West has to offer. brWe're offering discounts for monthly stays.brTo see our other VRBO Key West listings:brTruman Annex Shipyard (1 bed, 1 bath) Island Escape vrbo.com/934388habrTruman Annex Shipyard (3 bed, 2 bath) Sea Breeze Cottage vrbo.com/987489ha

CONCH RETREAT Truman Annex Condo - 2 decks, pool, 2 Bikes, Free parking and WIFI

Key West, Florida, United States

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Bath

Sleeps

$244.93

TRUMAN ANNEX: brbrPLEASE NOTE: As Of January 2026, This property is switching to monthly rentals. Please inquire with host first. brbrThe Rooster Retreat is a lovely two bedroom, one bathroom ground floor end unit with a spacious backyard deck. brThe master bedroom offers one king size bed, ceiling fan, 55 TV and double french doors that open onto the back deck. brThe queen bedroom offers natural light through the front window, ceiling fan and 55 TV.brThe bathroom, located in the common area between the two bedrooms, offers a recently updated vanity and walk-in shower.brbrThis unit is cleaned regularly by our local cleaning service and we are following CDC guidelines for cleaning/disinfectants. Read our reviews, we have always been known to have a spotless, clean place - and we've increased our care. Stay with us!brbrBeing at the far end corner of the property, unit #175 boasts added privacy compared to neighboring units. Unique to this floor plan is the added natural light from the extra exterior wall and window. Enjoy the open kitchen to living room layout, large leather sectional and newly added 65 Sony TV. You will be just a short walk from Truman Water Front park and Coffee Butler Amphitheater. Pack a picnic and take a short bike ride to nearby Fort Zachary Beach.brbrThis sunny ground floor condo is clean with well-appointed bedrooms, beautiful linens and art work. Enjoy the breeze on a cool night with open double french doors in the master bedroom. The newly remodeled kitchen with quartz countertops, thoughtfully placed lighting and seating for four is both stylish and functional. A washer/dryer are located within the unit for your convenience. The kitchen is fully equipped with pots & pans, dish towels and dish ware. Enjoy central air conditioning, on-site laundry and all the necessities for both long and short-term stays. brbrRelax at the Truman Annex Shipyard Pool - located within the property grounds.brOur condo is outfitted with beach towels, beach chairs, coolers, etc. We also have designated on-site parking, although it's likely you will not need (or want) to get in your car while you're here. brbr(Due to fire code ordinance, this condo is unable to have an outdoor grill, much like many other condos on the island.)brbrThank you.brbr2019 New deck and landscapingbrbr2018 and 2017 CONDO UPDATES: New bathroom, All new AC & air handler,

Two Bed One Bath Ground Floor End Unit in the Heart of Old Town

Key West, Florida, United States

Bed

Bath

Sleeps

$361.07

Welcome to Palm Isle! brbr brbrA tropical 2nd-floor condo in the charming Meadows area of Key West. Relax on your private front porch, perfect for watching the world go by, or retreat to your private back porch overlooking the common area with a shared pool and BBQ grill. Just six blocks from Duval Street and the Historic Seaport, and only a mile from Higgs Beach, this location offers easy access to all the best that Key West has to offer. Palm Isle is the perfect home base for your island getaway. brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom: King Bed, TV brbr brbrLiving Room: Sofa w/ Pull Out Queen Bed, Chair, Smart TV brbr brbrKitchen: Nicely equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Heated (Nov-Apr) Pool brbr brbr- Shared Propane BBQ Grill brbr brbr- Private Deck brbr brbr- Outdoor Table and Seating brbr brbr- Drip Coffee Maker, Toaster, Blender brbr brbr- Street Parking (no off-street parking available) brbr brbr- Bike Rack brbr brbr- Linens and towels provided brbr brbr- 0.7 miles to Duval Street brbr brbr- 0.9 miles to Key West Historic Seaport brbr brbr- 1.1 miles to Southernmost Point brbr brbr- 1.4 miles to Mallory Square brbr brbr- 1.4 miles to Fort Zachary Taylor State Park Beach brbr brbr- 1.9 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. 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.

Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches

Key West, Florida, United States

Bed

Bath

Sleeps

$690.29

Key West Paradise Found is perched on the top floor with breathtaking Ocean Views, Reconfigured Master Bedroom and Remodeled Kitchen. If you have a larger party we also own the 2 units right next door so they can all be rented together. Enjoy your luxury condo with breathtaking view of the deep blue Ocean and sparkling salt water pool within our tropical garden.....There is nothing like it...anywhere.... at any price. Paradise Found is a TOP FLOOR spacious, clean and comfortable Key West condo experience. Enjoy your PRIVATE BALCONY for lounging sunbathing and dining.. This is a two bedroom two bath spacious condo. Newly renovated for 2020 and enhanced with Comfortable Beds. The Master has a KING. The second bedroom offers a QUEEN with an additional TWIN for sleeping flexibility. There is also a Queen sleeper sofa in the living room. brThis is Key West's most coveted location. Nestles between two of Key West's best beaches, Smathers Beach is just a 20 yard walk on the side walk. We are within 2 miles of most locations on the island. Enjoy the nightlife and excitement of Duval Street (restaurants, bars, live entertainment). Scuba Diving, Jet Skiing, Kayak Rentals, Deep-Sea Fishing, Cruises. Close to 18-Hole Golf Course, Moped/ Bicycle Rentals, Airplane/Seaplane Tours. We hope that you will enjoy staying on the ocean with all the comfort of home . After your first visit we hope you will agree.... Paradise has been found!brOur other VRBO Listings #4091146 & #4091149brbrCONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through the Spring of 2026. The building our units are in has been complete and we have new balconies. The work will be in the West building until Spring of 2026.

Panoramic Ocean: Beach from every window

Key West, Florida, United States

Bed

Bath

Sleeps

$212.63

This lovely Island Escape Condo is a upper level condo located in the prestigious Truman Annex. Not just another rental property! Location is everything.!!! Close to Duval.brStarting Jan 2026 , this beautiful condo will become monthly! Stays will have to be 28- 30 days. 10% discount for monthly rentals. Make plans to stay longer, relax or work remotely from paradise for a full month in 2026. br-Large private corner balconybr- Free High Speed Internetbr- Secure Parkingbr- Fully equipped kitchen with microwavebr- Washer and Dryerbr- Towels, Linens, Beach Chairsbr- Large community swimming pool for Shipyard residentsbr- Water park across the streetbr- Entertainment and cuisine in easy walking distancebr- Close to Fort Zachary park and Beach (Key West's most beautiful Beach)br- Just a few blocks to Mallory SquarebrbrbrOur favorite room is the spacious covered deck that opens up from living room with ceiling fans, tropical foliage, dining/sitting for 4.brThe Island Escape is a corner condo which allows for more privacy. The condo's parking stall is right at your front door and bike racks beside condo. Shipyard community pool is close and heated. Windows across the front of the condo let in lots of light and tropical breezes. No need for a car you can walk 2 blocks to Duval Street where you will find restaurants, shopping, night clubs and museums. Fort Zachary Beach is also close. You can rent kayak, canoe, or paddle board and launch on the beach. You can also picnic or grill in the park. Mallory Square where sunset is celebrated every night has local vendors and entertainment. Breakfast at Blue Heaven, visit Hemingway's House then have a drink and enjoy music at the infamous Green Parrot Bar. Visit the Historic Seaport District where you can watch boats, find great dining or catch a sunset cruise.brCheck out the Waterfront/Splash Park just behind the complex. Playground for kids, walk the pier at night to watch sunsets, entrance to Fort Zachary Beach and much more. You are close to everything!!! brThis condo is also our vacation home. We take pride in our condos and want our guests to relax and feel as if they are in their home away from home. br To see our other VRBO Key West listings:brTruman Annex Shipyard (2 bed, 1 bath) Conch Retreatvrbo.com/261681habrTruman Annex Shipyard (3 bed, 2 bath) Sea Breeze Cottage vrbo.com/987489ha

Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

Key West, Florida, United States

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Bath