Vacation Condo Rentals By Owner In Key West, FL

Prime Old Town location meets effortless island living in this 2‑bedroom, 1‑bath first‑floor Shipyard condo. Bright interiors, a private tropical patio, and a coveted ground‑floor layout make this home ideal for full‑time living or vacation use. Gated community, resort‑style pool, assigned parking, and just minutes to Duval Street and the beach. A rare opportunity in one of Key West’s most sought‑after neighborhoods.brbrPlease note: This property has a 28 night minimum stay

Another Day in Paradise at the Truman Annex in Key West

Key West, Florida, United States

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Bath

Sleeps

$512.72

Duval Square Retreat is In the heart of Old Town. Duval Square is located at the artistic and quieter end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The first floor offers a well- equipped kitchen, and an open living and dining concept, French doors to a private balcony and a half bath powder room. brbrUpstairs, the main bedroom suite has a private balcony and ensuite bath. The second second bedroom also has an ensuite bath. brbrThere is central air conditioning and Wi-Fi internet. The complex's shared pool and sunning area overlooks world famous Duval Street. On the street level you will find a unique tree lined courtyard with restaurants and shops. While gated garage parking is provided here, all you really need is a bicycle for your main mode of transportation as you can walk or bike everywhere from Duval Square. brbrBedding: 2 QueenbrA shared, sun-drenched, rooftop pool and pavilion are just steps from your door.brbrThis is an unbeatable location offering easy pedestrian access to dozens of shops and restaurants, the Ernest Hemingway Home Museum and other notable local attractions, and of course the serene, turquoise ocean that the island is famous for. brbrGather your friends and family together and book a Key West vacation you will never forget at Duval Square Penthouse.brbrBeds: 3 Kings, 2 Twins, 1 Sleeper SofabrDuval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool and pavilion upstairs. Although the condo includes one assigned parking space in the gated garage, you can stroll anywhere from this conveniently located condo. All of the shops, galleries, restaurants, and attractions on and around Duval Street and nearby beaches are just a leisurely stroll away. brbrWhen you enter the home you will find a fully equipped kitchen, dining area, spacious living room and a convenient half bath. French doors let in the natural sunshine and open to the private back deck with dining table and chairs perfect for outdoor entertaining. brbrOn the second floor, you will find 2 bedroom suites, each with their own private bathroom and an additional private balcony off the main suite.brbrBedding: 1 king, 1 queen, 1 queen sleeper sofa.brbrElevator access from ground level to the first floor of the condos. Stairs to the unit's second floor bedrooms.brbr1 Reserved Parking Space in the Gated Garage.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

Duval Square Retreat: A beautiful condo steps from the action

Key West, Florida, United States

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Bath

Sleeps

$766.94

In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined courtyard that includes shops and restaurants. This three bedroom two bath unit is in one of two standalone WALK-UP buildings in the Duval Square complex. You enter a large open living, dining, kitchen area with French doors & porch overlooking the courtyard below. The master bedroom with ensuite bath has a king bed and access to a second deck area overlooking the courtyard. There is a shared pool and sunning area that overlooks the world famous Duval Street. Central air conditioning/heat & 1 covered parking space. PLEASE NOTE THIS PROPERTY IS ACCESSED BY STAIRS ONLY. brbrBedding: 1 king, 1 queen, 2 twins, single rollaway & sleeper chair. brSleeps 6 & up to 8 with extra person charge.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

Duval Square Courtyard Condo is just steps from the action

Key West, Florida, United States

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Bath

Sleeps

$384.07

Poolside Breeze is a nicely decorated two bedroom 1st floor condominium with an excellent location very close to the pool. Poolside Breeze has an extra large floor plan with an extensive private balcony. brGorgeous new Kitchen renovated in 2018. Both bedrooms and the living room feature sliding glass doors that open on to the private balcony overlooking the lush tropical courtyard of 1800 Atlantic. There is a full size fully equipped eat in Kitchen and a dining room area that seats 6. Full size washer & dryer in the unit. The Master bedroom has a king size bed. The guest bedroom has a queen and for your convenience there is a queen size sleeper sofa in the Living room. The unit has wireless internet. There are Mexican tiled floors in the living room and hallways with carpet in the bedrooms. Enjoy the tranquility that this property has to offer.brbrMinimum length of stay requirement may be in place depending on high/low seasons. For stays shorter than 3 nights please contact the office or email your inquiry.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Poolside Breeze Retreat, Tropical flare, Key West spectacular getaway.

Key West, Florida, United States

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Bath

Sleeps

$363.2

Escape to paradise in this spacious first-floor garden-view condo in beautiful Key West — the perfect setting for a relaxing island vacation.br“Nautical Adventures” comfortably accommodates families and groups with:brbrbrA king bed in the primary suitebrOne double bed and one twin bed in the guest bedroombrA queen sleeper sofa in the living roombrbrbrEnjoy seamless indoor-outdoor living with private balcony access from both bedrooms and the living room. Start your mornings with coffee overlooking lush tropical gardens and unwind in the peaceful island atmosphere.brThe condo features:brbrbrHigh-speed Wi-FibrFully equipped eat-in kitchenbrDining table seating for 6brSpacious living area perfect for gatheringbrFull-size washer and dryerbrOne assigned parking spacebrbrbrGuests are just a short stroll from the resort-style pool and Jacuzzi. Sports enthusiasts will love the three lighted tennis courts, including the island’s only clay court.brConveniently located just 1.5 miles from the Historic District, you’ll be close to the best dining, shopping, nightlife, and attractions Duval Street and Mallory Square have to offer while still enjoying a peaceful tropical retreat.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Our Nautical Home Key West prime location & amenities. Last minute specials.

Key West, Florida, United States

Bed

Bath

Sleeps

$470.54

Enjoy the resort-style amenities of 1800 Atlantic Condominiums. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees. Plan a picnic or barbeque in the shade of this beautiful garden. brbrThe property features a 70 ft pool fronting the Atlantic Ocean. A 12-person jacuzzi awaits. A courtyard changing room sauna is yours to enjoy. There is a Fitness Room, large picnic and barbecue area surrounded by the tropical gardens.brbrOne clay and two hard court lighted tennis courts are yours to enjoy at no additional cost. The largest beach in Key West, Smather's Beach, is adjacent to this condominium complex, offering white sand, palm trees, lounge chair and umbrella rentals, volleyball nets, sailboat rentals, and parasailing. An extensive leisure trail for walking, jogging, and bike riding fronts this beach.brbrOld Town, Key West's hub of shopping, dining, live entertainment, art galleries, and sightseeing, is just one-and-one-half miles away. Here you will enjoy all that ''downtown Key West'' has to offer, but will greatly appreciate coming back to your peaceful surroundings at the end of the day (or night!) to recharge. Parking for one vehicle in reserved space in the gated garage is also included. There is elevator access.brbrWhile at Vista Fresco, enjoy relaxing on your balcony while gazing through the vegetation toward the ocean beyond in these nicely appointed condominiums. brThe large living area, dining area and eat-in kitchen add to your comfort in your home away from home. The main suite of the two bedroom units features a large walk-in shower. Central a/c, cable TV, VCR and full-size washer/dryer round out the amenities of all the units. brBedding: 1 king, 2 twins, 1 sleeper sofa.brHandicap equipped bathroom with limited access to balcony.br**Disclaimer**br*The peak sargassum season in Key West is typically from July thru September and possibly June. You may see significant amounts which can impact your stay. While the naturally occurring seaweed itself is not dangerous, it can accumulate on beaches, producing a foul odor and potentially harboring organisms that cause skin irritation. We do not provide discounts for the situation.

~VISTA FRESCO~ Oceanside condominiums with resort-style amenities

Key West, Florida, United States

Bed

Bath

Sleeps

$431.57

La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly across from Smathers Beach. A residential complex, La Brisa offers a neighborly and relaxing atmosphere. Join in on community held activities at the club house, partake in a match on the tennis courts and enjoy the sizable kidney shaped pool, hot tub and a spacious common area for chatting, eating and relaxing in the sun.brbrUpon entering Ocean Vista, you are instantly struck by the magnificent view of the Atlantic Ocean and drawn out to your private balcony where you can relax and relish in your beachfront vacation. This appealing, two bedroom, two bathroom condo has been lovingly decorated. A large wall mirror is positioned to enhance the floral colors and rattan furniture and the open design of the living/dining area adds to the relaxing and airy atmosphere. The spacious kitchen is fully equipped, has ample cupboard space, double sink and a pretty dinette for two. After cooking delectable meals in your kitchen, enjoy good food and great conversation at your glass topped rattan dining table for four.brbrAdorned in charming floral prints and light wood, the Primary Bedroom, with a King Bed, offers peace and tranquility. There is an individual door to the private balcony, perfect to catch an early morning Sunrise, and the double windows facing out to ocean offer a breathtaking view. The Primary Bathroom has an individual vanity area with stocked linen closet. The second bedroom, delightful in its beachy motif, features two twin beds and a nice sized closet.brbrThis unit has WIFIbrbrLa Brisa captures a feel for island life, the way the locals live it, away from the clamor of downtown. Quiet moonlit walks on the beach, a morning café con leche from a local vendor and a beach sunrise make for an unforgettable vacation. And while you are away from the hubbub, you are not far away. There is a bike trail that leads you along the Atlantic Ocean, past many Key West sights, into the downtown area. The White Street shops are just a pleasant bike ride away, as are a myriad of fabulous Key West restaurants. While savoring the distinctive essence of La Brisa, take in the ocean, the Key West weather and when you see the bright red WWII Bi-Plane fly overhead on one of its daily excursions from our small airport, ask yourself, Why Not brbrThere is elevator access from the ground floor to the condos above. There is one reserved, covered parking space.brbr**ELEVATOR SHUT DOWN NOTICE: The East building elevator will be shut down starting April 27th, 2026 until April 25th, 2026 for a Elevator Modernization Project. The condo will ONLY be accessible via stairway.brbr**POOL CLOSURE** The pool and jacuzzi will be closed from July 6th to August 30th.brbrPlease note; the LaBrisa Condo Association requires additional registration in advance of your arrival. Details will be provided along with your RKWV rental agreement.brbr**Disclaimer**brbr*The peak sargassum season in Key West is typically from July thru September, with June may also see significant amounts which can impact your stay. While the naturally occurring seaweed itself is not dangerous, it can accumulate on beaches, producing a foul odor and potentially harboring organisms that cause skin irritation. We do not provide discounts for the situation.

Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)

Key West, Florida, United States

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Bath

Sleeps

$381.14

Thank you for considering Isle Be Back for your escape to the tropical paradise of Key West. Here you will enjoy the lap of luxury with this two-bed & two-bath upstairs unit located in the highly desirable Shipyard section of the Truman Annex. Paradise awaits you just two blocks from the sights and sounds of Duval Street. A short walk or bike ride to Ft. Zachary State beach for sunbathing and snorkeling, Mallory Square to catch a spectacular sunset and the Ernest Hemingway House where the six-toed cats call home. Fine dining is an easy walk in any direction from this perfectly located condo where you get to live the laid-back tropical lifestyle of Key West. brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Isle Be Back at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$816.8

Concierge Realty is proud to present luxury villas at Hyatt Beach House!brbr**Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only.brbr**All bookings are time sensitive and availability can change at any time. Send us a message to confirm exact availability prior to making a booking request. brbrGreat destinations in Key West should offer more than a good night's sleep, and Hyatt Beach House takes pride in offering you the best of everything -- a great location, luxurious rooms and super service. brbrHyatt Beach House Resort is surrounded by private marinas for easy access to boating and fishing. It’s also just a short distance from Old Town, the heart and soul of Key West. Key West is Florida’s capital of laid-back leisure. Enjoy the phenomenal dining, live music and bar scene.brbrMaster suite with king-size bed, adjoining bath, walk-in shower and spa tubbrGuest suite with king-size bed and full bathbrFully equipped kitchenbrDining areabrSofa bedbrPremium electronicsbrInternet brScreened-in balconybrbrThe resort has a breathtaking gulf coast setting. Paired with the gracious service, top-tier amenities and meticulous attention to detail, you are in for a wonderful vacation.brbrEnjoy the privacy of your own white sandy beach, furnished with thick-cushioned chairs, picnic tables and barbeque grills. Soak up the sun or relax under a lush tropical palm tree. The beautiful plantation-style design creates an environment of relaxation, enjoy the outdoor lagoon pool and spa tub and complimentary Wi-Fi throughout.brbrResort amenities include:brComplimentary parkingbrconcierge servicesbrin-room washer and dryerbrchild care; cribs and high chairs upon requestbrbr**$41.00 housekeeping fee mandatory for all reservationsbrbrThe Vrbo calendar helps provide availability and estimated price quote. Always inquire with the agent and do not reserve airfare until your confirmation has been received.brbrAny issues with resort service, accommodations, physical plant, amenities, etc. are the direct responsibility of the developer and must be handled through the resort, not Concierge Realty. Photos are thought to be truly representative of the resort and accommodations. Any variation from the photo and actual property are unintentional, so guests are encouraged to do their own due diligence prior to reserving. Any variance or disruption including but not limited to renovation, unavailable amenity, change in decor, etc. during the stay, whether announced prior to reservation, occurring during the stay or announced after confirmation, is a matter strictly between the guest and resort, are not deceptive advertising, breach of contract or the responsibility of Concierge Realty.brbrNote that the images are representative of this villa and that a specific view type is not implied nor promised by virtue of the images. A specific view category must be addressed with rental agent. Concierge Realty reserved the right to reserve any view category unless one has been agreed upon in writing. The resort confirmation will show the view designation and the villa will be placed within that view category unless, in a rare instance the view will be noted as not guaranteed in which case the resort reserves the right to place the guest anywhere within the property. Issues regarding view within the guaranteed view category are to be addressed with the resort management as Concierge Realty is not responsible for villa placement.brbrPlease be advised that if a non-domestic credit card is used to reserve a vacation rental, additional fees may be incurred.brbrAll details are accurate to the best of our knowledge. Any questions with regard to view, amenities, bedding configuration, decor or other details should be addressed with Concierge Realty, Winter Garden, FL.brbrGuests are encouraged to do their own due diligence to assure that the resort and villa will meet their expectations.

Hyatt Beach House- 2 Bedroom Located On The Gulf With Private White Sand Beach!

Key West, Florida, United States

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Bath

Sleeps

Select Dates for Price

Key West Paradise Found hes been renovated for 2020 and beyond. New Master Bathroom, 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 is nothing like .... 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....brPARADISE FOUND WELCOMES YOUR VISIT TO PARADISE.brbrbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Key West Paradise Found - Amazing ocean views from every window

Key West, Florida, United States

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Bath

Sleeps

$158.76

Find the best of Key West at your doorstep with this beautiful first floor one-bedroom condo, with a private patio, a shared swimming pool, and a wonderful location close to restaurants, beaches, and more!brbrPerfectly located between Truman Annex and Bahama Village, this comfortable condo sits only two blocks from the fantastic restaurants, nightlife, and shopping on Duval Street. Park your car in the off-street space, walk a quarter-mile to the Ernest Hemingway Home and Museum, and take afternoon bike rides to the soft sand at Fort Zachary Taylor Historic State Park three-quarters of a mile west.brbrThe living space has been meticulously decorated, offering central A/C, free WiFi, and French doors that open to the deck. When you're not dining at Blue Heaven nearby, you can sip cocktails outside among the palms and orchids, flip through the offerings on the HDTV, and splash around in the shared swimming pool. A full kitchen with granite countertops, a private off-street parking spot, and a private washer/dryer are also on hand.brbrPlease note: This property has a 28 night minimum stay

Another Siesta at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$521.99

Serenity by the Sea | 2BR/2BA Key West Condo at La BrisabrbrWelcome to your tropical retreat in paradise! This beautifully appointed 2-bedroom, 2-bathroom condo is located in the gated La Brisa Condominium complex—perfectly situated directly across the street from the iconic Smathers Beach in Key West. With palm trees swaying and turquoise waters just steps away, this is the island getaway you’ve been dreaming of.brbrStep inside to an open-concept space filled with natural light and coastal charm. The spacious living area features comfortable, beach-chic furnishings and sliding glass doors that lead to a private balcony overlooking peaceful salt ponds—where you can enjoy a morning coffee, spot native birds, or simply unwind in the ocean breeze.brbrThe fully equipped kitchen boasts stainless steel appliances, an induction stove, and a breakfast bar with seating for three. Just off the kitchen is a dining area with seating for four—ideal for a family meal or sunset dinner.brbrThe primary bedroom is a relaxing haven with a king-size bed, en suite bath, and direct balcony access. The second bedroom offers two twin beds that can be easily converted to a king, giving you flexibility whether you're traveling with friends or family. A washer and dryer are available in the unit for added convenience.brbrResort-Style Amenities at La Brisa Include:br*Large heated/chilled outdoor pool open 24 hoursbr*Hot tub and sauna-equipped poolside bathroomsbr*Lighted tennis court with pickleball linesbr*Outdoor grilling areabr*Electric charging station for vehicles, golf carts, and e-bikesbr*Designated washing and vacuuming station for your carbr*Covered reserved parking spot + guest parkingbr*Gated access for security and peace of mindbrbrAcross the Street: Smathers Beachbr*Just steps from your door, enjoy one of Key West’s most beautiful beaches with soft white sand, shallow turquoise waters, and plenty of space to relax, swim, paddleboard, or simply soak up the sun.brbrClose to the Actionbr*While the condo offers peace and serenity, you’re just a short bike ride or quick drive from the world-famous Duval Street—home to vibrant nightlife, delicious dining, local shops, and must-see attractions. It’s the perfect blend of quiet relaxation and island excitement.brbrWhether you're looking for adventure or relaxation, this condo has it all—from first-class amenities to an unbeatable location. Book your stay today and experience the laid-back island lifestyle that only Key West can offer!

Serenity by the Sea, 2BR/2BA Condo w/Pool at La Brisa across from Smathers Beach

Key West, Florida, United States

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Bath

Sleeps

$581.33

Enjoy endless views just feet away from the tranquil waters of the Atlantic Ocean. “Beach Club #304” is a serene waterfront oasis located in an upscale gated community within walking or biking distance to the local’s finest spots, including restaurants, beaches, shopping, bars and the infamous Duval Street. This condo community prides itself for being one of the very few on the island that sits directly on the water.brbrThe Living room is brightly decorated exuding light from floor to ceiling. The breathtaking view can be seen as soon as you enter this spacious 2-bedroom coastal retreat, with comfortable seating for those spontaneous movie nights. The kitchen is fully equipped to make that perfect home cooked meal. Relax on the outdoor sofa or dine oceanside on your large, private balcony while soaking in the panoramic ocean views. The balcony is the perfect place to enjoy an evening cocktail or freshly brewed morning cup of coffee.brbrBedroomsbrMain Bedroom: King bed, flat screen TV, direct access to the balcony, oversized spa-like shower.brbrGuest room(Second room): 2 Twin beds OR One King Bed, flat screen TV, oversized spa-like showerbrbrUnit Features:brCentral A/C, Wi-Fi, washer/dryer, security entry, one reserved parking space in the garage and elevator accessbrbrCommunity Amenities: Resort amenities include two ocean side pools (heated), tennis court, outside cooking facilities, fitness center and sauna. Although there is no water access, Smathers Beach and Higgs Beach are conveniently located on either side of the complex. There are plenty of chaise lounges around the pool area as well as a cabana to enjoy during those sunny island afternoons.brbrAdditional things to know:brThe Key West Beach Club Condo Association requires additional registration, which includes providing copies of photo IDs for everyone over the age of 17, in advance of your arrival. Details will be provided along with your RKWV rental agreement.brbr*Disclaimer: Due to the property's oceanfront location, please be aware that Key West experiences seasonal occurrences of fermenting turtle grass along the south shore of the island brought on by our southern winds in the summer. This is a natural phenomenon that is outside of our control.brbrInterim housekeeping provided upon request brThis property will accommodate up to 4 adults brSorry, pets are not allowed.

OCEANFRONT ECSTASY - KW Beach Club #304

Key West, Florida, United States

Bed

Bath

Sleeps

$495.31

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThis freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the ocean and sand in your toes. You'll be able to enjoy quiet afternoons at CONCH IN THE TREETOPS with those balmy Key West breezes wafting through the floor-to-ceiling glass doors, while sitting on your private balcony surrounded by the palm tree tops. CONCH IN THE TREETOPS is located in an upscale private community within walking or biking distance to all of your favorite Key West spots including beaches, restaurants, shopping, and the beautiful waters surrounding the island.brbrTHE LIVING AREA...brbrThe living room of CONCH IN THE TREETOPS is comfortably furnished, with plenty of light streaming in from the floor-to-ceiling glass doors and reflecting off the floor to ceiling mirrors. There's a very large flat screen TV, and plenty of seating for your whole group to gather before heading out to enjoy Key West. The living room sofa pulls out into a queen sized sleeper for extra guests in a pinch. The brand new kitchen with its new stainless steel appliances has everything a good chef would need to prepare any meal. The dining table will seat six comfortably. You can also take your meal out onto the balcony on your dining set in the treetops.brbrTHE POOL, THE BEACH & TENNIS...brbr1800 Atlantic offers Resort-style amenities, including an extra large Community Pool right downstairs. There are chaise lounges surrounding the pool for your comfort, and a cabana with restrooms for your convenience. Please note this is a shared pool with set rules, such as no music and no coolers. We ask that our guests be mindful of their neighbors and respect the rules.brbrFrom the pool, there's a walking path that leads to the on-site beach. The on-site beach offers a relaxing setting, with chaise lounges and soft sand. There is no direct water access from this beach, but Smathers Beach, Key West's largest public beach, is located within walking distance right next door. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. You'll also have access to the newly built fitness center and Key West's only clay tennis courts, both located on-site.brbrTHE ACCOMMODATIONS...brbr** Master bedroom: a King bed, a large flat screen TV, direct access to the balcony, and an en suite with an oversized shower and tub combination.brbr** Second bedroom: Two Twin beds OR One King bed, a flat screen TV, direct access to the balcony, and access to full second bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Community Jacuzzi Accessbr** Assigned off-street carport for 1 car (Parking Garage has a low clearance of 6'2)br** Key West's only clay tennis courtsbr** Handball courtsbr** Fitness Centerbr** Dry Saunasbr** Picnic areas with BBQsbr** Recreation rooms available for private partiesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** This complex has both visitors and locals living here, we expect our guests to be mindful & respectful of the posted rulesbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES

Key West, Florida, United States

Bed

Bath

6

Sleeps

$458.24

**About...** brHemingway Atlantic Retreat is a two-bedroom condo conveniently located near beaches and restaurants, just minutes away from Duval Street. Nestled in a gated oceanfront community, it offers a peaceful retreat with beautiful sunrise and ocean views from Smathers Beach on the private balcony. brbr**Furnishings...** brUnwind on the cozy couches while enjoying a movie, or gather around the dining table that seats six for a home-cooked dinner. brbr**Sleeping Arrangements...** brThe primary bedroom features a king-size bed, while the guest bedroom contains two twin-size beds that can be converted into a king upon request. Both bedrooms offer ample closet space and stunning sunrise and ocean views. Additionally, the living room includes a queen sleeper sofa, making it perfect for accommodating families, friends, or couples.brbr **Details and Amenities...** brHemingway Atlantic Retreat has been recently renovated and features two bedrooms and two full bathrooms. One bathroom includes a large tiled walk-in shower, while the guest bathroom has a tub. The well-equipped kitchen boasts beautiful countertops and amenities, including a drip coffee maker. Step out onto the private balcony to enjoy sunrise views and the refreshing ocean breeze, complete with comfortable seating for soaking up the morning sun while sipping a warm cup of coffee to start your day. brbr**Pool and Outdoor Living...** brCommunity amenities include a heated Olympic-sized pool and a bubbling 20-person hot tub, as well as three tennis courts, one of which boasts the only clay surface in Key West. There are bathrooms near the pool for convenience, whether you want to enjoy a sauna soak or a quick rinse before heading back to the condo. A small community library and fitness center are also available. Spend your evenings under one of the many pavilions while grilling your dinner and enjoying the refreshing breeze from the Atlantic Ocean. Plus, bask in the sun on the property’s private beach or take a short two-minute walk to Smathers Beach, the largest beach in Key West! brbr**Parking...** brEach unit comes with an assigned parking space in the garage, subject to height restrictions. Limited outside parking spaces are available on a first-come, first-serve basis. brbr**Concierge Services...** brTake advantage of our concierge services to help plan activities for your trip. We can assist with bikes, scooter, and golf cart rentals, as well as a variety of excursions, including snorkeling, sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddleboarding, and much more. We can even stock your fridge with all the necessities before your arrival. brBook Activities /keywestattractionsfishingdiving/brbrbr **Cancellation...**br Bookings canceled at least 30 days before the start of the stay will receive a refund, minus a $250 cancellation fee.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$425.29

Escape to this charming 1BR, 2nd-floor condo in the heart of Historic Key West. Sleep soundly in a plush king bed with room for additional guests in a Queen bed and sofa bed, a spacious living area and a fully equipped kitchen. Lounge poolside under the palms, grill, or relax in the refreshing pool. No transportation needed, you're just steps from lively Duval Street, world-class dining, nightlife, and beaches. Perfect for a romantic getaway or a fun retreat, your island escape awaits!brbrHosted by Nautipussy!brbrThe spacebrWelcome to your perfect getaway in Historic Old Town Key West! This spacious second-floor condo is nestled in a secure, gated complex with just eight units, offering an intimate and peaceful retreat. Overlooking a sparkling pool with comfortable loungers, outdoor seating, and a grilling area, you'll love relaxing in this tropical oasis.brbrStep onto your private balcony, the perfect spot to sip your morning coffee or unwind after a day of exploring. Inside, the large one-bedroom suite features king and queen beds and a dedicated workspace, ideal for remote work or planning your Key West adventures. The living room includes a sleeper sofa, accommodating two additional guests comfortably.brbrThe fully equipped kitchen has everything you need to prepare meals, while the bathroom is conveniently located off the living room. Stay cool with ceiling fans and two air conditioning units throughout the condo. For entertainment, enjoy a flat-screen TV's in the living room and bedroom.brbrParking is hassle-free with two off-street spots available on a first-come, first-served basis. Limited free street parking is also an option, and a paid parking lot is just two blocks away.brbrWith its prime location, you're just minutes from world-class dining, shopping, nightlife, and Key West’s famous attractions. Whether you're here to relax or explore, this charming condo is the perfect home base for your island escape!brbrBook now and experience the magic of Old Town Key West!brbrGuest accessbrYou'll have access to the courtyard, pool loungers, outdoor seating, pool and grilling area.brbrOther things to notebrThis gorgeous condo is part of an 8 unit complex that share a refreshing pool in a nice tropical setting. Enjoy al fresco dining and charcoal grill for the ultimate outdoor poolside vacation experience.brbrAn outdoor motion activated light and camera is located at the rear emergency entrance.brbrThis listing has a strict cancellation policy and we highly recommend you consider trip insurance to protect your investment. Go to squaremouth and select a company and coverage of your choosing including cancellation for any reason (CFAR) coverage.brbrDeck reconstruction over the next few weeks (Dec & Jan) will make the front deck and staircase unavailable to guests. Access to the condo will be via the rear staircase only. We hope this doesn't cause too much incovenience.

Coral Palms Spacious 1BR Condo, King, Queen, Sofa Bed, Pool, Block to Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$193.19

Bohemian Breeze in lovely Key West is waiting for you at this cozy first floor, 2-bedroom condo. Nestled in the serene, gated community of the Truman Annex you are just steps away from the new Truman Waterfront Park, a short bike ride to Fort Zachary Taylor beach and only 2 blocks from the famously funky Duval Street. Enjoy the heart of Old Town Key West and all its charms! Stroll or bike to many of the historic sites such as Hemingway House, the Butterfly & Nature Conservatory and the Little Truman White House or take a relaxing sunset cruise. If you are bringing a vehicle you will have a secure parking space while you enjoy the many nearby activities. Make your holiday one for the books with a stay at our place in paradise.brbrAmenities: br-1 Queen and 2 Twin Beds (can be converted to a King) br-Secure WiFi Internet Access br-A/Cbr-Fully equipped kitchen with a drip coffee pot, Keurig, waffle iron, blender, microwave and a dishwasher br-Outdoor Grill br-Large, shaded patio br-2 Bicycles for Guests to use during their stay br-Smart Televisions with Cable TV in living area and main bedroom br-Bed Linens, Bath and Beach Towels br-Beach Chairs, Umbrella and Cooler br-Hairdryer br-Iron and Ironing Boardbr-Full Size Washer and Dryer br-Access to Shipyard Community Pool br-Reserved parking space br-Private entrance br-Contactless Check-In/Out

Bohemian Breeze - Shipyard Truman Annex condo in the heart of Old Town Key West

Key West, Florida, United States

Bed

1

Bath

4

Sleeps

$517.32

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrSHANG-RI-LA is a term for a utopia designed for life-long learning, happiness and fulfillment. There is no better place to find your happiness and fulfillment than a waterfront oasis on a little island at the farthest Southern tip of the US. This water view condo has been meticulously furnished with a modern coastal feel, with a front row seat to your own gorgeous views of the beach and the water beyond, with no end in sight. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors from the living room, and sunrise shadows from your bedroom balconies in the morning while relaxing on one of your comfy chaise lounges. This home is located in an upscale private community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the beautiful waters surrounding the island. Find your fulfillment at SHANG-RI-LA in Key West.brbrTHE LIVING AREA...brbrThe living room of SHANG-RI-LA is modern and bright, with plenty of light streaming in from the floor-to-ceiling glass doors. There's a large flat screen TV in case you can tear yourself away from the stunning views off your balcony to catch your favorite show. The living room sofa pulls out to an additional bed for extra guests. The kitchen has everything a good chef would need to prepare any meal. There's a dining table for six when you decide to heat leftovers and stay in. Your dining set on the balcony is the ultimate sunset dinner locale.brbrTHE POOL, THE BEACH & TENNIS...brbr1800 Atlantic offers Resort-style amenities, including an extra large Community Pool right downstairs. There are chaise lounges surrounding the pool for your comfort, and a cabana with restrooms for your convenience. Please note this is a shared pool with set rules, such as no music and no coolers. We ask that our guests be mindful of their neighbors and respect the rules.brbrFrom the pool, there's a walking path that leads to the on-site beach. The on-site beach offers a relaxing setting, with chaise lounges and soft sand. There is no direct water access from this beach, but Smathers Beach, Key West's largest public beach, is located within walking distance right next door. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. You'll also have access to the newly built fitness center and Key West's only clay tennis courts, both located on-site.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom: a King bed, a large flat screen TV, direct access to the balcony, and an oversized shower. brbr** Second Bedroom: Two Twin beds OR One King bed, a flat screen TV, direct access to the balcony, and access to the full second bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Community Jacuzzi Accessbr** Assigned off-street carport for 1 car (Parking Garage has a low clearance of 6'2)br** Key West's only clay tennis courtsbr** Handball courtsbr** Fitness Centerbr** Dry Saunasbr** Picnic areas with BBQsbr** Recreation rooms available for private partiesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** This complex has both visitors and locals living here, we expect our guests to be mindful & respectful of the posted rulesbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**SHANG-RI-LA @ THE BEACH** Oceanview Condo / Pool & Tennis + LAST KEY SERVICES.

Key West, Florida, United States

Bed

Bath

Sleeps

$563.68

Unique oceanfront living only 65 feet from the Atlantic!brbrThe Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. brbrThe large oceanfront balcony can be accessed from both the living/dining area and main bedroom. It also features central heat/air, cable TV, washer/dryer, a well- equipped kitchen, security entry and elevator access. There is one reserved parking space in the garage. There is elevator access to the condos above.brbrResort amenities include 2 ocean side pools (one heated), tennis court, outside cooking facilities, workout room and sauna. Non-smoking unit. Sleeps 4.brbrPlease note; the Key West Beach Club Condo Association requires additional registration, which includes providing copies of photo IDs for everyone over the age of 17, in advance of your arrival. Details will be provided along with your RKWV rental agreementbrbrNO CHECK-INs ALLOWED AFTER 10 p.m. at the Key West Beach Club.brbrBedding: 1 king, 2 twinsbrbr*Disclaimer: Due to the property's oceanfront location, please be aware that Key West experiences seasonal occurrences of fermenting turtle grass along the south shore of the island brought on by our southern winds in the summer. This is a natural phenomenon that is outside of our control.

Beach Club #104 - Unique oceanfront living with breathtaking views

Key West, Florida, United States

Bed