Vacation Condo Rentals By Owner In Key West, FL

$412.77

Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room

Key West, Florida, United States

Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently been renovated and features a new kitchen with granite counters, lovely open floor plan with vaulted ceilings. The elegant master bathroom has a spacious walk in shower. The master bedroom has a king size bed, the guest bedroom has 2 twin beds and for your convenience there is a queen pull out sleeper sofa in the living room. Both bedrooms and the living room have brand new impact sliding glass doors providing ocean views across the entire length of the unit. Enjoy the ocean breezes from your large private balcony.brThis property has a 4 night minimum stay requirement during the high season, any time of the week. There may be some times that a shorter gap will occur and we will then be willing to make an exception to the rule, you will be unable to book this online so please either call or e-mail us.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.

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$581.87

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**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse / Pool + LAST KEY SERVICES.

Key West, Florida, United States

ATLANTIC REFLECTIONS is a newly renovated water view condo that has been meticulously furnished with a modern tropical feel, with spectacular views of the neighboring nature preserve and the ocean beyond, with no end in sight. You'll be able to enjoy those famous Key West sunsets from the living room, and sunrise shadows from your bedroom balconies in the morning while relaxing on one of your comfy chaise lounges. ATLANTIC REFLECTIONS 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...brbrATLANTIC REFLECTIONS living room is modern and bright, with plenty of light streaming in from the floor-to-ceiling glass doors and reflecting form the floor-to-ceiling mirrors. 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 large sectional sofa pulls out to a Queen sleeper for extra accommodations. The kitchen has everything a demanding chef would require 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 en suite with oversized shower.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.

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$448.93

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**THE MELLOW MACAW** Cozy Condo Near Duval + LAST KEY SERVICES...

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThis colorful apartment is all you'll need for your stress-free stay in the Conch Republic. THE MELLOW MACAW is located right in Old Town near the famous Southernmost Point of the United States, two blocks from the Southernmost Beach, and just steps from Upper Duval Street. You couldn't be any closer to the nightlife and attractions of downtown (La Te Da and Banana Cafe are a block away, the Hemingway House is just down the street), and yet this tropical two bedroom retreat is tucked around the side of an Old Town home with its own private patio. You won't need a car, but should you decide to bring one you will have a private off-street parking space. brbrTHE PATIO...brbrThrough a quaint gate off Virginia Street, pass around a tall tropical tree and follow the path along to your private entryway. Through your hidden gate you'll be in a completely fenced private outdoor porch area with a full outdoor dining area. THE MELLOW MACAW is equipped with comfortable patio furniture sitting under a big shady umbrella, and a gas grill for preparing outdoor meals and enjoying happy hour just a quick walk to the attractions that await you on Duval Street. brbrTHE LIVING AREA... brbrOpening the front door of THE MELLOW MACAW you'll find a cozy, island-inspired home with an open living plan. As you enter the apartment, you'll be greeted with a brightly colored and comfortable sectional sofa in front of a large flat screen TV. The sectional pulls out to a Queen sized bed to sleep 2 extra guests. brbrTHE KITCHEN... brbrBeside the living area, the open kitchen is fully equipped with all the tools you'll need to whip up a meal at home. The kitchen is also equipped with an electric stove, oven, and a dishwasher for easy clean up after meals.brbrTHE ACCOMMODATIONS...brbr• Master Bedroom: King bed, full closet, large armoire, flat screen TV, and a private patio. brbr• Second Bedroom: Queen bed and flat screen TV.brbrThe shared hall bathroom was recently renovated and features a custom walk-in glass shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central A/Cbr• Ceiling Fansbr• Flat Screen TVs in Living Room and 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 and full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Private Gated & Lushly Landscaped Outdoor Patiobr• Propane BBQ Grillbr• Off-Street Parking in DrivewaybrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 6 adultsbr• Pets Not Allowedbr• 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.brbrNEED MORE SPACE... brbrAdd the rental of SUZY'S PARROT PERCH, the 2 bedroom apartment upstairs from THE MELLOW MACAW, to create a total of 4 bedrooms, 2 bathrooms, a private deck, and off-street parking.

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$311.79

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**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrIf you dream of waking up to expansive water views and island breezes, and walking out your front door right onto the streets of Old Town Key West in the center of it all - PROMENADE TO PARADISE is everything you are looking for. With a spacious layout, relaxed island-style furnishings, a semi-private gated pool, and three private balconies all your own, this beautiful condo truly is the ideal place to spend a vacation in paradise.brbrTHE PRIVATE WATERFRONT PATIOS...brbrAn island vacation begs for views of the calm blue waters of the Gulf, and in PROMENADE TO PARADISE, you won't have to leave home to enjoy the best scenery Key West has to offer. Wake up in the morning and have your coffee on one of three private balconies with water views, spend the day by the pool or exploring the island, and return home with the best seats for Key West's famous sunsets: the newly rebuilt spacious patio with space for you and your guests to have a sunset cocktail in Margaritaville.brbrTHE LIVING AREA and KITCHEN...brbrThe Mills Place building where PROMENADE TO PARADISE is located sits right on the waterfront in Truman Annex. Walk up a flight of stairs and you'll enter a bright and sunny open living area. A large leather sectional sofa, which can pull out to a queen sleeper surrounded by tropical floral artwork provides plenty of space for the group to gather in the living area in front of a flat screen high definition TV. The kitchen is open to the living area, separated by an island with bar seating. The kitchen island is unique, with the stove-top and oven set in, and additional counter space for cooking an island meal. There is plenty of cabinet space, and the kitchen is fully equipped with all of the tools and appliances you could need. The dining area has seating for up to six. Open up the French doors out to the two separate balconies on either side of the table for a truly luxurious island dinner overlooking the sunset complete with those tropical breezes.brbrTHE ACCOMMODATIONS...brbr• Master Bedroom: King bed, comfortable seating area, a flat screen TV, large walk-in closet, a private patio with views of the pool and the Gulf on either side, and an en suite bathroom with dual sinks, a large Jacuzzi-style tub, and a walk-in shower.brbr• Second Bedroom: Queen bed, a flat screen TV, and access to the second bathroom in the hallway with a walk-in shower.brbrTHE GATED COMMUNITY...brbrTruman Annex is the most exclusive private residence community in Old Town Key West. Located just off the main drag of Duval Street, Truman Annex is an oasis of calm, quiet streets lined with palm trees and beautiful Floridian homes. Within Truman Annex, the Mills Place complex is one of the only waterfront locations, and this condo is truly the front row seat to the Gulf. The units in the Mills Place complex share a large pool that gets plenty of sunlight all day, and is surrounded by comfortable padded chaise lounge chairs.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.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen Cable 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 and full cable is includedbr• Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Fully Fenced and Landscaped Private Yardbr• Community Pool Accessbr• Designated Off-Street Parkingbr• Queen Sleeper SofabrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 6 adultsbr• Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

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$156.11

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Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town

Key West, Florida, United States

Shipyard Pool ClosurebrThe Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. We expect the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026.brbrbrbrBest Deal in Truman Annex – Céad Míle Fáilte! br2 Bedroom | 1 Bathroom | Sleeps Up to 5 GuestsbrbrWelcome to Innis-free, our little slice of paradise in Key West—where you're greeted with Céad Míle Fáilte, an Irish expression meaning “a hundred thousand welcomes.” Whether you're traveling from near or far, we’re delighted to share our home with you.brbrNestled in the heart of the exclusive Truman Annex, our cozy ground-floor condo offers the perfect combination of comfort, convenience, and charm. With two bedrooms and one bathroom, the space comfortably accommodates up to five guests and is ideal for couples, families, or small groups of friends.brbrWhy You'll Love It Here:br Reserved parking—leave the car and explore on foot or by bikebr Steps from iconic spots: Green Parrot, Margaritaville, and Duval Streetbr A short ride to Fort Zachary Taylor State Park—home to the island’s best beachbr Relax in the community pool or unwind on your private back deckbr Enjoy tasteful decor, hardwood floors, and a new maplewood kitchenbrbrFrom lazy beach days to lively nights out, everything Key West has to offer is right at your doorstep. So kick back, soak up the sunshine, and enjoy a truly warm welcome—a hundred thousand times over.

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$291.71

/ Nightly

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**SUNSET DREAMS @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSUNSET DREAMS has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world at SUNSET DREAMS with a large balcony overlooking Florida Bay and the Gulf of Mexico beyond.brbrTHE PRIVATE GATED COMMUNITY...brbrSunset Marina is a gated community located on Stock Island, right off the entrance to Key West. The location is a great balance between being secluded in a private community yet still only a short Uber ride into the best of Old Town Key West. With your rental home at Sunset Marina you'll have plenty of space for parking, both covered garage space and visitor space, as well as access to the private waterfront community pool.brbrTHE LIVING AREA...brbrThis beautiful condo is an end unit with commanding views of the Florida Bay. No expense was spared in decorating this 1658 square foot condo, SUNSET DREAMS has been meticulously designed and furnished to a level you will seldom see in a vacation home. You'll have plenty of room to spread out, with a large main balcony, open living area, even a home office. The sofa pulls out to a queen bed for extra guests. The kitchen is completely equipped, with everything a good chef would need to prepare the most ambitious meals and even room for some sous-chefs.brbrTHE ACCOMMODATIONS...brbr• Master Bedroom: King bed, flat screen TV, direct access to the main balcony, private waterfront balcony, large walk-in closet, and an en-suite bathroom with twin vanities, an oversized shower and a Jacuzzi tub. brbr• Second Bedroom: Queen bed, flat screen TV, private waterfront balcony, and access to the shared full bathroom in the hall.brbr• Third Bedroom: Queen bed, flat screen TV, private waterfront balcony, and direct access to the shared full bathroom. brbrTHE HEATED COMMUNITY POOL and JACUZZI...brbrThe community pool area is a beautiful place to spend the day, with its setting right on the waterfront facing the marina and Florida Bay beyond. There are plenty of chaises and sitting areas and a cabana for your convenience.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen TVs in Living Room and 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 and 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 covered parking for 1 carbrbrOther notes:brbr• All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br• Additional interim cleanings availablebr• This property will accommodate up to 6 adultsbr• No Pets Allowed

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$196.42

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Ocean views and beach breezes at La Brisa's #303 West

Key West, Florida, United States

28 DAY MINIMUM RENTALbrbrLet the breeze of La Brisa cool you as you relax on your balcony overlooking the salt ponds, a natural water sanctuary. This residential condominium is situated opposite the largest beach on our tiny island of Key West, Smathers Beach, while offering many amenities of a resort hotel. Sunbathe next to a large kidney-shaped pool, with beautiful, tropical landscaping. Soak in the adjacent hot tub after a long match of tennis on La Brisa's very own court. On one of our very few, really cool nights, retreat to the dry saunas for warmth. The condominium units are designed to catch the breeze with exterior walkways leading to your front door opening up to the view of the balcony beyond the interior. brbrFeaturing two large bedrooms and baths, the interiors provide ample space for a small family or vacationing couples. All units feature central a/c with heat, cable TV, washer/dryers and well equipped kitchens with all the conveniences of home in a secured setting. Bedding: 1 king, 2 twinsbrbr1 Designated Parking Space in the Covered Bays below the units. Elevator access to the condos above.

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$160.48

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CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!

Key West, Florida, United States

SIMPLISTIC ELEGANCE...brEnjoy easy island living in this quaint and cozy Key West gem located in the attractive community of The Meadows. A charming hideaway tucked within quiet surroundings with the opportunity to fully live like a local!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brImmerse yourself in this cozy layout on the first floor with nautical accents and vintage Dade County walls throughout. Large windows attract incredible natural lighting in this cherry space with comfortable furnishings and a flat screen TV for lazy afternoons. A fully equipped and updated kitchen with a funky backsplash allow for all your meal prep and cocktail crafting to be enjoyed at a small table within the living space or out on the front patio. There is a coin laundry in the shed by the pool area.brbrSLEEPING ARRANGEMENTS…brStep through a modern barn door to find the a queen guest room with French doors that lead you out to the screened in patio for your morning cup of coffee. A very stylish full bathroom with gorgeous tile work and a walk in shower lies just off of the living room area. brbrOUTDOOR LIVING…brA second entrance from the kitchen area takes you out to your outdoor tropical oasis. Steps away you will find a friendly community pool (not heated) with plenty of loungers to soak up the island rays. Park your bike on the side of the building and stroll in town to meet old friends and new. There are local laundromat and laundry services are available nearby! brbrPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.brbrPETS...brThis is NOT a pet friendly property.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrAUTHENTIC KEY WEST...

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$653.43

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3-bedroom ocean view condo in delightful Key West with WiFi, AC

Key West, Florida, United States

Discover this delightful 3-bedroom gem in Key West. This charming condo features 1 king bed, 1 queen bed, and 2 twin beds, perfect for families or friends traveling together. With 2 bathrooms equipped with hair dryers and showers, guests can freshen up after a day of exploring. The cozy living room offers an additional space with a comfy sofa bed for extra guests. brWalk down the stairs and you are at Oceanside Marina where you can rent a wet slip or book a sport fish or center console for what Key West is known for. THE FISHING!! Connected to Oceanside Marina is Yellowfin Bar and Grill where you can enjoy a meal and even have your catch prepared for you. Within minutes there are 5 or more restaurants. Cuban, American, Italian, and Mexican restaurants... Something for everyone!! Just a short drive and you are at Duval Street where you can enjoy the Key West night life then return to your peaceful home away from home. If enjoying peace and quiet is more your style, Sit back and enjoy the ocean breeze from your large balcony. This property also comes with an assigned covered parking spot. We are happy to assist you in any way!

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$1880.65

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Harbor House Penthouse- A

Key West, Florida, United States

Summary:brbrHarbor House Suite A- Luxury 4BDR/4BA Penthouse SuitebrbrbrbrThe Space:brbrWelcome to Luxury Harbor House Suites, an exceptional NIGHTLY vacation rental property located in the heart of Key West's City Center. Our newly renovated property boasts 2,400 square feet of luxurious living space, featuring four large en-suite bedrooms, each exquisitely decorated in a modern coastal-chic style. The stunning 12 Ft ceilings in the living area provide an effortless flow between indoor and outdoor entertaining, making it the perfect space for creating memories that will last a lifetime. After a day filled with adventure, take a moment to unwind on your oversize porch and soak in the vibrant energy of the city center. As one of the closest properties to Mallory Square, Luxury Harbor House Suites offers the perfect vantage point to witness the iconic Sunset Celebration and experience the best of Key West's vibrant culture. We invite you to join us at Luxury Harbor House Suites, where luxury meets comfort for an unforgettable vacation experience.brbrbrbrSleeping Arrangements:brbr3 King size bedsbrbr2 Twin Bedsbrbr2 Sleeper SofasbrbrbrbrAdditional features:brbrCentral AC & ceiling fans throughoutbrbrStarter supply paper productsbrbrStarter set cleaning productsbrbrLinens, bath, and pool towelsbrbrKitchen cookware, dishes, flatware, glasswarebrbrWireless high-speed internetbrbrAT&T Uverse cable, smart TV capable thru-outbrbrHousekeeping services availablebrbrLaundry RoombrbrLarge Outdoor TerracebrbrPARKING IS NOT PROVIDED- parking can be found at 300 Grinnell Street, the PARK-N-RIDE garages or at the Mallory Square.

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$282.06

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**SUNDRENCHED REFLECTIONS @ SUNSET MARINA** Bayfront Condo + LAST KEY SERVICES..

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSUNDRENCHED REFLECTIONS is not far from Old Town, with access to all the attractions that Key West has to offer. Yet, you'll be in your own world with a large sundrenched balcony overlooking Florida Bay and the Gulf of Mexico beyond. brbrTHE PRIVATE GATED COMMUNITY... brbrSunset Marina is a gated community located on Stock Island, right off the entrance to Key West. The location is a great balance between being secluded in a private community yet still only a short Uber ride into the best of Old Town Key West. With your rental home at Sunset Marina you'll have plenty of space for parking, both covered garage space and visitor space, as well as access to the private waterfront community pool.brbrTHE LIVING AREA... brbrThis distinctive 1658 square foot condo is an end unit with commanding views of the sunsets over the Florida Bay. SUNDRENCHED REFLECTIONS has been meticulously designed and furnished to a level you will seldom see in a vacation home, with fresco-style murals on the walls and thoughtful details everywhere you look. There's plenty of room for everyone at SUNDRENCHED REFLECTIONS, with a large main balcony, open living area with a 65 inch flat screen TV and separate bar area. The kitchen is completely equipped, with everything a good chef would need to prepare the most ambitious meals and even room for some sous-chefs.brbrTHE ACCOMMODATIONS... brbr• Master Bedroom: King bed, flat screen TV, direct access to the main balcony, private waterfront balcony, large walk-in closet, and an en-suite bathroom with twin vanities, an oversized shower and a Jacuzzi tub. brbr• Second Bedroom: Two Twins OR One King bed, flat screen TV, private waterfront balcony, and access to the shared full bathroom in the hall.brbr• Third Bedroom: King bed, flat screen TV, private waterfront balcony, and direct access to the shared full bathroom. brbrTHE HEATED COMMUNITY POOL and JACUZZI... brbrThe community pool area is a beautiful place to spend the day, with its setting right on the waterfront facing the marina and Florida Bay beyond. There are plenty of chaises and sitting areas and a cabana for your convenience. brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen TVs in Living Room and 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 and 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 covered parking for 1 carbrbrOther notes:brbr• All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br• Additional interim cleanings availablebr• This property will accommodate up to 6 adultsbr• No Pets Allowed

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$514.26

/ Nightly

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**FOLLOW THE SUN @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrFOLLOW THE SUN is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own 28-foot balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors. FOLLOW THE SUN 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 FOLLOW THE SUN is comfortably furnished, with plenty of light streaming in from the floor-to-ceiling glass doors. There's a large flat screen TV, for those times you aren't marveling at the breathtaking Key West sunsets from your private balcony. The living room sofa pulls out to a Queen sleeper to accommodate two extra guests. The kitchen has everything a good chef would need to prepare any meal. The dining table will seat six comfortably, and there's also a kitchen bar that seats four more.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. 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.

3

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2

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6

Sleeps

$400.03

/ Nightly

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High Tide awaits your next visit upgraded condo close to Smathers Beach

Key West, Florida, United States

2 Bedroom Garden-View Condo at 1800 Atlantic – Key West, FL brYour Tropical Getaway Awaits!brbrExperience the ultimate in comfort and relaxation at this beautifully appointed condo, perfect for a family vacation or a group of friends. Nestled in a lush tropical setting, this spacious 2-bedroom, 2-bathroom garden-view unit has everything you need for a stress-free stay in Key West.brbrFeatures Include:brbr Spacious private balcony overlooking botanical gardens & tropical courtyardbrbr Fully equipped, full-size eat-in kitchenbr Washer & dryer in unitbr Large dining area with seating for 6br King bed in the master bedroombr Two twin beds in the guest bedroombr Queen pull-out sleeper sofa in the living roombr Two full bathroomsbrbrResort-Style Amenities at 1800 Atlantic:brbr One of the largest heated pools on the islandbr Oversized 20-person Jacuzzibr 3 Lighted tennis courts (including 1 clay court)br Secure, assigned parkingbr Direct oceanfront property with easy access to the AtlanticbrbrEnjoy the comforts of home with the luxury of a tropical resort — just minutes from all that Key West has to offer.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.

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$158.76

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Condo

A Southard Pearl at the Truman Annex in Key West

Key West, Florida, United States

A Southard Pearl is a charming condo in the Shipyard in the Truman Annex and is outfitted with washer/dryer, pots/pans, towels, linens, central air conditioning, off street parking, and heated pool access. Just inside Truman Annex's main gate on Southard Street, this is a well-appointed, one-bedroom, second floor, end unit with quiet three-side exposure to tropical views and breezes. Southard Pearl, decorated with private art and lots of mirrored walls, boasts a large rear deck with a 50% overhang to protect you from the elements while enjoying the shade of lush palm trees and other vegetation. Shipyard Condominiums are located in the prestigious gated community of the Truman Annex in Key West’s Old Town neighborhood. The condos are located 2 blocks from Duval Street and many Key West attractions. The properties are also ¼ mile walk//drive/scooter, etc. from Fort Zachary Taylor State Park and Beach. Full access to a heated community pool and assigned off street gated parking.brPlease note: This property requires a 28 night minimum stay.

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2

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Exceptional(2)

$318.32

/ Nightly

Condo

A Poolside Cabana at the Key West Golf Club!

Key West, Florida, United States

A Poolside Cabana - Stay at the only 18-hole golf club in the Florida Keys and enjoy the lush tropical foliage and resort style amenities! The properties provide open living areas downstairs and comfortable bedrooms upstairs. Enjoy the balmy southerly breezes across the front or back screened in porches while sipping your favorite lemonade or Mojito and enjoy the relaxing Caribbean lifestyle as your stress melts away. Amenities include two community heated pools, a gym, and parking for up to two vehicles. Small pet considered with owner approval and additional non refundable fee. br**THIS HOME RENTS FOR 28 NIGHTS MINIMUM**

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$240.32

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Condo

Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom

Key West, Florida, United States

Welcome to Keys to Paradise – Your Cozy Retreat in the Heart of Key West!brbrLocated in the charming Shipyard Condominium Complex at Truman Annex, this quaint and well-appointed first-floor condo offers the perfect blend of comfort and convenience. Featuring two bedrooms and one bathroom, it’s ideal for families or friends looking to explore Key West’s best attractions just steps away!brbrInside Your Home Away From Home:brbrSpacious Living Area: Relax on new full-size sofa (sleeper included), two comfy chairs, and enjoy your favorite shows on the 50” flat screen TV.brbrDining Room: Full-size table with seating for four—perfect for meals or game nights.brbrFully Equipped Kitchen: Includes refrigerator, dishwasher, oven, coffee maker, blender, toaster, and all the essentials you need.brbrGuest Bedroom: Two twin beds that can convert into a king on request, a closet, dresser, full-length mirror, and a flat screen Firestick TV.brbrMaster Bedroom: Queen bed, 50” flat screen TV, closet, dresser, and full-length mirror.brbrBathroom: Full-size shower/tub combo, vanity, and toilet.brbrLaundry Closet: Washer, dryer, and cleaning supplies for your convenience.brbrStep Outside:brbrEnjoy a huge back deck with seating, a table, umbrella, and two cruiser bikes to explore the island. Lush, mature landscaping surrounds the condo, creating a serene environment with walking paths and easy pedestrian access through Truman Annex.brbrCommunity Perks:brbrAssigned parking spot right in front of your unit.brbrSecure gated community with code entry.brbrPool area with loungers, towels, and restroom access.brbrAccess to Truman Annex pedestrian gates via foot gate keys.brbrPrime Location:brbrWalk or bike less than 2 blocks to Truman’s Little Whitehouse and the iconic Green Parrot. Less than 1 mile from Fort Zachary Taylor Beach, Mallory Square, Duval Street, the Southernmost Point, Hemingway House, and more!brbrLeave your car behind and enjoy Key West at your own pace. Whether it’s your first visit or a beloved return, Keys to Paradise offers the ideal home base for your unforgettable island getaway.

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$589.32

/ Nightly

Condo

Beach Club #103 - Unique oceanfront living with breathtaking views

Key West, Florida, United States

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. brbrThis spacious 2 bedroom unit features a large oceanfront balcony accessed from both the living/dining area and master bedroom. The unit features central heat/air, WiFi, cable TV, washer/dryer, a well equipped kitchen, 2 baths, security entry, one reserved parking space in the cover garage area and elevator access.brbrResort amenities include two ocean side pools (one heated), tennis court, outside cooking facilities, workout room and sauna. NON SMOKING Sleeps 4-6brbrPlease 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 agreement.brbrNO CHECK-INs ALLOWED AFTER 10 p.m. at the Key West Beach Club.brbrBedding: 1 king, 1 queen, 1 twin, 1 sofa sleeperbrbr*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.

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$415.35

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Antigua Retreat- 2BR 2BA waterfront condo w/ pool & boat slip

Key West, Florida, United States

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrBOAT SLIP INFORMATION:brOne boat slip is included with this Retreat. Each Retreat can only accommodate one boat; no exceptions. Trailer parking is not available on property. Trailer parking and additional boat slips are available across the harbor at the City of Key West Marina. Please contact the dock master’s office to make arrangements for trailer storage and/or additional boat slips atbrbrFEATURES:brBedrooms: 2 ( 1 king, 2 queens in 2nd bedroom) -THE SLEEPER SOFA IS NOT RECOMMENDED FOR ADULTSbrBathrooms: 2 en suitesbrLocation: Garrison Bight Marina off Eisenhower DrbrSquare Feet: 1215brParking: 2 parking spaces includedbrAmenities: Wifi, TVs, in-unit laundry, 1 complimentary boat slip, water viewsbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

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$885.94

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3 bedroom 2 bath Ocean front condo on marina with opt boat slip.

Key West, Florida, United States

3 bedroom 2 bathroom Ocean front condo. Full service marina on site. Restaurant/bar on site. Pool and spa Optional 50’ boat slip for additional rental. Balcony over looks the ocean. One private parking space.

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$405.05

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Casa Atlantica: A one bedroom condo on the Atlantic shore of Key West

Key West, Florida, United States

Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perched on the very edge of the turquoise waters of the Atlantic. Located on the quiet end of a waterfront townhome community, this property features simply the best views you will find in Key West. Best of all, Casa Atlantica is located just a short bike ride from Duval Street and the Historic District, so you get the peace and quiet of the tranquil shore without sacrificing access to Key West’s unsurpassed restaurants, shops, and attractions.brbrOpen the door to this property and you are welcomed by an entire wall of floor-to-ceiling windows, giving you unrestricted access to the most breathtaking view in the Keys. Slip outside on to the large, private patio and enjoy the warm sunshine and salty breeze of the natural shoreline. Playful pelicans and majestic egrets swoop and dive into the cobalt-blue water directly in front of you! This is true coastal living at its best.brbrThe large patio doors can be left open to allow the ocean breeze in to the spacious, comfortably furnished living area, which features a flat panel television and a sizeable dining area with a wet bar. Down a short hallway is the fully equipped kitchen with a glass-top range. The large, unique bathroom includes conveniently separated areas for the sink and commode, as well as a massive tub for soaking. The tranquil bedroom contains a king sized bed and heavy drapes for those mornings you want to sleep in. Another patio can be accessed from both the bathroom and bedroom areas. The entire home features distinctive, Adobe-style rounded walls with built-in furniture and charming brick tile floors. The whitewash walls reflect the lovely natural light and create an effect that is fresh and soothing to the senses.brbrIf you want to put your toes in the sand, head downstairs to the charming tiki hut right by the water. This property also has a shared washer and dryer and limited street parking. Please be aware that this unit is accessible only via 2 flights of a centrally located staircase.brbrIf you are dreaming of a vacation by the shore, it just doesn’t get any closer than Casa Atlantica!brbrBedding: 1 Kingbrbr*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.

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1

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