Vacation Villa Rentals By Owner In Key West, FL

$192.25

A SUNSET VIEW at The Truman Annex in Key West

Key West, Florida, United States

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s Old Town area. brThis 1st floor condo is located 2 blocks from Duval Street and all the Old Town Key West attractions and a ¼ mile from Fort Zachary Taylor State Park and Beach. This property is outfitted with washer/dryer, pots/pans, towels, linens, central air conditioning, off street parking, and pool access. This 2BR 1BA adorable first level condominium has an updated kitchen with Stainless Steel Appliances, Flat screen TV in the living room and both Bedrooms. This property also includes assigned off street parking and 24 hour security.brPlease note: This property has a 28 night minimum stay

2

Bed

1

Bath

5

Sleeps

$339.46

/ Nightly

Private Vacation Home

Papa's Casita in Downtown Key West

Key West, Florida, United States

Even Hemingway would have loved this place! Amazing renovation from top to bottom of this mid 1800's historic home located across from the Ernest Hemingway Home & Museum. Right in the heart of Old Town Key West, and only one block from Duval Street, this property has surprisingly wonderful privacy with lush tropical gardens and a new in-ground pool. You don't have to worry about finding a parking spot, as there are two off street parking spaces and even room for scooters. The property has 3 bedrooms and 3 full baths, a chef's kitchen with stainless, granite and hard wood floors, French doors leading out to the lush landscaped outdoor living space and so much more. This property is rented monthly only (28 night minimum)

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Select Dates for Price

Condo

ANNIE'S HIDEAWAY at The Truman Annex in Key West

Key West, Florida, United States

This charming one bedroom, one bath 2nd floor property features an Olympic queen in the master bedroom and a large covered deck off the the living room, updated bath and bedroom. The living room, which includes a sleeper sofa, is close to the kitchen, and dining areas. Both the living room and bedroom have televisions... | This lovely property is also close to the pool and and private assigned parking. Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located 1/4 mile from one of the best beaches on the island. The Shipyard units are single level condominiums which have private courtyards on the first level or balconies on the second level. All properties are outfitted with washer/dryer, pots, pans, towels linens, have central air conditioning, off street parking and pool access. brPlease note: This property will require a minimum of a 28 night stay.

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$352.5

/ Nightly

Private Vacation Home

Charming Old Town Bungalow

Key West, Florida, United States

Charming two story, 3 Bedroom 3 Bathroom. Renovated home built in 1908, on a corner lot in Historical Old Town Key West. This property was once a tobacco barn at the turn of the century. Nine foot ceilings, crown molding, Dade County Pine, lush landscaping, multiple porches, gas stove, huge food pantry, brick walkways, off street parking space, private back yard, upstairs private observation deck.brWalk or ride your bike everywhere -Live like a local and come enjoy Key West! Close to restaurants, galleries and Duval Street.

3

Bed

3

Bath

6

Sleeps

$674.17

/ Nightly

Apartment

The Maloney - Luxury Modern Downtown Penthouse

Key West, Florida, United States

Summary:brbrWoven throughout this 2,000+ square foot luxury penthouse is a story that can only be revealed by experience.brbrbrbrThe Maloney encompasses the entire second story of the historic red brick building on the corner of Fleming and Simonton. Originally built in 1908 as the first pharmacy in Key West, the building now houses two penthouse units and a first-floor clothing and arts boutique. brbrbrbr**The Maloney is only available as a monthly rental at this time. All bookings require a 30-day minimum stay.**brbrbrbrThe Space:brbrIdyllic Key West mornings are sure to take place at the Maloney, where the soft light of sunrise meanders through the 19th century brick framed windows, offering the perfect pairing for a velvety cup of cafe con leche and a slow drip of energy to start your day. Enjoy vibrant Key West evenings where the curated collection of local paintings and carvings compete with the glow of the 100 year-old Dade county pine floors make the perfect setting to host a quiet dinner or serve cocktails to friends.brbrbrbrThe Neighborhood:brbrLocated on one of the best corners in Key West, the Maloney places our guests within one block of award-winning restaurants, coffee and sandwich shops, wine bars, craft cocktail bars, a local grocery store and world-famous Duval Street.brbrbrbrGetting Around:brbrOne of the best parts of staying in Key West is how close in proximity you are to everything. Don’t feel like walking Peddle your way to breakfast, or take a bike ride along the water at sunset. Rent your bikes from Fury or Island Bicycles who offer both pick up & drop off services to your home! Feel like you’re on island time when you rent from Minty’s where you can enjoy exploring Key West on a scooter or golf cart. In addition to these non-traditional modes of transportation, you can also Uber, Lyft or Taxi to your next destination. Pink Taxi is an easy, reliable and affordable way for getting to your rental from the airport.brbrbrbrOther Things to Note:brbrThere is no parking included with your stay.brbrMid-stay cleans are available upon request.

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$707.57

/ Nightly

House Boat

51' Luxury Yacht in Key West

Key West, Florida, United States

Introducing Andiamo our 51' power catamaran.brYou and your guests will have exclusive use of this amazing boat to yourselves and can come and go on the yacht anytime, day or night. We are pet friendly, our pet fee is $25.00 per pet per night up to 2 dogs. There is also a fully refundable cleaning and damage deposit required. Service animals at no charge per night.brbrThe yacht stays docked, the entire reservation, at the Perry Hotel, which invites you to complimentary use of two stunning waterfront swimming pools, live music, three restaurants, complimentary shuttle service, & more. brbrAble to sleep 9 adults and carry up to 12 passengers on a day charter Andiamo features :brbrFour beautifully appointed staterooms, each with a private en-suite bathbrOne stateroom includes a bonus single top bunk, ideal for a childbrExclusive use of the entire yacht—experience complete privacy and elevated comfortbrSophisticated interior with designer finishes and upscale amenitiesbrExpansive deck space for sunbathing, al fresco dining, or sunset cocktailsbrThe galley has windows that provide a 360% view with plenty of sunlight.brLarge sliding glass doors opens the galley to a large cockpit where there iss ample seating to entertain all your guests.brThe flybridge deck and helm station with an outdoor kitchen equipt with a sink, fridge and BBQ grill is perfect for those sunset cocktails while you watch the sun dip below the horizon,brLocated at The Perry Marina, offering resort-style services and luxury marina access you truly have everything you need.brbrEnhance your stay with a bespoke charter experience—from sunset sails to full-day excursions, our luxury sea charters are tailored to your desires. brbrDue to local regulations, it is required that you choose at least one of the following options during your reservation: a four-hour excursion, an eight-hour excursion, a ten-hour excursion, or a 24-hour excursion.brbr- 4-hour excursion: $1750+tax & gratuitybr- 6-hour excursion: $2050+tax & gratuitybr- 8-hour excursion: $2450+tax & gratuitybr- 24-hour excursion: $3200+tax & gratuitybrbrPlease note that the cost of the excursions must be paid directly to our company at the time of booking. The prices listed above include the captain's fee and fuel, however, does not include tax or gratuity. Contact us directly to start planning your unforgettable day on the water.brbrANDIAMO isn’t just a yacht—it’s your private escape to paradise.brbrReserve your stay today and experience Key West in unparalleled style.

4

Bed

4

Bath

9

Sleeps

$900.0

/ Nightly

Hotel Resort

Two-bedroom townhouse overlooking the harbor. ONLY AVAILABLE Nov. 8 - Nov 15

Key West, Florida, United States

Two story townhouse with two bedrooms, pull out couch, full kitchen, three bathrooms. Overlooking the harbor with full view of beautiful Key West sunsets and dock activities. A short walk to Duval Street for shopping and restaurants. Room location is shown with two red dots in the building elevation picture. Oceanfront view of Sunset Key from your deck.

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$237.96

/ Nightly

Condo

Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool

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 EXCEPTIONSbrbrbrFEATURES:brBedrooms: 2brBathrooms: 2brLocation: Truman Annex at the Shipyard CondosbrSquare Feet: 780brParking: 1 reserved parking space in gated parking lotbrAmenities: Wifi, TVs, in-unit laundry, private balcony, shared pool, within walking distance to shops and restaurantsbrbrbrTHINGS 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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$177.79

/ Nightly

Condo

Florida Escape 2 bdrm monthly spacious resort amenities Key West Mid Town

Key West, Florida, United States

Welcome to our piece of paradise in Key West!brOur beautifully maintained, fully tiled 2-bedroom condo is your perfect home away from home. Newly furnished in 2017, it features a bright and inviting living space, including large HD Smart TVs in both the living room and the master bedroom for your entertainment.brbrEnjoy the convenience of a full-size, fully equipped kitchen, in-unit washer and dryer, and high-speed wireless internet. Your stay also includes one assigned garage parking space—perfect for your car or bikes.brbrThe complex offers resort-style amenities including a stunning Olympic-size heated pool, relaxing jacuzzi, a well-equipped fitness room, and lush botanical gardens. Tennis enthusiasts will appreciate the three lighted courts, including one clay court.brbrIdeally located next to Smathers Beach on the Atlantic side of Key West, we’re just two miles from Downtown and Mallory Square. Whether you're escaping to Key West for the winter sunshine or soaking in the endless summer, our condo is the ideal spot to relax, unwind, and enjoy island life.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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$246.24

/ Nightly

Private Vacation Home

PELICAN'S PERCH Summer Rates!!!!

Key West, Florida, United States

Shipyard Condominiums are located in the prestigious gated community of 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 from Fort Zachary Taylor State Park and Beach. The property is outfitted with washer/dryer, pots/pans, towels, linens, have central air conditioning, off street parking, and pool access. This home is a 2 story style townhouse. Pelican’s Perch is a tropical, Caribbean-themed cottage. The kitchen is equipped with Stainless Steel Appliances. Take a three-minute walk to Duval Street for dining and entertainment, a five-minute walk to Sunset Pier, a 10-minute walk to Fort Taylor Beach, a one-minute walk to the Truman Annex pool or, simply stay put and relax. Situated on one of Key West’s most beautiful streets, its front porch is a great place to watch the world go by while rocking in the chairs and viewing parades and Key West's colorful characters:) For those moments when you want to catch some rays, read or dine in peace and quiet, the back porch is one of the largest, quietest and most private in the entire Truman Annex. Surrounded by trees, it overlooks a tropical park, has two lounge chairs and a dining table with room for six. Inside, you can enjoy three flat-screen televisions, wireless internet, brand new tropical Caribbean furnishings and art. When it’s time to cook that fresh catch, Pelican’s Perch features a gas grill, fully-equipped kitchen, and a choice of an indoor or outdoor dining area. This is the perfect cottage for the selective renter. See you soon!brIncludes one assigned parking space. brPlease note: This property requires a 27 night minimum stay.

2

Bed

2

Bath

6

Sleeps

$2137.5

/ Nightly

Hotel Resort

2 Sunset Harbor Resort, Pool, Hot Tub, In Town!

Key West, Florida, United States

Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and beautiful contemporary design creates an environment of relaxation and restoration. Guests are encouraged to slow down and relax, to dip into the outdoor pool and whirlpool hot tub while soaking up some famed Floridian rays. Guests will also receive privileges at the adjacent Hyatt Key West Resort and Marina, offering even more ways to keep occupied even on your off days.brbrThe right size, the perfect view and the must-have amenities... Hyatt Sunset Harbor Resort's residences become the perfect home-away-from-home during your stay in Key West! Classic studios offer a king-size bed, casual living area, TV and DVD player. The one-bedroom tropical-style residence features a deluxe queen bed, fully-equipped kitchen, dining area, ceiling fans, seating area with TV, stereo, DVD player and private balcony. The beautiful two-bedroom residence is even more luxe, and includes a master suite with king-sized bed, adjoining bath and spa tub, a guest suite with queen bed and full bathroom. In addition, enjoy a fully-equipped kitchen, seating area, TV, DVD player and balcony!brbrHyatt Sunset Harbor isn’t just another Key West property - it’s in the heart of Old Town, the heart and soul of one of America’s most treasured vacation destinations. Nearby, you can also enjoy Duval Street shopping or nightlife and Mallory Square. Of course, if you're looking for more natural pursuits, you have plenty of options - Key West is a haven for fishers, and the unique ecosystem is well-suited to those seeking to explore by foot or bike. Plenty of unique attractions await those looking for a change of pace - check out the The Harry S. Truman Little White House, Key West Aquarium, Key West Lighthouse Museum and Mel Fisher Maritime Heritage Museum!brbrA few things to note.... The resorts require a credit card and Valid ID at check-in to cover incidentals. Please note parking fees may apply and are not included in the price quoted here. The room view and bed may vary and is not guaranteed here unless agreed upon before booking. If you would like an upgrade to a specific view or bed please let me know and if available I can do that, additional fees may be required. Additionally some resorts have various towers/buildings and may vary, please check with us in advance to discuss the view/building/unit and. Finally, Tourist Accommodation Taxes must be paid directly to the resort; this is standard procedure for resorts.brbrResort policies and rules Resort will provide the information

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Bath

Sleeps

$386.19

/ Nightly

Private Vacation Home

SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w/ Pool!

Key West, Florida, United States

AUTHENTIC KEY WEST AMBIENCE...brThis fully renovated mid-century jewel pairs modern allure with classic White Street Gallery District charm. Exhale your worries as you enter this serene and private neighborhood. You are a small distance from the vibrant pulse of downtown Key West so you'll enjoy both island peace and the unique excitement of the Conch Republic. This idyllic retreat is perfectly situated just minutes from Old Town, the historic marina and stunning white sandy beaches. Immerse yourself in the pinnacle of Key West lifestyle!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE.brbrDETAILS AND AMENITIES...brEnter the home that lies beyond your privacy fence and embrace your cozy oasis that envelops you with mature tropical foliage and a refuge from reality. Your light-filled living room beckons you inside with its island chic decor, plush furnishings and a wall mounted TV. Merge indoor and outdoor living spaces when you open your sliding doors to the pool and garden. The streamlined and sparkling kitchen overlooks the living area and captivates your inner foodie with every modern culinary appliance and tool you'll require for crafting festive meals and adult concoctions for your friends and family. The living/kitchen area offers a cafe table for 2 as well as kitchen counter seating for 3. Travel down the bedroom hallway where you'll find a washer/dryer closet. This home is equipped with Youtube TV. brbrSLEEPING ARRANGEMENTS...brDelight in three bedrooms that each have its own updated en suite shower bathroom - the second bedroom equipped with a wall mounted TV and both king rooms with sliding doors that lead to the outdoor area. A full bathroom with a shower/tub combination resides in the hallway. brbrOUTDOOR LIVING...brYou will enjoy hours of peaceful repose in your private garden with a heated pool. Nap on one of the loungers in the shade of lush palms cooled by balmy breezes and kick back with your loved ones by the fire pit. A grill and outdoor chairs invite you to gather under tropical stars with an iced cocktail in hand.brbrPARKING...brThere is off street parking available for this home.brbrPETS...brDogs are considered up to 15 lbs only and a pet fee is required. Please include the size and the breed in the comments when inquiring. 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 offered only 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.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).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!brbrISLAND TRANQUILITY RESIDES HERE…

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$1738.13

/ Nightly

Apartment

Key West Suites Hotel # 205

Key West, Florida, United States

Key West Suites HotelbrbrWelcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both Duval and Southard Streets. brbrThe apartment boasts 10-foot ceilings with fans, 2 King beds plus a Queen pull out leather sofa bed, huge 55-inch Samsung 4k smart tv, HD cable, full kitchen with pots, pans, plates etc., fridge with ice maker, stove/range, large windows looking onto Duval street, extreme speed Wi-Fi and a luxury shower for rinsing off your salt of the sea. brbrThe building once housed the Chrysler/Desoto car dealership, a furniture store, and later a clothing store when the Beatles came to make a purchase which caused the cashier to pass out on the floor. It has since been refurbished into a beautiful art gallery, two restaurants, a bar, and the newly renovated apartments upstairs. The stately solid concrete building is extremely quiet so that you can’t really hear much of Duval despite being right on Duval. brbrThe corner of Southard and Duval is right downstairs, and from there you can reach in near equal distance Fort Zachary state park beach, Mallory Square, Hemmingway’s house, and the Southernmost point. brbrYou must be able to bring your own luggage up two flights of stairs as it’s on the second floor, and there is no elevator to the historic building. brbrParking is public on the street at metered spaces. You must provide your own parking. The cheapest way to park is to first unload your car at Key West Suites Hotel after paying the meter, then park and pay at the City owned “Park and Ride” corner of Grinnell and Caroline Street, then simply walk everywhere. You can walk from the garage to the unit or keep the parking stub and ride their free shuttle. brbr

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Bath

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$1738.13

/ Nightly

Apartment

Key West Suites Hotel #201 on Duval

Key West, Florida, United States

Key West Suites Hotel #201brbrWelcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both Duval and Southard Streets. brbrThe apartment boasts 10-foot ceilings with fans, 2 King beds plus a Queen pull out leather sofa bed, huge 55-inch Samsung 4k smart tv, HD cable, full kitchen with pots, pans, plates etc., fridge with ice maker, stove/range, large windows looking onto Duval street, extreme speed Wi-Fi and a luxury shower for rinsing off your salt of the sea. brbrThe building once housed the Chrysler/Desoto car dealership, a furniture store, and later a clothing store when the Beatles came to make a purchase which caused the cashier to pass out on the floor. It has since been refurbished into a beautiful art gallery, two restaurants, a bar, and the newly renovated apartments upstairs. The stately solid concrete building is extremely quiet so that you can’t really hear much of Duval despite being right on Duval. brbrThe corner of Southard and Duval is right downstairs, and from there you can reach in near equal distance Fort Zachary state park beach, Mallory Square, Hemmingway’s house, and the Southernmost point. brbrYou must be able to bring your own luggage up two flights of stairs as it’s on the second floor, and there is no elevator to the historic building. brbrParking is public on the street at metered spaces. You must provide your own parking. The cheapest way to park is to first unload your car at Key West Suites Hotel after paying the meter, then park and pay at the City owned “Park and Ride” corner of Grinnell and Caroline Street, then simply walk everywhere. You can walk from the garage to the unit or keep the parking stub and ride their free shuttle. brbr

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$158.76

/ Nightly

Condo

SUN, SEA & SKY at Truman Annex in Key West

Key West, Florida, United States

Located in the desirable Truman Annex community, this beautifully maintained second-story Shipyard condo offers the perfect blend of island charm and modern comfort. Featuring one spacious bedroom with a king size bed, a small loft area with a sofa sleeper, a modern style living area, and a private balcony. This tropical retreat is ideal for a vacation escape to paradise. Nestled just steps from Duval Street, Fort Zachary Taylor Beach, and the Key West Historic Seaport, you’ll enjoy easy access to world-class dining, shopping, and entertainment—while still enjoying the quiet serenity of a gated community. The property is outfitted with washer/dryer, pots/pans, towels, linens, have central air conditioning, off street parking, and pool access. brPlease note: This property requires a 28 night minimum stay.

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Sleeps

$1032.46

/ Nightly

Private Vacation Home

Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!

Key West, Florida, United States

Key West Hideaway is an Historic home from 1874, completely renovated. Two upstairs Q memory foam mattress bedrooms, 2 Q memory foam mattress downstairs bedrooms. Each bedroom has a safe, Smart TV, Amazon Alexa, private bath. Q sleeper sofa with 5” memory foam mattress in LR. 76” Smart TV in LR, 32” Smart TV’s in BR’s, Amazon Alexa, Bose bluetooth speaker, full gourmet kitchen, rear veranda. 2 heated pools. 1/2 block off world famous Duval Street. On a quiet 2 block lane. CVS (24 hour) and Subway are across Truman Ave. Moped, bicycle, electric car rental at corner. If you rent from them, they will give you free ride to airport upon departure! Multiple restaurants, bars, dessert bars within walking distance. We are the most centrally located guest accommodations close to Duval but nice and quiet! Key West Hideaway is a 2 story, 1874 historic, private home with front and rear private porches. It is a 4 bedroom/4 bath house with Q sleeper sofa. You have access to 2 heated pools, gazebo with fun games. Use of W/D's after 5pm. There is also a totally private outdoor shower with hot/cold water to use anytime! Housekeeping and groundskeeping/maintenance on site daily from 9-5. We are 1/2 block off world famous Duval Street and Truman Avenue but on a nice quiet 2 block lane in Historic Old Town with other guesthouses and vacation rentals. Very safe, quiet and convenient to all Key West has to offer. Rent a bike, moped or electric car if you don't feel like walking. However, you will be in walking distance of most things in Key West!

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Bath

Sleeps

$312.76

/ Nightly

Apartment

Lofted 1 bedroom suite right off Duval St

Key West, Florida, United States

Welcome to sweet paradise! Located on Petronia Street, the Orange Blossom Suite is in close proximity to all the fun-filled action of Duval St; however, it is private enough to not hear any of it! Orange Blossom Suite shares a huge back patio and BBQ Grill with one other suite (Deckside Suite; also managed by us). Walk to fine dining or cook your own meals in your fully-equipped kitchen that includes a stove, oven, dishwasher, microwave, blender, and toaster! The loft bedroom has an ultra-comfy king-sized bed, but there is a also a full-sized sleeper sofa in the living area. brbrPLEASE NOTE THAT THIS PROPERTY DOESNT HAVE A POOL.You may use the pool at Dante’s if you utilize their food and beverage services or you may purchase a day pass using the link below at any of the hotels located near your rental. br brhttps://www.resortpass.com/s/us/fl/key-west/pool search_term=Key+West%2C+Florida&city_alias_id=26brbrOrange Blossom Suite is one of three units that comprises the group property Conch Republic Cottages. The three cottages can be booked separately or as a group.brbr*There are stairs to the loft master bedroom. Orange Blossom Suite may not be suitable for people unable to climb stairs well.*

1

Bed

1

Bath

4

Sleeps

$1540.13

/ Nightly

Private Vacation Home

Palmwater Retreat – A Boater’s Dream

Key West, Florida, United States

Palmwater Retreat – A Boater’s Dream...Your Luxurious Key West Escape Awaits!brbrNestled in the exclusive Key Haven neighborhood, just minutes from the vibrant energy of Key West, this stunning five-bedroom, four-and-a-half-bathroom waterfront home offers the ultimate tropical retreat. Whether you're seeking a peaceful getaway or an adventure-filled escape, this spacious 4,000+ square foot oasis is the perfect destination for your next vacation.brbrTropical Tranquility Meets Boating Paradise:brWake up to the gentle sounds of the water and spend your days soaking in the Florida sunshine by the heated saltwater pool with a tranquil water feature. With 125-feet of waterfront dock space, a 10,000-pound boat lift, a fish cleaning station, a 400-Pound ice machine, and a fish/bait freezer available for you to use during your stay, and easy deep-water access, this home is a fisherman’s dream. Bring your own boat or rent one locally to explore the crystal-clear waters of the Keys, go fishing right off the dock, or launch a kayak for a peaceful morning paddle.brbrOutdoor Living at Its Finest:brStep through the full glass accordion-style doors and experience seamless indoor-outdoor living. The sprawling patio and tropical landscaping provide the perfect backdrop for relaxation and entertaining. Fire up the grill in the fully equipped outdoor kitchen, dine under the stars at the outdoor dining table, or unwind in a lounge chair with the warm ocean breeze surrounding you.brbrSpacious & Elegant Interiors:brDesigned with both comfort and style in mind, this home features soaring ceilings, an open-concept layout, and expansive views throughout. The living room is warm and inviting, with plush seating, a 75-inch television, and a custom-built bar area—ideal for gathering with friends and family. The gourmet kitchen is a chef’s delight, featuring luxury Italian custom cabinetry, an induction stove, a spacious island with seating, and top-of-the-line appliances.brbrBeautifully Appointed Bedrooms for Ultimate Relaxation:br- First-Floor Primary Suite – A peaceful retreat with a king-size bed, luxurious en-suite bathroom, and private access to the pool and patio. Unwind in your spa-like bath, complete with a walk-in shower and high-end finishes.brbr- Second-Floor Primary Suite – A spacious sanctuary with a king-size bed, two walk-in closets, and a serene sitting area. The en-suite bathroom is designed for relaxation, featuring a soaking tub, separate walk-in shower, and dual vanities. This suite overlooks the patio and pool, offering a tranquil escape.brbr- Second-Floor Guest Suite – A bright and airy bedroom with twin beds that can be converted to a king-size bed, a large sitting area, a small refrigerator, and a private en-suite bathroom.brbr- First-Floor Guest Bedroom – A charming retreat with twin beds that can be converted to a king-size bed, sharing a Jack-and-Jill bathroom with the adjacent king bedroom.brbr- First-Floor King Bedroom – A stylish and comfortable space with a king-size bed, sharing the Jack-and-Jill bathroom, featuring a spacious walk-in shower and elegant finishes.brbrEach bedroom is thoughtfully designed with plush bedding, ample storage, and a private television, ensuring restful nights after a day of adventure.brbrUnparalleled Amenities:br*Heated Saltwater Pool with Water Featurebr*Fully Equipped Outdoor Kitchen with Gas Grill, Refrigerator, and Dining Areabr*Expansive 125-Foot Waterfront Dock with Deep-Water Access, 10,000-Pound Boat Lift, Fish Cleaning Station, and Space for Water Toysbr*Offers a 400-Pound Ice Machine and a Fish/Bait Freezerbr*Offers Convenient Access to Both the Gulf and the Atlantic Oceanbr*Open-Concept Living Room with 75-Inch Television and Bar Areabr*High Ceilings and Luxury Finishes Throughoutbr*Ample ParkingbrbrThe Perfect Balance – Seclusion and Convenience:brLocated in a quiet, upscale waterfront neighborhood, this home offers a sense of secluded tranquility while being just minutes from the world-class dining, live entertainment, and historic charm of Key West. Whether you're boating, fishing, paddleboarding, or simply unwinding in paradise, this luxurious retreat is the perfect place to create unforgettable memories.brbrBook your dream getaway today and experience the best of Key West living!

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$262.88

/ Nightly

Private Vacation Home

**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrThe sound of steel drums, the warm breeze off the water, the palm trees rustling in the sky… the essence of the Caribbean awaits in Key West for your next private vacation. This classic island townhome is located within Truman Annex, Key West's most exclusive gated community. From the Tommy Bahama furnishings and island inspired décor to the tropical outdoor courtyard, you’ll feel as if you’ve been transported to your own Caribbean island retreat. The location and accommodations of CARIBBEAN CHARM, coupled with Last Key Realty's unrivaled Guest Services, is certain to make your island experience one you’ll treasure forever. brbrTHE LOCATION...brbrTruman Annex is a private, gated community right in Old Town, Key West. You'll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town, yet you'll benefit from the peace and quiet that Truman Annex is known for. Although you won't need a car to get around from this excellent location, there is a reserved off-street parking space.brbrTHE COMMUNITY POOL & FORT ZACHARY TAYLOR STATE PARK...brbrThe landscaped community pool is located just around the corner and across the street, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile away from your front door.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE LIVING AREA...brbrCARIBBEAN CHARM has been furnished and decorated in a classic island style that can be found throughout the home. The living area is the entire first floor and has an open plan, with 11-foot ceilings and double French doors that provide plenty of natural light to enter. The living room features a large flat screen TV and comfortable seating options, including a plush sleeper sofa to accommodate extra guests. There's also a convenient powder room located on the first floor. The kitchen is fully equipped with all of the tools and appliances you’ll need to prepare a meal from home. The indoor dining table seats four and there’s additional seating at the kitchen bar. Enjoy an outdoor meal at your own private courtyard out front, with an outdoor dining set and a gas BBQ grill.brbrbrTHE ACCOMMODATIONS...brbr** Master Suite: Located on the Second Floor with a King bed, a large flat screen TV, a private balcony, a large closet, and an en-suite bathroom with a shower and tub combination.brbr** Second Bedroom: Located on the Third Floor with Two Twins OR One King bed, a flat screen TV, a closet, and an en-suite bathroom with a shower and tub combination.brbrEach floor closes off with its own separate door as well for extra privacy.brbrSmoking is not permitted in any Last Key Realty home. In addition, the Foundry does not permit smoking in the front garden patio areas or balconies. Therefore, this home is not a good fit for vacationers needing smoking accommodations.brbrbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped 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** Propane BBQ Grillbr** Assigned Off-street Parking for 1 CarbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** No Pets 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.

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Bath

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$757.28

/ Nightly

Apartment

Sandbar Suite | 2 bed near Duval & waterfront

Key West, Florida, United States

Summary:brbr2 bedroom, 2 bathroom retreat overlooking Front Street in downtown Key WestbrbrbrbrThe Space:brbrWelcome to the Sandbar Suite, a bright and breezy second-floor apartment perfectly situated on iconic Front Street in Old Town Key West. Just one block from Duval Street and steps from the waterfront, this inviting island retreat places you right in the center of the action — surrounded by legendary bars, live music, dining, and sunset celebrations.brbrbrbrThis is the kind of location guests dream about: walk everywhere, soak up the atmosphere, and experience Key West at its most vibrant.brbrbrbrInside, the suite offers a comfortable escape after a day (or night) out, with island-inspired décor, thoughtful amenities, and space to relax and recharge.brbrbrbr What You’ll Lovebrbr- Patio overlooking lively Front Street — ideal for people-watching, morning coffee, or sunset cocktailsbrbr- Two stylish king bedrooms with cozy bedding and a relaxed island vibebrbr- Two full bathrooms for added comfort and conveniencebrbr- Fully equipped kitchen for dining in or prepping beach-day snacksbrbr- Spacious living area with flat-screen TV, fast Wi-Fi, and central A/Cbrbr- Comfortable queen sleeper sofa in the living roombrbr- One free off-site parking space includedbrbr- One small dog welcome with manager approval and a $250 non-refundable pet feebrbrbrbrRight across the street from the Pier House and Hyatt Centric, with a small public beach just around the corner, The Sandbar Suite is an ideal home base for exploring Old Town on foot — from sunrise strolls along the harbor to late-night cocktails and live music.brbrbrbr✨ A Note About the LocationbrbrFront and nearby Duval streets are known for their lively atmosphere. You may hear music and nightlife, especially in the evenings — that's part of the authentic Old Town experience. This suite is best suited for guests who enjoy being close to the energy and excitement of Key West. Also of note, there is no parking on site but you're welcome to use our office parking lot about 3 blocks away. brbrbrbr⭐ Top-rated for location, comfort, and island charm.brbr Book The Sandbar Suite today — the heart of Key West is right outside your door.

2

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2

Bath

6

Sleeps

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