Vacation Condo Rentals By Owner In Key West, FL

$419.63

Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites!

Key West, Florida, United States

Welcome to Poseidon Too! A completely, newly renovated two bedroom two bath condo located at Sunrise Suites. Poseidon Too is located on the south side of Key West, and only about 1 mile away from Smathers Beach, and 5 miles away from downtown Duval St. Our condo is for guests that enjoy the finer things in life. The condo has just gone through a full renovation from top to bottom with only the best in mind. You will find high end furniture, a brand new kitchen/appliances, and amazing spa like bathrooms.brbrSleeping Arrangements:brMaster Bedroom - One king size bed with ensuite bath.brSecond Bedroom - One queen size bed with easy access to second bathroombrLiving Room - One queen size sleeper sofabr**All of our beds have excellent quality mattresses and come with high end bedding to give you a great nights sleep**brbrThe Space:brPoseidon Too is equipped with smart TV's in each room, high speed internet, central AC, new fully equipped kitchen with beautiful quartz countertops, new, in unit washer/dryer, and private balcony with amazing sunset views. brbrThings To Note:br- Guests will have full access to shared pool, hot tub, fitness room, tennis court.br- Sunrise Suites has elevator or stair accessbr- Parking - There are parking spaces on both sides of the building. all spaces are first come first serve. Please do not park under the building as these are reserved spots.br- Guests Access - will be contactless and you will be provided a code upon arrival.br- We can accommodate up to 6 guestsbr- Our condo is equipped with both a Keurig (with pods), and a drip pot.

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$466.94

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**SOUL OF DUVAL @ DUVAL** Modern/Centrally Located + LAST KEY SERVICES...

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThere’s no doubt you’ve heard of Duval Street; phenomenal restaurants, eclectic shops and legendary nightlife. This immaculate condo is just a half block away, giving you access to everything Duval Street has to offer while still allowing you to get a restful night’s sleep. SOUL OF DUVAL truly captures the essence of what makes Key West so special, with its playful decor, luxurious accommodations and fantastic location. Pair this with Last Key Realty’s Five Star Guest Services and your vacation in paradise will be truly unforgettable.brbrTHE LOCATION...brbrWith a prime Duval Street address, SOUL OF DUVAL is the choice location for anyone looking to have everything Key West offers at their fingertips. From the Southernmost Point and Hemingway House to famous spots like Sloppy Joe’s and Irish Kevin’s, SOUL OF DUVAL puts you in the heart of the action. Located on the ‘tamer’ 600 block of Duval, you’re within steps of Cuban Coffee Queen—a local favorite for your morning Con Leche! And with a dedicated, gated parking space, your car will be well protected while you stroll around Old Town.brbrTHE LIVING AREA...brbrSOUL OF DUVAL is the perfect place to retreat for a long weekend with a few friends. The living area is ideal for relaxing after a day full of exploration or after being out on the water. Relax in front of the large flat-screen smart TV while enjoying the comfortable seating perfect for your group. A dining table is available, along with a work space for those wishing to ‘work from paradise’. Enjoy your morning cup of coffee on the private balcony that overlooks the promenade leading to Duval.brbrTHE KITCHEN...brbrThe fully-outfitted kitchen sits off the living area with luxury appliances and tools, equipped with everything you'll need to prepare a meal at home in between enjoying the fantastic array of Old Town restaurant options, all just a few blocks walk away. Featuring both a drip coffee maker and a Keurig, not to mention Cuban Coffee Queen is right downstairs, all of your coffee needs will be well taken care of.brbrTHE ACCOMMODATIONS...brbr** Suite #1 - Queen bed, full closet and balcony access.brbr** Suite #2 - Queen bed and full closet.brbrThe shared bathroom features a full shower with a tub.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TV in Living Roombr** 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 condo also includes, but is not limited to the amenities on this list:brbr** Reserved, gated parking space for 1 vehiclebr** Balcony overlooking the pathway to DuvalbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 4 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.

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$402.75

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Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0

Key West, Florida, United States

Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include:brbr2 bedrooms 1 bath {queen and 2 twins (or we can convert the 2 twins to a king bed with a king converter) plus a sleeper sofa in the living room.brbrFully equipped kitchen with upgraded appliances and cooking accessories.brWasher & dryer with iron & ironing board.brAll towels and linens, including beach towels.brCentral air & ceiling fans.brSecond floor condo with outdoor balconies (or ask us about renting both an up and down Shipyard condo for even more room)brLarge shared Shipyard pool located just steps away.brFlat Panel TV's and entertainment center.brHigh speed internet with Wi-Fi.brAssigned parking spot for 1 car.brbrLocated in prestigious Truman Annex at Mile Marker 0 - location, location, location. Shipyard Condos are right at the entrance to Ft. Zachary Beach and next to Mallory Square and those famous nightly Sunset Festivals and just two blocks from Duval Street and all of the shops, restaurants, night clubs and museums. While we provide a parking spot, you will not need a car! brbrExcept for festivals such as Fantasy Fest, Meeting of the Minds, and Powerboat Races, we generally require Saturday-Saturday rentals so if your dates are not Saturday-Saturday please email us with your dates prior to booking so that we can check our calendar to see if an exception is possible. brbrWe have many other Key West Truman Annex vacation rental listings that can be accessed via VRBO. Let us know if you have a particular interest or property size in mind.

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$488.45

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La Brisa - Ocean Views Across from Smathers Beach

Key West, Florida, United States

Enjoy beautiful views of the Atlantic Ocean while sitting on your private porch. Located in the scenic La Brisa complex, this two bedroom condo features a large open floor plan with amazing views. Air conditioning and ceiling fans located in every room. Amenities include a pool, hot tub and tennis courts. Just a few steps across the street in Smathers Beach which offers beach chairs, umbrellas, paddle boards, kayaks and sailboats available for rent. brbrIf you are looking for entertainment- only five minutes away is Duval Street which features entertainment for all ages. Only five minutes Key West International Airport. brbrExtra features include one covered parking spot, three televisions, WiFi included, Cable TV, washer/dryer, fully equipped kitchen. brbrbrParking for two carsbrbrBecause of the beautiful property there are no trailers allowed to park. Just to unloading items

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$441.42

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Sunset Harbor - Old Town Key West Location - Beautiful Property

Key West, Florida, United States

Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located near the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, boat tours, and more.brbrProperty amenities include: onsite washer and dryers, wireless internet access, pool, hot tub, and excellent location. Take a stroll or bike ride and enjoy the Truman Annex, The harbor, Mallory Square, Duval street and much more.brbrBike rentals available just outside the property on the Harbor walkwaybr.brWelcome to the perfect location in old town Key West. Situated on the western side of the island, this property overlooks the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, boat tours, and more.brbrThis 1 Bedroom, 1 Bath Condo sleeps 4, the primary suite has a king bed and connecting bath. The unit offers a fully-equipped kitchen, dining area, seating area with TV. The living room also features a sleeper sofa.brProperty amenities include: onsite washers and dryers, wireless internet access, pool, hot tub, and excellent location. Take a stroll or bike ride and enjoy the Truman Annex, The harbor, Mallory Square, Duval street and much more.brbrBike rentals available just outside the property on the Harbor walkwaybrbrNearby attractions include Mallory Square - 4 minute walk, The Green Room - 4 minute walk, and Tree House - 5 minute walk.brbr- Parking is approximately $27 per day, or approximately $55 per week (subject to change)br- An ID and a credit card are required upon arrival for a refundable security deposit.brbr*Fees are subject to change.brbrStays of less than 1 week may require additional housekeeping for a fee.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

1

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1

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4

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$881.2

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Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 20-27, 2026

Key West, Florida, United States

This is the luxury boutique resort you and your family and friends deserve. A few steps to famous Mallory Square and all of Key West’s attractions and restaurants. Gorgeous rooms, and pools. Sleeps 6. Right on the marina with all the cool yachts! You’re going to love it! Although we can’t guarantee a water view, it is right outside your door. The resort assigns the actual unit number when you arrive depending on who has checked the week prior. You may get lucky with the view because we are owners and always request a view. Have fun it’s a blast here! Order food in or just stroll outside for hundreds of food and drink choices. There is also a full kitchen to cook or make your own cocktails!

3

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2

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6

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$437.68

/ Nightly

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Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Key West, Florida, United States

Here in Key West we believe in One Human Family where everyone is welcome and treated like family. brbrKey West! .....it’s not just a place on the map, it’s a frame of mind, an Attitude…… come and let us share that Key West Attitude with you!brbrFully Renovated This is a Luxury Executive 1 Bedroom 1 Bathroom Penthouse. brOur kitchen features high end stainless steel appliances and a Keurig Coffee station with frothier. brbrThe interior features a dedicated work station, faux shutter doors on the bedroom and bathroom for privacy, Ship lap accent walls, vaulted ceilings and nautical colors.brbrThis 1 bedroom condo is considered to be very large by Key West Standards. 2 sets of Patio Doors opening on to the Balcony that provides a peek of the ocean, King Size Bed and a Queen Size Murphy Bed, Large well equipped Kitchen.brbrOur renovated bathroom features a Couples walk in shower (the shower heads both operate at the same time or individually.)brbrWe offer:br- Dedicated work areabr- Secure High Speed Wireless internetbr - Local and long distance telephone for continental USA and Canada.br- Printerbr- 2 Adult bicycles (The Best Way to Explore our little Island) br_ 2 Comfy chairs on the balconybr- Central A/Cbr- High quality Bedding and Linens. br- Stainless Steel appliances. br- Full size Washer and Dryer br- 2 Large Smart TV's ( Living area and Bedroom)br- HD Cable br - Assigned garage parking for 1 vehicle (Oversized vehicles and Golf Carts have to park outside)br- Poolbr- Hot tub br- Gym br- Sauna br- Private natural beach area br- Picnic/Grilling areabr- Tennis courts ( 1 clay court and 2 regular) br- Laid back Costal Decorbr- Stunning Courtyard with lots of little surprises, here you will see that Orchids do grow on trees! This is our little piece of Paradise!brbrIt should be noted that NOT everyone here is on vacation there are many full time residents so it is important to be considerate and respectful understanding that not everyone is in vacation mode. If you are looking for something a little wild this may not be the space for you.

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$507.2

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Oceanfront Marina Condo With All Luxuries

Key West, Florida, United States

Your spacious oceanfront balcony will be a front row seat for a panorama of azure blue ocean and sky. There are touches of tropical whimsy everywhere, like the “Windblown Table Lamp” in the reading alcove, a quirky reminder that you have arrived in America's Tropical Paradise. And since you are in the tropics, it goes without saying that there are overhead fans in every room.brbrThe living area is bright and airy, with plenty of room for everyone to stretch out and relax. There's a large high definition flat screen TV with expanded cable service. Large sliding glass doors open onto that spacious ocean view balcony. The kitchen is completely equipped and newly renovated with brand new appliances and everything else you would need to prepare the most ambitious meal. The master bedroom has a queen size bed, walk-in closet and also has sliding glass doors to the balcony. The en-suite bathroom has twin vanities and a separate “water closet” for the toilet and oversize glass shower. The second bedroom has twin beds that convert to a king. The third bedroom has a queen bed. If desired, the second and third bedrooms become one spacious suite. The second bathroom has an extra large shower. 28 night Minimum Stay Please Inquire.brbrA POOL & JACUZZI RIGHT ON THE OCEAN...brbrThe large community pool and Jacuzzi are situated right on the oceanfront; you'll have those cooling ocean breezes all the time. There are a generous number of chaises and tables with umbrellas, and gas grills for those BBQ parties on the pool. If you have brought your own boat, you'll be able to keep it at one the many dry slips or wet slips available. Stand Up Paddleboard, Kayak, Jetski rentals are available. Contact the Dockmaster @ 305-360-2909.brThe Yellowfin bar and restaurant is across the parking lot.br28Day Min. Rental

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$190.13

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STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

Key West, Florida, United States

STEPS TO DUVAL! WALK EVERYWHERE-- ALL THE SHOPS, RESTAURANTS AND BARS OF OLD TOWN! You wont need a car with this location. You can walk, bicycle, rent a scooter or golf cart to get around.brbrLA DOLCE VITA is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Historic District!! brbrSouthernmost Point and Southernmost Beach on the Atlantic Ocean are just 3 short blocks away! Southernmost Cafe also has a great Happy Hour!brAlso, one of our favorite spots is the Seaside Cafe which is on the water and has great drinks, pizza, salads. It is located next to Southernmost Cafe. brbrPlease check out our calendar for availability and our photos and video. brbr The condo is on the second floor of an old, beautiful, Key West style building with a wraparound balcony.br It has high 14 ft ceilings, a granite galley style kitchen, stainless steel appliances, refrigerator, freezer, ice maker, 2 burner glass cook top and microwave . It has cherry wood laminate floors, queen size bed w/ memory foam mattress, 75 inch flat screen Smart TV in living room, 35' Roku TV in bedroom, ceiling fans in living room and bedroom, full bathroom, crown molding throughout with recessed lighting on dimmer switches and also rope lighting on the ceiling throughout the condo for a cozy, relaxing feel. brbr The condo has a shared porch with 2 sitting chairs on a large wrap around balcony. brbrThere is a public pool at 300 Catherine St. one block away. It is the Community Center and has picnic tables, basketball courts and playground. Weekend hours vary. Their phone number is 305-809-3876. brbrDante's Pool & Raw Bar is located at 951 Caroline St, which has a large pool, full bar, Tiki bar and grill. It is a short bike ride away. Pets are welcome.brbrJust 3 short blocks away is Southernmost Beach which has Southernmost Cafe and offers breakfast, lunch, dinner and happy hour. brbrThree blocks to Southernmost Point on the Atlantic Ocean. Also, a few blocks away is Fort Zachary Taylor Beach which is a 20 minute walk. Fort Zachary Taylor Beach is Key West's most beautiful beach!brbrYou will not need a car with this location! Walk to all the shops, restaurants, bars and beaches of Old Town, Key West! brbrIf you would like to purchase any of the artwork in the condo, please inquire. Thanks! :)

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$350.36

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Galleon Resort efficiency

Key West, Florida, United States

This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, toaster, coffee maker. Perfect for a quick getaway, to enjoy the beautiful sunsets of Key West. The Galleon Resort is steps away from the famous Duval Street. Sunset tiki bar and Pirates Cove on premises. 3 blocks from Mallory Square and the beginning of “ Harbor Walk”. Scooter, bicycle, jet skis and boat rentals available on site. No need for a car once here.

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$973.13

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SEAPORT PANORAMA at Galleon Resort-Beach-Pool-King-BBQ-Kitchen views!

Key West, Florida, United States

GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY VIEWS OF KEY WEST HARBOR, SUNSET KEY AND THE GULF OF MEXICO. (These views are also available from the master bedroom, living area and kitchen all day, every day)brbr4th FLOOR OCEANFRONT CONDO RENTALbrSleeps 6 / 1 Master King - 1 Guest Queen / 1 Queen pullout / Large private oceanfront balconybrbrEXCEPTIONAL LOCATION & CONVENIENCEbrThe Galleon Resort is located at the end of North Front St (literally steps from your elevator to Seaport Boardwalk happy hour bar menus, shops & multiple restaurants) / 2 blocks to Duval St + more restaurants, Mallory Square, Front Street eateries, bars and shopping—or cook steaks & seafood on our newly renovated paver picnic patio with 2 extra large Pro BBQ grills and free propane gas on demand + 3 round umbrella picnic tables / 3 HD cable TVs in condo / Free wireless internet / Free private parking / Secluded but very close to all the action / Car not necessary / Rental scooters, bikes, electric golf carts, fishing tour boats, wave runners all on-site to explore Key West from land or water / Oceanfront Tiki Bar & Pirates Cove Marina Bar & Grill on premisesbrbrRECOGNIZED & VOTED IN 2016-17-18 AS A TOP-25 TIMESHARE RENTAL RESORT BY TIMESHARE USERS WORLDWIDEbrbrBEAUTIFULLY LANDSCAPED OCEANFRONT SWIMMING POOL & HOT TUB, LARGE NEW OCEANFRONT COVERED TIKI BAR, NEW SUN DECKS & GAZEBOS, SMALL PRIVATE BEACH & OCEAN SWIM AREA w PLATFORM, PRIVATE FISHING PIER & NEW BBQ PATIObrbrFull-service resort with on-premises concierge, housekeeping, maintenance and security staffing with computerized door entry cards, security cameras, and room safes for guests.brbrChildren welcome. Suitable for seniors and handicapped with four elevators, ramps to pool, outdoor hot-tub, beach, Granite sitting ledges in Master Bathroom and open entry from walk-in shower to JacuzzibrbrThis 96-unit oceanfront property is accessible by car or boat, with free parking and rented boat slips / Great for families & sailboat crews / Marina next to resort to dock your boat / Full laundry, sauna / At the entrance to the Historic Seaport boardwalk / On the ocean in the heart of Key West's incomparable Old Town w tin-roof conch houses, historic museums & homes, unique shops, artist galleries, and quirky Duval Street entertainment / *Don't miss the nightly, world-famous Mallory Square Sunset Celebration (Unique Entertainment-Food-Art-Crafts) just 2 blocks from your condobrbrTHIS CONDO has a full size, fully equipped kitchen, breakfast area, wet bar w wine storage, washer-dryer, dining area, living room with entertainment center (55” TV, DVD player, AM-FM stereo, extra wardrobe closet, drawers) in living area, master bedroom with ensuite 2-sink vanity, closet, makeup vanity with extra device outlets, shower w attachments & jet-tub Jacuzzi, guest bedroom with full bathroombrbrFULL BALCONY with lighting has four chairs & table, and is accessible thru French doors in both the living room and master bedroom with sweeping front and corner views of Key West Harbor, Sunset Key and Gulf of Mexico.brbrEXTRA AMENITIES include 3 HD TVs with cable, DVD player, AM-FM stereo, iron & ironing board, jacuzzi tub, in-room safe and free private/secured wireless internet / Pool towels & bed linens provided / Kitchen and Master bath received complete granite & appliance renovation with new living room furniture in last 2-3 years / There is 1 free parking space for each unitbrbrQuiet and secluded, yet very close to restaurants & shopping / On-premises large oceanfront swimming pool with jetted hot tub / New oceanfront decking, lounges and umbrellas surround the resort / On-premises oceanfront TIKI BAR and Marina-side PIRATES COVE breakfast & lunch bar-grill / On-premises GIFT SHOP with unique, hand-painted & personalized souvenirs at driveway entrance / Small private beach with private fishing pier / New picnic patio with new extra large Pro BBQ grills and umbrella picnic tables / Roof-top observation deck provides amazing 360 degree views of Key West

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$298.98

/ Nightly

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Beachy Keen Too at Beach Club in Key West WEEKLY RENTAL

Key West, Florida, United States

WEEKLY RENTAL - Enjoy endless open water views just footsteps away from the tranquil waters and beach of the Atlantic Ocean. br“Beach Club #304” is a serene waterfront oasis located in an upscale gated community within walking and biking distance to the local’s finest spots, including restaurants, beaches, shopping centers, bars and the infamous Duval Street. brbrThe Living room is brightly decorated with spectacular views of the Atlantic Ocean and a wonderful walk out covered dining and lounging deck. The breathtaking view can be seen as soon as you enter this spacious 2-bedroom coastal retreat, which includes combination dining room and comfortable seating for those spontaneous movie nights. The kitchen is fully equipped to make that perfect home cooked meal. brbrBedroomsbrPrimary 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 and covered dining facilities, and fitness center. Immediate beach and open water access. There are plenty chaise lounges around both pool areas as well as a cabana to enjoy during those sunny island afternoons. Additionally, Rest Beach, Higgs Beach and Smather's Beach are conveniently located nearby.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 rental agreement.brbrThis property will accommodate up to 4 adults comfortably, there is an additional sleeper sofa for everyone to spread out:)brSorry, pets are not allowed

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Bath

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$699.75

/ Nightly

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Near Duval - Tiki Bar - Private Beach - 2BR Condo - Old Town Key West - Sleeps 6

Key West, Florida, United States

Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the jacuzzi or sauna during your stay or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.brbrThis spacious two bedroom condo sleeps six, and features a fully equipped kitchen, including a full-sized refrigerator, microwave, toaster, coffee maker, stove and oven. The primary bedroom has a king sized bed, ensuite jetted tub, as well as a full bathroom. The guest bedroom layout may vary, featuring either two twin beds or a queen bed, and has access to the full guest bathroom. Please let us know your preference before booking and we will do our best to fulfill it, though it is not a guarantee. The living room has a TV with cable, dining area for four, and a sleeper sofa. Off the living room is a balcony to enjoy the Key West ocean breezes.brbrGalleon Resort Marina serves breakfast. Guests can enjoy poolside drinks at Sunset Tiki Bar.brbrKey West Shipwreck Museum and Mallory Square are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum is 1 mile away.brbrPlease note, guest bedroom may feature two twin beds or one queen bed. Please let us know your preference before booking. We will do our best to fulfill it, but it is not guaranteed.brbrResort fee in the amount of ($20/per day or $75/per week) plus tax, due at check-in, along with a $150 refundable security deposit. Refundable security deposit is released, as long as no damages occur during your stay. (subject to change)brbrUnits are assigned after booking, in seven night increments. Multiple week stays may be booked, room moves may be required.brbrHousekeeping changes linens and towels on Tuesday only. If daily housekeeping is desired, there is an additional fee imposed by the resort.brbrParking for one vehicle, per unit only. No oversized vehicles, RV's or trailers are allowed to park on property. Parking is extremely limited and multiple vehicles are not able to be accommodated.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

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Sleeps

$395.44

/ Nightly

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The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6

Key West, Florida, United States

This deluxe Key West Charmer is a beautifully restored Victorian home built in the 1880's that was converted into individual condominiums many years ago, located just one block from Duval Street in the Heart of Old Town Key West. Our casual atmosphere allows you to chill out and enjoy having the best of Key West within easy walking distance of all the restaurants, bars, entertainment and museums that we are most famous for.brbrMingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon. Enjoy alfresco dining in the tropical gardens while you enjoy the wonderful weather that Key West offers!! brbrThe Carriage House building at the Hollinsed House 2nd Floor - Caribbean Suite is a tropical 2BR/1BA with king beds, full kitchen, living room (with futon), dining area; two balconies with one stretching across the front overlooking the pool and garden area and one located off a bedroom. Sleeps 4 - 6.brbrHave a group coming to Key West Or maybe need just one or two more units Go to Click Here to see All My Rental Listings just above the Map Feature to see the rest of my listings at the Hollinsed House!brbrRATES for SPECIAL EVENTS:brPlease note that rates for Fantasy Fest, Meeting of the Minds (formerly Jimmy Buffet Parrothead Days), Race Week, Thanksgiving, Christmas, New Years, Songwriter's Festival, Memorial Day Weekend, Hemingway Days, and Poker Run all have minimum stays and different rates than are listed on the Rates page of this VRBO listing. brbrDEPOSITS:brA deposit equal to the cost of one half of your stay or one night, whichever is greater, is required to guarantee a reservation. The balance is due 30 days prior to arrival. Sorry, no refunds for early departures. brbrCANCELLATION AND REFUNDS:brCancellations from time of booking to thirty (30) days of arrival date will be charged a $50.00 processing fee per unit rented. All bookings of one week or longer will be charged a $100.00 processing fee per unit rented if cancelled more than thirty (30) days prior to arrival. Cancellations within thirty (30) days of arrival date will be charged for one night per unit rented or may extend their reservation for six months. Cancellations within seventy-two (72) hours to twenty-four (24) hours have a 50% cancellation fee or can be extended for six months. Cancellations within twenty-four (24) hours are non-refundable but will be offered a six-month extension. Sorry, no refunds for shortened stays. We reserve the right, to change your unit number if you are reserving for 3 nights or less.brbrCancellations for Special Events: Fantasy Fest and Christmas/New Years. Reservations of 5 days or longer that are cancelled within 2 weeks of arrival will be charged a $250 cancellation fee. Reservations cancelled within 1 week of arrival will be charged a $500 cancellation fee. Reservations cancelled within 72 hours of arrival are non-refundable. All cancelled reservations will be offered a six-month extension.brbrHURRICANE SEASON CANCELLATION POLICY, EFFECTIVE JUNE 1 -DECEMBER 15TH:brWe do not refund for inclement weather or other circumstances beyond our control. We strongly encourage the purchase of Travel Insurance to protect your vacation investment! In the unlikely event that a hurricane evacuation is ordered while you are a guest, and you have not purchased travel insurance, you will be issued a voucher for the unused portion of your stay. Guests holding a confirmed reservation who are unable to travel to The Hollinsed House because of the closing of the Key West Airport or connecting roadways due to a mandatory evacuation and have not purchased travel insurance will receive a voucher in the amount of the room deposit held. Vouchers are redeemable between June 1 and December 15, up to one year from the issue date, excluding special events and holidays. (Exception: Vouchers issued for cancellations of Fantasy Fest reservations can be applied to future Fantasy Fests in the ensuing two years.) No voucher will be issued if the hurricane is not a threat to Key West and you are unable to travel because of canceled flights or adverse travel conditions outside the Keys. We strongly encourage the purchase of Travel Insurance to protect your vacation investment!brbrKeywords: Guest House, Condo, B&B

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$434.62

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Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!

Key West, Florida, United States

This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting experience. The location is highlighted as a key factor, emphasizing the significance of its surroundings.brbrAs you enter Caroline on My Mind, you'll notice a stairway adorned with wainscoting, leading you to the entry. The home boasts an open and comfortable living area, allowing ample natural light to fill the space. The living room features high-vaulted ceilings and cathedral windows, creating an instant vacation-like ambiance.brbrThere is a flat-top electric stove, two-door refrigerator, and dishwasher available to facilitate your cooking needs. The countertop seating for three also provides a convenient space for dining or socializing while in the kitchen. Overall, the kitchen offers functionality and amenities that will allow you to enjoy preparing meals during your stay.brbrThe guest room is located on the same floor, accompanied by a full shower bathroom and a washer/dryer for added convenience.brbrOne of the standout features of this home is the large balcony that overlooks Caroline Street below. Equipped with fans, the balcony serves as a perfect spot for savoring morning coffee or enjoying cocktails. A four-person table allows for al fresco dining, while you can also engage in people-watching and relish the refreshing evening breezes of Key West.brbrTo access the floor above, a spiral staircase takes you to the treetops, providing a unique vantage point. The primary bedroom on this floor features a queen-sized bed that can be converted into two twins upon request. Additionally, for those who need to work while in paradise, there is a functional desk with great views, enabling mental breaks amidst the scenic surroundings.brbrLastly, there's a skylight in the primary bedroom, offering the opportunity for star gazing while lying in bed at night, adding to the enchanting atmosphere of this Key West home.brbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. brbrMonthly Rental OnlybrbrShared Pool/6 unitsbrbrPets Not AllowedbrVirtual Tour Url: https://my.matterport.com/show/ m=TXf1ngy4X89

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$806.58

/ Nightly

Condo

Heart of Key West - 2BR Waterfront at the Galleon Resort

Key West, Florida, United States

Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the jacuzzi or sauna during your stay or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.brbrKey West Shipwreck Museum and Mallory Square are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum is 1 mile away.br.brWelcome to the heart of Old Town Key West. The resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, restaurant and tiki bar. This two bedroom condo sleeps six, and features a fully equipped kitchen. The primary bedroom has a king size bed, jetted tub, as well as a full bathroom. The guest bedroom features either two twin beds or one queen, and has access to the full guest bathroom. The living room has a TV with cable, dining area for six, and a sleeper sofa. Off the living room is a balcony to enjoy the Key West ocean breezes. brbrResort fee is due at check-in, along with a refundable security deposit. Refundable security deposit is released, as long as no damages occur during your stay.brbrPlease note, guest bedroom may feature 2 twin beds or 1 queen bed. Please let us know your preference before booking. We will do our best to fulfill it, but it is not guaranteed.brbrUnits are assigned after booking, in seven night increments. Multiple week stays may be booked, room moves may be required.brbrHousekeeping changes linens and towels on Wednesday only. If daily housekeeping is desired, there is an additional fee imposed by the resort.brbrParking for one vehicle, per unit only. No oversized vehicles, RV's or trailers are allowed to park on property. Parking is extremely limited and multiple vehicles are not able to be accommodated.brbrMinimum Age: 25 years oldbrPet Policy: No PetsbrAn ID and credit card for a refundable security deposit will be required.brCheck-in is after 4 pm; brCheck-out by 10 am.brNo Smoking. Penalties will apply.brNon-Refundable Cancellation and Refund PolicybrbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.brbrPictures are representative of the unit, layout and decor may vary. Units assigned at time of booking, please inquire prior to booking about specific unit and bedding configurations. All units have a King Bed in the master bedroom and the second bedroom will either have two twin beds or one queen bed.brbrUnits are assigned in 7 night increments, multiple week stays may be booked, room moves may be required.

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$163.06

/ Nightly

Condo

Villa Nomade at Shipyard Condominiums

Key West, Florida, United States

Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. The living room is furnished with comfy furniture and a 50TV. The bedrooms have queen beds. Enjoy outdoor dining on the deck surrounded by a tropical landscape. brVilla Nomade is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former U.S. Navy property of Truman's Little White house. Just steps from Duval St. and located near the Ft. Zach beach and Hemingway's house, all of Old Key West's sites are within easy walking distance. Our private oasis can be your tropical retreat.

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$381.07

/ Nightly

Condo

Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West

Key West, Florida, United States

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom Villa Porta is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. Please email us even if the availability calendar looks full.brbrThe number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West. br1/2 block to Hard Rock Cafebr2 blocks to Margaritavillebr2 blocks to Sloppy Joe’sbr3 blocks to the Historic Seaportbr4 blocks to Mallory Squarebr4.5 blocks to Schooner Wharfbr6 blocks to Hemingway’s HousebrbrPlease be aware of scams asking for wire transfers or offers from Craigslist. If you have any questions, please call our reservations desk.

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$593.22

/ Nightly

Condo

By the Beautiful Sea - Key West Beach Front Condo - w Pool Access

Key West, Florida, United States

bPLEASE NOTE THE POOL AND JACUZZI WILL BE CLOSED FOR RENOVATIONS FROM JULY 6, 2026 TO AUGUST 30, 2026/bbrbrIf you`re craving a Key West beach front accommodation with a bone fide front-line view to the sea, you know that Key West beach front rentals not easy to come by. But in this pretty vacation rental condominium, By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace right across the street from the beach. Make your first order of the day to breathe in the fresh ocean breezes with a walk along the beach and fulfill the desire to dig those toes into warm white sand . . . for after all your front yard isKey West by the sea on the the Atlantic Ocean side of the island. Your `back yard` view is not bad either. The entrance for this property connects with a second level walkway of the building, and offers views of beautiful tropical park-like landscaping. A short stroll from the condominium through the landscaped setting, leads to the large free form swimming pool and Jacuzzi. A major decision each day could be whether to enjoy the sun at the beach or pool side. And when it`s time to go dining, shopping, or enjoying the nightlife, Old Town is close by and an easy bike ride away. Ahhhh . . . life in paradise is good.brbrThe interior layout of this property was designed to maximize the opportunity to take in the ocean view from the living room and dining area, as well as the master bedroom. Sliding glass doors off the living room, lead to a private ocean view terrace. The kitchen adjoins the dining room through a pass through door, creating a floor plan that makes it easy for entertaining the family or a group of friends.brbrThe layout of the bedrooms is ideal for a family or three couples. You`ll need to flip a coin for the enviable master suite that has the ocean view, plus a door that leads directly to the sea-side balcony. Furnishings are tropical elegant with a honey-colored wood-and-wicker king size bed and romantic free-standing grandfather clock to remind you that it`s 5 o`clock somewhere. Another nice feature of the master bedroom is a walk-in closet. Next to this closet, the master bath provides a long vanity with two sinks, tiled floor, and bath-tub with in-tub shower.brbrThe other two bedrooms and second bathroom, are on the opposite side of the condominium, down a short hallway, just off the great-room. Immediately off the hall to the right is a bedroom with two twin beds, which can be made up as a king size bed upon request. Nicely decorated with white cottage furnishings, there is also plenty of daylight that streams in through a nice size window. Directly at the end of the hallway is the third bedroom with king size bed. Handsome honey-colored wooden furnishings fill the room in nice contrast with the coral colored walls. A window on one wall invites in the natural light.brbrThe second full bathroom, with standing shower and glass door, is situated off the hallway, easily accessed by both the second and third bedrooms. This bathroom also conveniently houses the washer/dryer, a welcome feature for a beach house, where you can come in and drop your towels and wet bathing suits.brbrA notable layout feature of this property is that it`s an end unit in the condominium building, making it one of the more desirable locations in the complex as you only have neighbors on one side. It is located on the first floor, but elevated second level, since the covered parking is directly below. This design provides a wonderful view of the ocean, the perfect Key West by the sea experience. The entrance to the unit can be reached by stairs or elevator. There is designated covered parking, and the condominium complex is gated and secured with an electronic key entrance.brbrBedding Summary:brbrMaster Bedroom 1 – King size bedbrbrBedroom 2 – 2 Twin Beds (can be made as a king size bed)brbrBedroom 3 – King size bedbrbrbrAmenities: Located in a beach condominium complex across the street from Key West Smathers` Beach. Private balcony with front-line view to the sea. Balcony access from great-room and master suite. Resort style heated swimming pool, hot tub, separate men and women saunas and changing rooms near pool for guest use only. Tennis courts, propane BBQ grills on the grounds. Fully equipped kitchen, central A/C, Wi-Fi, cable TV and DVD, stereo, washer / dryer. Linens and towels are provided.brbrActivities: This property is Key West by the sea! Everything beach! Sunning, swimming, catamaran rentals, volleyball, beach food trucks. Easy walk to the White Street Pier, Salute Restaurant for dining on the beach, ocean front children`s playground, historic garden club, nature preserve, much more. A bike / walking path winds along the ocean and leads you to the heart of Old Town Key West where you find restaurants, nightlife, museums, everything Key West has to offer.brbrArea: This area of Key West is often referred to as the beachside neighborhood due to the close proximity to the southern shore of the island. This part of the island feels like a beach town neighborhood with light ocean breezes, and it`s not unusual to see folks walking or biking on the bike path in their bathing suits with towel and cooler under arm. A paved biking and walking path stretches along the southern shore dotted with parks and food and water sport concessions making it easy and interesting to stroll or bike. There is a pre-Civil War Fort along the waterfront, West Martello near Higgs Beach that now houses the Key West Garden Club.brbrParking: Designated covered parking for one vehicle. One additional vehicle may park in the adjoining lot. All vehicles parked must display parking passes issued by the condominium. Scooter parking allowed. Bicycle racks near elevator. No boats, RV`s, Jet ski`s or trailers of any kind are allowed in the parking area.brbrRestrictions: No smoking. This condominium is offered as a vacation rental in a preferred beachfront condominium in Key West. Pets are not allowed. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. No boat, trailer (bike or boat), jet ski, or RV parking. Guests must agree to abide by condominium regulations.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.brThere is designated parking for one (1) car at ‘By The Beautiful Sea.’ Drive in the gate and turn left. See the second parking space under the building marked #2. This is your parking space. You are also allowed 1 additional parking space anywhere in the general parking area.

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$262.56

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Condo

Summer Breeze: Spectacular View, the Beach, Pool and all the Amenities. 2BR/2BA

Key West, Florida, United States

*BRAND NEW LISTING* 28 Day Minimum!!! 'Summer Breeze' will make you and your family feel fine! This is a gorgeous, clean, upgraded, top floor, 2/2 condo, sleeps 4, with a spectacular view! Common pool, grill area, tennis court and a nice friendly atmosphere will make you and your family happy to have chosen this great property. Smathers Beach is across the street, Higgs Beach is a short walk, Duval Street a short bike ride or walk. Literally anything on the island is within your reach! 28 day minimum stay - set up for 4 adults only. Bring your bikes or rent them here and be anywhere in Key West within minutes! Maybe you want to rent a golf cart and do the same!

2

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2

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6

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