Vacation Rentals By Owner In Key West, FL

Experience the best of Key West from your own private houseboat docked at The Perry Hotel & Marina. Enjoy stunning waterfront views, cozy interiors, and full access to hotel amenities including two pools, on-site restaurants, a fitness center, and a free shuttle to downtown. Relax on the deck, explore the island, and unwind in style. Perfect for a romantic getaway or unique island escape—this is Key West like you’ve never experienced it.

House Boat

Docked in Paradise

Key West, Florida, United States

Bed

Bath

Sleeps

$239.19

The Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West. So, get out there and live it up in Key West and come home to a king size bed and everthing you need to fix your own cocktails.brbrLocated in a 6 unit compound this tiny Association is located in the heart of Old Town on Simonton St. Walk to the Hemmingway House, the Butterfly Conservatory and stroll Duval street with it's shops, restaurants, galleries and museums. brbrPeople ask me about parking more than anything and this condo does not come with assigned parking but the spaces in our block, on the street out front available on a first come basis. I provide additional tips for finding parking with my instructions but I encourage you to not bring a car into Old Town as it is an historic district and over 100 years ago it was not anticipated that tens of thousands of visitors would come to enjoy it's beauty so there simply is not enough parking in Old Town for all who come and changing that would affect the historical value. A car is not a practical way to tour Old Town because parking is scarce and expensive all over town. Locals have adapted and have taken to bicycles to travel the Town. The City of Key West has implemented a bus service around Old Town called the Duval Loop and it stops a half block from this rental. brbrShould you book this property I strongly recommend you purchase the cancellation insurance offered by VRBO, particularly during hurricane season. Flights are frequently canceled by the airlines and while they may be willing to rebook new flights I do not have the flexibility to give you new dates and you will be expected to pay for the dates you booked. Cancellation insurance will cover this in most cases. brbrThere is no pool at this property but there are small beaches all around the island and several are within walking distance of this property; Southernmost Beach would be closest at 6 blocks away. Fort Zachary Taylor State Park has the beach that locals like best, it is a State Park so there is a fee but the facilities are excellent: picnic tables, grills, outdoor shower, indoor shower, change rooms, restaurant, chaise lounges for rent and a water view that is the best in Key West. brIf you prefer a pool there is an excellent public pool at 300 Catherine St. The MLK Community Pool is an 11 minute walk from the condo and this roof-top, outdoor pool offers excellent sunbathing and views of Key West. brThere are also hotels that welcome patrons of their restauant to use their pools and I provide info on those locations in the condo. brbrThank you,brPam MacKenzie

Apartment

Simonton Studio, an Old Town get-away for 2

Key West, Florida, United States

Bed

Bath

Sleeps

$450.01

DETAILS AND AMENITIES...brEnter this inviting open floor plan with incredible natural lighting throughout. Three sets of French doors take you from the living/kitchen space out to the outdoor entertainment area, consisting of a private heated lap pool all to yourself, propane gas grill, swing set, outdoor dining for 4, additional outdoor seating and pool loungers. Wood flooring, high ceilings and breezy ceiling fans in each room will keep you cool and refreshed on a sultry summer's day. Whip up your favorite family meals together in the gourmet kitchen that comes with gorgeous granite countertops, custom cabinetry, updated stainless steel appliances and dining for 6. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrSLEEPING ARRANGEMENTS...brThe downstairs guest room comes with a queen size bed and a private porch. There is a full bathroom just outside of this bedroom with a walk in shower. Upstairs you will find the king master bedroom with an en suite full bathroom that comes with a desirable claw tub, walk in glass shower and washer/dryer set. Adjacent to the master bedroom is an enclosed, air-conditioned Florida room with cozy seating which then leads you out to an additional outdoor, covered balcony with incredible views of the lush tropical pool area. Steps down the hall is another guest room with a queen size bed, an en suite full bathroom with a shower/tub combination and a private, covered balcony area. The colorful, teal-tiled poolside cottage comes with a queen size bed and an en suite full bath with a shower/tub combination, and it is air-conditioned. All bedrooms are equipped with a flat screen TV and ample closet space including the guest cottage.brbrOUTDOOR LIVING...brCool your senses and quench your island craving with this magnificent outdoor space that offers your own exceptional private poolside lounging space. THIS POOL IS ALL YOURS--YOU DO NOT SHARE IT WITH ANYONE ELSE! Take advantage of the additional outdoor dining space for being able to enjoy your fresh catch of the day in the evening hours followed by swimming under the stars. This community’s quaint pathways are just a few steps away from all the island's main attractions. brbrPARKING...brThis home comes with one covered parking space. No trailers, boats, jet skis or motor homes are allowed. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property. Additional vehicles may park in the Opal Key Resort parking garage just a five minute walk/drive away.brbrPETS...brPets are permitted with a required pet fee. Please provide pet size, breed and age upon booking. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool Heat 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. Cancellations 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.

BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!

Key West, Florida, United States

Bed

Bath

8

Sleeps

$1451.13

Welcome to Bottom’s Up Bungalow — Your Private Tropical Escape in Old Town Key WestbrbrStep into a world of comfort and island charm at Bottom’s Up Bungalow, perfectly situated in the serene Meadows subdivision, just minutes from the vibrant heart of Key West. This immaculate 2-bedroom, 2-bathroom single-family home combines classic Florida bungalow appeal with modern amenities to create an inviting retreat that has earned over 100 glowing five-star reviews from delighted guests.brbrHome Highlights & FeaturesbrbrSpacious & Inviting Living RoombrBright and airy, the living room is designed for relaxation and socializing. Sink into the plush sectional sofa that easily converts into a sleeper for additional guests, or unwind in the comfortable sitting chair while enjoying your favorite shows on the large flatscreen TV. Natural light floods the room through large windows, creating a warm and welcoming atmosphere.brbrElegant Formal DiningbrJust off the living room, the formal dining area comfortably seats four — perfect for intimate dinners or leisurely breakfasts. The classic design complements the polished hardwood floors that flow throughout the home.brbrChef’s Dream KitchenbrThe heart of the home is a spacious, open-concept kitchen featuring generous counter space, high-quality appliances, and all the essential cookware and utensils to prepare anything from casual snacks to gourmet meals. A breakfast bar with stools offers a casual dining option, while the adjacent informal dining nook provides a cozy spot for family meals. Double French doors open onto the poolside patio, inviting fresh air and natural beauty inside.brbrTranquil Primary SuitebrThe primary bedroom is a serene sanctuary, outfitted with a luxurious king-size bed, a sturdy chest of drawers, and a large closet with a full-size washer and dryer tucked inside for your convenience. Step through elegant French doors to the pool and garden, perfect for early morning coffee or evening relaxation under the stars.brbrSpa-Like Primary BathroombrLocated just outside the primary suite, the hallway bathroom boasts a spacious custom shower with sleek tilework, a large vanity with ample storage, and a linen closet to keep all your essentials neatly organized.brbrFlexible Guest BedroombrThe second bedroom features two twin beds that can easily be converted into a king bed upon request, ideal for couples or friends traveling together. This room also includes a chest of drawers, a roomy closet, and a private en-suite bathroom complete with a shower, vanity, and toilet — providing comfort and privacy for your guests.brbrResort-Style Pool & Outdoor LivingbrStep outside to your private tropical paradise. The oversized pool, heated from December through May, is perfect for a refreshing swim any time of year. The attached whirlpool spa (note: not a hot tub) offers soothing bubbles to relax tired muscles. Surrounding the pool is an elevated deck with two sun loungers — ideal for soaking up the Florida sun. Enjoy meals or drinks at the outdoor dining table shaded by an umbrella, or retreat to the custom-built gazebo featuring a wet bar and bespoke seating, making it the ultimate space for entertaining or unwinding.brbrLush Tropical Gardens & PrivacybrThe beautifully landscaped gardens are enhanced by tasteful lighting and privacy fencing, creating a secluded oasis that feels worlds away from the bustle of downtown Key West. The tranquil greenery invites you to savor quiet moments with family and friends in any season.brbrParking & ConveniencebrOne assigned parking space is available in the driveway for your ease and security. Additional vehicles can be parked roadside, subject to availability, allowing you to bring along extra guests or rental cars with peace of mind.brbrPrime Location Near the Best of Key WestbrTucked away on a quiet one-way street within a peaceful community, Bottom’s Up Bungalow offers the perfect balance of tranquility and accessibility. You’re less than one mile from the excitement of Duval Street, famous beaches, and the marina. Enjoy the vibrant nightlife, eclectic dining, and unique shops of Old Town, then retreat to your calm, private sanctuary at day’s end.brbrWhy Choose Bottom’s Up Bungalow brbrWhether you’re here for a romantic getaway, a family vacation, or a fun trip with friends, Bottom’s Up Bungalow provides the perfect home base. With its spacious layout, thoughtful amenities, lush outdoor spaces, and unbeatable location, this bungalow promises a memorable Key West experience filled with relaxation, adventure, and island charm.brbrWe invite you to be our guest and experience the magic of Bottom’s Up Bungalow on your next trip to Key West!

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

Key West, Florida, United States

Bed

Bath

Sleeps

$326.31

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

Villa Fleur at Shipyard Condominiums

Key West, Florida, United States

Bed

Bath

Sleeps

$354.91

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

$306.97

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

Your Condo by the Beach with Ocean View

Key West, Florida, United States

Bed

Bath

Sleeps

$851.89

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

$605.77

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

Peaceful Setting Amongst The Active Island Life Style

Key West, Florida, United States

Bed

Bath

Sleeps

$379.51

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbr73 PALMS is a beautifully renovated two-story home offering the perfect blend of luxury, comfort, and island charm. As its name suggests, the property boasts a remarkable 73 swaying palm trees, creating an unparalleled tropical ambiance that immediately transports you to paradise. This meticulously designed 3 bedroom home features a large swimming pool and plenty of off-street parking. Situated in Midtown, 73 PALMS is a short walk or bike ride from the lively attractions of Old Town, the beautiful Atlantic beaches, and a variety of dining and shopping options, while still enjoying the peaceful residential atmosphere of Midtown. Best of all, a month at 73 PALMS includes Last Key Realty’s renowned Guest Services & In-house Concierge, ensuring your Key West vacation will be one you’ll cherish for a lifetime. brbrTHE LIVING AREA & KITCHEN…brbrThe open concept living area on the first floor is bright and airy, decorated with a relaxed coastal aesthetic. The comfortable living room invites relaxation on the plush sectional sofa that sits in front of a large flat screen TV. The fully equipped kitchen with modern appliances makes meal preparation a breeze. The interior dining table seats six comfortably, and a convenient half-bath on this level adds to the practicality.brbrTHE BACKYARD & POOL…brbrThe true highlight of 73 PALMS is its expansive outdoor living space. Step outside to discover a sprawling private oasis centered around the large, inviting swimming pool. Imagine spending your days soaking up the sun in the chaise loungers or taking refreshing dips to cool off after a day of exploring the island. Surrounding the pool, the many palm trees provide both shade and a picturesque backdrop, enhancing the sense of a secluded, tropical haven. Enjoy a poolside BBQ using the propane grill and smoker and the outdoor dining set.brbrTHE LOCATION…brbr73 PALMS is located on Von Phister Street, in a quiet residential area of Midtown, less than a half mile from Higgs Beach, where you can lay on the beach, dine at Salute! or jog with your dog to the Dog Park. Plenty of parking is available for any number of vehicles, mopeds, and bicycles. Best of all, you’re just a few blocks from Old Town and all its attractions.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom: Located on the Second Floor with a King bed, a flat-screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbr** Second Bedroom: Located on the Second Floor with a Queen bed, a flat-screen TV, a closet, direct access to the front balcony, and access to the shared bathroom in the hall with a shower and tub combo.brbr** Third Bedroom: Located on the Second Floor with a Queen bed, a flat-screen TV, a closet, direct access to the front balcony, and access to the shared bathroom in the hall with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & 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 Lushly Landscaped Backyardbr** Private Heated Poolbr** Propane BBQ Grill & Smokerbr** Off-street Parking for Multiple VehiclesbrbrOther notes:brbrbr** 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** Pets Allowed - Small Dogs Onlybr** 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.

**73 PALMS @ MIDTOWN** Renovated Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

3

Bed

Bath

6

Sleeps

$453.5

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrNestled in the heart of Old Town Key West, BLUE HERON’S HIDEOUT is a newly renovated ranch-style home that perfectly blends historic charm with modern luxury. Featuring 4 bedrooms each with an en-suite bathroom, a heated pool, home office, and off-street parking, this exquisite home is a private oasis for discerning travelers seeking both convenience and indulgence. Located in the 700 block of Whitehead Street, you’ll be just steps from all that Key West has to offer. Combined with Last Key Realty’s Five-star Guest Services & In-House Concierge, a stay at BLUE HERON’S HIDEOUT offers the best of Key West living – luxury, privacy, and an unbeatable location.brbrTHE LIVING AREA & KITCHEN…brbrStep inside to discover a meticulously designed interior where every detail has been thoughtfully considered. The fresh renovation has seamlessly integrated contemporary finishes with classic Key West aesthetics, featuring a bright, open living area with a large flat screen TV and comfortable seating options. The spacious kitchen is fully equipped with brand-new stainless-steel appliances and all the tools needed to prepare meals from home (that is when you’re not eating out at one of the many delicious restaurants nearby). The indoor dining table seats 6, with additional seating at the kitchen bar. A convenient home office is located just down the hall and provides a private space if you need to get work done during your stay. There’s also a powder room located just off the living area.brbrTHE BACKYARD & POOL…brbrThe heart of BLUE HERON’S HIDEOUT is its stunning outdoor space. A private, sparkling swimming pool invites guests to cool off and unwind. The pool can be heated to your liking and is complete with waterfall and color changing light. Adjacent to the pool, you'll find comfortable outdoor seating, an outdoor shower, and an outdoor dining area with BBQ grill, perfect for al fresco meals and entertaining. Completely fenced in and surrounded by lush tropical landscaping, the backyard is a secluded haven.brbrTHE LOCATION…brbrWith its prime downtown location, guests of BLUE HERON’S HIDEOUT are just steps away from the island's most iconic attractions. Duval Street, with its lively restaurants, bars, and shops, is a short stroll, as are the historic Ernest Hemingway Home and Key West Seaport. Whether you're seeking cultural experiences, culinary delights, or simply a leisurely walk through charming streets, everything is within easy reach. Even though you won’t need a car to get around from this phenomenal location, the long, narrow driveway will accommodate up to two vehicles.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom: King bed, flat-screen TV, walk-in closet, and a gorgeous en-suite bathroom with double sinks and a walk-in shower.brbr** Second Bedroom: Queen bed, a flat-screen TV, closet, and an en-suite bathroom with a walk-in shower.brbr** Third Bedroom: Queen bed, a flat-screen TV, closet, and an en-suite bathroom with a walk-in shower.brbr** Guest House: Located just off the pool area with a Queen bed, a flat-screen TV, closet, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & 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 YouTube TV 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 & Landscaped Private Yardbr** Private Heated Poolbr** Propane BBQ Grillbr** Off-street Parking in Driveway for Two Vehicles (with vehicle size restrictions - driveway is 8.5ft wide and 47ft deep)br** Electric Vehicle PlugbrbrOther 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 8 adultsbr** 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.

**BLUE HERON'S HIDEOUT @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVI

Key West, Florida, United States

Bed

Bath

Sleeps

$2653.01

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrIt doesn't get any 'sweeter' than vacationing with a large group of your closest friends and family in America's Paradise. As a combination of two side-by-side private homes, SWEET AMERICANA not only offers plenty of comfortable accommodations for the whole crew but is an extremely rare find in the center of Old Town Key West. Located at the end of discrete lane only half a block off Duval Street, this unique Americana-inspired dual home offers all the ingredients of a desirable vacation rental, including:brbr** Two fully equipped kitchensbr** Two spacious living areasbr** Eight Private Bedrooms, each with an en-suite bathroombr** Two private saltwater poolsbr** Two designated off-street parking spacesbrbrSWEET AMERICANA can be rented exclusively through Last Key Realty and includes our Five-Star In-home Guest Services - the cherry on top of what's sure to be the 'sweetest' vacation ever!brbrTHE LIVING AREAS...brbrThe living areas were designed to create an ideal space for a large group wanting to experience Key West in style. Bright colors and funky Key West décor add to the large SMART TVs and comfortable furnishings of the large living areas. In addition, there is plenty of seating for everyone, with plush sofas, chairs, and indoor dining tables. Both living room sofas pull out to Queen sleepers to accommodate extra guests. Each home also has a half bathroom off the living areas for convenience.brbrBoth kitchens are fully-equipped with every appliance and tool needed to prepare a meal at home, that is when you're not enjoying the fantastic array of Old Town restaurant options within walking distance of your front door.brbrTHE PRIVATE SALTWATER POOLS...brbrThe pool areas are connected via an open gate that allows your crew to pass through and mingle between the homes. Fully fenced for privacy, these pools will undoubtedly be the primary gathering places for your group. The saltwater pools can be heated in the cooler months to your liking and get equal amounts of sunshine and shade throughout the day. Comfortable chaise lounges and patio furniture on the pool's decks offer the perfect lounging options for relaxing outdoors. One of the homes has an outdoor shower near the pool for rinsing off after a swim or a day at the beach. Each home has a full outdoor dining set and a propane grill to bring the group together for happy hour or a poolside BBQ.brbrTHE ACCOMMODATIONS...brbrThis compound of two homes will keep your whole group satisfied, with ample space for everyone to escape to their own accommodations, but also relax together in common spaces. Each bedroom has a flat screen TV, an overhead fan, and an en-suite bathroom.brbrBed Configuration Summary:brbrHouse 1brbr** 2 Twins OR 1 King - First Floorbrbr** 2 Twins OR 1 King - Second Floorbrbr** 2 Twins OR 1 King - Second Floorbrbr** King - Second FloorbrbrHouse 2brbr** 2 Twins OR 1 King - First Floorbrbr** 2 Twins OR 1 King - First Floorbrbr** 2 Twins OR 1 King - Second Floorbrbr** King - Second FloorbrbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen HD 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 is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** 2 Fenced and Lushly Landscaped Backyards br** 2 Private Saltwater Pools with available Pool Heatbr** Outdoor Showerbr** 2 Propane BBQ Grillsbr** 2 Queen Sleeper Sofasbr** 2 Off-Street Parking Spaces (with restrictions - NO LARGE VEHICLES)brbrOther notes:brbr** In person welcome br** Interim housekeeping provided upon requestbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** This property will accommodate up to 20 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.

**SWEET AMERICANA @ OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$581.49

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

Afternoon Delight at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$195.06

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

$379.38

Looking for where to stay in Key West, Florida Look no further! Our One Bedroom Loft Villa features a queen bed downstairs and a cozy lofted bedroom with another queen bed, a full kitchen with dining area, and a private porch. The Loft Villa can accommodate a total of four persons: two in the front room and two additional persons in the loft reached by a ships ladder. This villa is great for a Key West family vacation.brbr* Two Queen Bedsbr* Sleeps up to 4 Peoplebr* Full Kitchen with Dining Areabr* Private Porchbr* Shared Heated Poolbr* Continental Breakfast Included Dailybr* Flat Screen TV with Cablebr* Parking by Reservation ($15/night plus tax)br* 200 Feet from Duval Street

Loft Villa Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$306.69

Welcome! This beautiful cottage (sleeps 6) is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally. Remember to bring your shades, flip flops, sunblock and bug repellant! brbrI'm an experienced super host with a handful of rentals and I expect you'll be delighted with the cleanliness and amenities provided at this Poolside Cottage. brbrThe cottage sleeps 6 peoplebrbrSleeping Arrangement:brbrBedroom #1:br- King Size Bed (sleeps 2)br- Two Nightstands with Reading Lampsbr- Dresserbr- 25 Flat Screen TVbrbrLiving Room:br- Sofa with Pull-Out Queen Size Bed (sleeps 2)br- Murphy Bed (sleeps 2)br- Chairbr- Desk and Chairbr- 46 Flat Screen TVbrbrDining Room:br- Dining Table with Seating for 4brbrKitchen:br- Fully Equipped (all things necessary to prepare and serve a meal)br- Coffee Makerbr- Toasterbr- Blenderbrbr--------------------------------------------brbrAMENITIES:br- 2 Outdoor Community Pools and a Hot Tubbr- Picnic Area with BBQ Grillsbr- Boat Slips (limited availability & additional fee. Please see additional information below)br- Trailer Parking (limited availability. Please see additional information below)br- Bikes, Kayaks, Paddle Boards and Golf Carts can be rented locallybr- Full-Size Laundry designated for #411 & #412br- Linen's and Towels ProvidedbrbrThere is one dedicated parking space for #411brbrBoat slip or trailer parking is not included, but guests can reserve a boat slip and trailer parking through Coconut Mallory Resort in advance and for a fee. They are both generally available, though we highly recommend booking as soon as you book the cottage.brbrRegarding reservations: all guests have an option of paying a $59 fee that is non-refundable (it covers us in case of damage) OR you can pay a $1500 deposit that IS 100% refundable, assuming there's no damage.brbrBy reserving the Poolside Cottage, you acknowledge and agree to our Rental Agreement & Release of Liability, which can be found under the Rental Agreement section of this listing. We’ve included this just to keep everything clear and safe, so you can focus on relaxing and enjoying your tropical getaway.

Poolside Cottage #411

Key West, Florida, United States

Bed

Bath

Sleeps

$284.63

The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for those travelers who do not need a suite or kitchen. With one queen-size bed, this accommodation is perfect for romantic vacations and weekend getaways for two.brbr* 1 Queen Bedbr* Sleeps up to 2 Peoplebr* Flat Screen TV with Cablebr* Shared Heated Poolbr* Continental Breakfast Includedbr* Parking by Reservation ($15/night plus tax)br* 200 Feet from Duval Street

Poolside Queen Room Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$417.13

Enjoy a wonderful Key West accommodation. brOur One Bedroom Deck Villa features a living room, a separate bedroom with king-sized bed, and a private deck. The unit also has a full kitchen with a separate dining area. It can accommodate a total of four persons: two in the private bedroom and two additional persons on a convertible sofa in the living room. Enjoy a fun filled Key West family vacation with us.brbr* 1 King Bed, 1 Queen Sleeper Sofabr* Sleeps up to 4 Peoplebr* Full Kitchen with Dining Areabr* Porch with Outdoor Seatingbr* Flat Screen TV with Cablebr* Shared Heated Poolbr* Continental Breakfast Includedbr* Parking by Reservation ($15/night plus tax)br* 200 feet from Duval Street

One Bedroom Deck Villa Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$316.13

The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-sized bed and an additional two on a convertible sofa. Our many Key West, FL vacation villas offer something for everyone!brbr* 1 King Bed, 1 Queen Sofa Sleeperbr* Sleeps up to 4 Peoplebr* Flat Screen TV with Cablebr* Shared Heated Poolbr* Continental Breakfast Includedbr* Parking by Reservation ($15/night plus tax)br* 200 Feet From Duval Street

Poolside King Room Steps from Duval!

Key West, Florida, United States

Bed

Bath