Vacation Rentals By Owner In Key West, FL

Casa Loca is perfect for guests who want to enjoy the finest that Key West has to offer! The perfect location, less than one block from Duval Street, this 3 bedroom, 2.5 bathroom house will amaze you with its extraordinary decor and attention to detail. Sit on the fabulous island style porch and enjoy the classic Key West scenery.brbrAs you enter the main two-story house, you are greeted by a large open floor plan with Greek-style columns framing each area. The entrance level hosts a comfortable sitting area with a queen sleeper sofa and adjacent half-bath. Across the room is a spacious breakfast nook with a large window peering onto the front porch. Just behind is the kitchen, which includes a double door refrigerator with an ice-maker, dishwasher, glass-top stove, garbage disposal, Corian counter tops, and marble back splash.brbrLight pours through the 10-foot glass doors into the expansive, luxurious Great Room that is surrounded by the lush tropical garden. Hardwood floors throughout the home blend beautifully with the elegantly appointed high-end furnishings. Enjoy the six-person formal dining suite just steps away from the stylish living room, complete with a flat-screen TV, DVD player, and stereo system. You will appreciate the distinct details, including a backlit stained glass mural in the ceiling, which adds the perfect ambiance to this romantic space.brbrWalk out the through the glass doors to your very own heated pool with a hand-crafted stone fountain built in. Comfortable padded lounge chairs surround this tropical paradise with various assorted bromeliads, traveler palms, and tropical orchids. Equipped with an outdoor shower with a solid wood privacy screen and gas Weber BBQ grill, this outdoor living area is the perfect place to relax and entertain.brbrAcross from the pool area in its own private wing of the house is an airy, spacious, private primary bedroom with French doors that open up to the pool/garden area. This room features a high-quality Serta king bed with down duvet, TV and DVD player, ceiling fan, and an intimate bath with a marble shower. This large primary bath with a stunning glass block wall also features a full-size Maytag stacked washer/dryer for your convenience. Upstairs in the main house are two bedrooms: one with a king bed and TV; and the other with a queen bed and TV/DVD. A tropically-infused large common area shared by the two bedrooms has cozy seating with a sofa and chairs, as well as a beautifully detailed full bath. Casa Loca is outfitted with the finest luxury linens, down comforters, and thick beach and bath towels. An iron and ironing board, central A/C, and additional room A/C units complete this exclusive, one-of-a-kind estate in the heart of Old Town Key West! brbrParking in Key West is very limited. If you have a vehicle you are responsible for finding your own parking. If you rent a car and drive from Miami you may want to consider returning your car once you are in Key West. There is no assigned parking for this property.

Casa Loca - so close to Duval 3bd/2ba private home

Key West, Florida, United States

Bed

Bath

Sleeps

$497.66

Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of unparalleled exclusivity.brbrThe foyer of this Mediterranean-style unit opens to the living room, dining area, half-bath, and kitchen. The living room contains a queen-sized sofa bed, flat-screen TV with cable, side tables, and a dining area for six. It also features French doors opening to your own private outdoor patio with chairs. With a breakfast nook for two to enjoy your morning coffee, the open kitchen is fully-equipped with a refrigerator, stove/oven, dishwasher, washer/dryer, drip coffee maker, and toaster.brbrUpstairs, the primary bedroom has a king bed, sofa for lounging, and French doors opening onto a private porch with seating. The primary also has a large ensuite full bathroom with a walk-in shower, vanity, and skylight. The second bedroom features a queen bed and private full bath.brbrShops can be found below you in Duval Square's shopping center! You can also walk to Key West's many bars, restaurants, art galleries, and shops.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

THALIA'S RETREAT @ Duval Square 2bd/2ba townhome

Key West, Florida, United States

Bed

Bath

Sleeps

$370.95

Enjoy a cocktail or gaze at the stars in the private hot tub on treetop deck. The Treetop Oasis is completely equipped for your every need on your Key West holiday!brbrThis Treetop Oasis is a light and airy studio occupies the entire second floor of the Eyebrow House, just a half block off Duval Street. brbrThe Treetop Oasis is a spacious suite features a sofa sitting area that doubles as a queen sleeper sofa for extra guests. A wall of kitchen cabinety with gas stove, refrigerator and dishwasher provides an opportunity for guests to enjoy a home cooked meal while visiting. Although with Duval Street so close, a choice of restaurants . brbrThe Oasis has a comphy king bed to provide a restful night sleep after a day of fun around town. An elegant bath with walk-in shower adjoins the suite for a luxurious getaway. brbrAfter a day of touring historic Key West sights, a day at the beach at Fort Zachary Taylor or a night on Duval Street, guest may return to the Treetop Oasis and enjoy the rooftop deck with a relaxing spa. The perfect way to end the perfect day in Key West!

Apartment

On top of it all @ TREETOP OASIS

Key West, Florida, United States

Bed

Bath

Sleeps

$1115.46

Pilar’s Secret is hidden away in the heart of Old Town Key West just half a block off the famous Duval Street. This secluded oasis is the perfect spot for you to truly discover the ultimate Key West experience. brbrLocated down a quiet and nondescript lane, Pilar's Secret gorgeous property is quintessentially Key West with well appointed luxury amenities throughout.brbrPilar’s Secret offers three very spacious bedrooms, a private pool, and wonderful gated outdoor living area. The fully equipped kitchen is adjacent to a large living space with plenty of room for all your guests to relax. Pilar’s Secret was designed for sharing with family or close friends. The spacious home makes a perfect home base for a group while they enjoy everything our island has to offer. The living area has plenty of seating on plush couches and chairs. One of the living room sofas pulls out into a sleeper sofa for added guests. brbrThe kitchen is just off the main living area with top-of-the-line appliances and all the tools you need to prepare a meal at home in between your nights out enjoying our island cuisine. There are many options for dining just a short walk from Pilar’s Secret.brbrLush tropical landscaping and comfortable chaise lounges and chairs surround the pool at Pilar’s Secret. This very private outdoor area has seating for lunch or dinner, plus ample amounts of sun and shade throughout the day for picturesque outdoor living. The pool can be heated and the grill is ready for your next meal either poolside or at the other larger outdoor dining table alongside of the house. String lights, pool lighting, and the beautiful landscaping create an enchanting space come dusk. There is also an outdoor shower for rinsing off after a day at the beach.brbrThere are two bedrooms located on the ground level of Pilar’s Secret. One bedroom has two twin beds. The second bedroom has a king size bed, a flat screen television, and French doors leading out to the side patio. These two bedrooms share a bathroom with a glass shower and soaker tub. brThe second floor primary suite is private with a king size bed, flat screen television, ensuite bathroom and its separate seating area. The bathroom has a unique spa-like shower. This is the perfect place to get away and wind down after an active day around Key West.brbrPilar’s Secret offers central A/C and heat and there are ceiling fans throughout. The private pool can also be heated upon request. The yard is private and provides lush landscape throughout. There is a gas grill, one private parking space, a washer/dryer, and flat screen televisions in the living room and in each bedrooms all with expanded cable TV. The gourmet kitchen has all the utensils for preparing your meals along with a microwave, blender, and toaster. Linens and towels are provided and housekeeping is available in the interim upon request and for additional fees.brbrThe home has wireless high-speed internet included. The property will accommodate up to 8 people with 3 bedrooms and a pull-out sofa. Sorry, no pets. This vacation rental property offers secure, coded keyless entry with contactless check in.

No secrets at Pilar's Secret - Just a great location!

Key West, Florida, United States

3

Bed

Bath

8

Sleeps

$458.71

This is a unique home in Key West Golf Club Club Community available for your vacation rental experience. brStay on the only 18-hole golf club in the Florida Keys and enjoy the lush tropical foliage and resort style amenities! The property provides open living areas downstairs and comfortable bedrooms upstairs. The master bedroom has a King bed, ensuite bath with dual vanity and tub/shower combo. There is also a lovely screened balcony to enjoy your evening wine or morning coffee overlooking the golfing green. Each guest bedroom has a comfortable queen bed and ample storage for your extended stay. The shared bath is in the hallway and has a combination tub/shower. Enjoy the balmy southerly breezes across either of the screened in porches to take in the morning sunrise or evening sunsets while sipping your favorite beverage and enjoy the relaxing Caribbean lifestyle as your stress melts away. Community amenities include two common pools, one is just steps away from your front door along with a nicely equipped fitness center. A secondary pool is located near the guard station toward the entrance of the community. Each offer additional Wi-Fi to stay connected if needed. You also have parking for up to two vehicles. Please note there are vehicle size/type restrictions as dictated by the HOA. We can furnish these details on request as well as . Note: This property has a 28 night minimum stay requirement.

Cottage

A Conch Casita at the Key West Golf Club

Key West, Florida, United States

Bed

Bath

Sleeps

$450.81

OLD TOWN KEY WEST…brSurround yourself in this newly renovated gem located in the desirable Casa Marina neighborhood nearing the Southernmost Point of the U.S. This tropical retreat begs for entertainment in the exceptional outdoor living space and resides steps away from high end galleries, the beautiful beaches of Key West and some of the most coveted dining downtown!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brLush vegetation surrounds this island retreat welcoming you into your escape from reality. A private, covered front porch greets you as you enter the home in to a cheery seating area with an indoor dining table and writing desk nearby. Steps away is the fully equipped kitchen with charming brick accent walls and casual bar top dining. Cozy furnishings surround a flat screen TV just steps away. Tile flooring throughout this home will keep you cool during a warm island afternoon. brbrSLEEPING ARRANGEMENTS…brTotaling 4 bedrooms, this home is perfect for families and couples traveling together. Sleep tight in the twin bed guestroom of which can be converted to a king upon request. A cozy queen bedroom lies steps away. Both rooms come with TVs and share a bathroom with a walk in glass shower. The primary king suite is equipped with a flat screen TV and en suite bathroom with a walk in glass shower. French doors lead out to the lush outdoor garden for your morning cup of coffee. The living space includes a sofa sleeper for visiting guests. There is a 4th bedroom poolside that comes with 2 twins and an en suite bathroom with a shower. brbrOUTDOOR LIVING…brStep through the French doors of the kitchen to your pristine outdoor oasis which makes for the ideal 5 o’clock happy hour with plenty of space to lounge and entertain. An outdoor TV, ice maker and refrigerator complete the outdoor wet bar. Grill up your fresh catch of the day and catch some rays on the spacious pool deck in the privacy of your fenced in backyard. The saltwater pool comes heated in the winter months and has the option of being chilled during the months of June-August at an additional charge if requested. Rinse off in the outdoor shower before heading out on the town. brbrPARKING AND BIKES...brTwo off-street parking spaces make parking your vehicle a breeze, and 4 bikes are also provided. brbrPETS...brDogs are considered, no cats please. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. A pet fee is required.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrISLAND TIME IS AWAITING YOUR ARRIVAL…

EBB AND FLO ~ Newly Renovated Retreat in Old Town with Incredible Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$277.02

IMMACULATE UPSCALE DELIGHT…brEmbrace the island vibes and immerse yourself in the Key West spirit in this enchanting 3 story coastal contemporary townhome. Centered in the heartbeat of Old Town - the upbeat and lively district of the Conch Republic - this dreamy abode is just steps to high end galleries, museums and all the best nightlife action. It is also tucked away as your peaceful sanctuary.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brSip your morning brew and plan your day's excursions on the cozy front patio couch and chairs as balmy breezes awaken your senses. As you enter the home, you are greeted by a living area that combines modern whimsy with functionality. Relax on the oversized sectional and enjoy the large Apple TV (Sonos speakers in all rooms) for your bingeworthy viewing pleasure. A table for 4 is located in this space so you can dine while you view. The large picture window floods the space with sultry island sunshine. A powder room is situated on the first floor for your convenience. As you enter the sparkling and immaculate white kitchen, let your culinary cravings be satisfied with all the modern conveniences and appliances your inner chef desires. The Smeg refrigerator and toaster oven will delight your nostalgic heart and the cabinets are fully stocked with everything you'll need to concoct delicious meals for your loved ones. brbrSLEEPING ARRANGEMENTS…brTravel up the staircase to the second floor, which offers two rooms, one with a queen bed and the other with two twin beds (trundle). The queen room has an ample closet for hanging clothes and storage. The twin room features abundant natural light from two french doors that open to a viewing veranda for welcoming the day. It has a full size closet for hanging clothes and storage. A shared bathroom on this floor offers a tiled glass-door shower with a large mirror and single sink. On the third floor lies the primary room with a plush king bed. Recessed windows allow volumes of vibrant sunshine to brighten your mood. A dresser and built in drawers provide storage for your valuables and clothing. Unwind at night with your large Apple TV and cooling ceiling fan. A full bathroom with a shower/tub combination and washer dryer station lie across the hall. brbrOUTDOOR LIVING…brGrill up your fresh catch of the day as you sip on your cocktail beneath the stars. This home is just a short bike ride to all the beloved Key West attractions. brbrPARKING...brThis home offers parking for one vehicle.brbrPETS...brThis is a pet friendly home and a pet fee is required. Please make sure to check the box that you are bringing a pet when booking, and include size, breed, and age of the pet in Comments/Special Requests.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). brbrFIND YOUR ZEN…

UPTOWN FUNK ~ Newly Renovated 3 BR Townhome in Old Town with Parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$125.49

Consider this mobile your home away from home while you visit Key West. This property features 1 bedroom with a queen bed, 2 bathrooms, an office, and an additional living room space with 2 pull out sofa beds. Guests can enjoy amenities like WiFi, AC, and a washing machine during their stay. House is canal front and has a 32 foot boat slip. Phenomenal comfort and convenience await you at this terrific rental. Enjoy all that Key West has to offer when you stay at our place.

Mobile Home

Canal Front Home Cute and Cozy w/ 32ft boat slip

Key West, Florida, United States

Bed

Bath

Sleeps

$144.37

Kick off your flip flops in this wonderful newly renovated 1 bed,1 bath guest house! After a day at the beach or a late night on Duval, you will love the privacy and cleanliness of Casa Duck.brPrivate entrance, outdoor shower, fenced-in yard, and patio. brbr* NEW* Fully stocked Kitchen with Stainless Steel Appliancesbr* NEW* Full-size closet, with dressing unitbr* NEW* Full-size Washer & Dryerbr* NEW* Large flat-screen TVbr* NEW * Bed/Furniture

Cottage

Remodeled cozy retreat - Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$956.25

Concierge Realty is proud to present luxury villas at Hyatt Sunset Harbor!brbr**Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only.brbr**All bookings are time sensitive and availability can change at any time. Send us a message to confirm exact availability prior to making a booking request. brbrWhere Fun Meets Sun!brbrDiscover a relaxing oasis overlooking the Gulf of Mexico in the heart of Old Town, steps from the shops, galleries, and cafes of Duval Street, and close to the nightly sunset celebration at Mallory Square. brbrHyatt Sunset Harbor’s spectacular gulf coast setting is matched only by the gracious service, top-tier amenities and meticulous attention to detail.brbrTropical Key West welcomes you to this classic Florida two-bedroom villa, offering a master suite with plush king bed and connecting bath with available jetted spa tub. In addition, there is a guest suite with queen bed and full bath. This two-bedroom unit offers a fully-equipped kitchen, dining area, seating area with TV, stereo and DVD player and private balcony with pool or harbor views.brbrThe ultimate luxury amenity here is the incomparable location in the heart of Old Town. Tin-roofed conch houses, historic museums, quirky locals and art treasures. If you love Key West, you’ll love it even more when staying at our villa!brbrThe Vrbo calendar helps provide availability and estimated price quote. Always inquire with the agent and do not reserve airfare until your confirmation has been received.brbrAny issues with resort service, accommodations, physical plant, amenities, etc. are the direct responsibility of the developer and must be handled through the resort, not Concierge Realty. Photos are thought to be truly representative of the resort and accommodations. Any variation from the photo and actual property are unintentional, so guests are encouraged to do their own due diligence prior to reserving. Any variance or disruption including but not limited to renovation, unavailable amenity, change in decor, etc. during the stay, whether announced prior to reservation, occurring during the stay or announced after confirmation, is a matter strictly between the guest and resort, are not deceptive advertising, breach of contract or the responsibility of Concierge Realty.brbrNote that the images are representative of this villa and that a specific view type is not implied nor promised by virtue of the images. A specific view category must be addressed with rental agent. Concierge Realty reserved the right to reserve any view category unless one has been agreed upon in writing. The resort confirmation will show the view designation and the villa will be placed within that view category unless, in a rare instance the view will be noted as not guaranteed in which case the resort reserves the right to place the guest anywhere within the property. Issues regarding view within the guaranteed view category are to be addressed with the resort management as Concierge Realty is not responsible for villa placement.brbrPlease be advised that if a non-domestic credit card is used to reserve a vacation rental, additional fees may be incurred.brbrAll details are accurate to the best of our knowledge. Any questions with regard to view, amenities, bedding configuration, decor or other details should be addressed with Concierge Realty, Winter Garden, FL.brbrGuests are encouraged to do their own due diligence to assure that the resort and villa will meet their expectations.

Hyatt Sunset Harbor, 2BD overlooking the stunning and beautiful Gulf of Mexico!

Key West, Florida, United States

Bed

Bath

Sleeps

$772.09

OLD TOWN PARADISE....brParadise awaits in a quiet Old Town location. This four bedroom home is set on a cozy lane that is off the beaten path but close enough to walk or ride your bicycle to restaurants, museums or galleries. Newly renovated and designer decorated to bring you a home with island details and a luxurious flare. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES....brThis charming 4 bedroom/4 bath home is set on a historic lane with one off street parking spot. Open the front gate to step onto the lovely front porch where seating is laid out to take your morning coffee. Once inside the front door you will enjoy the mix of historic and modern which mesh seamlessly. Hardwood wood floors carry you throughout with the exception of the tiled bathrooms. You will find the kitchen to be fully equipped to meet all your cooking needs. White cabinets and stainless steel appliances make this space light & bright and an enjoyable gathering space. A full bathroom is conveniently located off the kitchen. This is great for entertaining and can also double as the pool bath. brbrSLEEPING ARRANGEMENTS....brThe primary bedroom is conveniently located on the main level. This bedroom is equipped with a large closet and a comfortable king size bed. The master bathroom in on suite and has a tub for soaking, a tiled shower and double vanity. Travel up the wood stairs to the two guest bedrooms. High ceilings and wrapped wood beams add great architectural detail to these rooms. The front bedroom has two twin beds that can be converted to a king upon request. There is a long closet for all your storage needs. The second guest bedroom has a king size bed with a closet and views of the pool. The guest bathroom is located between the two bedrooms. The bathroom is equipped with a large shower and a single vanity. The fourth bedroom is located in the private rear cottage. The cottage has a queen size bed and its own full bath. Each sleeping space has a flat screen TV.brbrOUTDOOR LIVING...brThe rear yard is a private oasis that will make your vacation complete. There is a private L-shaped salt water pool which is heated and has a calming water feature. Whether floating in the pool or lounging in a chaise, relaxation awaits. If you're interested in enjoying your surroundings from the indoors, there is a beautiful solarium where you can relax with a book, get some work done or just take a break from the Florida sunshine. It is preferred that this area remain for adults only. br br**Since photos were originally taken the owner has added 2 lounge chairs and an L-shaped wicker sectional to the seating in the pool area, as well as a propane grill.brbrPETS...brThis is not a pet-friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrPARADISE AWAITS...

BLUE ROOSTER ~ Spectacular 4 Bed/4 Bath with Pool and Solarium in Old Town!

Key West, Florida, United States

4

Bed

4

Bath

8

Sleeps

$712.1

Discover Old Town living at its finest. Tucked away on a quiet, tree-lined residential street in the coveted Historic District, this home puts you steps from the iconic Casa Marina, Higgs Beach, Southernmost Point, Duval Street, and some of Key West’s best restaurants. Whether you settle in for a month or longer, this extraordinary property is the kind of place you’ll never want to leave - and the one you’ll find yourself dreaming about long after your stay ends.brbrNOTE: This listing is for the Main Home plus one offstreet parking space.brbrAs you enter the main home you will be captivated by the huge high-end chef's kitchen, natural light, and hardwood floors. A white, quartz waterfall island has seating for four and a built-in microwave. Custom cabinets, recessed lighting, and stainless-steel countertops complement this unique home. Stainless steel KitchenAid appliances and a large refrigerator are sure to impress the Chef in your group.brbrThe adjacent open-concept living room/dining room and convenient powder room are accented with Dade County pine and designer decor. A large L-shaped sleeper sofa, chair, and two swivel chairs provide views of the large-screen TV as well as the pool. The dining area seats 6 comfortably at the trestle table with nail head trim seating.brbrA lighted staircase at the entry leads to the primary bedroom, a luxurious retreat, and an immense spa-styled bath, complete with private access to the front porch as well as a large oversized 2nd floor back deck accessed through double French doors and a bank of windows! It is adorned with a woven rattan bed, nightstands, lamps, a dresser, and large screen TV. Two large closets are also provided for your extended stay. The oversized ensuite bath includes a double walk-in shower, multiple shower heads, a soaking tub, a water closet, and dual sinks with lighted coral mirrors. The stackable washer and dryer is conveniently located on the 2nd floor of the home.brbrThe 3rd floor has two additional ensuite bedrooms flanking the hall. The first guest bedroom includes a queen bed, nightstands with lamps (each with built in usb charging) built-in open shelving, dresser, closet, and desk, as well as an ensuite bath. The second guest bedroom has a canopy bed, side tables with lamps, a closet, as well as its own cozy, modern ensuite bath. brbrStepping outside through the double French doors, you'll be transported to your very own private oasis. The backyard is surrounded by privacy fencing and features lush tropical landscaping. You'll have plenty of room for everyone to lay out and relax or enjoy an outdoor meal. Taking a dip in the heated saltwater pool and spa is the perfect way to relax after a day of exploring the island. Treat everyone to a poolside BBQ using the propane grill and outdoor dining table. There's even a convenient outdoor shower located by the pool area.brbrNOTE: If you are interested in renting the Pool Home/Guest Cottage, we have a separate VRBO listing.

Impeccable 3BR/3.5BA Coastal Escape Steps from Casa Marina & Higgs Beach

Key West, Florida, United States

3

Bed

3

Bath

8

Sleeps

$299.96

Welcome to your charming Key West retreat with private pool and a lush, tropical garden. Designed for comfort this 2 bedroom /2 bath has a fully equipped kitchen. Enjoy peaceful surroundings just minutes from the island's best dining & beaches. 28-night minimum stay required per local regulations.

The Little Mermaid

Key West, Florida, United States

Bed

Bath

Sleeps

$1331.42

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrWith a sense of gracious royalty, QUEEN OF LOUISA will treat you to an unforgettable stay in Key West. Her ideal location, modern interior, private saltwater pool and thoughtful touches throughout will ensure you and your group have everything you could want in a vacation rental. QUEEN OF LOUISA offers cozy bedrooms, a fully stocked kitchen and a fantastic outdoor space with a private saltwater pool for you and your guests to enjoy. Your stay also includes Last Key Realty's Five-Star Guest Services to make sure you receive the royal treatment.brbrTHE LOCATION...brbrLocated a half block off of the Southern end of Duval Street, QUEEN OF LOUISA will make you feel like royalty: you can walk to Duval St, you’re only a few blocks from the Southernmost Point, Fort Zachary Taylor State Park, or any other Old Town attraction you may want to explore. You'll be a short walk or bike ride to all that Old Town Key West has to offer. The best part is you’re on the “quiet” end of Duval St, which means you can easily head down to the fun, but you don’t have to worry about it keeping you up at night. While you won’t need a vehicle from this prime location, the private driveway serves as your off-street parking space in case you decide to rent a car or golf cart.brbrTHE LIVING AREA & KITCHEN…brbrQUEEN OF LOUISA has a comfortable living area that features a large flat-screen TV and plush seating, including the sofa that pulls out to a Queen sleeper for extra guests. Double French doors off the living room open straight to the private pool area. The open-concept living area flows right into the fully-equipped kitchen. This contemporary kitchen includes all of the comforts of home, with modern appliances and plenty of cabinet space. There is an eight-person dining table, so everyone can enjoy a meal together.brbrTHE SALTWATER POOL...brbrOut the back doors is your fully fenced backyard with a heat-optional saltwater dip pool. Beside the pool are chaise lounges so you can soak up some sunshine. There’s also an outdoor wet bar so you can whip up a tropical cocktail after a refreshing dip. On the pool deck sits an outdoor dining set with seating for up to eight to enjoy a meal on those tranquil tropical nights.brbrTHE ACCOMMODATIONS...brbrAll bedrooms in this lovely home are located on the first floor. No stairs necessary!brbr** Master Bedroom: King bed, large flat-screen TV, and en suite bathroom with a walk-in shower.brbr** Second Bedroom: King bed, flat screen TV, large flat-screen TV, and en suite bathroom with a walk-in shower.brbr** Third Bedroom: Twin Beds (or convert them to a king), flat screen TV, and en suite bathroom.brbr** Fourth Bedroom: Twin Beds (or convert them to a king), flat screen TV, and access to the hallway bath.brbr** Bonus Room/Office: Dedicated work desk, large flat-screen TV, Queen sleeper sofa, access to pool deck and to the shared bathroom in the hall.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced Yardbr** Private Heated Saltwater Poolbr** Propane BBQ Grillbr** Off-Street Parking for 1 Vehiclebr** Two Queen Sleeper SofasbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 12 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per pet

**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES

Key West, Florida, United States

6

Bed

5

Bath

12

Sleeps

$675.0

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 work out in the onsite fitness center. Enjoy fishing off the private dock, or rent bicycles and take in all that Old Town Key West has to offer.brbrThe spacebrThis 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 one queen bed, 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.brbrGuest accessbrUpon arrival please go to the front desk. ID matching your name and credit card is required. Your credit card will be authorized for a refundable security deposit.brbrOther things to notebrPlease note, guest bedroom may feature 2 twin beds or 1 queen bed.brbrUpon booking, you will be asked to verify your full name and address matching your ID. You will be asked for your email address for the purpose of receiving your resort issued confirmation. Please note, Vrbo confirmations will not be accepted at check-in. Your ID will be required at check-in for verification purposes along with a credit card for a refundable security deposit.brbrAn ID and a credit card is required upon arrival for a refundable security deposit.br$75+tax resort fee per each week (7nights) due at check-in, along with a refundable $150 deposit, as long as no damages occur during your stay.brbrHousekeeping changes linens and towels on Wednesday only. If daily housekeeping is desired, there is an additional charge imposed for it by the resort.brbrParking for 1 vehicle per unit (No oversized vehicles, RV's or trailers) No availability for multiple vehicles.brbrUnits are assigned in 7 night increments.brbrPlease note, we 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.

Galleon Resort, Private Beach, Tiki Bar, Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$748.48

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.

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

Key West, Florida, United States

Bed

Bath

Sleeps

$682.61

Welcome to Pretty’s Place, A newly renovated home which blends modern luxury with timeless Key West character. Updated from the ground up, this property offers a main home with 3 Bedrooms and 2.5 bathrooms as well as a separated Studio space complete with 1 Bedroom, Kitchen and full bath that can easily accommodate up to 6 Guests.brbrMAIN HOME 1ST FLOOR:br-First floor bedroom sweet with King Bed and Large walk inn showerbr-Main floor laundrybr-1/2 bath off hallwaybr-Kitchen fully equipped w/island seating for 6 and additional 5 person eating space.br-Large wrap around couch to relax in living space with YouTube TV / Smart TVbr-Double Sliders lead to rear Pool Spacebr-Hardwood Floors, Central Air, tiled bathsbrbr2ND FLOOR:br-2 Bedrooms both with Queen bed and oversized closetsbr-Cathedral Ceilingsbr-Large full bath with walk inn Showerbr-Hardwood Floors, Central Air, tiled bathsbrbrREAR STUDIO:br-Queen bed with TV and slider to pool spacebr-Tiled bath with shower and pool accessbr-Full Kitchen and storagebr-Air conditionedbrbrEXTERIOR GROUNDS:br-Cover farmers porch to enjoy morning coffee and evening cocktailsbr-Heated pool and connected Hot Tubbr-Large private Ipe deckbr-Lounge area on deck to lay out with umbrella and lighting br-Dining Area on Deck with Bistro Lightsbr-Outdoor Shower to rinse off after poolbr-Off Street Parkingbr-Secluded landscape with fenced in yard for privacybrbrTHE LOCATION…brPretty’s Place is located on Royal St., a perfect location between Higgs Beach and Duval St. right in the heart of Old Town, you'll be just steps from all of the shops, restaurants, and sites. Although you won’t need a vehicle to get around from this prime location, there is off-street parking for one vehicle available in the private driveway.brbrHOME INCLUDES:br* Washer & Dryerbr* Central Air Conditioningbr* Ceiling Fansbr* Flat Screen Cable TVs in Living Room & Rear Studiobr* 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 YouTubeTV is includedbrAdditional Items:br* Fully Fenced & Landscaped Private Yardbr* Private Heated Poolbr* Outdoor Showerbr* Propane BBQ Grillbr* Off-Street Parking in Drivewaybrbr**OTHER NOTES**br*This property can rent to 8 peoplebr*Primary Guest must be at least 25 years of agebr* All monthly rentals include a mid stay clean. br*Weekly pool and landscaping br*Additional interim cleanings availablebrbrPETS...brNo pets please.brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night min.). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCANCELLATION POLICY:brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January - March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).

-LUXURIOUS 4 Bd, 3.5 Bth off DUVAL-OLD TOWN-Modern, Pool/hot tub-Separate Studio

Key West, Florida, United States

Bed

Bath

Sleeps

$642.29

Mar Y Sol – Luxury Oceanfront Condo in Key WestbrBreathtaking Views. Unbeatable Comfort. Perfect Location.brbrWelcome to Mar Y Sol, a stunning oceanfront condominium located at 1800 Atlantic, Key West. This beautifully renovated 3-bedroom, 2.5-bathroom vacation rental offers sweeping views of the Atlantic Ocean and resort-style amenities — all just minutes from the heart of Old Town.brYour Private Oceanfront Escapebrbr Spacious 3 Bedrooms / 2.5 Bathroomsbr 60-Foot Wrap-Around Balcony with panoramic ocean viewsbr Fully renovated kitchen and bathroomsbrbr Sleeps up to 8 guests comfortablybrbr Primary Bedroom: King bedbr Guest Bedrooms: Queen bedsbr Additional Guests: Two inner spring roll-away bedsbrbrResort-Style Amenities at Your Fingertipsbrbr Large Heated Pool & Jacuzzi Spa – Just a one-minute walk awaybr On-Site Sauna for relaxationbr Exclusive Clay Tennis Court – The only one on the island!br Lush tropical landscaping and direct beach accessbrbrExplore the Best of Key WestbrbrLocated less than 1.5 miles from the historic district, Mar Y Sol offers convenient access to:brbr Duval Street shopping & nightlifebr Iconic landmarks like the Southernmost Point & Hemingway Housebr Snorkeling, boating, and sunset cruisesbrbrPlan Your StaybrbrWhether you're visiting for a romantic getaway, a family vacation, or a tropical escape with friends, Mar Y Sol is your perfect island home.brbr Please note: Minimum stay requirements may vary throughout the year. Contact us for details and availability.brbrThis Condo is located in a residential condominium complex. Rules & regulations of the complex are provided and strictly enforced. Guests are required to register with the Condominium Association and provide a copy of the Primary renters Government issued Photo ID. brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Mar Y Sol –Luxurious oceanfront Key West Breathtaking Atlantic Sunrise Views

Key West, Florida, United States

Bed

Bath

Sleeps

$411.19

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrSUZY'S PARROT PERCH is a charming apartment that is located in the heart of Old Town on the corner of two historic streets (Whitehead and Virginia) just steps from Duval and two blocks from the Southernmost Point. You couldn't be any closer to the nightlife and attractions on Duval Street (Flamingo Crossing, the famous homemade Key West ice cream parlor, is just around the corner, La Te Da is a block away), and yet this cozy 795 square foot condo is perched on the second floor of a two-story building, with its own quiet balcony away from the hustle and bustle.brbrTHE PORCH...brbrThrough a quaint gate off of Whitehead Street, you will climb an outdoor staircase hidden from the street by tropical foliage. At the top you'll find an outdoor porch area overlooking Virginia Street, and down the lane, Duval Street. From this viewpoint, it's obvious how this Parrot Perch got its name. This home is equipped with comfortable patio furniture for enjoying happy hour while doing some people watching from above.brbrTHE LIVING AREA...brbrThe first thing you'll notice as you open the front door of SUZY'S PARROT PERCH is the openness of the living area. As you enter the apartment, you'll be greeted with a comfortable living room area with plush couches and a flat screen TV. One couch pulls out to a Queen sized sofa sleeper to sleep 2 extra guests. From the living area couches, you can peer out the window and see the treetops across Virginia Street.brbrTHE KITCHEN...brbrBehind the living area, the open kitchen is fully equipped with state-of-the-art appliances, including a modern LG refrigerator with lower freezer for easy accessibility. The kitchen is also equipped with an electric stove, oven, and a dishwasher for easy clean up after meals. The kitchen area also has a high-top table and barstool seating for four. There's even a sound system to set the mood while having dinner.brbrTHE ACCOMMODATIONS...brbr• Master Bedroom: King bed, full closet, flat screen TV, and a private porch. brbr• Second Bedroom: Full bed and flat screen TV.brbrThe shared hall bathroom has a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen TVs in Living Room and All Bedroomsbr• Fully Equipped Kitchenbr• Basic stock of spicesbr• Starter supply of paper productsbr• Starter set of cleaning productsbr• Linens and Towels providedbr• Wireless high-speed Internet access and full cable includedbrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 6 adultsbr• Pets Not Allowedbr• Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.brbrNEED MORE SPACE... brbrAdd the rental of THE MELLOW MACAW, the 2 bedroom apartment downstairs from SUZY'S PARROT PERCH, to create a total of 4 bedrooms, 2 bathrooms, a private deck, and off-street parking.

**SUZY'S PARROT PERCH @ OLD TOWN** Cozy 2nd Floor Condo + LAST KEY SERVICES...

Key West, Florida, United States

Bed