Vacation Rentals By Owner In Key West, FL

Summary:brbrDiscover your dream Key West getaway at Lunara Bay - a collection of 26 Luxury homes in a gated community! Floralee House is a 6BR, 6.5BA luxury waterfront estate that seamlessly blends high-end finishes with modern elegance, just minutes from downtown. Dock your boat right in the backyard, unwind in your pool, enjoy complimentary gym access, and enjoy curated itineraries from our local guest experience team.brbrbrbrElevate your visit with our Private Chauffeur Service for effortless transportation.brbrbrbrThe Space:brbrEnter a space where modern sophistication blends seamlessly with tropical style. The spacious living areas are perfect for relaxation or entertaining, illuminated by large windows that let in plenty of natural light. Every bedroom serves as a peaceful retreat, complete with luxurious bedding and private en-suite bathrooms for extra comfort and privacy.brbrbrbrThe bed layout is as follows:brbrBedroom 1: King BedbrbrBedroom 2: Two Bunk Beds with two queen and two twin sized MattressesbrbrBedroom 3: King BedbrbrBedroom 4: King BedbrbrBedroom 5: King BedbrbrBedroom 6: King BedbrbrAll bedrooms have an ensuite bathroombrbrbrbrGuest Access:brbrOur self check-in makes the process seamless. brbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrbrbrBoating & Private Dock Slip:brbrWe encourage boating. Here's what you need to know in order to do so safely:brbr- Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip.brbr- There is no power or pump out service to the slips.brbr- The Florida Keys are a notoriously difficult place to navigate.brbrbrbrThe Neighborhood:brbrWelcome to Lunara Bay!brbrNestled in a gated community less than a mile from Key West, Lunara Bay offers a family-friendly atmosphere with a local park just a short walk away—perfect for spending time with loved ones.brbrbrbrExplore & Dine Nearby:brbrEnjoy fresh seafood and local flavors at Hogfish Grill, Roostica, or Chico’s Cantina. Visit Hurricane Hole for happy hour and scenic waterfront views. Rent a boat for a day at Stock Rock Café or embark on a kayak tour with Lazy Dog.brbrbrbrBoating & Marina Access:brbrMany homes offer private boat docking or slips available at the onsite marina. A public boat ramp is conveniently located across the highway - Key Haven Boat Ramp.brbrbrbrNeed personalized recommendations Ask your GEM for their top things to do and places to go!brbrbrbrGetting Around:brbrTravel by car, boat, or plane to Floralee House. The driveway allows parking for up to 2 vehicles and your boat trailer. brbrIf you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. brbrRent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Private washer/dryerbrbr- Located in gated community.brbr- Free gym access at FYTbrbr- Fans inside bedrooms only operate with the light on.brbr- Pets are welcome! Our requirements are as follows: brbr•40lb maximum per petbrbr•$250/staybrbr•2 pet maximumbrbrbrbrInteraction with Guests:brbrYour dedicated GEM is at your service to answer any questions or curate unforgettable experiences tailored to your dreams in the Keys.

Floralee House at Lunara Bay

Key West, Florida, United States

Bed

Bath

Sleeps

$1571.13

Summary:brbrPalmgale Estate is a luxurious 6-bedroom, 6.5-bath home at Lunara Bay - a collection of 26 luxury homes in a gated community! Located just minutes from Key West’s vibrant center, it offers a private slip at our exclusive marina for boats up to 40’. Enjoy the convenience of docking steps from your door, plus free access to FYT gym. Our guest experience managers can craft a customized itinerary for your group. Contact us for more info and elevate your vacation experience!brbrbrbrThe Space:brbrStep into a realm where contemporary elegance meets island charm. The expansive living areas invite you to unwind or host gatherings, filled with natural light from generous windows. Each bedroom offers a serene escape, featuring plush bedding and private en-suite bathrooms for ultimate comfort and seclusion.brbrbrbrThe bed layout is as follows:brbrBedroom 1: King BedbrbrBedroom 2: Two Bunk Beds with two queen and two twin sized MattressesbrbrBedroom 3: King BedbrbrBedroom 4: King BedbrbrBedroom 5: King BedbrbrBedroom 6: King BedbrbrAll bedrooms have an ensuite bathroombrbrbrbrGuest Access:brbrOur self check-in makes the process seamless. brbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrbrbrBoating & Private Dock Slip:brbrWe encourage boating. Here's what you need to know in order to do so safely:brbr- Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip.brbr- There is no power or pump out service to the slips.brbr- The Florida Keys are a notoriously difficult place to navigate.brbrbrbrThe Neighborhood:brbrWelcome to Lunara Bay!brbrNestled in a gated community less than a mile from Key West, Lunara Bay offers a family-friendly atmosphere with a local park just a short walk away—perfect for spending time with loved ones.brbrbrbrExplore & Dine Nearby:brbrEnjoy fresh seafood and local flavors at Hogfish Grill, Roostica, or Chico’s Cantina. Visit Hurricane Hole for happy hour and scenic waterfront views. Rent a boat for a day at Stock Rock Café or embark on a kayak tour with Lazy Dog.brbrbrbrBoating & Marina Access:brbrMany homes offer private boat docking or slips available at the onsite marina. A public boat ramp is conveniently located across the highway - Key Haven Boat Ramp.brbrbrbrNeed personalized recommendations Ask your GEM for their top things to do and places to go!brbrbrbrGetting Around:brbrTravel by car, boat, or plane to Palmgale House. The driveway allows parking for up to 2 vehicles and your boat trailer. brbrIf you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. brbrRent a golf cart, scooter or bikes for the day to enjoy the area. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Extend your stay 7+ nights for 10% off your entire stay!brbr- Elevate your stay and ask us about our Private Chauffeur services.brbr- Private washer/dryerbrbr- Located in gated communitybrbr- Free gym access at FYTbrbr- Fans inside bedrooms only operate with the light on.brbr- Pets are welcome! Our requirements are as follows: brbr•40lb maximum per petbrbr•$250/staybrbr•2 pet maximumbrbrbrbrInteraction with Guests:brbrYour dedicated GEM is at your service to answer any questions or curate unforgettable experiences tailored to your dreams in the Keys.

Palmgale Estate at Lunara Bay

Key West, Florida, United States

Bed

Bath

Sleeps

$1632.01

Summary:brbrThis elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West getaway. Tastefully decorated with trendy decor and modern furnishings, this property has a welcoming and clean feel. Comprised of two lofts on Duval, this recently renovated compound is perfect for up to 12 guests.brbrbrbrWith a private, shaded balcony overlooking Duval Street, this modern duplex is walking distance to all of Key West's best restaurants, attractions and galleries.brbrbrbrThe Space:brbrEach bedroom features a king size bed, while the living rooms have queen size Murphy beds for extra guests joining. brbrbrbrTwo bedrooms and 2.5 baths are located in the front unit, Sky Suite, while the other two bedrooms with en suite bathrooms are located in the back unit, Cloud Suite.brbrbrbrAccommodating up to 12 guests, this exceptionally large 4 bedroom/4.5 bath duplex comes with private laundry rooms and off-street parking for one vehicle.brbrbrbrThe bedrooms are furnished with classic cozy furniture and hotel grade sheets and pillows. The two full sized and fully stocked kitchens make cooking meals easy and convenient.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit.brbrbrbrHow to access: This property is a historic loft and can only be accessed by a flight of stairs. There is no elevator available.brbrbrbrThe Neighborhood:brbrOn the 700 block of Duval, The Sky Suites Retreat is centralized to everything Key West. brbrbrbrIn the heart of Duval street you can find many of locals favorite's such as: Martins, 915, 801 Bourbon Street Pub, Moondog Cafe & The Hemingway HousebrbrbrbrLooking for a night out Find Willy T's, Fogarty's and Fat Tuesday’s at the other end of Duval, but don’t worry there are pedicabs everywhere for easy transportation up and down Duval Street.brbrbrbrBeing in the heart of everything does come with noise of Duval street, but nonetheless an easy and convenient location to experience all Key West has to offer!brbrbrbrGetting Around:brbrParking Information: Off-street parking for 1 vehicle is included - please note it is tight and meant for smaller vehicles. For additional parking we are happy to provide you with nearby recommendations! brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr-Two private balconies (1 overlooking Duval, one private in the back of the duplex)brbr- Duplex is connected by and interior door.brbr- There are 2 stackable washer/dryers.brbr- This unit is not pet friendly.

Sky Suites Retreat - Balcony Overlooking Duval

Key West, Florida, United States

Bed

Bath

12

Sleeps

$424.86

UNMATCHED COASTAL ELEGANCE…brLocated in the impressive enclave of Casa Marina, your dreams of tropical opulence and supreme comfort coalesce in this Conch-style masterpiece. Indulge in 1600 sq. ft. of artfully designed living space, sure to dazzle the most discerning eye. The love is in the details as you feast your sights on unrivaled craftsmanship and decor, enfolded in lush landscaping and your own backyard oasis. When you're ready to venture out, ease into your sandals and enjoy perfect proximity to Key West's pristine beaches and the vibrant energy and excitement of Duval Street.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brStep inside to the expansive great room and dining area where hours of relaxed enjoyment await you. White wood walls and ceilings are lovingly bathed in natural light and the chef's kitchen is adorned with custom white shaker cabinetry, hand-crafted Zellige Moroccan tile backsplash, and top-tier Sub-Zero, Wolf and Bosch appliances. Wide-plank washed oak flooring and white travertine accents complete the backdrop of effortless and elegant living. A washer/dryer is located off the kitchen area. Live streaming on Hulu is available for binge watching all of your favorite shows! There is a Ring doorbell located on the front door of this home for security purposes. brbrSLEEPING ARRANGEMENTS…brThis beautiful abode features a primary king bedroom with a luxurious en-suite shower bathroom and a private door to the front porch. The 2 guest rooms offer a king bed and twin beds that can be converted to a king upon request and share a full shower bathroom.brbrOUTDOOR LIVING…brYour private tropical oasis greets you with its sparkling pool (comes heated in the cooler months and can be chilled in the warmer months upon request) with a tranquil water feature for a warm and inviting ambiance that soothes you into total bliss. Surrounded by verdant landscaping and premium Trex decking, a private outdoor shower completes the island lifestyle. Pet owners will enjoy the dedicated dog run and the property is fully enclosed with a custom picket fence for ultimate privacy. Enjoy 4 bikes to cruise around town and beach chairs for those wanting to dip their toes in the blue ocean water. brbrPARKING...brThere is off-street parking available at this home.brbrPETS...brThis home allows dogs only, but should refrain from being on home's furniture. Please include the size and breed when inquiring. 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).brbrYOUR SANCTUARY OF SOPHISTICATION…

THE GREEN COCONUT ~ Updated 3 BR, 2 Ba Home w/ Parking and Private Pool!

Key West, Florida, United States

3

Bed

Bath

6

Sleeps

$1261.31

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrTHE GILDED PINEAPPLE is a classic Key West home located on one of the most desirable streets in Old Town. This completely renovated, historic home gets its’ name from the elegant, oversized golden door knocker shaped like a pineapple that graces the front door – one of the many subtle touches that adds to the charm. THE GILDED PINEAPPLE features a welcoming front porch with rocking chairs and delicate gingerbread accents. The spacious backyard offers a private pool and is surrounded by lush, tropical foliage. Located just down the street from the historic seaport, you’ll be within walking distance to the best restaurants, shopping, and attractions Key West has to offer. Best of all, a month at THE GILDED PINEAPPLE includes Last Key Realty’s unrivaled Guest Services and Complimentary Concierge, known for providing treasured vacation experiences.brbrTHE LOCATION…brbrTHE GILDED PINEAPPLE is located on William Street, just down a couple blocks from both the historic seaport and World-Famous Duval Street. Situated on one of the best blocks in Old Town, this private home gives you the feeling of being away from it all yet is only a short stroll from everything that Old Town has to offer. Whether you’re looking to spend the day on Duval Street or watch the boats come and go at the seaport, you’ll be there in just a few minutes. You won’t need a car to get around from this location, but if you decide to bring one, there’s an off-street parking spot waiting for you in the driveway. There’s also a designated handicapped parking space right in front of the home on William Street.brbrTHE KITCHEN & LIVING AREA…brbrThe living area and kitchen are in the back of the house. The back French Doors allow natural light to flow in and open to the pool area. The living area features comfortable seating options for the whole group and a large flat screen TV to gather around for the big game or to binge watch your favorite show. The fully equipped kitchen features stainless steel appliances and every cooking tool needed to prepare meals at home. The indoor dining table comfortably seats six, and there’s additional seating at the kitchen bar. A convenient side door connects the driveway to the kitchen, making unloading groceries a breeze. There’s also a full bathroom off the kitchen that connects to the pool area.brbrTHE POOL AREA…brbrStep out the French Doors of the living area and kitchen into your private backyard oasis. The entire backyard is fenced in and landscaped for maximum privacy. The beautiful private pool can be utilized year-round thanks to the convenient heater/chiller that allows you to adjust the pool temperature to your liking. Relax on the sunny pool deck in the chaise lounges or hang in the shade under the umbrella while watching the outdoor TV. Treat your group to a poolside BBQ of today’s fresh catch using the propane Blackstone flat top grill and outdoor dining set with seating for six. Whether you are floating around the pool, preparing a meal on the grill, or toasting before a night out on the town, the pool area is certain to be a primary gathering place for your group.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom - Located on the Second Floor with a King bed, a flat screen TV, dedicated workspace, and an en-suite bathroom with two vanities, a walk-in shower, and a garden tub.brbr** Bedroom #2 – Located on the First Floor with a King bed, a flat screen TV, double closets, and direct access to the Jack-n-Jill bathroom with a shower and tub combo.brbr** Bedroom #3 – Located on the First Floor with Two Twins OR One King (you decide), a flat screen TV, a closet, and direct access to the Jack-n-Jill bathroom with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Lushly Landscaped Private Yardbr** Private Pool with Pool Heater & Chillerbr** Propane Blackstone Flat Top Grillbr** Outdoor TVbr** Off-street Parking in the DrivewaybrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 6 adultsbr** Pets Considered (Small Pets Only) - Max of 2 pets allowed and an additional fee of $200 per pet will apply

**THE GILDED PINEAPPLE @ THE SEAPORT** Gorgeous Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$894.13

Summary:brbrLocated right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Collins offers a central location to Key West’s main attractions and everything else the Southernmost city has to offer. With a balcony overlooking Duval Street you can be as much connected to or above the action as your whim desires.brbrbrbrThe Space:brbrThe downstairs bedroom features a king size bed, while the upstairs loft-style bedroom features 2 king size beds for ample sleeping space. There are also two pull out couches located in downstairs living room - allowing for up to 10 guests to reside here. brbrbrbrThis condo is fully equipped with a full kitchen, living room, dining area and balcony overlooking Duval Street. The kitchen contains a stove, refrigerator, and Keurig coffee machine. The bathroom has a full bathtub and shower. Enjoy central AC, smart TV's, ceiling fans and free wifi after a day on the town.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code 3 days prior to check-in to enter the unit.brbrbrbrHow to access: This property is a historic loft and can only be accessed by a flight of stairs. There is no elevator available.brbrbrbrThe Neighborhood:brbrOn the 500 block of Duval, The Collins is centralized to everything Key West. brbrIn the heart of Duval street you can find many of locals favorite's such as: Fausto's Food Market, Keys Coffee Co., and Cuban Coffee Queen, and tourist attractions such as: The Ernest Hemingway house, Mallory Square and Key West Lighthouse, all walking distance from your front door! brbrLooking for a night out, find Willy T's, Fogarty's and Fat Tuesday's within 1 block.brbrbrbrBeing in the heart of everything does come with noise of Duval street, but nonetheless an easy and convenient location to experience all Key West has to offer!brbrbrbrGetting Around:brbrParking Information: brbrThere is no on-site parking for this unit. We recommend dropping off belongings before parking overnight if you can not find street parking.brbrFor overnight parking here are some parking lots:brbr• Fleming Street Pay-to-Park Lot (This is Closest to you!)brbr• 204 Simonton Streetbrbr• Caroline Street Outdoor Parking Lotbrbr• Park N Ride Old Town GaragebrbrbrbrStreet parking information:brbr• There are pay-to-park spots and meters and it is free from 12AM - 8AM. With a 3 day limit.brbr• The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only” and visitors are NOT permitted to park in them.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrbrbrOther Things to Note:brbr- Private stackable washer & dryer. brbr- This unit is not pet friendly.

The Collins - On Duval Street

Key West, Florida, United States

Bed

Bath

Sleeps

$145.01

This property recently fully renovated. Original house was built in 1892. 1 bedroom 1 bathroom apartment with hardwood flooring, high ceilings, gourmet kitchen ,beautiful island decor and great porch located on the White Street.brJust few steps away from the best Cuban coffee shop in Key West and walking distance from beach.brApartment is fully furnished and have sleeper sofa in living room .brbrBedroom has queen size bed with memory foam mattress and fine linens.brbrThis apartment has washer and dryer in the unit.brbrThe health and safety of our guest is very important- current cleaning CDC guidelines has been implemented at our property.brCleaning service available weekly or bi-weekly on request.brbrMinimum stay is 28 days.brbr

Ocean-breeze Key West Cottage

Key West, Florida, United States

Bed

Bath

Sleeps

$821.13

Summary:brbrLocated right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This unique property offers a central location to Key West’s main attractions and everything else the Southernmost city has to offer. With a balcony overlooking Duval Street you can be as much apart or above the action as you desire.brbrbrbrThe Space:brbrThis apartment is equipped with a full kitchen, living room, dining area and balcony overlooking Duval Street. The kitchen contains a stove, refrigerator, and Keurig coffee machine. brbrbrbrThe downstairs bedroom features a king size bed, while the upstairs loft-style bedroom features 2 king sizes beds for ample sleeping space. There is also a pull out couch located in the downstairs living room for additional guests. The bathroom has a full bathtub and shower.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrOn the 500 block of Duval, Duval Loft is centralized to everything Key West. brbrbrbrIn the heart of Duval street you can find many of locals favorite's such as: Fausto's Food Market, Keys Coffee Co., and Cuban Coffee Queen, and tourist attractions such as: The Ernest Hemingway house, Mallory Square and Key West Lighthouse, all walking distance from your front door! brbrLooking for a night out, find Willy T's, Fogarty's and Fat Tuesday's within 1 block.brbrbrbrBeing in the heart of everything does come with noise of Duval street, but nonetheless an easy and convenient location to experience all Key West has to offer!brbrbrbrGetting Around:brbrThere are a variety of great ways to explore Key West including by bicycle, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrUnfortunately, there is no on-site parking for this unit. Feel free to ask us for parking recommendations.brbrbrbrOther Things to Note:brbr-This property is a historic loft and can only be accessed by a flight of stairs. There is no elevator available.brbr- No pets allowedbrbr- No parking is provided: we are happy to provide you with nearby recommendations!brbrbrbrLoft also Includes:brbr-Stackable Washer & Dryer brbr-A/Cbrbr-Ceiling Fansbrbr-Flat Screen TV’s in Living Room & Bedroomsbrbr-Fully Equipped Kitchen brbr-Linens and Towels providedbrbr-Free wireless high speed Internet

Duval Dream Loft - On Duval street

Key West, Florida, United States

Bed

Bath

Sleeps

$806.48

OVERVIEWbrThe Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, spacious, secluded and private. The cottage has a raised vaulted wood ceiling, creating a rustic, Caribbean ambiance. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double-hung sash. All linens and towels are furnished.brbrThe house has a Starlink secured high speed wi-fi network, streaming internet TV, and two (2) 32 Samsung SMART HDTVs. The house has central air conditioning, a ceiling fan, and a stacked LP washer and dryer. There is a Weber propane barbecue located on the pool deck.brbrThe cottage can comfortably accommodate a maximum of four (4) guests – who are comfortable sharing an open social living environment.brbrFIRST FLOORbrThe kitchen, living, dining, sitting, and bathroom and a small bedroom are located on the first floor. The living room has a queen sleeper sofa/ day bed and a 32 Samsung SMART HDTV. The bathroom, located off the living room, has been recently completely renovated and has a vaulted ceiling and a new full size marble walk-in shower. There is a full bed in the small bedroom at the end of the living room.brbrKITCHENbrThe kitchen is new and contemporary with mahogany cabinets, white Corian countertops, and integrated Corian sink, and serve thru access to the dining room. The ceiling is vaulted with architectural beams and LED lighting. The kitchen has a pantry, refrigerator, electric range, garbage disposal, microwave, and Braun coffee maker, Krupps toaster, dishes, flatware, glasses (service for 6), pots, pans, and all the basic cooking utensils. There is a French door providing access to the rear deck where the washer and dryer are located.brbrLOFT SLEEPING AREAbrA ship's ladder is used to access the loft sleeping area. The loft has a queen bed, and a 32 Samsung SMART HDTV.brbrCOMMON ELEMENTSbrThe five (5) house compound is private and secure with a 25' x 10' heated pool including a 5' x 10' heated Jacuzzi. In addition, there is a 10' x 8' heated Jacuzzi. There are brick walkways, and a 40' x 10' sun deck, including a stainless steel propane barbecue, chaise lounges for sunbathing and relaxing; and tables and chairs for dining. Throughout the property there is secured wireless internet access, and CCTV security monitoring. The design of the property lends itself perfectly for small gatherings with friends and family.brbrLANDSCAPINGbrThe landscaping is lush including various palm species, Poinciana, Spanish limes, avocado, bananas, hibiscus, bougainvillea, halliconias, bromeliads, and orchids, brick walkways. brbrEXCELLENT LOCATIONbrThe house is located in Old Town Key West at the corner of Thomas and Angela Streets - (2) blocks west of the center of Duval Street in one of the oldest sections of Key West; (4) blocks east of Fort Zachary Taylor State Park/Beach, the best beach and picnic area in Key West. The gated compound is within easy walking or biking distance to everything in Old Town Key West, Duval Street, and the best entertainment and dining on the island.brbrCHICKENS & ROOSTERSbrThe City of Key West protects chickens and roosters, and considers them as part of the history and charm of Key West. As a result, Key West and many of the islands throughout the Florida Keys have free-range chickens and roosters. You will definitely see and hear chickens and roosters during your stay in Key West. Some visitors to Key West love them, and some visitors hate them - personally, I enjoy them best roasted, with plantains, and black beans and rice!brbrCRITTERSbrAlso, please remember that you are in the tropics and most life forms typically thrive in the tropics. Please don' t be surprised or alarmed if you see a lizard, or an insect.

Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4

Key West, Florida, United States

Bed

Bath

Sleeps

$192.76

This two-bedroom Key West Writer's Cottage is a serene haven for creative minds and vacationers. It features a cozy living area with charming decor that inspires relaxation. Enjoy the relaxing deck for morning coffee or unwinding with a book and take a refreshing dip in the inviting pool. Each comfortably furnished bedroom ensures a restful night’s sleep, and the fully equipped kitchen is perfect for cooking. Plus, you can easily bike to the nearby boardwalk and beach for fun in the sun!

Cottage

Monthly Rentals Only - Key West Cottage Du Soleil

Key West, Florida, United States

Bed

Bath

Sleeps

$526.19

Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excitement of tropical adventures. This enchanting 3 bedroom, 3.5 bathroom monthly vacation rental offers a serene retreat amidst the vibrant atmosphere of the island, ensuring an unforgettable experience for you and your loved ones.brbrAs you enter this magnificent residence, you'll be captivated by the dramatic ceiling heights, elegant wood flooring, and designer accents that exude sophistication and coastal elegance. The open-concept gourmet kitchen invites you to indulge in Key West's culinary delights, featuring a 48 gas range, an expansive island with seating, quartz countertops, stainless steel appliances, and a wine chiller. The telescoping door wall connects the indoor dining area to the outdoor seating, creating the perfect ambiance for memorable meals and tropical libations.brbrFor entertaining purposes, the residence offers comfortable seating arrangements that cater to socializing and dining. brIn addition to the living room, there is a separate dining room that accommodates up to six people. Furthermore, the kitchen is equipped with an island that offers additional seating for up to four people.brbrThe primary suite, situated on the first level, provides a tranquil retreat for relaxation and rest. It features a spacious king-size bed, ensuring a comfortable and luxurious sleeping experience. Within the master suite, you'll find the ensuite, a private bathroom attached exclusively to the primary bedroom. The ensuite is designed to enhance your indulgence and rejuvenation. It boasts a large soaker tub, inviting you to immerse yourself in a soothing bath or enjoy a sizable walk-in shower. brbrOn the second floor of the residence, you will find two additional guest bedrooms, each equipped with a king-size bed and ensuite bathrooms with showers. These guest bedrooms are designed to provide a comfortable and private space for your family and friends during their stay.brMoreover, the second floor also features a bonus space, dedicated to providing a comfortable area for family and friends to relax and unwind.brbrStep outside to your private oasis, where the lush landscaping and gentle sounds of the waterfall create a soothing backdrop for leisurely afternoons by the heated pool. The composite decking offers an inviting space for sunbathing, lounging poolside, or enjoying the island breeze.brbrNestled on a peaceful street just a short stroll from Duval Street and the Historic Seaport, you'll be ideally positioned to explore Key West's famous attractions, delightful shops, world-class dining, and vibrant nightlife. With its walkable and bike-friendly location, your island adventures are just steps away from your luxurious retreat.brbrImmerse yourself in the enchanting atmosphere of Key West and create lasting memories with your loved ones at this stunning vacation rental. From its exquisite design and modern amenities to its unbeatable location, your unforgettable island getaway awaits. Book your stay at this luxurious Key West oasis today.brbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.

Ashe St Serenade - A Luxury Island Oasis - 3BD/3.5Bath - Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$930.4

Summary:brJust 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.brbrThe Space:brThis Key West cottage boasts 2 bedrooms, 1 bathroom, a fully outfitted kitchen, a cozy outdoor dining area, a living room with tons of seating, a private sundeck, and a historic Conch porch for people watching. brbrThis home is complete with an easy to use push button lock, cool air conditioning, smart TVs, and comfortable furnishings. brbrWe have done our best to anticipate your needs. The living room and the all two bedrooms have Smart HDTV with Hulu. And, a private washer and dryer are provided for your use.brbrThe recently updated kitchen is fully stocked with pots, pans, plates, utensils and glassware. A bar that seats two makes cooking and visiting a breeze. An outdoor table is perfect for sharing meals. Most importantly, we also provide coffee and a Keurig.brbrThe living room offers seating for your whole party and a queen sleeper sofa.brbrTwo bedrooms for you...br* the downstairs bedroom is complete with a queen mattress and is steps away from the bathroom.brbr*second bedroom, located upstairs, has a king bed, a lot of storage, and access to the sundeck.brbrThere is one parking spot provided on the driveway. Additional paid street and lot parking is available within walking distance. brbrThis central location puts a short walk or bike ride to all of Key West's most loved place...brbrCrawling distance from Duvalbr300 feet to the Key West Lighthousebr500 feet to Hemingway Homebr.4 miles to the Southernmost Pointbr.4 miles to the Key West Butterfly and Nature Conservationbr.7 miles to Sloppy Joe'sbr.9 miles to Mallory Squarebr3.7 miles to the airportbrbrGuest Access:brGuests will have access to the entire home and outdoor spaces.brbrThe Neighborhood:brNestled in the heart of Old Town, this quintessential Key West cottage puts you right where the island buzzes—just half a block from iconic Duval Street. Walk to everything: sunset sails, mojito bars, seafood shacks, boutique shops, and world-famous landmarks. You're quite literally Hemingway’s neighbor, and if you head up to the second-story sundeck, you might even catch a glimpse of the lighthouse peeking through the palms. This is true Key West living—laid-back, walkable, and unforgettable.brbrGetting Around:brWith a central location like this you can walk, bike, scooter, drive, or Uber to all of what Key West has to offer.brbrOther Things to Note:brThis property can be reserved with the neighboring cottage to accommodate larger groups of up to 16 guests.brbrThis unit is pet-friendly. 40lb maximum per pet. $40/night per pet 2 pet maxbrPlease let us know if you plan on bringing your pet. See rules for details.brbrNo smoking inside the home.brbrSorry, no early check-in. We need time to make it perfect for your stay!brbrInteraction with Guests:brWe are available if you need assistance during your stay.

Steps to Duval •Hot tub • Sleeps 6

Key West, Florida, United States

Bed

Bath

Sleeps

$254.75

Welcome to Bahama Dreams, a fully renovated 3 bedroom/ 2 bath eyebrow style home just two blocks off iconic Duval Street which offers the best in entertainment, attractions, restaurants, shopping and more. This historic Bahama Village house is part of an enclave of three homes surrounding a shared pool. It is strolling distance to historic Fort Zachary Taylor Beach, Truman Waterfront Park, the Hemingway Home and Lighthouse Museums, and everything old town has to offer.brbrFeatures include high-speed wireless, flat screen TVs, a fully equipped kitchen, laundry, one off-street parking space and more.brbrLiving Spaces:brRelax in this tranquil living room decorated with cool tropical colors and neutral furnishings to create the serene atmosphere. The fully equipped kitchen sits just off the living room which opens to your outdoor living and dining area. French doors open to your private back covered deck overlooking the shared pool and deck area.brbrOutdoor space:brEnjoy dining on your own covered deck that overlooks the shared pool area. All enclave guests are welcome to enjoy the pool and shared deck space, while being mindful of the close proximity to the other homes in the compound. In addition to the back deck, the front porch is the perfect spot for morning coffee or for refreshing afternoon beverages.brbrSleeping Accommodations:brTwo of the home’s three bedrooms are off the front entry hallway. One has a king bed and the other has two twins that can be made into a king. The large main floor bathroom that also houses the laundry area is down the short hallway next to the kitchen. brbrThe second floor has an open loft-style bedroom and bathroom. There is a comfortable king bed on one side of the space, with the bathroom occupying the other. The bathroom features a claw-foot soaking tub, but there isn't a standup shower on this level of the home.brbrParking:brThere is one off street parking spot for a small to medium sized vehicle. Like most areas of Key West, there is limited street parking as many of the spaces are reserved for full-time residents of Key West.brbrBedding: 2 kings, 2 twins

Coastal Inspired Cottage in Bahama Village Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$398.18

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSpanning an exclusive corner lot in the desirable Mid Town neighborhood of Key West is a stunning compound-style home designed as the ultimate vacation destination for a family or group of friends seeking privacy and quiet only a short bike ride or walk from the bustling downtown Old Town area of Key West. brbrIn addition to four spacious bedrooms, this property offers:brbr- Private Heated Poolbr- Indoor & Outdoor Dining and Lounge Areasbr- Plenty of Parkingbr- Ranch-Style One Story LayoutbrbrYour rental includes Last Key Realty’s renowned Five-Star Guest Services, known for making memorable Key West stays and adding true hospitality to your vacation rental experience. For a month or more in paradise, enjoy the ideal Keys vacation home experience in MIDTOWN MOSAIC.brbrTHE LOCATION...brbrMIDTOWN MOSAIC is located in a quiet residential area 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 of its attractions.brbrTHE LIVING AREA AND KITCHEN...brbrThe open plan living area of MIDTOWN MOSAIC is perfect for the whole gang to gather and enjoy time together. The wall of glass Euro doors provide an unobstructed view of your outdoor oasis and can be completely opened to create a seamless indoor/outdoor living space. The living room has a large sofa and chairs to stretch out on, with a large flat screen SMART TV. The galley-style kitchen is fully equipped with stainless steel appliances, including a gas range, and all of the tools and equipment you will need to prepare a gourmet meal. There is bar seating for a casual bite, and a cozy dining banquette just off the kitchen.brbrTHE POOL AREA AND PERGOLA...brbrWhile the upscale interior is designed for a perfect relaxing retreat, your private pool area surrounded by lush landscaping will provide hours of enjoyment year-round.brThe pool area is your very own exotic retreat, surrounded by gorgeous tropical landscaping and fully fenced for maximum privacy. There is plenty of space for your group to enjoy both the sunshine and the shade. Surrounded by chaise lounges, the heated pool gets lots of sun throughout the day and features a distinctive mosaic waterfall wall. There is a large dining table with seating for 8, an outdoor sectional sofa, and propane BBQ grill under the pergola.brbrTHE ACCOMMODATIONS...brbr• First Master Suite: Located in the Main House with a Queen bed and an en-suite bathroom with double sinks and a walk-in shower with mosaic art, a signature feature of this home.brbr• Second Bedroom: Located in the Main House with a Two Twins OR One King, direct access to the outdoor side porch, and shares the hall bathroom with a shower and tub combination. brbr• Third Bedroom: Located in the Main House with a Queen bed and shares the hall bathroom with a shower and tub combination. brbr• Second Master Suite: Separate Guest House with Two Twins OR One King bed, a kitchenette, a private paved patio, a private dining nook with bistro set, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen SMART TVs in Living Room and All Bedroomsbr• Fully Equipped Kitchenbr• Basic stock of spicesbr• Starter supply of paper productsbr• Starter set of cleaning productsbr• Linens and Towels providedbr• Wireless high-speed Internet access and full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Fully Fenced and Lushly Landscaped Private Yard br• Private Heated Poolbr• Off-Street Parking in Driveway & Plenty of Parking On Street Around Homebr• Propane BBQ GrillbrbrOther 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• Max of 2 Pets Allowed with Additional Fee of $200 per pet

**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$271.69

Summary:brbr2 bed/2.5 bath townhouse on golf course with shared pool minutes away from downtown Key West, local beachesbrbrbrbrThe Space:brbrIndulge in the ultimate getaway experience with our stunning 2 bedroom, 2 1/2 bathroom townhouse nestled on the picturesque Key West Golf Course. Overlooking the lush #1 green, this oasis offers unparalleled tranquility and relaxation. Step outside and immerse yourself in luxury at our lagoon-shaped pool featuring a soothing waterfall - just a few steps away from your doorstep. Unwind in the extended rear yard adorned with vibrant grass and tropical landscaping, creating a serene backdrop for your vacation. Inside, discover a haven of comfort and style. The spacious living room opens up to a screened veranda, perfect for expanding your entertaining space while basking in streams of natural sunlight. A convenient downstairs powder room adds to the convenience of your stay. Upstairs, each bedroom boasts its own private bathroom en suite, providing the utmost privacy and comfort for you and your guests. Experience the epitome of Key West living at our vacation rental - book your stay today and start making memories that last a lifetime. The Key West Golf Club HOA is a gated community offers safe and beautiful paths to run, walk and play. Staying here also gives you parking for 2 vehicles. Prime Tee Haven, is located at Mile Marker 5 of US 1 and is 1 block from the Key West Hospital, Police Department, Community College and Tennessee Williams Theater. It is about 5 miles from door to door to downtown Key West. This is a pet & smoke free property.

Condo

Prime Tee Haven | Townhouse on golf course

Key West, Florida, United States

Bed

Bath

Sleeps

$217.95

VanGogh Studio | Updated, Old Town, Heated PoolbrbrStep into the heart of Key West at The Galleria, a charming studio just blocks from the iconic Duval Street. Once a haven for traveling artists, this unique space has been transformed into a peaceful escape where guests can unwind, recharge, and soak in the island's creative energy. Whether you're here for relaxation, exploration, or both, The Galleria offers the perfect setting for your Key West adventure.brbrThe Ambiance:brDesigned for those who appreciate simplicity and comfort, this well-appointed studio features everything you need for a relaxed stay. The kitchenette comes equipped with a microwave, mini fridge, and Keurig coffee maker, ideal for preparing quick meals or enjoying a morning coffee before heading out. Unwind after a day of sightseeing with cable TV or stay connected with complimentary WiFi. This studio is perfect for solo travelers or couples looking for a stylish and convenient place to stay.brbrGuest Access:brEnjoy a seamless check-in process with our contactless system. Upon booking, you'll receive two access codes—one for the hallway and another for the studio—ensuring a smooth arrival. Guests have access to a range of on-site amenities, including a heated pool, sundeck, bike rack, and gas grill, perfect for a relaxing day in the sun. There's also a shared laundry facility located next to the pool for your convenience.brbrThe Neighborhood:brLocated in the vibrant Bahama Village, this studio places you in one of Key West's most eclectic neighborhoods, just a short stroll from the world-famous Duval Street. Explore the Southernmost Point, the Ernest Hemingway Home, and the Key West Butterfly Conservatory, all within walking distance. Bahama Village is also home to some of the best local dining spots, including Blue Heaven and Santiago's Bodega where you can indulge in wonderful island-inspired cuisine. Whether you're here for history, culture, or nightlife, you'll find everything within easy reach.brbrGetting Around:brWhile The Galleria does not offer on-site parking, free street parking is available on a first-come, first-served basis directly in front of the complex. Key West is an incredibly walkable destination, with many attractions just minutes away. For those who prefer alternative transportation, bikes, scooters, and golf carts are popular ways to get around, and Uber, Lyft, and local taxis are also available. Need help with getting around We're happy to provide local recommendations!brbrOther Things to Note:br- Please keep in mind that this unit is cozy and may feel small for some guests, but it offers everything you need for a comfortable stay - 144sqftbr- A shared washer/dryer is available on the first floor, next to the pool area.br- Pets are welcome! We allow one dog, with a 40lb weight limit per pet, for a fee of $20 per pet per night.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, driveways, pool, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

VanGogh Studio | Updated, Old Town, Heated Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$321.61

Little Palm is a Cigar Barons shotgun with all the ambience of the shabby chic artists villa. It is immersed in cuban gardens and brick pathways. It's like stepping into Jimmy Buffetts Margaritaville. Out on the deck you will watch the stars, sip your margarita and swim in the pool with the waterfall cascading down around you. Just 2 blocks from Duval Street and all the historic treasures of old town key west. It has all the amenities you expect in a 5 star experience.brbrGuest suite is spacious with king size bed, full kitchen, dishwasher, refrigerator, stove, microwave, Keurig coffee maker, toaster, blender and more. Fully renovated bathroom with shower. Deluxe bamboo furniture accented with Dade county pine walls. Original artwork depicting Jimmy Buffett's era.brbrEach cottage is accessed through the private gardens of this gated compound.brbrA neighborhood convenience store is just across the street. Neighborhood cuban and coffee shop only blocks away.

Pool, Laundry, and grilling area

Key West, Florida, United States

Bed

Bath

Sleeps

$952.89

Upscale historic cigar barons mansion in walking distance to everything you desire in Key West. 3 spacious 1Br’s with outdoor living at its finest. Each guest suite has its own separate entrance to the gardens. pool, sitting areas, BBQ, 2 off street parking spaces, free laundry and Wi-Fi.brbrThe guest cottage has two units with full kitchens dining room nooks, office desk, king-size beds, updated large showers, living room areas, updated mini split AC, TV and WiFi. Alhambra has a large Florida room with AC, mini fridge, microwave, and TV with WiFi. Queen size bed with heated Jacuzzi tub and shower.brbrAll guests share the courtyard/gardens area, pool, barbecue area, laundry room, and outdoor sitting areas in the garden. brbrGuests will be met upon arrival within reasonable check in times. Host will be available on Airbnb or via text during your stay.brbrA neighborhood convenience store is located across the street from the property.brbrMost of our guests either walk or rent bikes to navigate the streets of Key West. Golf carts also have been a favorite by some and can be parked in one of the two available parking spots.brbrA neighborhood convenience store is located across the street from the property. A neighborhood cuban coffee shop is only blocks away.

Hotel

Pool, Laundry, and grilling area

Key West, Florida, United States

Bed

Bath

Sleeps

$313.81

Keep it simple at this peaceful and centrally-located place.brbrCayo Hueso has the ambience of a captains quarters on a sailing vessel. The master bedroom has a king size bed . The kitchen is a galley style with dishwasher and beautifully crafted wooden kitchen counters. The bathroom has a tall wooden counter with sink and a large shower. The living space is cozy with a small couch, dining nook, and a t.v cabinet with desk.

Pool, laundry, and grilling area

Key West, Florida, United States

Bed

Bath