Vacation Rentals By Owner In Key West, FL

Key West Wabi Sabi is a quintessential 1930s cottage that embodies the beauty and simplicity of island-life charm. If you’re looking to be in the heart of Old Town yet want your own pool and parking space, 506 Bahama is a perfect choice for your trip. You’ll be right off Duval Street, directly across from Fausto’s Food Palace for groceries and necessities, but tucked away enough for that real vacation recharge. This thoughtfully renovated retreat preserves the home’s original character and vintage Key West vibe while embracing an ideal indoor-outdoor feel. The open-concept great room and kitchen lead seamlessly to a private deck and pool framed by happy foliage and a hand-painted mural. Our guests love making Key West memories here and often rebook Key West Wabi Sabi.brbrThe home offers four bedrooms and sleeps up to 8 people. Each room has its own vibe: a lofted master suite with a king-sized bed, a vintage vanity, a split unit A/C and full bathroom; another large downstairs room with a comfy king bed and full bath; a cozy third bedroom with a trundle bed and a half bath; and a fourth bedroom with another king bed and its own bathroom. The cottage is great for gathering yet offers enough private space for everyone to find their own mid-vacation reprieve if needed.brbr506 Bahama is a fantastic homebase as you explore the best of Key West. It’s a lovely blend of ease, simplicity, and island charm. Again, the location and thus the walkability of this home really can’t be beat if you’re looking to make the most of the general Duval Street excitement! Come home from an afternoon out and about to enjoy your personal pool with plenty of lounge space, or relax on your classic Key West front porch. We look forward to hosting you and making sure your stay at Key West Wabi Sabi is one you’ll love.brLove the location but need different accommodations See if our neighboring properties Down Island Digs or Pavillion Villa have what you’re looking for! brbrRestrictions: Smoke free house. No pets. This home is offered as an exclusive vacation rental in the most requested location in Key West. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.

Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval

Key West, Florida, United States

4

Bed

3

Bath

8

Sleeps

$276.03

A WORLD APART FROM REALITY...brIndulge in this tropical retreat that possesses all the desirable amenities to make the most of your island escape. The classic and adults only Azul Queen Anne mansion which was built in 1899 by shipwrights and carpenters for one of the island's premier cigar barons will immerse you into a fun loving blend of old world charm and carefree island living. A contactless check in/out process with a virtual innkeeper allows for a seamless experience!br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brTake advantage of these captivating surroundings and unwind on the front porch as you appreciate the million dollar views. Order delivery at one of your island favorites and enjoy within one of lovely, newly renovated gathering spaces or under the outdoor shaded seating area. The mansion rooms provide beautiful spaces for sitting, dining and relaxing for all of our guests to enjoy. A kitchen is located on the first level of the mansion which also includes a microwave and additional refrigerator space.brbrSLEEPING ARRANGEMENTS...brLocated off the 2nd floor balcony, your private king room with ensuite bath awaits with cozy linens to welcome you in after a fun afternoon. A flat screen TV, Keurig coffee maker and mini fridge add to the comfort of your island sabbatical. A table with 2 chairs outside your room allows you to enjoy the outdoor beauty without having to go too far.brbrOUTDOOR LIVING...brIndulge in the welcomed island breezes and a good novel as you catch some rays on the 2nd floor sundeck just outside your room. Take a refreshing dip in the pool below surrounded by tropical vegetation and slip into town for all the action on the infamous Duval St. Off street parking is provided on a first come first serve basis. brbrPARKING...brIt is first come first serve and if there is not a space available upon arrival you may park on the street in front for free (do not park in a residential permit space!) until one becomes available, or even for the length of your stay.brbrBEACHES...brSimonton Beach is 1.1 milesbrFort Zachary Taylor Beach is 1.5 milesbrSouth Beach is 0.7 milesbrHiggs Beach is 0.7 milesbrSmathers Beach is 2.1 milesbrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrLIVE THE SIMPLE LIFE...

CLARO ~ Adults Only, Pool View King Room in Azul Mansion!

Key West, Florida, United States

Bed

Bath

Sleeps

$274.12

PERFECT RECIPE FOR RELAXATION...brMake the most of your island sabbatical within the exquisite and adults only Azul Queen Anne mansion built in 1899 by shipwrights and carpenters for one of the island's premier cigar barons. A tasteful blend of coastal design boasting historic elements draw you back in time. Centrally located within this beloved town, you are just minutes to all the Duval St. fun, yet far enough away for a peaceful night's rest. A contactless check in/out process with a virtual innkeeper allows for a seamless experience!br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brSerene surroundings will help wash your worries away allowing you to fully appreciate peaceful island vibes. Sip your morning cup of coffee on the mansion's front porch as you watch people passing by. Order delivery at one of your island favorites and enjoy within one of lovely, newly renovated gathering spaces or under the outdoor shaded seating area. The mansion rooms provide beautiful spaces for sitting, dining and relaxing for all of our guests to enjoy. A kitchen is located on the main level of the mansion which also includes a microwave and additional refrigerator space.br***GUESTS MUST BE 25 YEARS OF AGE OR OLDERbrbrSLEEPING ARRANGEMENTS...brFind your sleeping arrangements on the 2nd level of the mansion overlooking the sparking pool below. A queen room with a flat screen TV, Keurig coffee maker, mini fridge and ensuite private full bathroom with a shower add to the comfort of your island home. A table with 2 chairs sit just outside your room making outdoor living easy to achieve.brbrOUTDOOR LIVING...brSun lovers will cherish the breezy 2nd floor sundeck with vibrant landscape in the distance calling for a good book. Swim until your heart's content in the shimmering pool below and hop into town only a short distance away. Off street parking is available on a first come first serve basis. brbrPARKING...brIt is first come first serve and if there is not a space available upon arrival you may park on the street in front for free (do not park in a residential permit space!) until one becomes available, or even for the length of your stay.brbrBEACHES...brSimonton Beach is 1.1 milesbrFort Zachary Taylor Beach is 1.5 milesbrSouth Beach is 0.7 milesbrHiggs Beach is 0.7 milesbrSmathers Beach is 2.1 milesbrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrTIME TO DISCONNECT...

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Key West, Florida, United States

Bed

Bath

Sleeps

$277.98

RELAX, UNWIND & ESCAPE...brImmerse yourself within the charming, adults only Azul Queen Anne mansion built in 1899 by shipwrights and carpenters for one of the island's premier cigar barons. A tranquil and lush setting with a central location in Old Town Key West, these unique accommodations are sure to pull you into an unmatched experience a world apart from reality. A contactless check in/out process with a virtual innkeeper allows for a seamless experience!br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brYour serenity begins as you step foot on the charming grounds of this generous and vibrant estate. A blend of coastal decor among rich, historic elements captivate your island soul. Take a break from reality out on the front porch as you soak up million dollar views. Order delivery at one of your island favorites and enjoy within one of lovely, newly renovated gathering spaces or under the outdoor shaded seating area. The mansion rooms provide beautiful spaces for sitting, dining and relaxing for all of our guests to enjoy. A kitchen is located on the main level of the mansion which includes a microwave and additional refrigerator space. brbrSLEEPING ARRANGEMENTS...brA cozy king bed occupies this unit within the mansion with a private en suite full bathroom with a shower. Enjoy a flat screen TV for lazy evenings together. A Keurig coffee maker and mini fridge are provided as added comfort in your home away from home. brbrOUTDOOR LIVING...brThe perk of off street parking is provided on a first come first serve basis. Open the back door from your suite to a peaceful front balcony where you can soak up your tranquil surroundings (one other guest room has access to this balcony). Steps away from your room is a 2nd floor sundeck with endless lush views and an island breeze that overlook a sparking, shared pool. Cherish your well deserved R & R, then slip into town to visit all the adored tourist attractions.brbrPARKING...brIt is first come first serve and if there is not a space available upon arrival you may park on the street in front for free (do not park in a residential permit space!) until one becomes available, or even for the length of your stay.brbrBEACHES...brSimonton Beach is 1.1 milesbrFort Zachary Taylor Beach is 1.5 milesbrSouth Beach is 0.7 milesbrHiggs Beach is 0.7 milesbrSmathers Beach is 2.1 milesbrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrNO BETTER TIME THAN NOW...

CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

Key West, Florida, United States

Bed

Bath

Sleeps

$278.95

ISLAND SANCTUARY...brThe grand and adults only Azul Queen Anne mansion awaits the creation of your tropical sabbatical within the Old Town district. At first glance you will observe impressive craftsmanship which was built in 1899 by shipwrights and carpenters for one of the island's premier cigar barons. A contactless check in/out process with a virtual innkeeper allows for a seamless experience! br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brPossessing old world charm with modern luxuries, this gem will have you feeling lost on island time. Coastal inspired décor among a rich, historic setting draw you into a memorable Key West experience. Sip your morning cup of coffee on the mansion's front porch and marvel over the serene surroundings. Order delivery at one of your island favorites and enjoy within one of lovely, newly renovated gathering spaces or under the outdoor shaded seating area. The mansion rooms provide beautiful spaces for sitting, dining and relaxing for all of our guests to enjoy. A kitchen is located on the first level of the mansion which also includes a microwave and additional refrigerator space.brbrSLEEPING ARRANGEMENTS...brLocated on the 2nd floor of the main house, your comfortable king room welcomes you in. Cozy linens add to a peaceful night's rest accompanied by a flat screen TV, mini fridge and Keurig coffee maker, as well as a private ensuite full bathroom with shower. brbrOUTDOOR LIVING...brOpen the back door from your suite to a front balcony offering another lounging space to listen to the breeze coming through the palm leaves (one other room has access to the balcony). From the rear of the main house you will step out to a bright and breezy 2nd floor sun deck with vibrant garden views for your afternoon R & R. The shimmering pool below will refresh your senses with plenty of surrounding loungers. Head into town for happy hour by foot or bicycle ride or take a scenic drive as off street parking is available on a first come first serve basis. brbrPARKING...brIt is first come first serve and if there is not a space available upon arrival you may park on the street in front for free (do not park in a residential permit space!) until one becomes available, or even for the length of your stay.brbrBEACHES...brSimonton Beach is 1.1 milesbrFort Zachary Taylor Beach is 1.5 milesbrSouth Beach is 0.7 milesbrHiggs Beach is 0.7 milesbrSmathers Beach is 2.1 milesbrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrSTART CREATING YOUR ISLAND MEMORIES...

CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!

Key West, Florida, United States

Bed

Bath

Sleeps

$284.68

**This accommodation lies up a set of narrow, spiral stairs to a gorgeous room with dramatic, dormered ceilings within the room and shower area. Please let us know if you have any concerns on the stairs or height of the ceilings as your comfort is our priority. brbrTREETOP VIEWS...brSpend your tropical retreat within the historic, adults only Azul Queen Anne mansion ready to capture your island spirit. Built in 1899 by shipwrights and carpenters for one of the island's premier cigar barons, this prestigious masterpiece lures you back in time to an uncharted experience. A peaceful location just minutes to town, this hideout possesses all that your heart could desire while on Key West time. A contactless check in/out process with a virtual innkeeper allows for a seamless experience!br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brOld world charm with modern luxury perks create a blissful experience for your island escape. Enjoy people watching out on the mansion's front porch and soak up the serene surroundings. Order delivery at one of your island favorites and enjoy within one of lovely, newly renovated gathering spaces or under the outdoor shaded seating area. The mansion rooms provide beautiful spaces for sitting, dining and relaxing for all of our guests to enjoy. A kitchen is located on the first level of the mansion which also includes a microwave and additional refrigerator space. brbrSLEEPING ARRANGEMENTS...brThis romantic getaway is located on the 3rd story of the mansion above a set of spiral staircases. Find your well awaited, intimate suite with a unique design of dramatic, dormered ceilings within this charming attic space. A private balcony boasts breathtaking views of the pool and surrounding beauty. A king bed with cozy linens call your name with a flat screen TV, Keurig coffee maker and mini fridge nearby. A PRIVATE ensuite full bathroom with a shower is featured, also showcasing steeping slopes. This room is equipped with a cozy sofa sleeper and a writing table for those journaling their Key West story. brbrOUTDOOR LIVING...brConvenient off street parking is provided on a first come first serve basis even though you are located just a short walk or bike ride to everything on Duval St. Catch some rays out on the breezy 2nd floor sun deck with plenty of loungers overlooking the shimmering, shared pool below.brbrPARKING...brIt is first come first serve and if there is not a space available upon arrival you may park on the street in front for free (do not park in a residential permit space!) until one becomes available, or even for the length of your stay.brbrBEACHES...brSimonton Beach is 1.1 milesbrFort Zachary Taylor Beach is 1.5 milesbrSouth Beach is 0.7 milesbrHiggs Beach is 0.7 milesbrSmathers Beach is 2.1 milesbrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrESCAPE REALITY...

ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!

Key West, Florida, United States

Bed

Bath

Sleeps

$389.38

A DREAMY ESCAPE...brCreate your very own Key West story within the captivating, adults only Azul Queen Anne mansion which was built in 1899 by shipwrights and carpenters for one of the island's premier cigar barons. Boasting tranquil surroundings with convenience to all the action on Duval St. these accommodations are sure to impress on your unique island journey. A contactless check in/out process with a virtual innkeeper allows for a seamless experience!br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.br***There is no complimentary breakfast however we provide light snacks for your enjoyment in the common areas. brbrDETAILS AND AMENITIES...brMarvel over the rich, historic charm blended with coastal inspired decor among the enchanting mansion. Sip your morning cup of coffee on the mansion's front porch and appreciate the colorful views all around. Order delivery at one of your island favorites and enjoy within one of lovely, newly renovated gathering spaces or under the outdoor shaded seating area. The mansion rooms provide beautiful spaces for sitting, dining and relaxing for all of our guests to enjoy. A kitchen is located on the main level of the mansion which also includes a microwave and additional refrigerator space.brbrSLEEPING ARRANGEMENTS...brLocated up on the 2nd floor balcony, our spacious king suite comes equipped with a flat screen TV, mini fridge, Keurig coffee maker and an ensuite full bathroom with a shower. Open a set of French doors from your room to a bright, breezy sundeck with plenty of loungers for soaking up the blissful island weather. A table with 2 chairs sits just outside your room so you can enjoy the serene surroundings before getting ready for the day!brbrOUTDOOR LIVING...brTake advantage of the prime location by strolling into town at your convenience after you've had plenty of time to unwind by the shimmering, shared pool. brbrPARKING...brIt is first come first serve and if there is not a space available upon arrival you may park on the street in front for free (do not park in a residential permit space!) until one becomes available, or even for the length of your stay.brbrBEACHES...brSimonton Beach is 1.1 milesbrFort Zachary Taylor Beach is 1.5 milesbrSouth Beach is 0.7 milesbrHiggs Beach is 0.7 milesbrSmathers Beach is 2.1 milesbrbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrTIME TO UNWIND...

FUENTE ~ Adults Only, 2nd Level Pool View King Room at Azul Mansion!

Key West, Florida, United States

Bed

Bath

Sleeps

$574.13

The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Condo in Truman AnnexbrbrWelcome to your sunny escape in paradise! Nestled in the charming and secure Shipyard Condominium community—part of the iconic Truman Annex in Old Town Key West—this two-bedroom, two-bath, two-story condo blends island comfort with unbeatable location.brbrStep inside and feel instantly at home. The living room is spacious and inviting, with cozy furnishings, a dedicated work area, and a sleeper sofa for extra guests. Sunlight pours through the glass doors, which open onto a private outdoor deck surrounded by lush tropical foliage. Whether you're sipping morning coffee or enjoying a meal at the outdoor dining set for four, you'll love the relaxing Key West vibes.brbrThe compact kitchen is thoughtfully equipped with everything you need for your stay—stove, refrigerator with ice maker, dishwasher, and more. A breakfast bar and dining table provide seating for four, perfect for casual meals before heading out to explore.brbrDownstairs, you’ll find a convenient bedroom with a Smart TV and sleeper sofa, ideal for kids or guests. Upstairs, the entire second floor is a peaceful retreat featuring two queen-size beds, a full bathroom, and another Smart TV.brbrThis condo comes with all the extras to make your stay easy and carefree: in-unit washer and dryer, front porch with comfortable seating for people-watching, and an assigned parking spot located right outside your door for effortless arrival and unpacking.brbrWhen it’s time to explore, you’re just a short stroll from the famous Duval Street—home to five-star dining, eclectic shops, vibrant art galleries, and world-class entertainment. The stunning Fort Zachary Taylor State Park is also nearby, offering a beach, shaded picnic areas, and grills for a perfect day by the sea. Little ones will love the Truman Annex splash pad and playground, and everyone can enjoy the Shipyard’s own heated pool and sun loungers.brbrWhether you're here for adventure, relaxation, or a little bit of both, this beautifully maintained condo offers the perfect launchpad for your Key West getaway.brbrBook your stay today and let the island life welcome you home.

The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Complex

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, have central air conditioning, off street parking, and pool access. This Shipyard home is a single level condominium on the 2nd floor with balconies. This property also has an awning for coverage from the sun. brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Tropical Breezes at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

4

Sleeps

$488.81

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrA home designed to impress the most discerning travelers, LAYOVER in PARADISE is an oasis of comfort and superlative amenities sure to meet the expectations of those accustomed to first class treatment. LAYOVER in PARADISE is a brand newly constructed exquisite private home in the Casa Marina neighborhood that offers three spacious private suites, each with a large en-suite bathroom, ample closet space, and a flat screen TV - and that's just the beginning! In addition to an ideal bedroom configuration, this home also features:brbr• Tropical Backyard with a Private Heated Poolbrbr• Open Living Areabrbr• Fully Equipped Gourmet Kitchenbrbr• Off-street Covered Parkingbrbr• Ideal LocationbrbrThis home may be rented exclusively through Last Key Realty and includes our Five Star Guest Services, which is notorious for providing memorable vacations. Whether Key West is a vacation destination for you or turns into a permanent landing spot, your stay at LAYOVER in PARADISE is sure to be one you'll never forget!brbrTHE LOCATION...brbrThe Casa Marina district of Old Town Key West is one of the prime residential neighborhoods on the island. Just one block from the Casa Marina resort and beaches, LAYOVER in PARADISE offers the perfect balance of a quiet escape from the hustle and bustle of Old Town while only being a short walk to Key West's best attractions. You'll be right around the corner from famous local restaurants like Louie's Backyard and Salute on the Beach, and only a few short blocks from the action at upper Duval Street. Located just across the street from the famous Casa Marina hotel, this home is situated amongst million-dollar residential homes in what is arguably the most desirable neighborhood in Key West.brbrTHE LIVING AREA and KITCHEN...brbrThe open concept of the first-floor boasts soaring vaulted ceilings and is perfect for entertaining the whole crew. Among the many aviation-inspired touches in this home is an impressive plane propeller ceiling fan that keeps the entire living area and kitchen cool. The cozy living area is the perfect place to let the jet-lag wear off while enjoying the large flat screen TV that hangs in front of comfortable seating options, including a Queen sleeper sofa to accommodate extra guests in a pinch. There's also a convenient half bathroom in the hallway.brbrNext to the living area is the gourmet kitchen, separated from the main living area by an island with bar seating for two. The kitchen is equipped with stainless steel appliances and every tool you'll need to prepare a home cooked meal. A separate dining area, located just across from the kitchen, has seating for four. Open the large French doors next to the dining area and let the island breezes flow through or simply enjoy the view of the backyard.brbrTHE POOL AREA...brbrThe private pool area is truly a 'first class' highlight of this home. Tropically landscaped to create the ultimate island feel, the private heated pool has a soothing waterfall wall and is fully fenced for privacy. The pool gets plenty of sunlight all day long, and the comfortable patio furniture offer an ideal option to lay out and read a book or enjoy a cocktail. Your propane BBQ grill is ideal for a poolside dinner at home. A private covered carport offers off-street parking with an automatic retractable gate.brbrTHE ACCOMMODATIONS...brbrThis home's layout is unique in that it has maximized bedroom and bathroom space, creating ideal escapes and spa-like quarters for each guest. Each of the three bedrooms is a private suite, with an en-suite bathroom, spacious closets, ceiling fans, and flat screen TVs. In LAYOVER in PARADISE no one gets the 'short end of the stick' with a tiny bedroom. The bedroom layout is as follows:brbr• First Floor Master Suite: King bed, a massive walk-in closet fit for royalty, and an en-suite bathroom with dual sinks, a bathtub, and a glass shower.brbr• Second Master Suite: Queen bed, a comfortable sofa, and an en-suite bathroom with a glass shower.brbr• Third Master Suite: Two Twins OR One King bed and an en-suite bathroom with a glass shower.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 and full cable includedbrbrOther 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 adults

**LAYOVER in PARADISE @ CASA MARINA** New Home / Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$298.58

The Grand Turk | Key West Condo with Pool, Hot Tub & Private BalconybrbrWelcome to The Grand Turk, a spacious and inviting 2-bedroom, 2-bathroom condo located in the serene Sunrise Suites community on Key West's southeast side. Just one mile from the beach and 10 minutes from the excitement of Duval Street, this island retreat combines resort-style amenities with the comfort of home—perfect for families, couples, and friends seeking a relaxing yet well-connected Key West getaway.brbrThe Ambiance:brStep inside The Grand Turk and enjoy a bright, coastal-inspired space designed for comfort and easy island living. This thoughtfully laid-out condo sleeps up to six guests, featuring a king-size primary bedroom with an en-suite bathroom, a queen bedroom with convenient hallway-access bath, and a queen pull-out sofa in the living room. The open living area is ideal for unwinding after a day of adventure, complete with TV, cable, complimentary WiFi, and central air conditioning. The fully equipped kitchen includes all cooking essentials, a dishwasher, and a Keurig coffee maker—perfect for casual meals or morning coffee. Step out onto your private balcony to enjoy poolside breezes, afternoon lunches, or a quiet moment to relax.brbrGuest Access:brEnjoy a smooth, stress-free arrival with our contactless check-in process. Guests will receive a personalized access code prior to arrival for easy entry.brbrGuests also have access to Sunrise Suites' shared amenities, including:br- Communal heated pool and hot tubbr- Tennis courtsbr- Scenic walking paths and biking trailsbr- Shared washer and dryer facilitiesbr- Convenient elevator and stair access to the unitbrbrLocation Highlights:brLocated within the peaceful Sunrise Suites Resort, The Barbados is just minutes from Smathers Beach, Higgs Beach, and the energy of Duval Street. Explore Key West's vibrant dining, nightlife, and attractions, then return to your quiet retreat to unwind. The Key West International Airport is only a few minutes away for easy travel access.brbrGetting Around:brWith parking available, you'll have easy access to explore the island by car. If you prefer to travel by bike, scooter, or golf cart, rentals are nearby for your convenience. Key West's walkability means many attractions are just a short stroll away, and for longer distances, taxis and rideshare services are readily available.brbrOther Things to Note:br- Pet-Friendly Policy: Pets are welcome!br- Maximum weight: 40 lbs per petbr- $20/night per pet (2-pet maximum)br- Please notify us if you plan to bring your furry friend!br- Guests must be 25 years of age or older to reserve this property.brbrCheck-In: 3:00 PMbrCheck-Out: 11:00 AMbrbrTo 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, pool, parking areas, 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.

The Grand Turk | Spectacular Sunset View, Private

Key West, Florida, United States

Bed

Bath

Sleeps

$308.39

CLASSIC CHARMER...brSome of the best things come in small packages and this conch cutie is no exception. Nestled in the exclusive Casa Marina district, you will delight in this serene neighborhood that's close to the Atlantic Ocean, beach front restaurants, the south end of Duval Street and the White Street gallery and shopping area. The perfect fusion of economy and island dazzle!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brSip your morning beverage on the classic front porch and imagine the day's adventure ahead. In this prime location, you'll enjoy the serenity of this tranquil residence while you are an arm's length from all the exuberance of Key West fun. Take refuge inside after a day in the sun with a bright, open Great Room that invites restful repose and lively connection with loved ones. This cozy space is perfect for indulging in your favorite TV shows and fashioning cocktails and culinary creations in your modern, well-stocked kitchen with stainless appliances. An ample laundry room sits just off the kitchen for your convenience. brbrSLEEPING ARRANGEMENTS...brWhen you've exhausted your day with the outdoor magic of the island, lay your weary body down in bedded bliss. The primary bedroom features a plush king bed with an en suite bathroom with a shower. The other room offers two twins that can be converted to a king upon request. Both rooms come with wall-mounted TVs for your enjoyment. An additional bathroom lies off the Great Room area with a shower/tub combination. brbrOUTDOOR LIVING...brSatisfy your traveler's soul with a pool that comes heated in the cooler months and can be chilled upon request. The pool deck provides the ultimate zen. Beautiful tropical foliage shades and surrounds your sparkling watering hole, equipped with loungers, chairs and a cushioned outdoor couch. Dine al fresco at the outdoor table and chairs while your fresh catch is cooking on the electric grill. brbrPARKING...brThere are 2 parking spaces available for this home.brbrPETS...brPets are considered at this home and a pet fee is required. 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.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).brbrCOME PLAY IN PARADISE...

HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$438.57

Note: In 2026, bookings will require a minimum stay of 28 nights.brbr2 EVENT SPECIAL: Starting on Friday, October 16, 2026, the first day of FANTASY FEST WEEK and ending on Friday, November 13, 2026 right after POWER BOAT RACE WEEK. A total of 28 nights. There is some wiggle room if you need to adjust the dates. These are 2 of the most popular events in KW and you'll find the rate to be very reasonable.brbrbrIt's all about LOCATION! This charming, sunny, end unit townhome, located in quiet Truman Annex, is within walking distance to the best of Key West. Just two blocks to Duval St., a popular street for restaurants, entertainment and shopping. Grab your camera and walk only 2.5 blocks to Mallory Square and the nightly 'Sunset Celebration'. You are also close to the best beach in Key West at Fort Zachary State Park. The beach offers bathrooms, showers, a large concession area, chairs and umbrellas, snorkeling, shade trees, picnic tables, grills and a fort to explore. A great way to see the island is by bike and you can rent them one block away. Scooters and electric carts are also available. brbrThe first floor of our townhome has a welcoming open floor plan with two sets of French doors leading out to a private deck with tropical landscaping and a grill. The newly renovated, fully equipped kitchen has granite counter tops and stainless steel appliances. You will love the Caribbean style plantation shutters throughout the home. The shared pool with lounge chairs is right outside the back gate. brbrThe second floor offers two bedrooms with queen size beds and two, newly renovated full bathrooms. Each bedroom has vaulted ceilings, big closets and a set of French doors leading out to covered balconies. And, there is a convenient washer and dryer on this floor.brbrEnjoy additional amenities such as smart TV's in every room, free WIFI, ceiling fans throughout including the back deck. You have a reserved, covered parking space steps from the front door. We also have a stack of beach towels and beach bag for you to use. Make sure to check out the 'Starfish' Binder full of activity ideas, restaurant menus and helpful hints.brbrNow this is vacation!

STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located ¼ mile from one of the best beaches on the island. The Shipyard units are single level condominiums which have private courtyards on the first level. All properties are outfitted with washer/dryer, pots; pans, towels linens, have central air conditioning, off street parking and pool access. This property is a garden level condo and has recently been refreshed! New additions include all new flat screen TVS, linens, and housewares.brPlease note: This property requires a 28 night minimum stay.

ISLAND TIME at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$380.33

Romantic Retreat is an Historic, free standing cottage which, in the 1800`s, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV. Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.brbrHistoric Romantic Retreat dates back to the 1880`s when this building was used as a cistern. Over the years, a building was added on top of the cistern when rainwater was no longer collected from the gutters. It has been totally renovated with vaulted ceilings throughout. Painted in a light tropical blue with fish and aquatic art by Carrol Swayze, this delightful private unit is next to the pool. An under counter refrigerator, toaster/oven, blender, perfect for light meals. There is also a Weber grill by the pool for your use. A covered veranda at the rear of the pool is perfect for a game or lunch under the fan. Cooled with ceiling fans/Mitsubishi split units for cooling and heat, plantation shutters will remind you you are on a tropical Island. It also has a Bose Bluetooth speaker and a large Alexa for your favorite music or answer to questions. Use of 2 heated pools, the Family pool or the Adult’s Only pool across the street at 915 Center St. There are also 2 W/D’s for your use after 5 pm when housekeeping is finished. Pool towels are provided and you will receive daily housekeeping.brbrYou have a private deck with table, chairs, love seat. You have access to 2 heated shared pools and the grounds.brbrHousekeeping and groundsman/maintenance are on the property daily from 9 - 5pm daily and you receive daily maid service.brbrQuiet vacation rental neighborhood. Bike/moped rental at corner, CVS, Subway, Doctor`s office across Truman.brbrWalk, bike, moped, electric car. There is also a free bus around Old-town and there is a map of all the stops in your in-room information book. Stops are just around the corner from us!brbrRomantic Retreat is only 1/2 block off Duval Street within walking or biking distance of most places you may want to visit. There is a 24 hour CVS, Subway across the street and on the corner there is a bicycle/moped rental.brRegistered guest must be 25 or older during March/April (Spring Break). Please keep noise to a minimum after 10 pm at the Family pool as other guests may have early morning plans.

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Key West, Florida, United States

Bed

Bath

Sleeps

$244.28

Consider this house your home away from home while you visit Key West. This wonderful property features 2 queen bedrooms, a cozy living room with a futon, and a refreshing bathroom with a shower. With AC and WiFi included, guests can relax and unwind in this terrific space. Experience the magic of Key West at our welcoming house.

Charming 2-bedroom house with AC, WiFi in cool Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$398.95

This Historic unit has Pale blue interiors, small efficiency kitchen, platform Pottery Barn King memory foam bed with multiple basket drawers underneath for storage, large shower. Large private deck with 2 person spa, hammock, outdoor sofa and table/chairs. Bose Bluetooth speaker, Alexa. Private gated compound and gated entrance to Honeymoon Hideaway. Renovated August, 2019 with new full bathroom and designer kitchen with dishwasher, 2 burner stove, refrigerator with freezer, microwave!brbrThis Historic unit is located in front half of 1880's Cigar Maker's Cottage, this sweet, petite unit is perfect for a couple who love a large outdoor space and don't require a spacious indoor space. Just renovated 8/19 with added full kitchen and stylish bathroom with custom shower.brbr2 heated pools (1 for Adults Only), Weber BBQ grill, Game Gazebo by Family Pool.brbrDaily Housekeeping and groundskeeper/maintenance are on the property daily.brbrQuiet vacation rental neighborhood with bike/moped rental at corner. CVS, Subway and Doctor's office is across Truman.brbrBike, moped, walk, electric carbrRegistered guest must be 25 or older during March/April (Spring Break). Please keep noise to a minimum after 10 pm as other guests might have an early morning excursion planned. If Staff is called more than once for excessive noise, you will be asked to leave with no refund.

Apartment

Honeymoon Hideaway, King bed, Private Deck & Spa!

Key West, Florida, United States

Bed

Bath

Sleeps

$754.88

*Please note that this home is available for 28+ night stays only.*brbrAmid the most iconic historic sites in Key West, you’ll find the Lighthouse Villa, a timeless and private Conch home. This tropically inspired three-level property has all the updated amenities for you and your guests to enjoy, plus be within walking distance of the Southernmost Point, the Hemingway House, and the Key West Lighthouse.brbrThe tropically inspired 3-bedroom, 4.5-bath home can easily accommodate a large family yet offers plenty of privacy by separating entertaining spaces from the tranquil sleeping areas.brThrough the front door is an updated kitchen and dining room filled with vintage touches. A small sitting area off the kitchen is just right for catching up on a nap or novel. The comfy larger family room includes a wall of French doors opening to the private pool and an additional dining area in your own landscaped sanctuary.brbrAfter enjoying a refreshing dip in the pool, rinse off in the outdoor shower or climb the back stairs to the upstairs bathroom.brbrTwo well-appointed master suites welcome you to the second level up a grand staircase.brbrThe first bedroom with king bed and a remodeled brightly tiled bathroom. beckon you to rest after a day of exploring the island. The second bedroom with a queen bed has access to a terrace overlooking the lush gardens -- a perfect spot to sunbathe or enjoy your first cup of coffee of the day.brbrHead up one more level to another queen bedroom plus an open alcove complete with two over-stuffed chairs, a flat screened TV, and a double bed -- perfect for older children or teens to have their own space.brbrEnjoy an afternoon cocktail as you watch the world go by on two front porches on the first and second levels overlooking the famous Key West Lighthouse.brbrExperience the Lighthouse Villa -- an amazing home that is perfectly located for ease of getting around Old Town.brbrEntry Levelbr- Large open kitchen and dining room with a table that seats 10br- A full bathroom is off the living areabr- Large open family room/ sun room, facing the pool.br- Laundry is under the stairs on the main levelbrbrSecond Floorbr- Master bedroom with extra-large partial en-suite bathroom (no toilet)br- A balcony off the master bathroom overlooks the poolbr- Hidden staircase to the poolbr- Second bedroom with queen size bedbr- Half bathroom down the hall, shared by both bedroomsbr- Balcony off the second bedroom overlooking Key West LighthousebrbrThird Floorbr- Full bathroom at top of stairsbr- Open floor plan with sitting area and full-size bed.br- Separate queen bedroom is straight aheadbrbrOutsidebr- Large pool with deck and three seating areasbr- Gas BBQ grill and counter space for cookingbr- A full bathroom is outside off of the sliding doorsbrbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- You must be 25 years or older to book this home.br- Lighthouse Villa is intended for vacation rental purposes only, it is not designed as corporate housing.br- Maximum occupancy is strictly enforced.br- Pool heat is available for an additional fee but must be requested at least 48 hours before your stay.br- Pool heat is not available between 4/1 and 10/31.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brStreet parking only.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brBedroom 2 / Queen bedbrBedroom 3 / Queen bedbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Lighthouse Villa by AvantStay | Southernmost Point w/ Pool, Patio | Long Stays

Key West, Florida, United States

Bed

Bath

Sleeps

$195.89

*Please note that this home is available for 28+ night stays only.*brbrEnjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one-bedroom/one-bath Key West rental home with a shared pool on the property.brbrJust a couple of blocks to Duval Street, walking distance to restaurants, shopping, and attractions of Old Town Key West. What a great location; park your car and jump on your bike for a relaxing visit in our island city.brbrIbis is perfect for a couple or single working or staying for a month or longer in Key West. Simple but comfortable, Ibis has a kitchenette with granite countertops and 2 bar stools for enjoying your morning café con leche and guava pastry.brbrThe kitchenette opens onto the living area with a flat-screen TV. The bedroom has a king-size bed with a TV for watching movies in bed. The bath is just off of the bedroom.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- This home has access to a shared pool and is part of a gated community.br- Coin-operated laundry room in the compound.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrPets:br- This home allows pets for a fee. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- We LOVE pets, however- Certain breeds typically have to have an additional owner or HOA approval. If your pet falls under any typical breed restrictions (breed, size, weight) please let us know so that we can confirm!brbrParking Details:brParking is first come first serve. Otherwise, street parking is available. brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Ibis by AvantStay | Close to Duval Street w/ Shared Pool | Month Long Stays Only

Key West, Florida, United States

Bed

Bath