Vacation Home Rentals By Owner In Key West, FL

Key West Hideaway is an Historic home from 1874, completely renovated. Two upstairs Q memory foam mattress bedrooms, 2 Q memory foam mattress downstairs bedrooms. Each bedroom has a safe, Smart TV, Amazon Alexa, private bath. Q sleeper sofa with 5” memory foam mattress in LR. 76” Smart TV in LR, 32” Smart TV’s in BR’s, Amazon Alexa, Bose bluetooth speaker, full gourmet kitchen, rear veranda. 2 heated pools. 1/2 block off world famous Duval Street. On a quiet 2 block lane. CVS (24 hour) and Subway are across Truman Ave. Moped, bicycle, electric car rental at corner. If you rent from them, they will give you free ride to airport upon departure! Multiple restaurants, bars, dessert bars within walking distance. We are the most centrally located guest accommodations close to Duval but nice and quiet! Key West Hideaway is a 2 story, 1874 historic, private home with front and rear private porches. It is a 4 bedroom/4 bath house with Q sleeper sofa. You have access to 2 heated pools, gazebo with fun games. Use of W/D's after 5pm. There is also a totally private outdoor shower with hot/cold water to use anytime! Housekeeping and groundskeeping/maintenance on site daily from 9-5. We are 1/2 block off world famous Duval Street and Truman Avenue but on a nice quiet 2 block lane in Historic Old Town with other guesthouses and vacation rentals. Very safe, quiet and convenient to all Key West has to offer. Rent a bike, moped or electric car if you don't feel like walking. However, you will be in walking distance of most things in Key West!

Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!

Key West, Florida, United States

Bed

Bath

10

Sleeps

$1540.13

Palmwater Retreat – A Boater’s Dream...Your Luxurious Key West Escape Awaits!brbrNestled in the exclusive Key Haven neighborhood, just minutes from the vibrant energy of Key West, this stunning five-bedroom, four-and-a-half-bathroom waterfront home offers the ultimate tropical retreat. Whether you're seeking a peaceful getaway or an adventure-filled escape, this spacious 4,000+ square foot oasis is the perfect destination for your next vacation.brbrTropical Tranquility Meets Boating Paradise:brWake up to the gentle sounds of the water and spend your days soaking in the Florida sunshine by the heated saltwater pool with a tranquil water feature. With 125-feet of waterfront dock space, a 10,000-pound boat lift, a fish cleaning station, a 400-Pound ice machine, and a fish/bait freezer available for you to use during your stay, and easy deep-water access, this home is a fisherman’s dream. Bring your own boat or rent one locally to explore the crystal-clear waters of the Keys, go fishing right off the dock, or launch a kayak for a peaceful morning paddle.brbrOutdoor Living at Its Finest:brStep through the full glass accordion-style doors and experience seamless indoor-outdoor living. The sprawling patio and tropical landscaping provide the perfect backdrop for relaxation and entertaining. Fire up the grill in the fully equipped outdoor kitchen, dine under the stars at the outdoor dining table, or unwind in a lounge chair with the warm ocean breeze surrounding you.brbrSpacious & Elegant Interiors:brDesigned with both comfort and style in mind, this home features soaring ceilings, an open-concept layout, and expansive views throughout. The living room is warm and inviting, with plush seating, a 75-inch television, and a custom-built bar area—ideal for gathering with friends and family. The gourmet kitchen is a chef’s delight, featuring luxury Italian custom cabinetry, an induction stove, a spacious island with seating, and top-of-the-line appliances.brbrBeautifully Appointed Bedrooms for Ultimate Relaxation:br- First-Floor Primary Suite – A peaceful retreat with a king-size bed, luxurious en-suite bathroom, and private access to the pool and patio. Unwind in your spa-like bath, complete with a walk-in shower and high-end finishes.brbr- Second-Floor Primary Suite – A spacious sanctuary with a king-size bed, two walk-in closets, and a serene sitting area. The en-suite bathroom is designed for relaxation, featuring a soaking tub, separate walk-in shower, and dual vanities. This suite overlooks the patio and pool, offering a tranquil escape.brbr- Second-Floor Guest Suite – A bright and airy bedroom with twin beds that can be converted to a king-size bed, a large sitting area, a small refrigerator, and a private en-suite bathroom.brbr- First-Floor Guest Bedroom – A charming retreat with twin beds that can be converted to a king-size bed, sharing a Jack-and-Jill bathroom with the adjacent king bedroom.brbr- First-Floor King Bedroom – A stylish and comfortable space with a king-size bed, sharing the Jack-and-Jill bathroom, featuring a spacious walk-in shower and elegant finishes.brbrEach bedroom is thoughtfully designed with plush bedding, ample storage, and a private television, ensuring restful nights after a day of adventure.brbrUnparalleled Amenities:br*Heated Saltwater Pool with Water Featurebr*Fully Equipped Outdoor Kitchen with Gas Grill, Refrigerator, and Dining Areabr*Expansive 125-Foot Waterfront Dock with Deep-Water Access, 10,000-Pound Boat Lift, Fish Cleaning Station, and Space for Water Toysbr*Offers a 400-Pound Ice Machine and a Fish/Bait Freezerbr*Offers Convenient Access to Both the Gulf and the Atlantic Oceanbr*Open-Concept Living Room with 75-Inch Television and Bar Areabr*High Ceilings and Luxury Finishes Throughoutbr*Ample ParkingbrbrThe Perfect Balance – Seclusion and Convenience:brLocated in a quiet, upscale waterfront neighborhood, this home offers a sense of secluded tranquility while being just minutes from the world-class dining, live entertainment, and historic charm of Key West. Whether you're boating, fishing, paddleboarding, or simply unwinding in paradise, this luxurious retreat is the perfect place to create unforgettable memories.brbrBook your dream getaway today and experience the best of Key West living!

Palmwater Retreat – A Boater’s Dream

Key West, Florida, United States

Bed

Bath

Sleeps

$262.88

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrThe sound of steel drums, the warm breeze off the water, the palm trees rustling in the sky… the essence of the Caribbean awaits in Key West for your next private vacation. This classic island townhome is located within Truman Annex, Key West's most exclusive gated community. From the Tommy Bahama furnishings and island inspired décor to the tropical outdoor courtyard, you’ll feel as if you’ve been transported to your own Caribbean island retreat. The location and accommodations of CARIBBEAN CHARM, coupled with Last Key Realty's unrivaled Guest Services, is certain to make your island experience one you’ll treasure forever. brbrTHE LOCATION...brbrTruman Annex is a private, gated community right in Old Town, Key West. You'll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town, yet you'll benefit from the peace and quiet that Truman Annex is known for. Although you won't need a car to get around from this excellent location, there is a reserved off-street parking space.brbrTHE COMMUNITY POOL & FORT ZACHARY TAYLOR STATE PARK...brbrThe landscaped community pool is located just around the corner and across the street, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile away from your front door.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE LIVING AREA...brbrCARIBBEAN CHARM has been furnished and decorated in a classic island style that can be found throughout the home. The living area is the entire first floor and has an open plan, with 11-foot ceilings and double French doors that provide plenty of natural light to enter. The living room features a large flat screen TV and comfortable seating options, including a plush sleeper sofa to accommodate extra guests. There's also a convenient powder room located on the first floor. The kitchen is fully equipped with all of the tools and appliances you’ll need to prepare a meal from home. The indoor dining table seats four and there’s additional seating at the kitchen bar. Enjoy an outdoor meal at your own private courtyard out front, with an outdoor dining set and a gas BBQ grill.brbrbrTHE ACCOMMODATIONS...brbr** Master Suite: Located on the Second Floor with a King bed, a large flat screen TV, a private balcony, a large closet, and an en-suite bathroom with a shower and tub combination.brbr** Second Bedroom: Located on the Third Floor with Two Twins OR One King bed, a flat screen TV, a closet, and an en-suite bathroom with a shower and tub combination.brbrEach floor closes off with its own separate door as well for extra privacy.brbrSmoking is not permitted in any Last Key Realty home. In addition, the Foundry does not permit smoking in the front garden patio areas or balconies. Therefore, this home is not a good fit for vacationers needing smoking accommodations.brbrbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & 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** Community Pool Accessbr** Propane BBQ Grillbr** Assigned Off-street Parking for 1 CarbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$225.31

In the center of Key West's prestigious Millionaires Row, Conch Republic House is a tranquil getaway for up to six in the Historic District of Key West. Walk 5 blocks to world-famous Duval Street or the marina. Only 8 blocks to Ernest Hemingway's House and the Lighthouse. In the morning enjoy a famous Five Brothers Cuban coffee or sandwich while in the evening you may choose to dine at one of the South's most popular restaurants, Cafe Sole, both just 100 steps away. 1G optic internet!

Conch Republic House - Key West Millionaires Row

Key West, Florida, United States

Bed

1

Bath

6

Sleeps

$6131.25

Welcome to 921 Windsor Lane, a newly built coastal-modern retreat in the heart of Old Town Key West. Located just half a block from Truman Avenue and about an 8-minute walk to Duval Street, this stand-alone home offers the perfect blend of comfort, style, privacy, and walkable island living.brDesigned for families, couples, and friends traveling together, the home sleeps up to 8 guests and has a layout that feels both open and inviting. Upstairs, you’ll find two large king bedrooms, each with its own private en-suite bathroom. Downstairs, the home offers additional sleeping space with two queen foam-mattress sleeper sofas, making it easy to accommodate extra guests comfortably.brThe main living area was designed for gathering and relaxing. A spacious open kitchen flows into the Florida Room/family room and dining area, while a separate living room offers even more space to spread out. The kitchen is fully equipped with a full-size refrigerator, 36-inch stove with oven, drawer microwave, ice maker, wine cooler, large island with seating for 4, and a double farmhouse-style sink. A dedicated coffee and tea station makes mornings easy before heading out to explore Key West.brUpstairs, the home continues to impress with a convenient wet bar with sink & small fridge and washer and dryer. The primary suite features a king bed, walk-in closet, a spacious en-suite bathroom with walk-in shower, soaking tub, and a his & hers vanity, plus a private balcony overlooking the pool. The guest suite also has a king bed and a private en-suite bath with a walk-in shower and single vanity.brOutside, the private backyard is built for lounging and enjoying the island atmosphere. The heated and chilled pool can be enjoyed year-round, and the pool deck includes two chaise lounges, additional easy seating, and side tables for laid-back afternoons and evenings at home. Rear doors from the house open directly to the pool area, creating an easy indoor-outdoor flow.brOne of the rare advantages of this Old Town location is the private gated parking. The property includes space for 1 car and 1 golf cart, an automatic sliding entry gate, an EV charging station, and a separate golf cart charging stationfor guests who choose to explore the island that way.brThe home also includes high-speed Wi-Fi, smart TVs with streaming capability in the bedrooms, family room, and pool area, plus beach gear for guest use including 4 beach chairs, 2 umbrellas, beach towels, and a small cooler.brWhether you’re spending your days walking Old Town, dining on Duval, relaxing by the pool, or heading to the beach, 921 Windsor Lane is designed to make your Key West stay feel easy, stylish, and memorable.

Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval

Key West, Florida, United States

Bed

Bath

8

Sleeps

$4567.51

Summary:brbrSix Luxury Suites Creating 9 BD/ 7 BA, Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Porches and Patios. Sleeps up to 30.brbrbrbrThe Space:brbrEscape the Ordinary...brbrbrbrThe full offering of all 6 luxury suites of the Lighthouse Suites Collection delivers 9 bedrooms, 7 bathrooms in 3 buildings accommodating up to 30 guests all recently renovated and refurbished in 2024 and 2025. Each unit contains balconies, porches or patios with stunning views of the Key West Lighthouse, partial Duval Street views and a partial view of the famous Hemingway House. By reserving the entire Lighthouse Suites Collection, all of your guests will have exclusive access to the two brand new oasis pools and all of the property amenities in a contained boutique compound environment located on a quiet Key West Lane.brbrbrbrSuite Amenities:brbrbrbr • Luxury King and Queen beds in all units with premium linensbrbr • Sleeper sofas in each unit except Key West Light Suite which has a Queen loft bedbrbr • Six fully equipped kitchen with granite countertopsbrbr • Six spa quality rain shower bathrooms and one half bath in the Carysfort Suitebrbr • Hardwood flooring throughout the suitesbrbr • Spacious private and porches balconies and patios for each suite with amazing viewsbrbr • Smart TVs with the latest Roku device for apps and streaming in every roombrbr • High-speed Fiber Wi-Fibrbr • Washers and dryers in every unitbrbr • Luxury well-appointed furnishing and artworkbrbr • Reserved parking space for six vehiclesbrbr • Private entrances for all units and lockout doors for two of our combo unitsbrbr • Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Lighthouse Suites Collection offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbr brbrThe Lighthouse Suites Collection is truly one of a kind. This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbr brbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbr brbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites. brbr brbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbr brbrProperty Amenities:brbr brbr • Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr • Brand-new spacious pool decks around each poolbrbr • Six luxury teak chaise loungers with umbrellas and pillowsbrbr • Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr • Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr • A brand-new 200 SF teak pergola with a louvered open or closed ceiling brbr • Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr • Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr • Covered bar kiosk for enjoying a cocktailbrbr • Key West tropical foliage throughout the property with lighted step-stone pathsbrbr • Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr • Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3, two-bedroom suites, 2, one-bedroom suites, 1, one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbr brbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbr brbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbr brbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbr brbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbr brbr • The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbr brbr • The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbr brbr • The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbr brbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbr brbr • Key West Lighthouse Museum, 2-minute walkbrbr • Ernest Hemingway Home and Museum, 2-minute walkbrbr • Blue Heaven Restaurant, 5-minute walkbrbr • Southernmost Point Buoy, 8-minute walkbrbr • Key West Butterfly Conservatory, 8-minute walkbrbr • Sloppy Joe’s Bar, 12-minute walkbrbr • Key West Amphitheater and Park, 12-minute walkbrbr • Mallory Square Sunset, 12-minute walkbrbr • Fort Zachary Taylor State Park & Beach, 12-minute walkbrbr brbrWe look forward to welcoming you to paradise!brbrbrbrGuest Access:brbrPrivate entrances to all 6 suites.brbrbrbrThe Neighborhood:brbrLocated on a residential street just a half-block off of world-famous Duval Street.brbrbrbrGetting Around:brbrKey West is a very walkable city. We also have bicycle and scooter rental companies, city buses, taxis and ride-share services.brbrbrbrOther Things to Note:brbrPlease see the welcome book inside your suite for any other information you need, including how to use the grill and fire pit.brbrbrbrInteraction with Guests:brbrContactless check-in using smart locks. We are available 24/7 by phone. Staff will be on the property daily and weekly to clean the outdoor area and service the pool and landscaping.

Lighthouse Suites Collection

Key West, Florida, United States

9

Bed

7

Bath

30

Sleeps

$1586.14

Captain's Cove | Canalfront w/ Pool & Boat LiftbrbrWelcome to Captain's Cove, a stunning 4-bedroom, 4-bath waterfront retreat designed for those seeking the ultimate Florida Keys escape. Perfectly positioned along a deepwater canal with direct ocean access, this beautifully updated home offers a seamless blend of upscale comfort and laid-back island living. Whether you're bringing your boat, fishing from your backyard, or simply soaking in the tropical surroundings, Captain's Cove delivers an unforgettable experience.brbrThe Space:brStep inside to discover bright, open living spaces filled with natural light and finished with sleek tile flooring throughout. The thoughtfully designed layout creates an easy flow between the living, dining, and kitchen areas—ideal for both relaxing and entertaining. The chef's kitchen is a true showpiece, featuring a dramatic waterfall island, brand-new stainless steel appliances, and modern finishes that elevate every meal and gathering.brbrEach of the three main bedrooms features a king bed, along with a fourth, smaller bedroom offering a queen bed, all complemented by four full bathrooms for added comfort and privacy.brbrGuest Access:brGuests enjoy full access to the home, including private outdoor spaces and a designated covered parking spot. Located along the Riviera Canal in the quiet New Town area, Captain's Cove offers a tranquil residential feel while remaining close to all the action of Old Town.brbrOutdoor Living:brThe outdoor space at Captain's Cove is where this home truly shines. Enjoy your private waterfront oasis, complete with approximately 58 feet of seawall and a new 24,000 lb boat lift (boat not included), making it effortless to get out on the water. After a day of boating or fishing, unwind in the heated saltwater pool, enhanced by a tranquil water feature, lush turf, and ambient landscape lighting.brbrA full privacy wall and fencing create a serene, secluded setting, while the integrated mosquito control system ensures comfortable outdoor enjoyment day or night. Whether you're lounging poolside, dining al fresco, or watching the sunset over the canal, this space is designed for true island relaxation.brbrKey Amenities Include:br- Direct canal frontage with a 24k lb boat liftbr- Heated saltwater pool with water feature and automationbr- Modern kitchen with waterfall island and stainless appliancesbr- Whole-house automatic generatorbr- On-demand gas water heaterbr- Private, fully fenced property with insect control systembr- Automatic front gate and circular drivewaybr- Covered parking and ample additional spacebrbrLocation:brSituated in a prime waterfront setting, Captain's Cove offers quick and easy ocean access, making it ideal for boating and fishing enthusiasts. Enjoy the peaceful surroundings of the Keys while still being within reach of local dining, shopping, and attractions. Whether you're heading out on the water or exploring nearby islands, this location provides the perfect balance of convenience and tranquility.brbrOther Things to Note:br- Guests must be 25 years of age or older to reserve this property.br- A minimum stay of 30 days is required, in accordance with local regulationsbr- This property is ideal for boating enthusiasts. Please inquire for dockage details.br- The boat is not included.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt Colocada Vacation Rentals, we take pride in offering thoughtfully curated homes that let you experience Key West like a local. If you have questions or would like recommendations for dining, activities, or hidden gems, we're always happy to help make your stay at Captain's Cove unforgettable.

Captain's Cove | Canalfront w/ Pool & Boat Lift

Key West, Florida, United States

Bed

Bath

Sleeps

$789.8

Located in the coveted Historic District of Old Town! Situated on a quiet residential street, close to the Atlantic Ocean, beachfront restaurants, the Southernmost Point of the United States, the South end of Duval Street, and the White Street gallery and shopping area.brbrTHE MAIN HOME…brAs you enter the main home, you will be captivated by the huge high-end chef’s kitchen, natural light, and hardwood floors. A white, quartz waterfall island has seating for four and a built-in microwave. Custom cabinets, recessed lighting, and stainless-steel countertops complement this unique home. Stainless steel KitchenAid appliances and a large refrigerator are sure to impress the chef in your group.brbrThe adjacent open-concept living room/dining room and convenient powder room are accented with Dade County pine and designer décor. A large L-shaped sleeper sofa, a chair, and two swivel chairs provide views of the large-screen TV and the pool. The dining area seats 6 comfortably at the trestle table.brbrA lighted staircase at the entry leads to the primary bedroom, a luxurious retreat, and an immense spa-styled bath, complete with private access to the front porch and a large, oversized 2nd-floor back deck accessed through double French doors and a bank of windows! It is adorned with a woven rattan bed, nightstands, lamps, a dresser, and a large screen TV. Two large closets are also provided for your extended stay. The oversized ensuite bath features a double walk-in shower, multiple showerheads, a soaking tub, a water closet, and dual sinks with lighted coral mirrors. The stackable full-size washer and dryer are conveniently located on the 2nd floor of the home.brbrThe 3rd floor has two additional ensuite bedrooms flanking the hall. The first guest bedroom includes a queen bed, nightstands with lamps (each with built-in USB charging), built-in open shelving, a dresser, a closet, and a desk, as well as an ensuite bath. The second guest bedroom has a canopy bed, side tables with lamps, a closet, and its own cozy, modern ensuite bath.brbrTHE BACKYARD & POOL…brStepping outside through the double French doors, you’ll be transported to your very own private oasis. The backyard is surrounded by privacy fencing and features lush tropical landscaping. You’ll have plenty of room for everyone to lie out, relax, or enjoy an outdoor meal. Taking a dip in the heated saltwater pool and spa is the perfect way to relax after a day of exploring the island. Treat everyone to a poolside BBQ using the propane grill and outdoor dining table. There’s even a convenient outdoor shower located by the pool area. brbrTHE GUEST COTTAGE…brSteps away from the pool is the guest cottage, which is like no other! The 1st floor includes an open-concept family room, a wet bar, and a wall of windows overlooking the pool. Ample seating, a large-screen TV, a washer/dryer, and a powder room provide all the comforts of home. Sleek stainless steel appliances include a microwave, refrigerator/freezer drawers, a sink, an ice maker, and a wine cooler to ensure refreshments are close to the pool and guests. The 2nd floor bedroom is cozy and comfortable. Reading in bed is no problem with two nightstands and lamps. Complete with a closet, ensuite bath, and walk-in shower, this charming space is perfect for guests.

Luxury Key West Compound with Pool, Guest Cottage, and Walkable Access to Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$394.14

Welcome to the ultimate waterfront retreat—a stunning, sun-drenched two bedroom, two bathroom home sitting right on the point, where unobstructed open water views stretch endlessly before you. Here, life is as vibrant as the crystal-clear waters that surround you, with breathtaking sunrises and sunsets painting the sky each day. Step outside onto your private dock and boat deck, offering effortless access to the open water. The community features a private marina with a boat launch. brbr2 pools, marina, boat launch all 15 minutes from key WestbrbrOpen water views throughout

Dream vacation home with open water views, boating, pools in Geiger Key

Key West, Florida, United States

Bed

Bath

Sleeps

$281.25

Adorable historical conch house 2 bdrm, 2 full bath and outdoor shower on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the palm tree leaves.Central location, walk or ride a bike to Duval.brbr1. Duval Street - 0.6 mibr2. South Beach - 0.7 mibr3. Higgs Beach - 0.6 mibr4. Key West Cemetery - 0.5 mibr5. Simonton Beach - 0.6 mibr6. Key West Butterfly and Nature Conservatory - 0.7 mibr7. Locals' favorite market, Fausto's, is just one block away

Eliza Street Retreat, 2 bedroom, 2 bathrm, + loft, private pool, great location

Key West, Florida, United States

Bed

Bath

6

Sleeps

$247.31

Welcome to Cocktails on the Corner — Your Tropical Oasis in Old Town Key West!brbrStep into the perfect blend of historic charm and modern luxury at this beautifully renovated 2-bedroom, 1-bathroom Conch-style home, ideally situated on the corner of Southard and Margaret Streets. Nestled just minutes from the vibrant heart of Old Town, this residence invites you to experience the laid-back Key West lifestyle with all the comforts you desire.brbrHighlights:brbrPrime Location: Just 4 blocks from iconic Duval Street and 3 blocks to the Historic Seaport waterfront — perfect for exploring on foot or bike.brbrCharming Conch-Style Home: A seamless mix of historic character and contemporary upgrades.brbrSpacious & Comfortable: Two beautifully appointed bedrooms plus a sofa sleeper in the living room, comfortably accommodating guests.brbrFully Renovated Kitchen & Bath: Quartz countertops, stainless steel appliances, breakfast bar with stools, and a modern bathroom with a large shower.brbrPrivate Outdoor Paradise: Enjoy your own 12 x 15 ft heated (optional) in-ground pool surrounded by lush tropical foliage and mature canopy trees.brbrInviting Outdoor Living: Fenced corner lot with high-top seating, sun loungers, rocking chairs, and a gas grill—perfect for relaxing or entertaining.brbrEntertainment Ready: 50” TV with Firestick, ceiling fans, and a cozy open floor plan for socializing.brbrLaundry Convenience: Full-size stackable washer and dryer tucked inside the primary bedroom.brbrParking: Street parking available on a first-come, first-served basis.brbrSleeping Arrangements:brbrPrimary Bedroom: King-size bed, large dresser, closet, ceiling fan, and TV with Firestick for your comfort and entertainment.brbrGuest Suite: Queen-size bed with plenty of natural light streaming through large windows.brbrLiving Room: Sofa sleeper offers additional sleeping space for guests.brbrRelax and Unwind:brbrWhether you're soaking in the pool under the tropical sun, grilling your fresh catch poolside, or exploring the lively streets of Key West, this home is your sanctuary. The fully fenced yard ensures privacy while the mature trees offer refreshing shade — making every moment spent outside simply unforgettable.brbrAdditional Details:brbrGuest Age Minimum: Primary guests must be at least 30 years old and remain on the property for the entire stay.brbrPet Policy: This is a pet-free home to ensure the utmost comfort for all guests.brbrPool Heating: Available November through April for an additional charge.brbrNo designated parking space: street parking is subject to availability.brbrPerfect for couples, remote workers, or small groups looking to immerse themselves in the best of Key West living. Whether you’re escaping winter or seeking a seasonal retreat, Cocktails on the Corner is ready to welcome you with warmth, style, and all the amenities you need for an unforgettable stay.

COCKTAILS ON THE CORNER- 2 Bedroom / 1 Bathroom W/ Pool - Old Town Key West

Key West, Florida, United States

Bed

1

Bath

6

Sleeps

Select Dates for Price

This recently renovated three-bedroom, two-bathroom home has a spacious post-and-beam addition that opens onto an outdoor area with a heated saltwater pool. Play bocce on the back lawn or enjoy a cold drink while lounging poolside.brbrThe open-plan kitchen with state-of-the-art appliances is a playground for the passionate chef, and the great room is ideal for entertaining friends and family. Blu is a home that is designed with comfort and relaxation in mind. Recline under the covered pool lounge or venture out to one of Key West's world-class restaurants. This unique property is ideally situated on the island, with the beach just a few blocks away and Cuban coffee shops steps from the house; Con Leche, Buccis, and Cheese Bread abound.brbr* Please note that this property can also be offered as a four-bed, three-bath (Blu on White) or a five-bedroom, four-bath (Big Blu).br Please let us know if you are interested in one of these options.

Blu a Grand, three-bedroom, two-bath, home with a heated pool in old-town KW

Key West, Florida, United States

Bed

Bath

Sleeps

$376.08

Welcome to our charming 3-story Historic Home, nestled in a quiet and desirable neighborhood, just a 5-minute walk from the beach. This spacious and open-concept home is perfect for indoor and outdoor entertaining, offering a truly unforgettable vacation experience.brbrKey Features:br • Large open-concept layout, ideal for family gatherings and socializingbr • Fenced yard providing privacy and a safe space for kids to playbr • Heated pool for relaxation and fun, no matter the seasonbr • Conveniently located just a short walk away from the famous Duval Street, known for its vibrant atmosphere and entertainmentbr • Luxurious primary suite featuring a spacious porch and balcony, perfect for enjoying morning coffee or evening sunsetsbr • Two spacious front porches that invite relaxation and offer a taste of classic Southern charmbrbrAccommodations:br • 3 bedrooms with en-suite bathrooms, ensuring comfort and privacy for all guestsbr • Loft area with 4 twin beds, a cozy retreat for kids or additional guests, accessible by a sturdy ladder. br • 2 dedicated work areas, allowing you to stay connected while enjoying your vacationbrbrWhether you're relaxing by the pool, exploring the nearby beach, or strolling down Duval Street, our historic home provides the perfect backdrop for a memorable vacation. With its blend of modern amenities and timeless charm, it's the ultimate destination for families seeking a comfortable and convenient getaway. Book now to secure your unforgettable stay!

Paradise on Von Phister, only a 5 min walk to the Beach!

Key West, Florida, United States

Bed

Bath

10

Sleeps

$329.78

Newly Renovated Townhome in Prime Old Town Key West located just 3 blocks from the beach! Experience the best of island living in this beautifully renovated 2-bedroom, 1.5-bath end-unit townhouse, perfectly situated in one of Key West's most sought-after neighborhoods. Features include a stunning new kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and a handcrafted Moroccan Zellige tile backsplash. The open-concept layout offers bright and welcoming living and dining spaces that extend effortlessly to a private deck - ideal for outdoor dining, entertaining, or quiet relaxation. Upstairs, two spacious bedrooms and a fully renovated bath provide comfort and style, while a convenient half bath serves the main floor. Ideally located off the quiet end of Duval so you have easy access to island's best dining and beaches without the nosy crowds.

Renovated Old Town 2 Bedroom with Private Backyard

Key West, Florida, United States

Bed

Bath

Sleeps

$168.22

To provide our guests with a clean and sanitized home, our cleaning service cleans AND disinfects all high-touch surfaces in household common areas (e.g. tables, hard-backed chairs, doorknobs, light switches, remote controls, keyboards, handles, toilets, appliances, etc.).brbrWe also feature no contact checkin, no need to go anywhere to get keys or checkin.brbrCome stay in a premier development in Key West. This is a great location to stay with a monthly rental minimum. Reservations must be by the month starting with the first of the month. Yearly rates available. brYou are close to everything Key West has to offer. brbrOur house offers many amenities to make your stay comfortable and convenient. brEach Bedroom on the second floor has a Queen Size Bed, a Flat screen Smart TV, a full size dresser and closet space. The first floor has the Full Size Kitchen, Dining and Living Area that leads out to a large screened-in back porch. Outside is a beautifully landscaped yard with room to enjoy for entertainment or relaxation in the backyard both daytime and with exterior lights at nighttime.brThe Gated Community includes 24-hour security, 2 outdoor pools, fitness center, and beautiful landscaping. Great community for the daily neighborhood walk or bike ride. We have bikes under rear steps in backyard. The Public Golf Course where the property is located is to play at your leisure. From our place, a 15-20 Minute drive to Duval St depending on traffic. A short minute or 2 drive or short bike ride to Lower Keys Medical Center, Gerald Adams Elementary and Florida Keys Community College. But yet everything seems like a short bike ride to everything Key West has to offer. Stay at our place while you enjoy Paradise.

Monthly Availability beginning May 2025

Key West, Florida, United States

Bed

1

Bath

Sleeps

$210.1

Just a short walk from the Resort style pool and fitness center, our townhome, situated on the 1st fairway of the Key West Golf Club, offers 2 bedrooms, each with en-suite bathrooms, and an office with a queen Murphy bed that can sleep 2 additional people. Upon entering, you'll be met with an inviting and serene space. There is a cozy living area with comfortable furnishings and screened in porch to enjoy your morning coffee or unwind after a full day of activity in key West! Indulge in culinary delights in a full kitchen with stainless steel appliances and everything you need to whip up your favorite recipes.brbrThe community boasts a large resort style pool as well as a second, small pool and a fitness center for your use during your stay!brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 11:00 AMbrQuiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 1 vehicle.

Fishpartment South

Key West, Florida, United States

Bed

Bath

Sleeps

$311.49

Captain's Wheel at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$292.96

**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additional credit card fees.brbrTRANQUILITY AWAITS…brAwaken your tropical senses in this well-appointed 3 bedroom, 2 bathroom retreat nestled into the Old Town district of Key West. Lush vegetation greets you at every corner of this property creating a sensation of tranquility. Well equipped with all the everyday home comforts enhanced by desirable modern luxuries, this haven is sure to make the most of your island vacation. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brThis charming Conch sanctuary exudes bright and crisp décor representative of coastal living. Easy living can be achieved as you sprawl out in the cozy living room that includes a flat screen TV and bookshelf full of novels for a rainy afternoon. A fully equipped kitchen lies nearby showcasing stainless steel appliances for meal prep which can be enjoyed at the indoor dining table for 4. Perch the windows open as natural lighting pours through and invite the island breeze in creating a cheerful indoor/outdoor space. An additional living space is located at the front of this home equipped with a comfy seating area and small kitchen steps away. This property is equipped with a Ring Doorbell located next to the front door of the home. brbrSLEEPING ARRANGEMENTS…brThe first guestroom comes with a comfortable queen bed, flat screen TV and closet space for your belongings. The second guestroom can be entered off the kitchen through double barn doors and includes a trundle bed, armoire storage and French doors leading out to the garden for your morning cup of coffee. Both guestrooms share a jack and jill full bathroom equipped with a walk in shower and newly refinished antique soaking tub. Residing within the front living area of this home is a full bed guest room and bathroom with a shower tub combo just steps away. An upstairs loft with a twin mattress or the sofa sleeper down below can be used for additional sleeping arrangements. brbrOUTDOOR LIVING…brYour dreamy outdoor oasis will fully complete your tropical vacation. A calming afternoon calls for unwinding in the heated dip pool followed by an evening under the stars in the rocking chairs or hammock. Enjoy grilling out on the BBQ and dining al fresco with seating for 4 as you map out your next day's adventures. A quaint front porch is the perfect spot for enjoying your cup of coffee as you watch neighbors pass by. Peacefully located, this home allows for the best kind of R & R with only a short ride into town or the sandy beaches of Key West. brbrPETS...brNo pets please.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).brbrSUN IS SHINING, THE WEATHER IS SWEET…

LA PUERTA ROSA~Charming 3 bed/2 bath Conch Home in Old Town Key West!

Key West, Florida, United States

Bed

Bath

Sleeps

$354.38

Escape to your own private paradise at Oasis on 18th, a luxurious three-bedroom, three-bathroom haven nestled within the prestigious gated Key West Golf Club.brbrThis meticulously maintained home, which happens to be the largest in the Key West Golf Club, offers the ultimate in comfort and relaxation. As you enter, you'll be greeted by the spacious living area, adorned with tasteful furnishings and elegant decor. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating an inviting space for gatherings and relaxation. Adjacent to the living area is a separate sitting room, providing additional space for relaxation and entertainment, complete with a pull-out sofa bed for overnight guests.br brThe kitchen is a chef's dream, equipped with modern appliances and featuring a spacious bar, two wine coolers and an extra beverage cooler, perfect for unwinding with your favorite vintage after a day of exploration. br brAscend the stairs to the upper level of this remarkable home to discover the primary en-suite bedroom, a refuge of comfort and tranquility. Adjoined to this elegant retreat is in the palm trees level Hemmingway sitting room, offering a whimsical escape amidst the canopy of palms with unparalleled views. Step out onto the second-floor balcony and soak in the beauty of the surrounding tropical landscape. Each of the other two bedrooms also boasts a shared balcony, offering private outdoor spaces to soak up the sunshine, tropical breeze and enjoy the fresh air. Additionally, guests will find themselves greeted by the comforts of home, with both bedrooms furnished with a Keurig coffee machine, ensuring that every morning begins with the perfect cup of coffee.brbrNestled in a quiet location within the privately gated Sanctuary of the Key West Golf Club, Oasis on 18th offers peace and tranquility while still being just a short 3 Mile distance away from the bustling energy of the famous Duval Street. Explore the vibrant shops, five-star restaurants, exciting attractions, golf and world class fishing, as well as fantastic opportunities for sightseeing, diving and boating before returning to your private oasis. In addition, just a short drive away you can be enjoying either Smathers Beach, Higgs Beach or Fort Zachary Taylor Historic State Park!br brOutdoor living is a dream at Oasis on 18th. Relax by the large PRIVATE HEATED POOL, surrounded by a charming herringbone brick patio. Fire up the new Weber Genesis four-burner gas grill for a barbecue, dine al fresco at the spacious dining table on the fully screened lanai, or unwind in the comfortable seating area – the choice is all yours.brbrSurrounded by lush manicured landscaping and overlooking a tranquil pond on the 18th hole, this home offers breathtaking views and unparalleled privacy. The private fenced yard adds an extra layer of seclusion, perfect for enjoying quiet moments in nature.br brAs part of the highly esteemed Key West Golf Club community, guests enjoy exclusive access to a wealth of amenities designed to elevate their stay. With not just one, but two pools, at their disposal, guests can choose between lounging in the tranquil ambience of the large resort-style pool or engaging in invigorating laps in the lap pool. The state-of-the-art gym caters to fitness enthusiasts. And for avid golfers, the crowning jewel of the community is the renowned Reese Jones Designed Golf Course, ensuring there's something for everyone to enjoy during their stay.brbrWith a private driveway and carport, parking is convenient and secure, allowing you to come and go as you please.brbrKey West Golf Club Amenities you may enjoy while staying at Oasis on 18th:br* 24/7 Security and Gated Entry br* Parking for 2 Vehicles br* 24 hr Fitness Centerbr* 2 Additional Pools, one being a Resort Style Pool & one being a Lap Style Poolbr* 1 Mid-Stay Cleaning is included in your staybrbrDon't miss the opportunity to experience the ultimate Key West getaway at Oasis on 18th. Book your stay today and make memories that will last a lifetime! We look forward to hosting you soon at Oasis on 18th!br brOther Things to Know:br* Guests must use their own logins for streaming services.brSecurity Camera -br* There is one active Ring Doorbell Camera located on the Front Door facing the street.br* Pet Friendly - 1 to 2 dogs allowed with a total weight of 50 lbs for both - restrictions on dogs may apply. br** Pet Fee of $500 per dog.br**Minimum Age to rent is 25 - Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Escape to Oasis on 18th w/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!

Key West, Florida, United States