Vacation Rentals By Owner In Key West, FL

Meadows Manor | Elegant Oasis with Private Pool & Parkingbrbr--- 3-Night Minimum Stay Required ---brbrDiscover the perfect blend of luxury and tranquility at the Mansion in the Meadows, a beautifully landscaped 4-bedroom, 4-bathroom haven in the heart of Key West. This stunning home features a private pool surrounded by lush greenery, providing an ideal oasis for families or groups seeking both relaxation and adventure. With a central location, you're just minutes away from all the vibrant attractions that Key West has to offer.brbrThe Ambiance:brStep inside the Mansion in the Meadows, where modern elegance meets tropical charm. Designed to accommodate up to eight guests, this spacious home boasts:br- Four inviting bedrooms, each featuring a plush Queen bed for ultimate comfortbr- Four beautifully appointed bathrooms ensuring convenience for all guestsbr- A fully equipped kitchen perfect for preparing meals togetherbr- An inviting living area that opens up to the outdoor spacebr- A private pool framed by luscious landscaping, perfect for lounging and soaking up the sunbrWith ample space and a thoughtfully designed layout, this home is perfect for creating unforgettable memories with loved ones.brbrGuest Access:brEnjoy a seamless arrival with our contactless check-in process. You'll receive personalized access codes prior to your arrival, allowing you to walk right in and start enjoying your vacation. Our team is available to assist with any questions or recommendations during your stay.brbrLocation Highlights:brNestled centrally in Key West, the Mansion in the Meadows offers the convenience of being close to everything the island has to offer. Explore nearby shops, restaurants, and vibrant nightlife, or take a leisurely stroll to the beach. This location provides a perfect base for experiencing the unique culture and charm of Key West.brbrTransportation Tips: brGetting around is a breeze at the Mansion in the Meadows! With on-site parking available, you can easily explore the island by car. Alternatively, rent a bike, scooter, or golf cart for a fun and eco-friendly way to discover local attractions. Public transportation options, including taxis and rideshares, are also readily accessible.brbrOther Things to Note:br- This property has 3 night minimum stay requirement.br- Private washer and dryer available for guest use.br- Lush landscaping enhances the outdoor experience.br- Guests must be 25 years of age or older to reserve this property.br- No pets allowed.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, driveways, pool, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible!

Meadows Manor | Elegant Oasis with Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$227.25

YOUR ISLAND TREASURE AWAITS...brThis cozy 2 bedroom 2.5 bath island sanctuary is nestled in the charming area of Bahama Village, a community known for its colorful Bahamian-style architecture and panoramic water views from the 19th century Key West Lighthouse. Enjoy close proximity to many popular open-air restaurants serving island-inspired fare, coconut-laden cocktails and live music. This home provides every creature comfort you'll need and is a short distance from lively Duval Street and sun-drenched beaches.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brAs you enter this adorable pink retreat, the cozy living area greets you and invites you to kick off your sandals and stay a while. A comfy sleeper couch and cushioned seating envelops you while you enjoy diversion on the large wall-mounted tv and cool off from your day's adventures in paradise. Continue down the hallway where you'll find a laundry closet and a powder room for your comfort and convenience, then enter the dine-in kitchen (table for 4) and enjoy meal prep in this clean and fully equipped and stocked kitchen. This property is equipped with a Ring Doorbell located next to the front door of the home. brbrSLEEPING ARRANGEMENTS...brTravel upstairs where you'll find two bedrooms, each with their own private shower bathroom. The primary features a king bed and the second bedroom offers a queen. Both are equipped with wall-mounted tvs and storage closets for your belongings.brbrOUTDOOR LIVING...brYou will love the quaint side yard hangout that offers a private hot tub, sunbathing loungers, an outside shower and 4 bicycles. A small porch gives entry to the kitchen area. brbrPETS...brPets are considered and a pet fee is required. Please leave the size and breed in the comments when inquiring. 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)brbrPARKING...brEnjoy the convenience of an off street graveled parking space for 1 vehicle.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-FILLED PLEASURES AWAIT YOU....

LA CASA ROSADA ~ Perfectly Located 2 BR, 2.5 Ba Home w/ Private Hot Tub!

Key West, Florida, United States

Bed

Bath

6

Sleeps

$242.85

Sunset Overlook | Waterfront Condo at Harbour Place in Truman AnnexbrbrWelcome to Sunset Overlook, a spacious waterfront condo located at Harbour Place in the highly desirable Truman Annex of Old Town Key West. With sweeping oceanfront views of Key West Harbor, this inviting retreat offers the perfect balance of scenic relaxation and walkable convenience. Start your mornings on the furnished balcony overlooking the water and wind down in the evenings as the sky lights up with unforgettable Key West sunsets. Whether you're visiting for beach days, boating adventures, or historic Old Town charm, Sunset Overlook places you right where you want to be—surrounded by harbor views and close to everything.brbrThe Ambiance:brSunset Overlook features a bright, open layout designed to showcase its stunning waterfront setting. Natural light fills the living and dining areas, creating a relaxed coastal atmosphere that draws your attention to the harbor views visible throughout the condo. The private, furnished balcony offers a front-row seat to passing boats and unforgettable Key West sunsets, making it the perfect spot for morning coffee or evening relaxation. Inside, guests will enjoy a spacious living and dining area with ample seating, a full kitchen equipped with modern appliances and a dishwasher for convenient meal preparation, free Wi-Fi, central air conditioning for year-round comfort, and easy elevator access.brbrGuest Access:brGuests enjoy full access to the entire condo, along with use of the shared on-site swimming pool. One complimentary parking space is included, and the building offers convenient elevator access. Entry is easy and secure with a digital E-lock, providing a unique code that is reset after each stay.brbrLocation Highlights:brLocated within Truman Annex, Sunset Overlook offers one of the most sought-after locations in Old Town Key West. Fort Zachary Taylor State Park and its sandy beaches are just a short bike ride away. Nearby streets are lined with restaurants, boutiques, and entertainment, while popular attractions such as the Key West Aquarium, snorkeling excursions, and the world-famous Duval Street are all within easy walking distance. From waterfront walks to iconic island attractions, everything you love about Key West is just moments away.brbrTransportation Tips:brWith a dedicated covered parking space, exploring the island by car is easy. Many guests choose to walk or bike everywhere, thanks to the home's central location. Scooters, bikes, golf carts, taxis, and rideshares are all readily available for getting around Old Town and beyond.brbrOther Things to Note:br- One private parking spot (parking fees may apply)br- Private washer and dryerbr- Dogs are welcome—just reach out for additional details. br- A minimum stay of 30 days is required, in accordance with local regulationsbr- Guests must be 25 years of age or older to reservebrbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrAt 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 Sunset Overlook unforgettable.

Sunset Overlook - Waterfront Condo at Harbour Place with Sunset View

Key West, Florida, United States

Bed

Bath

Sleeps

$981.0

Experience Island Living In The Treetops…brWelcome to your luxurious oasis in Key West, where modern comfort meets tropical paradise. This stunning new construction home features four spacious bedrooms, each with an en suite bathroom, making it the perfect retreat for families or groups seeking both relaxation and adventure. With lushly landscaped grounds, this 5,700 square foot property offers plenty of room to unwind and enjoy the beauty of the island.brbrImagine starting your day with a refreshing swim in the large, private, heated and chilled saltwater pool, surrounded by vibrant native trees and plants carefully chosen by a local arborist. You can enjoy the outdoor shower after a day at the beach or spend your evenings grilling under the stars.brLocated just a 7-minute bike ride to the beach and a 15-minute bike ride to Old Town Key West, you’ll have the best of both worlds. Spend your days exploring local shops, dining at world-class restaurants, and soaking up the sun out on the water, then return to your serene retreat in a quiet residential neighborhood.brbrThe property boasts a covered porch overlooking the pool, accessible by three sets of French doors and perfect for watching the breathtaking sunsets that Key West is famous for. With large windows and a great room nestled within a native forest, you'll feel connected to nature while enjoying the comforts of home.br Inside the home you will find handcrafted mahogany cabinetry throughout the kitchen and bathrooms showcasing unique local charm. Each bedroom is designed with comfort in mind, featuring easy-to-use blackout shades to ensure restful nights. With extra-large bedrooms, walk-in closets, work stations and televisions in every room, you'll find everything you need for relaxation and entertainment. The fully equipped kitchen invites you to create memorable meals with friends and family.brbr This is not just a vacation rental; it’s your home away from home. Experience the magic of Key West in a property that combines luxury, nature, and convenience. Book your stay today!brbrbr*Wifi and Washer/ dryer are provided*

4-bedroom New Construction house with private pool in Key West

Key West, Florida, United States

Bed

Bath

8

Sleeps

$273.0

***Pool on Property and use of Free Bikes During your Stay!!!***br***Contactless Check In and Check Out***br***Enhanced Cleaning Procedures***br***Private Entrance/Room/Bathroom***brbrLooking for the perfect AFFORDABLE hide-away in Key West Located in a remodeled Victorian Home - this guest room is just perfect for two and has a pool in the backyard!brbrThis guest room is cozy (the size of a small hotel room, 10'X12.5' plus bathroom) with a QUEEN size bed but is so much better than a hotel room. We provide high quality cotton sheets and thick, luxurious towels. We offer a studio kitchen with apartment sized fridge, microwave, toaster oven, coffee maker, two burner cook top, blender, and everything you'll need to cook and serve a romantic meal. It is nice to be able to make a sandwich or picnic to take to the beach! There is a wonderful table just out the back door if you would like to eat under the palm trees. brbrDon't want to cook brNo need really - just two and a half blocks up is Duval Street where hundreds of bars & restaurants await your fun times. The beach is a five minute walk and there you can enjoy the gorgeous warm turquoise water ALL YEAR ROUND. Just relax on the pristine white sand under the tall swaying palms. When you get too hot - simply stroll back to your air conditioned hide-away or take a dip in the pool. brbrTwo bikes are provided for your use at no extra charge. They are right on property with the number 6 (our studio number) on each bike. You will be able to ride to beaches, parks, botanical gardens and of course, bars, restaurants and sunsets!!brbrThe bed faces an armoire and 32' flat screen TV. The gorgeous Victorian Home which is now divided into individually owned rooms - is an architectural masterpiece... but unlike many bed and breakfasts, walls are thick and your privacy is insured. The neighborhood is a wonderful mix of guest houses, full time local folks, and visitors. While you are walking the streets - stop and chat a spell with anybody who is rocking on their front porch. You might meet some real Key West characters! Our location is so close to Duval (a five minute walk) - it will be a great place to gather with friends to head downtown.brbrOUTSIDE There is a wonderful back deck with lovely shaded eating area and pool, another picnic table under the huge Banyan tree, and lots of lounge chairs to lay in the sun. These are all within the fenced yard of the property. It really is amazing to find this quiet seclusion right off of the excitement of Duval Street!brbrWe want to provide an affordable solution to the high prices of Key West Hotels - and we think this is it! If you are looking for a full service hotel this is not for you. My studio is best for folks that want to see Key West, not stay in their room during their vacation. While it is quite small, it is one of the best values in Key West. We don't pretend to be a full resort, we are a great option for those that are looking for value and a clean well-appointed room! WE GUARANTEE YOUR UNIT WILL BE SPARKLING CLEAN UPON YOUR ARRIVAL. So come on down to the Southernmost City and have some fun!brbrYou will enjoy our 'Favorites' book which has all of the menus of our favorite restaurants and ideas for day trips. We live here and if you have ANY questions - PLEASE call and ask...we know ALL of the LOCAL HOTSPOTS.brbrYou can rent nightly or weekly!!! brbrRates range from $129 to $319 per night, holiday and special event rates may be higher.brbrYour Rental Will Include The Use of Two Bikes For Free!!!brbrOne Time Cleaning Fee - $90 on all stays regardless of length of stay.brbrbrbrbr

Apartment

Steps from Duval, Pool on Site & Bikes Included!

Key West, Florida, United States

1

Bed

1

Bath

Sleeps

$233.24

Escape to this bright, modern studio just two blocks from iconic Duval Street in the heart of Key West! Tucked in a secure gated complex of only 6 units, enjoy your own private seating area.brFeaturing a stunning kitchen with full-size gas range, dishwasher, microwave, and a beautiful bathroom. Sleep soundly with a comfy queen bed on the main level plus a luxurious King bed in the loft.brIdeal for couples or solo travelers craving convenience and comfort in paradise. Your perfect Key West retreat awaits!

Beach House, Modern Old Town Studio Near Duval - New Listing Discount!

Key West, Florida, United States

Bed

Bath

Sleeps

$237.45

You will love this quiet tree-top studio in the heart of Old Town Key West. Located just a block away from the Historic Light house and Hemingway house and very close to Duval Street. This is a cosy studio ideal for one person or a couple looking for a reasonable Key West get-away. There is internet access and satellite TV. Parking is on street. There is a BBQ gas grill and patio furniture for your convenience. You can enjoy the Island Breezes from your spacious deck. brThis property has a 30 day minimum stay requirement.

Apartment

@ KEY WEST DOWNTOWN STUDIO APT AMAZING PRICES FOR WINTER OF 2025

Key West, Florida, United States

Bed

Bath

Sleeps

$297.73

THE PROPERTY: Bohemian bits indoors and lush landscaping outdoors will give you that tropical island feeling you are looking for. Warm wood tones and exposed beams can be found in the main living area. The family room with sofa, chair, and TV is open to the kitchen and dining areas. A wooden island with seating is the perfect place to enjoy a snack or beverage. A bright kitchen provides all that you will need to prepare meals. However, while on vacation, you may prefer to walk to one of Old Town’s amazing restaurants. brbrThe bedroom is white and bright and adorned with bedside lamps and a nightstand. A dresser and closet provide you with storage. A partial wall with high shelves and a draped entrance separates the bedroom from the central living areas. You can also access the outdoor space from the bedroom. The bathroom is cozy and bright with a pedestal sink, tiled walk-in shower, and shelf storage. brbrThis unit in the duplex home comes with shared outdoor amenities including a deck under a giant Banyan tree, a grill, and an outdoor washer and dryer. Solaris Garden is ideal for the traveler looking for walkability as well as the desire to kick back and relax in a casual, carefree home. brbrSOLARIS GARDEN occupies the back section of this first-floor duplex home. SOLARIS COTTAGE occupies the front section of this duplex home. For information on renting both parts of this duplex, please see SOLARIS PAIR-A-DISE. brbrBED CONFIGURATION: The queen bedroom is cozy and comfortable for 1 or 2 guests. brbrOUTDOOR AMENITIES: This duplex home shares an outdoor garden area, deck, chairs, grill, and washer/dryer. brbrPARKING: There is no designated parking for this rental, however, there is usually parking available on nearby Petronia and Angela Streets. To avoid a parking ticket, please be sure that you don’t park in a spot labeled residential, as these are assigned to full-time residents.br brLOCATION: The property is on a tiny, one-way lane in Old Town, North of Truman Avenue and just a block and a half from Duval Street. Leave your car at home because you are just a short walk or bike ride to many tourist attractions, bars, restaurants, shops, and galleries including Mallory Square, known for breathtaking sunsets and performers.br brPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult. brbr***Managed by Historic Key West Vacation Rentals***

~ SOLARIS GARDEN ~ Relax and enjoy this Bohemian dream on a quaint lane.

Key West, Florida, United States

Bed

Bath

Sleeps

$421.03

Stunning 2-Bedroom Ocean-View Oasis at 1800 Atlantic – Key WestbrbrWelcome to your perfect tropical escape! This beautifully maintained, family-owned 2-bedroom, 2-bath vacation rental at the prestigious 1800 Atlantic in Key West offers breathtaking ocean views and all the comforts of home.brHighlights of Your Stay:brbr Spacious Accommodations:brbr Master Suite with a new king bedbr Guest Bedroom with a brand-new king bedbr Queen sleeper sofa in the living roombrbr Island-Inspired Interiors:brbr Bright Mexican tile flooring enhances the coastal vibebr Fully renovated kitchen (2022) with modern amenitiesbrbr Resort-Style Amenities:brbr Olympic-size heated pool overlooking the Atlanticbr 20-person Jacuzzi tubbr Tennis courts, including the only clay court in Key West and two additional hard courtsbrbr Unbeatable Location:brbr Directly on the Atlantic Ocean, next to Smathers Beachbr Just minutes from Key West’s historic district, famous for its bars, dining, and entertainmentbr Easily accessible by car (5 mins) or bike (10 mins)brbrParking & Connectivity:brbr Free assigned parking for one regular-sized vehicle — no extra fees!br High-speed internet access includedbrbrWhether you're relaxing poolside, hitting the beach, or exploring the vibrant local scene, our ocean-view condo is your perfect home base. Call us or stop by our office — we’re always happy to share local tips and favorite hidden gems.brbrWe look forward to welcoming you to paradise — we’re confident you’ll be back again!brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals

Key West, Florida, United States

Bed

Bath

Sleeps

$370.21

Tropical Garden-View 2-Bedroom Condo Near the Beach & PoolbrbrWelcome to your serene Key West getaway! This lovely and quiet two-bedroom, two-bath garden-view condo is perfectly situated just steps from the pool and moments from the beach.brbrInside, the entire unit features cool tile flooring throughout. Both bedrooms and the spacious living room open onto a private balcony with a peaceful view of the lush tropical courtyard and gardens — perfect for morning coffee or evening relaxation.brbr Master Bedroom: King-sized bedbr Guest Bedroom: Queen-sized bedbr Living Room: Queen sleeper sofabrbrThe fully equipped, full-sized eat-in kitchen offers everything you need for dining in, while the adjacent dining area comfortably seats six. A convenient wet bar completes the space for effortless entertaining. Stay connected with wireless internet available throughout the unit.brbrAmenities include:brbr One assigned covered parking space (vehicle height limit: 6'3)br Olympic-sized heated poolbr 20-person Jacuzzibr Sunning beach in the courtyardbr Small fitness centerbr Charcoal grilling stationsbrbrJust steps away from the sparkling Atlantic Ocean and right next to Smathers Beach, this condo offers the perfect blend of comfort, convenience, and tropical charm.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800

Key West, Florida, United States

Bed

Bath

Sleeps

$625.29

THE PROPERTY: An open staircase leading to the second floor is where your vacation begins! The reverse floor plan, tres chic décor, and open living room with vaulted ceiling are dazzling. Relax and mingle with guests in this beautiful, functional space. The petite yet mighty eat-in kitchen is equipped with stainless steel appliances and everything you need to prepare meals. Stroll through the living room’s French doors onto the comfortably furnished veranda and enjoy the cool breezes of Key West. The home’s first floor is where two king ensuite bedrooms are located, as well as a stackable washer and dryer. This unique home’s mix of white walls, wood accents and stylish art, will help you enjoy the Key West vibe. brbrShould you need additional space for wedding guests or a family reunion, Petite Maison may be rented together with Grand Maison. Together, both properties sleep a total of 12 guests and boast 6 ensuite bedrooms. Please see Maisons de Luxe to rent both homes. brbrBED CONFIGURATION: The smart floor plan of this cottage allows for two king bedrooms with ensuite baths on the first floor. Each bedroom has night tables, TVs, natural light and ceiling fans. brbrOUTDOOR AMENITIES: The second floor of this home opens onto a comfortably furnished covered veranda where you can enjoy coffee or cocktails. The home is close to Fort Zachary Taylor Beach. Please note this home does NOT have access to a pool.br brPARKING: There is parking for one car however, from this convenient location, you may find yourself touring Key West on foot. brbrLOCATION: Petite Maison is located on a quiet, hidden lane behind Duval Street. The home is on the southern end of Duval Street near cafes and night clubs. You can walk to many attractions including the Southernmost Point and the Key West Butterfly and Nature Conservatory. brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking property.brbr***Guests must be 25 years of age or older unless accompanied by an adult***brbr***Managed by Historic Key West Vacation Rentals***

~ PETITE MAISON ~ 2 king ensuite bedrooms on a quiet lane near Duval Street.

Key West, Florida, United States

Bed

Bath

Sleeps

$429.03

Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to your private balcony with great views of the property and Atlantic Ocean. The Owners are fishing enthusiasts as you will see when you relax in the comforts of home away from home. Totally renovated in the Summer of 2024. No attention to detail has been spared. brKing in master, 2 twins in guest and a sleeper in the living room. Ideal family unit that will comfortably accommodate a family of 6. brOlympic size heated pool, with a popular bubbling Jacuzzi for one of those rare cold winter nights. Did you know we are the only frost free city in the continental US. brTennis lovers will appreciate the only clay court on the island of Key West as well as recently renovated hard courts with the help of ATA. brWhere do you start in Key West from Fishing to Diving, to theater and the arts. So much to do and so little time will leave you with no choice other than to visit again. brNo where is more than 10 minutes away and there is really no need for a car, however you do get a rare free parking space with your property at 1800 Atlantic.brOur Property Manager lives on site and is a wealth of information should you happen to encounter him, ask him to tell you one of his Island Stories, and listen carefully. There is so much to learn. Many come and never leave, will you be one of those brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Premier Ocean views, expansive balcony, renovated kitchen & bath 2024

Key West, Florida, United States

Bed

Bath

6

Sleeps

$664.01

THE PROPERTY: Enjoy the walkable location of this charming property. As you enter the home from its covered rocking chair front porch, you are in the open concept living room and kitchen. The compact kitchen with peninsula seating is equipped with everything you need to prepare meals or snacks. The living room is comfortably furnished, including a TV and ceiling fan. The room’s large French doors open onto the partially covered deck where you can enjoy dining poolside. The fresh ‘catch of the day’ will taste great when cooked on the gas grill. The outdoor dining table is partially covered and provides a respite from the sun. After a day exploring Key West, cool off in your private pool or enjoy cocktails in the covered lounge area. brbrIdeal for a small family or two couples, this home provides a bedroom and full bath on each level. The primary open loft bedroom is located on the second floor and includes an ensuite bath with walk-in shower. The TV and seating area are a bonus in addition to the vanity/desk for primping or working in your home away from home. The secondary bedroom and hall bath with walk-in shower are located on the first floor. The built-in shelves, window seat, ceiling fan and TV add to this comfortable sleeping area. brbrThis home includes a small bonus space with a built-in bookcase and a love seat. No matter which room you choose as yours, this distinctive Key West cottage is sure to delight! A washer and dryer are located outside for your use.brbrBED CONFIGURATION: The primary king loft bedroom, ensuite bath with louvered door, and seating area are on the second floor, accessible via an open riser staircase. Please note upstairs shower may be tight for taller people due to sloped ceiling. The loft area is open to the area below as seen in the photos. The second queen bedroom with hall bath is on the first floor. brbrOUTDOOR AMENITIES: Private, refreshing cocktail pool with outdoor shower, gas grill, loungers, and Adirondack chairs. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The deck also includes a dining table and chairs as well as a comfortably furnished covered lounge area. brbrPARKING: No designated parking. On-street parking available in the neighborhood. brbrLOCATION: Old Town, South of Truman Ave. Known as Uptown Key West, this area features beautiful Victorian homes, historic cottages, and quiet tree lined streets. Potter’s Cottage is conveniently located minutes from Key West’s major attractions – including sun kissed beaches, restaurants, museums, galleries, and shopping. Just one block from the famous Duval Street, this location offers limitless opportunities to explore the city by foot. brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly).brbrSMOKING: This is a non-smoking home and property. brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~POTTER'S COTTAGE~ Key West charmer in great location with private pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$219.35

Oceanfront Overlook – Your Perfect Island RetreatbrbrWelcome to Oceanfront Overlook, a one-of-a-kind unit offering an unparalleled view of the Atlantic Ocean—your ideal home away from home in beautiful Key West. This spacious, fully equipped retreat features all the modern conveniences to make your stay comfortable and relaxing.brbrEnjoy breathtaking ocean views from every room. Both bedrooms and the living room are outfitted with sliding glass doors that open onto a large private balcony—the perfect spot for sunrise coffees or evening cocktails. You can even watch the sunrise from the comfort of your bed.brbrRecently renovated, the kitchen and both bathrooms showcase stylish finishes and thoughtful details, ensuring a luxurious experience throughout your stay.brbrKey West is bursting with activity and charm. Whether you’re into fishing, diving, or snorkeling, or prefer exploring museums, art galleries, and acclaimed restaurants, there’s truly something for everyone. While you may not be able to see it all in one visit, many guests return year after year to keep discovering more.brbrPlease Note:brbr Minimum stay: 28 days.brbr For rentals between December and April, stays must begin on the 1st of the month and be a minimum of 30 days.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Oceanfront Overlook 2 Bdrm premiere monthly keys style with resort amenities

Key West, Florida, United States

Bed

Bath

Sleeps

$1462.5

THE PROPERTY: This home’s Key West charm and modern amenities make for a wonderful stay. From the Adirondack chair front porch to the private backyard pool, you will quickly fall into the island vibe in this home. A mix of historic Dade County pine and gentle white walls adds to the allure of this home. brbrAs you enter the first floor and look beyond the rich staircase, the contemporary kitchen with butcher block island is sure to catch your eye. Stainless steel appliances and open shelving keep this space bright and airy. You will find all the equipment you need to prepare your meals, as you enjoy conversations in the open concept layout. The cool and comfy living room with large TV and plenty of seating for family and friends, leads to your private pool. Enjoy a dip or keep an eye on the kiddos from the covered porch. With sunshine and loungers, you are sure to enjoy this backyard oasis. A gas grill is available for your use, or you may walk to the many restaurants in the neighborhood. brbrThe first floor also includes a convenient half bath as well as a sunny king bedroom with ensuite bath and walk in shower. A dresser, nightstands, closet, ceiling fan and TV will make you feel at home. Follow the Dade County pine staircase to the second floor where you will find the remaining three ensuite bedrooms. The twin bedroom with ensuite bath and vaulted ceiling is charming and has plenty of space for your family. The beds cannot be joined to form a king, but your children will enjoy having their own beds. The other two king bedrooms have ensuite baths with walk in showers, bedside tables, lamps, and natural light. brbrShould you need additional space for wedding guests or a family reunion, Grand Maison may be rented together with Petite Maison. Together, both properties sleep a total of 12 guests and boast 6 ensuite bedrooms. Please see Maisons de Luxe to rent both homes. brbrBED CONFIGURATION: Grand Maison has four bedrooms, each with its own ensuite bathroom and TV. The first-floor king bedroom is perfect for family members who prefer single floor accommodations. There are 3 equally beautiful bedrooms on the second floor. One bedroom has two twin beds (cannot be joined together) and the other two bedrooms have king beds. brbrOUTDOOR AMENITIES: Private saline pool with water feature surrounded by sunshine, palm trees and lounge chairs. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. A comfortably furnished outdoor porch and gas grill are available just steps outside the double sliding glass doors. In addition, enjoy coffee on the covered front porch or people-watch from the second-floor covered balcony. brbrPARKING: There is parking for one car however, from this convenient location, you may find yourself touring Key West on foot. brbrLOCATION: The home is on the southern end of Duval Street near cafes and night clubs. You can walk to many attractions including the Southernmost Point and the Key West Butterfly and Nature Conservatory. brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home. brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~ GRAND MAISON ~ Spacious home on Duval St with pool and 4 ensuite bedrooms.

Key West, Florida, United States

Bed

Bath

Sleeps

$409.51

**This home is available in August only as a monthly rental (28 nights in the same month).** Come and live like a local! brbrTHE PROPERTY: Enjoy fresh air and sunshine from your front porch or backyard hot tub at Casablanca Too. This unpretentious home has been beautifully updated and is ready to welcome you. The living room looks out to the covered front porch and has lots of natural light, large screen, TV, cool wall AC and a comfy slip-covered sofa. The room is adorned with new lighting and two gorgeous swivel club chairs that allow you to converse with family and friends or turn to watch TV. If you need to work from home, the new fold-down console has plenty of room for your laptop and when done, you can fold it back to its original size. New hardwood floors adorn the home, making it easy to keep clean. brThe cozy updated kitchen has outdoor access and is complete with all that you need to prepare meals or snacks. New appliances include a stainless-steel refrigerator and range. Just outside the kitchen you will find the new dining area furniture with seating for four and boho lighting. brThe spacious king bedroom with wall mounted TV, wall AC and new furniture includes dual night stands with storage, bedside lamps, and a beautiful white headboard. French doors lead out to your private hot tub. The ensuite bath includes a pedestal sink, open storage shelves and tiled stall shower with glass door. New patio furniture and a sun shade adorn your backyard oasis. Start your day with coffee on the covered front porch. Take your bike or walk to Duval Street and enjoy all the excitement that make Key West unique. When you are done for the day, come home and enjoy dinner on the grill and a hot tub massage in a peaceful part of town!brIf you are vacationing with another couple or family, you may rent the other side of this duplex which sleeps four and has a private pool. Look up Casablanca to do this individually or look up Casablanca Grande” to rent both sides of this duplex home simultaneously.brbrBED CONFIGURATION: Enjoy your spacious king size bed and ensuite bath, with wall AC. brbrOUTDOOR AMENITIES: From your bedroom, you can open the French doors and step out to the backyard’s lush foliage and private hot tub. You will also enjoy the new outdoor dining set, umbrella, and gas grill. Your own washer and dryer may be found in the outdoor area near the hot tub.br brPARKING: This home includes off street parking for one car. brbrLOCATION: Historic Old Town, North of Truman Avenue and close to The Meadows, a residential district. Walk to Duval Street in 15 minutes or take a 5-minute bike ride to Higgs Beach or the Southernmost Point. Fausto’s Food Palace, The Best Coffee in Town, Bayview Park, and the Key West Cemetery are also just a short walk away.brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property.brbr***Staying for a month or longer Request a quote for a minimum of 28 nights to see our discounted monthly rates.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location.

Key West, Florida, United States

Bed

Bath

Sleeps

$421.37

Anchor Drop – Oceanfront Escape in Key WestbrbrWelcome to Anchor Drop, a beautifully renovated two-bedroom condo in the exclusive 1800 Atlantic Condominiums. Located just minutes from Duval Street and steps away from the soft sands of Smathers Beach, this serene getaway combines tropical charm with upscale comfort.brLocation Highlights:brbr Oceanfront, gated communitybr Minutes from Duval Street nightlife and diningbr Steps to Smathers Beach & bike-friendly pathsbrbrInside the Condo:brbrLiving & Diningbrbr Cozy living room with ocean viewsbr Plush sofas, large-screen TV, and queen sleeper sofabr Dining area seats six comfortablybrbrSleeping Arrangementsbrbr Primary Bedroom: King bed, en-suite bath, ocean viewsbr Guest Bedroom: Two twin beds (convertible to king), garden & ocean viewsbr Living Room: Queen sleeper sofabrbrBathroomsbrbr Two full bathroomsbr Walk-in shower and dual-sink vanity in the primary bathbrbrKitchenbrbr Fully stocked with stainless steel appliancesbr Dual coffee maker, beautiful countertops, and everything needed to cook & entertainbrbrBalconybrbr Private balcony with lush courtyard and partial ocean viewsbr Perfect for morning coffee or evening winebrbrResort-Style Amenities:brbr Heated Olympic-size pool and 20-person hot tubbr Three tennis courts, including Key West’s only clay courtbr On-site fitness center, sauna, and librarybr Covered pavilions with grills for outdoor diningbr Private beach area plus access to Smathers BeachbrbrParking:brbr One assigned garage parking spot (height restrictions apply)brbr Limited outside guest parking (first-come, first-served)brbrConcierge Services:brbrLet us help you plan the ultimate Key West experience:brbr Bike, scooter, and golf cart rentalsbrbr Excursions: snorkeling, jet skiing, parasailing, kayaking & morebrbr Pre-arrival grocery stockingbrbrbrCancellation Policy:brbr Full refund minus $250 fee if canceled 30+ days before check-inbrbrAnchor Drop is your peaceful paradise by the sea—ideal for families, couples, or friends looking to relax in comfort while being close to everything Key West has to offer.brbrBook your stay now and drop anchor in paradise. brbrBook Activities /keywestattractionsfishingdiving/brbrPlease note Elevation Modernization project June - September 2026 - There will be one operational elevator in each building. brWork will take place daily from 8 am - 6:30 pm

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West, Florida, United States

Bed

Bath

Sleeps

$2168.85

THE PROPERTIES: With plenty of space in an ideal location, Maisons de Luxe combines a large two-story home with a stylish two-story cottage. Family, friends, or wedding guests will appreciate being together yet apart in this smart setting. If you need less space than Maisons de Luxe offers, each property may be rented separately. brbrGRAND MAISON (The Main House): Just beyond the staircase, an open concept living room and kitchen will excite you. Equipped with everything you need to prepare meals in a comfortably furnished home, you will enjoy entertaining guests at Grand Maison. An indoor-outdoor living space spills onto the covered porch and saline pool. Swim in the sunshine, lounge by the pool, or keep an eye on the kiddos from the shaded lanai…the options are endless. brbrThe first floor of Grand Maison also includes an ensuite king bedroom and a convenient half bath. The second floor includes three ensuite bedrooms. The twin bedroom with ensuite bath and vaulted ceiling is a charming space for your children. The other two bedrooms have ensuite baths with walk in showers, bedside tables, lamps, and natural light. This is the Key West lifestyle you have dreamed about. brbrPETITE MAISON (The Cottage): Your vacation begins on the second floor of this cottage with an inverted floorplan. A second-floor open concept living room peers into the petite yet mighty kitchen. The living room’s French doors open out to a comfortably furnished covered veranda. Enjoy outdoor dining or relaxing with a cocktail in the tropical breezes. On the first floor you will find two beautiful king ensuite bedrooms as well as a stackable washer and dryer. This unique home’s mix of white walls, wood accents and stylish art, will help you appreciate the Key West vibe. brbrBED CONFIGURATION: Grand Maison has four bedrooms, each with its own ensuite bathroom and TV. The first-floor king bedroom is perfect for family members who prefer single floor accommodations. There are 3 equally beautiful bedrooms on the second floor. One bedroom has two twin beds (cannot be joined together) and the other two bedrooms have king beds. Petite Maison has two king bedrooms with ensuite baths on the first floor. When rented together, Maisons de Luxe has a total of 6 bedrooms. brbrOUTDOOR AMENITIES: Grand Maison offers a private saline pool with water feature surrounded by sunshine, palm trees and lounge chairs. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. A comfortably furnished outdoor porch and gas grill are available just steps outside the double sliding glass doors. Enjoy the covered front porch and second floor balcony. Petite Maison offers a second floor comfortably furnished covered veranda. When rented together, you can enjoy all the amenities at Maisons de Luxe!brbrPARKING: There is parking for two cars however, from this convenient location, you may find yourself touring Key West on foot. brbrLOCATION: The homes of Maisons de Luxe are located on Duval Street and an adjacent Lane. Both homes are on the southern end of Duval Street near cafes and night clubs. You can walk to many attractions including the Southernmost Point and the Key West Butterfly and Nature Conservatory. brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry- no cats.brbrSMOKING: This is a non-smoking home. brbr**Guests must be 25 years of age or older unless accompanied by an adult.brbr**Managed by Historic Key West Vacation Rentals.

~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Pool ON DUVAL.

Key West, Florida, United States

Bed

Bath

Sleeps

$260.56

**Beginning 12/22/25, Seas the Day! will be a MONTHLY RENTAL (28 nights within the same month). Stay a month and live like a local!brbrTHE PROPERTY: This 2-bedroom 1 bathroom condo with an oversized shared pool is a wonderful place to kick back and relax after exploring the island. Located near the excitement of Duval Street yet tucked back near the water, this tree-lined community is in a perfect location. For history buffs, the Truman Annex is where the winter White House of President Harry Truman is located. brbrEnjoy morning coffee on your covered front porch with seating for two. Inside, the cozy kitchen with pass-through to the dining area has everything you need to prepare meals or midnight snacks. Stainless steel appliances and solid-surface countertops complete the space. The living room has plenty of seating and a large screen TV. Each queen bedroom is decorated in shades of navy blue and white and adorned with nightstands, bedside lighting, and closet storage. The bathroom has a white vanity and walk in, travertine tiled shower. This condo includes your own washer and dryer. French doors lead out to the private patio area with a dining table and chairs, gas grill and loungers. brbrYour island options are endless. Sit back and enjoy the sunshine and a dip in the shared pool. Revel in a stroll through the lushly landscaped community. The Annex also leads to a waterfront park, playground, and amphitheater. Walk to Fort Zachary State Park’s sandy beaches and turquoise waters. Or enjoy a short walk to shops, restaurants, and bars. Either way, Seas the Day!br brBED CONFIGURATION: Each bedroom has a queen size bed and shares the full bath. brbrOUTDOOR AMENITIES: The Shipyard has an oversized shared pool for its guests with plenty of lounge chairs for sunbathing. Your condo has a private patio with dining table and chairs, loungers, and a gas grill. brbrPARKING: A designated parking spot comes with this condo. Please note that the vehicle’s size may not exceed 18’long by 80” wide and that this is strictly enforced. brbrLOCATION: The Truman Annex is in Old Town and faces Southard Street, in Key West’s premiere gated waterfront community. brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly).brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Managed by Historic Key West Vacation Rentals.***

~ SEAS THE DAY ~ Nestled in a gated community by Fort Zachary Taylor beach!

Key West, Florida, United States

Bed

1

Bath