Vacation Rentals By Owner In Key West, FL

Road's EndbrbrStep into Road's End, your inviting retreat just steps from Duval Street, where the charm of Old Town Key West meets peaceful garden living—perfect for travelers seeking a relaxing escape in the heart of the island.brbrThe Space:brRoad's End offers a welcoming two-level layout designed for comfort and convenience. The lower level features a cozy living area with a queen sleeper sofa for additional guests, a convenient half bath, and a fully equipped kitchen with modern appliances for easy at-home dining. Upstairs, the spacious king bedroom provides an inviting escape complete with a dedicated workspace, ample storage, and a full ensuite bathroom. With natural light, tasteful coastal décor, and all the essentials for a relaxing stay, this townhome delivers a warm and comfortable home base for your Key West adventure.brbrGuest Perks:brTake advantage of easy contactless check-in with a personalized access code provided before arrival. Guests also enjoy shared access to a beautifully landscaped courtyard featuring a heated outdoor plunge pool, onsite laundry, and peaceful outdoor seating areas perfect for enjoying the island breeze.brbrNeighborhood Highlights:brPerfectly situated just off the southern end of Duval Street, Road's End places you within walking distance of the Southernmost Point, the Hemingway Home, the Key West Lighthouse, and beloved local restaurants including Blue Heaven, Moondog Café, Rams Head Southernmost, and Better Than Sex Dessert Restaurant. From charming cafés to iconic landmarks, everything Old Town has to offer is just moments away.brbrGetting Around:brExplore the island with ease—walk to many nearby attractions, or rent a bike, scooter, moke, or golf cart for added convenience. Rideshares, taxis, and pedi-cabs are also readily available. Street parking is available in the area on a first-come, first-served basis.brbrOther Things to Note:br- Pet-Friendly! Up to 2 dogs (40lbs maximum) with a $20 per pet per night fee.br- Onsite shared washer/dryer in unit.br- Shared heated plunge pool located in the courtyard.br- Guests must be 25 years of age or older to reserve this property.br- The primary bedroom is located on the second floorbrbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, pool, parking areas, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.brbrTo promote guest safety, exterior security cameras are in place around common outdoor areas including pathways, entrances, and the courtyard. No cameras are located inside the home or in private spaces.

Road's End | Prime Old Town Location! Updated Home w/ Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$362.79

The Orchid Suite is a bi-level suite decorated in a rich contemporary Danish style. The bedroom is located upstairs with a bookcase divider separating two different sleeping areas, each with a queen bed. The upstairs bathroom features a tiled shower with a glass door, hairdryer, and all necessary linens. Large beach towels are also provided.brbrDownstairs is a living room There is a lovely dining room with plenty of seating, a tiled breakfast bar, and stools. We have recently added a new half bath.brbrAll the amenities of a luxury property are included: a fully equipped kitchen, dishwasher, refrigerator with ice-maker, microwave, drip coffee maker, blender, and everything needed to prepare, and serve a gourmet meal. There are two shared gas BBQ grills, coin-operated washer/dryers, and on-street parking.brbrOrchid Suite is a half-block from the famous Duval Street, just a short walk to the infamous night life. Several blocks away is the sunny South Beach with ocean swimming and a restaurant. If you prefer a pool, it is onsite and just a few steps away from the cottage.brbrOrchid Suite is bi-level, with the bedroom upstairs. It may not be suitable for persons unable to climb stairs well.brbrParking in Key West is very limited. This property has no assigned parking and is street parking only. You are responsible for finding parking for your vehicle. The maximum number of people allowed in this property is 4. If there are more than 4 people are in your party upon arrival, your party will be asked to leave without compensation. Violation of ANY house rules will result in your party being asked to leave without compensation.

Orchid Suite on Center St - 1/2 block from Duval Sleeps 4

Key West, Florida, United States

Bed

Bath

Sleeps

$321.12

The Bonaire Suite is a bi-level suite decorated in a rich contemporary palm tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door.brbrDownstairs is a living room with sofa that converts to a queen bed and a comfortable love seat. The large dining room easily seats six people. There also is a recently-installed half-bath on this floor for your convenience. Outside your door is a delightful, tropically landscaped courtyard with singing birds. This unit is so comfortable and special that you might not want to leave. But if you do, the Duval Crawl and famous Key West nightlife begins just a half-block away. Outdoor table and chairs overlooking the gardens are perfect for a romantic evening or a great place to meet your neighbors.brbrWithin several blocks, at the end of Duval Street, is South Beach, with access to ocean swimming and an open-air restaurant and bar. If you prefer to take a quick dip, head over to the shared pool or work on your tan in the lushly landscaped courtyard right outside your door!brbrNote: Parking in Key West is very limited. This property has no assigned parking, although free street parking is available. You will be responsible for finding parking for your vehicle. brbrThe individual making the reservation must be 25 years or older with proper identification and be an occupant of the property. The maximum number of people allowed in this property is 6. If there are more than 6 people are in your party upon arrival, your party will be asked to leave without compensation.brViolation of ANY house rules will result in your party being asked to leave without compensation.

Half block to Duval - Stay at the Bonaire Suite

Key West, Florida, United States

Bed

Bath

Sleeps

$490.45

A Caribbean Alternative is a wonderful vacation townhome located in the desirable Truman Annex area of downtown Key West. This townhome provides convenient access to all the exciting activities and world-class eateries and bars offered in downtown Key West. We encourage you to leave your car at home and enjoy walking, biking, or scootering to almost anywhere you want to go.brbrThis lovely 2 bedroom, 2 1/2 bath townhome is nicely appointed with stainless steel appliances, a washer and dryer, and a covered outdoor seating area. The living area has homey seating with a flat screen television and Bose sound system. The French doors open up onto the covered deck and cleanly landscaped yard. brbrUpstairs are two bedrooms, both with ensuite bathrooms, queen beds, and ample closet space. Both bedrooms open to a covered porch with relaxed seating options. A washer and dryer are located in the hallway between the 2 bedrooms for your convenience. brbrThe Truman Annex Waterfront Park is close by with walking paths, open areas to play or relax, and a splash pad and park for the kids to play. Fort Zachary Taylor State Park and Beach are also close by and offer picnic areas with grills, as well as beach areas that are ideal for snorkeling and sunbathing. There are chairs and umbrellas for rent as well as a full concession stand and restrooms.brbrEnjoy the quaintness of this peaceful neighborhood on your next visit to Key West and be close to all there is to do on our beautiful island. brbrThis is a weekly rental. brbrOnly one parking space is provided for this unit -parking can be difficult - no trucks/campers or oversized vehicles.brbrSorry, no pets allowed per the HOA

A Caribbean Alternative townhome in Truman Annex

Key West, Florida, United States

Bed

Bath

Sleeps

$346.08

Located in the heart of historic Old Town Key West, just steps away from world-renowned Duval Street, La Casa de Luna is a ground-level one-bedroom, one-bathroom condo that is part of a large house with a relaxing veranda. This modern property is within easy walking distance to all your favorite restaurants and bistros.brbrOpen the door to the full kitchen offering a refrigerator, stove/oven, microwave, and coffee maker. Your group's chef can keep up the chatter with friends or family sitting in the living room with La Casa de Luna's open floor plan. There is a queen sleeper sofa in the living room, so it will accommodate up to four people. The full bath comes supplied with all the amenities you need, including plush towels and wash cloths. brbrThe primary bedroom features a comfortable king bed and two nightstands for the late night reader. Walk out onto the porch from the bedroom with a cup of coffee or margarita to enjoy people watching! brbrPLEASE NOTE THAT THIS PROPERTY DOES NOT HAVE A POOL.brbrYou may use the pool at Dante’s if you utilize their food and beverage services or you may purchase a day pass using the link below at any of the hotels located near your rental. br brhttps://www.resortpass.com/s/us/fl/key-west/pool search_term=Key+West%2C+Florida&city_alias_id=26brbrParking in Key West is very limited. This property has no assigned parking and is street parking only. You are responsible for finding parking for your vehicle. The individual making the reservation must be 25 years or older with proper identification and be an occupant of the property. The maximum people allowed in this property is 4. If there are more than 4 people are in your party upon arrival, your party will be asked to leave without compensation. Violation of ANY house rules will result in your party being asked to leave without compensation.

La Casa de Luna - 1 Bd/1B condo just off upper Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$384.19

The perfect space in the perfect place.brbrA quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard section of the Truman Annex, it is perfectly located steps from Duval street, Mallory Square, Zachary Taylor State Beach, Truman Waterfront Park, Bahama Village and all the best that Key West has to offer.

The Palms...A beautiful space in the perfect place.

Key West, Florida, United States

Bed

Bath

Sleeps

$697.46

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThis modern Old Town condo is designed for the real downtown experience in the Conch Republic, ideal for anyone looking to indulge in Key West’s famous late night scene. VILLA ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district. Although this property does not include parking, you couldn't be any closer to the late-night scene and attractions of downtown. Fair warning... It can get a little noisy out there! This tropical three-bedroom retreat is hidden within a renovated Old Town home, with all of the charm of the famous conch houses of Key West.brbrTHE LIVING AREA...brbrVILLA ANGELITA is the second floor of this converted Old Town home. As you enter the apartment by climbing the stairs from the front door of the home, you are greeted with modern tropical decor in the light-filled living room. Tall ceilings and high end finishes complete this renovated condo. A large flat screen TV on the wall overlooks the spacious living area with plenty of seating. The sofa pulls out to a full sized bed to sleep an extra guest in a pinch.brbrTHE KITCHEN...brbrOff of the living area, the upscale kitchen is fully equipped with all the high-end tools and appliances you'll need to whip up a meal at home. If you can resist the temptation of all of the famous Key West restaurants within walking distance, that is! The dining area off the kitchen seats six by the windows for a relaxing evening in or can be used as your stay at home office in Paradise (high speed, password-protected WiFi included.) The front and back of the condo have doors to the wrap-around decks for you to enjoy your morning coffee and some prime Old Town Key West people watching.brbrTHE ACCOMMODATIONS...brbrThe accommodations of VILLA ANGELITA are designed to accommodate a family or several couples comfortably. brbr• Master Bedroom: Queen bed, overhead fan, flat screen TV, and an en-suite bathroom with a glass shower. brbr• Second Bedroom: Queen bed, overhead fan, flat screen TV, and direct access to the wrap around deck. brbr• Third Bedroom: King bed, overhead fan, flat screen TV, and direct access to the wrap around deck. brbrThere is a shared full bathroom in the hallway for the Second and Third bedrooms, with a glass shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen Cable TVs in Living Room and All Bedroomsbr• Fully-Equipped Kitchenbr• Basic stock of spicesbr• Starter supply of paper productsbr• Starter set of cleaning productsbr• Linens and Towels providedbr• Wireless high-speed Internet access and full cable is includedbr• Full Time Concierge ServicebrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 7 adultsbr• Pets Considered - Max of 2 allowed and if approved an additional fee of $200 per pet will applybr• This home does not include designated parkingbr• 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.

**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

7

Sleeps

$333.55

The Hollinsed House's 2nd Floor Victorian Delights has a queen bed, large living room (with futon), dining area and remodeled kitchen, high ceilings, bright sunshine and many windowsbrAll of our units offer you free access to Wi-Fi since we know you need some of the pleasures from back home. We know you'll enjoy your stay with us. Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon as you enjoy the wonderful weather that Key West offers!! We offer spacious rooms and suites that are designed to fit anyone's budget and taste.brbrOur off street parking is limited to 2 cars total. If the parking spaces are already taken, you may park on either side of the street, as we are located on a ONE way street. Please do not park in spaces marked RESIDENTIAL PARKING (it is painted on the pavement in white letters) unless you have Monroe County license plates and a Key West Parking Permit sticker. You risk the chance of being ticketed. Please be courteous and do not block anyone's driveway.

Apartment

Ensuite Quad at The Hollinsed House

Key West, Florida, United States

1

Bed

1

Bath

Sleeps

$615.63

Atlantic Cabana | Luxury 3-Bedroom Townhome Steps from the OceanbrbrEscape to the beauty and tranquility of Key West at Atlantic Cabana, a stunning 3-bedroom, 3-bathroom townhome offering 1,950 sq. ft. of contemporary living space. Built in 2007, this stylish corner townhome features top-of-the-line finishes and a prime location just steps from the Atlantic Ocean, pristine beaches, and nearby attractions. Whether you're soaking up the sun at the beach or relaxing in your private pool, Atlantic Cabana is the perfect destination for an unforgettable island getaway.brbrThe Ambiance:brFrom the moment you step inside, you'll be greeted by an open-concept design, filled with natural light and modern touches. The spacious layout is perfect for both family vacations and group gatherings, with ample room for everyone to unwind and enjoy. High-end materials such as stainless steel appliances, granite countertops, and hardwood floors elevate the home's chic, beachy vibe, while the private pool and deck area invite you to enjoy the outdoors in complete privacy.brbrHighlights include:br- A fully equipped kitchen with stainless steel appliances and a large kitchen island ideal for preparing meals and entertainingbr- A private, heated pool and outdoor deck perfect for relaxing or hosting friends and familybr- Three beautifully appointed bedrooms, including two king-sized beds and a queen-sized bedbr- Three bathrooms featuring modern finishes, with two en-suite and one shared bathbr- Shaded balconies off each upstairs bedroom with peaceful views of the neighborhood and the poolbrbrGuest Access:brAtlantic Cabana offers complete convenience with private off-street parking, including space for two cars in the driveway, plus free street parking available at all times. The townhome is fully furnished, and a stackable washer and dryer is located on the second floor for your ease. We also provide detergent and dryer sheets to get you started, so you can pack light and focus on enjoying your vacation.brbrLocation Highlights:brNestled in the quiet Mid Town area of Key West, Atlantic Cabana is located just a few blocks from Higgs Beach and the White Street Pier. Nearby you'll find the Indigenous Park, a popular dog park, and a variety of outdoor activities including volleyball and pickleball courts. Whether you're biking or driving, you're just a short 5-minute drive or 10-minute bike ride from the iconic Duval Street, where you can explore the island's lively nightlife, world-class restaurants, and unique shops.brbrTransportation Tips:brGetting around Key West is a breeze from Atlantic Cabana. With private parking for up to two cars, you can easily explore the island by car or bike. For further convenience, there are also taxis and rideshare options available, as well as public transportation to help you explore all that Key West has to offer.brbrOther Things to Note:br- Central air conditioning for ultimate comfort during your staybr- On-site off-street parking for your conveniencebr- Washer and dryer available for guest usebr- Mid-stay cleaning available upon requestbr- A minimum stay of 30 days is required, in accordance with local regulations.br- Guests must be 25 years of age or older to reserve this property.brbrCheck-in time is 3:00 PMbrCheck-out time is 11:00 AMbrbrAt Colocada Vacation Rentals, we are dedicated to providing a luxurious and memorable Key West experience. If you have any questions or need assistance during your stay, our friendly local team is available to ensure your vacation is everything you dreamed of and more!

Atlantic Cabana | Luxury 3-Bedroom Townhome Steps

Key West, Florida, United States

Bed

Bath

6

Sleeps

$366.25

Starfish Oasis at Casa Marina offers 2BR, heated & chilled pool, hot tub, private parking for 2 large vehicles, pet-friendly, and just an 8-minute walk to the beach.brbrThis home is only available as a MONTHLY RENTAL with 28 NIGHT MINIMUM. Booking is by the calendar month (first day of the month to the last). Alternate dates may be considered if the calendar/occupancy allows.brbrStarfish Oasis at Casa Marina – Garden-Level Poolside Retreat is a tropical paradise located in one of Key West’s most coveted residential neighborhoods. This completely renovated duplex home offers the entire private downstairs residence with two bedrooms, two full bathrooms, a spacious open-concept living area, and a fully equipped kitchen—ideal for couples, friends, or small families seeking an authentic island escape.brStep outside to a lush shared tropical outdoor space featuring a one-of-a-kind sailboat cocktail swimming pool, hot tub, outdoor bar with TV, and a commercial outdoor chef’s kitchen designed for relaxed evenings and effortless island living. Comfortable seating areas and a large two-person hammock create inviting places to unwind beneath the palms.brbrThe Space:brThe Garden-Level Poolside Retreat is thoughtfully designed for comfortable extended stays, easygoing Key West living, quality time, and relaxed entertaining.brThe open living area reflects authentic Key West style, perfect for reading, relaxing, or planning your next adventure. A dedicated work nook offers a quiet and comfortable spot for remote work or trip planning.brThe primary bedroom features a private en suite bathroom, while the second bedroom is located adjacent to a second full bathroom, providing privacy and comfort for all guests. Both bedrooms offer excellent sleep quality and feature separate exterior entrances, making it easy to step out for an evening soak in the hot tub.brThe fully equipped indoor kitchen includes all the essentials for everyday cooking, while the commercial outdoor kitchen is a true chef’s delight for effortless island dining. A Weber grill, Traeger smoker, and Big Green Egg create an exceptional setup for outdoor cooking enthusiasts.brFull-size, in-unit laundry facilities are provided exclusively for guest use.brEvery detail blends modern comfort with tropical charm, creating an inviting atmosphere that encourages guests to slow down, settle in, and live like locals. High-speed internet and keyless entry ensure a seamless and convenient stay.brbrGuest Access:brGuests enjoy exclusive access to the entire downstairs residence, including the bedrooms, bathrooms, living area, kitchen, and laundry facilities.brThe outdoor space is shared only with the upstairs residence and is never open to the public, allowing guests to fully relax and enjoy a private, resort-style setting.brSelf check-in is simple and seamless with a personalized access code prior to arrival, along with direct contact information for the local owner/manager, who may be in residence onsite occasionally but respects your privacy at all times. Host is available for questions, assistance, or local recommendations throughout the stay. brbrThe Neighborhood:brCasa Marina is one of Key West’s most desirable residential neighborhoods, known for its understated elegance, historic island homes, and close proximity to beaches and Old Town. Guests enjoy quiet, palm-lined streets and a refined, peaceful setting that makes it easy to experience the island like a local—returning each day to a calm, comfortable retreat away from the crowds.brbrExplore & Dine Nearby:brEnjoy sunrise or sunset walks to White Street Pier or the Southernmost Point. Higgs Beach is just a short distance away and offers chair and umbrella rentals, kayaks, and stand-up paddleboards. Nearby amenities include bocce ball courts, tennis, pickleball, and volleyball courts, as well as a dog park and children’s playground. Explore the historic West Martello Tower and botanical gardens, or enjoy local dining favorites such as Louie’s Backyard, Salute! on the Beach, and White Street Pizza.brGuests are always welcome to ask their local host for personalized recommendations and insider tips to truly live like a local.brbrGetting Around:brThe driveway provides parking for up to full-sized two vehicles. Golf carts, scooters, and bicycles are popular and convenient ways to explore the island, and Uber service is readily available.brbrOther Things to Note:brDogs are welcome with PRIOR approval only. A maximum of two dogs is permitted. A $250 pet fee per stay applies. Dogs must be well-behaved, house-trained, and not disturb neighbors. Guests are responsible for all cleanup inside and outside the property. Some breed restrictions apply. Failure to disclose pets may result in additional fees or cancellation.

Starfish Oasis at Casa Marina, 2BR - Heated Pool - Hot Tub - 2 Parking - Pets OK

Key West, Florida, United States

Bed

Bath

Sleeps

$288.55

The ShangriLa Suite on the 1st floor of the Carriage House building at the Hollinsed House is a large deluxe studio with a queen bed, living area, bath and kitchen that is tucked away for privacy with its own private courtyard.brAll of our units offer you free access to Wi-Fi since we know you need some of the pleasures from back home. We know you'll enjoy your stay with us. Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect setting for a laid back and quiet afternoon as you enjoy the wonderful weather that Key West offers!! We offer spacious rooms and suites that are designed to fit anyone's budget and taste.brbrOur off street parking is limited to 2 cars total. If the parking spaces are already taken, you may park on either side of the street, as we are located on a ONE way street. Please do not park in spaces marked RESIDENTIAL PARKING (it is painted on the pavement in white letters) unless you have Monroe County license plates and a Key West Parking Permit sticker. You risk the chance of being ticketed. Please be courteous and do not block anyone's driveway.

Apartment

Queen Ensuite at The Hollinsed House

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastefully decorated 2 bedroom, 1 bath condo with views of the pool. The master bedroom has a queen sized bed; the 2nd bedroom has 2 twin beds. The remodeled bathroom has a walk in shower enclosure. The fully equipped kitchen opens to the front porch which overlooks the pool area. This covered porch offers protection from the hot Key West sun as well as the occasional tropical shower. The back porch is great for sunbathing & star gazing! All is provided to make your stay enjoyable including high speed internet, blender, beach towels, and washer/dryer. So grab a cool drink and a towel and head down to your lounge chair by the pool! brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Green Spot at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$205.57

IDEAL LOCATION IN GREAT COMMUNITY...brEnjoy your stay at the President's Walk at Truman Annex. This well manicured community is set in a wonderful location which is walking distance to most that Key West offers! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrFURNISHINGS...brThe first floor includes a living room, dining area, fully equipped kitchen and a half bath. The sitting area has a comfortable sofa and coffee table situated to view out of the 2 sets of French doors. The dining table is centrally located for meals, playing cards or just enjoying each others company.brbrSLEEPING ARRANGEMENTS...brThe second floor is outfitted with two bedrooms. The master bedroom has a comfortable queen size bed, a closet for hanging, dresser for storage and a French door which leads out to a small deck with seating. There is Roku TV available only in the master(downstairs has cable). There is also a half bath with a toilet and sink en suite. The guest room has a queen size bed, a large closet and a door leading to a deck. In the upstairs hall you will find the full bathroom. There is a large double vanity and a shower with enclosure. brbrPOOL AND OUTDOOR LIVING...brOpen the French doors and step onto the patio to relax. There is a grill ready to cook your fresh catch so you can dine outside under the stars. The heated community pool is just a short walk from the home and this Old Town location is conveniently situated near Duval Street, waterfront sunsets at Mallory Square and locals favorite beach at Fort Zachary Taylor.brbrPETS...brThis is not a pet-friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrPARKING...brThis home comes with an assigned parking space. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property.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).brbrNO TIME LIKE ISLAND TIME...

BELLA VITA ~ 2/1.5 located in the Truman Annex with a community pool!

Key West, Florida, United States

Bed

1

Bath

Sleeps

$858.0

Looking for the perfect spot to soak up some sunshine and unwind in Key West You’ve found it. Island Pearls is a stylish and comfy 2-bedroom, 2-bath vacation rental located right on charming Fleming Street—just one block from all the action on Duval and directly across from the local favorite, Fausto's grocery store. You’ll be close to everything, so no need for a car (though there’s a driveway if you have one).brbrStep inside and you’ll feel instantly at home. The kitchen is modern and fully equipped, with sleek white finishes and custom cabinets that keep everything looking clean and polished. Whether you’re whipping up breakfast or sharing cocktails at the island, it’s a space that makes cooking and gathering easy and fun.brbrThe living area is cozy yet modern, with hardwood floors, comfy seating, and just the right amount of Key West charm. Throw open the plantation shutters and let in that sweet Florida sunshine—it’s the perfect spot to kick back after a day of exploring.brbrBoth bedrooms are en-suites, thoughtfully designed with comfy beds, soft linens, and fun, tropical wallpaper that’ll remind you you’re on island time. Each has its own private bathroom, making it great for couples, friends, or a small family traveling together.brbrOutside, the private pool and deck are where you’ll probably spend most of your time. Whether you’re sunbathing, taking a dip, or just enjoying the breeze with a drink in hand, it’s a peaceful spot that feels like your own slice of paradise.brbrIsland Pearls is all about comfort, convenience, and that laid-back Key West vibe. It’s not just a place to stay—it’s a place to relax, recharge, and make some great memories.brbrP.S. The pool is all yours—no sharing here! Pool heat available when requested. brbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.

Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath

Key West, Florida, United States

Bed

Bath

Sleeps

$362.17

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: As you enter the home via its white picket fence and comfortable front porch, you will be uplifted by sunshine. Hardwood floors and high-end finishes are reflected in this home while a bit of Key West charm is revealed. A first-floor queen bedroom is on your left and just two steps down into the home is one of three full baths. Moving on into the oversized wet bar area and living room, you can cozy up on the sofa or chairs and watch a little TV while sipping on your wine. This beautiful space includes blue/grey cabinets, a sink, open shelving, storage, and a laundry room. Looking out through the double sets of French doors, you will enjoy the lush vegetation that surrounds this home. Moving back towards the chef’s kitchen with slide in gas range and custom hood, you have all you need to prepare a gourmet meal or simply heat up a take-out meal. A Sub-zero refrigerator and stainless-steel appliances are complemented by white upper cabinets and beautiful natural wood lowers. Quartz counters, a double oven and built in microwave enhance this room. As if that isn’t enough space, moving further towards the rear of the home and pool, is a dining room with seating for six as well as a half bath; this area is open to a cozy family room with built in cabinets, TV, and a fireplace-imagine that! A wall of glass spills out onto the beautiful blue pool area. Enjoy a day or night swim, with plenty of privacy and loungers. Cook up your catch of the day on the outdoor grill. brbrThe second-floor houses two additional bedrooms with access to the porches. The primary king bedroom has a walk-in closet, nightstands, bedside lighting, dresser storage and a TV. Its bath has dual sinks, a glass walk-in shower, and a large soaking tub, perfect for relaxing after a night on Duval Street. The queen guest bedroom has dresser storage, nightstands, bedside lighting, and a TV. The beautiful ensuite bath is tiled and includes a glass walk-in shower. brbrBED CONFIGURATION: The first-floor bedroom has a queen bed. The second floor includes a king bed in the primary bedroom and a queen bed in the second bedroom. brbrOUTDOOR AMENITIES: Lush landscaping provides privacy around the pool with lounge chairs and gas grill. The pool is heated seasonally (November-April) for an additional fee which will be assessed at the time of booking. An outdoor shower completes the Key West vibe!brbrPARKING: There is no designated parking space, but street parking is available throughout the neighborhood.brbrLOCATION: Old Town, north of Truman Ave in a quiet residential area within walking or biking distance of several shops, galleries, and restaurants. 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***

~ASHE HOUSE~ Renovated and relaxing with pool, porches, and privacy!

Key West, Florida, United States

Bed

Bath

6

Sleeps

$993.3

BEDAZZLING COMPOUND...brTwo delightful conch style island homes are situated on one glorious parcel in Old Town, just a stone's throw away from the magic of Duval Street and the historic Seaport. Each home features 3 bedrooms with private bathrooms, as well as their own heated pools. Quintessential charm abounds and captures your island soul, with stunning pathways through lush gardens.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brFront House (PEARL): Enter the Pearl Cottage from its embracing wraparound porch, with ample seating and an invitation to relax and unwind in paradise. Sophisticated island style punctuates this 1279 sq. ft. home, complete with a modern and fully-stocked kitchen that overlooks a cozy living area with couch, love seat, cushioned chair and a smart TV for your viewing pleasure. There is a half bath with a stacked washer and dryer just off the living area for your convenience. These homes are equipped with Roku TV.brbrBack House (AMBER): Enter the newly built two-story Amber Cottage which boasts 1714 sq.ft. of living space. Enjoy a large, state-of-the-art kitchen that houses every appliance and tool needed for your culinary expression. This flows into the plush living and dining areas where you can unwind with loved ones and watch your favorite shows on the wall-mounted TV. Sliding doors open to the backyard oasis and a bedroom with double-entry full bath completes the downstairs space. An upstairs balcony resides on the upstairs landing and overlooks the pool.brbrThese homes have mounted outdoor cameras but are NOT in use during guest stays.brbrSLEEPING ARRANGEMENTS…brFront House (PEARL): There are 3 bedrooms, two with queen beds and one with a king bed, all with private bathrooms with showers, ample storage space and TVs. A sleeper sofa resides in the living room with a powder room nearby.brbrBack House (AMBER): There are 3 bedrooms total. There is a downstairs queen bedroom (Murphy bed) with an office space and double-entry shower bathroom. The other two bedrooms are upstairs (one with a queen bed and the other a king) and ensuite bathrooms with showers and large closets. All upstairs bedrooms enjoy a TV for your late night down time. A sleeper sofa resides in the living room.brbrOUTDOOR LIVING…brLose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. Each home has its own private pool that can be heated in the winter months and plenty of outdoor seating for gazing at the stars and al fresco dining. The rear home (AMBER) comes with a spa and outdoor shower as a great way to end your day in Paradise.brbrPETS...brThese homes are dog friendly only and a pet fee is required. Please include the size and breed in the comments when inquiring and booking. 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...brThere is a driveway that will accommodate 2 vehicles.brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrBRING ALL YOUR LOVED ONES…

JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w/ Private Pools!

Key West, Florida, United States

Bed

Bath

Sleeps

$533.04

AN ISLAND STUNNER...brThis is the back cottage of the delightful Jewel Box Cottages compound, located in Old Town, just steps away from all the Duval Street happenings and the historic Seaport. This two-story gem offers 1714 sq. ft. of authentic island charm, with magnificent hickory hardwood floors throughout and whitewashed interior cypress wood interior walls. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter the home to a gorgeous and spacious contemporary kitchen which is a dream come true for culinary aficionados. This space is well-stocked with every modern appliance and cooking tool you'll need to concoct special meals for loved ones. This space flows into the plush living and dining areas where you can unwind with loved ones and watch your favorite shows on the wall-mounted TV. Sliding doors open to the backyard oasis and a bedroom with double-entry full bath completes the downstairs. A lovely balcony resides on the upstairs landing and overlooks the pool area. This home is equipped with Roku TV. This home has a mounted outdoor camera but is NOT in use during guest stays.brbrSLEEPING ARRANGEMENTS: brThere is a downstairs bedroom with an office space, queen Murphy bed and double-entry shower bathroom. The other two bedrooms are upstairs (one with a queen bed and the other with a king bed), ensuite shower bathrooms and large closets. The larger primary bedroom upstairs houses the washer and dryer in its oversized bathroom and also has a private door to the upstairs balcony. All upstairs bedrooms enjoy TVs. A sofa sleeper lies in the living room.brbrOUTDOOR LIVING…brEnjoy your sparkling heated pool with a waterfall feature, outdoor shower, and lounging chairs. Al fresco dining for 6 will delight your senses as you dine under sultry stars. Lose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. brbrPETS...brDogs 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...brThere is a driveway for this home for 2 vehicles.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).brbrBRING ALL YOUR LOVED ONES…

AMBER COTTAGE ~ Renovated 3 Bedroom, 3.5 Bathroom Home w/ Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$481.81

CONCH STYLE CHARM...brThis is the front cottage of the delightful Jewel Box Cottage compound, located in Old Town, just a stone's throw away from the magic of Duval Street and the historic Seaport. Abundant tropical foliage embraces the wrap-around front porch, inviting you to sit and people watch with your favorite beverage in hand. Wood floors and painted white walls line the space of this 1279 sq. ft. home that features vaulted ceilings and wooden beams and loads of Key West sunshine spills through multiple skylights.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brSophisticated island style greets you as you enter the home which features a beautiful, modern kitchen, complete with island, stainless appliances and everything you'll need to cook for friends and family. The adjacent living/ area offers plush seating with a couch (also a sleeper sofa), loveseat and cushioned chair and smart TV for your viewing pleasure. A stacked washer and dryer occupy the half bath which is located just off the living area. This home is equipped with Roku TV. This home has a mounted outdoor camera but is NOT in use during guest stays.brbrSLEEPING ARRANGEMENTS…brThere are 3 bedrooms, two with queen beds and one with a king bed. All bedrooms come with private en suite bathrooms with showers, ample storage space and two of the rooms include a TV. brbrOUTDOOR LIVING…brEnjoy your covered porch with a beautiful heated pool and outdoor dining for 6 as well as loungers for lazy afternoons. Lose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. brbrPETS...brDogs are permitted and a pet fee is required. Please leave the size and breed in the comments when inquiring or booking. 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...brThis home does not come with parking therefore guests must locate parking on the street in the surrounding neighborhood.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).brbrPICTURESQUE RETREAT…

PEARL COTTAGE ~ 3 Bedroom, 3.5 Bathroom Home with Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$298.74

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: Located less than two blocks from Duval Street, this fully renovated home in Historic Old Town is walkable to many of the island’s attractions, including restaurants, bars, and shops. A 2016 recipient of The Historic Florida Keys Foundation’s Preservation Award, this home has been updated with the modern amenities of a luxury vacation home while maintaining much of its architectural detail. brbrThe inviting front porch is a wonderful place to enjoy morning coffee or people watching. After a day on Duval Street, you will enjoy kicking back and unwinding in the living room with a flat screen TV. A white kitchen with plenty of counter space, cabinets and a farmhouse sink make snack or meal preparation a breeze. Groceries and sundries may be purchased at the unique Fausto’s Market, just a three-block walk or bike ride away. brbrEach bedroom has two closets, night tables and bedside lighting. The primary bedroom has a private entrance and a vaulted ceiling that adds volume to the space. The primary ensuite bathroom has natural light and includes a double vanity and a frameless, walk-in shower. The secondary bedroom includes a charming window seat, perfect for evening reading. Its bathroom has a tub/shower combination, pedestal sink, and a large, frosted window. brbrLight and bright both inside and out, this home is fenced, landscaped, and adorned with a private heated pool with waterfall feature. A covered lanai and decking will inspire you to entertain or dine al fresco. A large retractable awning provides an additional dining space or a respite from the Florida sun. Hardwood floors, central air conditioning, a mini-split in the primary bedroom, and ceiling fans add to the cool convenience of this Key West style home in paradise. brbrBED CONFIGURATION: There is a primary king bedroom, a secondary queen bedroom and a queen sleeper sofa for an occasional guest or children. brbrOUTDOOR AMENITIES: The home is fenced, and the outdoor area is private. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. A covered lanai, loungers, outdoor seating, dining tables, electric grill and a Zen like garden complete the area. brbrPARKING: There is no designated parking however on street parking may be available in the neighborhood. brbrLOCATION: Old Town Key West, just 2 blocks from Duval Street. 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***Guests must be 25 years of age or older unless accompanied by an adult.br***Please note that the cleaning fee includes a full mid-stay clean***br***Managed by Historic Key West Vacation Rentals***

LA CASITA EN CIMA~ Enjoy Key West in this lovely gem with a heated pool.

Key West, Florida, United States

Bed