Vacation Rentals By Owner In Key West, FL

This listing is for a room within a hotel.brbr✦ Your room equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

Serene Resort Room with Private Beach & Spa - Perfect Key West Escape

Key West, Florida, United States

Bed

Bath

Sleeps

$909.03

This listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views

Key West, Florida, United States

Bed

Bath

Sleeps

$763.85

This listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale

Key West, Florida, United States

Bed

Bath

Sleeps

$252.7

**NEW PHOTOS COMING SOON!**br**NEW LISTING**brbrBRING YOUR SANDY FEET AND FLIP FLOPS ...brDive into ultimate island nirvana in this delightful cottage, just right for one or two couples, seeking sweet refuge. The relaxed ambiance of this cozy nest is tucked into an ideal Old Town neighborhood, conveniently located 3 blocks from the quiet end of Duval, a short stroll to Higgs Beach, Southernmost Point, French bakeries and Cuban coffee!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE. THIS IS AN ADULTS ONLY PROPERTY.brThis is a non-smoking property - inside and out.brbrDETAILS AND AMENITIES...brSet back from the street behind a gray picket fence, enter the main house that invites you to drop your bags and sink into pleasing comforts. Savor morning cups of coffee or an evening beverage while you relax on the front porch and immerse yourself in the colors and serenity of the garden. Catch the soothing ocean breezes and fragrant blooming jasmine. Inside, you are greeted by the authentic charm and character of a true Key West abode, complete with Dade County Pine, original Hunter ceiling fans, and mahogany and tile floors. The kitchen is compact but efficient, fully equipped for cooking and baking, and opens to the living room. Enjoy a large desk with work space in the front room. brbrSLEEPING ARRANGEMENTS...brThere are two ground floor bedrooms - one queen bed in the front and one double bed in the back of the house. Both feature ensuite bathrooms with walk-in tile showers, granite-top vanities, and closets. The back bedroom is private and opens directly onto the deck and pool. There is also a treetop suite that is accessed via an outdoor stairway on the deck. It has a double bed with an ensuite bathroom, and can be used as a detached office or studio space. brThis home accommodates 4 people max. brbrOUTDOOR LIVING...brAmple outdoor living space makes this cozy home feel spacious and comfortable. The back deck is visible from inside the home through French doors so that - day or night - you feel connected to the tropical outdoor ambiance. Enjoy your breezy covered porch, overlooking a sparkling pool that is surrounded by lush and soothing greenery. Toss your fresh catch of the day on the BBQ grill and dine al fresco at the large outdoor dining table. brbrPARKING...brThere is not an off street parking space for this home, however curbside parking is always available near the front gate.brbrPETS...brThis is not a pet friendly home.brbrBOOKING DATES...brThis home is offered only 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.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brCancellations 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).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!brbrLOSE YOURSELF ON ISLAND TIME…

ZEN GARDEN RETREAT~NEW! Adult Only 2 BR with Treetop Suite/Writer Studio!

Key West, Florida, United States

Bed

Bath

Sleeps

$788.35

Escape to Your Key West ParadisebrbrWelcome to your home away from home in the heart of beautiful Key West. This spacious 3-bedroom, 3-bathroom retreat combines modern comfort with the laid-back charm of island life, offering the perfect backdrop for your unforgettable getaway.brbrRelax in StylebrStep into a bright and airy living space designed for comfort and relaxation. Sink into the cozy sofa bed or unwind in one of the three beautifully appointed bedrooms, featuring one luxurious king bed and two inviting queen beds. Each room is a sanctuary of calm, complete with plush linens and thoughtful details to make you feel right at home. The bathrooms are equipped with everything you need, from a rejuvenating shower to a relaxing soak in the tub.brbrYour Island OasisbrPrepare meals in a fully equipped kitchen or head out to discover Key West’s world-class dining scene. When you’re not exploring, enjoy the peaceful outdoor spaces that make this property truly special. Sip your morning coffee on the porch as you listen to the tropical breeze rustling the palms, or gather with loved ones in the comfortable living area after a day of adventure.brbrPerfect Location, Endless AdventuresbrThis charming home is just minutes from Key West’s most iconic attractions. Stroll down lively Duval Street, soak up the sunset at Mallory Square, or discover hidden treasures in the local boutiques and galleries. Ready for some ocean fun Snorkeling, sailing, and pristine beaches are all within easy reach.brbrYour Hosts, Your GuidesbrWe’re here to ensure your stay is as seamless and enjoyable as possible. Whether it’s recommending the best seafood spot in town or sharing a hidden local gem, we’re just a message away.brbrBook Your Escape TodaybrWhether you’re planning a family getaway, a romantic retreat, or a trip with friends, this Key West home has everything you need for the perfect stay. Don’t wait—your island paradise is ready to welcome you!

Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

Key West, Florida, United States

3

Bed

3

Bath

8

Sleeps

$297.0

This listing is for a room within a hotel.brbr✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high definition 46-inch TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid parking lot – 1 space(s), available for $47.30 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $63.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). 2 total (up to 20 lbs per pet)brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.

Marker Key West Harbor, Pool & Garden View Room, 3 Outdoor Swimming Pools

Key West, Florida, United States

Bed

Bath

Sleeps

$274.11

Summary:brbrBeautiful 2- story townhouse with Dockage and PoolbrbrbrbrThe Space:brbrEscape to island paradise at this stunning 2-story vacation rental property in Key West. Nestled in a quiet community, this tropical oasis offers a water view and dock accessibility, allowing you to immerse yourself in the tranquil surrounding. Boasting 2 bedrooms, 2.5 bathrooms, and an open-plan living area, this property is perfect for families or groups of up to 4 guests. The chef-inspired kitchen is fully equipped with top-of-the-line appliances, ample counter space, and a perfect setting for culinary adventures. The living area is cozy and airy, providing the perfect ambiance for relaxation and socializing. Upstairs, the beautifully appointed bedrooms offer ample space for rest and privacy, and each has its own private bathroom with a luxurious walk-in shower. A dedicated office space is also included for those working remotely. Guests will have exclusive use of the property's private dock, invoking feelings of serenity and perfect for sipping morning coffee or enjoying sunset drinks. The community pool is also available for your enjoyment. With easy access to downtown, this tranquil retreat offers the best of both worlds. Don't miss the opportunity to escape to this island paradise and immerse yourself in the tranquility of Key West.

Serenity Retreat- 2/2 Townhouse, Dock & Pool

Key West, Florida, United States

Bed

3

Bath

Sleeps

$607.31

Welcome to WINDWARD SOUTH — Your Peaceful Retreat in the Heart of Old Town Key WestbrbrDiscover the perfect blend of comfort, charm, and tropical elegance at Windward South, a beautifully appointed 2-bedroom, 2.5-bathroom home ideally situated in the highly sought-after Old Town Key West neighborhood. This inviting getaway places you just steps from iconic sites such as world-famous Duval Street, the Ernest Hemingway Home and Museum, art galleries, historic architecture, top-rated restaurants, lively pubs, and the vibrant energy that defines Key West.brbrA Warm and Inviting First FloorbrStep inside to a bright and thoughtfully designed main level that immediately welcomes you with warmth and style. The spacious living room provides plush, comfortable seating—perfect for enjoying mornings with coffee, unwinding after island adventures, or spending time together in the evenings. Two sets of French doors fill the space with natural light, creating a relaxing tropical ambiance.brbrAdjacent to the living room is a formal dining room, ideal for shared meals, puzzles, games, or relaxing gatherings. The fully equipped kitchen offers everything you need for effortless vacation cooking and also opens to the backyard through another set of beautiful French doors.brA cozy guest suite is located on this level, offering convenience and comfort for guests who prefer to avoid stairs. A stylish powder room adds convenience for everyone staying at or visiting the home.brPrimary Suite: A Luxurious Second-Floor SanctuarybrbrAscend the spiral staircase to discover a truly exceptional feature of Windward South: the entire second floor is dedicated to the expansive primary suite.brThis serene retreat offers complete privacy and comfort, making it an ideal sanctuary for rest and rejuvenation. The suite features a luxurious king-size bed, generous natural light, and sophisticated island-inspired décor. The spacious layout provides room to relax, refresh, and recharge in total comfort. A beautifully appointed en-suite full bathroom completes the space, offering both convenience and a sense of indulgence. This private level of the home makes the primary suite the perfect haven for couples or anyone seeking quiet relaxation during their stay.brbrOutdoor Living at Its FinestbrStep outside to your own private tropical oasis. The backyard features a lagoon-style swimming pool, ideal for cooling off during warm Key West afternoons. Seasonal pool heating ensures that you can enjoy soothing swims year-round.brComfortable outdoor seating invites you to lounge under the sun, enjoy morning coffee in the breeze, or gather for evening cocktails and conversation. A gas grill makes outdoor cooking easy and enjoyable, whether you're preparing fresh seafood or grilling a casual meal with family and friends.brbrComfort, Convenience & Everything You Need! Parking is simple and stress-free with space for two vehicles in the driveway and in front of the home—an invaluable perk in the heart of Old Town.brThe home stays cool and refreshing thanks to efficient air conditioning and heating, ensuring comfort in every season. Whether you're getting ready for the day or winding down after exploring the island, every space feels soothing, cozy, and thoughtfully designed.brbrYour Key West Escape Starts HerebrWindward South is more than a vacation rental—it’s a place to unwind, reconnect, and create unforgettable memories. With its ideal location, comfortable living spaces, serene outdoor oasis, and beautifully designed suites—including the private second-floor primary retreat—this home offers everything you need for a brilliant getaway.brbrWhether you're visiting for romance, relaxation, adventure, or celebration, Windward South is ready to welcome you with the comfort and charm that make Key West unforgettable.brbrMake your vacation one for the books with a stay at Windward South.

WINDWARD SOUTH- Delightful 2-bedroom house with Pool in Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$777.66

Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic Designer Octagon House of Key West, makes a grand architectural statement. Often featured in notable publications with photos of its famous octagon shape front porches, the main structure of the house is in fact rectangular in shape with a multi-sided front. But it is the captivating five-sided front that distinguishes it from the many other remarkable centurion Victorian homes of Key West. Truly a home of fine distinction, it also has an eminent restoration history that began in 1976. Most recently in 2018, it received a sensational interior design makeover that brought it to current 5-Star Quality Resort Amenities standards.brbrA LITTLE BIT OF HISTORY:brbrOften referred to as `The Calvin Klein House,` in truth the iconic Designer Octagon House of Key West was an avant-garde preservation project accomplished by designer superstar Angelo Donghia during 1976 – 1978. Because of Donghia`s stellar status in the design world, this single renovation project was transformative for Key West during the 1970`s when creatives were beginning to turn neglected wooden centurion relics into elegant homes.brbrThe recipient of many prestigious awards during his lifetime and posthumously, Angelo Donghia was one of America`s most influential interior and furniture designers during the mid 1960`s through the mid 1980`s, with a celebrity client list with the likes of Ralph Lauren, Neil Simon, Diana Ross, Liza Minnelli, and elite projects such as the Metropolitan Opera House in New York and Omni International Hotels in Miami. His time spent in Miami in the 1970`s peaked his interest in Key West where he could easily escape from the bustle of the city for respite on an island accepting of artistic individuality and alternative lifestyles. `It`s a cross between Nantucket and Papeete, in Tahiti. It`s not a prissy resort, like Nantucket, but there`s some of Nantucket`s old elegance mixed with Key West raunchiness.`brbr`I`m a free spirit and a gambler,` is how Donghia described himself in interview, and when he got to Key West in the 1970`s he was taken with the hundreds of historic wooden houses and craftsmen who were beginning to restore them. When he found the unique octagon house on Eaton Street, it had been standing for over 90 years. Originally built in 1885 by Richard Peacon, the island`s principle grocer at the time, it had fallen into serious decay during economic downturns. As one of his cousins shared with me, Donghia was somewhat reluctant to do the project because of the neglected state of house. But dreamer that he was, in 1976 he purchased it for $45,000, and spent two years restoring it. He turned it into a spectacular show piece putting his indelible signature on the southernmost city.brbrHis approach to the eccentric octagon house had a casual point of view that highlighted renovation and preservation, and the décor reflected his own classic minimalist design style that earned him the nickname the `man with the gray flannel sofa.` Using tailor`s suiting fabrics, such as canvas, silk, linen and flannel, he `dressed` the rooms much like a tailor. An often-published photo of the living room displays this famous style that would become permanently embraced in the interior design world – white bleached wooden walls and floors, sofa and chairs in simple white canvas coverings, rattan furniture set on a natural fiber rug. Donghia`s renovation project was impeccable to the point where the house sold in 1981 to Calvin Klein for nearly $1 million – 15 times the original purchase and a record price at the time. Today we owe thanks to Angelo Donghia for saving this iconic home while raising the bar on historic home renovation in Key West. brbrbrBedding Summary:brbrbrFirst Floor (Bedroom One) - 1 King size bedbrbrSecond Floor – (Bedroom Two) – 1 Queen size bedbrbrSecond Floor - (Bedroom Three) Master Bedroom – 1 King size bedbrbrSecond Floor – (Bedroom Four) - 1 Queen size bedbrbrbrAmenities: Impeccable renovation with extraordinary designer decor. Expansive exotic back yard resort-style gardens, large swimming pool, outdoor back porch living room, mature tropical landscaping, expansive octagon verandahs, privacy fences. Fully equipped luxury kitchen, central a/c, 43-inch flat screen TV in living room, a 43-inch TV in the master bedroom, and 70-inch TV in the poolside pagoda. Full-size front-loading washer / dryer is set on the covered back porch, tropical style, hidden by a curtain. Linens and towels are provided. Catering can be arranged. Maid service can be scheduled.brbrActivities:Heart of Key West`s designated Historic Seaport District. Walk to all old town features, no need for a car. Close to Duval St., close to Mallory Square Sunset Celebration,and a few short streets from Historic Seaport (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife. Conveniently located to Fausto`s Food Palace for gourmet grocery shopping with excellent wine selection, sushi deli, and butcher. Close to shopping, art galleries, and a wide variety of outstanding restaurants and coffee shops. Close to the beach.brbrArea:This estate home is situated on famous Eaton Street, just one block from the docks of the Key West Historic Seaport. This tiny district is where the founding fathers and mothers built the first shipping docks and warehouses, restaurants and grand homes, including this one. Today these homes stand as one of the largest and most impressive collection of turn-of-the-century architecture in the U.S.A. Today this district includes famous waterfront restaurants and bars, retail stores, museums, fishing and sailing charters, a large variety of historic homes.brbrParking:There is a bricked driveway to the left of the house as you face the front. There is room to park more than one car if you park end to end. Once you`re here, park your vehicles and enjoy walking or biking everywhere—you`ll see more that way.brbrRestrictions:30-day minimum stay. Ideal for families and groups to unite but is not suitable for staging loud parties. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. Smoke free house.No pets please.brbrNotes:This property is ideal for professionals, corporate groups, and executives who have discerning tastes looking for a spacious and luxurious accommodation.

Designer Octagon House of Key West - w Private Pool - Blocks off Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$707.39

Enjoy all of Key West's exciting activities from the privacy and comfort of your own two-story, historic home in Old Town, Key West. brbrHidden behind lush tropical foliage, this 4 Bedroom (three suites on ground level), 2 Bathroom (+ 2 half baths) masterpiece awaits your arrival. This upscale home has many features such as open living and dining areas, eat-in kitchen, high ceilings, and wrap-around porches which overlook the completely private and heated swimming pool. brbrTake a short bike ride through the streets of Old Town and arrive at Duval Street's amazing restaurants, bars, shopping and art galleries.brbrNote: This house will be listed For Sale on October 1, 2025.

Eliza's Secret - Elegant Tropical Oasis with Private Pool & Guest House

Key West, Florida, United States

Bed

Bath

Sleeps

$1027.36

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale Bayfront Suites.brbrUpper Bayview South is the place to stay if you are looking for lodging where you and your guests can fully unwind in a coastal chic, home in Key West overlooking the water! The comfortable design and luxurious amenities are second to none in Key West and are sure to make your stay, a memorable one. brbrClose to the elevator, and upon entering this four-bedroom three-bathroom suite via our secure electronic lock system, one will first notice the tall ceilings and the high-end interior design the vacation home has to offer. This four-bedroom condo has been delicately crafted with high end furnishings, detailed moldings, and modern amenities. Plush couches with strategic accent pillows, a combination of single king and double-twin bedroom options, coupled with luxurious sheets along with a kitchen that’s fully equipped with stainless steel appliances, dishwasher, disposal and all the culinary tools needed to create the finest cuisine. brbrThis vacation home offers the most necessary amenity for a stay in the Florida Keys, a private covered porch. Like a local, take a seat and lean back on your private porch to enjoy your morning coffee or take an afternoon break to read your favorite book. In Upper Bayview South, guests can find their expansive views of Garrison Bight, from the property’s dock as well as the pool. brbrBeyond visual accommodations, Bayfront Suites also offers all the creature comforts one would need in their home away from home. Parking is provided for the vacation homes, and for the electric traveler, a car charging station is provided on the property. There is also complimentary wireless internet throughout the property, including the pool and tiki hut. Other amenities such as luxurious high thread count sheets, Virtual Concierges through Alexa, wireless thermostat and just in case you don’t get to the store in time, we provide your first morning’s coffee. The best part about these amenities, are that they align with Key West’s lifestyle to do good to Mother Earth. Bayfront Suites is a certified green building and LEED Certified, which means that a stay at Bayfront Suites is a step in reducing one’s carbon footprint. brbrOur unique pool design is perfect for any traveler including families. There is a dip area for shallow water enjoyment that kids love and designed for even the smallest of guests in mind. There are several ledges along the pool’s edge for relaxation. Situated on the water’s edge, enjoy the view while you soak. Plenty of lounge chairs and tables line the pool deck.brbrA rooftop deck was designed into the building of this fabulous small resort for guest’s enjoyment as well as to aid in providing a special area for which guests can have memorable events. We encourage guests to enjoy the panorama view from this rooftop deck overlooking Garrison Bight. brbrWe can accommodate one vessel up to 11' beam per reservation at no additional charge.brbrIn conclusion, Bayfront Suites and Marina is the place to have an enjoyable, comfortable and memorable retreat while in Key West and we hope to have you as our guest. brbrRATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

Waterfront 4-Bed 3-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED

Key West, Florida, United States

Bed

Bath

Sleeps

$491.99

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale Bayfront Suites.brbrSunset South (not waterfront) is the place to stay if you are looking for lodging where you and your guests can fully unwind in a coastal chic, home in Key West. The comfortable design and luxurious amenities are second to none in Key West and are sure to make your stay, a memorable one. brbrNear the elevator and upon entering this two-bedroom one-bathroom suite via our secure electronic lock system, one will first notice the high-end interior design the vacation home has to offer. This two-bedroom condo has been delicately crafted with high end furnishings, detailed moldings, and modern amenities. Plush couches with strategic accent pillows, a combination of single king and double-twin bedroom options, coupled with luxurious sheets along with a kitchen that’s fully equipped with stainless steel appliances, dishwasher, disposal and all the culinary tools needed to create the finest cuisine. brbrThis vacation home offers the most necessary amenity for a stay in the Florida Keys, a private and rather large, covered porch. Like a local, take a seat and lean back on your private porch to enjoy your morning coffee or take an afternoon break to read your favorite book. In Sunset South, guests can find their view of nearby neighborhood and natural foliage of the “Meadows”, a local term for the surrounding area. brbrBeyond visual accommodations, Bayfront Suites also offers all the creature comforts one would need in their home away from home. Parking is provided for the vacation homes, and for the electric traveler, a car charging station is provided on the property. There is also complimentary wireless internet throughout the property, including the pool and tiki hut. Other amenities such as luxurious high thread count sheets, Virtual Concierges through Alexa, wireless thermostat and just in case you don’t get to the store in time, we provide your first morning’s coffee. The best part about these amenities, are that they align with Key West’s lifestyle to do good to Mother Earth. Bayfront Suites is a certified green building and LEED Certified, which means that a stay at Bayfront Suites is a step in reducing one’s carbon footprint. brbrOur unique pool design is perfect for any traveler including families. There is a dip area for shallow water enjoyment that kids love and designed for even the smallest of guests in mind. There are several ledges along the pool’s edge for relaxation. Situated on the water’s edge, enjoy the view while you soak. Plenty of lounge chairs and tables line the pool deck.brbrA rooftop deck was designed into the building of this fabulous small resort for guest’s enjoyment as well as to aid in providing a special area for which guests can enjoy. We encourage guests to enjoy the panorama view from this rooftop deck overlooking Garrison Bight. brbrThis unit does not include boat dockage. brbrIn conclusion, Bayfront Suites and Marina is the place to have an enjoyable, comfortable and memorable retreat while in Key West and we hope to have you as our guest.brbrRATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

2 Bedroom 1 Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED

Key West, Florida, United States

Bed

Bath

Sleeps

$410.43

brWelcome to Coconut Cottage – Your Luxurious Key West Escape in Bahama VillagebrbrExperience the best of Old Town Key West at Coconut Cottage, a stunning new construction nestled in the vibrant Bahama Village neighborhood. This beautifully appointed 2-bedroom, 2-bathroom home offers an open-concept floor plan, upscale finishes, and an unbeatable location just blocks from iconic attractions, dining, and beaches.brbrThe Primary Suite:brEscape to the entire second floor dedicated to your comfort. The spacious suite features a king bed, a cozy sitting area with a sofa sleeper, a private lanai, and a dedicated workspace. The ensuite bathroom boasts a luxurious soaker tub, walk-in shower, dual vanity, and a large walk-in closet. Zoned central AC keeps this sanctuary perfectly comfortable year-round.brbrGuest Bedroom & Baths:brThe first floor offers a charming guest bedroom with a queen bed and easy access to a stylish hallway bathroom with a custom vanity and beautiful shower.brbrLiving & Entertaining Spaces:brThe open living room and kitchen flow seamlessly to the outdoor entertainment area and pool deck. The kitchen shines with stainless steel appliances, quartz countertops, and a breakfast bar with seating for three. Relax with your favorite shows on the 65 smart TV or dine indoors or outdoors for up to four guests.brbrOutdoor Oasis:brStep through the fully retractable sliding doors to your private tropical retreat. Lounge by the heated (available seasonally) 7’ x 12’ plunge pool with a soothing waterfall feature, surrounded by lush foliage. Enjoy the pool deck with loungers, outdoor dining, and seating areas — perfect for soaking up the Key West sunshine or stargazing at night.brbrExtras You’ll Love:brbrOff-street parking for up to 2 cars — a rare find in Old Town!brbrJust 2 blocks from the lively 1000 block of Duval StreetbrbrMinutes from Southernmost Point, Fort Zachary Taylor Beach, and Truman Annex Waterfront ParkbrbrSecurity cameras on front and side for your peace of mindbrbrPlease Note:brThis is a seasonal rental available for stays of 28 days or longer. Sorry, no pets allowed.brbrReady to book your slice of paradise Coconut Cottage is the perfect blend of comfort, style, and location for your next Key West getaway!

COCONUT COTTAGE- Island Vibes & Cozy Stays W/ Pool & Parking - OLD TOWN KEY WEST

Key West, Florida, United States

Bed

Bath

Sleeps

$1175.91

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale Bayfront Suites.brbrUpper Bayview North is the place to stay if you are looking for lodging where you and your guests can fully unwind in a coastal chic, home in Key West overlooking the water! The comfortable design and luxurious amenities are second to none in Key West and are sure to make your stay, a memorable one. brbrUpon entering this four-bedroom suite four-bathroom via our secure electronic lock system, one will first notice the high-end interior design the vacation home has to offer. This four-bedroom condo has been delicately crafted with high end furnishings, detailed moldings, and modern amenities. Plush couches with strategic accent pillows, a combination of single king and double-twin bedroom options, coupled with luxurious sheets along with a kitchen that’s fully equipped with stainless steel appliances, dishwasher, disposal and all the culinary tools needed to create the finest cuisine. brbrThis vacation home offers the most necessary amenity for a stay in the Florida Keys, a private covered porch. Like a local, take a seat and lean back on your private porch to enjoy your morning coffee or take an afternoon break to read your favorite book. In Upper Bayview North, guests can find their expansive views of Garrison Bight and the property’s private dock.brbrBeyond visual accommodations, Bayfront Suites also offers all the creature comforts one would need in their home away from home. Parking is provided for the vacation homes, and for the electric traveler, a car charging station is provided on the property. There is also complimentary wireless internet throughout the property, including the pool and tiki hut. Other amenities such as luxurious high thread count sheets, Virtual Concierges through Alexa, wireless thermostat and just in case you don’t get to the store in time, we provide your first morning’s coffee. The best part about these amenities, are that they align with Key West’s lifestyle to do good to Mother Earth. Bayfront Suites is a certified green building and LEED Certified, which means that a stay at Bayfront Suites is a step in reducing one’s carbon footprint. brbrOur unique pool design is perfect for any traveler including families. There is a dip area for shallow water enjoyment that kids love and designed for even the smallest of guests in mind. There are several ledges along the pool’s edge for relaxation. Situated on the water’s edge, enjoy the view while you soak. Plenty of lounge chairs and tables line the pool deck. brbrA rooftop deck was designed into the building of this fabulous small resort for guest’s enjoyment as well as to aid in providing a special area for which guests can have memorable events. We encourage guests to enjoy the panorama view from this rooftop deck overlooking Garrison Bight. brbrWe can accommodate one vessel up to 11' beam per reservation at no additional charge.brbrIn conclusion, Bayfront Suites and Marina is the place to have an enjoyable, comfortable and memorable retreat while in Key West and we hope to have you as our guest.

Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED

Key West, Florida, United States

Bed

Bath

Sleeps

$1323.92

THE PROPERTY: Enjoy your stay in the tropics at the highly touted Queen Conch complex, which includes 3 separate rentable units: Horse Conch, Rooster Conch, and Sea Conch. You can rent each unit individually, but by renting “Queen Conch” you will enjoy all 3 units and ultimate privacy during your Key West vacation.brbrHorse Conch is located on the second floor, overlooks the pool, and shares a balcony with Rooster Conch. The unit includes one king bedroom (no TV in the bedroom), closet and dresser storage, as well as an ensuite bath with pedestal sink and walk in shower. The open concept living area includes plenty of seating, a flat screen TV and an updated kitchen with stainless steel appliances and table seating for four. brRooster Conch is also located on the second floor, overlooks the pool, and shares a balcony with Horse Conch. The unit includes one king bedroom with a TV, closet, and dresser storage, as well as an ensuite bath with pedestal sink and walk in shower. The open concept living area includes plenty of seating, a flat screen TV and an updated kitchen with stainless steel appliances and table seating for four.br brSea Conch is the larger first-floor unit where you can enjoy people watching on the charming front porch. The home includes one king and one queen bedroom with ensuite baths, pedestal sinks and large walk-in showers. The open concept living area is spacious and includes a flat screen TV, plenty of seating and easy access to the pool area. The kitchen with stainless steel appliances and an abundance of cabinets is fully equipped for the chef in your family. Enjoy meals al fresco via a wall of French doors or in the home’s spacious dining area with table seating for eight. Sea Conch provides you with a wonderful place to entertain during your stay in paradise. brbrAdditional details may be found in each of the rental’s individual property descriptions, however, all units that make up Queen Conch are flooded with natural light and contain cheerful Key West Décor. Enjoyable open concept living is provided in each unit complete with pops of color, flat screen TVs, hardwood floors, and plenty of seating. White kitchens with stainless steel appliances make meal prep a breeze. French doors open onto the covered balcony or decks, allowing you to enjoy indoor/outdoor living. A gas grill is provided for cooking up your catch of the day or burgers for the kiddos. The outdoor pool area is secluded and lushly landscaped for a truly tropical experience. Don’t delay, come out of your ‘shell’, and rent the stunning Queen Conch today! brbrBED CONFIGURATION: By renting Queen Conch, you will enjoy a combined total of four bedrooms, four baths and three pull out sofas that provide sleeping spaces for 14. Sea Conch has one king and one queen bedroom. Rooster Conch and Horse Conch each have one king bedroom. brbrOUTDOOR AMENITIES: The complex boasts lush tropical landscaping and palm trees. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The pool area is adorned with a dining table, umbrellas, and loungers. A gas grill allows you to cook your catch of the day or a great burger! A washer/dryer is in a shed on the left side of the home near the pool.brbrPARKING: Queen Conch offers 1 designated off street parking spot for 1 vehicle. brbrLOCATION: Many Key West attractions are located nearby, as well as numerous restaurants, shops, and galleries. The neighborhood boasts historic conch-style homes. Enjoy café con leche down the street at Cuban Coffee Queen or lunch at 5 Brothers Sandwich Shop. Walk to dinner at Blue Heaven, Caroline’s Cafe, or Sloppy Joe's. You will have many choices located within a 10-minute walk!brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that allow pets.)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***

~QUEEN CONCH ~ Amazing location with pool and room for family and friends!

Key West, Florida, United States

Bed

Bath

Sleeps

$718.37

THE PROPERTY: Enjoy your stay in the tropics at Sea Conch, part of the highly touted Queen Conch complex, which includes 3 separate rentable units: Sea Conch, Horse Conch, and Rooster Conch. You can rent each unit separately or rent “Queen Conch” to enjoy all 3 units and ultimate privacy during your Key West vacation.brbrSea Conch can be accessed via the home’s charming front porch where you can enjoy morning coffee or people watching. Sea Conch also includes your own covered back deck that overlooks the shared pool and courtyard area. The pool is shared with the two second floor units in this home - Horse Conch and Rooster Conch. brbrUpon entering your vacation home, you will be delighted by the natural light, hardwood floors, cheerful Key West décor, and the work of local artists. The open concept living room area is large and includes pops of color, a flat screen TV, and plenty of seating for you and your guests. A white kitchen with subway tile, stainless steel appliances and an abundance of cabinets is fully equipped and offers all the amenities of home. A drum chandelier and a large dining table with seating for eight complement the area. Enjoy indoor/outdoor living via the double French doors that open onto your covered deck and provide direct access to the pool area.brbrEach bedroom has an ensuite bath, bedside tables with lamps, ceiling fan, closet, and dresser storage. Each ensuite bath has a large pedestal sink and tiled walk-in shower. Don’t delay, come out of your ‘shell’, and rent the stunning Sea Conch today! brbrBED CONFIGURATION: One bedroom contains a king size bed and TV; the second bedroom has a queen size bed and TV. There is a queen sleeper sofa in the living room. brbrOUTDOOR AMENITIES: The complex boasts lush tropical landscaping and palm trees. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The pool area is adorned with a dining table, umbrellas, and loungers. A shared gas grill allows you to cook your catch of the day! A shared washer/dryer is in a shed on the left side of the home near the pool.brbrPARKING: Sea Conch offers 1 designated off street parking spot for 1 vehicle. brbrLOCATION: Many Key West attractions are located nearby, as well as numerous restaurants, shops, and galleries. The neighborhood boasts historic homes, shotgun, and conch-style homes. Enjoy café con leche down the street at Cuban Coffee Queen or combine it with lunch at 5 Brothers Sandwich Shop. Walk to dinner or drinks at Blue Heaven, Caroline’s Cafe, Fogarty's, Irish Kevin’s, or Sloppy Joe's. You will have many choices located within a 10-minute walk!brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that allow pets.)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***

Apartment

SEA CONCH~ Amazing location with shared pool, deck, and parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$372.98

THE PROPERTY: Enjoy your stay in the tropics at Horse Conch, part of the highly touted Queen Conch complex, which includes 3 separate rentable units: Horse Conch, Rooster Conch, and Sea Conch. You can rent each unit separately or rent “Queen Conch” to enjoy all 3 units and ultimate privacy during your Key West vacation.brbrHorse Conch can be accessed via the stairway on the right side of the home. The stairway leads up to the entrances to both the Horse Conch and Rooster Conch units. Horse Conch includes a shared, covered balcony that overlooks the sparkling pool and courtyard area. The pool is shared with the Rooster and Sea Conch units.brbrUpon entering your vacation home, you will be delighted by the natural light, hardwood floors, cheerful Key West décor, and the work of local artists. The open concept living room includes pops of color, a flat screen TV, and plenty of seating for you and your guests. A white kitchen with subway tile, stainless steel appliances and an abundance of cabinets is fully equipped and offers all the amenities of home. Pendant lighting and a dining table with seating for four complement the area. brbrStep up into the king bedroom with ensuite bath, bedside tables with lamps, closet and dresser storage. A large pedestal sink and tiled walk-in shower are all yours. A second split-unit AC system and ceiling fan keep your sleeping area cool and comfortable. Whether you vacation solo or with a partner, come out of your ‘shell’ and rent the handsome Horse Conch today! brbrBED CONFIGURATION: The king bedroom has an ensuite bath. For those that need their rest, please know that there is no TV in the bedroom. There is a queen sleeper sofa in the living room.brbrOUTDOOR AMENITIES: The complex boasts lush tropical landscaping and palm trees. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The pool area is adorned with a dining table, umbrellas, and loungers. A gas grill allows you to cook your catch of the day! A shared washer/dryer is in a shed on the left side of the home near the pool.brbrPARKING: Please be aware that Horse Conch offers street parking only. Free but limited parking may be available in the neighborhood. brbrLOCATION: Many Key West attractions are located nearby, as well as numerous restaurants, shops, and galleries. The neighborhood boasts historic homes, shotgun, and conch-style homes. Enjoy café con leche down the street at Cuban Coffee Queen or combine it with lunch at 5 Brothers Sandwich Shop. Walk to dinner or drinks at Blue Heaven, Caroline’s Cafe, Fogarty's, Irish Kevin’s, or Sloppy Joe's. You will have many choices located within a 10-minute walk!brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that allow pets.)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***

Apartment

~HORSE CONCH~ Amazing location with shared pool and covered balcony!

Key West, Florida, United States

Bed

Bath

Sleeps

$290.99

Meticulously restored and maintained 2 bedroom (+ den/3rd bedroom with sleep sofa), 3 full bath home in the heart of Old Town. Relax in an outdoor tropical oasis with dining under the pergola, heated pool with waterfall, outdoor shower, Azek decking, fire pit, gourmet outdoor kitchen, a large front porch with swing, and beautiful landscaping with lighting. Many custom touches including chef's kitchen with granite, wine refrigerator, original Miami Dade pine floors, coffer ceilings, and interior washer/dryer. The extra large lot has a private driveway providing highly desirable off street parking. Master bedroom with queen bed has its own bath with spa shower and separate claw foot tub. Guest bedroom with queen bed has its own bath with spa shower. Den with comfortable full size pull out sofa bed opening to pool area has its own bath with beautiful stone shower. WiFi, AC/heat, ceiling fans. Perfect place to relax and escape. Easy walking distance to the beautiful, historic Basilica of St. Mary Star of the Sea , White Street Art District, Higg's Beach, the White Street Pier, Duval Street, and wonderful restaurants, including Salute on the Beach, Seven Fish, El Siboney Cuban Restaurant, Louie's Backyard and many more. Walk, bike or drive to everything Key West has to offer. Wonderful neighbors to make you feel welcome and at home. Well-behaved small dog considered.

Welcome to Parrot Dice! An Old Town tropical oasis with a private heated pool.

Key West, Florida, United States

Bed

Bath

Sleeps

$532.13

This listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

Pet-Friendly Coastal Retreat in Key West with Private Beach Access

Key West, Florida, United States

Bed

Bath