Home Vacation Rentals By Owner In Key West, FL

Showing 1180 Of 2059 Vacation Rentals
Slider Thumb
Exceptional(9)

$727.86

/ Nightly
Condo

NEW LISTING! Oceanfront luxury awaits!

Key West, Florida, United States

Enjoy endless views just feet away from the tranquil waters of the Atlantic Ocean. Condo 206 is a serene waterfront oasis located in the Key West Beach Club, an upscale gated community with two oceanfront pools, pavilion area, workout room and tennis court. It is within walking or biking distance to restaurants, public beaches, shops, bars and iconic Duval Street. This condo prides itself for being one of the very few on the island that sits directly on the coastline.brbrThe expansive living room is brightly decorated exuding light from floor to ceiling. The breathtaking view can be seen as soon as you enter this spacious 3-bedroom coastal retreat, with comfortable seating for those spontaneous movie nights. The open kitchen is fully equipped to make that perfect home cooked meal. Relax on the outdoor furniture or dine oceanside on your large, private balcony while soaking in the panoramic ocean views. The balcony is the perfect place to enjoy an evening cocktail or freshly brewed morning cup of coffee.brbrBedroomsbrMain Bedroom: King bed, large built-in desk, flat screen TV, direct access to the balcony, ensuite bathroom with spa-like shower.brbrFront Left Bedroom: 2 Twin beds OR One King Bed, large built-in desk, flat screen TV, shared hall bathroom with walk-in shower.brbrFront Right Room: Queen sized bed, flat screen TV and shared hall bathroom with walk-in shower.brbrUnit Features:brCentral A/C, Wi-Fi, washer/dryer, security entry, open parking and elevator access.brbrCommunity Amenities: Resort amenities include two ocean side pools (heated), tennis court, outside cooking facilities, fitness center and sauna. Since the shoreline is natural, beach access is best at the public beaches on either side of the community. Smather’s Beach is around the corner to the left and Higgs Beach is just past White Street Pier to the right. There are plenty chaise lounges around the pool area as well as a pavilion to enjoy during those sunny island afternoons.brbrAdditional things to know:brThe Key West Beach Club Condo Association requires additional registration, which includes providing copies of photo IDs for everyone over the age of 17, in advance of your arrival. Details will be provided along with your RKWV rental agreement.brbr*Disclaimer: Due to the property's oceanfront location, please be aware that Key West experiences seasonal occurrences of fermenting turtle grass along the south shore of the island brought on by our southern winds in the late spring and summer. This is a natural phenomenon that is outside of our control.brbrInterim housekeeping provided upon request brThis property will accommodate up to 6 adults brSorry, pets are not allowed.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb

$344.56

/ Nightly
Private Vacation Home

GOOD VIBES ~ 2 Cottages w/ 4 BR/3 Ba, Outdoor Oasis and Parking!

Key West, Florida, United States

MEMORIES TO LAST A LIFETIME…brThis unique set of 2 charming, Conch style homes provide the perfect compound setting for your fun-loving family gathering in the Florida Keys. Cheerful living spaces among a desirably lush outdoor space entails the quintessential island spirit that the iconic town of Key West is known and loved for. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbr(cottage on the right)brA lovely front porch greets you inside with cheery surroundings showcasing a fully equipped and updated kitchen with bar seating for 4 which graciously opens up to a living room equipped with comfortable furnishings and a flat screen TV. Find a spacious queen bedroom with a TV and en suite bathroom with a shower/tub combination. Perched above this room is a loft with a queen bed. A roomy 1-bedroom backyard cottage comes with a flat screen TV, full kitchen, bathroom with a shower/tub combination and a queen bed. Enjoy a queen sofa sleeper in the cottage for additional visiting guests.brbr(cottage on the left) brShowcasing a nautical lifestyle with modern amenities, this retreat is outfitted with an updated and fully equipped kitchen with bar seating for 3. The adjacent living area is complete with cozy furnishings and a flat screen TV for movie nights. Find a king bedroom with a flat screen TV located at the front of the home which can also be accessed from the lovely front porch. Steps away is another guestroom outfitted with a queen bed and a flat screen TV. A full bathroom with a glass shower resides just outside both guestrooms.brbrOUTDOOR LIVING…brOpen the bamboo gate connecting both outdoor areas to create a spacious gathering area for all your loved ones to come together in this outdoor oasis. Plush outdoor furnishings among vibrant surrounds create an immediate sense of R & R as you grill up your fresh catch of the day and rinse off in the outdoor shower. Imagine hopping into town to all the island favorite bars, galleries and restaurants and having a short distance home to your peaceful abode. brbrPARKING...brEnjoy the convenience of 2 parking spots!brbrPETS...brPets up to 30 pounds are considered and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrLET YOUR KEY WEST STORY UNFOLD…
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(15)

$207.35

/ Nightly
Private Vacation Home

POSITIVE VIBES ~ Charming 2 BR, 1 Ba Cottage in Peaceful Area w/ Parking!

Key West, Florida, United States

LOST ON ISLAND TIME…brTreasure your time together within this charming Key West cottage tucked away on this peaceful and vibrant lane in the iconic Old Town district. As you step inside a lifetime of memories are created as your loved ones come together for a unique and blissful getaway. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brShowcasing a nautical lifestyle with modern amenities, this retreat allows you to truly live in the present. Enjoy a front porch boasting island views at every corner as you wave hello to friendly neighbors passing by. Within the home you will find an updated and fully equipped kitchen with stainless steel appliances and granite counters. Enjoy bar seating for 3 or take your treats outside and dine al fresco in the welcoming breeze. The adjacent living area is complete with cozy furnishings and a flat screen TV for movie nights. brbrSLEEPING ARRANGEMENTS…brFind a king bedroom with a flat screen TV located at the front of the home which can also be accessed from the front porch. Steps away is another guestroom outfitted with a queen bed and a flat screen TV. A full bathroom with a glass shower resides just outside both guestrooms. brbrOUTDOOR LIVING…brIndulge in island time within this lush and vibrant outdoor setting beckoning you in for more. Unwind with a good book on the plush outdoor furniture and stroll around by foot in this peaceful neighborhood. brbrPARKING...brThis home allows parking for one vehicle.brbrPETS...brPets up to 30 pounds are considered and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). brbrTIME TO LIVE IN THE PRESENT…
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(8)

$211.84

/ Nightly
Private Vacation Home

GOOD FEELIN ~ Charming 2 BR/2 Ba Home Conveniently Located w/ Parking!

Key West, Florida, United States

SPOIL YOURSELF…brCome unwind in this tropical retreat allowing for your delightful Key West story to unfold. Sounds of swaying palm trees beneath sunny skies will draw you into this picturesque dream you’ve been craving for within this quaint Old Town sanctuary. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENTITIES…brStep onto a lovely front porch pulling you out of reality and into island time washing all your worries away. Inside you will be greeted with cheery surroundings and cool wood flooring within this cozy space bringing the everyone together. An updated kitchen featuring stainless steel appliances and granite counters graciously opens up to a living room equipped with comfortable furnishings and a flat screen TV. Enjoy bar seating for 4 or take your treats outside to dine together welcomed by a sweet tropical breeze. brbrSLEEPING ARRANGEMENTS…brFind a spacious queen bedroom equipped with a flat screen TV and a bathroom with a shower/tub combination that also opens up to the hallway for convenience. Perched above this room is a loft with a queen bed. Beyond the outdoor living space lies a roomy 1-bedroom cottage with a flat screen TV, full kitchen, en suite bathroom with a shower/tub combination and a queen bed. Enjoy a queen sofa sleeper in the cottage for additional visiting guests. brbrOUTOOR LIVING…brCome unwind in this desirable outdoor space offering a wonderful place to lounge and enjoy the simple treasures of island life. Grill up your fresh catch of the day and sip on your cocktail beneath the stars. Enjoy an outdoor shower to wash the day away. This home is just a short bike ride to all the beloved Key West attractions. brbrPARKING...brThis home allows parking for one vehicle.brbrPETS...brPets are considered up to 30 pounds and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrCOME AND STAY A WHILE…
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(1)

$161.41

/ Nightly
Private Vacation Home

Fish Camp | Old Florida canalfront getaway

Key West, Florida, United States

Summary:brbrOld Florida canalfront getaway close to Key WestbrbrbrbrThe Space:brbrEscape to this Old Florida-style cottage offering a quintessential retreat for fishing enthusiasts and nature lovers alike. Located just a short distance from the vibrant energy of Key West, this charming monthly rental promises tranquility and adventure in equal measure.brbrbrbrBoasting 100 feet of concrete dockage, complete with electric and water hookups, as well as a convenient fish cleaning station, this cottage is a haven for anglers seeking the thrill of the catch. An added bonus is the presence of a 600-pound ice machine and bait and fish freezers, ensuring that every fishing expedition is well-equipped and memorable. It's worth noting that this rental is best suited for shallow draft boats, as the canal entrance has approximately 2 feet of depth.brbrbrbrStep inside to discover a cozy interior with rustic charm. The quaint kitchen is equipped with the essentials but no dishwasher. This cottage features two bedrooms, each furnished with a comfortable queen bed, providing a peaceful sanctuary for rest and relaxation after a day of exploring the waters. Window air conditioners ensure a comfortable indoor climate, while ceiling fans circulate the refreshing sea air.brbrbrbrWhether you spend your days casting lines off the dock, exploring nearby Key West attractions, or simply unwinding in the peace and quiet of Baypoint, this monthly vacation rental offers a perfect blend of serenity and adventure for your coastal getaway. Experience the laid-back charm of the Florida Keys from this idyllic waterfront retreat.brbrbrbrThe primary guest must sign a rental agreement. This is a 28-day minimum rental per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 4 people. All guests need to be registered with the property manager. No smoking. Up to 2 pets permitted with manager approval and $250 nonrefundable per-pet fee. There's a cap on electric ($250) and water/sewer ($150) .
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(206)

$481.02

/ Nightly
Private Vacation Home

Casa Caribe Beautiful tropical 2 bedroom sleeps 6

Key West, Florida, United States

Tropical 2 bedroom, 2.5 bathroom, 2 level Key West townhome to be your home away from home! No detail has been overlooked in this comfortably decorated vacation rental. Located in one of the islands newest gated community’s, Coral Hammock, you are close to all that Key West has to offer. If you’re looking to kick back and relax in a homey atmosphere, Casa Caribe is the place for you! brbrOn the first floor, the kitchen is vibrant with fresh white cabinetry. Full kitchen appliances allow for either complete at home dining or even for quick and easy meals. Ceramic tiles cover the first level, giving you a classic Key West look. There is also a powder room on the main floor for convenience. brbrInterior walls throughout the house have been painted with soft and fun, tropical colors which ties in a true island ambiance. The deck extending from the living area is complete with comfortable wicker style furniture, which serves as the perfect spot to relax and enjoy the deck’s amazing view of the pool and lush landscaping of the complex. brbrThe second floor leads to the two main, airy bed and bathrooms. There are dual masters on either side of the home, separated by an in house laundry with a new washer and dryer, keeping you fresh and lightly packed while on vacation. Both masters have spacious bathrooms, which are tastefully decorated with bright accessories, mirrors and lush textiles. The first master bedroom is a retreat for your soul with a king size bed. Two large windows on adjacent walls along with a full size glass door leading to the second floor deck (also overlooking the pool) illuminate the room with Key West’s happy, natural sunlight. The second bedroom, queen size bed clothed with 600 thread count linens. Two large windows above the bed frames allow for a bright and refreshing space.brThe carpets have been replaced with wood flooring in bedrooms, hall and stairs.brThis home is fully stocked and ready to go for your convenience. Pack a few swimsuits and leave your worries at home, we have you covered with all of the amenities you need for your home away from home.brbrLiving Room:brTV with free cable and WiFi Internet accessbrDark blue sleeper sofa and love seat, perfect for lounging with your favorite bookbrWarm, tropical décor setting the mood for island lifebrbrKitchen:brBright and fresh cabinets and counter topsbrFull kitchen appliances including stove, microwave, refrigerator, and dishwasherbrFully stocked with flat ware, dinner ware, cups, mugs, utensils, pots and pansbrCoffee Pot brBlender (perfect for morning smoothies and evening margaritas!) brBasic necessities for your meal prep including spices, condiments, etcbrbrDining Room:br6-chair dining room tablebr2 stools set at the breakfast bar off the kitchenbrbrMaster Bedroom:brKing size bedbrPillow top mattressbr600 Thread count linensbrNight standsbrClosetbrPrivate bath stocked with fresh linensbrTV with cablebrbrSecond bedroom:brQueen bedbr600 Thread count linensbrNight standbrClosetbrPrivate bath stocked with fresh linensbrTV with cablebrbr1st Floor Porch:brTropical outdoor patio setbrbrGarage/ground level:brCovered parking for 1 carbrStreet parking for additional vehiclesbrBBQ area just steps away from the poolbrbrbrCommunity Features:brLarge heated pool with lounge chairsbrClubroom available for large parties (with a small fee)brFully equipped fitness centerbrLush tropical landscaped grounds perfect for evening walksbrGated community brbrSurrounding amenities:brCasa Coral is just north of the island, about 4 miles from famous Duval Street. This puts you just far enough away from the infamous Key West nightlife that you can enjoy an evening out, and come home to your relaxing and quite tropical get away. brbrFor your daytime adventures, the community sits directly across the street from the islands only public golf course, is on the next block up from a public boat ramp, is lined by a bike path to take you around the whole island, and is next to some of the best local dining where you can enjoy fresh seafood, Cuban cuisine and more!brbrJump on a bike and ride along South Roosevelt Blvd to enjoy the spectacular views along Smathers Beach, or take your car for a ride along North Roosevelt where all the islands shopping is just minutes away. Close to several water activities including jet ski rentals, catamaran adventures, glass bottom boat tours, historic old town Key West tours, and so much more.brbrCasa Caribe is owned and rented by Key West natives, who grew up and have now raised their family on the island. They are the perfect couple to give you advise on the best of the local spots for dining, dancing, shopping, sight seeing and activities! This townhome retreat is truly your ideal vacation package, and we can’t wait to welcome you!br
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(21)

$324.83

/ Nightly
Private Vacation Home

~ VILLA AZUL ~ Enjoy this historic home with pool house and parking.

Key West, Florida, United States

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 in the heart of Old Town Key West on a teeny tiny quiet lane, this two-story home with a first-floor bedroom is ideal for the entire family. Elders will enjoy the convenience of single-story living in the four-poster queen bedroom with hall bath, armoire storage and a window seat overlooking Curry Lane. You can enjoy the second floor’s primary king bedroom with large closet, as well as the spacious ensuite bath with dual sinks, walk in shower and claw foot tub. Your guests or young adults may enjoy the privacy of their own pool house with an ensuite half bath and delightful outdoor shower. brbrThe first floor is also where you will find the spacious family room adorned with hardwood floors and rattan, Bahamian, and British Colonial style furniture. An updated kitchen with granite countertops and stainless-steel appliances includes everything you need to prepare meals or snacks. Adjacent to the kitchen is the dining area with seating for six. Two large sets of French doors in the family room provide access to the outdoors and pool area. Here you will find a seasonally heated pool, lounge chairs, a gas grill, and an outdoor dining table under a covered loggia. Access to the outdoor shower and half bath in the pool house is also found here. Surrounded by palm trees, a large mango tree, and lush landscaping, you will find peace and serenity in this spacious island home in paradise. brbrBED CONFIGURATION: The first floor has a queen bedroom with hall bath. The second floor has a king primary ensuite with additional daybed. The pool house has a queen bed and an ensuite half bath with attached outdoor shower. brbrOUTDOOR AMENITIES: Lush landscaping surrounds the amazing pool. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Dine outdoors under the covered loggia with table, chairs, and a large mango tree! A gas grill and lounge chairs are also provided for your enjoyment. brbrPARKING: There is one parking space for a small car which is a real perk in Key West. Additional parking may be found on neighboring side streets. Please note this home is on a small lane. brbrLOCATION: Old Town, North of Truman Avenue and near The Meadows neighborhood. Numerous tourist attractions are located here as well as several restaurants and shops. The area boasts historic and conch style homes and is 4 blocks from the Historic Seaport District and Art Gallery District on White 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***Please note that the cleaning fee includes a full mid-stay clean***brbr***Guests must be 25 years of age or older unless accompanied by an adult. brbr***Managed by Historic Key West Vacation Rentals***
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(65)

$388.75

/ Nightly
Apartment

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

Key West, Florida, United States

THE PROPERTY: Enjoy your stay in the tropics at Rooster Conch, part of the highly touted Queen Conch complex, which includes 3 separate rentable units: Rooster Conch, Horse 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.brbrRooster Conch can be accessed via the stairway on the right side of the home. The stairway leads up to the entrances to both the Rooster Conch and Horse Conch units. Rooster Conch includes a shared, covered balcony that overlooks the sparkling pool and courtyard area. The pool is shared with the Horse 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, TV, 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 ravishing Rooster Conch today!br brBED CONFIGURATION: The king bedroom has an ensuite bath. 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 Rooster Conch offers street parking only. Free but limited street 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***
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb

$840.38

/ Nightly
Condo

Three Duval Street Suites w free parking and pool

Key West, Florida, United States

Summary:brCuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen with bathroom. Overlooking Duval street in historic Old Town, Key West. Paradise Suite is a one bedroom (king) with a pull down bed (queen murphy bed) and kitchen with a full bathroom. In historic Old Town, Key West. Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (king) and kitchen. Overlooking Duval street in historic Old Town, Key West. Two free parking spaces are available and the heated and cooled pool is privately located behind the building . Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.brbrThe Space:brCuban Club Suite is situated in the corner of the penthouse and is the perfect way to experience 180 degree views overlooking Duval Street in an open-concept room. Far from an outdated or run-of-the-mill hotel room, this suite offers mid century style furnishings with bright teal, orange and yellow Cuban colors and textures. It is styled to take guests back to a time when Cuban culture dominated Southern Florida- when Cuban music filled the streets, hand rolled Cuban cigars were everywhere, and Mojitos were the most popular drink on the menu. Besides style, Cuban Club Suite offers guests 1 (one) Queen bed and 1 (one) Queen pull down bed. There is room for dining and mixing drinks next to the kitchen while relaxing after a day at the pool or beach. The paradise suite is individually designed and decorated with 400 luxurious square feet each to relax and enjoy. Vibrant Caribbean colors and décor with relaxed and enjoyable furnishings are the setting to this suite. One of the more colorful suites Duval St. Suites has to offer, the Paradise Suite captures classic Key West: colorful people, bright sunny days, and an endless amount of fun. It is also one of the bigger suites in the penthouse, offering 1 (one) King sized bed and 1 (one) Queen murphy bed. There is a fully equipped kitchen, dining and living room area and private bathroom. The bedroom en-suite can be closed for privacy with the bi-fold louver doors. Vibrant Caribbean colors and décor with relaxed and enjoyable furnishings are the setting of the Mile Zero Suite. This tropical blue suite was nicknamed Mile Zero due to the inviting blue waters you find at the end of US Highway 1. In fact, Duval Street Suites, sits only a short walk away from the southernmost tip of the continental United States. This suite still has all the mainland amenities, including 1 (one) Queen bed and 1 (one) Queen sofa sleeper. There is room for mixing drinks and dining off of the kitchen and a comfortable couch for you and your guests. In addition, this suite boasts 90 degree views overlooking Duval Street. The Suite is complete with all standard hotel accommodations, including a full private bathroom, cable television, and internet access, plus access to a washer/dryer. The pool area has a BBQ grill, lounge chairs, dining and picnic area with outdoor bar and TV area. The three suites are complete with all standard hotel accommodations, including three full private bathrooms, cable televisions, and internet access, plus access to a washer/dryer. The pool area has a BBQ grill, lounge chairs, dining and picnic area with outdoor bar and TV. Two of four parking spaces in the rear of the property are free of charge for guests. Traveling with other friends or family members, Duval Street Suites offers a truly unique layout with six individual suites. The property then can be rented as a whole Penthouse for one large group. We are a locally owned and operated vacation rental.brbrGuest Access:brDuval Street Suites utilizes key-less entry and self check-in. You will have access to free Wi-fi, Hulu streaming service, a private pool reserved for guest staying at the property located directly behind the building. Duval Street is located in the front of the building.brbrThe Neighborhood:brWithin walking distance to several highly rated restaurants, shops, and entertainment venues to meet the needs of all groups and ages. A short 5-10 minute walk will get you to: The Key West Butterfly and Nature Conservatory, Key West Lighthouse, The Hemingway Home and Museum, and Southernmost Point of the Continental USA. Mallory Square, is a 15 minute walk from the property. The street performers, food carts and sunset are sure to leave you with that warm and fuzzy feeling. Duval St. Suites is surrounded by several restaurants within 5-10 minutes of walking such as: Moon Dog Café, DJ's Clam Shack (featured on Food Network's, Diner's, Drive-in's and Dives), Better Than Sex- A Dessert Restaurant, Blue Heaven, Sloppy Joes, Hard Rock Café and many more hidden gems along the way. Close to everything and yet its still quiet and private at the calmer end of Duval Street, but mere minutes away from all the action. Duval Street Suites is close to perfect!brbrGetting Around:brKey West is a small city on a tiny Island. Streets are narrow and often congested with cars, motorcycles, people and chickens! To save money on gas, promote a low carbon-footprint, and to protect our tropical environment, several businesses are dedicated to daily or weekly rentals such as: golf carts, scooters, bicycles, and other types of unique transportation that's efficient and fun. Old Town Trolley Tours, has a hop-on hop-off Trolley that will get you around town with 13 different stops along the route. You can shop, eat, and sight see at your leisure and then board the train for the next adventure. The Conch Tour Train, established in 1958, is a 75 minute historic sightseeing tour that will give you fun facts and history while you tour Key West.brbrOther Things to Note:brSelf check-in; contactlessbrbrInteraction with Guests:brDuval Street Suites would appreciate the opportunity to host your stay in Key West! Please feel free to send us an email with any questions or request you may have. We are happy to help!
Bed 3

Bed

Bath 3

Bath

Sleep 9

Sleeps

Slider Thumb

$909.34

/ Nightly
Condo

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

Key West, Florida, United States

YOUR OCEANFRONT OASIS AWAITS...brThis remarkable and magical retreat is sure to provide all the R & R you need to refresh your soul. Peacefully located in Key West Beach Club community just minutes to downtown and Duval Street. This sweet and newly renovated haven encompasses every conceivable amenity you could desire while in Paradise.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrPLEASE NOTE...brThis home has a 6 night minimum as required by the HOA of the community. The renter will be asked to send photos of all adult guests upon booking as required by the HOA.brbrDETAILS AND AMENITIES...brLocated at the top floor of this desirable community, this unit is sure to take your breath away as soon as you walk through the front door. Find a bright and open space with natural lighting pouring through a multitude of windows with cool tile and hardwood flooring throughout and soaring ceilings creating a cheery gathering space. A fully equipped kitchen allows for seamless mealtime prep with convenient bar top seating for 4 and an indoor dining table for 6. Cozy living room furnishings are steps away with a TV and breathtaking views of your ocean front porch beyond. Enjoy a writing desk for those working remotely! This home is 0.2 miles from Higgs Beach and 0.8 miles from Smathers Beach.brbrSLEEPING ARRANGEMENTS...brFind a primary suite steps from the living area with a king bed, TV, en suite bathroom with a shower and direct access to the outdoor balcony. Another king guest room resides on the 1st level with a TV and hallway bathroom nearby with a shower. Head up to the 2nd floor to find a room with 2 twins that can convert to a king with a TV and another king guest bedroom - both with TVs and a shared hallway bathroom with a shower. A sofa sleeper occupies the living area for additional sleeping arrangements. brbrOUTDOOR LIVING...brCatch a breath of fresh air out on your private and spacious outdoor balcony with priceless views of the sparkling, turquoise ocean beyond. Enjoy plentiful seating as you hear the tranquil ocean waves below and soak up island life. Two pools reside on property with a community grill, tennis court, fitness area and elevators to this unit. This property is just a stone's throw to White St. Pier, Salute on the Beach restaurant and a short drive, bike ride or Uber into town. Higgs Beach is down the walking path from this community 0.4 miles and Smathers Beach is 1 mile in the other direction! Pickle ball and tennis courts are across the street from Higgs Beach.brbrPARKING...brThere is access to one parking spot on property, and plenty of street parking is available in this area for any additional vehicles. No vehicles over 18' long or over 80 wide. brbrPETS...brThis is not a pet-friendly home.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 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrGuests are only allowed to check-in on premises between 8:00 A.M. and 11:00 P.M.brbrAN UNMATCHED EXPERIENCE...
Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps

Slider Thumb

$193.48

/ Nightly
Apartment

EL JARDIN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w/ Pool!

Key West, Florida, United States

**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additional credit card fees.brbrISLAND TIME AWAITS…brThis tranquil island sanctuary calls your name awaiting peaceful moments and endless memories with your loved ones. Nestled within the Old Town district of Key West, this well appointed 2 bedroom, 1 bathroom home greets you with lush vegetation at every corner of this property creating a sensation of tranquility. Well equipped with all the everyday comforts of home paired with desirable modern luxuries, this haven is sure to welcome you into an unforgettable adventure. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brStep inside to find your cozy island abode boasting bright, natural lighting creating a cheery space. Sprawl out in the cozy living room that includes a flat screen TV and bookshelf full of novels for a rainy afternoon. A fully equipped kitchen lies nearby equipped with stainless steel appliances for meal prep which can be enjoyed at the indoor dining table for 4. Perch the doors open creating a lovely indoor/outdoor space with a sweet island breeze. brbrSLEEPING ARRANGEMENTS…brThe first guest room comes with a comfortable queen bed, flat screen TV and closet space for your belongings. The second guest room can be entered off the kitchen through double barn doors and includes a trundle bed, armoire storage and French doors leading out to the garden for your morning cup of coffee. Both guest rooms share a jack and jill full bathroom equipped with a walk in shower and newly refinished antique soaking tub. brbrOUTDOOR LIVING…brFind your serenity within the lush outdoor space as you calm your island soul in peaceful surroundings. Enjoy a dip pool which comes heated in the winter months followed by an evening under the stars in the rocking chairs or hammock. Grill out on the BBQ and dining al fresco with seating for 4 as you map out your next day's adventures. Peacefully located, this home allows for the best kind of R & R with only a short ride into town or the sandy beaches of Key West. 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. 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 does not have designated parking but there is on street parking in the surrounding neighborhood.  Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.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).brbrFIND YOUR WANDERLUST…
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(5)

$160.45

/ Nightly
Apartment

LA ENTRADA ROSA ~ Charming 1 Bedroom, 1 Bathroom w/ Loft in Old Town!

Key West, Florida, United States

**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additional credit card fees.brbrTRANQUILITY AWAITS…brNestled in the Old Town district of Key West, this picturesque island home awaits the creation of your tropical adventure. A bright and cheery space within a beautiful and lush Key West setting, this home is sure to allow all your worries to wash away. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brWalk up to a lovely porch, perfect for soaking up your peaceful surroundings with a coffee in hand as you watch neighbors passing by. Step inside to a an inviting living space with cozy furnishings and a flat screen TV. Find a small kitchen steps away to craft up your happy hour snacks and cocktails before a night out on the town. The washer/dryer is accessed from the exterior of the home and is shared with the rear unit. This property is equipped with a Ring Doorbell located next to the front door of the home. brbrSLEEPING ARRANGEMENTS…brEnjoy a peaceful night's rest in a comfortable full bed with a bathroom steps away with a shower tub combo. An upstairs loft with a twin mattress, or a queen Murphy bed down below can be used for additional sleeping arrangements. br***We recommend 3 adults max in this home.brbrOUTDOOR LIVING…brPeacefully located, this home allows for the best kind of R & R with only a short ride into town or the sandy beaches of Key West. 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.brbrPETS...brNo pets please.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood.  Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.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!brbr**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additional credit card fees.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrSUN IS SHINING, THE WEATHER IS SWEET…
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(7)

$859.44

/ Nightly
Private Vacation Home

The Mesa House - One block from Duval St

Key West, Florida, United States

Summary:brbrFamily-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else that Old Town Key West has to offer.brbrbrbrStep out on the deck of The Mesa House and breathe in the ocean breeze! This well-furnished home provides plenty of space to relax, ideal for families or groups. You're within walking distance of the docks, as well as the nightlife of Duval and the Key West Seaport. Stop by Cuban Coffee Queen for a cafécito or the seaport for water adventures!brbrbrbrThe Space:brbrThe Mesa House is made up of two condos that can be rented separately for smaller groups. Up to 10 guests can stay here in three bedrooms. Two full kitchens make meals easy for everyone.brbrbrbrCentral air conditioning keeps everybody comfortable. Four cable TVs and free WiFi are provided.brbrbrbrMesa House UnobrbrBedroom 1: KingbrbrExtra Sleeping: queen pullout couch in the living areabrbrbrbrMesa House DosbrbrBedroom 1: King brbrBedroom 2: Two TwinsbrbrExtra Sleeping: queen pullout couch in living area brbrbrbrBook The Mesa House for your group's next Key West vacation!brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrThis home is located in the heart of Key West's action, with plenty of dining and entertainment within walking distance, including historic Duval Street. Stroll a few blocks north to the docks, where snorkeling, boating, and other aquatic adventures await you.brbrbrbrHalf a block from Duval Street, The Mesa House, is steps away from Key Wests most famous bars and kitchens. Local’s favorite restaurants, such as First Flight, Bagatelle and Two Friend’s patio are less than a 5 minute walk from your front door. Got a sweet tooth Keep an eye out for Kermit’s Key Lime Pie Shop in the Historic Seaport known for the best Key Lime Pie in Key West, or grab some homemade fudge and candy from River Street Sweets.brbrbrbrForgot something or need a quick fix Shorty’s Market has your last minute necessities for your weekend getaway. Just 2 blocks away you can also find Fausto’s food market for locally sourced groceries.brbrbrbrGetting Around:brbrOne of the best parts of staying in Key West is how close in proximity you are to everything, this small little 2x4 island offers a variety of ways to get to and from your destination! Don’t feel like walking Peddle your way to breakfast, or take a bike ride along the water at sunset, by renting from Fury or Island Bicycles who offer both pick up & drop off of bike services! Feel like you’re on island time when you rent from Minty’s where you can enjoy exploring Key West on a scooter or golf cart! In addition to these non-traditional modes of transportation, you can also Uber, Lyft or Taxi to your next destination. Pink Taxi is an easy, reliable and affordable way for getting to your rental from the airport. brbrbrbrUnfortunately, there is no on-site parking for this unit. brbrFor overnight parking here are some parking lots:brbr• 204 Simonton Street (This is directly next to your unit and the most affordable on the island!)brbr• Caroline Street Outdoor Parking Lotbrbr• Park N Ride Old Town Garagebrbr• Fleming Street Overnight Pay to Park lotbrbrStreet parking information:brbr• There are pay-to-park spots and meters and it is free from 12AM - 8AM. With a 3 day limit.brbr• The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only” and visitors are NOT permitted to park in them.brbrbrbrOther Things to Note:brbrThere is no parking provided for this unit. However there is a pay-to-park overnight lot located directly next to your unit.brbrNo pets or smoking allowed.brbrPrivate washer and dryer
Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps

Home Most popular vacation rentals in Key West