Vacation Rentals By Owner In Key West, FL

$1495.86

Waterfront 4 Bed 4 Bath Home in Key Cove Landings

Key West, Florida, United States

Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Sailor's Son. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on private driveways leading to the house.brbrUNIQUE FEATURES:br2 EnSuite bedrooms, both facing the water with porch access. br4 Full Baths.brbrThis home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with a couch around a large HD flat screen Smart TV. There is a dining table with seating for up to 8 diners, with additional seating for 6 at the kitchen bar. brThe master bedroom has a King sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a King sized bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is also on the 2nd floor with twin beds, flat screen TV, and also with balcony access. On the main floor there is a fourth bedroom with twins bed. There is a full bath down the hall for convenience.brOut back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. brAMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. This property will accommodate 8 adults.brbrDockage is not available at this home's development.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).

4

Bed

4

Bath

8

Sleeps

$921.13

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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

Bed

Bath

Sleeps

$477.69

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

AN ISLAND STUNNER...brThis is the back cottage of the delightful Jewel Box Cottages compound, located in Old Town, just steps away from all the Duval Street happenings and the historic Seaport. This two-story gem offers 1714 sq. ft. of authentic island charm, with magnificent hickory hardwood floors throughout and whitewashed interior cypress wood interior walls. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter the home to a gorgeous and spacious contemporary kitchen which is a dream come true for culinary aficionados. This space is well-stocked with every modern appliance and cooking tool you'll need to concoct special meals for loved ones. This space flows into the plush living and dining areas where you can unwind with loved ones and watch your favorite shows on the wall-mounted TV. Sliding doors open to the backyard oasis and a bedroom with double-entry full bath completes the downstairs. A lovely balcony resides on the upstairs landing and overlooks the pool area. This home is equipped with Roku TV. This home has a mounted outdoor camera but is NOT in use during guest stays.brbrSLEEPING ARRANGEMENTS: brThere is a downstairs bedroom with an office space, queen Murphy bed and double-entry shower bathroom. The other two bedrooms are upstairs (one with a queen bed and the other with a king bed), ensuite shower bathrooms and large closets. The larger primary bedroom upstairs houses the washer and dryer in its oversized bathroom and also has a private door to the upstairs balcony. All upstairs bedrooms enjoy TVs. A sofa sleeper lies in the living room.brbrOUTDOOR LIVING…brEnjoy your sparkling heated pool with a waterfall feature, outdoor shower, and lounging chairs. Al fresco dining for 6 will delight your senses as you dine under sultry stars. Lose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. brbrPETS...brDogs are considered and a pet fee is required. Please leave the size and breed in the comments when inquiring.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrPARKING...brThere is a driveway for this home for 2 vehicles.brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrBRING ALL YOUR LOVED ONES…

Bed

Bath

Sleeps

$468.34

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

CONCH STYLE CHARM...brThis is the front cottage of the delightful Jewel Box Cottage compound, located in Old Town, just a stone's throw away from the magic of Duval Street and the historic Seaport. Abundant tropical foliage embraces the wrap-around front porch, inviting you to sit and people watch with your favorite beverage in hand. Wood floors and painted white walls line the space of this 1279 sq. ft. home that features vaulted ceilings and wooden beams and loads of Key West sunshine spills through multiple skylights.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brSophisticated island style greets you as you enter the home which features a beautiful, modern kitchen, complete with island, stainless appliances and everything you'll need to cook for friends and family. The adjacent living/ area offers plush seating with a couch (also a sleeper sofa), loveseat and cushioned chair and smart TV for your viewing pleasure. A stacked washer and dryer occupy the half bath which is located just off the living area. This home is equipped with Roku TV. This home has a mounted outdoor camera but is NOT in use during guest stays.brbrSLEEPING ARRANGEMENTS…brThere are 3 bedrooms, two with queen beds and one with a king bed. All bedrooms come with private en suite bathrooms with showers, ample storage space and two of the rooms include a TV. brbrOUTDOOR LIVING…brEnjoy your covered porch with a beautiful heated pool and outdoor dining for 6 as well as loungers for lazy afternoons. Lose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. brbrPETS...brDogs are permitted and a pet fee is required. Please leave the size and breed in the comments when inquiring or booking. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrPARKING...brThis home does not come with parking therefore guests must locate parking on the street in the surrounding neighborhood.brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrPICTURESQUE RETREAT…

Bed

Bath

Sleeps

$209.66

/ Nightly

Private Vacation Home

Gulf Getaway | Condo w/Pool!

Key West, Florida, United States

Summary:brConveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 bath perfect for your next island getaway. brbrIn addition to its prime location, this storybook corner unit features 2 private balconies off of each bedroom and a back deck equipped with all of your outdoor dining necessities. Close enough to everything, but just far enough away Gulf Getaway allows you to enjoy the peaceful serenity of Key West.brbrThe Space:brOn the second floor you will find the 2 bedrooms, each featuring a queen size bed, attached full bathroom and balcony. Perfect for accommodating 4-6 guests, additional sleeping arrangements can be found in the queen pullout couch on the first floor.brbrThe open first floor plan with a half bath is perfect for relaxing after a long day. Equipped with an LG cable tv, complimentary Wifi and French doors leading out to the back deck, the natural sunlight in Gulf Getaway keeps the space bright and airy. From an espresso maker, to a Keurig and smoothie maker, the rooster-themed kitchen is stocked with all of your cooking and drink necessities. There is also a hose outside for washing off sand from the beach and a private back entrance to make accessing the back patio a breeze.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit. brShared Community Features: This home also includes access to the neighborhood pool- exclusive to Truman Annex homes and has lounge chairs perfect for sunbathing. brHow to Access: the bedrooms are located on the second floor with stair access only.brbrThe Neighborhood:brExplore all that Key West has to offer including Truman Annex’s brand new Waterfront park and pier overlooking the Gulf. On Thursdays catch the sunset farmers market at the park or bring the kids to the splash pad for a fun-filled waterpark adventure. Just a 2 block stroll from the world-famous Duval Street, Gulf Getaway is walking distance to endless shopping and dining options.brbrGetting Around:brParking Information: There is assigned parking provided for 1 vehicle. We can provide you with recommendations for parking additional vehicles upon request.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrOther Things to Note:br- In the upstairs hall closet, you will find a stackable washer and dryer.br- Pets Policy: Pets are welcome!brOur requirements are as follows: br•40lb maximum per petbr•$250/per staybr•2 pet maximumbr- This home has a 28-night minimumbr- Mid-stay cleans are available upon request.

2

Bed

2

Bath

6

Sleeps

$473.28

/ Nightly

Condo

Island Links Escape

Key West, Florida, United States

Summary:brbr2 Bedroom 2 1/2 Bathroom Townhouse in Key West Golf ClubbrbrbrbrThe Space:brbr**Beautiful 2-Bedroom Townhome in Key West Golf Club**brbrbrbrWelcome to this charming 2-bedroom, 2.5-bathroom townhome located in the highly sought-after Key West Golf Club community. This home features a spacious and unique yard, perfect for outdoor relaxation and entertaining. Enjoy serene views from the balcony, making it the perfect spot to unwind after a day in paradise.brbrbrbrThe gated community offers excellent amenities, including two sparkling pools, a fitness center, and parking for two vehicles. Nestled in a quiet neighborhood, this townhome provides the perfect balance of peaceful living and convenient access to everything Key West has to offer.brbrbrbrJust minutes away, you’ll discover some of Key West's best-kept secret restaurants loved by locals. Plus, you're only 10 miles from the vibrant energy of Duval Street and the famous downtown area. Close to beautiful beaches and all the island’s top attractions, this home is ideal for those looking to enjoy the best of Key West living.

3

Bath

5

Sleeps

Exceptional(4)

$880.6

/ Nightly

Private Vacation Home

The Most Perfect Old Town Key West Location for a Retreat!

Key West, Florida, United States

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny and bright, with beautiful furnishings and every amenity you could want. The bathrooms are conveniently located and can accommodate larger groups, and now have fabulous Japanese-style bidets. The gourmet kitchen is well equipped, and looks out (via large folding sliding glass doors) on a covered outdoor living space, with chaise and dining table. The pool is just steps further, surrounded by lush tropical plants. Sunbathing here or on the upper deck is a must. In the evening, the large upper deck has string lights- a perfect environment for drinks, dessert, or conversation. brbrThe house AC throughout, WiFi, and TVs with Apple TV in every bedroom. brbrIf you're looking for the real Key West experience, A Thousand Hidden Hemingways is the place. And if you wander around our neighborhood, you just might find some more like minded folks...

4

Bed

3

Bath

12

Sleeps

$166.83

/ Nightly

Private Vacation Home

Monthly rental-Old town one level home w/ shared, heated pool, parking, a/c,heat

Key West, Florida, United States

*Key West only allows us to rent the home for 28 nights minimum, so I won't be able to respond to inquiries for rentals shorter than that time frame* Owner prefers the calendar month starting the 1st and last day of month. Exceptions can sometimes be made. This is a 1 level home with only 3 stairs up to the home. It has 1 bedroom 1 bath with a walk-in shower. It is a single family home that is 800 sq. ft., located just 7 blocks to Duval and a 10 minute walk to Higgs beach. This home is in a quiet community and shares a beautiful courtyard area with 11 homes surrounding a large heated swimming pool and is ideally located within easy walking distance to the beach, world famous Duval Street, shopping, museums and restaurants. We ask that only guests that have great prior past reviews on file request to book the home. You will love the heated, shared pool and beautiful courtyard along with the side deck and front porch. You will love being close to everything including the grocery store, coffee, beach and more. It has a Walk-in shower. 1 designated Parking space. Shared heated pool. Home has a/c and heat- 2 mini splits. All Utilities including internet and basic cable. There is 1 queen bed and 1 pullout double bed in the front living room. Great for 2 people as the bathroom is in the bedroom so if you have guests they will have to enter your bedroom to get to the bathroom. Located on Catherine St. at Watson. 1 designated parking space in front of home with room for a motorcycle too. The other side of the street is open parking for anybody to use. No laundry on site. There are 3 laundry mats all within a few blocks and one will pick up and redeliver your clean laundry. This is not a home for parties and you can only have your designated registered guests staying overnight at the home and a couple others maximum at the pool as the pool is shared and its quiet. This home has a front porch along with a large side deck overlooking the garden. There is also seating at the pool. It has very high ceilings so it feels larger than it would seem. The bedroom has a door to the addition on the back of the home and then french doors to the deck and a door to get to the pool. No smoking allowed inside or at the pool. The home is from 1906 and has original flooring, windows, bath, and kitchen cabinets so it's not in perfect shape and you can tell those things are older. The addition in the back of the home is new, some windows in the kitchen storage area and bath are new, and the deck is new . It may be considered by some to need some updating such as the kitchen, baths, floors. The floors are original. The bath tile is original. The kitchen has new cabinet doors (refaced). Owner allergic to cats. Small dogs under $20 pounds are ok with $300 non refundable pet cleaning fee. No cats as owner is allergic. Dogs are not allowed to be off leash anywhere outside In the yard or in the courtyard where the pool is. The yard and the courtyard all run together with no fence so your pet would need to always be on a leash in the front yard or side yard or back yard. The neighbor next door has a small dog. Located within blocks of beaches, shops, restaurants, and museums! If you're here for the sand and sun, several local beaches are located less than a mile from your rental. Cast a line, people-watch, or enjoy the views from the Edward B. Knight Pier or Higgs Beach Pier, or head over to Duval Street for the area's best restaurants, bars, and boutiques. Begin your day with a refreshing dip in the beautiful, shared swimming pool, enjoy a meal out by the furnished pool and then kick back and watch the world go by from the front porch.brTravel insurance is recommended, as we cannot change our cancellation policy.

1

Bed

1

Bath

4

Sleeps

$178.12

/ Nightly

Private Vacation Home

The Sea Glass Cottage in Historic Key West

Key West, Florida, United States

Spend time in beautiful Key West and live like a local in a true Conch Home! The Sea Glass Cottage is perfect for groups with 4-6 guests. A fully-renovated (2022) two bedroom, two bath home with a pull-out sofa located in an historic local neighborhood in downtown Key West near beaches, parks, and cafés, including the famous Sandy's Cafe! Enjoy beautiful flowering foliage and fruit trees (mango, avocado, etc.) on your second-story private porch with ample seating and a grill. brbrThis is a beautiful second floor fully-renovated (2022) home with a classy coastal sea glass decor with wood floors, lots of windows, and an open floor plan for entertaining indoors or on the large porch with a dining area accommodating at least six with a grill and views of the garden and flowering fruit trees.brbrThe living area has high ceilings, a 70 flat screen Smart TV and a comfortable pull-out couch and love seat adjacent to the brand new kitchen which is fully equipped with stainless appliances. There is a Keurig coffee maker and a full range of appliances and kitchen tools for your cooking needs.brbrThe two beautifully appointed bedrooms both include an en suite bathroom with a shower and 65 inch flat-screen Smart TVs. The primary bedroom includes a king-sized bed, two nightstands and a bench with huge windows including a large transom window.brThe second bedroom has a queen-sized bed, two nightstands, a dresser and a chair. Both have high ceilings and lots of natural light with beautiful windows with a view of our foliage and fruit trees. The primary bathroom also includes a full-sized washer and dryer for the unit. The entire unit includes wooden Bahama Shutters to provide privacy and allow for a good night's sleep.brbrThree split unit ACs, Washer/Dryer, three flat-screen SmartTVs, wireless high-speed internet throughout the property. Fully-appointed kitchen. Linens, bath and beach towels provided. This property has off-street parking and will accommodate six guests along with a small pet.brbrKeyless door entry system and private off-street parking along with ample street parking are available.brbrReserve the sister cottage, the Coral Cottage, which is just downstairs, to accommodate parties of 8-10 in separate units within the same home.

Bed

Bath

Sleeps

$149.96

/ Nightly

Apartment

Beautiful Waterfront Studio- Dock your boat here! - 15 mi to Key West.

Key West, Florida, United States

What a VIEW!! Enjoy breathtaking sunsets right from home in this well-appointed, clean and modern studio. Picture yourself waking up in a king-size bed and enjoying a gorgeous view of the ocean every morning. Drink your morning coffee or juice outside on the private deck overlooking the water. Take advantage of our available paddle board, kayaks, noodles, and snorkel gear to get out there and explore or just jump in the water to beat the heat. Retreat to the shade of the deck or inside the air-conditioned comfort of your room. Enjoy the best of both worlds during your stay in the Keys. Only a 15 -20 min drive so you can enjoy everything Key West has to offer: excellent restaurants, exciting nightlife, shopping, museums, live music, etc (don't worry our guests will get a list of recommendations we know there are lots of tourist traps out there too). Then at the end of your day or night you get to leave all that Key West noise behind when you come back to the peace and tranquility of the bay. brbr*King-size bed has a memory foam mattress with high-quality linens. There is a small kitchenette inside with an apartment-size refrigerator/freezer, microwave, coffee maker, Nespresso maker, toaster oven, and all of the kitchen basics. Outside on the deck is a propane grill with 4 burners plus one separate burner on the side for use with a pot or pan (2 propane tanks are provided). There is also a kitchen sink with a good amount of countertop and storage out on the deck. The bathroom has 2 sinks, a large bathtub, a very romantic double shower, and an amazing view. There is a 32-inch smart TV in the sitting area so you may log into your own Netflix or other online streaming account. The unit has a small apartment-size washing machine for small loads of laundry. There is NO DRYER for your clothing. There is a clothesline and drying rack with clothespins (just like my grandma used to use. Works just fine)! There is parking for one vehicle. 28-night minimum stay.

Bed

Bath

Sleeps

$262.73

/ Nightly

Apartment

Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Key West, Florida, United States

Truman @ Duval Unit A | Perfect for a Getaway in Key WestbrbrEscape to this cozy, vibrant cottage in the heart of downtown Key West, where adventure and relaxation await just outside your door. Ideal for couples or solo travelers, this charming retreat offers the perfect spot to enjoy all that Key West has to offer, from historic landmarks to lively nightlife.brbrThe Ambiance:brThis quaint cottage is bursting with character and laid-back island vibes. While it doesn't feature a full kitchen, you'll have a mini-fridge to store your favorite snacks and drinks, perfect for keeping cool after a day exploring. With partial A/C, cable TV, and free WiFi, you'll have all the modern comforts while soaking in the island atmosphere.brbrGuest Perks:brEnjoy a hassle-free, contactless check-in with your personal entry code, and settle in to enjoy everything this vibrant area has to offer. With cable TV, free WiFi, and air conditioning, this cozy retreat ensures you'll always have a comfortable place to unwind after a day of island adventures.brbrNeighborhood Highlights:brLocated just steps from the intersection of Truman Avenue and Whitehead Street, this cottage puts the best of Key West at your fingertips. Take a short walk to the iconic Southernmost Point, visit the Ernest Hemingway Home, or grab a bite at one of the many local restaurants. Whether you're exploring the lively downtown area or catching a sunset on the water, this location is ideal for experiencing the essence of Key West.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- There is no parking available on-site, but we can provide recommendations for nearby parking options.br- The studio is located on the first floor for easy access.br- For your peace of mind, there are two security cameras monitoring the exterior entrances.br- Guests must be 25 years or older to book this property.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Bed

Bath

Sleeps

$345.36

/ Nightly

Apartment

Welcome Matt's - Truman @ Duval | Perfect Hideaway!

Key West, Florida, United States

Truman @ Duval Unit B | Ideal One-Bedroom Retreat for CouplesbrbrEscape to a charming one-bedroom apartment in the heart of Key West, the perfect spot for a romantic retreat or a weekend getaway. Recently remodeled with comfort and style in mind, this apartment offers all the essentials for a relaxing and memorable stay. Whether you're here to explore the vibrant culture, lounge on the beach, or enjoy a romantic evening, this apartment puts you right in the middle of it all.brbrThe Ambiance:brThis newly remodeled apartment is designed to offer a cozy, intimate space for couples. Featuring a comfortable bedroom, modern décor, and thoughtful touches throughout, it's the perfect place to unwind after a day of island adventures. The apartment comes with a well-equipped kitchen, including a fridge and coffee maker to start your mornings right. Beach towels are provided for your convenience, so you can easily head to one of the nearby beaches or enjoy a day in the sun.brbrGuest Perks:brEnjoy the convenience of free WiFi and a digital lock for easy, contactless check-in. The apartment also comes with essential amenities to ensure your stay is as comfortable as possible. Whether you're exploring the city, relaxing indoors, or taking in the island breeze, this apartment provides a perfect home base during your time in Key West.brbrNeighborhood Highlights:brLocated just steps from Duval Street, this apartment offers an unbeatable location to experience the best of Key West. Walk to local attractions such as the Southernmost Point, Hemingway House, and the Key West Lighthouse. For nature lovers, the Key West Butterfly and Nature Conservatory is just a short stroll away, and if you're seeking outdoor adventure, be sure to visit Fort Zachary Taylor State Park or relax at one of the beautiful local beaches. With a variety of restaurants, shops, and entertainment options nearby, you'll never run out of things to do.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dog with a $20/per dog per night fee.br- This studio is located on the first floor.br- For your safety, there are two cameras monitoring the entrances.br- There is no parking available on-site, but we can provide recommendations for nearby parking options.br- Guests must be 25 years of age or older to reserve this property.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrThis charming one-bedroom apartment in downtown Key West is the perfect choice for couples looking to enjoy a romantic and convenient stay in paradise. Book your getaway today and experience the magic of Key West!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Bed

Bath

Sleeps

$268.82

/ Nightly

Apartment

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Key West, Florida, United States

Scott's Cottage - Truman @ Duval F | Perfect Location! Ideal for Solos & CouplesbrbrLooking for a relaxing retreat in the heart of the Florida Keys This charming studio offers the ideal blend of comfort and convenience for your tropical getaway. Whether you're here to explore Key West's rich history, lounge by the beach, or soak up the vibrant culture, this vacation rental is the perfect base for your island adventures.brbrThe Ambiance:brThis charming studio is thoughtfully designed to maximize space and comfort. Equipped with a fully stocked kitchen featuring stainless steel appliances—fridge, stove, oven, microwave, blender, coffee maker, and toaster—you'll feel right at home while preparing meals. Enjoy your morning coffee or dine al fresco on your private patio, complete with an outdoor dining table. With free WiFi, cable TV, and AC , you'll have everything you need to relax after a day of exploring.brbrGuest Perks:brYour stay includes a contactless check-in for your convenience. Access your studio with a personalized code that ensures a secure and seamless arrival. Stay connected with free WiFi, cool off with air conditioning, and enjoy your favorite shows on the cable TV after a fun day out in Key West.brbrNeighborhood Highlights:brLocated just steps from downtown Key West, this studio places you right where the action is! Explore iconic landmarks like the Key West Lighthouse and the Hemingway Home and Museum, all within walking distance. Indulge in the island's cuisine, visit local shops, or enjoy the local nightlife—everything is just a short stroll away.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- This studio is located on the first floor.br- For your safety, there are two cameras monitoring the exterior entrances.br- There is no parking available on-site, but we can provide recommendations for nearby parking options.br- Guests must be 25 years of age or older to reserve this property.brbrCheck-in time: 3:00 PMbrCheck-out time: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrWhether you're here for a romantic getaway, a solo adventure, or to enjoy all the sights and sounds of Key West, this tropical studio offers the perfect spot to call home during your stay! brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

1

Bed

1

Bath

2

Sleeps

$1031.07

/ Nightly

Private Vacation Home

Casa Cristol- Family and Pet Friendly - Classic KW Charm Superb Location!

Key West, Florida, United States

Family friendly, secluded retreat within Key West Truman Annex gated community. Our lanai is a destination in of itself and makes this home extra special. We have some of the most comfortable bedding in Key West prepping you well for each day’s adventures. The fully-equipped kitchen is superb. Location Location Location. There is one vehicle carport, Duval is a block away, yet there is no clatter. This single-family home has three bedrooms and three full bathrooms. Private lanai area great for outdoor living and family dining and relaxing in the tropical atmosphere of Key West. Bring your emotional support or service animals so nobody is left at home, diminishing the experience for all. The entire home is available for your use and enjoyment. Just text if you need anything from dining advice to experience suggestions. We hope that you can stay with us.

Bed

Bath

Sleeps

$196.74

/ Nightly

Private Vacation Home

Poolside townhouse in Key West Golf Club

Key West, Florida, United States

Beautiful 2 bed/2.5 bath townhome in key west golf club. Pool steps away. Gated community. Enjoy everything beautiful Key West has to offer. Privately owned and operated. Get in touch to book your next getaway today!

Bed

Bath

Sleeps

$273.85

/ Nightly

Apartment

Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

Key West, Florida, United States

Truman @ Duval - Unit E | Cozy Getaway in the Heart of Key WestbrbrDuval Studio is your perfect launchpad for an unforgettable Key West adventure! Situated near the vibrant intersection of Truman Ave. and Duval St., wonderful studio offers a prime location just steps from some of the island's top attractions. Whether you're visiting the Ernest Hemingway Home and Museum around the corner or indulging in Duval Street's lively nightlife, you'll find everything you need just moments away from your door.brbrThe Ambiance:brThis quaint studio is designed for ultimate convenience and comfort. The open floor plan features a cozy sleeping area with everything you need to relax after a day of island exploration. A mini-fridge, coffee station, and microwave make it easy to enjoy a morning coffee or a quick snack between adventures. With free WiFi, cable TV, and AC , you'll have everything you need to relax after a day of exploring.brbrGuest Perks:brEnjoy a seamless, contactless check-in process with a personalized code. The studio is equipped with free WiFi for staying connected and planning your next outing. You'll also find plenty of local dining options within walking distance, ensuring you never run out of things to try!brbrNeighborhood Highlights:brThe studio places you right at the heart of Key West. From here, you can easily walk to the iconic Ernest Hemingway Home and Museum, just steps away, or visit the Key West Lighthouse, only a block from your front door. For a truly Key West experience, stroll down the lively Duval Street, where you'll find renowned bars, local restaurants, and all the excitement that makes this island so famous.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- This studio is located on the second floor.br- For your safety, there are two cameras monitoring the exterior entrances.br- There is no parking available on-site, but we can provide recommendations for nearby parking options.br- Guests must be 25 years of age or older to reserve this property.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrThis inviting studio offers the perfect balance of comfort and convenience for your Key West getaway. Don't miss out on this prime spot—plan your stay today!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Bed

Bath

Sleeps

$388.69

/ Nightly

Apartment

Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!

Key West, Florida, United States

Truman @ Duval - Unit D | Two-Bedroom with Full Kitchen & Prime LocationbrbrWelcome to your perfect family getaway in the heart of Key West! This charming two-bedroom, one-bathroom offers a wonderful combination of comfort, convenience, and prime location for your next vacation. Just a half block from the lively Duval Street, you'll be steps away from iconic attractions, restaurants, and the best of Key West's vibrant downtown scene.brbrThe Ambiance:brThis cozy home offers the ideal retreat for families looking to relax and enjoy the island life. With a spacious, air-conditioned living area, you'll have plenty of room to unwind. The fully equipped kitchen makes it easy to cook meals together, and the flatscreen TV provides entertainment for everyone after a day of exploring. The two bedrooms provide a peaceful, restful setting, ensuring you wake up refreshed and ready for another fun day.brbrGuest Perks:brThe property comes with a private parking space, ensuring you never have to worry about finding a spot. With free WiFi, you can easily plan your next outing, book tickets for local tours, or just stay connected. Whether you're preparing a homemade breakfast or enjoying a quiet evening in, this home has everything you need for a stress-free stay.brbrNeighborhood Highlights:brLocated just steps from Duval Street, you'll find yourself in the heart of Key West's action. Walk to Southernmost Point, explore the famous Mallory Square Sunset Celebration, or take a dolphin tour to experience the island's natural beauty. There are a variety of restaurants, bars, and cafes nearby, so whether you're craving fresh seafood or a casual bite, you'll find plenty of options. Plus, the nearby beaches provide easy access to sun and sand for a relaxing day by the water.brbrTransportation Tips:brPlease note that there is one designated parking spot on-site. Paid parking is also available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- The cottage is located on the first floor for easy access.br- For your peace of mind, there are two security cameras monitoring the exterior entrances.br- Guests must be 25 years or older to book this property.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrBook your stay at this cozy Key West home today and enjoy a fun-filled, relaxing family vacation in one of the world's most beloved destinations!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Bed

Bath

Sleeps

$298.24

/ Nightly

Apartment

Jerry's Escape - Truman @ Duval | Cozy Studio, Perfect Location!

Key West, Florida, United States

Truman @ Duval - Unit C | Cozy Studio Perfect for CouplesbrbrExperience your perfect romantic retreat, offering a charming and vibrant atmosphere right in the heart of downtown Key West! Whether you're here for the local culture, waterfront activities, or a peaceful island escape, this cozy condo is the ideal home base to experience it all.brbrThe Ambiance:brThis uniquely decorated one-bedroom condo is perfect for couples seeking a quiet getaway with easy access to the best of Key West. Located just off Truman Avenue, the condo boasts a bright and inviting living area, where you can unwind with free WiFi, cable TV, or simply enjoy the island's breeze through your windows. The cozy kitchen allows you to prepare your favorite meals, and the private patio is a perfect place for a romantic dinner under the stars or a delightful place to soak up the sun!brbrGuest Perks:brThis condo offers seamless, contactless check-in with a personalized entry code, ensuring your arrival is smooth and secure. Free WiFi and cable TV are provided for your convenience, and you'll enjoy the comfort of air conditioning as you relax in this intimate space.brbrNeighborhood Highlights:brLocated just a short walk from iconic Key West attractions, Key West Bliss places you steps away from the Ernest Hemingway Home and Museum and Key West Lighthouse. Stroll down the street to explore local shops, bars, and restaurants, or take a quick drive to Fort Zachary Taylor State Park and the Key West Tropical Forest and Botanical Garden for a day of outdoor adventures. Whether you're interested in history, nature, or just soaking in the island charm, you're right in the middle of it all.brbrGetting Around: Key West is incredibly walkable, so you'll have no problem exploring nearby attractions on foot. You can also rent bikes, scooters, or golf carts to explore the island at your leisure. While there is no parking available at the condo, public parking options are nearby, and we're happy to recommend convenient spots.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- The studio is located on the second floor.br- For your peace of mind, there are two security cameras monitoring the exterior entrances.br- Guests must be 25 years or older to book this property.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrBook your stay at Key West Bliss today and treat yourself to a memorable romantic escape in the heart of one of the most beautiful destinations in the world!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Bed

Bath

Sleeps

$452.91

/ Nightly

Private Vacation Home

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

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: As you enter the home via its white picket fence and comfortable front porch, you will be uplifted by sunshine. Hardwood floors and high-end finishes are reflected in this home while a bit of Key West charm is revealed. A first-floor queen bedroom is on your left and just two steps down into the home is one of three full baths. Moving on into the oversized wet bar area and living room, you can cozy up on the sofa or chairs and watch a little TV while sipping on your wine. This beautiful space includes blue/grey cabinets, a sink, open shelving, storage, and a laundry room. Looking out through the double sets of French doors, you will enjoy the lush vegetation that surrounds this home. Moving back towards the chef’s kitchen with slide in gas range and custom hood, you have all you need to prepare a gourmet meal or simply heat up a take-out meal. A Sub-zero refrigerator and stainless-steel appliances are complemented by white upper cabinets and beautiful natural wood lowers. Quartz counters, a double oven and built in microwave enhance this room. As if that isn’t enough space, moving further towards the rear of the home and pool, is a dining room with seating for six as well as a half bath; this area is open to a cozy family room with built in cabinets, TV, and a fireplace-imagine that! A wall of glass spills out onto the beautiful blue pool area. Enjoy a day or night swim, with plenty of privacy and loungers. Cook up your catch of the day on the outdoor grill. brbrThe second-floor houses two additional bedrooms with access to the porches. The primary king bedroom has a walk-in closet, nightstands, bedside lighting, dresser storage and a TV. Its bath has dual sinks, a glass walk-in shower, and a large soaking tub, perfect for relaxing after a night on Duval Street. The queen guest bedroom has dresser storage, nightstands, bedside lighting, and a TV. The beautiful ensuite bath is tiled and includes a glass walk-in shower. brbrBED CONFIGURATION: The first-floor bedroom has a queen bed. The second floor includes a king bed in the primary bedroom and a queen bed in the second bedroom. brbrOUTDOOR AMENITIES: Lush landscaping provides privacy around the pool with lounge chairs and gas grill. The pool is heated seasonally (November-April) for an additional fee which will be assessed at the time of booking. An outdoor shower completes the Key West vibe!brbrPARKING: There is no designated parking space, but street parking is available throughout the neighborhood.brbrLOCATION: Old Town, north of Truman Ave in a quiet residential area within walking or biking distance of several shops, galleries, and restaurants. brbrPETS: This home is NOT pet-friendly (If you have pets, please browse through our many homes that are pet friendly).brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Managed by Historic Key West Vacation Rentals***

3

Bed

3

Bath

6

Sleeps

$1388.54

/ 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...

4

Bed

3

Bath

8

Sleeps

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