Vacation Rentals By Owner In Key West, FL

Welcome aboard the The Thirsty Lady with 3 bedrooms and 3 baths, your own private Sailboat that also includes your Sailing Excursions for up to 6 people. If you were looking for a Unique, Memorable way to experience and enjoy Key West then THIS IS IT!! You stay in amazing 5 Star Marinas each night and Sail by day, all included. If you book 2 nights that includes a Sunset Sail your first night of arrival and 1 full day Reef Sail. Book 3 nights and receive 1 Sunset Sail and 2 Full day Reef Sails and so on. We book 2 nights minimum and 4 nights max.. We always do the Sunset Sail your first night of arrival and then a day Sail is included for each day.brbr**Please understand that even though 1 Sail is included for each day you book doesn't mean you have to use them all. We have found that guests who book 3 or 4 nights sometime forgo a Sail or 2 to have a free day to do what they wish. It is totally up to you whether or not you use all the Sails included and you can decide as you go when you arrive **brbr We have years under our belt offering these charters and have decided to join the VRBO family to extend our reach. We are here to cater to all your special needs to make sure your experience with us will land in your top favorite vacations EVER! We provide the Captain, Captain Pat, a USCG 100 Ton Master Captain. brbrThe first night of arrival we take you on a Sunset Sail and that night you will be docked at a beautiful Upscale 5 Star Marina that boasts 6 pools, Restaurant & Bar, 24 hour pristine Bath House, and free shuttle all available for you use. There are bathrooms on the boat but you will want to use the Bath House for showering located just steps from the boat.. brbrThe 2nd day we take you on a full day Sail to the Reef where you can swim, snorkel and Just Relax! The 2nd night you will be docked at another Amazing Upscale Marina. All the marinas offer amazing amenities including pools, bars, restaurants, and free shuttles. If you stay a 3rd night we take you on another day sail the 3rd day and you will stay back at the 5 Star Marina you stayed the 1st night. We do offer free parking for your entire stay and if you are carless there are free shuttles available to you and we can help you with rides when available. We also provide all your water, ice, and sodas for the length of your stay along with all your life jackets, safety gear, fresh linens and towels and snorkeling equipment. You are responsible for your meals but there is a small kitchen aboard with a fridge, freezer, toaster, and a small stovetop/oven. There are plenty of Restaurant/ delivery options available to you as well. Most people just pick up light snacks and lunch items to make sandwiches for their Day Sails. There is also a dining table that seats up to 6 people. brYou are responsible for your own alcohol but we usually have a pretty well stocked bar you are always welcome to. You are welcome to anything you see in the cabin! If you would like me to remove the alcohol from the boat please let me know.brThis is your own PRIVATE SAILBOAT made available to you with your own Private Captain that is only there when you are going out Sailing. The rest of your time off the water the boat is all yours. Captain Pat will only be there when you need him. We are 100 percent on call when you are staying with us so we will always be available if you need us. This trip is perfect for couples, friend get togethers and amazing for families!! We have hosted them all and every summer we Captain the boat out to the Boy Scouts of America. Please understand this is a Sailboat so space is limited in the cabin and the rooms are small but there is cold A/C and extremely comfortable to sleep on. The Front bed is a Queen and the back bedrooms are double/fulls. The beds will sleep 2 comfortably but you better like each, lol..What we are offering is something so different from what everyone else is doing and we so look forward to hosting all ofbr you!! Please message us with any questions! brbrSample Itinerary:brbrDay of Arrival:brGuests usually arrive between 1-4pm. We will greet you and show you around and get you acquainted with the area and boat.br4:30-6pmish is a Sunset Cruise (subject to change when Sunset times change)brThe first night you will be docked at a 5 Star Upscale Marina which has 6 pools, a Restaurant & Bar, 24 hour bath house, Gym, and a free Shuttle that will take you downtown and back. brbr***You have to arrive by 4pm the latest on your arrival day if you want to take advantage of the Sunset Cruise*** brbrThe 4pm cutoff time will change throughout the year as Sunset times change. The other half of the year is a 5pm cutoff time when we leave the dock for when the Sun sets later in the evening and so on. brbrDay 2:brWe meet you back at the boat around 9-10ish am (you let us know what works for you) and we Sail you out for a full day at The Reef where you can swim & snorkel. You dictate how long we stay out for but usually we get back to dock around 3 or 4, all up to you. The 2nd night we take you to another beautiful Marina in Key West. All the marinas have pools, restaurants, bars and free shuttles. Basically Sail by Day and then you are free to leave the boat and explore Key West by afternoon/night.brbr3rd day:br If you chose the 3 night stay we take you on another Day Sail to a different part of the reef and the 3rd night you will be docked where you were the first night. So basically if you book 2 nights that includes 2 Sails and 3 nights you receive 3 Sails.brbrWe also offer 4 night stays which would include an extra Sail.

House Boat

All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6

Key West, Florida, United States

Bed

Bath

Sleeps

$627.75

Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only a few miles from Old Town. The property is on a corner of the island featuring its own private beach, a rarity in Key West. Located 2.7 miles from Smathers Beach and 3.8 miles from the Ernest Hemingway Home & Museum, this quiet piece of Key West is the best location for relaxation. The property is on a corner of the island featuring its own private beach and water access.brbrThis light and airy two bedroom, two bath condo is spacious enough to accommodate up to six guests. It features complimentary wi-fi, a flat-screen TVs, a washer and dryer, and a fully furnished balcony. The primary bedroom features a king bed with an ensuite bathroom. The bathroom features a large walk-in shower and a large vanity. The guest bedroom has a king bed and access to a full bathroom as well. The living room features a sleeper sofa, while the separate dining area features a large table for six. Prepare meals in the fully equipped kitchen with full-size refrigerator, microwave, stove, oven, coffee maker, dishes, utensils, and cookware. brbrAmenities include an outdoor pool, a jacuzzi, a private beach, dock, concierge, and a delicious restaurant with Bay views. There's also a bar, concierge, business center, complimentary parking, and onsite grills.brbrUnits are assigned at check-in, pictures are representative of the unit, and decor, layout, and room view may vary.brbrComplimentary parking is available for the first vehicle. Height restriction is 6 feet 8 inches. A $10 charge per day, per vehicle, applies for additional vehicles. Additional parking is subject to availability. There is no RV parking available.brbrThis is a Cashless Resort and credit cards are the only acceptable form of payment.brbrResort fee of $20/day is due at check-in. (Subject to change at any time)brbrThis property welcomes ADA service animals. Pets are not permitted.brbrLate Arrivals - Check-in is from 4:00 pm to 11:00 pm. If arriving after 11:00 pm, advance arrangements must be made by calling the property's Front desk.brbrA split week fee of approximately $80 may apply for reservations shorter than one week. (Subject to Change).brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

Condo

2-Bedroom Villa at Hyatt Beach House! Quiet Beachfront Location! Sleeps 6

Key West, Florida, United States

Bed

Bath

Sleeps

$459.37

Fully renovated and furnished 2 bedroom,1 bath cottage in a lovely tropical setting across from the cemetery in Old Town Key West. Only the finest finishes (marble, stainless, dade county pine) in the historical style meant for this special home. Small private cocktail pool, 2 separate outdoor spaces, fully furnished including antiques, screened porch, Comcast cable and Wi-Fi, outdoor shower, central air and heat, washer/dryer, barbeque. Parking space available by request.

Paradise found! 2 br/1 bth restored Old Town home with private cocktail pool

Key West, Florida, United States

Bed

Bath

Sleeps

$617.73

Tricksy's Place located in the heart of Old Town, Key West is a perfect retreat to relax, and the perfect starting point to explore all that our beautiful tropical island has to offer. Only one block from Duval St., a short walk to the Southernmost Point, Hemingway House, Key West Lighthouse, and more. Stay in and cook an elegant meal in our modern kitchen, or walk one block to Duval to the many restaurants and bars that Key West is famous for or do some shopping at the numerous unique shops.

Location, location, location in the heart of Old Town!

Key West, Florida, United States

Bed

Bath

Sleeps

$1782.2

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrIf your idea of a vacation includes pampering yourself and indulging in the finer things in life, then a stay at the DUCHESS OF CATHERINE will be your cup of tea. This newly built, professionally designed home is fit for a King and offers plenty of space for all the members of your court. Located on Catherine Street, just steps from Duval Street, you couldn’t ask for a more centrally-located vacation rental. The spacious interior includes five suites (each with an en-suite bathroom) and a versatile Media Room. Outside, the private backyard features a splendid, heated pool and enough space for everyone to spread out or come together for a poolside BBQ. Your stay at DUCHESS OF CATHERINE also includes Last Key Realty's Five-Star Guest Services & Complimentary Concierge, ensuring you’ll feel like royalty.brbrTHE LOCATION…brbrIf you decide to pull yourself away from this beautiful home, you’ll realize that the best Key West restaurants, live entertainment, and attractions are all within a few blocks of your front door. While you won’t need a car to get around from this fabulous location, there is off-street parking in the driveway for one vehicle if you decide to bring one. If you don’t have a vehicle but want to explore the island in a fun way, Last Key Realty’s concierge service can assist with a golf cart, scooters or bike rentals.brbrTHE LIVING AREA & KITCHEN…brbrDUCHESS OF CATHERINE was designed and furnished with comfort in mind. The open living area is ideal for gearing up to head out on the town or for unwinding after a day full of adventure on the water. The spacious living room has a large flat-screen Samsung Frame TV that can be enjoyed from the two plush sofas or chairs. The fully equipped kitchen is next to the living room, with every appliance and tool needed to prepare a meal at home. The extra-large dining table seats 10 and there’s additional seating at the kitchen bar.brbrTHE PRIVATE POOL…brbrNo royal vacation is complete without a private pool to spend your days relaxing in. The fully fenced private pool area gets equal amounts of sun and shade throughout the day. Your private saltwater pool can be heated in the cooler months upon request. Kick back poolside in the chaise lounges or gather the group for an outdoor BBQ using the propane grill and outdoor dining set.brbrTHE ACCOMMODATIONS…brbr** Florida Suite: Located on the First Floor with a King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Paddleboard Suite: Located on the First Floor with Two Twins OR One King bed, a flat-screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbr** Media Room: Located on the First Floor with a sofa that pulls out into a Queen to accommodate extra guests and a flat-screen TV.brbr** Whale Suite: Located on the Second Floor with Two Twins OR One King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Flamingo Suite: Located on the Second Floor with Two Twins OR One King bed, a flat-screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbr** Aviary Suite: Located on the Second Floor with a King bed, a flat-screen TV, a closet, a trundle bed with two twin mattresses, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room & All Bedroomsbr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced Yardbr** Private Saltwater Pool (with Pool Heat for $30/day)br** Propane BBQ Grillbr** Off-Street Parking for 1 Vehiclebr** Queen Sleeper SofabrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 14 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**DUCHESS OF CATHERINE @ DUVAL** Brand New Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$537.33

Everyone enjoys time in Key West, and staying at The Orchid Oasis take it to a new level. We are a family of Conchs that have been born and raised in Key West for seven generations, and we look forward to welcoming you to stay in our home. brbrThis home is located just minutes from everything that's great about Key West. You can walk or ride a bike to both Smather's Beach or Higgs Beach in under five minutes, and you're just two minutes from White Street pier where you can watch the most amazing sunsets you'll ever see!brbrOur pictures show you all the great aspects of this home so be sure to look through them to get a good feel for the house and the layout. brbrWe offer all the comforts you need for your stay in paradise including WiFi, flat screen TVs, laundry, lovely and inviting pool with waterfalls and ample parking space. There is a 4 person maximum limit to this home (NO EXCEPTIONS). brbrThis home is in a quiet area of Key West and is not recommended for parties or group celebrations. We ask you to please be respectful of the neighbors and keep the noise level to a minimum.brbrWe can also provide home cooked meals for an additional fee! Want authentic Cuban roast pork with rice and black beans and the best Key Lime Pie on the island Or maybe a custom made batch of Key Lime Fudge made by the woman who invented it Or Key West Pink Shrimp & Cheese Grits WE CAN DO THEM ALL! brbrThis property has a ONE MONTH minimum stay requirement.brbrNOTE: We are VERY selective about who we rent to! This home is right next to our primary residence so we only rent to couples or groups of four or less. If you are coming to party, be loud and make a mess please don't even inquire. We want tenants who are going to treat this home like they're own.

Orchid Oasis - Only Minutes from Smather's and Rest Beaches!

Key West, Florida, United States

Bed

Bath

Sleeps

$435.38

Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include:brbr2 bedrooms 1 bath {queen and 2 twins (or we can convert the 2 twins to a king bed with a king converter) plus a sleeper sofa in the living room.brbrFully equipped kitchen with upgraded appliances and cooking accessories.brWasher & dryer with iron & ironing board.brAll towels and linens, including beach towels.brCentral air & ceiling fans.brSecond floor condo with outdoor balconies (or ask us about renting both an up and down Shipyard condo for even more room)brLarge shared Shipyard pool located just steps away.brFlat Panel TV's and entertainment center.brHigh speed internet with Wi-Fi.brAssigned parking spot for 1 car.brbrLocated in prestigious Truman Annex at Mile Marker 0 - location, location, location. Shipyard Condos are right at the entrance to Ft. Zachary Beach and next to Mallory Square and those famous nightly Sunset Festivals and just two blocks from Duval Street and all of the shops, restaurants, night clubs and museums. While we provide a parking spot, you will not need a car! brbrExcept for festivals such as Fantasy Fest, Meeting of the Minds, and Powerboat Races, we generally require Saturday-Saturday rentals so if your dates are not Saturday-Saturday please email us with your dates prior to booking so that we can check our calendar to see if an exception is possible. brbrWe have many other Key West Truman Annex vacation rental listings that can be accessed via VRBO. Let us know if you have a particular interest or property size in mind.

Condo

Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0

Key West, Florida, United States

Bed

1

Bath

4

Sleeps

$610.73

Searching for the perfect vacation home away from it all Your hunt ends in here! A Wave from it All is a remodeled and tastefully decorated 2-story townhome with its own private pool that epitomizes island living at its finest while offering all the comforts of home. Best of all, this home is nestled in the Truman Annex, a palm tree lined residential community with many historic buildings including the Truman Little Whitehouse, walking distance to many of Key West’s finest dining establishments, two blocks from the world-famous Duval Street, two blocks from the nightly sunset celebration at Mallory Square, and less than a half mile from the beach at Fort Zachary Taylor State Park. Break away from the ‘high seas’ of everyday life while you settle into for what’s sure to be a memorable Key West vacation!brbrThe double set of sliding glass doors on the back of the home open up to provide a private spacious tropical oasis of indoor/outdoor living space with a private pool. A large flat screen HD SMART TV hangs on the wall in front of comfortable seating options. The fully equipped kitchen has all the appliances and tools needed to prepare meals at home, on those nights that you chose to dine home with your pick of indoor or outdoor dining.brbrTruman Annex is the most exclusive private residence community in Old Town Key West. Located just off the main drag of Duval Street, The Truman Annex is an oasis of calm, quiet palm tree lined streets with many historic homes, 24-hour staff and restricted access in the evenings where you can use the entry gate keys to come and go on foot.brbrProperty includes..brCentral Heat and A/C, Ceiling Fans, Flat Screen TVs in Living Room & All Bedrooms, Fully Equipped Kitchen, Laundry Room with full size Washer and Dryer, Starter supply of paper products & cleaning supplies, Linens and Towels provided, Wireless high-speed Internet access & full cable included.brbr** Fully Fenced & Lushly Landscaped Private Yard with Pool. Pool can be heated for an additional charge.brbr** Designated Covered Off-Street Parking (one space)brbr** This property will accommodate up to 4 adultsbrbr** No Pets Allowedbrbr**The entire property is NON smoking or vaping

Tropical Oasis in the Truman Annex with a private pool

Key West, Florida, United States

Bed

Bath

Sleeps

$328.81

CLASSIC OLD KEY WEST HOME...brThis home is boasting a rare combination of location and character. A mix of historic details and modern charm are evident throughout. Perfect for couples traveling together or those who have visitors during their stay in Paradise.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES.... brWalk in the door and be surrounded by Dade County pine and wood flooring. The main floor offers a large living room that is convenient for work and play and indoor dining for 6. You will find a full bathroom off the living room with a beautiful claw foot tub, pedestal sink and original mosaic tile. There is a fully stocked kitchen which over looks the private yard. Fabulous natural light through an abundance of wood windows finished in bright white moldings to compliment the home. The second floor is where the bedrooms lie in wait. There is abundant storage upstairs as well as the second full bathroom. brbrSLEEPING ARRANGEMENTS....brThe two bedrooms are located up the original wood staircase on the second floor. The master bedroom has a comfortable queen size bed, sitting area and a French door that opens to the rear deck. This room comes with a flat screen, smart TV so you can catch all your favorite shows on Netflix! There is an ensuite full bathroom with a shower stall and pedestal sink. The guest bedroom has two twin beds that can be converted to a king upon request. The hallway has a trundle bed with two twin beds. The downstairs living room has a sleeper sofa. br brOUTDOOR LIVING...brStep onto the front porch where there is seating to people watch while you take your morning coffee. If privacy is what your searching for then you can enjoy the refreshing dip pool with a beautiful backdrop of manicured tropical landscaping. Gather together under the pergola with cozy outdoor furnishings or enjoy dining together at the bench style table with plenty of seating available. brbrLOCATION...brThe location of this home is perfect for strolling through Old Town looking at the historic homes. Just a few blocks away you will run into Simonton & Duval street's where shops, galleries and restaurants line the area. There is always plenty to do or see like watching the sun set at Mallory Square or catching the Conch Train to hear the history of the island and how it became the coveted retreat it is today for visitors from all over the world!brbrPARKING...brOn street parking is available in the surrounding area for this home. Please park in unmarked spaces as residential permit spaces are only for Key West residents.brbrPETS...brPets are considered at this property and a pet fee is required. Please include the size and breed in the comments.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).brbrLOCATION IN PARADISE!

ORCHID ESCAPE~ 2 bedroom 2 bath set in Old Town with private dip pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$290.22

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrWhen you think of Key West, you think of spending relaxing days with your toes in the sand under the palm trees, and fun-filled nights walking through the Streets of Old Town on your way to catch the sunset at Mallory Square. Experience these kinds of days (and nights) at SOUTHERNMOST PALMS, a beautifully renovated villa, located at The Foundry in Truman Annex, Key West's most exclusive gated community. From this location, you'll be within walking distance to all that Key West has to offer. SOUTHERNMOST PALMS combined with Last Key Realty's unrivaled Guest Services is sure to make your stay in Key West a memorable one. Smoking is not permitted in any Last Key Realty home. In addition, the Foundry does not permit smoking in the front garden patio areas or balconies. Therefore, this home is not a good fit for vacationers needing smoking accommodations.brbrTHE LOCATION...brbrYou'll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town Key West, yet you'll benefit from the peace and quiet that Truman Annex is known for. Although you won't need a car to get around from this excellent location, there is a reserved off-street parking space.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE LIVING AREA...brbrSOUTHERNMOST PALMS has been furnished and decorated in a lush tropical style that can be found throughout the home. The living area is the entire first floor and has an open plan, with 11-foot ceilings and double French doors that provide plenty of natural light to enter. There's a large flat screen TV and multiple comfortable seating options, including a plush sleeper sofa to accommodate extra guests. There's also a convenient powder room located on the first floor. The kitchen has top-of-the-line stainless steel appliances, with granite counter tops and all the tools needed to prepare a meal from home. The indoor dining table seats six comfortably or enjoy an outdoor meal at your own private courtyard out front, with an outdoor dining set and a gas BBQ grill.brbrTHE COMMUNITY POOL and FORT ZACHARY TAYLOR STATE PARK...brbrThe landscaped community pool is located just around the corner and across the street, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile away from your front door.brbrTHE ACCOMMODATIONS...brbr• Master Suite: Located on the Second Floor with a King bed, a large flat screen TV, a private balcony, a large closet, and an en-suite bathroom with a walk-in shower.brbr• Second Bedroom: Located on the Third Floor with Two Twins OR One King bed, a flat screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbrEach floor closes off with its own separate door as well for extra privacy.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fansbr• Flat Screen TVs in Living Room & All Bedroomsbr• Fully Equipped Kitchenbr• Basic stock of spicesbr• Starter supply of paper productsbr• Starter set of cleaning productsbr• Linens and Towels providedbr• Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Community Pool Accessbr• Propane BBQ Grillbr• Assigned Off-street Parking for 1 CarbrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 6 adultsbr• Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**SOUTHERNMOST PALMS @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES.

Key West, Florida, United States

Bed

Bath

6

Sleeps

$701.13

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions. brbrTwo of the Queen bedrooms share an en-suite bath easily assessable from either bedroom. It features a very large walk-in shower. The 3rd bedroom features a full sized bed, walk in shower and private entrance. The quaint living room has a new L Shaped Sofa that provides plenty of additional sitting room for kicking back and chill time.brbrEach bedroom and the living room are equipped with brand new HIDEF Samsung 4K Smart TV’s. In addition, we have recently upgraded the cottage to include FREE 300 Mbps ATT Hi Speed Business Internet, new orthopedic mattresses, and cozy linens – towels to make your stay relaxed and pleasant. There is also a brand new Central Air Conditioning system to help keep you comfortable and snug, especially during the warmer summer months!brbrAdjacent is a completely equipped kitchen that has granite counter tops, glass cooktop stove, microwave and refrigerator. Even wine and champagne glasses are included! A bicycle lock-up in the courtyard is available.brbrBlocks from the marina district, and an easy walk (.7 miles) to Ft. Zachary Taylor where Australian Pines tower over the beach. There is on street parking available (Hemmingway House .28 miles, Duval Street 1 block, Marina District 7 blocks, beach .7 miles).brbrThere is a health food store located directly across the street called 'The Sugar Apple' which serves fresh fruit smoothies, lunch, and offers a variety of health food. A CVS is located one block away. A bike and scooter rental location is one block away. brbrA 3-night minimum stay required and strict No Smoking policy applies. Please contact owner for exception to 3 night minimumbrbrPlease note rates are subject to change and are higher during Event Periods such as Fantasy Fest, Gay Pride, Memorial Day, Christmas Week, New Year's Week, Thanksgiving, etc. Longer stays than 3 days may be required during event periods.brbrNOTE: There is No Dedicated Parking included with this rental. Directly on Simonton Street are (4) spaces and available on first come basis. We do recommend keeping the car parked and walk, bike or use the bus service, The Duval Loop. The Duval Loop provides FREE Hop on, Hop off bus service, operates every day, and stops a half block from the cottage. https://www.cityofkeywest-fl.gov/326/Duval-LoopbrbrIMPORTANT: We strongly recommend purchasing travel insurance to protect against illness, medical emergencies, weather-related issues, or other unexpected circumstances. While travel insurance can be purchased during the booking process, you may want to consider other reputable travel insurance providers, such as Travel Guard (AIG), Nationwide, Allianz, Berkshire Hathaway and Red Sky. We encourage you to review their coverage options and rates to find the best fit for your needs.brbrFor those traveling during Florida's hurricane season (June 1 – November 30), travel insurance is especially important. Please note that NO refunds will be issued for weather-related disruptions or early departures.

Cottage

The Dancing Rooster: 2 Blocks from Duval in Old Town.

Key West, Florida, United States

Bed

Bath

Sleeps

$430.76

**NEW LISTING** As soon as you arrive to this newly renovated, new town home you will be impressed at every turn. Privacy, a gorgeous backyard, and a one and only custom Key West pool design that will WOW you. Enjoy all of the five star amenities, including four complimentary beach cruiser bikes, with lights, baskets, and locks.brbrTHE LIVING AREAbrbrWith all brand new furniture, and 65 smart TV, you will have plenty room for entertaining. Poseidon's Paradise is loaded with high-end finishes, and elevated ceilings allowing for lots of natural light.brbrThe open living area leads you into the fully equipped chefs kitchen. With top of the line appliances, laminate countertops, a Keurig as well as a regular coffee maker, you will find all the pleasantries you have at home. Cook 5 star meals, grill your fresh catch on our new Webber grill, and entertain family/friends during your spectacular vacation.brbrTHE BACKYARD & POOLbrbrStepping outside through the set of French doors , you will be mesmerized by your very own private resort-like oasis, starting with the huge comfortable outdoor couch and sitting area. Relax and enjoy a movie or the big game on your new 65 outdoor smart TV. The custom pool is what sets Poseidon's Paradise apart from the rest. Whether you want to hang out along the long bench seating, relax in one of the two in water pool loungers, or swim laps for exercise in one of the largest residential pools in Key West, this pool offers it all. On the other side of you full outdoor bath, you will find an excellent place to enjoy outdoor dining from our six top dining table. Listen to the water coming from the waterfall and enjoy the custom LED lighting as you sit back and enjoy the vacation of your dreams.brbrACCOMMODATIONSbrbr- Bedroom One: Master King bed with luxury linens; 55 smart TV, en-suite bath with shower/tub, and vanity.br- Bedroom Two: Junior master - King bed with luxury linens, 55 smart TV, with French doors leading to backyard and pool areabr- Bedroom Three: Twin beds (can be converted into a King) and a 32 smart TVbr- Bedroom Four: Junior pool - Queen bed with luxury linens, 55 smart TV, with French doors leading to backyard and pool area.br****Poseidon's Paradise is all one level, and has up to 3 King beds!brbrADDITIONAL AMENITIES:brbr- Highest Wifi speed internet in Key Westbr- Washer and Dryerbr- Iron/ironing board and hand steamerbr- Central ACbr- Indoor and Outdoor ceiling fansbr- Linens and towels, including pool towelsbr- Weber propane BBQ grillbr- Private, fully fenced and tropical landscaped yardbr- Plenty of off street parkingbr- Pool heater (additional cost)

**Welcome To Poseidon's Paradise** Midtown Home & Incredible Pool *28 Nights Min

Key West, Florida, United States

Bed

Bath

Sleeps

$565.97

City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Poseidon's Paradise, your ultimate luxurious waterfront escape in Key West! brbr brbrNestled on the picturesque Riviera Canal, this retreat offers seamless access to the Gulf of Mexico and the Atlantic Ocean. As you step through the gate, you'll discover a haven designed for larger extended families or groups, perfectly suited for embracing the quintessential Key West lifestyle. Recently updated with a modern coastal chic aesthetic, the interior features sleek granite countertops and stainless steel appliances in the fully equipped gourmet kitchen. This property boasts the latest in technology, with fully automated landscape irrigation and lighting. You'll find ample parking for your convenience, ensuring an stress-free arrival and departure. The true jewel of Poseidon's Paradise is the heated concrete pool, which takes center stage in the backyard, overlooking the serene canal. Keep your eyes peeled for the frequent visits from friendly manatee families, who often grace the waters with their presence. Across the canal, a lush green mangrove provides a natural privacy screen, allowing you to relax in your own tropical oasis. For a closer encounter with Key West's incredible wildlife, embark on a paddleboarding adventure along the canal and through the enchanting mangroves. At Poseidon's Paradise, you'll discover the perfect blend of luxury, nature, and modern comfort, all coming together to create an unforgettable Key West experience. brbr brbrSLEEPS MAXIMUM OF 10 GUESTS: brbr brbrBedroom 1 (Main House, 2nd Floor): King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2 (Main House, 1st Floor): Queen Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3 (Guest House,1st Floor): King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 4 (Guest House, 2nd Floor): King Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 5 (Guest House, 2nd Floor): King Bed, Smart TV (no cable/satellite TV) brbr brbrLiving Room: Loveseat with Pull Out Queen Bed, Two Sofas, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 85' Private Dockage (bridge clearance ~12' at high tide) brbr brbr- Private Heated Saltwater Pool (heated to ~85 degrees Nov-Apr, small separate dip pool is not a hot tub) brbr brbr- Gazebo with Outdoor Dining Set brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Propane Fire Pit brbr brbr- Keurig, Toaster, Blender brbr brbr- Linen's and towels provided brbr brbr- 2.1 miles to Smathers Beach brbr brbr- 3.4 miles to Duval Street brbr brbr- 3.4 miles to Southernmost Point brbr brbr- 3.7 miles to Key West Historic Seaport brbr brbr- 4.2 miles to Mallory Square Sunset Pier brbr brbr- 4.4 miles to Fort Zachary Taylor State Park Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrBoating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, five exterior security cameras monitor the property. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oasis and Private Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$1550.05

PLEASE NOTE THAT THE MARINA NEXT DOOR IS CURRENTLY UNDER CONSTRUCTION SO THERE IS THE POSSIBILITY Of NOISE DURING THE DAY.brbrRECENTLY REMODELED/REFURNISHED, OLD KEY WEST ELEGANCE WITH AN ELEVATOR, PRIVATE POOL AND BOAT DOCKAGE...brIndulge in island chic as you approach this luxurious waterfront conch style home, located on the edge of Old Town overlooking Garrison Bite Marina. Breathtaking marina views from double balconies will lure you closer to this nautical gem while design and functionality merge to offer you historical charm with all the luxuries of a modern retreat. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES...brEnjoy a private entrance to this tropical retreat and head up the stairs to the first level that greets you with an expansive kitchen, offering every cooking tool your inner chef could desire for dreaming up culinary delights. A breakfast nook table, kitchen counter seating and the adjacent dining area provide multiple seating options for your loved ones to gather in and unwind. The open concept living area boasts panoramic sliding glass doors that overlook Garrison Bight Marina, surrounding you in the tropical allure of your southernmost getaway. Take advantage of the elevator carrying you to each story of the home. A full size washer and dryer closet is offered for your convenience. The main television is 85 inches. Enjoy live streaming on Youtube TV for binge watching your favorite shows. brbrSLEEPING ARRANGEMENTS...brThe first level of the home offers a king bedroom with a double entry shower bathroom. On the second level are two king suites with en suite bathrooms (one with a shower/bath combo and the other with a deep jetted tub and separate walk-in shower). Each suite has its own balcony and walk-in closet. The third level offers a full bath with tub/shower combo shared by a private king bedroom with closet and an open loft with 4 twin beds. All bedrooms offer TVs for your late night entertainment.brbrOUTDOOR LIVING...brThis is a boater's dream home consisting of a private dockage (can fit a boat up to 30 ft long) and deep water access! Luxuriate around your private pool (that is heated during the cooler months) and watch the fishing fleets return with their fresh catch!brbrPARKING...brThere are 2 parking spots in the driveway.br***Boat trailers may NOT be parked on the property. You can make arrangements with nearby marinas for trailer parking. Garrison Bight Marina is right next door, or the City Marina @ Garrison Bight is just 1/2 mile away!brbrPETS...brThis home allows 1 dog only and a pet fee is required. Please include the size/breed when inquiring. 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.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!brbrENDLESS TROPICAL THERAPY...

SEVENTH HEAVEN~Waterfront 5 BR, 4 Ba Townhome with Pool, Elevator & Dockage!

Key West, Florida, United States

Bed

Bath

Sleeps

$2140.13

Summary:brbrLocated right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's Duet offers a central location to Key West’s main attractions and everything else the Southernmost city has to offer. With a balconies overlooking Duval Street you can be as much connected to or above the action as your whim desires.brbrThis family-friendly combo is great for sleeping a large group of up to 18 guests!brbrbrbrThe Space:brbrFully equipped with a kitchen, living room, dining area and balcony overlooking Duval Street, these lofts feature everything you need. The kitchen is contains a stove, refrigerator, dishwasher and Keurig coffee machine. brbrbrbrThe sleeping arrangements consist of the following: brbrLoft 1: First floor bedroom with a king size bed, an upstairs loft with two king size beds and a pull out couch in the living room. brbrbrbrLoft 2: First floor bedroom with a king size bed, an upstairs loft with two king size beds and two pull out couches in the living room. brbrbrbrThere is 1 full bathroom in each unit located in the hallway on the first floor.brbrbrbrBook Duval's Duet 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:brbrOn the 500 block of Duval, Duval's Duet is centralized to everything Key West. brbrIn the heart of Duval street you can find many of locals favorite's such as: Fausto's Food Market, Keys Coffee Co., and Cuban Coffee Queen, and tourist attractions such as: The Ernest Hemingway house, Mallory Square and Key West Lighthouse, all walking distance from your front door! brbrLooking for a night out, find Willy T's, Fogarty's and Fat Tuesday's within 1 block of these units.brbrBeing in the heart of everything does come with noise of Duval street, but nonetheless an easy and convenient location to experience all Key West has to offer!brbrbrbrGetting Around:brbrThere are a variety of great ways to explore Key West including by bicycle, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrUnfortunately, there is no on-site parking for this unit.brbrFor overnight parking here are some parking lots:brbr• Fleming Street Pay-to-Park Lot (This is Closest to you!)brbr• 204 Simonton Streetbrbr• Caroline Street Outdoor Parking Lotbrbr• Park N Ride Old Town GaragebrbrStreet 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:brbr- This property consists of 2 historic lofts and can only be accessed by a flight of stairs. There is no elevator available.brbr- No pets allowedbrbr- No parking is provided: we are happy to provide you with nearby recommendations!brbr- This listing is 2 units next to each otherbrbrbrbrBoth Lofts also Include:brbr-Stackable Washer & Dryer brbr-A/Cbrbr-Ceiling Fansbrbr-Flat Screen TV’s in Living Room & Bedroomsbrbr-Fully Equipped Kitchen brbr-Starter Supply of Paper & Cleaning Productsbrbr-Linens and Towels Providedbrbr-Free Wireless High Speed Internet

Apartment

Duval's Duet - Double Balconies Duval Street

Key West, Florida, United States

Bed

Bath

Sleeps

$1372.2

Summary:brbrLuxury 2BD/ 2BA Suite with Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Porch with Amazing ViewsbrbrbrbrThe Space:brbrEscape the Ordinary....brbrbrbrThe Carysfort Lighthouse Suite is a luxury 2 BD/ 2BA stand-alone house located directly in front of one of our two brand new oasis pools with direct access to the pool deck and brand-new property amenities that sleeps up to 6 guests. Completely renovated in 2024, the suite is our premier unit and offers breathtaking pool views through the rear glass folding doors with Key West Lighthouse and partial Duval Street views from the private front porch located on a quiet Key West Lane. The suite also comes with an exclusive off-street parking spot for your stay.brbrbrbrSuite Amenities:brbrbrbr• Luxury king master bedroom with premium linensbrbr• Luxury queen bedroom with premium linensbrbr• Queen sleeper sofabrbr• Fully equipped brand new kitchen with bar seatingbrbr• Spa quality glass master en-suite bathroombrbr• Second bathroom with showerbrbr• Hardwood flooring throughout the suitebrbr• Spacious front porch with lighthouse and partial Duval St. viewsbrbr• Smart TVs with the latest Roku device for apps and streamingbrbr• High-speed Fiber Wi-Fibrbr• Washer and dryerbrbr• Luxury well-appointed furnishing and artworkbrbr• Reserved and exclusive off-street parking space for one vehiclebrbr• Accordian door access to one of the property's two oasis pools directly behind the unitbrbr• Our largest suite at more than 800 square feetbrbr• Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Carysfort Reef Lighthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind. This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr• Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr• Brand-new spacious pool decks around each poolbrbr• Six luxury teak chaise loungers with umbrellas and pillowsbrbr• Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr• Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr• A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr• Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr• Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr• Covered bar kiosk for enjoying a cocktailbrbr• Key West tropical foliage throughout the property with lighted step-stone pathsbrbr• Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr• Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3, two-bedroom suites, 2, one-bedroom suites, 1, one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr• The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr• The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr• The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr• Key West Lighthouse Museum, 2-minute walkbrbr• Ernest Hemingway Home and Museum, 2-minute walkbrbr• Blue Heaven Restaurant, 5-minute walkbrbr• Southernmost Point Buoy, 8-minute walkbrbr• Key West Butterfly Conservatory, 8-minute walkbrbr• Sloppy Joe’s Bar, 12-minute walkbrbr• Key West Amphitheater and Park, 12-minute walkbrbr• Mallory Square Sunset, 12-minute walkbrbr• Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!

Carysfort Reef Light Suite

Key West, Florida, United States

Bed

Bath

6

Sleeps

$570.25

A Stay You’ll Never ForgetbrbrWelcome aboard Dolce Vita, a beautifully refitted luxury motor yacht offering a one-of-a-kind stay in Key West. Perfect for couples, families, friends — and even your dog — this unique floating retreat combines waterfront charm with full resort access.brbrWake up to marina views, enjoy coffee on the aft deck, and walk just steps to the pool. In the evening, take the complimentary shuttle into downtown and return to your peaceful marina setting.brThe boat has been newly renovated, boasts a brand new AC system and the interior refitted to a high standard. there is a spacious saloon with a smart TV and then a few steps steps down into the galley dining area. The galley is equipped with an induction stove top, microwave oven ,coffee perculator, air fryer and fridge freezer.brThe master cabin has a walk around queen bed and on suite bathroom with shower and another smart TV, while the forward cabin has a cozy double berth with adjoining bathroom.brUp on the aft deck there is a dining table and 4 chairs for alfresco dining or just chilling with cocktails.

tUnique Waterfront Yacht in 5 star resort. Pools, Gym & Downtown Shuttle

Key West, Florida, United States

Bed

Bath

Sleeps

$240.12

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis property is a 28 night minimum. Boat slips available for rent! Inquire with us. brbrFEATURES:brBedrooms: 2 (1 king and 1 queen)brBathrooms: 2brLocation: Sunset Marina Gated CommunitybrSquare Feet: 1558brParking: 1 assigned covered parking space (NO ELECTRIC VEHICLES/SCOOTERS/BIKES ALLOWED)brAmenities: Wifi, TVs, in-unit laundry, balcony, shared pool, near the golf course, boat slip availablebrbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Condo

Hidden Paradise-2bed 2bath condo w/ ocean views, dock space, pool

Key West, Florida, United States

Bed

Bath

4

Sleeps

$186.8

Escape to Your Private Key West Cottage Retreat!brbrWelcome to your charming and secluded Key West cottage, a perfect haven for couples or solo travelers seeking a peaceful getaway! Nestled in the heart of Old Town, just blocks from the Southernmost Point, the Hemingway House, and the vibrant Duval Street, this hidden gem offers the ideal blend of tranquility and convenience.brbrThe Space: brStep inside your completely private oasis, featuring a cozy living area, a beautifully designed loft, a fully equipped kitchen, a modern bathroom, and inviting porches where you can unwind and soak up the island breeze. The sparkling pool is just steps from your front yard, providing a refreshing escape after a day of exploring.brbrGuest Access: brEnjoy easy access to both the front and side entrances of the Main Street, ensuring your entry and exit to this delightful retreat is a breeze. For those bringing bikes, there are designated bike parking areas at street posts or bike racks nearby.brbrImportant Notes: brPlease be advised that this is a smoke-free property, with no smoking permitted anywhere inside or outside the premises.brbrExperience the magic of Key West in your private cottage, perfect for a rejuvenating getaway. With a minimum stay of 28 days, you can truly immerse yourself in the island lifestyle. Book your slice of paradise today and make unforgettable memories in this serene cottage!

Cottage

One Bedroom Cottage House in Old Town Key West by the Hemingway House.

Key West, Florida, United States

1

Bed

1

Bath