33040, Florida, United States Vacation Rental Homes By Owner

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 360 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Street parking – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. extra charge of $50 per nightbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Hotel

Perfect for Groups! 2 Pet-friendly Units, Free Breakfast, Outdoor Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$524.33

28 NIGHT MIN STAY REQ. PLEASE DO NOT SUBMIT A BOOKING REQUEST FOR ANYTHING LESS. brLarge 3 Bedroom / 2 Bath private residence with in-ground pool and hot tub located directly on the Riviera Canal in beautiful Key West, FL. This upscale, newly renovated home is a boaters paradise that sleeps up to 10 guests and is DOG FRIENDLY! brbrLocation: This beautifully renovated vacation rental home is located in the highly desirable waterfront New Town neighborhood of Key West, FL. Just 1.8 miles from the world famous Duval Street, five minutes to the Key West Airport, Higgs Beach, and just minutes from Key West shopping, dining, and the infamous bars on Duval St. All of which can be easily reached using one of our complimentary on site bicycles, the city bus, ride-shares or your own personal/rental car.brbrAmenities:brWiFi - Basic Plus Cable TV & Smart TV- Ceiling fans- Air Conditioning- Front Load (he) Washer & Dryer- Linens- Bath Towels- Beach/Pool Towels- Complimentary Starter Supply of paper goods & basic household cleaning products. 2 outdoor security cameras. brbrOther Amenities & Free Guest Use of the following: brBicycles w/code locks/air pump. Kayak and Paddle board.brNote: We provide the above mentioned items free of charge for our guests to enjoy during their stay. If you elect to use any of our equipment we kindly request that you clean the equipment and secure it properly in place after each use that way it is ready for the following guests to enjoy as well. Any loose sporting goods/equipment should be cleaned,dried and securely stored away from the outside elements. Please be advised, due to unforeseen events and/or damage, the availability of the above mentioned items cannot be guaranteed. No refunds will be provided in the event that something listed above is not available during your stay. Guests are financially responsible for any damages or loss to/of these items. Please be sure to report any problems or damages with the outdoor equipment promptly. brbrAccommodations: brOpen concept floor plan with tile flooring throughout. The fully equipped state of the art kitchen includes an oversized center island w/seating for 5, top of the line stainless steel appliances, granite countertops and custom cabinetry. The luxurious kitchen opens up to a 6 person dining area and living room with a sectional sleeper sofa and large flat screen tv. The adjoining room includes a custom designed fully equipped bar with granite counter tops, a large flat screen tv, a sleeper sofa, stainless steel refrigerator, and luxurious gaming/card table all overlooking the waterfront swimming pool and Riviera canal.brbrBedrooms:brBedroom 1- Master Bedroom- One king size bed w/luxurious linens, a memory foam/down alternative combo mattress topper along with a custom closet and full size en suite bath w/shower. Sleeps 2 guests. brbrBedroom 2- Two full size beds, luxurious linens, and a custom closet. Sleeps 2-4 guests. brbrBedroom 3- One King size bed with luxurious linens, memory foam/down alternative combo mattress topper and custom closet. Sleeps 2 guests. brbrSpare Room 4- Sleeper Sofa Room- One queen size sleeper sofa w/ linens, and memory foam mattress topper. brNote: This room has outdoor/pool/waterfront access via 2 separate entry/exit doors and is therefore not suitable for small children. Doors have glass pane windows so this space not completely private. Sleeps 2 guests. brbrAdditional Beds- The living room sectional sofa and the regular bar sofa are both queen sleeper sofas with memory foam mattress toppers. br(Note: This home has a 10 guest maximum regardless of sleeping arrangements. Guests are counted per stay not at any given time throughout your stay)brbrBathrooms: brMaster Bath 1- Full size with shower, toilet and sink w/granite countertop. brbrShared Hall Bath 2- Full size with a shower/tub combo, toilet, and sink w/granite countertop.brbrOutdoors: brFront Yard- The front yard of this home has been transformed into a resort like hideaway with two oversized tiki huts, lush tropical foliage, soft faux grass and a luxurious seating area with comfortable high end couches and chairs. The large custom made restaurant style hibachi grill with surround seating for 8 is the perfect place to grill your steaks, seafood and fresh catch paired with fresh veggies purchased from the local weekly farmers market. (Grill should be fully cleaned after each use and prior to departure). The outdoor wood burning fire pit is surrounded by four heavy duty polywood Adirondack chairs perfect for late night chats and s’mores around the campfire. brbrBack Yard- Enjoy fishing and wildlife viewing right from the sea wall of the back yard. Take advantage of the three complimentary single person kayaks or two paddle boards and paddle yourself out to the mangrove trails and salt ponds just down the canal. Spend a lazy afternoon floating around the in-ground pool or basking in the warm Florida sunshine poolside. Spend those breezy tropical island nights soaking your cares away in the warm bubbly hot tub. brNote: Front & Back Yard are Fully Fenced w/ the Exception of the Seawall along the Backyard ledge. brbrBoat Access: 60’ Seawall w/private dockage for easy daily access to the water for fishing, boating, diving and island hoping. The public boat ramp is located directly across the canal. Bring your own boat or rent a boat from one of the nearby marinas. Seawall can accommodate one boat up to approximately 30’. Please Note: The Riviera canal leads to the Gulf of Mexico and the Atlantic Ocean but the bridge at the end of the canal has a max clearance height of approximately 9’ at high tide. There is also a floating dock with ladder along the sea wall for easy access to launch the kayaks and paddle boards. brbrParking: There is off street parking for up to 3 cars directly in front of the home. Additional parking is available street side across the street in front of the mangroves. Trailers are subject to city rules and restrictions and will be ticketed if left unattended street side. brbrPet Rules & Restrictions: we allow up to 2 pets (Dogs Only) with a $100 non refundable pet fee per 2 dogs. Dogs must be under 50lbs each. Please inquire with any questions regarding these weight restrictions. You must include pets in your booking request and provide me with the details via message. brATTN: Most of the front yard is faux grass and PETS ARE STRICTLY PROHIBITED from using the bathroom there. Dogs MUST be supervised at all times in this area. Failure to comply will result in you being charged an additional $350+ professional cleaning fee and/or the the current cost to replace and install new faux grass if necessary. Pets may use the bathroom on the rocky area under the 2nd tiki hut or anywhere out front street side while leashed. You must promptly clean up after your pets in either of these areas. Pets may not be left unattended outside the home. You are responsible for any damages caused by your pets during your stay. brNOTE: Please include pets in your reservation request and send the following information in the comments section of your request/inquiry: Number of dogs, breeds, sizes and age. brbrSmoking: This is a Non-Smoking Property. As a result, any damages, debris, cigarette butts or trash left behind will result in additional cleaning fees being charged. Any cigarette burns or damages inside or out will be deducted from the security/damage deposit. If we find that you or anyone in your party has smoked inside the home a $250 fee will automatically be deducted from the security/damage deposit along with any other cleaning fees that may be incurred. brbrThings to Do/ Nearby Activities: Mallory Square, Smathers Beach, Duval Street, Skate Park, Kayaking, Paddle-boarding, Diving/Reef Diving, Snorkel Trip, Sunset Sails, Adventure Cruises, Dining, Nightlife, Live Music and more….brbrATTN: 28 NIGHT MINIMUM REQUIRED. brThis rental has a 28 night minimum requirement.brAll 28 nights must be during the same month. brExample: brCheck in: March 1st brCheck out: March 29th, 30th, 31st. brAll reservations must begin on the 1st day of each month & end after the 29th or the last day of that same month. (No 1/2 month to 1/2 of the next month rental periods and no rollovers into the following month) Please inquire with any questions regarding this policy as we may be able to accommodate certain requests. brbrPlease Note: The person making the reservation must be present on property for the entire duration of the stay. You may not book this home for another person or party. If you plan to share or split this rental with other people you must provide me with the details and get pre approval to do so prior to booking. 10 guests means a total of 10 people for the duration of your stay not 10 new guests every week or other week. All guests must be registered guests and pre approved to be on property prior to making your reservation not afterwards. There are two security cameras located on property and are outdoors only. They are located at the corner of the roof of the home in the front and back yard. These are for security purposes and to prevent damages or loss to our property. Please be advised, all payments are due in full at the time of booking and we do not offer payment plans of any kind. However, VRBO recently started working with another 3rd party company to offer payment plans for guests in need of this service. Please contact VRBO directly for further details. All rental rules are considered to be accepted by you once your booking request has been submitting and approved. Upon completion of your reservation you agree that you have read these terms and conditions and agree to abide by all rules of the home during the booking timeframe.

Waterfront Key West Home with Pool-Hot Tub on Riveria canal! 28 NIGHT MIN STAY.

Key West, Florida, United States

Bed

Bath

Sleeps

$168.22

AN ESCAPE LIKE NO OTHER…brDisconnect from the real world and reconnect with each other in this picture perfect, quaint cottage tucked away on a quiet and vibrant lane of Old Town. Your Paradise awaits just beyond a lovely white picket fence inviting you into a lush and luxuriant setting to call your island home.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrAMENITIES AND FURNISHINGS...brA private, covered front porch beckons your lighthearted chit chat as you take in your tropical surroundings with your morning coffee in hand. Slip inside to a fully renovated and bright Great Room with cool hardwood flooring, cathedral ceilings and breathtaking natural lighting. Plush furnishings surround a flat screen TV, allowing you to sink in for your binging pleasure. A fully equipped kitchen with a stylish blue backsplash will calm your senses as you whip up your favorite dish and craft up your cocktail at the enticing bar area with bar seating for 3. Bring the outdoors in as you perch the sliding doors open for the best of both worlds!br brSLEEPING ARRANGEMENTS...brFind your sleeping sanctuary just off the Great Room with a cozy queen bed with sumptuous linens for a peaceful night’s rest. An en suite full bathroom features a stunning walk-in glass shower with beautiful blue tiling within this nautical dwelling. A sofa sleeper resides in the living area for additional sleeping arrangements. br brOUTDOOR LIVING...brBring your fresh cooked cuisine outdoors on a private back deck enveloped in abundant, vibrant foliage with a sweet breeze by your side. A gas grill is provided to grill up your fresh catch of the day. Bike or stroll through this quaint neighborhood of beautiful, historic homes and enjoy just a short ride into town to all that Key West has to offer. brbrPETS...brThis home is not pet-friendly.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)br brPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.br brBOOKING DATES...brThis home is available only as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.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).br brSTART LIVING ON ISLAND TIME…

GILLEY'S PLACE ~ Fully Renovated 1 Bedroom, 1 Bath Cottage in Old Town!

Key West, Florida, United States

Bed

Bath

Sleeps

$275.22

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrYou have many choices when choosing where to stay in Key West, but the most unique way to get an authentic Key West experience is by spending your vacation in a classic conch cottage smack dab in the heart of Old Town. You know what they say - “In a world full of apples, be a pineapple.” Whether you’re on a writer’s retreat or simply need an escape from reality, THE POETIC PINEAPPLE lets you experience all the inspiration Key West has to offer. Located on a quiet lane, this freshly renovated home provides a peaceful place to relax, recenter, and recharge. Best of all, your stay at THE POETIC PINEAPPLE includes Last Key Realty’s 5-Star Guest Services, known for providing memorable Key West vacations. There are a lot of apples out there, choose to be a pineapple.brbrTHE LOCATION…brbrImagine your vacation home being just a few steps from all the shops, restaurants, and attractions of Duval Street and the Historic Seaport. Half a block away are local favorites like Mangoes, DJ’s Clam Shack, and Kaya Island Eats. Just a half block in the other direction, you’ll find yourself at The Green Parrot. You'll also be an easy walk or bike ride to the best beaches and sunset views at Fort Zachary Taylor State Park and the newly constructed Truman Waterfront Park. On-street parking can be found on Aronovitz Lane, but it is first come.brbrTHE LIVING AREA & KITCHEN… brbrDesigned in Key West’s famous “conch cottage” style, this cozy island home welcomes you with stylish furnishings and décor that exudes that familiar feeling of home from the moment you enter. The living area boasts a large flat screen TV and there is plenty of comfortable furniture for your entire group to enjoy. The kitchen is fully equipped with every appliance and tool needed to prepare a meal at home when you decide to take a break from the many restaurant options within walking distance. The kitchen bar seating is perfect for a casual bite or for keeping the cooks company, and the indoor dining table is great for more formal meals.brbrTHE OUTDOOR LIVING…brbrFully fenced for privacy and surrounded by lush tropical greenery, the outdoor living space of this home will undoubtedly be a favorite gathering place for your group and is complete with a large propane grill and outdoor dining set. The front porch has a three piece bistro set and is an awesome place to sip your morning coffee or evening cocktail while watching the world go by on this discrete Old Town lane.brbrTHE ACCOMMODATIONS… brbr** Master Bedroom: Queen bed, flat screen TV, large closet, direct access to the front porch, and an en-suite bathroom with a walk-in shower.brbr** Second Bedroom: King bed, flat screen TV, closet, and easy access to the fully renovated hall bathroom with a shower and tub combo. brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room and All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced and Landscaped Private Yard br** Propane BBQ GrillbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 4 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per pet

**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR/2BA Cottage + LAST KEY SERVICES

Key West, Florida, United States

Bed

Bath

4

Sleeps

$998.68

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThe moment you arrive at CASA AMARILLA and see the dual rocking chairs beckoning you to the front porch, you’ll feel the weight of the world start to lift from your shoulders as your vacation truly begins. Upon entering this adorable cottage, you’ll see the quaint interior is the perfect place to unwind, offering cozy bedrooms, a fully stocked kitchen, and a wonderful private pool out back. Best of all, CASA AMARILLA is located on the Southern end of Old Town just half a block from Duval Street. Your stay also includes Last Key Realty's Five-Star Guest Services, known for providing memorable Key West vacation experiences.brbrTHE LOCATION...brbrLocated a half block off of Duval Street, CASA AMARILLA is an Old Town dream: you can walk to Duval St, you’re only a few blocks from the Southernmost Point, Fort Zachary Taylor State Park, or any other Old Town attraction you may want to explore. You'll be a short walk or bike ride to all that Old Town Key West has to offer. The best part is you’re on the “quiet” end of Duval St, which means you can easily head down to the fun, but you don’t have to worry about it keeping you up at night. While you won’t need a vehicle from this prime location, the private driveway serves as your off-street parking space in case you decide to rent a car or golf cart.brbrTHE LIVING AREA & KITCHEN…brbrCASA AMARILLA has a comfortable living area featuring a large flat screen TV and double French doors that open right up to the tranquil private pool area. The fully-equipped kitchen includes all of the comforts of home, with plenty of counter and cabinet space. There is a six-person high-top dining table located just off the kitchen, so everyone can sit down and enjoy a meal together.brbrTHE POOL...brbrOut the back doors is your fully fenced private back yard with a heat optional dip pool. Beside the pool are chaise lounges so you can soak up some sunshine. There’s also an outdoor shower for rinsing off after a day at the beach or a dip in the pool. On the pool deck sits a large propane BBQ grill, ready to cook up the day’s fresh catch, and an outdoor dining set with seating up to four.brbrTHE ACCOMMODATIONS...brbrEvery bedroom in this lovely home is located on the first floor. No stairs necessary!brbr** Master Bedroom: King bed, large flat screen TV, and en suite bathroom with a walk-in shower. Pocket doors separate this bedroom from Bedroom #2.brbr** Second Bedroom: Queen bed, flat screen TV, armoire, French Doors to the pool area, and access to the shared bathroom off the living room. Pocket doors separate this bedroom from the Master Bedroom.brbr** Third Bedroom: Two Twin beds OR One King bed, flat screen TV, and access to the shared bathroom off the living room.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** 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** Fully Fenced & Lushly Landscaped Private Yardbr** Private Heated Poolbr** Propane BBQ Grillbr** Off-Street Parking for 1 VehiclebrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per pet

**CASA AMARILLA @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES

Key West, Florida, United States

Bed

Bath

Sleeps

$311.49

If you have high expectations, you are going to enjoy staying at High Tide. You are within walking distance to restaurants, nightlife, the pool (just 100 feet away) and with your own private parking. High Tide includes wireless internet, an outdoor grill, outdoor furniture on the two balconies, front porch and back deck. brbrThe living room has 2 sets of French doors opening to a back deck, TV, DVD player, Bose Mini Blue Tooth speaker, scanner, printer and 2 ceiling fans.brbrThe Master bedroom has a king size bed with a 50’” screen TV, second bedroom has a queen size bed with a TV. Both bedrooms have French doors opening to balconies, 500 plus count sheets, alarm clocks with USB connections and ceiling fans.brbrThe upstairs bathroom has a bathtub with shower, a full-size washer and dryer, plush towels and beach towels. The half bath is downstairs.brbrThe kitchen has full size appliances and is equipped with an electric blender, mixer and can opener. There are enough dishes, utensils, pots and pans to bake or prepare a meal. There is a dining table with a marble top.brbrYour expectations will be met at High Tide.brbrPlease note: This property has a 28 night minimum stay

High Tide at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$557.48

29 NIGHT MINIMUM RENTAL ... This property is not allowed to accept pets.brbrEnjoy endless views of the tranquil waters of the Atlantic Ocean while staying in this updated luxury condo. This oceanfront oasis is located in the Key West Beach Club, an upscale, gated community with two oceanfront pools, pavilion area, workout room and tennis court. The Key West Beach Club is one of the very few condo communities on the island that sits directly on the coastline.brbrThe expansive living room with its vaulted ceiling is tastefully decorated and comfortably furnished with breathtaking views of the Atlantic Ocean that can be seen immediately upon entry. The quite large kitchen features stainless appliances and beautiful light fixtures to brighten up the brewing of your morning coffee and preparing any meals should one so desire.brbrThe open dining and living areas and the expansive balcony offer wonderful options to enjoy that morning Café con leche or dining indoors or al fresco. The condo's first floor also contains the Primary Bedroom with ensuite and balcony access. In addition to the outdoor dining table, the balcony also offers an ample seating area for lounging and conversations.brbrThe second bedroom is also on the first floor as you enter the condo. It has a large ensuite bathroom that also offers access from the hallway.brbrA spiral staircase leads to the second floor of this two story unit. Upstairs offers an open loft style family room entertainment area with flat screen television. The third private bedroom and ensuite bathroom are just off the loft family room.brbrBedroomsbrPrimary Bedroom: King bed, flat screen TV, direct access to the balcony, ensuite bathroom with tiled, walk-in shower.brbrFront Bedroom: King Bed, ensuite bathroom with tiled, walk,-in shower which also does allow for hallway access. brbrLoft Bedroom Suite: Queen Bed, sofa sleeper, flat screen TV and ensuite bathroom with walk-in shower.brbrUnit Features:brCentral A/C, Wi-Fi, washer/dryer, security entry, garage parking and elevator access.brbrCommunity Amenities: Resort-type amenities include two oceanside pools (heated), tennis court, outside cooking facilities and pavilion, fitness center and sauna. Since the shoreline is natural, beach access is best at the public beaches on either side of the community. Smather’s Beach is around the corner to the right when exiting the property and Higgs Beach is just past White Street Pier to the left. There are plenty chaise lounges around the pool areas as well as the covered pavilion to enjoy during those sunny island afternoons.brbrAdditional things to know:brThe Key West Beach Club Condo Association requires additional registration, which includes providing copies of photo IDs for everyone over the age of 17, in advance of your arrival. Details will be provided along with your RKWV rental agreement.brbr*Disclaimer: Due to the property's oceanfront location, please be aware that Key West experiences seasonal occurrences of fermenting turtle grass along the south shore of the island brought on by our southern winds in the late spring and summer. This is a natural phenomenon that is outside of our control.brbrPlease note: This is a Monthly vacation rental with a minimum stay of 30 days, excluding February. The condo association requires completion of a registration form as a condition of this rental.

Oceanfront Splendor @ the Key West Beach Club

Key West, Florida, United States

Bed

Bath

Sleeps

$253.13

There's a lot to love about #1 at the Foundry! It's nestled within Key's West world-famous Truman Annex where you'll find charming streets, white picket fences and tropical landscaping. You'll love that we're close to the beach and many attractions, yet in a peaceful part of town. Our location can't be beat! It's just a few blocks from the action of Duval St and a quick bike ride or walk to beaches at Ft Zachary Taylor. The Southernmost Point, Key West Amphitheater and Mallory Square are all within walking distance. brbrBeing an end-unit, #1 at the Foundry has a few *bonus features* you'll enjoy. The first bonus is an additional wall of expansive windows and an extra French door. The result is an abundance of natural light and views of tropical landscaping. The second bonus is that this unit has TWO lovely, tropically landscaped gated courtyards. The first is on charming Front St, inside a pretty iron gate. The second is even larger and is on the Eaton St side. It's accessed through the extra French door which is in the kitchen, making it very easy to move food and drinks outdoors. The side yard is especially beautiful in the late afternoon and makes a great place to hang out or have dinner. There's a private gate to Eaton St and it is just steps away from your designated parking spot. It's unusual within the Foundry to have two yards and all the extra windows. We love the additional space and all the extra light. We think you will love it too.brbr#1 at the Foundry is a three story home. On the first floor, you'll find the spacious living, kitchen, and dining areas, along with a half bath. High ceilings make the space feel even larger. Up the stairs, you find the primary bedroom which has a king sized bed and French doors leading to a patio that overlooks peaceful Front St. There is an en suite bath and laundry on this floor. The top floor is home to another private bedroom with a queen sized bed and en suite bath. Each bedroom has a TV.brbrThe historic red brick Foundry structure was built in the 1800's as a part of an annex to Naval Station Key West. The historic building was re-imagined in the 1990's as townhome residences in what is now known as the upscale residential neighborhood of 'Truman Annex'. This charming island neighborhood was named for President Harry Truman who spent his winters in at the Annex in his home known as 'The Little White House.' His famous residence, which is now a museum, is just down the street from the Foundry.brbrA heated pool, shared only by those staying at the Foundry, is just moments away. Within this gated area, you'll find abundant lounge chairs and a restroom in a resort-style setting.brbrEach unit has one reserved parking space. The space for #1 is very close by. When coming in from the car, it's particularly convenient to enter the home through the private side yard and then into the side kitchen door. You may not even use a car while you are staying with us - so much is within walking distance!brbrbrPETS: not pet friendlybrbrSMOKING: Smoking is not allowed in the home, on the decks/yards, by the pool or anywhere at all in the community.brbrWe ask that you please do not store bait in our freezer or refrigerator. Damage charges will apply.brbrPlease note: There is central AC but no heat in this home.

Truman Annex end-unit home, private outdoor spaces, pool, close to Duval & beach

Key West, Florida, United States

Bed

Bath

Sleeps

$570.73

WHEN ONLY THE BEST WILL DO...brLocated in the Casa Marina Area of Key West known for spacious and elegant fine homes; the Garden Oasis is no exception. A beautifully constructed single level home recently renovated and designer decorated with a warm and soothing palate, furnishings that boast both style and function and fabulous covered wraparound front porch and rear lanai that afford you several vignettes to lounge, read, relax or entertain.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrSLEEPING ARRANGEMENTS...brThis four bedroom home has a grand master suite with king size bed and luxurious en-suite bath complete with custom cabinetry, soaking tub and shower finished in fine marble. Two additional queen bedrooms share a private bath plus an additional half bath for visiting guests. The fourth bedroom is a comfy king situated poolside in a spacious detached guest house with en-suite bath. Fine linens and bedding throughout provide a luxurious nights sleep for all.brbrDETAILS AND AMENITIES...brWell appointed open floor plan with great room featuring vaulted ceilings and 3 sets of sliding glass doors that lead to over-sized wrap porch over looking pool area and perfectly manicured tropical grounds. Custom kitchen featuring rich solid wood cabinetry, granite counters, fine stainless appliances, breakfast bar and wine refrigerator. Elegant travertine flooring throughout perfect for the indoor/outdoor living this property lends itself to.brbrPOOL AND OUTDOOR LIVING...brThis fine property boasts over 10,000 sq.ft. of tropical grounds ideal for those seeking ultimate privacy. Unwind in the heated pool surrounded by a sunny patio perfect for soaking up the rays. If a retreat from the sun is what you desire relax under the cool canopy of mature trees or on the over-sized wrap porches that flank the front and rear of the home perfectly appointed with comfortable outdoor furniture for lounging and dining.brbrPETS...brThis is a pet-friendly home and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrA TRULY PRIVATE TROPICAL OASIS AWAITING YOUR ARRIVAL!

GARDEN OASIS ~ Great Casa Marina Location with True Island Elegance!

Key West, Florida, United States

Bed

Bath

Sleeps

$534.38

This is a great OCEANFRONT unit with large balcony to watch sunsets. Hyatt Sunset Harbor is perfectly located in downtown Key West next to Mallory Square and the Mel Fisher Museum. Walk along the boardwalk, shop in the local stores, or head to Duval Street only a couple blocks away. The resort has pool, hot tub, and grills for use during your stay.brbrHyatt Sunset Harbor is a 40 unit Hyatt Residence Club Resort. There are laundry facilities on site free of charge. There are NO daily resort fees, but parking is extra.brbrEach unit has a King sized bed in master and a Queen sized bed in second bedroom. In addition, there is a pull out couch in the living room. Max occupancy 6 guests.brbrCheck-ins and Check-outs are Sunday to Sunday.

DOWNTOWN KEY WEST 2BED OCEANFRONT!

Key West, Florida, United States

Bed

Bath

Sleeps

$9,588

Summary:brbrEscape to paradise with this stunning 6-bedroom, 6.5 bathroom home nestled in the heart of historic Key West. Walking distance to everything, this home is ideal for families or large groups, this spacious retreat offers the perfect blend of modern amenities and tropical charm.brbrbrbrEnjoy your own oasis with a sparkling private pool, surrounded by ample lounging space. Perfect for refreshing dips under the sun or evening cocktails under the stars.brbrbrbrThe Space:brbrStylishly designed interiors feature a spacious living area, fully equipped kitchen with stainless steel appliances, and dining spaces ideal for hosting memorable meals with loved ones. Each bedroom is thoughtfully appointed with plush bedding and ample storage, ensuring a restful stay for up to 12 guests. brbrbrbrThe sleeping arrangements are as follows:brbrBedroom 1: King Bed brbrBedroom 2: King BedbrbrBedroom 3: King Bed brbrBedroom 4: King Bed brbrBedroom 5: Queen BedbrbrBedroom 6: King BedbrbrbrbrGuest Access:brbrOur self check-in makes the process seamless. brbrbrbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrbrbrThe Neighborhood:brbrLocated in downtown Key West, you're just steps away from world-class dining, vibrant nightlife, and iconic attractions like Mallory Square and Duval Street. From water sports and beach days to exploring historic landmarks and local art galleries, Key West offers endless opportunities for adventure and relaxation.brbrbrbrGetting Around:brbrParking for 2 vehicles in the driveway and a corresponding space in front of the driveway on the street, both of which are reserved for this property. Any additional street parking is first come first serve and can be difficult to find.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi or by feet. This unit is located in downtown Key West and many attractions are within walking distance. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr-There is an electric vehicle charger at the property that is card-operated.

The Rigby House - Pool, One block from Duval St

Key West, Florida, United States

6

Bed

6

Bath

12

Sleeps

$293.49

Beacon Terrace in the Truman Annex is a beautifully renovated town home in the historic Foundry in the Truman Annex. brThe living area is the entire first floor and has an open plan, with 11-foot ceilings, double French doors, and plenty of natural light. brEnjoy the large outdoor deck with plenty of room for lounging, dining and relaxing!brThe recently updated kitchen has top-of-the-line appliances, with granite counter tops and all the tools needed to prepare a delicious meal from home. The Primary Suite located on the second floor includes a King bed, a flat screen TV, a private balcony, and an elegant en-suite bathroom with a walk-in shower. The Second Bedroom located on the Third Floor features Two Twins OR One King bed, a flat screen TV, and an en-suite bathroom with a walk-in shower. Also there is a Washer & Dryer, Central Heat and A/C, Ceiling Fans, Wi-Fi internet access, & full cable included. Assigned off street parking for one car and access to a refreshing community pool.brbrPlease note: This property has a 28 night minimum stay

Beacon Terrace at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$2223.86

The Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. These two beautifully renovated historic structures provide 10 bedrooms and 7.5 bathrooms. This is a remarkable place for family and friends to stay together in a Key West weekly rental. Spacious and luxurious, this estate is gated and fenced with a pool, decks, and tropical gardens. To top it off, the property is located in the sought after 19th century Historic Seaport neighborhood.brbrThe picturesque Key West Seaport is just 3 short streets away. Strolling to the harbor takes you past grand wooden homes and adorable cottages hand-built by seafaring merchants. Narrow island streets and lanes line the neighborhood punctuated with white picket fences.brbrA Bit of History brbrThe Key West Historic Seaport neighborhood was the first area to be developed on Key West. Most don`t realize that the bravest of these early builders were 1700`s British loyalist settlers of the Bahamas. These forefathers and mothers created an established sailing route between the sleepy Green Turtle Key in the Bahama Bahamas and the growing trade center of Key West.brbrOver the ensuing 150 years, many British settlers gradually relocated to Key West. Rather than leave home behind, some literally disassembled their wooden houses, and floated them over to Key West and rebuilt them. This remarkable time established architectural roots that still bind the two island cultures together.brbrDuring the early 19th century building frenzy, the seaport became a major world trade center. Regrettably old growth heart pinewood forests in the Florida Keys were decimated by rakish settlers. In return for being cut down, trees were milled into boards that still remain nearly imperviable.brbrThe loss of the old pine forests was partially reconciled with the wooden structures built near the Key West Historic Seaport. Skilled carpenters milled the trees and fashioned the gold colored boards into craftsman structures - from warehouses, to sail lofts, to merchant shops, to hotels, to domiciles. What remain standing in the wake, is a cherished collection of one-of-a kind wooden buildings. Fortunately, unlike the old growth trees, the historic Old Town Key West houses are now permanently protected. They will sustain the changing times.brbrMore than a century has past since most of the buildings were constructed. While many of the structures still stand, their private and commercial use has changed with the times. Sail lofts, warehouses, canneries, and stables have been transformed into a new wave of fashionable enterprises. While the outside of the structures held their original form, inside they`ve been transformed into remarkable places.brbrLAYOUTbrbrMain House:brbrLocated at the front of the property, the 7BR 5.5BA Classic Key West Estate is the perfect place for your group to gather. For a full description of this 2-story Victorian home, please follow this link. The common rooms on the 1st floor provide a spacious living room / media / dining room that connects with a renovated blue and white kitchen with stainless steel appliances and earth-tone granite countertops.brbrThe kitchen is located at the back of the house. Two sets of French doors, at the back corner of the kitchen, lead to the pool deck and garden. Easy access to the kitchen makes the setting ideal for entertaining. The pool deck provides an elegant backyard lounging and dining area. A flat screen TV is placed on the exterior wall above the table for outside media entertainment.brbrAll bedrooms in the main Victorian house are spacious with 12 ft ceilings, and each provides a king size bed. There are 2 bedrooms and 1.5 bathrooms on the first floor and 4 bedrooms and 3 bathrooms on the 2nd floor.brbrAcross the pool deck there`s a free-standing poolside cottage bedroom that provides 2 full size beds and 1 full bathroom. The privacy fence at the back of the pool deck has a gate that leads to the Private Caribbean Guest House. Open the gate for a seamless access between the two dwellings.brbrCaribbean Guest House:brbrThe 3BR 2BA Caribbean Guest House is exotic, private, and luxurious! Situated at the back of the estate property, it was completely renovated in 2021. The renovation expanded this estate to provide 10 bedrooms and 7.5 bathrooms total.brbrThis private guest house provides a special space for the persons who desire privacy from the rest of the larger group. The property owner designed it as a luxurious peaceful retreat, with spaces to relax, read, and quietly enjoy hydrotherapy in an exotic setting.brbrEntering from the pool deck, the front entrance of the guest house steps into the open concept great room. Dark mahogany floors and white walls throughout the integrate the spaces throughout the house. Ceilings in many of the rooms are lined with bamboo paper, creating an exotic-tropical feel.brbrIn the living room, bright green banana leaf print wallpaper is featured on one wall. A modern furniture grouping provides a sofa, two easy chairs, and large flat screen TV mounted on wall. For a surprise, look up! Overhead you`ll notice the unusual hammock netting stretched across part of the ceiling. Look closer for a peek-a-boo view of an unsurpassed meditation loft above.brbrThe modern kitchen also makes an impressive statement. Bright white cabinets with an L-shape breakfast counter and top-of-the line stainless steel appliances complete the space. The kitchen ceiling is finished up to the gable roof line and lined with bamboo paper and contrasting mahogany ceiling beams.brbrLeaving the great room, an L-shape hallway leads to the three bedrooms and two bathrooms. All bathrooms are elegant. The first bathroom is close to the main entrance door. Decorated in bright white with black fixtures, it offers a deep oval-shaped bathtub and a single vanity sink with three drawers. An oval mirror above the sink reflects the nature light that streams in from the three windows above the bathtub.brbrAll bedrooms painted bright white and minimally furnished using tropical textures of bamboo, seagrass, and wicker. Each bedroom offers different bed sizes and unique features and tropical designs.brbrBedroom One: Immediately to the left, the first bedroom is furnished with a full-size (double) bed with sea grass headboard. A custom spiral bright yellow metal ladder leads to the meditation loft above.brbrThe meditation loft is set with seat pillows and lit with artistic lighting. A Buddha statue is placed on one end of the meditation room, backlit by a gable window at the front of the house. Guests are asked to use this unique space respectfully and agree to follow the posted rules, according to the rental contract.brbrDirectly across the hallway from bedroom one, a modern design bathroom is finished in white-on-white tile and marble. The single vanity is topped with a molded sink. The shower is oversized with a rain shower and a wand; all bathroom fixtures are an elegant gold tone.brbrBedroom Two: Directly across the hall from bedroom one, the second bedroom is furnished with modern walnut tone furnishings. A platform queen size bed, featuring an abstract headboard, sits as a center piece in the bright white room. Matching end tables on either side of the bed, and a bureau complete the set. Plantation shutters on the four tall sash windows add to the minimalist island style. An exterior door to the left of the bed, leads to the bathing porch.brbrBedroom Three: The third bedroom is at the end of the hallway. Larger than the other two bedrooms and providing a king size bed, it is considered the master bedroom. Golden bamboo furnishings blend beautifully with the bamboo and mahogany ceiling. French doors to the left of the bed, lead to the bathing porch.brbrExotic Bathing Porch: The Caribbean-style outdoor covered bathing porch is a fabulous feature of the house. Here you enjoy an exotic bathing setting for two - with two deep clawfoot bathtubs surrounded by louvered plantation shutters. If you prefer to shower instead, there is an open shower at the end of the bathing room. The bamboo ceiling is carried to the bathing room, and louvered walls provide plenty of privacy. Hanging orchids and potted palm trees punctuate the tropical design.brbrGrounds:The estate grounds are fenced and gated, with curb views of each house. The back yard the connects the dwellings is completely decked. There is a swimming pool off the back deck closest to the main house. Covered front porches on the 1st and 2nd floor of the main house provide views of famous Fleming St. The 2nd floor verandah on the back of house provides a view of the pool garden below and creates a covered loggia off the pool deck. Mature palm trees and foliage create a romantic tropical setting.brbrBedding SummarybrbrMain House:brbrFirst Floor - Bedroom One - 1 Queen Murphy bed; Bedroom Two - 1 King size bedbrbrSecond Floor - Bedroom Three - 1 King size bed; Bedroom Four - 1 King size bed; Bedroom Five - 1 King size bed; Bedroom 6 - 1 King size bedbrbrPool-side Cottage - 2 full size (double) beds.brbrbrGuest House: brbrbrBedroom One; Full (Double) BedbrbrBedroom Two; Queen Size BedbrbrMaster Bedroom; King Size BedbrbrbrAmenities: Swimming pool, large deck, tropical gardens, expansive porches, and privacy fences. Fully equipped kitchen, central a/c, telephone, TV, stereo, washer / dryer. Linens and towels are provided. Reimbursement for parking of 1 vehicle.brbrRestrictions: While this property is ideal for families and groups to unite, is not suitable for staging loud parties. Smoking permitted outside only. No pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.brPARKING: We reimburse for 1 vehicle.

Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21

Key West, Florida, United States

Bed

Bath

Sleeps

$740.21

Hosted by Luxury Sea Charters, a professional yacht management company based in Key West. Our team is available throughout your stay, ensuring a seamless, safe, and elevated experience from arrival to departure. This floating 46’ yacht offers the comfort of a luxury hotel paired with the unforgettable experience of staying aboard a modern motor yacht.brWellness-inspired yacht with heated lounge seating and a built-in massage couch for effortless relaxation.brbrPerfect for romantic getaways, solo retreats, and anyone dreaming of the true Key West waterfront lifestyle.brbrYour Private On-Water Suite Includes:br • Spacious Primary Bedroom with a queen bed, hotel linens & soft lightingbr • Private En-Suite Bathroom with walk-in shower, vanity storage & hot waterbr • Climate-Controlled Interior with powerful A/Cbr • Indoor Lounge for relaxing, reading, or enjoying morning coffee Wellness-inspired comfort with heated lounge seating and a built-in massage couch for effortless relaxation.br • Mini-Kitchenette with microwave and Keurig br • High-Speed WiFi for streaming and remote workbr • Smart TV with connected apps. This isn’t just a place to sleep — it’s a Key West experience.brWatch yachts glide by, enjoy wine on the deck at sunset, or start your morning with ocean air & quiet marina vibes.brbrGuests consistently say this stay feels:br • Peacefulbr • Privatebr • Romanticbr • Refreshingbr • Exactly what they neededbrbrYou’re close to everything Key West offers, yet tucked away from the noise.brbrLuxury Sea Charters is well known in Key West for premium yacht stays and marina experiences. Guests frequently look us up online to learn more about our amenities and local enhancements before arrival.brbr⸻brbrLocation Highlightsbr • Minutes from Old Town & Duval Street by free shuttle br • Surrounded by local dining, coffee shops & waterfront barsbr • Easy access to beaches, charters & water activitiesbr • Safe, secure marina with guest parkingbr • Beautiful walking paths and photo-worthy viewsbrbr⸻brbrWhat to Expect on a Yacht StaybrbrYour suite is clean, comfortable, and upgraded for easy marina living.brLike all boats, it has steps, narrow areas, and gentle movement from the water — most guests love the relaxing sway.brbrIf you’re looking for a unique, boutique Key West stay, this is it.brbr⸻brbrPerfect For:br • Anniversary tripsbr • Couples getawaysbr • Solo resetsbr • Content creatorsbr • Digital nomadsbr • Travelers who want something memorable vs. a hotel roombrbr⸻brbrYour HostsbrbrWe are passionate about sharing the yacht lifestyle and ensuring your stay is smooth, relaxing, and unforgettable. We’re nearby if during the day if you need anything and love helping guests make the most of their time in Key West.

House Boat

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

Key West, Florida, United States

Bed

Bath

Sleeps

$617.63

You and your guests will have exclusive use of this 40ft yacht all to yourselves. The yacht stays docked, the entire reservation, at the Perry Hotel, which invites you to complimentary use of two stunning waterfront swimming pools, live music, three restaurants, complimentary shuttle service, & more. You and your guests can come and go on the yacht anytime, day or night.brbrDue to local regulations, it is required that you choose at least one of the following options during your reservation: a two-hour sunset sail, a four-hour excursion, an eight-hour excursion, a ten-hour excursion, or a 24-hour excursion.brbr- 2-hour excursion: $900+tax & gratuity (sunset cruise only)br- 4-hour excursion: $1450+tax & gratuitybr- 8-hour excursion: $1950+tax & gratuitybr- 10-hour excursion: $2200+tax & gratuitybr- 24-hour excursion: $2500+tax & gratuity brbrThe prices listed above are per excursion and not per person. The cost of the excursions must be paid directly to our company at the time of booking. The prices listed above include the captain's fee and fuel, however, does not include gratuity.brbrThese excursions are highly recommended by our previous guests and are sure to provide you with a memorable experience. During these outings, you'll have the opportunity to learn how to navigate the yacht, snorkel around the coral reef, fish from the yacht, spot dolphins and sea turtles, and much more. (Snorkeling and fishing gear is not included, but it is available for rent).brbrOur 24-hour charter is particularly popular as it combines the activities of a day excursion with the unique experience of spending a night anchored on the ocean with a limit of 6 total guests. If you are staying for more than two nights, you can even enjoy multiple excursions during your reservation period.brbrJust imagine sleeping under the stars with no neighbors next to, above, or below you like in a hotel room. You can spend your days and nights fishing from the boat, relax on the deck while listening to the sounds of tropical fish jumping in the water, and experience the thrill of being away from the marina, anchored on the ocean. If you're seeking an adventurous and extraordinary vacation surrounded by breathtaking ocean views, wildlife, and fish, this is the perfect choice for you. You might never want to return to land again!brbrThe weather in this area is ideal throughout the year for activities such as snorkeling, fishing, lobster catching (seasonal), kayaking, paddleboarding, learning to sail, scuba diving, or simply enjoying a relaxing sunset cruise.brbrIn addition to our excursions, we provide an exceptional concierge service that brings luxury directly to you. For an additional cost, our offerings include VIP packages, chef services, catering, provisioning, limo service, golf cart rentals, sporting goods rentals, and much more.brbrThe Perry Hotel is a pristine resort located in the heart of a turquoise paradise with crystal-clear waters. Your stay at the hotel includes access to two waterfront swimming pools, live music performances, a fitness room, three restaurants, retail shops, marina showers, laundry facilities, and more. The Perry Hotel also offers complimentary shuttle service to and from downtown Key West, which is conveniently located nearby. Additionally, the resort is in close proximity to retail shops, grocery stores, restaurants, and various attractions.brbrThis yacht is one of a kind with its three-stateroom layout. The entire starboard side is a master suite with a private shower and a small desk area. The two other staterooms are separated by a bathroom with shower. One has a double bed, the other a queen. brbrIf you're interested in a bareboat charter to the Dry Tortugas, please note that a minimum of five nights is required. In addition to the payment made through VRBO, you would need to purchase three 24-hour excursions, allowing you to spend one night at the Dry Tortugas. On your way to and from the destination, you would also stay at the Marquesas Islands, which are located halfway. This charter is truly a once-in-a-lifetime experience that will provide memories to cherish forever. Due to the distance, it is not possible to make the trip to the Dry Tortugas and back in just one day. brbrWe also offer charters to popular destinations such as Little Palm Island, Bahia Honda State Park, Marathon, Islamorada, Key Largo, and more.brbrThe excursions/charters offered are discounted from the regular price and must be paid directly to our company outside of VRBO at the time of booking.brbrWe also offer bareboat day charters where you do not have to stay overnight on the boat. This type of charter must be booked directly through our company as VRBO is only set up for overnight accommodation bookings.brbrOur company also offers snorkel gear, wet suits, fishing gear, e-bikes, scooters, golf carts, kayaks, and paddle board rentals, for an additional cost, to truly take in Key West. brbrIf you want to operate the boat or tender yourself you must book directly with our company to go through an approval process. Taking the vessel yourself (and not hiring a captain) is subject to prior experience on similar vessels. brbrThe advertised price on this listing covers the cost of insurance that covers you and the crew during your reservation period as well as the cost to survey the boat after you leave. You will be required to undergo a bareboat contract and will take full responsibility of the operation and safety of the yacht, crew, and all passengers.brbrAdditional House Rules:brbr1. There is a $50 charge per night per person over four. There is a $100 fee to make any changes to your charter after your paperwork has been drafted and emailed to you up to 3 days prior to check in. There is a $200 fee to make any changes to your charter after your paperwork has been drafted and emailed to you 3 days or less prior to check in.brbr2. There is a $150 fee to add additional guests on an excursion, not staying overnight after your paperwork has been processed, up to 3 days prior to check in, and $200 per guest not staying overnight, 3 days or less prior to check in on a day charter. brbr3. As posted in this listing, you must pay our company directly for at least one excursion at the time of booking. In the event you refuse to book an excursion, your reservation will be canceled with no refund. There is no refund for a paid excursion in the event the excursion is canceled and there is available time left in your reservation to reschedule it to.brbr4. There are no refunds for a change in number of guests. There is $100 extra guest fee per person that is joining you on a day charter that is not staying overnight. brbrGuests must be able to walk up & down stairs inside the boat and be able to make a longer than usual step at times to get on and off the boat.brbrWe have other yachts available if this yacht does not meet your specifications.

House Boat

Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!

Key West, Florida, United States

Bed

Bath

Sleeps

$186.95

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 30 night minimum.brbrFEATURES:brBedrooms: 2 - One upstairs and one downstairs (Queen in both rooms)brBathrooms: 2brLocation: Southard St in Old TownbrSquare Feet: 1054brParking: 1 reserved parking spacebrAmenities: Shared pool, Wifi, TVs, in-unit laundry, walkable to shops and restaurantsbrbrbrTHINGS 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.

Apartment

Southard Retreat- 2 bed 2 bath townhome downtown w/ pool, parking

Key West, Florida, United States

Bed

Bath

Sleeps

$329.79

HIDDEN GEM...brThe perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cottage with Old Town Key West charm. Nestled on a hidden lane one block from Duval, you will find The Nest, a hidden gem.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrSLEEPING ARRANGEMENTS...brSpacious Master Bedroom with cozy and comfortable queen bed, ensuite bath with twin vanities and large shower. The second bedroom has twin beds and the full hallway bath is a shower/tub combo. The washer/dryer is conveniently located in a hallway closet near the bedrooms. Click on the virtual tour link to walk through the home and see the layout and imagine yourself there!brbrAMENITIES AND FURNISHINGS...brBeautiful bamboo flooring provides warmth and a tropical feel. Beautiful blue sky and Key West sunshine fill the rooms with natural light from the many windows. Every amenity has been thoughtfully added for your comfort to provide a true home away from home experience. Tropical decor with pops of color remind you of your island vacation at every turn. Spacious open floor plan includes gourmet kitchen for casual dining, living room with flat screen TV and French doors to the delightful outdoor space. A heated plunge pool with a charcoal grill is ideal after a day of playing in Paradise. brbrPARKING...brParking for 2 small cars or 1 large car/van is provided, but at this location, you can stroll or bike to all Key West has to offer.brbrPETS... brDogs under 25 lbs are considered at this home and a pet fee is required. Please include 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)br brBOOKING DATES...brWe 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!brbrTRUE PARADISE VACATION...

THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$178.42

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCOMFORT AND VALUE IN TRUMAN ANNEX…brThis newly renovated 2nd floor two bedroom condo is located in The Shipyard, a neighborhood of Truman Annex in the heart of Old Town Key West! Colorful, fun patterns fill the rental with life while the furnishings provide a comfortable gathering space for your group. The sunny deck overlooks the distance views of the ocean through the lush trees but can also be a shady retreat with the help of an awning. This unit is accessed via one flight of stairs.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrFURNISHINGS…brThe Quarterdeck’s open floor plan and ample seating provides the perfect space for your group to enjoy together. Curl up on the couch and watch a movie on the flat screen, gather around the dining table to play a game or cook together in the fully equipped kitchen!brbrSLEEPING ARRANGEMENTS…brBoth guest rooms have a comfortable queen bed with extra drawers built into the bed frames for maximum storage space! Each room has a closet with lots of hanging space a flat screen TV, tile throughout and new paint for a fresh, clean feel. brbrDETAILS AND AMENITIES…brSettled in the manicured, gated community of The Shipyard, this location offers guests a peaceful spot to relax just a block from all the action! You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! The Shipyard also offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Parking is always an issue in Old Town, but this condo comes with its own designated parking space (vehicle cannot exceed 18 ft.)brbrOUTDOOR LIVING…brOpen the French doors to the back deck letting in the great breezes and sun rays that fill the space throughout the day. This wonderful extension to the living space has a table for two where you can have your morning coffee or enjoy a cocktail after a long day of exploring. On hot summer days pull out the awning to push back the sun so you can enjoy the views without sitting in the direct sunlight.brbrPETS...brThe is not a pet friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrbrBOOKING 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. brbrPARKING!brThis home does offer parking for one vehicle (cannot exceed 18 ft), but oversized trucks and extra large SUV's are not permitted and will have to park outside of this community.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!brbrCOME STAY A WHILE...

THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Shipyard Unit!

Key West, Florida, United States

Bed

Bath

Sleeps

$396.45

Your Peaceful Key West Escape Awaits! brbrWelcome to this comfortably appointed 2-bedroom, 2-bath condo located in the desirable Sunrise Suites complex—a quiet, well-maintained community offering privacy and relaxation away from the hustle of Old Town Key West, yet close enough to enjoy it all. brbrCOMFORTABLE & THOUGHTFULLY DESIGNED INTERIORbrStep inside and feel right at home in this bright and welcoming space. The condo features:br- Primary bedroom with a king bed and private en-suite bathroombr- Second bedroom with a queen bed, also with its own en-suite bathroombr- Spacious living room with a sofa sleeper for extra guestsbrEach bathroom is well stocked and includes a bathtub and hair dryer for added convenience. brbrFULLY EQUIPPED KITCHEN & DININGbrThe efficient kitchen is perfect for preparing meals or light snacks and includes:br- Standard appliancesbr- Breakfast bar seatingbr- Keurig / drip coffee maker combobrPlenty of cookware, utensils, bowls, pots, and pansbrWhether you’re enjoying a quick breakfast or winding down with dinner, you’ll have everything you need.brbrPRIVATE LANAIbrThe open living room leads to your private lanai overlooking the tennis courts—a great spot to enjoy your morning coffee or unwind after a day at the beach .brbrPRIME END LOCATIONbrThis condo is an end unit on the 3rd floor, offering extra privacy and convenience. You’ll be just steps away frombr- Shared swimming poolbr- Tennis courtsbr- Fitness facilitybr- Shared laundry areabrbrIDEAL LOCATIONbr- Close to the beach and Key West International Airport brJust a quick Uber or drive to downtown Key West (approximately 2 miles) br- A small convenience store located within the Seaside complex, perfect for quick essentialsbr-Parking & ComfortbrParking for one vehicle includedbr-Central air conditioning and heating ensure year-round comfortbrbrRELAX, RECHARGE & ENJOYbrWhether you’re exploring the island, lounging by the pool, or savoring peaceful mornings on the lanai, this gorgeous condo offers the perfect blend of comfort, location, and tranquility.brbrWe look forward to hosting you and hope you enjoy your stay in beautiful Key West!

SEASIDE ESCAPE- 2 Bed/2 Bath Condo With Shared Pool & Parking

Key West, Florida, United States

Bed