Vacation Home Rentals By Owner In Key West, FL

Galveston Porches – Stylish One-Bedroom in the Heart of Old Town Key WestbrbrWelcome to Galveston Porches, your perfect home-away-from-home in the heart of Old Town Key West. This beautifully renovated and thoughtfully decorated one-bedroom apartment offers everything you need for a comfortable and stylish extended stay.brbrEnjoy your mornings with coffee on the spacious private balcony, soaking in the charm of the historic neighborhood. Inside, you’ll find a fully equipped kitchen, washer and dryer, central AC, and high-speed WiFi—every modern convenience wrapped in island charm.brbrLocated just a few short blocks from world-famous Duval Street, you’re within easy reach of Key West’s best restaurants, nightlife, and attractions—yet tucked away in a quiet, residential enclave.brbrFeatures include:br One bedroom, fully furnished and beautifully decoratedbr Full kitchen with modern appliancesbr Washer and dryer in unitbr Central air conditioningbr High-speed WiFibr Spacious private balcony with Old Town viewsbr One assigned parking spacebr Quiet, walkable neighborhood near all the actionbrbrWhether you're here to relax, work remotely, or explore everything Key West has to offer, Galveston Porches is your ideal island retreat.

Apartment

Chic 1BR wonderful porches, heart of Old Town Key West. Total renovation.

KEY WEST, Florida, United States

1

Bed

1

Bath

Sleeps

Select Dates for Price

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and paper products along with handsoap and toiletries. The home has a private entrance and contactless Check-In/Out.brbrNeed to stay connected during your trip We offer high speed cable internet.brbrLocated in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval St. We are just outside the entrance to Ft Zachary Taylor State Park and Beach and so close to many of Key West’s popular attractions. After a full day of taking in many of the island's wonderful experiences, come back to all the comforts of home. This open airy home offers a fully furnished kitchen, eating area, living room and 2 bedrooms and 2 1/2 baths. Two sets of French doors open to a large deck and beautiful private backyard where you can enjoy a meal or relax and sip umbrella drinks on the chaise lounges in your own private tropical paradise. Gated parking lot with one reserved space.brbrAmenitiesbrbr- Televisions in bedrooms and living areabrbr- 2 Bicycles for Guests to use during their staybrbr- Bed Linens, Bath & Beach Towels brbr- Hairdryerbrbr- Beach Chairs & Coolerbrbr- Access to Southard Court Poolbrbr- Balconies off each bedroom and private enclosed backyard with deckbrbr- Reserved parking place in front of homebrbr- Secure high speed wireless internetbrbr- Only a few short blocks from Duval Street and Mallory Squarebrbr- Short walk to the Fort Zachary Taylor State Park Beachbrbr- Fully equipped Kitchen with Silestone counter and eat in bar- Silverware, Dishes, Cooking Utensils Provided, Stove/Oven, Refrigerator, Microwave, Dishwasher, Coffee Maker & Blender

Location, Beauty & Comfort @ Truman Annex

Key West, Florida, United States

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Bath

Sleeps

$784.13

Key West is waiting for you at this clean & spacious 2-bedroom guest house. Good for up to 6 people. This cozy retreat offers an office table for those who need to squeeze in a little work time as well. The shared backyard offers a plunge pool, lounge chairs, propane BBQ, & roof deck. Our place will help you feel at home while you're traveling in Key West. Guests love being able to walk to so many landmarks and restaurants in the area. Access to guest house is through Elgin Ln alley way.brbr1 onsite parking spot in front of the house is included for regular & compact vehicles. There's a parking garage located just 1.5 blocks away.brbrGuest House:brRoom 6: King bed, downstairs, ensuite bathroombrRoom 7: (living room/couch/queen Murphey bed cabinet/kitchenette as seen in photo) flex space w/bathroombrRoom 8: King bed, downstairs, ensuite bathroombrbrWe offer a portable crib please request in advance. Subject to availability. brNo laundry room or kitchen sink available.

Charming 2 room guest house, access to Pool, A/C, & WiFi, Key West, near Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$1662.75

Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. Explore the city then come back home to hang out with family & friends or by the plunge pool. There is an outdoor shower and propane gas BBQ available for use. 1 onsite parking spots included for regular or compact vehicle. Large/oversized SUV may find it difficult to park side by side. There is a parking garage located just 1.5 blocks away for additional vehicles.brbrMain House:brRoom 1 - located downstairs w/ensuite bathroombrRoom 2, 3, 4, & 5 - located upstairs with ensuite bathroombrLiving room has TV and gamesbrKitchen, laundry room, & small dining areabrbrWe offer a portable crib, please request in advance. Subject to availability. brOutdoor areas are shared with any guests that book the guest house. Please don't ask if guest house is booked or not. The occupancy status can change daily. If you would like to have the entire place to yourself, please book entire home.

Spacious 5-bdrm 5 bathroom house in charming Key West with AC, WiFi, Plunge Pool

Key West, Florida, United States

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Bath

Sleeps

$412.62

MODERN CUSTOM ELEGANCE…brSurrender your cares in this tropical state-of-the-art luxury sanctuary! If nothing but the latest and greatest will suffice, this modern beauty merges clean lines with the ultimate flow in design and cradles you in crisp yet cozy spaces. Nestled in the exclusive Casa Marina neighborhood, this residence features 2 bedrooms and 2 bathrooms - a perfect retreat for 2 couples seeking island serenity with a nod to cutting-edge visual aesthetics. Bonus item is a mere 3 minute walk to the beach!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE. THIS HOME IS NOT SUITABLE FOR CHILDREN.brbrDETAILS AND AMENITIES...brIndulge in the utmost privacy as you enter the exquisite design interior. The chef's kitchen boasts Miele appliances with a center Carrera marble island that opens to the living/dining areas, showcasing a dramatic collapsing wall of sliding doors that invite the backyard oasis indoors in classic Key West fashion. Plush couches and a large wall-mounted TV in the living space encourage lazy conversations amidst peaceful outside water sounds or an evening of movie watching with a cool aperitif on the coffee table. For your convenience, a washer/dryer closet is located outside, just off the primary bedroom. brbrSLEEPING ARRANGEMENTS...brThe primary bedroom whispers privacy and intimacy, featuring a king size bed, dual sink, large shower bathroom, walk-in closet, wall-mounted tv, and a wall of windows that open to a private patio that houses a delightful outdoor shower. On the other side of the kitchen you'll find the guest bedroom with two twin beds that can be converted to a king bed upon request and its own gorgeous ensuite large shower bathroom, desk area, 2 closets, and a wall-mounted tv. brbrOUTDOOR LIVING...brThe glamorous enclosed backyard garden and pool area was designed by Craig Reynolds and has been featured in Dwell Magazine. There are defined gathering spaces for sunbathing, outdoor dining and a fire pit with seating for 4 for the occasional cool evening. The saltwater pool can be heated with a waterfall feature. Wash the day off under the outdoor shower then toss steaks or your fresh catch onto the stainless Weber propane grill. brbrPARKING...brThere is off-street parking available.brbrPETS...brDogs are considered at 35 lbs or under 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)brbrBOOKING DATES...brThis home is offered only as a monthly rental (28 night min.). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. 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).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!brbrRESTORE AND REHABILITATE IN STYLE…

GOLDEN HOUR ~ Upscale 2 BR/2Ba Home w/ Pool!

Key West, Florida, United States

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Bath

4

Sleeps

$976.34

A tropical retreat overlooking the Atlantic Ocean. Windward Pointe captures the essence of Key West. The resort boasts freeform infinity edge poolside restaurant. Lots of games. Nearby Smathers Beach. Rooms are fully equipped and feel more like a condo.

Hotel Resort

Hyatt Windward Pointe Nov 2-Nov 7 2026 Boat Race Week.

Key West, Florida, United States

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Bath

Sleeps

$6075.0

brStay comfortably in Key West at this amazing 6-bedroom yacht. With 5 queen beds and 1 single bed, this luxury yacht offers a unique and cozy stay for guests. Each of the 6 bedrooms and 6 bathrooms is fully equipped for your comfort. brbrExperience the ultimate Key West adventure aboard our luxurious 64' Lagoon Catamaran. With spacious decks, plush seating, and unparalleled views, this stunning vessel offers the perfect setting for your group to relax, explore, and enjoy the crystal-clear waters of the Florida Keys. Whether you're cruising, snorkeling, or watching a breathtaking sunset, our catamaran provides comfort and style, making it the ideal choice for a memorable day on the water.brbrIt includes the stay onboard and 24/7 cruising to various destinations like Key West, Dry Tortugas, Miami, Bahamas with full time crew, fuel, tender boat, jet ski, 2 paddle boards, water toys.

House Boat

Luxurious Atlantia 2020 6-bedrooms 64ft yacht with full time crew

Key West, Florida, United States

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Select Dates for Price

Welcome to your home away from home! Casa Amelia is a charming Conch house in the historic Gato Cigar Village. Wake up in the morning and sip coffee in comfort on the covered front porch. In the afternoon, enjoy a private backyard, swimming pool and tiki bar, or venture out to famous Duval Street, only steps away for a day of shopping and bar-hopping. This is the perfect vacation getaway in the heart of Old Town Key West. Just a half-block off Duval Street with off-street parking, a big plus! Location, location, location! Our home is just around the corner from Key West Light House, the Hemingway house, Southernmost point and many restaurants, bars and galleries. Simply park and walk. Casa Amelia is also on the free Duval Loop Route. Take the free bus to the Historic Seaport. We are stop number 9.brbrAccommodationsbrOur home is a 3 bedroom and 2 bath home. The first bedroom has 2 twin beds and is right off the living room. The second bedroom has a queen-size bed and TV and is off the dining room and connects to the main bathroom. The third bedroom has a queen-size bed, TV and bathroom located at the back of the house off the kitchen.brbrAmenitiesbrCasa Amelia includes a washer and dryer, central A/C and heat, TVs in 2 bedrooms and living room, fully equipped kitchen, starter supply of paper products, starter set of cleaning products,iron and ironing board, linens, bath and pool towels, Wifi, Direct TV, private heated pool, Tiki bar, off-street parking, propane BBQ grill, cleaning service bi-weekly.

*Casa-Amelia-Key-West* 1/2 block off Duval Street

Key West, Florida, United States

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Bath

Sleeps

$404.36

Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just three miles from vibrant Duval Street, and four miles from historic and majestic Mallory Square.brbrThe property features two pools, a hot tub, park-style grills, picnic tables, onsite bar, and much more.brThis spacious two bedroom condo features a king primary suite with hardwood flooring, a connecting ensuite full bathroom with shower and bath tub. The guest bedroom features a queen bed with wood flooring. The condo also features a full kitchen, with a full refrigerator, microwave, stove, oven, dishwasher, coffee maker (drip style), toaster, blender, dishes and utensils. The living room features a queen-size sleeper sofa, HD TV, a dining area and access to a private patio. This is a two-story condo and the bedrooms are upstairs.brbr*Must climb stairs — Stairs required to access the unit, Stairs may be required to access bedroomsbrbrGuest must be 25 yrs old to rent and check-in to this unit.brbrUnits are assigned in seven night increments, multiple week stays may be booked, room moves may be required.brOccupancy limits are strictly enforced.brbrNo RVs, campers or mobile homes may be parked on the premises. Parking is limited to two (2) vehicles per unit.brbrWelcome Center hours of operation are: Sunday to Thursday 9am – 5pm and Friday/Saturday 8am – 10pm. Late arrivals must call the welcome center for arrangements.brbrAn ID and a credit card is required upon arrival for a refundable security deposit.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.brbrGumbos is not currently operating as a bar or restaurant.brbrLaundry facilities located on top floor of buildings for a fee. Towel Exchange is not available.brbrPictures are representative of units on property. All feature similar layouts, decor and amenities. Property features most 2 story units. There exists a chance you may be assigned a single story unit. Specific unit is assigned at check-in by the front desk.

Waterfront Property - Marina Access - Spacious - Excellent Key West Condo

Key West, Florida, United States

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Bath

Sleeps

$204.8

A TRUE CARIBBEAN PARADISE! Location! Location! Location! brStarting Jan 2026 , this beautiful cottage will become monthly! Stays will have to be 28- 30 days. Discount of 10% for monthly stays. Make plans to stay longer, relax or work remotely from paradise for a full month in 2026. brThe Conch Retreat Condo is located in the prestigious Truman Annex. This condo has 2 bedrooms, 1 bath, queen and 2 twins (or we can convert the twins to a king bed upon request). both TV's with cable.brFree parking spot comes with condo, however you don't need a car. Free High Speed Internet. There are 2 bicycles for your use with helmets. brFully equipped kitchen. Has everything you need for your stay. brThis upper floor condo has doors that open up to back deck where you can relax around the tropical trees. Great for your morning coffee and reading. Bathroom with walk in shower, medicine cabinet and storage cabinet. Vanity and shelves for storage. brWasher & dryer with iron & ironing board. brLiving/Dining area has table with seating for four. brFront balcony opens up from kitchen with seating. brAll towels & Linens including beach towels.brLarge heated Pool for Shipyard guests only. brYou are in a gated community off of street in a quiet community.brExplore the Waterfront/water park behind the complex. Amphitheater, splash park, playground. Stroll to the Waterfront Pier and enjoy the sunsets and sailboats. Mallory Square is famous for local vendors and amazing sunset celebrations. brRoad to Fort Zachary Beach is directly behind complex. You have opportunities for swimming, picnic, grilling, snorkeling, and fishing. Visitors can also enjoy a short nature trail and bicycling within the park. The beachfront Cayo Hueso Café offers snacks, cold beverages, beach sundries, and souvenirs. Two blocks to Duval where you will find shopping, restaurants, night clubs and museums. Visit the Historic Seaport District where you will find dining, entertainment or catch a sunset cruise. There is so much to see and do. My husband and I take pride in our vacation homes. It's our home away from home and want our guests to be comfortable and enjoy what Key West has to offer. brWe're offering discounts for monthly stays.brTo see our other VRBO Key West listings:brTruman Annex Shipyard (1 bed, 1 bath) Island Escape vrbo.com/934388habrTruman Annex Shipyard (3 bed, 2 bath) Sea Breeze Cottage vrbo.com/987489ha

CONCH RETREAT Truman Annex Condo - 2 decks, pool, 2 Bikes, Free parking and WIFI

Key West, Florida, United States

Bed

Bath

Sleeps

$220.04

OLD TOWN GEM...brThis 2 bedroom, 2 bathroom cutie resides down a charming lane surrounded by historic residences and is a stone's throw from world -class dining, shopping, galleries, and the Historic Seaport. Ease on down to this idyllic sanctuary and watch your cares melt away in Paradise!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brBegin your Key West story in this delightful abode that offers all the creature comforts and promises hours of serenity and bliss. Plan your day's adventures over a hot cup of coffee on the quaint front porch with seating. Enter your retreat from reality and enjoy your delightful living area that invites you to indulge in your favorite TV shows or escape into your latest vacation novel. The spacious and modern kitchen comes fully equipped with all the culinary tools you'll need to create fresh fare and craft icy cocktails. Enjoy seating at the breakfast bar while you feast with loved ones. A stacked washer/dryer closet is just off the kitchen for your convenience.brbrSLEEPING ARRANGEMENTS…brSink into slumber in one of the 2 queen bedrooms. The primary bedroom is located upstairs with an en suite shower bathroom and a desk for those working remotely. The downstairs bedroom resides next to a full bathroom with a shower/tub combination. A sleeper sofa with a very cozy mattress resides in the living room for additional sleeping arrangements. brbrOUTDOOR LIVING…brFrench doors in the kitchen lead to your covered sanctuary. Fire up the grill on your enclosed and private deck area. This cheerful space invites hours of happy conversations or opportunities for quiet solitude. brbrPARKING... brThis home has on street parking only.brbrBOOKING DATES...brThis home is offered only as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrPETS...brThis NOT a pet-friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)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% refundbrbrCancellations 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).brbrGET ON ISLAND TIME…

WASTIN' A WAYLAND ~ Renovated 2 BR/2 Ba Home in Old Town!

Key West, Florida, United States

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Bath

Sleeps

$811.75

Nestled in the highly desirable Historic Seaport neighborhood, 1015 Eaton Street is a thoughtfully renovated 4 bedroom, 3 bathroom Historic Eyebrow home that perfectly blends timeless Key West architecture with modern luxury. Behind the white picket fence, a welcoming front porch sets the tone for effortless island living. Open the front door, crowned with a stained-glass transom, and be welcomed by rich Dade County pine floors and walls adorned with elegant wallpaper. The open-concept living space features soaring ceilings and a stunning waterfall island anchoring the chef's kitchen, complete with stainless steel appliances and marble countertops. Natural light pours in through wall-to-wall impact sliding glass doors, creating a seamless flow between indoor and outdoor living. The primary ensuite bedroom on the main floor offers spa-like tranquility, with a basalt accent wall, natural finishes, and direct access to the pool deck. A second ensuite bedroom on the main floor currently functions as an entertainment room, complete with a pullout couch and TV--perfect for guests or flexible living. Two additional upstairs bedrooms and full bath provide comfort and privacy for family and friends. All bathrooms feature porcelain tile, custom anti-fog mirrors, and designer fixtures. Step outside to your fully fenced private outdoor oasis with IPE decking, a dazzling saltwater pool and a glass-tiled waterfall--ideal for entertaining or relaxing in island-style tranquility. Located just steps from Key West's world-class dining, marinas, shopping, and attractions, this home presents a rare opportunity to own a piece of paradise in one of the island's most sought-after neighborhoods.

Charming 4-bedroom house with pool - 10 MIN. WALK TO DUVAL STREET

Key West, Florida, United States

4

Bed

Bath

8

Sleeps

$423.3

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrThere’s no better way to spend a Key West vacation than in a freshly renovated home that offers a luxurious, private escape in a prime, convenient location. THE ARTIST’S AVIARY is exactly that! Blending historic charm with modern amenities, this impressive 3 bedroom, 3.5 bathroom home features a private pool, off-street parking, and double front porches gracing the façade. Located on Ashe Street, THE ARTIST’S AVIARY is within walking distance of world-famous Duval Street and the Historic Seaport, yet it’s tucked away on one of the quietest and most desirable residential streets in Old Town. A month at THE ARTIST’S AVIARY includes Last Key Realty’s First-class Guest Services & In-house Concierge, making it the ideal artistic haven for an unforgettable island getaway.brbrTHE LIVING AREA & KITCHEN…brbrCompletely renovated from top to bottom, you’ll quickly appreciate the thoughtful design and classy finishes as soon as you step inside. The open living area boasts a large flat screen TV and plenty of comfortable seating options. The fully equipped kitchen features brand-new stainless-steel appliances and all the tools the chef in your group will need to prepare home cooked meals. The dining table seats six comfortably, and there’s a convenient half bathroom located just off the living area.brbrTHE BACK PATIO & POOL…brbrStepping outside to the back patio, you’ll be greeted with the soothing sound of the pool’s waterfall. Fully fenced, the pool and patio are completely private, and the pool can be heated to your liking in the cooler months. There are zero-gravity loungers on the patio for the sun worshipers in your group, and a large umbrella for those that want to stay cool in the shade. Treat your group to a BBQ using the two-burner propane grill.brbrTHE LOCATION…brbrTHE ARTIST’S AVIARY is located on Ashe Street, a quiet residential street that’s a short stroll or bike ride from all the shops, restaurants, and attractions of Duval Street and the Historic Seaport. Spend your days exploring Old Town and experience the best of Key West, such as local favorites like 22 & Co, DJ’s Clam Shack, and Kaya Island Eats. Just a few blocks down, you’ll find yourself at The Waterfront Brewery, Schooner Wharf, and all the local favorites of the Seaport. Although you won’t need a vehicle to get around from this prime location, there is off-street parking for one small vehicle available in the private driveway.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom: Located on the First Floor with a King bed, a flat-screen TV, a large closet, and a gorgeous en-suite bathroom with a walk-in shower.brbr** Second Bedroom: Located on the Second Floor with a Queen bed, a flat-screen TV, a closet, and an en-suite bathroom with a shower and tub combo.brbr** Third Bedroom: Located on the Second Floor with a Queen bed, a flat-screen TV, a closet, 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** Smart Home Technologybr** Fully Fenced Private Patiobr** Private Heated Poolbr** Propane BBQ Grillbr** Off-street Parking in Driveway for One Small Vehicle (size restrictions - 9'ft wide by 18' ft deep)brbrOther 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 6 adultsbr** No Pets Allowedbr** 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.

**THE ARTIST’S AVIARY @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVIC

Key West, Florida, United States

Bed

Bath

Sleeps

$244.93

TRUMAN ANNEX: brbrPLEASE NOTE: As Of January 2026, This property is switching to monthly rentals. Please inquire with host first. brbrThe Rooster Retreat is a lovely two bedroom, one bathroom ground floor end unit with a spacious backyard deck. brThe master bedroom offers one king size bed, ceiling fan, 55 TV and double french doors that open onto the back deck. brThe queen bedroom offers natural light through the front window, ceiling fan and 55 TV.brThe bathroom, located in the common area between the two bedrooms, offers a recently updated vanity and walk-in shower.brbrThis unit is cleaned regularly by our local cleaning service and we are following CDC guidelines for cleaning/disinfectants. Read our reviews, we have always been known to have a spotless, clean place - and we've increased our care. Stay with us!brbrBeing at the far end corner of the property, unit #175 boasts added privacy compared to neighboring units. Unique to this floor plan is the added natural light from the extra exterior wall and window. Enjoy the open kitchen to living room layout, large leather sectional and newly added 65 Sony TV. You will be just a short walk from Truman Water Front park and Coffee Butler Amphitheater. Pack a picnic and take a short bike ride to nearby Fort Zachary Beach.brbrThis sunny ground floor condo is clean with well-appointed bedrooms, beautiful linens and art work. Enjoy the breeze on a cool night with open double french doors in the master bedroom. The newly remodeled kitchen with quartz countertops, thoughtfully placed lighting and seating for four is both stylish and functional. A washer/dryer are located within the unit for your convenience. The kitchen is fully equipped with pots & pans, dish towels and dish ware. Enjoy central air conditioning, on-site laundry and all the necessities for both long and short-term stays. brbrRelax at the Truman Annex Shipyard Pool - located within the property grounds.brOur condo is outfitted with beach towels, beach chairs, coolers, etc. We also have designated on-site parking, although it's likely you will not need (or want) to get in your car while you're here. brbr(Due to fire code ordinance, this condo is unable to have an outdoor grill, much like many other condos on the island.)brbrThank you.brbr2019 New deck and landscapingbrbr2018 and 2017 CONDO UPDATES: New bathroom, All new AC & air handler,

Two Bed One Bath Ground Floor End Unit in the Heart of Old Town

Key West, Florida, United States

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Bath

Sleeps

$625.8

This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaza & refreshing pool. The gourmet kitchen features 'Blue Viola granite counter tops, custom cabinetry, stainless steel appliances and a large entertaining island including wine storage. There are 3 large bedrooms on the first floor; each beautifully appointed with luxury linens and furnishings. The generous living room and private dining room feature hand painted finishes, with sumptuous furniture while merging seamlessly with the indoor/outdoor lifestyle Key West is famous for. The second floor has two elegant bedrooms with walk in closets and baths ensuite. There is covered parking for one vehicle and plenty of space to bring in your island bicycles, mopeds or golf carts! Nearby enjoy Higgs Beach, Salute Restaurant, Louie's Backyard, and the White Street gallery district! NOTE: This property is monthly rental - 28 night minimum.

A Bella Capri in Key West by the Beach!

Key West, Florida, United States

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Bath

Sleeps

$361.07

Welcome to Palm Isle! brbr brbrA tropical 2nd-floor condo in the charming Meadows area of Key West. Relax on your private front porch, perfect for watching the world go by, or retreat to your private back porch overlooking the common area with a shared pool and BBQ grill. Just six blocks from Duval Street and the Historic Seaport, and only a mile from Higgs Beach, this location offers easy access to all the best that Key West has to offer. Palm Isle is the perfect home base for your island getaway. brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom: King Bed, TV brbr brbrLiving Room: Sofa w/ Pull Out Queen Bed, Chair, Smart TV brbr brbrKitchen: Nicely equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Heated (Nov-Apr) Pool brbr brbr- Shared Propane BBQ Grill brbr brbr- Private Deck brbr brbr- Outdoor Table and Seating brbr brbr- Drip Coffee Maker, Toaster, Blender brbr brbr- Street Parking (no off-street parking available) brbr brbr- Bike Rack brbr brbr- Linens and towels provided brbr brbr- 0.7 miles to Duval Street brbr brbr- 0.9 miles to Key West Historic Seaport brbr brbr- 1.1 miles to Southernmost Point brbr brbr- 1.4 miles to Mallory Square brbr brbr- 1.4 miles to Fort Zachary Taylor State Park Beach brbr brbr- 1.9 miles to Smathers 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 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 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.

Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches

Key West, Florida, United States

Bed

Bath

Sleeps

$267.19

Step back into 1968 and experience the Florida Keys from the water. This 40' 2 bedroom 2 bathroom Hatteras is perfect for travelers who prioritize adventure, location, and value over luxury. If you are looking for a sterile 5 star resort experience, this is not the place for you. But if you want a safe, clean, and affordable old school boat stay with zero hassles, you've found it.

House Boat

Authentic 40' Hatteras Yacht nBudget Keys Living & Ocean Views

Key West, Florida, United States

Bed

Bath

Sleeps

$310.58

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: 3 (1 king, 1 queen, 2 twins)brBathrooms: 3 (2 en suites)brLocation: New TownbrSquare Feet: 1651brParking: Driveway and street parkingbrAmenities: Wifi, TVs, in-unit laundry, office space, private pool, outdoor bar area, outdoor seating, outdoor grill, grass area to store a small boat up to 18 feetbrbrbrTHINGS 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.brbrPool heating is $100 per week and must be requested in advance

Margarita Villa-3 bedroom 3 bath home in prime location w/backyard pool oasis

Bed

Bath

Sleeps

$678.84

Discover this 3-bedroom boat in Key West. Step aboard and enjoy a gorgeous space featuring 2 queen beds and 1 twin bed, perfect for a group or family. With 2 bathrooms equipped with refreshing showers, guests can easily unwind after a day of adventure. The tranquil atmosphere invites you to relax and soak in the gentle sway of the water. Whether you’re lounging inside or taking in the views, this enchanting boat offers a unique and memorable stay. Our place will help you feel at home while you're traveling in Key West.brbrYour stay includes:br✔ Exclusive use of the yachtbr✔ Starlink Internetbr✔ Access to 2 pools, restaurants & shuttlebr✔ Snorkel gear + toys for excursionsbr✔ Spacious layout with 2 queen cabins, 1 twin, 2 bathrooms & outdoor showerbrbr Mandatory Excursion (Industry Standard)brbrGuests must book at least one excursion (2–24 hours). brbrExcursions are customized and priced per trip, not per person. brSeaJaz Excursion Rates (25% Below Competitors)brbr- 2-hour excursion: $975+ tax (no food included)brgratuity (15%-20%) paid at time of charter in cashbr- 4-hour excursion: $1300+ tax (Food and Chef Inc)brgratuity(15%-20%) paid at time of charter in cashbr- 6-hour excursion: $1700+ tax (Food and Chef Inc)brgratuity(15%-20%) paid at time of charter in cashbr- 8-hour excursion: $2000+ tax (Food and Chef Inc)br gratuity(15%-20%) paid at time of charter in cashbr- 24-hour excursion: $2800+ tax (Food and Chef Inc)brgratuity(15%-20%) paid at time of charter in cashbrbrPlease note that the cost of the excursions must be paid directly to our company at the time of booking. Any extra guests not staying on the boat added to the excursion we have a $100 extra guest fee added. The prices listed above include the captain's fee and fuel, however, does not include gratuity. Contact us directly to start planning your unforgettable day on the water.brbr Food & Dining (Important Clarification)brbr✔ Food + private chef INCLUDED during excursions of 4 hours or longerbr Not included on 2-hour excursionsbr Not included while the boat is docked overnightbr✔ Guests may cook or help cook in the galley anytimebr✔ Provisioning options availablebr✔ Alcohol not includedbrbrMake sure to inquire about our deep sea fishing and light tackle fishing charters, jet ski tours, golf cart rentals and all kinds of concierge services. brbr Gear & Toys Included (During Excursions)brSnorkel gearbrUnderwater scootersbrFloats & water toysbrFishing gear & bait (as appropriate)brCooler & icebrStarlink WiFibrbrExperiencesbrSnorkelingbrSailing lessonsbrSandbar tripsbrWildlife spottingbrSunset cruisesbrOvernight anchoringbrLearn-to-sail sessionsbrbrInside SeaJazbr2 Queen cabinsbr1 Twin cabinbr2 BathroomsbrLarge showerbrOutdoor showerbrSpacious cockpitbrSunny forward trampolines

House Boat

Dream Catamaran - 3 cabin with AC, large shower, beautiful views

Key West, Florida, United States

Bed