33040, Florida, United States Vacation Rental Homes By Owner - Page 101

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

Bed

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

Bed

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

Bed

Bath

Sleeps

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

Bed

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

Bed

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

Bed

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

Bed

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

Bed

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

Bath

5

Sleeps

$771.71

Welcome to Experience Key West Paradise at the Beach House Resort Retreat! ️brbrAdditional $500-$1000 SAVINGS available with on certain 7-Night stays, short stays or custom dates. brbrReservations at this property require owners to rent our units out in 7-Night increments from Sunday-Sunday ONLY. Stays that exceed the 7-Night deed may require a unit move.brbrPlease know, ★ provides stays shorter than 7-Nights but *may incur a higher nightly rate.brbrWelcome to your dream getaway at the Hyatt Vacation Club Beach House in stunning Key West! Unveil the magic of this premier residence club that boasts an irresistible combination of luxury, leisure, and beachside bliss.brbr ️ Private Beach & Dock Oasis brbrIndulge in the ultimate coastal escape with your very own private beach and dock area! Whether you're in the mood for soaking up the sun, taking a refreshing dip, or even embarking on a nautical adventure, the possibilities are endless.brbr Lagoon-Shaped Pool Paradise ‍♂️brbrDive into relaxation at our lagoon-shaped pool, where the fun is endless and entry is a breeze with the zero-entry design. No matter the time of year, the pool's wheelchair accessibility and year-round operation make it a watery wonderland for everyone to enjoy!brbr Sip, Savor, and Socialize ️brbrTantalize your taste buds with culinary delights at the bay-view grill restaurant, where the ocean's beauty meets delectable flavors. Unwind with a drink in hand at the lively bar, sharing laughs and stories that will create cherished memories.brbr Hot Tub Heaven brbrLet the bubbling waters of our hot tub melt your worries away as you gaze at the starlit skies above. It's the perfect place to find tranquility amidst the vibrant energy of Key West.brbr Luxurious Accommodations brbrUnwind in style in our lavish two-bedroom, two-bath units that can host up to six lucky guests. Whether you're traveling with family or friends, our spacious units provide unparalleled comfort and breathtaking views that will leave you in awe.brbr Convenience at Your Fingertips ️brbrOur front desk is at your service from 7:00 AM to 11:00 PM, ensuring your check-in experience is as smooth as the ocean breeze. Need to check in later No worries – simply reach out to us and we'll make arrangements just for you.brbr Easy Parking & Shuttle Services brbrPark your worries aside with our complimentary parking, and if you're flying in, take advantage of our airport shuttle (additional charge). Your journey to paradise is hassle-free from start to finish!brbr Stay Connected, Even in Paradise brbrFor those who can't completely escape work, our business center offers you the convenience of staying connected while surrounded by palm trees and ocean waves.brbr Explore Key West's Gems ️brbrNestled on the northeastern tip of Key West, our lush and landscaped retreat is your gateway to Mallory Square's legendary sunsets and the bustling streets of Duval. From shopping to dining and electrifying nightlife, the adventures await just minutes from your doorstep!brbrDon't just dream of a tropical getaway – live the dream at Hyatt Vacation Club Beach House. Your unforgettable Key West adventure starts here, where every moment is a memory waiting to be made. Book now and make waves in paradise! brbr Capture the MagicbrbrMake sure to snap photos of your amazing adventure and share them with us on social media using # . We can't wait to see the fun and excitement you experience at our resort haven!brbr Note: Images serve as representative depictions of potential resort units and amenities. Actual offerings may vary or have evolved since these snapshots were taken. Views, Features, furnishings, and amenities may differ from images. The floor plans are intended to provide a tantalizing glimpse of possibilities, not an exhaustive catalog. Your slice of paradise may vary, please inquire with your host!

Hotel Resort

Dream Getaway at the Beach House Resort+Amenities. 2BR

Key West, Florida, United States

Bed

Bath

Sleeps

$690.29

Key West Paradise Found is perched on the top floor with breathtaking Ocean Views, Reconfigured Master Bedroom and Remodeled Kitchen. If you have a larger party we also own the 2 units right next door so they can all be rented together. Enjoy your luxury condo with breathtaking view of the deep blue Ocean and sparkling salt water pool within our tropical garden.....There is nothing like it...anywhere.... at any price. Paradise Found is a TOP FLOOR spacious, clean and comfortable Key West condo experience. Enjoy your PRIVATE BALCONY for lounging sunbathing and dining.. This is a two bedroom two bath spacious condo. Newly renovated for 2020 and enhanced with Comfortable Beds. The Master has a KING. The second bedroom offers a QUEEN with an additional TWIN for sleeping flexibility. There is also a Queen sleeper sofa in the living room. brThis is Key West's most coveted location. Nestles between two of Key West's best beaches, Smathers Beach is just a 20 yard walk on the side walk. We are within 2 miles of most locations on the island. Enjoy the nightlife and excitement of Duval Street (restaurants, bars, live entertainment). Scuba Diving, Jet Skiing, Kayak Rentals, Deep-Sea Fishing, Cruises. Close to 18-Hole Golf Course, Moped/ Bicycle Rentals, Airplane/Seaplane Tours. We hope that you will enjoy staying on the ocean with all the comfort of home . After your first visit we hope you will agree.... Paradise has been found!brOur other VRBO Listings #4091146 & #4091149brbrCONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through the Spring of 2026. The building our units are in has been complete and we have new balconies. The work will be in the West building until Spring of 2026.

Panoramic Ocean: Beach from every window

Key West, Florida, United States

Bed

Bath

Sleeps

$212.63

This lovely Island Escape Condo is a upper level condo located in the prestigious Truman Annex. Not just another rental property! Location is everything.!!! Close to Duval.brStarting Jan 2026 , this beautiful condo will become monthly! Stays will have to be 28- 30 days. 10% discount for monthly rentals. Make plans to stay longer, relax or work remotely from paradise for a full month in 2026. br-Large private corner balconybr- Free High Speed Internetbr- Secure Parkingbr- Fully equipped kitchen with microwavebr- Washer and Dryerbr- Towels, Linens, Beach Chairsbr- Large community swimming pool for Shipyard residentsbr- Water park across the streetbr- Entertainment and cuisine in easy walking distancebr- Close to Fort Zachary park and Beach (Key West's most beautiful Beach)br- Just a few blocks to Mallory SquarebrbrbrOur favorite room is the spacious covered deck that opens up from living room with ceiling fans, tropical foliage, dining/sitting for 4.brThe Island Escape is a corner condo which allows for more privacy. The condo's parking stall is right at your front door and bike racks beside condo. Shipyard community pool is close and heated. Windows across the front of the condo let in lots of light and tropical breezes. No need for a car you can walk 2 blocks to Duval Street where you will find restaurants, shopping, night clubs and museums. Fort Zachary Beach is also close. You can rent kayak, canoe, or paddle board and launch on the beach. You can also picnic or grill in the park. Mallory Square where sunset is celebrated every night has local vendors and entertainment. Breakfast at Blue Heaven, visit Hemingway's House then have a drink and enjoy music at the infamous Green Parrot Bar. Visit the Historic Seaport District where you can watch boats, find great dining or catch a sunset cruise.brCheck out the Waterfront/Splash Park just behind the complex. Playground for kids, walk the pier at night to watch sunsets, entrance to Fort Zachary Beach and much more. You are close to everything!!! brThis condo is also our vacation home. We take pride in our condos and want our guests to relax and feel as if they are in their home away from home. br To see our other VRBO Key West listings:brTruman Annex Shipyard (2 bed, 1 bath) Conch Retreatvrbo.com/261681habrTruman Annex Shipyard (3 bed, 2 bath) Sea Breeze Cottage vrbo.com/987489ha

Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

Key West, Florida, United States

Bed

Bath

Sleeps

$469.2

Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry BuildingbrbrDiscover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.brbrProperty Highlights:brbrGated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.brbrOpen Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.brbrHalf Bath/Powder Room: Conveniently located off the kitchen.brbrMaster Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.brbrThird Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.brbrDesignated Parking: One assigned parking space located at the rear of the unit.brbrPrivate Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.brbrComplimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.brbrPrime Location:brJust steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!brbrBooking Notes:brbrHemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry BuildingbrbrDiscover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.brbrProperty Highlights:brbrGated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.brbrOpen Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.brbrHalf Bath/Powder Room: Conveniently located off the kitchen.brbrMaster Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.brbrThird Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.brbrDesignated Parking: One assigned parking space located at the rear of the unit.brbrPrivate Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.brbrComplimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.brbrPrime Location:brJust steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!brbrBooking Notes:brbrMinimum 7-night stay required between January 1 – April 30, 2020, with Saturday-to-Saturday check-in/check-out.brbrOutside this period, flexible arrival and departure days.brbrDiscounts available for stays of 28 nights or longer.brbrIf this property is booked, we can recommend other great homes in the area.brbrPack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!brbrOutside this period, flexible arrival and departure days.brbrDiscounts available for multiple months staysbrbrIf this property is booked, we can recommend other great homes in the area.brbrPack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!

Hemingway Hideaway in the Truman Annex

Key West, Florida, United States

Bed

Bath