Vacation Rentals By Owner In Key West, FL

RELAXED DOWNTOWN LIVING...brEnvelop yourself in true island living in this cute cottage just for the two of you. One of six homes in this exclusive compound located in the heart of Old Town. Located one block from Duval with charming porch and shared heated pool. Walk or stroll to dining, night life, galleries, shopping, and be at fabulous Ft. Zachary beach beach in minutes.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrFURNISHINGS...brCozy one queen bedroom and one bath. Great open floor plan with hardwood floors, plenty of Key West sunshine and blue skies through the large windows. Flat screens in the living and bedroom. Well stocked kitchen to use your culinary skills. Washer and dryer. Sofa sleeper in the living room is also available.brbrOUTSIDE LIVING...brBeautiful heated pool and waterfall. The pool and courtyard area is shared with five other homes, but it will feel like your own quiet piece of paradise with little to no traffic.brbrNEIGHBORHOOD ATTRACTIONS...brStroll through Bahama Village located in downtown Key West; aptly named because of it's many inhabitants that are of Bahamian decent. This lively neighborhood offers many popular restaurants such as Blue Heaven, Santiago's Bodega and La Creppiere. You can also find many small boutiques filled with treasures made by local artisans, some specialty wares and even antiques. Directly across from Hemingway's Home, Moon Dog restaurant and steps from the Southernmost Point.brbrPARKING...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.brbrPETS...brNo pets allowed.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). brbrINDULGE IN DOWNTOWN LIVING...

Cottage

PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!

Key West, Florida, United States

1

Bed

1

Bath

Sleeps

$326.31

Discover the charm of “Old Key West” aboard Vita Felice and embark on the journey of a lifetime by staying on a Luxurious Vintage Yacht and a piece of American History. This stay is paired with a Self Drive 20' Sun Tracker Pontoon Boat for Fishing/Lobstering, Cruising and Exploring the Sandbars. Enjoy local resturants with provided docks for the pontoon to enjoy night life. The location near downtown Key West is perfect for exploring the island on land but also provides a great opportunity to enjoy activities normally provided by boat charters. This unique opportunity gives you a secluded stay with a beautiful open water view unmatched by any other Key West lodging but also gives you freedom of water activities that would normally require a charter. Fishing, lobstering, and snorkeling are among many of the activities, including exploring on the Pontoon boat that can be used for island hopping and sandbars.brbrThis Yacht was “The first Hatteras” certified for charter and is anchored offshore Key West Island and it’s accessible with the paired Pontoon Boat. This elegant vessel offers a timeless escape into the Grandeur of the Past in True Old Key West Style. Experience authentic boating living in the ocean at anchor with a secluded tropical paradise on the water, WITHOUT neighbors in close proximity! Anchored just a short pontoon boat ride from land. brbrThe Pontoon rental for this boat is required and is the deposit for your nightly stay. Deposit is paid within 3 Days after you book your nightly stay. Pricing for the Pontoon is $250 per day depending on the length of your stay and is a bareboat rental that can be self drive or you can hire a captain to drive you and a list of captains can be provided.brbrExperience the Enchantment of Key West and unwind while Lobstering/Snorkeling, Swimming or Fishing, and Capture a Breathtaking Iconic Sunset at Sea!brbr#Provided Equipment (No extra charge):brSnorkeling GearbrLobstering Kits brbrThis yacht offers everything you could desire! Perfect for Catch, Clean & Cook videos to share with friends and family.brbr#2017 Sun Tracker DXL Fishin Barge Pontoon Boat brBareboat Rental (For Entire Stay)– Self Dive or Hire CaptainbrSpacious Deck with Comfortable Cushion 10 person seating and small tablebrIdeal for Fishing (fishing pole holders)brWater ladder for Snorkeling/LobsteringbrGarmin GPS for navigationbrBluetooth Sound for Smartphone brBimini Top for shadebrbr#1972 53' Hatteras MotoryachtbrAmenities On Deck! brSpacious Bow & Aft DeckbrBow Cushions for Lounging and SunbathingbrAft Deck Chairs & Couch for Entertaining brOutdoor Sink & Tables for Cooking & Cleaning your Catch , Inside full kitchen for cooking.brColor-changing led lightsbr brInside, Features Beautifully Preserved Original Mahogany Woodwork and Down Helm for Authentic Boating Experience and Pictures to Document and Share of Your Vacation.brbr#The Main Salon Includes:brBose sound bar system brSmart TV brWi-FibrColor-changing led lightsbrElectric CoolerbrDedicated A/C brTwo Convertible Couches Option into Two Twin Beds or a California King Bedbrbr#This Yacht comes Equipped with a Full Kitchen with Modern Home-Sized Appliances: brFull Sized Refrigerator brFull Sized 4 Burner Flat Range with OvenbrLarge Microwave brComplete Cookware and DishesbrToaster brTea KettlebrPantrybrbr#The Captain's Quarters Accommodations: brQueen Walk-Around Bed Nautical-Themed Bedding with Memory Foam ToppersbrTwo End Tables with Lampsbr32” Smart TVbrDedicated A/CbrAmple LightingbrFull ClosetbrEn Suite Full Private Bathroom Stocked with Fluffy Towels, Hair Dryers and Complimentary Toiletriesbrbr#The Guest Cabin: brTwo Single Beds with Nautical-Themed Bedding with Memory Foam ToppersbrFull ClosetbrDedicated A/CbrFull Guest Bathroom Stocked with Fluffy Towels, Hair Dryers and Complimentary Toiletriesbrbr#The V Berth includes: brBunk Beds with Nautical-Themed Bedding with Memory Foam ToppersbrDedicated A/CbrWasher/Dryer Combobr Linen Closet brExtended Shower Room with Vanity Stocked with Fluffy Towels, Hair Dryers and Complimentary ToiletriesbrbrVita Felice is Perfect for your next Special Occasion or Fun Getaway! brComplete with its Extensive Accommodations and Amenities! brbr#Spacious Timeless Classic Yacht for Events:brCelebration of Life/Memorial CeremonybrBachelor/Bachelorette PartiesbrProposalsbrHoneymoonbrBirthday Party'sbrOthersbrbrBE SAFE !brbr

Hatteras Sleeps 8 & SelfDrive 20' Pontoon Fishing Lobstering Snorkeling Sandbar

Key West, Florida, United States

Bed

Bath

Sleeps

$286.6

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 EXCEPTIONSbrbrFEATURES:brBedrooms: 2 (1 king, 1 queen, sofa sleeper recommended for children ONLY)brBathrooms: 2 brLocation: Sunrise SuitesbrSquare Feet: 798brParking: 2 parking spaces includedbrAmenities: Wifi, TVs, in-unit laundry, shared pool, close to beaches, private balconybrbrTHINGS 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.

Sunrise 308-2BR/2BA condo near beaches with pool, parking, balcony

Key West, Florida, United States

Bed

Bath

Sleeps

$294.31

This colorful three bedroom, two full bath, private, and historic home is just 2 blocks from world famous Duval Street! You will be just around the corner to The Hemingway House , famous Blue Heaven Restaurant and the Key West Lighthouse. brOur quiet lane starts on Petronia Street, which has become the culinary center of Key West. VIV wine bar, Le Creperie, Blue Heaven, Rams Head, & Santiago’sBodega are at the end of the road. Our location is simply perfect! Enter your desired dates and click Book Now! Read our 5-Star Reviews! (Please note: We have a 28 night MINIMUM stay. No exceptions can be made.)brbrOwners offer a marvelous home away experience. Three covered porches overlook a breezy tropical paradise with a unique shared 70' lazy river pool. TREETOPS has TWO floors of living. Perfect for your guests to join you in paradise. brbrAll furnishings have a cool, relaxed Key West vibe. The conch-style home was recently remodeled and meticulously furnished to a very high standard with ONLY Rave reviews from our guests. The pictures show accurately how well this SPOTLESS, colorful home SPARKLES. brbrTwo FREE bicycles come with the property and a parking spot option- not that you need it- Key West is a walker's paradise from your perfect location. brbrThe entire second floor is a Master Bedroom Suite with walk in shower, huge closet, and a private covered porch with views overlooking the Key West Lighthouse and our fabulous lazy river pool. Perfect spot for your morning coffee or a cocktail hour. Master suite also offers a private side staircase… easy access to pool. Outdoor teak and mahogany porch furniture, made from reclaimed boats, offers solitude and privacy up on the second level covered porch. Sliding glass doors on the second level overlook tropical grounds -See pictures! brbr Everything you need is right here... new appliances washer/dryer, linens, towels, gas grille on your private porch. brbrMany returning guests find TREETOPS to be their happy place. (Please note required minimum stays of 28 nights or longer. Due to Key West City transient licensing laws, many historic homes have a 28 night minimum to keep neighborhoods intact.)brbr* OASIS: Simply walk out the double glass doors to an amazing, one of a kind, 70' lagoon style shared pool. Adirondack chairs provided are perfect for reading or having a drink poolside. A Weber gas grille is located on your back porch for your use only. brbrThe spectacular common area backyard is lush and offers both sun and shade. Professional weekly landscapers and pool technicians keep the tropical gardens spotless. brbr* THE POOL: The unique 70' meandering salt water heated or cooled pool. The lagoon pool is shared with five cigar maker style homes. Spotless to swim in and gorgeous to look at, the evening pool and tree lighting is magical. brbrThe owners are very responsive to the needs of their guests and are always happy to answer your questions. Just ask! br________________________________________________________________________________br**TREETOPS is offered exclusively on VRBO. brBuyer Beware: Craigslist does not match owners to properties.

2027 calendar is now available! Old Town historic home Lagoon Pool 3BR ⭐️⭐️⭐️⭐️⭐️

Key West, Florida, United States

Bed

Bath

Sleeps

$160.47

This condo has a unique location in the Gated Truman Annex. It is very quiet, but yet very close to all Key West has to offer. brThe entrance road to the Ft Zachary Taylor St. Beach Park is right at the end of our block, for Lazy Days of snorkeling, swimming and sightseeing. The best sunset spot.brDuval St. is 2 blocks up, with shopping, restaurants and world class entertainment.brThe 2 porches, for privacy and sun options, also separates this from other properties.brWe also have a heated pool just across the courtyard.brThe 2 old town harbors, are also close by for all you ocean adventures, or just sightseeing.brbrbrKeywords: Key West, Truman Annex, 1/2 block from new Waterfront Park, Ft Zach Beach Access, Heated Pool, 2 porches, 2 bedrooms, washer/Dryer, dishwasher, 43' smart TV, 2 blocks to Duval and Mallory sq., 1 block to Green Parrot and Truman White House, Private Security, Parking, A/C, WiFi, Linens and cookware. Quiet.

Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach.

Key West, Florida, United States

Bed

1

Bath

Sleeps

$354.86

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to The Great Escape, a beautiful 3-bedroom waterfront retreat on Big Coppitt Key, just 10 minutes from downtown Key West! brbr brbrThis ground-level home combines the best of island living with the comfort and convenience you crave. Step outside and soak up the Florida Keys sunshine beside your private heated saltwater pool, where you can unwind with a drink in hand and take in breathtaking sunset views over the water. The outdoor living space is designed for relaxation and fun, complete with lounge seating, a pool house, and plenty of room to enjoy the tropical breeze. Inside, you’ll find a bright and inviting open layout with coastal-inspired décor, a fully equipped kitchen, and comfortable furnishings perfect for families or couples traveling together. Each bedroom offers a serene retreat after a day on the water or exploring nearby Key West. brbr brbrWhether you’re planning to fish, kayak, or simply relax by the pool, The Great Escape offers the perfect home base for your Keys adventure. Experience peaceful waterfront living just minutes from the restaurants, nightlife, and charm of Key West. brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2: Queen Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3: Queen Bed, Smart TV (no cable/satellite TV) brbr brbrLiving Room: Sectional Sofa, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 130' of Waterfront (shallow draft, only suitable for kayaks & SUP's) brbr brbr- Saltwater Heated Pool (heated to ~85 degrees Nov-Apr) brbr brbr- Pool House w/ Futon and Smart TV (no cable/satellite TV) brbr brbr- Propane BBQ Grill brbr brbr- Keurig, Drip Coffee Maker, Toaster, Blender brbr brbr- Outdoor Seating brbr brbr- Laundry brbr brbr- Parking for a maximum of 2 vehicles (including boat trailers) on the property. Recreational Vehicles may not be parked on the property. brbr brbr- Linen's and towels provided brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrNo Smoking: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrBoating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, three exterior security cameras monitor the property. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

The Great Escape: 3BR Waterfront Retreat, Heated Pool, Stunning Sunsets & Just Minutes to Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$703.13

br*Oceanfront Escape with Breathtaking Views – Steps from the Marina*brbrAwaken each morning to breathtaking sunrises stretching across the vast Atlantic, visible without even leaving the comfort of your bed. Nestled in tranquil Key West, this idyllic retreat boasts sweeping, uninterrupted ocean views and a private balcony that invites you to savor your morning coffee while soaking in the sights and sounds of nature. Watch graceful pelicans glide overhead, and enjoy peaceful moments of birdwatching as the day begins.brbr*THE Ideal Location for Adventure & Relaxation*brbrJust a short walk from a world-class marina, enjoy the vibrant energy of the island as fishing boats return with the day’s catch. Watch as captains clean their fish and feed the waiting tarpon—or join in! Hand-feed the tarpon yourself, pick up fresh seafood, and grill it poolside for a memorable meal under the palms.brbrLooking to get out on the water Book a charter with Captain Brad aboard Southpaw, a 43’ sportfishing boat renowned for unforgettable excursions.brbr*Unwind with Sunset Views & Local Flavors*brbrAs evening falls, wind down with a drink on the balcony while cruise ships glide into Key West Harbor and the sky lights up with sunset hues. Ready for dinner Take a short stroll to Yellowfin Bar & Grill for fresh-caught seafood and laid-back island vibes.brbr*Gorgeous 2-Bedroom, 2-Bath Stock Island Condo w/Private Pool & Hot Tub*brbrWhen you're ready to explore, downtown Key West is just 10 minutes away. Dive into activities like snorkeling, sunset cruises, or day trips to Dry Tortugas National Park. Don’t miss the famous Sunset Celebration at Mallory Square, where magicians, street performers, and live entertainment create a lively, memorable atmosphere that'll not fail to heighten your vacation experience.brbrVery welcoming, very clean, well stocked, and had a beautiful view. ~guest, Kim M.brbrOcean Memories Condo is located directly on the Atlantic with stunning ocean views from the kitchen, living room, master bedroom, and bathroom - as well as from the comfort of your own private balcony (a guest favorite)! The condo is furnished with comfortable, high-end furniture and impressive décor. The unit is fully equipped with state-of-the-art appliances, dishes, washer/dryer, and Wi-Fi. Approx. 1800 Sq. Ft. brbr**Be sure to check out our 5-star reviews**brbrNOTE: to see all photos use the and widgets abovebrbr***********************************************************br---- PARKING: Each unit comes with covered assigned parking.br---- GROUPS OF 5-6: This condo is best suited for groups of 4 or lessbr***********************************************************brbrbrbrkeywords: ocean's edge marina, condominium, condo, 2-bedroom, two-bedroom, two bedroom, oceanfront, key west, stock islandbrbr**Owner is available by phone 24 hours a day to answer any questions or address any concerns.**

OCEAN MEMORIES CONDO- 2 Bedroom, 2 Bath Oceanfront w/ Pool & Hot Tub

Key West, Florida, United States

Bed

Bath

Sleeps

$442.45

The condo is quite large at over 1150 square feet and looks directly at beautiful Smathers Beach. The 'Sea Jay' is located in La Brisa which is a gated community. It features a very large master bedroom with dressing room and a full bathroom. We look out at the beautiful Atlantic Ocean from the master bedroom, balcony and living room. Adjacent to the beach is Key West's longest sidewalk along the ocean for bike riding, jogging or walking. La Brisa has a heated pool, jacuzzi, sauna, clubhouse, lighted tennis court, three BBQ grills, picnic benches and covered Tiki huts. It is a quiet, family friendly location surrounded by tropical foliage. Consider us your 4 star luxury hotel suite but with the advantage of your own kitchen and a large second bedroom with another full bathroom. The condo has central A/C, cable TV in each room and a washer/dryer with all the conveniences of home in a secure setting. La Brisa is on the edge of old and new town in beautiful Key West.brbrbrKey West is easy to find and you can't get lost! Starting at the Miami International Airport or simply driving down from the north, you only need to get on U.S. Hwy. 1 and go south. The drive is just beautiful as the keys are linked by 42 bridges including the spectacular 7 mile bridge with outstanding water views all the way. The mile markers will tell you how far you have come.brbrKey West is located approximately 160 miles south of Miami and is about a 3 1/2 hour drive.brbrYou can also fly directly into Key West Airport and we are located only one mile away.brbrNOTE: No RV’s or Camping Trailers.

Key West Oceanfront Condo - 'The Sea Jay'

Key West, Florida, United States

Bed

Bath

Sleeps

$280.67

Summary:brbrCasa Azul is a luxe modern cottage with an open-concept living area that ends up filled with natural sunlight. Take a dip in the heated saltwater plunge pool with waterfall feature and night lighting. The best of Key West is at your fingertips - in Old Town only two blocks from Duval Street! Pet friendly, private parking & perfect for your next extended stay in Key West.brbrbrbrThe Space:brbrCasa Azul is the perfect mix of comfort and stylish. Sleek grey quartz countertops, stainless steel appliances and loads of storage space await you! Get ready to cook with state-of-the-art appliances where you can serve up your goods at the breakfast bar offering up a spot for morning coffee or switch on over to the six-top kitchen table. brbrbrbrBedroom 1: Queen bed brbrFeatures: Full bathroom with walk-in shower and plunge tub, private porch facing Elizabeth street, wardrobe, smart TV & closet.brbrbrbrBedroom 2: Full bed brbrFeatures: Modern full bathroom, smart TV, blackout shades & closet. brbrbrbrUnwind with high-speed wifi, a third full bathroom for guest use & an 80 inch TV for entertaining. Or sit in the sun loungers by the amazing pool to soak in the afternoon rays.brbrbrbrGuest 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 right in the middle of Old Town Key West and off of a quiet one-way street in a residential neighborhood. Great bikeable location. brbrbrbrJust two blocks from Duval street where you will be placed on the 600 block.brbrbrbrNearby Restaurants: Mangia Mangia, Onlywood Pizzeria, Miso Happy brbrbrbrWalking distance to famous bars, nightlife, and Key West Landmarks!brbrbrbrGetting Around:brbrParking for 1 vehicle 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- 28-night minimum rental onlybrbr- Private laundry roombrbr- Entire home is Solar powered with back up energybrbr- Pets welcomed

Casa Azul - Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$622.5

Summary:br- Centralized in the middle of Duval Street & walking distance to popular activities!br- Duval Square two bedroom two & half bath condo.br- On the intersection of Truman Avenue and Duval Street, just a 10 minute walk to downtown bars, restaurant and attractions.br- Off-street parking & rooftop pool access overlooking Duval Street.brbrThe Space:brVilla Positano features a private deck and open-concept kitchen perfect for entertaining and quality time with loved ones. brbrBedroom 1: Primary bedroom with king bed, vaulted ceilings, en suite bathroom and balcony.brBedroom 2: Queen bed with en suite bathroom.brExtra Sleeping: Queen sofa sleeper in the living area. brbrThe Duval Square complex is home to popular restaurants and shops. Located above you will find the small condo community featuring a rooftop pool and tropical landscaping.brbrGuest Access:brOur self check-in makes the process seamless. brbrGuests 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.brbrThe Neighborhood:brOn the 1000 Block of Duval Street located in Duval Square this second story condo is in close proximity all of your Key West favorites. Explore local restaurants directly below the complex, such as New York Pasta Garden and Origami Sushi or make your way to Duval Street for art galleries, more food, shopping and nightlife. Villa Positano is also walking distance to the Southernmost Point!brbrGetting Around:brOff-street parking provided for 1 vehicle.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi or by feet. This unit is located in downtown Key West and many attractions are within walking distance. Feel free to ask us for recommendations!brbrOther Things to Note:br-This unit features a private stackable washer/dryer.br- This unit is not pet friendly.br- Unit is located on the second floor with both stair & elevator access.

Gated Parking, Heated Pool - Villa Positano

Key West, Florida, United States

Bed

Bath

Sleeps

$1120.45

If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private waterfront pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor space. Slow down, relax and prepare for life the way it should be at Havana Daydream.brbrKey Features: br2 en'suite bedrooms each with porch accessbr4 full bathroomsbrbrLOCATION: This home is located in the gated community of Key Cove, on an exclusive lane of waterfront luxury homes. The perks of this little-known location are many: walking distance to the essentials such a grocery stores and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. The excitement of downtown Old Town is just a few minutes away by car, moped, or bicycle. This home includes plenty of off-street parking in the private garages, as well as private driveways.brLIVING AREA & KITCHEN: The main entrance to this home is at the top of the stairs leading from the ground level. This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with plush couches around a large HD flat screen Smart TV. One of the couches also pulls out to a Queen-sized sleeper sofa for additional guests. There is a dining table with seating for up to 8 diners, with additional seating at the kitchen bar. The gourmet kitchen has state-of-the-art appliances and is fully equipped with all of the tools and utensils one could want or need. The sliding glass doors open up to a wide waterfront deck with additional space for a light meal, coffee, a glass of wine, or just taking in the view. brACCOMMODATIONS: This home has two master suites, both of which are located on the top floor. The first master bedroom has a King size bed, a large flat-screen HD TV, and a beautiful two-room en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The first master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony, with gorgeous water views. The second master suite is down the opposite hallway, with a King size bed and an en-suite bathroom. The second master suite also has a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is beside the second master suite, with two twin beds that covert to 1 King upon request, flat screen TV. An additional bathroom is situated in the hall next to the stairs and across from the third bedroom. On the main floor there is a fourth bedroom with two twin beds that also convert to a King bed upon request. This bedroom also has a flat screen TV, and a full bathroom down the hall.brLANAI: Out back is the covered outdoor dining area comfortably seats six and has ample room for entertaining. With visiting heron on the tropical greenery that surround the back yard, your guest will enjoy the natural splendor Havana Daydream and Key West have to offer. Enjoy the brand new, kidney shaped, heated pool. The backyard is complete with a large propane grill. Additional space under the house also offers another covered indoor/outdoor area for playing, additional storage, etc.brbrDockage is not available at this home's development.brbrRATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).brbrDOG FRIENDLY. Please contact us to confirm specific pet policies.

Spacious Waterfront 4 Bedroom Home

Key West, Florida, United States

Bed

Bath

Sleeps

$626.94

Summary:br- Located on the quiet end of Duval Street steps from the Southernmost Point!br- Spacious two-story townhouse in Duval Square condominium complex.br- On the intersection of Truman Avenue and Duval Street, just a 10 minute walk to downtown bars, restaurants and attractions.br- Off-street parking & rooftop pool access overlooking Duval Street.brbrThe Space:brCasa Caribe features a private deck and open-concept kitchen perfect for entertaining and quality time with loved ones. brbrBedroom 1: Primary bedroom with king bed, vaulted ceilings, en suite bathroom and balcony.brBedroom 2: Queen bed with en suite bathroom.brExtra Sleeping: Queen sofa sleeper in the living area. brbrEnjoy the Duval Square complex home to restaurants and shops right on Duval street. A shared rooftop pool with lounge chairs is located on the rooftop.brbrGuest Access:brOur self check-in makes the process seamless. brbrGuests 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.brbrThe Neighborhood:brOn the 1000 Block of Duval Street located in Duval Square this second story condo is in close proximity all of your Key West favorites. Explore local restaurants directly below the complex, such as New York Pasta Garden and Origami Sushi or make your way to Duval Street for art galleries, more food, shopping and nightlife. Casa Caribe also walking distance to the Southernmost Point!brbrGetting Around:brOff-street parking for 1 vehicle included with your stay.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi or by feet. This unit is located in downtown Key West and many attractions are within walking distance. Feel free to ask us for recommendations!brbrOther Things to Note:br-This unit features a private stackable washer/dryer.br- This unit is not pet friendly.br- Unit is located on the second floor with both stair & elevator access.

Heated Rooftop Pool, Gated Parking - Casa Caribe

Key West, Florida, United States

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Bath

Sleeps

$639.75

brYou feel the excitement the moment you arrive. The warm tropical breezes, the blue green water. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Key West in a new and distinctive setting. We hope that you will enjoy staying directly on the ocean and enjoy the beautiful views and you will agree that Excitement has been found. Enjoy this upgraded two-bedroom, two-bath condominium with 1350 square feet of living space. Enjoy ocean views and the colors of the sunset from your private 35-foot balcony. brMaster bedroom has comfortable king-size bed; Second bedroom with Comfortable Queen & Twin . Queen sleeper sofa is in the living room Every room has high speed private WiFi. br Key West Luxury Living at it's best. Resort Swimming Pool , Bubbling hot tub, Sauna and Gym are complimentary for our guests Several picnic and barbecue areas surrounded by the native tropical gardens add to our guest options. Water sports, Snorkeling and the Coral Reef are all available at Smathers Beach which is steps away . EXCITEMENT ON THE KEY WEST OCEAN Our other VRBO Listings #4091149 & #154612brbrWE WILL BE TRANSITIONING OUR VRBO ACCOUNT TO ALL FLORIDA KEYS BASED IN KEY WEST. ALL BOOKINGS FROM JULY 1ST 2026 WILL GO THROUGH ALL FLORIDA KEYS. VRBO #20282915.

Penthouse Beach Ocean Views- Live the Dream

Key West, Florida, United States

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Bath

Sleeps

$623.01

Welcome to Casa Catalina – Your Key West Oasis!brbrStep into the enchanting world of Key West with a stay at the newly renovated Casa Catalina, a stunning historic Conch home that seamlessly blends timeless island charm with modern luxury. Nestled just half a block from Duval Street, this tropical retreat offers the perfect balance of tranquility and excitement, placing you mere moments from world-class dining, eclectic galleries, vibrant nightlife, and sun-soaked beaches.brbrA Spacious Retreat with Island ElegancebrbrCasa Catalina is larger than the typical cigar maker’s cottage, boasting an airy, open-concept design that invites relaxation from the moment you arrive. The living, dining, and kitchen areas flow effortlessly together, creating the perfect space for gathering with loved ones. High-end finishes, coastal-inspired decor, and abundant natural light set the tone for an unforgettable getaway.brbrNewly Designed Primary Suite – Your Private SanctuarybrbrUpstairs, discover a luxurious primary suite, a serene haven complete with a king-size bed, cozy sitting area, chest of drawers, spacious closet, and an en-suite bath. This thoughtfully designed retreat ensures ultimate comfort, offering a peaceful escape after a day of island adventures.brbrUnwind in the Ultimate Outdoor ParadisebrbrStep outside to a tropical backyard oasis, where a heated pool beckons for a refreshing dip, day or night. Whether you’re sipping cocktails at the outdoor bar, catching a game on the poolside TV, or dining al fresco beneath the swaying palms, this outdoor space is designed for endless relaxation and entertainment. Fire up the gas grill, rinse off under the outdoor shower, and soak up the perpetual sunshine of Key West.brbrPrime Location – Walk to Everything!brbrFrom Casa Catalina, you’re just a short stroll away from iconic Key West landmarks, including the Southernmost Point, Ernest Hemingway House, and pristine beaches. Indulge in the city’s best restaurants, boutique shops, and lively bars, all within easy reach. No car needed – simply step outside and embrace the island lifestyle!brbrAccommodations & AmenitiesbrbrSleeps 6 guests comfortablybrbrPrimary Suite (upstairs): King bed, sitting area, en-suite bathbrbrGuest Bedroom (downstairs): Queen bed, full bathbrbrAdditional Sleeping: Sofa converts to a queen bedbrbrFully equipped kitchen for culinary adventuresbrbrFree WiFi & cable TV with smart TVs throughoutbrbrCentral AC & ceiling fans for year-round comfortbrbrWasher & dryer for added conveniencebrbrAll linens provided, including plush beach towelsbrbrWeekly pool & yard maintenance (optional interim housekeeping available)brbrYour Key West Escape Awaits!brbrCasa Catalina is more than just a vacation rental—it’s a tropical sanctuary where memories are made. Pack light—just bring your shorts, swimsuits, and flip-flops—and immerse yourself in the laid-back luxury of island life.brbrBook your stay today and experience the magic of Key West at Casa Catalina!brbr(Owners are licensed Florida real estate brokers.)

Discover the lure of Casa Catalina, a blend of Key West charm and modern comfort

Key West, Florida, United States

Bed

Bath

Sleeps

$453.29

WONDERFUL WATERFRONT HOME ON GORGEOUS LOT...brYou have discovered a prime canal sanctuary second to none in the peaceful enclave of New Town. This fully renovated beauty offers a warm embrace with its welcoming open concept layout and airy cathedral ceilings, replete with a myriad of gathering spaces - indoors and out - for you and your vacationing crew! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brYour southernmost splendor begins as you enter this enchanting abode, spirits lifted as the Sonos sound system wafts through the home and pool area, instantly lulling you into island repose. The magnificent chef's kitchen inspires many hours in the happy pursuit of making memories as you entertain and craft epicurean works of deliciousness for an evening of consumption and conversation. The kitchen and ample dining table overlook a plush and expansive great room, complete with surrounding French doors leading to your outdoor retreat. Need to connect with the real world Not a problem as you have a full private office when duty calls. Enjoy a washer and dryer area adjacent to the kitchen for your ultimate convenience. Enjoy live streaming for binge-watching all of your favorite shows!brbrSLEEPING ARRANGEMENTS...brRelish in a perfect night of sleep in one of the 3 large bedrooms designed for ultimate comfort. The first guest room offers twin beds (can convert to a king upon request) and the second features a king bed. A full shower bathroom resides between the two guest rooms and there is also an additional full shower bathroom adjacent to the washer/dryer area off of the kitchen. The primary bedroom comes with a king bed and a large en suite shower bathroom. All of the bedrooms have private doors leading out to the backyard. A queen sofa sleeper resides in the living room. brbrOUTDOOR LIVING...brYour outdoor living oasis is an exquisite tropical dream come true. Enjoy multiple seating and lounging options, overlooking your large heated salt generated pool and waterfall (spa is not available for use). Tie the boat up (with 40 feet of sea wall available) from your fishing adventure and sit at your beautiful tiki bar with an outdoor kitchen that comes with an ice machine and a BBQ station.brbrPARKING...brThis home has plenty of off street parking for your vehicles. brbrPETS...brThis is 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!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.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). brbrCOME STAY A WHILE...

RISE AND SHINE ~ Canal Front 3 BR/3Ba Home w/ Heated Pool!

Key West, Florida, United States

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Bath

Sleeps

$243.16

Royal Oasis is a 550 sq ft apartment with queen sized sleep number bed and pull out couch. Full kitchen, washer/dryer, private entrance, pool access, outdoor seating area, central air, Roku tv and free Wi-Fi access.

Apartment

4 blocks from Duval and 7 blocks from the beach

Key West, Florida, United States

Bed

Bath

Sleeps

$626.48

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony.brbrEnjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more!brbrOn property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. brbrBeach supplies included: Coolers, Snorkel Gear and Beach Towels.brbrVisit this Key West paradise for a week or several, taking wonderful memories home with you!

Apartment

Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!

Key West, Florida, United States

Bed

Bath

Sleeps

$419.63

Welcome to Poseidon Too! A completely, newly renovated two bedroom two bath condo located at Sunrise Suites. Poseidon Too is located on the south side of Key West, and only about 1 mile away from Smathers Beach, and 5 miles away from downtown Duval St. Our condo is for guests that enjoy the finer things in life. The condo has just gone through a full renovation from top to bottom with only the best in mind. You will find high end furniture, a brand new kitchen/appliances, and amazing spa like bathrooms.brbrSleeping Arrangements:brMaster Bedroom - One king size bed with ensuite bath.brSecond Bedroom - One queen size bed with easy access to second bathroombrLiving Room - One queen size sleeper sofabr**All of our beds have excellent quality mattresses and come with high end bedding to give you a great nights sleep**brbrThe Space:brPoseidon Too is equipped with smart TV's in each room, high speed internet, central AC, new fully equipped kitchen with beautiful quartz countertops, new, in unit washer/dryer, and private balcony with amazing sunset views. brbrThings To Note:br- Guests will have full access to shared pool, hot tub, fitness room, tennis court.br- Sunrise Suites has elevator or stair accessbr- Parking - There are parking spaces on both sides of the building. all spaces are first come first serve. Please do not park under the building as these are reserved spots.br- Guests Access - will be contactless and you will be provided a code upon arrival.br- We can accommodate up to 6 guestsbr- Our condo is equipped with both a Keurig (with pods), and a drip pot.

Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites!

Key West, Florida, United States

Bed

Bath

Sleeps

$5626.59

Imagine escaping to a luxurious beachfront estate in the magnificent Florida Keys where you and your family, friends or colleagues can relax on a 120-foot private white sand beach or take a refreshing dip in a custom-built heated infinity pool with hot tub overlooking the Atlantic. Cassie’s Paradise, a four bedroom, four bath vacation retreat offers these experiences and so much more. You and your guests can go kayaking, paddle boarding or snorkeling right from the property’s private beach. The nature lovers in your group can walk to nearby nature trails and see wild Key deer and exotic birds in their natural habitat. And that’s just the beginning.brbrCassie’s Paradise offers all the amenities you would expect from a vacation retreat of this caliber: water views from every room, a well-appointed chef’s kitchen, a poolside wet bar and ice maker, a firepit, BBQ grill and beach essentials, including towels, an umbrella, beach blanket and snorkeling gear. Each of the four bedrooms has a king bed, and the home also has two queen pullout beds. For convenience, there are washers and dryers on the first and second floors, and for your peace of mind, the property is equipped with a security system. There’s even a mosquito control system that covers the entire grounds. And for those times when you still need to get some work done, there’s a private den and office where you can take care of business.brbrSomething else that makes this island vacation retreat truly unique is that it offers the best of both worlds: total seclusion and privacy when you want it, while the shopping, dining, bars and lively nightlife of Key West are just minutes away whenever you’re ready to experience them.brbrWith some advance notice, you can even arrange for the services of a personal concierge who will do everything in their power to make your stay as extraordinary as it can be. They can arrange for delivery of food and liquor, the services of a private, in-house chef or any catering or events needs you may have. They will also efficiently handle all types of reservations, whether you need transfers to and from the airport, a private shuttle to Key West, a spa, hair or nail appointment; laundry services or bookings for activities and excursions, including boat charters and scuba and snorkeling trips. How about having a couple of jet skis delivered right to the property’s private beach for your enjoyment They can do that, too. And when it’s time to dine, your concierge can get you into some of the area’s top restaurants, even those that others have trouble getting into. They will also be happy to use their connections to assist with your air travel needs.brMUST BE AT LEAST 25 YEARS OF AGE TO BOOK THIS HOUSEbrbrQuiet Hours 10:00PM-8:00AMbr brAll doors and windows must remain closed at all times. Keeping doors and windows open will over work the AC and not cool the house. Also many bugs can get inside.

Beach Front - Cassie`s Paradise Key West

Key West, Florida, United States

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