Home Vacation Rentals By Owner In Key West, FL

Showing 60 Of 1997 Vacation Rentals
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Exceptional(73)

$764.15

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Private Vacation Home

Key West Caribbean Cottage - On Duval St w Private Pool

Key West, Florida, United States

bOverview/bbrbrImagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they`ll say hi to one another even if they`ve never met. This is your neighborhood during your stay at the Caribbean Cottage vacation rental. One of the best vacation rental locations on the island - without a doubt. Around the corner `Grand Vin` wine bar stands ready for an evening wine tasting session while `Flamingo Crossing` ice cream parlor offers up a new flavor of home made glace.brbrBrimming with genuine island charm, our Caribbean Cottage, with private pool, was originally built in the early 1900`s. Artistically renovated to maintain the original wood planked polished floors and vintage hand-hewed beams, the owners added bright blue tile (accented with marble), and Bahama style wooden window shutters tat compliment the historic interior. Original pine walls were painted with elegant historic colors of olive and cream and adorned the sash style windows and French linen curtains. Reserved for owner`s use only for many years, original artwork from their private collection is displayed throughout for you to enjoy.brbrThe living room is a generous cottage size with plenty of room to gather. On the side closest to the kitchen, a dining table is placed to create a roomy eating area. The adjoining `butler-pantry` style kitchen is spacious, has a charming French-Caribbean style ambiance, and is fully equipped and easy to cook in.brbrThe interior lay-out of this cottage maximizes privacy with the bedrooms and bathrooms on one side and common living areas on the other. The cottage has two full bedrooms and two full bathrooms.brbrBedding in this vintage cottage includes a king size bed in the master bedroom, and a queen size bed in the other. The master bedroom boasts a beautiful rich wooden armoire, and French doors lead from the bedroom to a pretty outdoor sitting area for reading and lounging. For extra sleeping, the living room has a comfortable queen sleeper sofa.brbrFrom the outside front, the cottage has charming curb appeal with a large beautiful Royal Poinciana tree and the Key West quintessential white picket fence, and of course the porch to sit and watch the world go by. The general design and layout of the cottage lends itself perfectly for versatile use. It is ideal for up to four, and can sleep up to five people comfortably.brbrIf you are looking for a truly authentic Key West experience, this cottage could be the perfect one for you. This charming property is located in the Upper-Duval Street historic neighborhood - a special section of Key West offering many up-scale attractions and interesting features including excellent gourmet restaurants, art galleries, boutiques, a high-end wine tasting store, an award winning home made ice cream shop, a coffee and tea house, South Beach around the corner, and .just a short walk to down to Mallory Square.brbrThere is off-street parking for one full size car, but from here you really never need to get in your car. Upper Duval Street is right out your front door, so forget the hassle of parking and enjoy walking or biking everywhere. Enjoy the island to the fullest, and then come home to relax in the pool.brbrbBedding Summary:/bbr - Master bedroom - King size bedbr - 2nd Bedroom- Queen size bedbr - Living Room - Queen sleeper sofabrbrbIMPORTANT: How payments work/bbrVRBO collects only their service fee. Reservation payments are paid directly to VHKW in two installments in accordance with the terms of your rental agreement (sent for review upon reservation). Payments to VHKW by credit card are subject to an additional 2.95% merchant processing fee.brbrbAmenities:/b Private pool with bricked courtyard garden, fenced yard, fully equipped kitchen. A/C, washer / dryer, smart TV, wifi. Linens and towels are provided.brbrbActivities:/b Shopping, restaurants, nightlife, museums, sailing, boating, snorkeling, diving, theatre, night life, family activities. Everything is within walking distance. Cafe neighborhood features art galleries, wonderful eateries and internationally famous fine restaurants, coffee house, fine gift and clothing stores. Right out your gate find Grand Vin Wine Bar, where you`ll enjoy a broad selection of wine by the glass and Flamingo Crossing, the award winning homemade ice cream store with some of the best ice cream you`ll ever eat. Key West South Beach is a 3 minute walk up the street at most Upper end of Duval St.brbrbArea:/b Upper Duval or `Uptown Key West` has evolved into the `elegant end of Duval` and offers an exceptional variety of restaurants, beautiful boutiques, and art galleries. Walk to South Beach in 3 minutes and the Southernmost Point of the United States is just down the street and around the corner. Walk to the Mallory Square Sunset Celebration in 15 to 20 minutes.brbrbParking:/b Off-street parking for one car.brbrbRestrictions:/b Smoke free house. No Pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrbNote:/b If you love this cottage but need to sleep more than 4 in beds, you can rent it with the one bedroom Vintage Luxury Cottage. You can combine a rental of both cottages and sleep 8 by renting the Fantasy Resort Villa. When rented together, you have two private swimming pools.
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Sleep 6

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Exceptional(22)

$743.07

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Apartment

Cloud Suite on Duval Street with Balcony

Key West, Florida, United States

Summary:brbrCloud Suite On Duval is a beautifully updated 2 bed, 2.5 bath upper level condo located right in the heart of world famous Duval Street! This stunning vacation home is located in the rear of the building and features a private sundeck with views of the surrounding tropical greenery. Take advantage of this rare find in the center of it all! Located on the 700 block of Duval Street, you are walking distance to nearly anything and everything.brbrbrbrThe Space:brbrHistory meets luxury in this 1935 home that has been redesigned and updated with a bright and modern touch. The 2 bedrooms upstairs both feature luxury King size beds with memory foam mattresses. Both bedrooms offer Smart TVs, ceiling fans, bedside lighting and gorgeous en suite bathrooms. The oversized windows allow ample natural lighting to fill your room every morning. The living room also offers a comfy Queen-sized Murphy bed that can sleep 2 adults and a powder room beneathe the stairwell.brbrbrbrThe downstairs living area offers all new furnishings and a large flatscreen Smart TV with plenty of seating for your entire group. Just off the living room and through the French doors awaits your private sundeck, the perfect place to start your day with a cup of coffee, or to end it with night cap after your late night activities on Duval St. brbrbrbrThe oversized updated kitchen includes bar seating and top-of-the-line stainless steel appliances to enjoy a home cooked meal.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit.brbrbrbrHow to access: This is a second-story home with stair access only.brbrbrbrThe Neighborhood:brbrOn the 700 block of Duval, The Cloud Suite on Duval is centralized to everything Key West. brbrbrbrIn the heart of Duval street you can find many of locals favorite's such as: Martins, 915, 801 Bourbon Street Pub, Moondog Cafe & The Hemingway House.brbrbrbrLooking for a night out Find Willy T's, Fogarty's and Fat Tuesday’s at the other end of Duval, but don’t worry there are pedicabs everywhere for easy transportation up and down Duval Street.brbrbrbrBeing in the heart of everything does come with noise of Duval street, but nonetheless an easy and convenient location to experience all Key West has to offer!brbrbrbrGetting Around:brbrParking Information: This property does not offer parking: we are happy to provide you with nearby recommendations!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. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Just off the kitchen, and near the entrance of the home, is a new private washer and dryer available for guest use.brbr- This unit is not pet friendly.brbr- This home is apart of the Sky Suites Retreat including 2 condo's above Duval Street. Reserve both for a discounted price, sleeping up to 12 guests. (Contact us for more information!)
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Sleep 6

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Exceptional(1)

$2433.36

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Hotel

Family Fun in Key West with 4 Pools & Free Shuttle! 2 Waterfront Units!

Key West, Florida, United States

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1525 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.
Bed 6

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Bath 6

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Exceptional(18)

$256.53

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Condo

Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool

Key West, Florida, United States

Welcome to Pierre's Perch, a beautiful second-floor studio that blends modern design with tropical charm! brbr brbrLocated in the historic Galleria, once a haven for Key West’s traveling artists, this tranquil oasis includes a peaceful pool area and a spacious sundeck perfect for unwinding. Nestled in the heart of Bahama Village, a vibrant, residential neighborhood just blocks from Duval Street, you’ll be surrounded by Bahamian-inspired charm and within walking distance to iconic attractions like the Southernmost Point, Key West Lighthouse, and the Earnest Hemingway Museum. Whether you’re here to relax, explore, or find inspiration, Pierre's Perch offers the perfect home base for your Key West adventure! brbr brbrSLEEPS MAXIMUM OF 2 GUESTS: brbr brbrBedroom: Queen Bed, Flat Screen TV brbr brbrKitchenette: Lightly Equipped (mini refrigerator/freezer, sink, two-burner stove, microwave and Keurig) brbr brbrAMENITIES: brbr brbr- Shared Heated (Nov-Apr) Pool brbr brbr- Shared Laundry brbr brbr- Shared Bike Rack brbr brbr- Shared Propane BBQ Grill brbr brbr- Keurig brbr brbr- Linen's and Bath/Beach Towels Provided brbr brbr- Street Parking available, no off-street/designated parking available brbr brbr- 2.5 blocks to Duval Street brbr brbr- 0.4 miles to Southernmost Point brbr brbr- 0.7 miles to Fort Zachary Taylor State Park/Beach brbr brbr- 1.1 miles to Mallory Square Sunset Pier brbr brbr- 1.2 miles to Key West Historic Seaport brbr brbr- 2.6 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrUnit Size: Please be aware, this unit is a cozy 115 sq. ft. studio—while compact, it provides all the essentials for a comfortable and enjoyable stay. brbr brbrAge and Occupancy Requirements: Booking tenant must be 25 years of age or older and must occupy the property for the entire duration of the booking. Furthermore, this property is exclusively available as a vacation rental and is not available for worker housing. brbr brbrNo Smoking: Smoking is strictly prohibited within the property to maintain a smoke-free environment for all guests. brbr brbrNo Pets: Pets are strictly prohibited within the property to maintain a pet-free environment for all guests. 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. brbr brbrSecurity Cameras: For the safety and security of guests and property, exterior security cameras monitor all exterior areas of the complex. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.
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Sleep 2

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Exceptional(1)

$450.85

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Cottage

Ann Street Gardens - Downtown Key West

Key West, Florida, United States

The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens offers the quintessential indoor/outdoor vacation experience you've come to the island to enjoy.brbrAnn Street Gardens is a 16+ compound. Regretfully, NO Children under 16 allowed. There is a coin operated Washer & Dryer on the south side of the cottage for use by the units in the compound. $1.00 per load, per machine, at time of writing.brbrThis residence has one bedroom, one full bath, a small kitchen, a living area, and a dining space. But first you'll want to open the doorway from the living room onto the delightful enclosed patio, which then opens to the main attraction-an exquisitely maintained poolside paradise. The shared, heated (in season) pool and landscaped garden area are reserved for the exclusive use of residents of the small enclave your cottage is part of. Chairs, small tables, chaise lounges, and wicker chairs around glass-top tables dot the landscape. Hidden in among the surroundings are more tables and chairs. From any spot you can observe sunshine playing through palm fronds creating a pattern of shadow and bright sparkle over the pool surface. If you look up, you're likely to spot a flock of water birds flying over. Swim, float, sit on the side, and dangle your feet in the refreshing water. Maybe relax in the sun to develop a tan. Or select the shade of a tree for your resting spot where your biggest decision might be whether to read or nap or ponder where you'll go for your next meal.brbrIf you're in the mood for total privacy, you can enjoy the same glorious Key West weather from your enclosed brick patio, part of which is covered and part open to the sky. This area is sizable, really like another room of the cottage, almost doubling the livable square footage. Closest to the house is a small round table with lamp and two chairs under a generous overhang. A little further, in an uncovered area, is a gas grille. Antique bricks under foot and artful arrangements of plants and vases enhance the garden atmosphere. Up two stairs brings you to the second covered area with vaulted ceiling where you'll find a table suitable for serving a meal for one to four. Directly across is a cushioned wicker rocker and large rattan sideboard with six drawers. Above, a Caribbean style ceiling fan with light creates a gentle air flow and illumination for the evening hours. This is definitely the spot where you could barbeque some fresh fish and enjoy it al fresco with a glass or two of chilled wine. Or maybe go out to dinner and return to the patio to spend a few balmy hours sipping cognac under a canopy of stars. brbrThe inside of Ann Street Gardens starts with the living area that includes a wall of glass overlooking the patio. This and other oversized windows throughout fill the cottage with lovely filtered sunlight and views of tropical greenery. The conversation setting includes a deep couch that also serves as a pull-out full bed, an ottoman that doubles as a coffee table, end tables with lamps, and an overstuffed armchair. The opposite wall holds a large flat-screen TV perfectly placed for viewing from the couch or chair. Under that is a brightly painted hutch that adds color, an artistic touch, and storage space. At the end of the room you'll find a small dining table and two chairs nicely placed beside a wall of glass that give you a congenial view as you enjoy a meal here.brbrNearby a doorway opens into the bedroom with queen bed flanked by bedside tables with lamps. Above the bed, a Casablanca-type ceiling fan provides air circulation and light. The room is embellished with art work, two windows, and wall mirror that reflects the romantic scene back onto itself. A flat-screen TV is nicely positioned on an opposite wall for watching the news or latest episode of Nurse Jackie from the bed. An armoire in one corner offers plenty of space for your hanging items and four drawers for folding items. Near the rear wall is the entrance to the en suite full bath, which features colorful tile flooring, shelving, and a well-lit mirror over the sink so you can easily check on your tan lines.brbrThe kitchen is small but perfectly functional with storage drawers, stove, refrigerator, microwave, toaster, coffeemaker, and blender. Again windows on two walls and a cloud white color scheme make this room light and airy and a pleasure to be in. brbrYour vacation accommodations are just the beginning-the whole of America's only Caribbean island awaits. Since Ann Street Gardens provides off-street parking, you'll find it ever so convenient to leave the car and walk or bike everywhere. For example the Historic Seaport and Boardwalk is over just one block. Follow the wooden walkway along the Key West Historic Seaport to find tall ships offering day and sunset cruises out into the Gulf of Mexico or take an all-day ferry excursion to the Dry Tortugas. If you're interested in watersports, you'll find diving, fishing, parasailing, snorkeling, and jet skiing close at hand. If you get hungry, a dozen or so restaurants of varying levels of informality ring the harbor. Maybe sit under a banyan tree filled with tiny white lights at funky Schooner Wharf while you eat a fresh Mahi sandwich, listen to local musicians, and gaze out at a harbor full of boats of all descriptions. Or for a higher vantage point, try the rooftop bar at Turtle Kraals. brbrFrom the Seaport, the world famous Duval Street with its tours, museums, shops, restaurants, and bars is only a block away. Before you walk too far, be sure to check your cell phone for sunset time so you don't miss the daily celebration at Mallory Square. And leave time to hang around for the after party as artists and street performers entertain the crowd with carnival acts, food, and drink. Maybe you've already heard about Dominique and his Flying House Cats, a feline troupe of alley cats that jumps through hoops of fire, walks tightropes, and performs other astounding circus feats.brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.
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Exceptional(3)

$288.45

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Private Vacation Home

Flagler's Oasis by AvantStay | Private Pool in Key West | Month Long Stays Only

Key West, Florida, United States

*This home is available for 28+ day stays only.*brbrBask in complete privacy in this Key West tropical paradise with a lagoon-style pool. This property is pet friendly.brbrFlagler's Oasis is a two-bedroom, recently renovated private home with a brand-new kitchen with granite countertops, stainless steel appliances, beautiful hardwood floors, and a serene setting.brbrAn open level of living space makes you feel like the indoors and outdoors are one giant room. Glass doors in both the master bedroom and the living room allow the sun to shine throughout the home and lets you enjoy the tranquil backyard and pool.brbrThe living area, with a sleeper sofa, flows elegantly into the kitchen and dining areas. The master bedroom has a king bed, while the second bedroom has two twin beds. There is a full bath just down the hall.brbrThe home features 3 flat-screen televisions equipped with YouTube Live Television, one in the living room, one in the second bedroom, and the third is outside under the Gazebo. The large 10 by 12-foot steel-roof gazebo is ideal for outdoor dining and entertaining while enjoying the tropical garden around.brbrThe outdoor space and pool are completely fenced in for privacy. There are lounge chairs for sunbathing and a table and chairs for additional seating and dining. The deep lagoon-style pool with an adjacent waterfall sitting pool is surrounded by a natural stone deck creating a sultry oasis.brbrThe property also has a huge 60-foot driveway that provides ample parking for several cars or even your boat and trailer.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- Pool heat is not available between 4/1 and 10/31.br- Pool heat is available for an additional fee but must be requested at least 48 hours before your stay.br- The twin beds cannot be converted into a king bed.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrPets:br- This home allows pets for a fee. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet. - Only dogs up to 40LBS are allowed, for 2 dogs the maximum weight can not exceed 20LBS for eachbr- We LOVE pets, however- Certain breeds typically have to have an additional owner or HOA approval. If your pet falls under any typical breed restrictions (breed, size, weight) please let us know so that we can confirm!br- Please note: This home has a stipulation on the pet policy. Only dogs up to 40LBS are allowed. If a guest is bringing 2 dogs then the maximum weight can not exceed 20LBS for each dog.brbrParking Details:brOff-street parking for 2-3 cars.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brBedroom 2 / Two twin bedsbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.
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Exceptional(2)

$445.0

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Private Vacation Home

**ISLAND INSPIRATION @ OLD TOWN** Elegant Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrIn the same way that the island of Key West has captured the hearts of so many, this charming monthly vacation home will capture yours. ISLAND INSPIRATION combines the appearance and charm of a historic Keys home, with all of the modern conveniences you have come to appreciate. This special home is situated on Margaret Street at the edge of where Old Town meets the highly desirable Casa Marina neighborhood. Located just a few blocks from both Duval Street and Higgs Beach, you couldn’t ask for a more ‘inspiring’ location. Best of all, ISLAND INSPIRATION includes Last Key Realty’s renowned Five-Star Guest Services, known for providing memorable Key West vacations. So leave your worries behind and let Key West’s island vibes be the inspiration you’ve been searching for.brbrTHE LOCATION…brbrImagine your vacation home being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the beach. Take a short stroll or bike ride down to the best of Key West, to hit local favorites like La Te Da, Louie’s Backyard, La Grignote, and El Siboney (which is only a few doors down the block). Just a few blocks towards the coast you'll find yourself at Higgs Beach and the White Street Pier. ISLAND INSPIRATION is a dream for beach-lovers who prefer to pack their coolers and towels and walk down to the sand and water. Watch the sunset from the White Street Pier just around the corner from Higgs Beach or grab a beach-side meal at Salute! On The Beach. Although you won’t need a vehicle to get around the island from this prime location, there is covered parking for two standard sized vehicles (larger vehicles will not fit) in the rear of the property.brbrTHE LIVING AREA...brbrFrom the moment you enter ISLAND INSPIRATION, you'll immediately notice the open and airy layout of the first floor. The living room has a large flat screen TV and plenty of comfortable seating options for everyone. The dining room table seats six and is located between the living room and the fully equipped kitchen. The kitchen has every tool and appliance you’ll need to prepare meals from home. There is also a convenient powder room located just off the living room.brbrTHE BACKYARD & POOL...brbrSlide open the large glass doors to step out and into your very own private backyard oasis. The private backyard is fully fenced and features mature island trees and lush tropical landscaping that provide maximum privacy. Between seating under the covered patio and chaise lounges on the pool deck, there’s plenty of room for everyone to spread out and relax in both the sun and shade. Taking a dip in the heated pool is the perfect way to relax after a long day of exploring Old Town. Treat your group to a poolside BBQ using the propane grill and outdoor dining table with seating for six.brbrTHE ACCOMMODATIONS...brbr** First Master Suite - Located on the Second Floor with a King bed, a flat screen TV, a closet, access to the front balcony, and an en-suite bathroom with a walk-in shower.brbr** Second Master Suite - Located on the Second Floor with a King bed, a flat screen TV, double closets, and an en-suite bathroom with a walk-in shower.brbr** Loft-Style Third Bedroom - Located on the Third Floor with 2 sets of Two Twin beds OR we can convert either/both sets into a King bed. This floor also has a separate sitting area with a sofa and a flat screen TV, and an en-suite bathroom with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room & All Bedroomsbr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Private Yardbr** Sleeper Sofabr** Private Heated Poolbr** Propane BBQ Grillbr** Covered Off-street Parking (with vehicle size restrictions)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 10 adultsbr** No Pets Allowed
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Sleep 10

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$260.21

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Private Vacation Home

Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beaches & Duval Street!

Key West, Florida, United States

City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Vahevala, your charming Mid Town Key West retreat! brbr brbrThis private home is your oasis, boasting a refreshing pool and an ideal proximity to both pristine beaches and the vibrant Duval Street. At Vahevala, you'll find the perfect blend of relaxation and excitement. Unwind and savor the moment by the pool, cocktail in hand, as you soak up the sun and tranquility of your ultimate relaxation retreat. Indulge in relaxation on the nearby Smathers Beach, embrace the charm of a leisurely stroll along Duval Street, and capture memories with a selfie at the iconic Southernmost Point. Your Key West getaway at Vahevala is ready to make your dreams of sun, fun, and relaxation a reality. brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: Queen Bed brbr brbrBedroom 2: Queen Bed brbr brbrBedroom 3: Murphy Wall Bed (Full Size) brbr brbrFamily Room: Sofa, Smart TV brbr brbrLiving Room: Sofa, Chair brbr brbrKitchen: Nicely Equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Private Pool (heated to ~85 degrees Nov-Apr) brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Off Street Driveway Parking for 1 Vehicle brbr brbr- Linens and towels provided brbr brbr- 0.5 miles to Higgs Beach/White Street Pier brbr brbr- 1.0 miles to Smathers Beach brbr brbr- 1.2 miles to Upper Duval Street brbr brbr- 1.3 miles to Southernmost Point brbr brbr- 1.9 miles to Key West Historic Seaport brbr brbr- 2.2 miles to Lower Duval Street brbr brbr- 2.3 miles to Fort Zachary Taylor State Park Beach brbr brbr- 2.4 miles to Mallory Square Sunset Pier brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited on premises 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. brbr brbrSecurity Cameras: For the safety and security of our guests and property, two exterior security cameras monitor the front door and carport. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.
Bed 3

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Exceptional(1)

$345.76

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Private Vacation Home

LONE PALM COTTAGE ~ 3 BR, 2.5 Ba Home w/ 2 Cottages, Pool & Parking!

Key West, Florida, United States

OLD TOWN AMBIENCE....brLuxury Old Town Key West Monthly Rental – Private Heated Pool, Quiet Lane, Off-Street Parking, Sleeps 4-6 – 28-Night Minimum Stay. Nestled on one of Old Town Key West’s most peaceful lanes, Lone Palm Cottage captures the essence of Key West living with refined comfort and privacy. Lush tropical garden views, swaying palms, and a charming porch with graceful scrollwork set the tone for this private Old Town home. The property includes a main house and two guest cabanas, offering separate sleeping quarters and complete privacy — perfect for discerning guests or extended stays. At its heart lies a 12’ x 18’ saltwater pool with a soothing fountain, surrounded by orchids and palms. Inside, historic Dade Pine craftsmanship meets modern luxury, featuring a chef’s kitchen with Wüsthof, Le Creuset, and Revere cookware, a high-speed Fiber Optic Wi-Fi workspace, and an on-premises washer and dryer. Just a short walk to Duval Street, fine dining, and the seaport, Lone Palm Cottage delivers authentic Key West charm and boutique exclusivity — a serene retreat for travelers seeking privacy, sophistication, and a genuine connection to the island’s timeless allure. There is a Ring doorbell located on the front door of this home for security purposes.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES....brInside, the airy living space welcomes you with vaulted ceilings, classic Dade Pine walls, and sunlit windows that create an atmosphere of relaxed sophistication. French doors open to the outdoor terrace, blurring the line between indoor comfort and open-air leisure. The chef’s kitchen, appointed with Wüsthof, Le Creuset, and Revere cookware, offers both beauty and function — complete with a pass-through for effortless entertaining or alfresco dining. Designed with balance and flow in mind, Lone Palm Cottage combines historic craftsmanship with modern elegance, creating a calm, inviting environment that reflects the best of Key West living.brbrSLEEPING ARRANGEMENTS...brLone Palm Cottage is designed to provide both comfort and privacy, making it ideal for couples, extended families, or guests traveling together who appreciate their own space. The primary suite in the main house features a queen bed, an en-suite bath with a double-entry shower, and a dedicated workspace with high-speed Fiber Optic Wi-Fi, perfect for quiet mornings or catching up on work in comfort. Each of the two guest cabanas offers a queen bed and private entrance, creating a boutique-style experience that allows everyone to unwind at their own pace. One cabana includes a full bath, while the other features a half bath with a vanity sink, offering flexibility without sacrificing elegance. Thoughtfully arranged around the garden and pool area, these accommodations blend Old Town charm with modern sophistication, ensuring every guest enjoys a restful and rejuvenating stay.brbrOUTDOOR LIVING...brOutdoors, Lone Palm Cottage transforms into a private retreat designed for relaxation and indulgence. The saltwater pool, which can be heated or cooled depending on the season, is surrounded by lush palms and orchids that sway softly in the tropical breeze. After a refreshing swim or an afternoon in the sun, the outdoor shower offers a secluded, open-air escape — a refreshing, sensory experience that captures the essence of Key West living. The dining terrace and lounge area invite unhurried evenings for conversation, dinner, or quiet moments beneath the stars. Two beach cruiser bicycles are provided for leisurely rides through Old Town’s charming streets and waterfront paths — a signature pleasure of Key West living. Every element of this outdoor space is crafted to extend the home’s quiet sophistication and timeless charm into the open air — an intimate setting where comfort meets understated elegance.brbrPETS...brThis is not a pet-friendly home.brbrPARKING...brThis home offers off street parking for 1 vehicle.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. 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).brbrPRISTINE PRIVACY IN PARADISE...
Bed 3

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Bath 2

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Exceptional(1)

$4412.19

/ Nightly
Private Vacation Home

**A ROYAL AFFAIR @ DUVAL** Three Home Compound + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrFinding high-end accommodations for a large group vacation can be a challenge... let Last Key Realty make it easy for you with this one-of-a-kind compound. A ROYAL AFFAIR is the combination of three homes that offer everything a large group could desire in a Key West vacation home - a total of eleven bedrooms, twelve full bathrooms, three open living areas, two private pools, a hot tub, three fully equipped kitchens, three off-street parking spaces, and a superb downtown location that allows for easy access to the best of Old Town Key West. The cherry on top of your luxury stay at A ROYAL AFFAIR is Last Key Realty's Five-Star Guest Services & Complimentary Concierge, ensuring you’ll receive 'the royal treatment’ throughout your Key West vacation.brbrTHE LOCATION…brbrIf you decide to pull yourself away from these beautiful homes, you’ll realize that the best Key West restaurants, live entertainment, and attractions are all within a few blocks of your front door. While you won’t need a car to get around from this fabulous location, there are three off-street parking spaces in the driveways. If you don’t have vehicles but want to explore the island in a fun way, Last Key Realty’s concierge service can assist with golf carts, scooters or bike rentals.brbrTHE LIVING AREAS...brbrThere are a total of three living areas, each with plenty of space for everyone to unwind after a day on Duval Street or out on the water. Each living room features a large flat screen TV that can be enjoyed from the comfortable furniture options, including plush sleeper sofas in each house. The three kitchens are fully equipped with every appliance and tool the chef in your group will need to prepare meals from home. Each home also offers indoor and outdoor dining.brbrTHE PRIVATE POOLS & HOT TUB...brbrAll three backyards are connected via open gates that allow your crew to pass through and mingle amongst the homes. Two of the backyards have pools, which can be heated to your liking in the cooler months, and the third home has an oversized hot tub when you’re ready to enjoy a soak. Comfortable chaise lounges and patio furniture on the decks offer an array of outdoor lounging and seating options. Each home has an outdoor dining set and a propane grill when you want to bring the group together for happy hour or a poolside BBQ.brbrTHE ACCOMMODATIONS...brbrThis compound will keep your whole group satisfied, with ample space for everyone to escape to their own accommodations.brbrHouse 1 has 5 bedrooms + Media Room:brbr** 1 King - First Floorbrbr** 2 Twins or 1 King - First Floorbrbr** 2 Twins or 1 King - Second Floorbrbr** 2 Twins or 1 King - Second Floorbrbr** 1 King & 1 Daybed - Second Floorbrbr** 2 Sleeper Sofas – 1 in the Media Room and 1 in the Living RoombrbrHouse 2 has 2 bedrooms:brbr** 1 King - First Floorbrbr** 2 Twins or 1 King & 1 Daybed - Second Floorbrbr** 1 Sleeper Sofa – Living RoombrbrHouse 3 has 4 bedrooms + Media Room:brbr** 1 King - First Floorbrbr** 1 King - First Floorbrbr** 2 Twins or 1 King - First Floorbrbr** 2 Twins or 1 King - First Floorbrbr** 1 Sleeper Sofas –Media RoombrbrFor rooms with two twin beds that can convert to a King, we ask that you communicate to us at least one week prior to arrival with these requests.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen HD 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 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** 3 Fenced & Lushly Landscaped Backyards br** 2 Private Pools with available Pool Heatbr** 1 Hot Tubbr** 3 Propane BBQ Grillsbr** 4 Queen Sleeper Sofas + 2 Daybedsbr** 3 Off-Street Parking Spaces (with restrictions - NO LARGE VEHICLES)brbrOther notes:brbr** In person welcome br** Interim housekeeping provided upon requestbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** This property will accommodate up to 34 adultsbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
Bed 14

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Bath 12

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