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Key West Vacation Rentals

We Have 1934 Vacation Rental Offers Available In Key West. Average Price Per Night Is $619.06. Find Your Vacation Home Today.

Showing 20 Of 1934 Vacation Rentals
  • Property-1 Image 1
    **SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE
    Condo $723 / Nightly
    • (11)
    • 1 Bed
    • 1 Baths
    Key West, Florida, United States

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrSERENITY ON SOUTHARD is a beautifully renovated 1 bedroom second floor condo with a full kitchen and washer and dryer. This condo is located in the Truman Annex, a gated community located in the heart of the island - just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have a peaceful retreat within a private gated community. Combined with Last Key Realty’s renowned Five-Star Guest Services, SERENITY ON SOUTHARD is an idyllic home base for your stay in paradise.brbrTHE LOCATION...brbrTruman Annex is a private, gated community right in Old Town, Key West. You'll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town, yet you'll benefit from the peace and quiet that Truman Annex is known for. Although you won't need a car to get around from this excellent location, there is a reserved off-street parking space.brbrTHE LIVING AREA...brbrThe living room of has a large set of French doors so you can enjoy those wonderful tropical breezes, and a large flat screen TV for those evenings when you need a break from the excitement of Old Town. The kitchen has everything you’ll need to prepare meals at home. Across from the kitchen is a versatile multi-level counter with bar seating and a work space with an office chair. You'll be able to dine outside on the sunny back deck using the outdoor dining set with seating for four.brbrTHE COMMUNITY POOL & FORT ZACHARY TAYLOR STATE PARK...brbrThe community pool is located just around the corner, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile from your front door. The entrance to Truman Annex is secured by a 24-hour staffed guard gate and you can use the residential entry gate keys to come and go on foot at night.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE ACCOMMODATIONS...brbr** Master Suite: King bed, flat screen TV, and access to the hall 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 TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchen (no dishwasher)br** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Assigned Off-street Parking for 1 Car (with vehicle restrictions - no vehicle over 18’ long or 80’’ wide)brbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 2 adultsbr** No Pets Allowed Read More

  • Property-2 Image 1
    SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
    Cottage $110 / Nightly
    • (1) Exceptional
    • 1 Bed
    • 1 Baths
    Key West, Florida, United States

    A QUIET BUNGALOW IN THE HISTORIC SEAPORT...brPrivate one bedroom home in the heart of Old Town.  A great place for a couple's getaway where you can live like a local.  Located in a serene setting off the main streets and surrounded by other "cigar" cottages.  A shared, heated, community pool is a great place to cool off or sit and enjoy a cocktail.brbrFURNISHINGS...brNewly decorated throughout with the feel of home.  Nicely equipped kitchen to cook your favorite meals.  There is a high top table with storage for wine glasses galore so our wine lover won't run out!  Flat screen tvs in both the living room and bedroom.  brbrSLEEPING ARRANGEMENTS.....brQueen bedroom just beyond the living area also has a separate entrance to the house for a quiet couple's hideaway.  Queen size pull out couch in the living room to accommodate your overnight guests.brbrDETAILS AND AMENITIES...brYou are next door to one of Key West's favorite diners, Harpoon Harry's.  You are just a across the street from the Historic Seaport with all of their quaint shops and restaurants.  Walk just down the street to and hop on a sunset cruise or water excursions! Explore the island and really get the feel for being a local. Youtube TV is provided for your enjoyment on lazy days inside. brbrPOOL AND OUTDOOR LIVING...brEnjoy the quiet and hidden community pool with lounge chairs to relax.  You have an outdoor patio area next to the cottage with a gas grill so you can dine alfresco. Pets are not considered at this home.brbr is not a pet-friendly home.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). brbrGREAT LOCATION! Read More

  • Property-3 Image 1
    Key West retreat - gated community, pool, washer/dryer, central AC - golf nearby
    Private Vacation Home $190 / Nightly
    • 2 Bed
    • 2 Baths
    Key West, Florida, United States

    Putting In ParadisebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis newly renovated townhouse is located in a lovely gated community in Key West, Florida. It is ideal for families, couples, and friends to come and spend some time together enjoying all the area has to offer. brbrGuests will love having access to amenities like multiple pools, a fitness center, butterfly garden, and a golf course so you can enjoy the best of nature during your stay. brbrThe house is fully-equipped with all modern appliances for your convenience. Put your feet up in the comfortable living room, read on the back deck in the breezy afternoon, and prepare meals together in the well-appointed kitchen. This home is a great getaway for all.brbrTHINGS TO KNOWbrGuests must use their own accounts to access streaming.brbrbrParking notes: Two parking spaces are available. brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the "Rental Agreement" on the checkout page.brbrbrCounty permit number: 25230-134973brCity/town permit number: LIC2022-001445brbrState/province tax number: 00072081-000289 Read More

  • Property-4 Image 1
    SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
    Private Vacation Home $675 / Nightly
    • 2 Bed
    • 2 Baths
    Key West, Florida, United States

    FLAWLESS SETTING, PERFECT LOCATION…brTucked away on a hidden lane right in the middle of Old Town, this luxurious private, single family home strikes just the right balance of Key West charm and South Beach flair.  Enjoy modern, open living space totaling two bedrooms and two bathrooms that extends into a spa-like outdoor area including a patio with flat screen TV, heated pool, outdoor shower, and a European grill.  Enjoy being steps away from the energy of downtown yet quickly escape to your own quiet, private oasis.brbrFURNISHINGS…brModern, stylish furnishings throughout with hints of local Key West décor.  Feel immediately relaxed just by stepping through the front door of this unique retreat.brbrSLEEPING ARRANGEMENTS…brQueen guest bedroom and full bathroom on the first floor.  Master king bedroom and full bathroom on the second floor. brbrDETAILS AND AMENITIES…brModern, chic decor pairs beautifully with the wood floors, vaulted ceilings, and rare Dade County pine.  Walk through the hallway to the kitchen, which is well equipped with stainless-steel appliances, a keurig coffee maker, breakfast bar, chic farm sink, and full-sized wine cooler.  Lounge in the living room furnished with a flat screen TV and comfortable stylish seating.  Open the fully retractable French doors to create a seamless, open-air extension to the cabana area; a beautiful private oasis that feels like you are in your own tropical resort.   Enjoy the private-heated pool, elegant seating areas, and lush landscaping.   brbrPOOL AND OUTDOOR LIVING…brLounge in the sun, float in the pool, or relax in the cabana with a cocktail.  Go for a night swim under the stars with the warm glow of poolside lanterns and adjustable mood lighting.  Add your own soundtrack with a wireless indoor and outdoor speaker system that you can control right from your mobile phone.  The cabana is equipped with an outdoor shower, a grill, dining table, flat screen TV, and couches for visiting, all which is surrounded by bamboo accents, tropical foliage and modern furniture.  Park your bike right outside the front door just like an island local with your own personal bike rack.  The perfect setting for your perfect getaway!  Stay in and indulge yourself in your own private oasis or hit the town with just a few steps - the ultimate stress-free vacation spot that you'll never want to leave.brbrPETS...brPets are provide size, age and breed prior-to or upon booking. 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). brbrLOCATION AND AMBIENCE…SPOIL YOURSELF! Read More

  • Property-5 Image 1
    2br-2ba Hyatt Key West Florida • Sleeps 6
    Condo $799 / Nightly
    • 2 Bed
    • 2 Baths
    Key West, Florida, United States

    Celebrate New Years at this beautiful waterfront Hyatt resort in Key West. Enjoy 7 Nights at this beautiful Hyatt Resort in Key West. Partial ocean views and lavish plantation-style decor welcome you to a two-bedroom condominium offering a master suite with king bed and adjoining bath with walk-in shower and jetted tub, and guest bedroom with queen bed and full bath. Amenities include full kitchen, dining area, living room with TV, furnished balcony featuring partial ocean views and wireless Internet.brbr(Resort Confirmation will be emailed to the buyer within 72 hours of purchase)brbr***ALL SALES ARE FINAL! **br**NON-REFUNDABLE & NON-TRANSFERABLE**brbrIndividual Resorts may require a credit card at check in for security deposit and/or incidentals. Buyer must be 18 or older. The resort may require a valid Photo ID for all guests. Seller is not responsible for fees charged by the resort such as required surcharges, parking, rollaway, beach service, occupancy tax (state of Florida), beverages, and meals. Read More

  • Property-6 Image 1
    Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
    Condo $550 / Nightly
    • 1 Bed
    • 1 Baths
    Key West, Florida, United States

    Hyatt Residence Club Key West Sunset Harbor brFantasy Fest 2022brLocation......Location, Location, Location....In the heart of everything!!brCheck-in Thursday, October 20t, 2022, 4:00 pm Check-out Sunday, October 23, 2022 10:00 am.brEnjoy the relaxed Key West lifestyle from a coveted location in the heart of Old Town. Perfectly situated on the western side of the island, this gracious retreat overlooks the Gulf of Mexico, offering magnificent water views. Outside your residence, take in the charms of Duval Street or the nightly sunset celebration at Mallory Square.brStudio apartment, king bed, living area, kitchenette with microwave, mini fridge & coffee maker.brAdditional $60 cleaning fee collected by resort upon departure. To be paid by renter. Read More

  • Property-7 Image 1
    Historic Apartment On The Waterfront
    Apartment $178 / Nightly
    • (2) Exceptional
    • 1 Bed
    • 1 Baths
    Key West, Florida, United States

    Newly renovated historic apartment in the heart of Key West. 10 foot ceilings and huge windows allow bright, natural light. Cherry hardwood floors throughout. The bedroom features a queen sized bed, closet, and armoire. In the living room, there is a futon option for overnight guests. New kitchen with modern stainless appliances and new bathroom includes full sized front loading washer/dryer. Private balcony with breakfast/dinner table overlooking William and Caroline St and the Historic Waterfront. High speed internet, HDTV with HBOGo, Netflix, cable, Blu-Ray and portable Bose Bluetooth speakers. There is a pool at Dantes, 1.5 blocks away (just need to buy a drink!). brbrAbout the Red DoorsbrThe original building was constructed in late 1868 as a real estate speculation by the Pinder and Curry Families of Key West. At first leased as a cigar factory to Cubans fleeing political turbulence in Havana, “The Doors” has been intimately connected with the Key West Waterfront for over a century. By 1906, with the shift of the cigar industry to Tampa, the Doors had become a ships chandlery. During the depression it was a grocery and hardware store serving both the neighborhood and commercial fishermen. br When shrimping gained real economic importance to Key West in the early 1950’s, the Doors, under a succession of colorful owners and names, became one of the toughest bars on the Gulf Coast. It was always a shrimpers bar and was known successively as the Conch Gardens, The Wagon Wheel Inn, and the Red Doors Inn. It was known informally as the Bucket of Blood. Here occurred many beatings, stabbings, assaults of various and colorfully imaginative sorts and, rumour has it, a number of quiet murders. With the gradual decline of the shrimp industry due to the depletion of the fishing grounds, inadequate conservation measures and growing foreign competition, the Bar itself became economically unviable and was closed in July 1972.br Architecturally, the original building was of typical Conch design, with commercial space open to the street on the ground floor and living quarters for the owners on the second floor. The building is only partially restored and still is burdened by the additions to the left side and rear put on during WWII to increase rentable space. The basic building is shaped with space for a garden in the rear. Architecturally or historically the Red Doors is one of the Key West Waterfront’s most picturesque landmarks.br Read More

  • Property-8 Image 1
    Cloud Suite On Duval - Luxury Condo with Sundeck!
    Apartment $575 / Nightly
    • (6) Exceptional
    • 2 Bed
    • 3 Baths
    Key West, Florida, United States

    Summary:brCloud Suite On Duval is a beautifully updated 2 bed, 2.5 bath upper level condo located in 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.brbrThe Space:brHistory 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. Not to be outdone, the living room also offers a comfy Queen-sized Murphy bed that can sleep 2 adults and a powder room under the stairwell.brbrThe downstairs living area offers all new furnishings and a large flat screen 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. brbrThe oversized updated kitchen includes bar seating and top-of-the-line stainless steel appliances to enjoy a home cooked meal and a large island counter top for prep.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit.brbrHow to access: This is a second-story home with stair access only.brbrThe Neighborhood:brOn the 700 block of Duval, The Cloud Suite on Duval is centralized to everything Key West. brIn 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.brbrLooking 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.brBeing 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!brbrGetting Around:brParking Information: This property does not offer parking: we are happy to provide you with nearby recommendations!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. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!brbrOther Things to Note:br- Just off the kitchen, and near the entrance of the home, is a new washer and dryer available for guest use.br- This unit is not pet friendly.br- This home is apart of the Sky Suites Retreat including 2 condo's above Duval Street, reserve both for a combined price up to 12 guests. Read More

  • Property-9 Image 1
    Flagler's Oasis by AvantStay| Private Pool in Key West | Month Long Stays Only
    Private Vacation Home $359 / Nightly
    • 2 Bed
    • 1 Baths
    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.brbrAvantStay provides an upscale experience with services that elevate your stay and save time so you can enjoy every moment. Guests have access to a 24/7 support team. Whether it’s fridge stocking or in-home massages, AvantStay offers a variety of upgrades & experiences to enhance your stay.brbr*Home Truths:*br- Pool heat is available for an additional fee but must be requested before your stay.br- Only dogs up to 40LBS are allowed, for 2 dogs the maximum weight can not exceed 20LBS for each. ???????Pets must be approved in advance and are subject to an additional fee of $150 per pet and a deposit of $300. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- All stays 28 days or longer will have a mandatory mid-stay clean that will be charged in the middle of your stay.br- The twin beds cannot be converted into a king bed.br- Our tropical island includes many creatures happily roaming around including geckos, lizards, chickens, iguanas, cats and ants. Most visitors enjoy watching our strange collection of animals!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 the check-out time for this home is 10 am.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---brbrAccidental Damage Protection: A non-refundable accidental damage protection plan has been included in the price of your reservation. Under this plan, you will not be held responsible to pay for accidental damage or loss to the rental property resulting from you or others in your party up to $2000. This plan does not cover intentional acts of a guest, gross negligence, or willful and wanton conduct, and/or damages caused by pets. This plan is not available for reservations 30 days or longer or reservations that require a security deposit.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. All bookings over 30 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud. Read More

  • Property-10 Image 1
    Caribbean Cottage- Duval St
    Cottage $531 / Nightly
    • (29) Excellent
    • 2 Bed
    • 2 Baths
    Key West, Florida, United States

    Imagine 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 twin daybed.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.brbrBedding Summary:brbrMaster bedroom - King size bed br2nd Bedroom- Queen size bedbrLiving Room - Twin daybedbrAmenities: Champagne for the newly weds! Private pool with bricked courtyard garden, fenced yard, fully equipped kitchen. A/C, washer / dryer, Flat screen color cable TV, C/D player and stereo, wireless internet. Linens and towels are provided.brbrActivities: 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.brbrArea: 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.brbrParking: Off-street parking for one car.brbrRestrictions: Smoke free house. No Pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrNote: 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. Read More

  • Property-11 Image 1
    **ISLAND INSPIRATION @ OLD TOWN** Elegant Home & Pool + LAST KEY SERVICES…
    Private Vacation Home $400 / Nightly
    • (1) Exceptional
    • 3 Bed
    • 4 Baths
    Key West, Florida, United States

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 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 Read More

  • Property-12 Image 1
    GARDEN HIDEAWAY ~ Beautiful lush landscaped oasis located in the Casa Marina
    Private Vacation Home $458 / Nightly
    • (4) Very Good
    • 4 Bed
    • 3 Baths
    Key West, Florida, United States

    PARADISE AWAITS...brThis charming home is located in one of the most desirable locations in Key West, the Casa Marina neighborhood. Garden Hideaway is situated on an oversized lot which is filled with lush foliage that creates a luxurious garden oasis. br brSLEEPING ARRANGEMENTS....brThere are four bedrooms in this sprawling home with a great layout that allows privacy. The spacious master bedroom is located on the main floor of the house. The master has windows lining the sleeping space as well as a French doors so you have wonderful views and access to the gardens and pool. There is a comfortable brand new king size bed and spacious bathroom en suite. The bathroom has all tiled surfaces including a shower with a glass block enclosure and a soaker tub. The next bedroom acts as as suite with two small adjoining bedrooms. An additional main floor room has a trundle bunk bed and a door that can separate both rooms for privacy. The other guest bedroom across the hall comes with a queen bed and leads out to the lush outdoor area by French doors. The fourth guest bedroom is located up the spiral staircase and comes with a queen size bed. There are two additional full bathrooms with showers on the first level of the home. All bedrooms with come brand TVs and brand new bedding.brbrAMENITIES....brStep through the French doors to an expansive entry way which leads you to the heart of the home. The large living room and dining area is open to the kitchen which makes this the perfect spot for entertaining. The living room has plenty of seating, a Sonos speaker system, smart flat screen TV as well as several windows with new window treatments overlooking the landscaped yard. Top notch dining furniture is available at the indoor table for 8 or out on the patio. The kitchen has brand new dishware, stainless appliances and is fully equipped for your convenience. Wood cabinets and granite countertops give the space a rich clean look. The home is glowing with recent updates to include new indoor and outdoor furnishings with gorgeous, upscale finishings.brbrOUTDOOR LIVING.....brLush, tropical landscaping with automatic evening lighting creates a private oasis that relaxes you once you step through the front gate. Stroll along one of the many brick pathways which travel throughout the property. Sit on one of the various decks, covered porches or seating areas with custom cushions, overlooking the gardens. Enjoy outdoor dining for 6 with your family for mealtime with the outdoor BBQ grill. Whether swimming in the private pool or lounging with a book, relaxation awaits. 4 bikes are available to enjoy a stroll through the streets of Key West.brbrPETS...brThis home is pet-friendly. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. 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).brbrISLAND TIME... Read More

  • Property-13 Image 1
    Casa Del Mar Dock & Ocean Access Key West
    Private Vacation Home $427 / Nightly
    • 3 Bed
    • 2 Baths
    Key West, Florida, United States

    This beautiful 2,300 sq ft home 3/2 Rare waterfront solid concrete block home located on Key West's Riviera canal with direct access to the gulf and ocean. Room for your boat on the 50 ft seawall, go to dinner by boat or just out for a cruise from the convenience of your back yard. The upstairs features an open floor plan with oversize kitchen, tons of natural lighting and endless palm tree views. The Home is fully equipped with kitchen needs, towels/beach towels, beach chairs, linens and more. The bedrooms are spacious and the master offers a nice sized walk in closet. Master room has a King bed and desk if needed for a work station. Bedroom #2 has 2 Queen beds and bedroom # 3 has 2 bunk beds (2 FULL Beds & 3 TWIN beds) The laundry is conveniently located upstairs. Step outside to enjoy your private backyard oasis with lush tropical landscaping. This home is designed for entertaining with over 600 sqft of covered outdoor living area, which hosts the large outdoor kitchen featuring granite counter tops. Downstairs you will find an 800 sqft game room with Foosball table, ping-pong table, basketball and More. We also have 3 bikes to use at your convenience to ride around town. This home is perfect to host families to build memories of a lifetime. Don't miss out on this rare opportunity to rent a waterfront home in Key West. Just a short 4 minute drive to the Famous Duval Street, Mallory Square, Key West Aquarium and more. Key west also has beautiful beaches Smathers Beach, Higgs Memorial Beach, our favorite Fort Zachary Taylor Historic State Park and more. So much to do in Key West from the best fishing, snorkeling/diving, jetskie and the list goes on. br6 Month Rentals Only Read More

  • Property-14 Image 1
    Craig & Cindy Key West Truman Annex Shipyard Condo w/ a patio at Mile Marker 0!
    Condo $272 / Nightly
    • (5) Exceptional
    • 2 Bed
    • 1 Baths
    Key West, Florida, United States

    Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes:brbr2 bedrooms 1 bath {queen and 2 twins (or we can convert to a king with a king converter at your request).brbrFully equipped kitchen with upgraded appliances and cooking accessories.brWasher & dryer with iron & ironing board.brAll towels and linens, including beach towels.brCentral air & ceiling fans.brFirst floor condo with outdoor decks & patios (or ask us about renting both an up and down Shipyard condo for even more room).brLarge shared Shipyard pool located just steps away.brFlat Panel TV's and entertainment center.brHigh speed internet with Wi-Fi.brAssigned parking spot for 1 car.brbrLocated in prestigious Truman Annex at Mile Marker 0 - location, location, location. Shipyard Condos are right at the entrance to Ft. Zachary Beach/Truman Waterfront Park and next to Mallory Square and those famous nightly Sunset Festivals and just two blocks from Duval Street and all of the shops, restaurants, night clubs and museums. While we provide a parking spot, you will not need a car! brbrExcept for festivals such as Fantasy Fest, Meeting of the Minds, and Powerboat Races, we generally require Saturday-Saturday rentals so if your dates are not Saturday-Saturday please email us with your dates prior to booking so that we can check our calendar to see if an exception is possible. brbrTo see our other VRBO Key West listings:brTruman Annex Shipyard Condo (2 bedroom 1 bath): #710793, #1435751, #2113538. #1384197, #3098421, #2158513 & #2161846.brTruman Annex Shipyard Condo (2 bedroom 2 bath): #984902.brTruman Annex Shipyard Penthouse (3 bedroom, 3 bath plus additional loft beds): #663368.brTruman Annex Foundry Townhouses (2 bedroom 2.5 bath): #966273 & #2161621.brTruman Annex Fleming House (2 bedroom 2.5 bath): #108809.brTruman Annex Porter House (4 bedroom 3 bath & private pool): #1092169. Read More

  • Property-15 Image 1
    The Most Perfect Old Town Key West Location for a Retreat!
    Private Vacation Home $752 / Nightly
    • (4) Exceptional
    • 4 Bed
    • 3 Baths
    Key West, Florida, United States

    The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny and bright, with beautiful furnishings and every amenity you could want. The bathrooms are conveniently located and can accommodate larger groups, and now have fabulous Japanese-style bidets. The gourmet kitchen is well equipped, and looks out (via large folding sliding glass doors) on a covered outdoor living space, with chaise and dining table. The pool is just steps further, surrounded by lush tropical plants. Sunbathing here or on the upper deck is a must. In the evening, the large upper deck has string lights- a perfect environment for drinks, dessert, or conversation. brbrThe house AC throughout, WiFi, and TVs with Apple TV in every bedroom. brbrIf you're looking for the real Key West experience, A Thousand Hidden Hemingways is the place. And if you wander around our neighborhood, you just might find some more like minded folks... Read More

  • Property-16 Image 1
    Gulf Getaway - Quiet Condo w/ Pool and Parking!
    Private Vacation Home $233 / Nightly
    • (3) Exceptional
    • 2 Bed
    • 3 Baths
    Key West, Florida, United States

    Summary:brConveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 bath perfect for your next island getaway. brbrIn addition to its prime location, this storybook corner unit features 2 private balconies off of each bedroom and a back deck equipped with all of your outdoor dining necessities. Close enough to everything, but just far enough away Gulf Getaway allows you to enjoy the peaceful serenity of Key West.brbrThe Space:brOn the second floor you will find the 2 bedrooms, each featuring a queen size bed, attached full bathroom and balcony. Perfect for accommodating 4-6 guests, additional sleeping arrangements can be found in the queen pullout couch on the first floor.brbrThe open first floor plan with a half bath is perfect for relaxing after a long day. Equipped with an LG cable tv, complimentary Wifi and French doors leading out to the back deck, the natural sunlight in Gulf Getaway keeps the space bright and airy. From an espresso maker, to a Keurig and smoothie maker, the rooster-themed kitchen is stocked with all of your cooking and drink necessities. There is also a hose outside for washing off sand from the beach and a private back entrance to make accessing the back patio a breeze.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit. brShared Community Features: This home also includes access to the neighborhood pool- exclusive to Truman Annex homes and has lounge chairs perfect for sunbathing. brHow to Access: the bedrooms are located on the second floor with stair access only.brbrThe Neighborhood:brExplore all that Key West has to offer including Truman Annex’s brand new Waterfront park and pier overlooking the Gulf. On Thursdays catch the sunset farmers market at the park or bring the kids to the splash pad for a fun-filled waterpark adventure. Just a 2 block stroll from the world-famous Duval Street, Gulf Getaway is walking distance to endless shopping and dining options.brbrGetting Around:brParking Information: There is assigned parking provided for 1 vehicle. We can provide you with recommendations for parking additional vehicles upon request.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. As this unit is located in downtown Key West, many attractions are within walking distance.brbrOther Things to Note:br- In the upstairs hall closet, you will find a stackable washer and dryer.br- Pets Policy: Pets are welcome!brOur requirements are as follows: br•30lb maximum per petbr•$15/night per petbr•2 pet maximumbr- This home has a 28-night minimumbr- Mid-stay cleans are available upon request. Read More

  • Property-17 Image 1
    Poolside townhouse in Key West Golf Club
    Private Vacation Home $165 / Nightly
    • (15) Wonderful
    • 2 Bed
    • 3 Baths
    Key West, Florida, United States

    Beautiful 2 bed/2.5 bath townhome in key west golf club. Pool steps away. Gated community. Enjoy everything beautiful Key West has to offer. Privately owned and operated. Get in touch to book your next getaway today! Read More

  • Property-18 Image 1
    Duval Duplex with free parking
    Private Vacation Home $375 / Nightly
    • 1 Bed
    • 1 Baths
    Key West, Florida, United States

    Come stay in paradise! Golf cart available for rent! We are perfectly located one block from Duval Street but in a tranquil and relaxing location. We are only 3 blocks from the beach, 3 blocks from an off site pool, a short walk to southernmost point, and right in the heart of Key West. Close to everything. The location can’t get any better! free parking! Newly renovated and comes with a king size bed, queen memory foam pull out sofa, and more! This is everything you need! 28 day stays available!brbrThe spacebrbrRelaxing Master Bedroom with a king size memory foam mattress and large closet. The Living room comes with a queen size memory foam mattress on a modern pull out sofa and also has a twin fold away bed. There is a full kitchen and dining area. Full size bathroom with shower, washer, dryer and two flat screen TV’s. Plus a nice patio with comfortable outdoor seating.brbrGuest accessbrbrThe entire residence is yours. Read More

  • Property-19 Image 1
    Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
    Villa $695 / Nightly
    • 3 Bed
    • 3 Baths
    Key West, Florida, United States

    • Luxury 2nd & 3rd floor Penthouse br• 3 Bedrooms with private porches & 2 1/2 Bathsbr• 2200 square feet of living spacebr• Over 2000 square feet of porches and decksbr• Backyard with tropical landscaping, pool & waterfallbr• Huge roof top sun deck overlooking Duval Streetbr• off-street parkingbrbrOne of a kind! Located in the heart of Old Town Key West on famous Duval St. just steps from restaurants, shops and theatres, this very unique Duval Street Luxury Residence offers a discerning traveler the best of Key West. brbrBrand new and beautiful, this sprawling two-story penthouse has three bedrooms, each with private terraces, a huge roof top sun deck overlooking the action of Duval St., and a private tropical garden with pool and gorgeous waterfall to relax by. brbrFine furnishings and art, top of the line Viking kitchen, fabulous bathrooms, and endless outdoor entertaining & sun worshiping areas make this a very special Key West retreat. brbrKeywords: Penthouse Read More

  • Property-20 Image 1
    THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
    Private Vacation Home $430 / Nightly
    • (2) Exceptional
    • 3 Bed
    • 3 Baths
    Key West, Florida, United States

    **Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additional credit card fees.brbrCLASSIC KEY WEST....brWhen only the best will do! The Seashell is the classic Old Town Key West home. Perfect setting for your dream island vacation. Located in Old Town and just steps away from the Historic Seaport.  You are in walking distance to some of Key West's best restaurants and boating adventures.brbrAMENITIES...brThis beautifully landscaped home with gracious sitting porch awaits you and your family. Newly renovated master king bedroom and bath are located on the main floor as well as a queen guest room with bath. A spacious great room that flows to the porches, pool and great outdoor space allows for family gatherings and hours of entertaining.  Updated kitchen looks over Sawyer Lane and opens to the pool area for easy outdoor dining.  Lovely Dade County Pine floors throughout and plenty of natural Key West sunshine from the many windows and doors. The second floor has a bonus room featuring a king, bath, office and rooftop sun deck. There is parking for up to two vehicles in gated driveway.brbrPETS...brThis home is not pet-friendly, however the owner may consider making exceptions for certain sizes/breeds. Please feel free to inquire in advance of booking.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). brbrLIVE THE CHARMED LIFE... Read More

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Information about vacation rentals in Key West

houseNumber of available properties in a Key West

1934 properties

pricePrices starting from

$1.00

petsNumber of properties with pets allowed

638 properties

spaNumber of properties with pool/spa

1654 properties

kidsNumber of Children welcome properties

1735 properties

beachNumber of properties near beach/ocean

834 properties

Key West Tourist guide :

What are the most popular tourist destination in a Key West ?

Located in the southernmost point of the United States, Key West is a beautiful island city surrounded by the clear blue waters of the Gulf of Mexico and the Atlantic Ocean. Known for its year-round tropical climate, laid-back vibes, beautiful architecture, and scenic landscapes, Key West is a popular tourist destination for travelers from all over the world.

If you are planning a trip to Key West, here are some of the most popular tourist spots you should not miss:

1. Mallory Square: Mallory Square is one of the most popular tourist spots in Key West, famous for its nightly Sunset Celebration. Here, you can enjoy live street performances, enjoy delicious food from local vendors, and witness one of the best sunsets in the world.

2. Duval Street: This mile-long street is the heart of Key West's entertainment and cultural scene. It is known for its vibrant nightlife, colorful street performers, delicious seafood restaurants, and many clothing stores.

3. Ernest Hemingway Home and Museum: Located on Whitehead Street, this museum is worth visiting for its beautiful Spanish Colonial architecture, lush gardens, and many artifacts belonging to the renowned writer Ernest Hemingway, who lived here from 1931 to 1940.

4. Key West Butterfly and Nature Conservatory: This indoor butterfly paradise is home to more than 50 species of exotic butterflies and tropical birds. The conservatory is an ideal place to take photos, learn about different butterfly species, and meet new friends.

5. Southernmost Point: The Southernmost Point is a famous landmark that marks the southernmost point of the United States. It features a concrete buoy that marks the location, and it is a common spot for photo-taking.

In conclusion, Key West is a fascinating destination, with so many exciting places waiting to be explored by visitors. Whether you crave a laid-back vacation or an action-packed one, the list above offers a guide to the most popular tourist spots in Key West, Florida.

What is the average price per night in Key West ?

If you're planning a trip to Key West, Florida, you may be wondering what the average price per night for a vacation rental is. Well, the answer is not so straightforward as it can vary widely depending on the type of rental, location, and time of year.

Generally, vacation rental prices in Key West can range from $100 to $1000 per night. For a budget-friendly option, you can find studio apartments and small cottages for around $100 to $200 per night, while larger houses with multiple bedrooms can cost up to $1000 per night. If you're looking to stay in a prime location, such as Old Town or near the beach, expect to pay more.

It's important to note that prices can also fluctuate depending on the time of year. Rates are usually higher during peak season (December to April) and holidays like Thanksgiving, Christmas, and New Year's Eve.

When searching for a vacation rental in Key West, it's best to browse multiple options and compare prices to find the best deal for your budget and preferences.

When is the best time to holiday in Key West ?

Key West, Florida is a popular destination for travelers seeking warm weather, sparkling waters, and a laid-back island lifestyle. With its tropical climate and unique culture, Key West is a great place to visit all year-round. However, there are certain times of the year when the weather is particularly welcoming, and tourists will experience the island at its best.

The best time to visit Key West is from December to May. During this time, the weather is milder, with an average temperature of 75°F, making it ideal for outdoor activities such as swimming, shopping, and exploring. Also, there are fewer crowds, less traffic, and a more relaxed atmosphere. January and February, in particular, are the driest months, making them ideal for escaping winter weather in other parts of the world.

Late summer and early fall are the times when Key West experiences hot weather, high humidity, and frequent thunderstorms. These conditions can make outdoor activities less enjoyable, but it’s also the time of year when hotel rates are cheaper as there are fewer tourists.

In conclusion, December to May are the best times to visit Key West for great weather, fewer crowds, and an enjoyable vacation experience. Be sure to pack sunscreen, comfortable clothing, and a willingness to unwind and enjoy the laid-back lifestyle of this beautiful island.

What are the most popular things to do in Key West ?

Key West, Florida is a paradise on earth, known for its crystal clear waters, white sandy beaches, and vibrant nightlife. A vacation in this exotic destination promises an unforgettable experience filled with endless fun, adventure, and relaxation. Here are some popular things to enjoy on your getaway to Key West.

One of the most popular activities in Key West is experiencing the amazing sunsets. Whether you are on a sunset sail, at the nightly sunset celebration at Mallory Square or the historic Key West Lighthouse, you won't be disappointed. Key West is also known for its world-class diving and snorkeling. There are several dive sites to explore, including the coral reefs, shipwrecks, and blue holes. You can either opt for a guided tour or snorkel on your own along the beaches.

If you love adventure, hiking or biking through the lush landscapes of Key West is a must-do activity. You can explore the island's diverse flora and fauna, wetlands, and spot some of the beautiful and exotic birds that migrate to the area. A trip to the Ernest Hemingway Home and Museum is also a must-see destination. It is the former home of the famous writer, and you can tour the house and garden, see the famously six-toed cats, and learn more about his writing and fascinating life.

Key West is also famous for its nightlife, dining, and entertainment. Take a stroll through Duval Street, the famous street filled with shops, bars, and restaurants that stretches from the Gulf of Mexico to the Atlantic Ocean. Sample the eclectic mix of cuisines, including the fresh seafood at any of the waterfront restaurants, or enjoy a poolside cocktail at one of the many luxurious hotels.

In conclusion, Key West offers a diverse array of activities to explore. Whether you want to relax and enjoy the sunsets, explore the island's natural beauty, learn more about history, or simply have fun with friends and family, there's something for everyone in this tropical paradise. Book your trip today and explore the magic of Key West for yourself.

Most popular vacation rentals in Key West

  • thumb
    $ 879.00 avg/night
    3
    • 4 Beds
    • 3 Baths
    • 7 Guest(s)
    Southard Love - 2.5 Blocks to Downtown, Walk to Beach. 4 Bedrooms, 3 Baths Key West, Florida, United States

    'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE LaneThis home is a perfect... Read More

  • thumb
    $ 640.00 avg/night
    36
    • 2 Beds
    • 2 Baths
    • 5 Guest(s)
    **PROMENADE TO PARADISE** Ocean Condo & Pool + LAST KEY SERVICES... Key West, Florida, United States

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your... Read More

  • thumb
    $ 199.00 avg/night
    1
    • 2 Beds
    • 2 Baths
    • 4 Guest(s)
    30 night minimum stay requirement. The Pearl in Paradise - 2 Bedroom House w Key West, Florida, United States

    Located on a quiet street in Key West, a tranquil residential neighborhood located just behind... Read More

  • thumb
    $ 772.00 avg/night
    8
    • 2 Beds
    • 3 Baths
    • 6 Guest(s)
    ~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex Key West, Florida, United States

    WEEKLY RENTAL: This property has a 7 night minimum stay.THE PROPERTY: Located where the Gulf... Read More

  • thumb
    $ 400.00 avg/night
    13
    • 1 Beds
    • 1 Baths
    • 4 Guest(s)
    Charming Studio with Shared Pool, Covered Patio - 1 Block to Shopping & Dining Key West, Florida, United States

    Papa's Hideaway #1 - Torrents of SpringOur calendar is updated in real-time & our nightly rates... Read More

  • thumb
    $ 881.00 avg/night
    5
    • 2 Beds
    • 3 Baths
    • 4 Guest(s)
    Stylish Condo with Swimming Pool - Minutes from Popular Attractions Key West, Florida, United States

    Truman's GardenOur calendar is updated in real-time & our nightly rates are accurately displayed.... Read More

  • thumb
    $ 412.00 avg/night
    3
    • 1 Beds
    • 1 Baths
    • 4 Guest(s)
    Bunk Room at Grand Maloney Hotel with Pool! Key West, Florida, United States

    Summary:The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key... Read More

  • thumb
    $ 234.00 avg/night
    1
    • 4 Beds
    • 2 Baths
    • 8 Guest(s)
    **BANYAN ROSE @ BEACHSIDE** Modern Home & Pool + LAST KEY SERVICES… Key West, Florida, United States

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your... Read More

  • thumb
    $ 1104.00 avg/night
    12
    • 2 Beds
    • 2 Baths
    • 6 Guest(s)
    ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool! Key West, Florida, United States

    YOUR SOUTHERN SANCTUARY...Find your serenity in this stylish and cheery townhome, just a short... Read More

  • thumb
    $ 566.00 avg/night
    2
    • 2 Beds
    • 3 Baths
    • 6 Guest(s)
    Grand Marina Suite- Stock Island Yacht Club Key West, Florida, United States

    Summary:A beautiful oceanfront suite located at the best marina in the Keys. Situated on the... Read More

 

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