Home Vacation Rentals By Owner In Key West, FL

Showing 1600 Of 2059 Vacation Rentals
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Exceptional(26)

$329.49

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Private Vacation Home

Conch Get Enough at The Truman Annex in Key West

Key West, Florida, United States

Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild rooster. After a morning stroll, you are ready to enjoy an alfresco breakfast that was just created in your new kitchen. Sit back, relax, you are now on Key West time!brThis 2 bedroom 2.5 bath townhouse is prepared to meet your vacation needs. Upstairs you will find two bedrooms each with ensuite baths, and queen beds. Each room also boasts French doors leading to private balconies, allowing fresh breezes in. There are ceiling fans and TV’s in each bedroom.brThe open first floor plan with half bath and comfortable décor lends well to the casual lifestyle of Key West. Your newly renovated kitchen with stainless-steel appliances and Quartz countertops seamlessly flows to the dining and living areas allowing you to enjoy the well outfitted kitchen while entertaining friends, sipping your favorite beverages, and enjoying good conversations. Double French doors draw you out to the private lush tropical garden and deck.brA few steps outside the fence you will find the President’s Walk Association heated swimming pool. This beautiful gem is a short walk to Key West’s best beach (Fort Zachary Taylor) and the Truman Water front park. You are three blocks to the sunset celebration at Mallory Square, and two blocks to the famous Duval Street where restaurants and entertainment are plentiful.brWe can’t get enough of it and we hope you feel the same too after visiting.brThank you for your interest in our tropical retreat. brCheers!brbrPlease note: This property is monthly rental - This property has a 28 night minimum stay
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$323.73

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Private Vacation Home

OCEAN BREEZE BUNGALOW-Stunning 2 Bedroom / 2.5 Bathroom in Truman Annex

Key West, Florida, United States

Welcome to Ocean Breeze Bungalow – Your Luxurious Key West RetreatbrbrEscape to paradise in this stunning 2-bedroom, 2.5-bathroom bungalow nestled in the prestigious Truman Annex. Perfectly blending elegance, comfort, and convenience, Ocean Breeze Bungalow offers an exceptional vacation experience for families, couples, or friends seeking a serene yet vibrant Key West getaway.brbrWhy You’ll Love Ocean Breeze Bungalow:brbrThoughtfully Designed Living SpacesbrStep inside this beautifully renovated home and feel immediately at ease. The open-concept first floor features a gourmet kitchen equipped with high-end appliances, perfect for crafting delicious meals. Enjoy casual dining at the breakfast bar or gather in the sunlit living and dining areas, where comfort meets style.brbrPrivate Outdoor OasisbrThrough the living room, step out onto a fully enclosed, private back patio — your ideal spot for outdoor dining, grilling, or simply soaking up the Florida sunshine. The courtyard offers complete privacy and includes a refreshing outdoor shower for rinsing off after beach days.brbrRestful Bedrooms with Privacy and ComfortbrUpstairs, unwind in the spacious primary suite featuring a king-size bed, built-in cabinetry, and a private lanai to enjoy your morning coffee or evening breeze. The attached bathroom boasts a large walk-in shower and ample vanity space. The second bedroom offers a cozy queen bed and an en-suite bathroom filled with natural light.brbrExplore Key West with EasebrLocated in the exclusive Presidents Walk neighborhood of Truman Annex, this home is just a short stroll to the Truman Waterfront Park and less than three blocks from the lively Duval Street. Discover world-class dining, vibrant nightlife, art galleries, shopping, and live music—all within easy walking distance. Plus, two cruiser bikes are included for your adventures!brbrRelax and RefreshbrEnjoy access to the communal pool, heated during the cooler months (December–April), complete with comfortable chairs and loungers—perfect for unwinding after a day of sightseeing.brbrConvenient AmenitiesbrA designated parking space is provided, making your arrival and stay hassle-free. Additional features include an outdoor gas BBQ, a powder room on the main floor, and fast Wi-Fi throughout the home.brbrAdditional Details:brbrSleeping Arrangements: 1 King Bed, 1 Queen Bed, and 1 Sofa SleeperbrbrParking: Designated spot includedbrbrPool: Heated communal pool (winter months) with loungersbrbrExtras: Private outdoor shower, two cruiser bikes, outdoor gas BBQbrbrRental Terms: Weekly rentals through 2025; monthly rentals from January 2026 onwardbrbrGuest Policy: Primary traveler must be 28+ and present throughout the staybrbrPet Policy: Sorry, no pets allowedbrbrCancellation Policy:brbr100% refund if canceled at least 60 days before arrivalbrbr50% refund if canceled at least 30 days before arrivalbrbrOcean Breeze Bungalow is your perfect Key West sanctuary—luxury, privacy, and unbeatable location all in one. Book now to experience the best of island living!
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Exceptional(9)

$235.29

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Private Vacation Home

Paradise on Eaton- 3 bedroom 3 bath home w/private pool near Historic Seaport

Key West, Florida, United States

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrFEATURES:brBedrooms: 3 bedrooms - 2 in the main house & 1 in the cottage (1 queen, 2 twins, 1 king in the cottage)brBathrooms: 3 bathroomsbrLocation: Eaton StbrSquare Feet: 2020brParking: Parking is on street in non-residential spots or you can park in the overnight garage on Grinnell StbrAmenities: Private pool, mother-in-law cottage, Wifi, TVs, in-unit laundry, walkable to the historic seaport with shops & restaurantsbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.br*You do not have access to the vacant upstairs apartment*brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.brbrPool heating is $100 per week and must be requested in advance
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Bath 3

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Sleep 6

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Exceptional(36)

$227.68

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Condo

SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool!

Key West, Florida, United States

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCOMFORT AND VALUE IN TRUMAN ANNEX…brThis two bedroom first floor condominium is located in The Shipyard, a neighborhood of the coveted Truman Annex in the heart of Old Town Key West! Enjoy this comfortable ground floor front porch to sit and take in the passersby in true Key West fashion while you sip your coffee or relax with a glass of wine. With a preferred location and in exceptional condition, this little gem has a remodeled kitchen and bathroom and is located on the ground floor for your convenience. Throw your cares to the wind as you unwind in this charming, tree-shrouded neighborhood with walking paths and lanes. You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! The Shipyard also offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brComfort and functionality greet you as you enter this delightful abode. The fully equipped kitchen has everything you need to create a delicious meal for your loved ones, with a full size refrigerator, dishwasher, microwave, oven/stove and mini island. Gather around the dining table for 4 and then curl up on the couch in the adjacent living area to watch your favorite shows and movies. brbrSLEEPING ARRANGEMENTS…brUnwind from your day of island fun in one of the two comfy bedrooms. There is a twin bedroom that can be converted to a king if desired and a second room with a queen bed. Both rooms offer a clothing dresser, small flat screen tv and storage/hanging closets. Enjoy a shared hallway bathroom with a large glass-door shower and a washer/dryer closet adjacent to it.brbrOUTDOOR LIVING…brOpen the French door to the fenced private patio, inviting sultry breezes and Key West sunshine inside. This wonderful extension to the living space has a table for four where you can have your morning coffee or enjoy a cocktail after a long day of exploring. Fire up the grill and cook your fresh catch of the day!brbrPARKING...brThis home does offer parking for one vehicle (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community.brbrPETS...brThis is not a pet friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrCOME STAY A WHILE...
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Exceptional(33)

$1065.91

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Private Vacation Home

Keys Breeze - Walk to Duval, Private Pool

Key West, Florida, United States

Summary:brbrWelcome to 'Keys Breeze', your perfect private getaway in the heart of Key West! This fully renovated island home showcases the vibrant colors and charm of paradise. Located just a short walk from iconic spots like the Southernmost Point, Duval Street, and Key West's historic landmarks, you’ll have endless opportunities for adventure right at your doorstep.brbrbrbrRelax year-round by your private pool, ideal for lounging or entertaining guests. The luxury kitchen opens directly to the back patio through large sliding doors, making it easy to serve drinks and snacks poolside. At 'Keys, Please,' comfort and Key West charm come together to create the ultimate vacation experience!brbrbrbrThe Space:brbrEnjoy the comforts of privacy as you enter through the picket-fence and make your way into your own resort-like oasis. brbrbrbrEnter the front gate and find space to park your bike, sit on the front porch, or enjoy the seclusion of a front yard set away from the street. brbrbrbrAs you go up the front steps to the entryway, you will find a long hallway that provides separation from the sleeping spaces and living space. brbrbrbrThis home features three large bedrooms. The master bedroom on the second floor overlooks the pool and provides a king size bed and private en-suite bathroom. On the first floor, there are two guest bedrooms each with a queen size bed, allowing space for four more guests. There is a second full bathroom located on the first floor as well.brbrbrbrThere is fully-functional kitchen including all stainless-steel appliances and cooking essentials like pots & pans, silverware, and a Keurig coffee maker. The open floor plan makes hosting easy along with high-speed internet, wifi & a premium TV package. brbrbrbrPlentiful storage spaces give you the option to unpack, relax and make Key West your home!brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrCloser to the southern end of Duval street, Keys Please, is just walking distance from the Key West Lighthouse and Hemingway Home and Museum. However, you would never know the quiet neighborhood is in the middle of the action! You're only a few houses away from the island's famous Banana Cafe, where a delicious brunch or front-porch lunch is at your fingertips. When it's dinnertime, head to one of the local favorites- Abbondanza Italian Restaurant for pasta or Sushi Song for sushi, of course. Time for a drink Head the other direction to begin your Duval Crawl. Needless to say, you will find yourself in one of the best locations on the island no matter what kind of mood you're in!brbrbrbrGetting Around:brbrParking Information: There is no designated parking for this home. Parking on the street is on a first-come first serve basis including parking a compact vehicle on the rocks in front of the home. brbrFor additional parking here are some parking lot options:brbr• 204 Simonton Streetbrbr• Caroline Street Outdoor Parking Lotbrbr• Park N Ride Old Town GaragebrbrStreet parking information:brbr• There are pay-to-park spots and meters - it is free from 12am - 8am. There is a 3 day limit.brbr• The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only” and visitors are NOT permitted to park in them.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!brbrbrbrOther Things to Note:brbr- House features a private pool.brbr- Private washer/dryer.brbr- Not pet friendly
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Exceptional(6)

$181.0

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Condo

A SEAGLASS PARADISE ~ Charming 2 BR/1 Ba 1st Floor Condo in Truman Annex!

Key West, Florida, United States

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCHARMING 1ST FLOOR CONDO IN BEAUTIFUL SHIPYARD COMMUNITY OF TRUMAN ANNEX…brThis adorable retreat with a community pool is located in the prestigious gated community of Truman Annex in Key West's famous Old Town neighborhood. With 2 bedrooms and 1 bath, it's cozy perfection for 2 couples or a small family. You will revel in the location which is only 2 blocks from the vibrant excitement of Duval Street and only 1/4 mile from the pristine beach of Fort Zachary Taylor State Park. You are walking distance to the island's hot spots: The Green Parrot, Sloppy Joe's, Hemingway's Home and Mallory Square - home of the famous nightly Sunset Celebration.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brYour southernmost serenity begins as you enter the sun-filled living area, a perfect space to unwind after an exciting day on the town. The fully appointed kitchen has been totally remodeled with new cabinets, and granite countertops and will inspire you to conjure up your favorite tropical dishes. Decompress and read your favorite novel on the comfortable furnishings or indulge in relaxed conversation over a crafted cocktail. Enjoy hardwood floors, and ceramic tile throughout the home. A washer and dryer are provided for your convenience.brbrSLEEPING ARRANGEMENTS…brSlip into tranquil slumber in one of the two bedrooms with plush queen beds. The living room also offers a sleeper sofa.  The shared bathroom has  a walk-in shower and single vanity. brbrOUTDOOR LIVING…brThe Shipyard in Truman Annex is a charming, tree-shrouded hideaway with serene walking paths and lanes. The beautiful community pool is lined with lounge chairs and is perfect for soaking up the Key West sun. This unit features a beautiful landscaped courtyard located next to the community pool.brbrPARKING...brThis home does offer parking for one vehicle, just steps from the front door -  (vehicle cannot exceed 18 ft.). Oversized trucks and extra large SUVs are not permitted and will have to park outside of this community. brbrPETS...brThis is a dog friendly home (no cats) with a required pet fee. Please include the size and breed when inquiring. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet 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. brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.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!brbrYOUR ESCAPE TO PARADISE IS CALLING...
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Exceptional(2)

$3224.2

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Private Vacation Home

Big Groups Welcome • Pool • Near Duval

Key West, Florida, United States

Summary:brPerfect for bachelor and bachelorette parties, these 2 cottages that are quintessential Key West. Some of those most photographed homes, these sleep 16 guests comfortably. Enjoy life just a 30 second walk to Duval street with 2 kitchens, 2 living spaces, 5 bedrooms, 3.5 bathrooms, rooftop sundecks, historic Conch front porches, private laundry, parking, and a large connected back deck with a hot tub and pool.brbrThe Space:brWelcome to the Almost Southernmost Retreat in Key West, where the sun is shining, and the fun never stops! This property is the perfect getaway for groups of guys or gals looking for an exciting vacation. With stunning views of Hemingway's house and the lighthouse from your rooftop deck, you'll feel like you're living in paradise.brbrThis place is not only the perfect Key West getaway for groups of friends but is also an ideal spot for unforgettable bachelor and bachelorette parties. Whether you're looking to relax by the pool during the day or hit the town at night, our retreat is the perfect home base for your bachelor or bachelorette party. Don't miss out on the opportunity to create lasting memories with your best friends in one of the most beautiful places in the world. brbrLocated just steps away from Duval street, our retreat is in the heart of Key West's best restaurants, shops, and attractions. Or if you prefer to take it easy, kick back and soak up the island vibes with your private 8-man hot tub, pool, and sunbathing decks.brbrOur retreat is made up of two cozy cottages connected by a back porch. Let's take a closer look:brbrHouse number ONE...brThis spacious home boasts three bedrooms, two and a half bathrooms, a pool, a fully equipped kitchen, a cozy outdoor dining area, a living room with plenty of seating, a private sundeck, private laundry, and a front porch perfect for people-watching.brbrThe recently updated kitchen is fully stocked with everything you need to cook up a storm, and the bar that seats eight makes it easy to entertain your crew. An outdoor table is perfect for sharing meals while enjoying the sunshine.brbrThe living room offers ample seating for your entire party, and a queen sleeper sofa is available for extra guests. The downstairs bedroom is complete with a king-size bed and an en-suite bathroom, while the upstairs bedrooms include a queen bed and two queen beds with access to the sundeck.brbrHouse number TWO...brThis cozy Key West cottage is equipped with two bedrooms, one bathroom, a fully outfitted kitchen, a cozy outdoor dining area, a living room with tons of seating, another private sundeck, a second laundry location, and a front porch perfect for people-watching.brbrThe living room offers plenty of space for your entire group to relax, and a queen sleeper sofa is available for extra guests. The downstairs bedroom has a comfortable queen-size bed and an adjacent bathroom, while the upstairs bedroom features a king-size bed, plenty of storage, and access to the sundeck.brbrThat's two charming Key West cottages with a total of five bedrooms, three and a half baths, private parking, a hot tub, and a pool! Our retreat can comfortably accommodate up to 16 people, making it the perfect choice for your next group getaway.brbrThis place is not only the perfect Key West getaway for groups of friends but is also an ideal spot for unforgettable bachelor and bachelorette parties. Whether you're looking to relax by the pool during the day or hit the town at night, our retreat is the perfect home base for your bachelor or bachelorette party. You will create lasting memories with your best friends in one of the most beautiful places in the world. brbrDon't wait any longer to book your stay at our Almost Southernmost Retreat in Key West. With its unbeatable location and endless amenities, this property is sure to book up fast. We can't wait to welcome you to paradise!brbrCrawling distance from Duvalbr300 feet to the Key West Lighthousebr500 feet to Hemingway Homebr.4 miles to the Southernmost Pointbr.4 miles to the Key West Butterfly and Nature Conservationbr.7 miles to Sloppy Joe'sbr.9 miles to Mallory Squarebr3.7 miles to the airportbrbrGuest Access:brGuests will have access to the entire property.brbrThe Neighborhood:brThese quintessential Key West cottages are located in the heart of Old Town just half a block off Duval. You are in walking distance to all of what Key West has to offer...in fact, you are Hemingway's neighbor! Bars, restaurants, shops, and historic sites surround you. You can even peek the lighthouse from your second story sun deck.brbrGetting Around:brWith a central location like this you can walk, bike, scooter, drive, or Uber to all of what Key West has to offer.brbrOther Things to Note:brPool can be heated during the winter for $40 per night. Please let us know at least 3 days in advanced. brbrThis unit is pet-friendly. 40lb maximum per pet. $40/night per pet 2 pet max. Please let us know if you plan on bringing your pet. Check the rules for more details.brbrNo smoking inside the home.brbrSorry, no early check-in. We need time to make it perfect for your stay!
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Exceptional(1)

$240.06

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Condo

**SOUTHARD PEARL @ OLD TOWN** Condo & Community 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!brbrAmong the many hidden treasures of Old Town Key West, lives a charming loft-style condo that will melt your heart from the moment you enter. SOUTHARD PEARL is a 2 bedroom second floor condo located in Southard Square, an intimate community located in the heart of the island - a few blocks from Mallory Square, Duval Street and all the attractions Key West has to offer. Best of all, your rental includes Last Key Realty’s unrivaled Five-Star Guest Services, known for providing the most treasured Key West vacations.brbrTHE LOCATION...brbrSouthard Square is an intimate community in the heart of residential Old Town, just a few blocks from Duval Street. Imagine being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the Historic Seaport. Take a short stroll or ride bicycles down to the best of Key West, to hit local favorites like Mangia Mangia, The Café, Willie T’s and Bob’s on Margaret. Head down Margaret Street and you’ll be at BO’s Fish Wagon or Schooner Wharf.brbrTHE COMMUNITY POOL...brbrThe community pool is located in the center of the complex, with some chaise loungers for the sun seekers in your group. With Southard Square being such an intimate community, there’s always room. And parents, you have an eagle-eye view of the pool from the master bedroom’s private balcony! Although you won't need a vehicle to get around from this prime location, a dedicated parking space is included with your rental.brbrTHE LIVING AREA...brbrThe living room of SOUTHARD PEARL features a large flat screen TV and comfortable seating, including a plush sofa and two chairs. The sliding doors open to a private balcony so you can enjoy those refreshing island breezes. Lounge on the private balcony in the Adirondack chair or at the bistro set. The kitchen is fully equipped and provides every appliance and tool you’ll need to prepare meals at home. There is dining for four setup at the kitchen bar.brbrTHE ACCOMMODATIONS...brbr** Loft Style Master Suite: King bed, flat screen TV, and an en-suite bathroom with a walk-in shower. Plus a single twin bed suitable for young children.brbr** Guest Bedroom: King bed, flat screen TV, and access to the hallway bath with a walk-in shower.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 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 YouTube TV is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked unit also includes, but is not limited to the amenities on this list:brbr** Community Poolbr** Electric BBQ Grillbr** Off-street Dedicated ParkingbrbrOther notes:brbr** In person welcomebr** 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 9 adultsbr** Small Dogs Allowed - Max of 2 dogs and an additional fee of $200 per pet will applybr** 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.
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Exceptional(14)

$1112.19

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Private Vacation Home

Duval Vibes • Pool • 10 Guests

Key West, Florida, United States

Summary:brLocated only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, family reunions, or any celebration that bring you to town. This 3 bedroom/ 2.5 bathroom home has a full kitchen, spacious outdoor living space, outdoor shower, private second story sundeck, and a pool. Your group of up to 10 will love being steps away from all KW has to offer- be Hemingway's neighbor! Add this listing to your wishlist by clicking the ♥ in the upper right hand corner.brbrThe Space:brWelcome to our sun-soaked, beach-inspired oasis in beautiful Key West, Florida! This charming three-bedroom cottage offers the perfect retreat for up to 10 guests looking to experience the laid-back, island lifestyle. Nestled in a prime location, you'll be just minutes away from pristine beaches, vibrant nightlife, and an array of delightful dining options.brbrWith a fully-equipped kitchen at your disposal, you can whip up delicious meals using the fresh, local ingredients that Key West is known for. The large living space ensures that your group can enjoy each other's company, whether you're preparing a feast or simply relaxing in the living area.brbr Step out onto the private sundeck and bask in the warm Florida sun. For a refreshing dip, dive into your private swimming pool.brbrEach of the three spacious bedrooms is adorned with cozy, coastal-inspired linens and plush mattresses, ensuring a restful night's sleep after a day of adventure. With the capacity to comfortably sleep 10 people, our cottage is the ideal setting for families or groups of friends seeking a memorable getaway.brbrAdditional amenities include a washer and dryer, making it convenient for guests to pack light and keep their beach attire fresh throughout their stay. And, of course, we provide complimentary Wi-Fi to ensure you stay connected during your tropical escape.brbrWhether you're exploring the vibrant streets of Key West, soaking up the sun on the nearby beaches, or simply enjoying a refreshing cocktail by the pool, our beach-themed villa is the perfect home base for your Floridian adventure. Don't miss out on the opportunity to create unforgettable memories in this island paradise. Book your stay today!brbrThree bedrooms for you...br* the downstairs bedroom is complete with a king mattress and has an en suite bathroom.brbr* the second bedroom, located upstairs, has a queen bed.brbr* the third bedroom is also located upstairs and has two queen beds and access to the sundeck. brbrThere is one parking spot provided on the driveway. Additional paid street and lot parking is available within walking distance. brbrMax of 10 guests unless specific permission is granted from host.brbrThis central location puts a short walk or bike ride to all of Key West's most loved place...brbrCrawling distance from Duval Streetbr300 feet to the Key West Lighthousebr500 feet to Hemingway Homebr.4 miles to the Southernmost Pointbr.4 miles to the Key West Butterfly and Nature Conservationbr.7 miles to Sloppy Joe'sbr.9 miles to Mallory Squarebr3.7 miles to the airportbrbrThree bedrooms for you...br* the downstairs bedroom is complete with a king mattress and has an en suite bathroom.brbr* the second bedroom, located upstairs, has a queen bed.brbr* the third bedroom is also located upstairs and has two queen beds and access to the sundeck. brbrThere is one parking spot provided on the driveway. Additional paid street and lot parking is available within walking distance. brbrMax of 10 guests unless specific permission is granted from host.brbrThis central location puts a short walk or bike ride to all of Key West's most loved place...brbrCrawling distance from Duval Streetbr300 feet to the Key West Lighthousebr500 feet to Hemingway Homebr.4 miles to the Southernmost Pointbr.4 miles to the Key West Butterfly and Nature Conservationbr.7 miles to Sloppy Joe'sbr.9 miles to Mallory Squarebr3.7 miles to the airportbrbrGuest Access:brGuests will have access to the entire house.brbrThe Neighborhood:brThis quintessential Key West cottage is located in the heart of Old Town just half a block off Duval. You are in walking distance to all of what Key West has to offer...in fact, you are Hemingway's neighbor! Bars, restaurants, shops, and historic sites surround you. You can even peek the lighthouse from your second story sun deck.brbrGetting Around:brWith a central location like this you can walk, bike, scooter, drive, or Uber to all of what Key West has to offer. And, there is even an off street parking spot for your use!brbrOther Things to Note:brThis property can be reserved with the neighboring cottage to accommodate larger groups of up to 16 guests.brbrPool can be heated during the winter for $40 per night. Please let us know at least 3 days in advanced. brbrThis unit is pet-friendly. 40lb maximum per pet. $40/night per pet 2 pet max. Please let us know if you plan on bringing your pet. See rules for details.brbrNo smoking inside the home.brbrGuest should be at least 25 years old. brbrSorry, no early check-in. We need time to make it perfect for your stay!brbrInteraction with Guests:brWe aren’t on site, but always available if you need anything!
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Bath 2

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Sleep 10

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$1007.9

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Private Vacation Home

**THE ELEGANT EGRET @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThe perfect Key West getaway begins with a home that offers both space to gather and room to unwind. THE ELEGANT EGRET is exactly that and more! The thoughtfully designed living area makes it easy for everyone to come together, while private bedrooms and bathrooms provide a quiet retreat when it’s time to relax. Outside, a beautiful saltwater pool and lush lounge area create an inviting place to bask in the island sun, and off-street parking ensures your scooter or golf cart is always ready for the next adventure. Located within walking distance of vibrant Duval Street and the Historic Seaport, THE ELEGANT EGRET lets guests glide effortlessly between the excitement of Key West and the serenity of their own private retreat. Paired with Last Key Realty’s first-class Guest Services & In-house Concierge, you’ll never want to leave the nest.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 Historic Seaport. Take a stroll or ride your bike down to the best of Key West, three blocks down Olivia St to hit local favorites like Moondog Cafe, Martin’s, and Nine-One-Five. Just a few blocks down Windsor Lane and you'll be at BO's Fish Wagon or Schooner Wharf.brbrTHE LIVING AREA & KITCHEN...brbrStep into THE ELEGANT EGRET, where bright and airy meets island comfort. Large glass sliders pull the Florida sunshine into the main living space, highlighting the tall ceilings and beachy decor. The comfortable living room furniture includes a Queen sleeper sofa to accommodate extra guests. The layout is a dream for groups looking to spend time together, featuring a seamless flow between the cozy living room and the fully equipped kitchen. Guests can gather around the wet bar for happy hour or prep fresh local catch using the top-tier appliances. Dine together at the six-top interior dining table or keep the cook company at the kitchen bar, with seating for four. For added convenience, there is a stylish powder room located on the first floor.brbrTHE PRIVATE SALTWATER POOL...brbrStepping outside, the fully fenced tropical backyard was designed for total relaxation, featuring a heat-optional saltwater pool surrounded by lush landscaping. Whether you’re chasing the sun or seeking a cool spot in the shade, the adjustable lounge chairs make it easy to find your perfect vibe. When hunger strikes, fire up the propane grill for a poolside BBQ and enjoy your meal at the exterior dining table, with seating for four.brbrTHE ACCOMMODATIONS...brbr** First Floor Bedroom: Queen bed and an en-suite bathroom with a walk-in shower.brbr** Second Floor Master Bedroom: King bed, private balcony, and an en-suite bathroom with dual sinks and a walk-in shower. brbr** Second Floor Guest Bedroom: Two Twins OR One King bed, private balcony, and an en-suite bathroom with a shower and tub combination. brbr** This home features a stairlift to help make the 2nd floor accessible to every guest. A feature not often found in Key West!brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat & 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 Backyardbr** Private Saltwater Pool with Available Pool Heatbr** Propane BBQ grillbr** Off-Street ParkingbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 8 adultsbr** Pets Consideredbr** 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.brbrNEED MORE SPACE...brbrLast Key Realty manages the neighboring townhome, THE SOPHISTICATED SANDPIPER, along with a number of other townhomes in this intimate complex. Inquire for details!
Bed 3

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Bath 3

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Sleep 8

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Exceptional(78)

$2007.25

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Private Vacation Home

STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!

Key West, Florida, United States

ABUNDANCE IN OLD TOWN...brMajestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring everyone together under one roof yet offers the perfect separation by floors for privacy too.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrLOUNGE...brRelax by the pool on a lounge chair or one of the many porches and people watch.  Use one of the back porches to dine alfresco and enjoy some privacy. brbrAMENITIES PER FLOOR....brFirst Floor: Offers one king bedroom, a second bedroom with twins (that can be converted to a king) and both offer armoires and flat screen TVs. Between the two rooms there is a full bath with both a walk-in glass shower and claw tub. There is a queen room following these rooms adjoining with a queen suite accessible through the French doors off the kitchen or from the twin room. A full bath with a shower/ tub combo resides in between one of the queen bedrooms and the king bedroom. In addition to the beds and baths is a fully stocked kitchen and dining area, and spacious living room with a sleeper sofa offering an extra sleeping space for 1 - 2 guests. brbrSecond Floor:  There is a bedroom with a full size bed, another room with two twin beds (they do not convert), and a third room with a bunk and trundle (the top bunk mattress is a twin, the bottom bunk is a full mattress, and the trundle is a twin). This floor shares a full bath with walk-in glass shower, a living room with dining table and a full gourmet kitchen with stainless steel appliances. brbrThird Floor: This floor is equipped with a kitchenette, living room with flat screen and a full bath with a shower tub combo. The living room has a sleeper sofa that is best for one additional guest. The bedroom has a queen and a twin, dresser for storage, and a flat screen TV.brbrOUTDOOR LIVING AND AMENITIES...brThere is a private, heated pool, laundry area with two of each machines, outdoor dining tables and one parking spot for the house! The Historic Seaport is in walking distance and where you will find quaint shops & restaurants.  You are also just three short blocks to Duval Street and all of the attractions downtown Key West has to offer!  Take a sunset cruise, go snorkeling, or grab a fishing charter.brbrDISTANCES TO BEACHES...brSimonton Beach is 0.4 mibrFort Zachary Taylor Beach is 1.4 mibrSouth Beach is 1.1 mibrHiggs Beach is 1.3 mibrSmathers Beach is 2.3 mibrbrCONCIERGE 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 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrOPTIMIZE YOUR TIME & SPACE IN KEY WEST!
Bed 8

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Bath 4

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Sleep 20

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$819.1

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Private Vacation Home

~BLUE HAVEN~ Welcome to this single-story retreat with a pool!

Key West, Florida, United States

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: When you need Chaos Interrupted, this attractive home with a private, bougainvillea-adorned gate and a fenced yard welcomes you. The main entrance leads to the open concept family room and dining area. The primary king bedroom is to the left and includes nightstands, TV, dressers, and outdoor access. Its ensuite bath has a pedestal sink, tub/shower combo and storage. Enjoy TV from the family room’s large Italian leather sectional sofa. Two sets of French doors provide views of the pool zone from the family room and dining area. Moving to the kitchen you'll find white shaker cabinets, granite counters, stainless steel appliances, and a gas range. The island includes a sink and counter seating. Close by is the large wet bar where you can hone your mixology skills. It is equipped with a wine fridge, a custom countertop, and shelving. French doors make easy delivery of poolside cocktails.br brJust down the hall from the kitchen are two guest bedrooms and a shared hall bath. One bedroom is a king and the other is a queen. The king bedroom has a nightstand, TV, chest of drawers and single custom closet. Windows allow natural light to flood the space. The queen bedroom is also bright and includes a TV, two nightstands, built in closets, and French door access to the backyard. The shared hall bath is conveniently located and has a single vanity, a walk-in tiled shower, and storage.brbrAs a bonus, this home has a large, separate king bed/one bath guest house. The space is designed with a cathedral ceiling, several windows and doors, and a kitchenette. The skylights have window shades that can easily be raised/lowered. The kitchenette has a sink, counter, cabinets, mini refrigerator, and microwave. The bath has a tiled, walk-in shower, a vanity and convenient pool access. A large armoire for storage, TV, nightstands, and two sets of French doors round out the guest house and bathe it in sunshine. brbrThe backyard of this wonderful home includes a relaxing pool with water features. Lush landscaping and privacy fencing add to the tranquility of this paradise. Sip a cocktail poolside, enjoy a good book, or bask in the Key West sunshine. Solid surface flooring, ceiling fans, natural light and custom accents add to the appeal of this vacation home. If you are looking to wind down in a walkable location with a backyard entertaining area, look no further because this is the home for you!br brBED CONFIGURATION: The primary bedroom has a king bed. One guest room in the main house has a king bed and the other has a queen bed. The guest house has a king bed.brbrOUTDOOR AMENITIES: An outdoor gas grill and Blackstone allow for easy meal prep. Your Jandy pool system includes water features with options for jetting, chilling, or heating the water. The pool is heated seasonally (November-April) for an additional fee which will be assessed at the time of booking. An outdoor shower is located near the pool area. In addition, composite decking, loungers, comfortable seating, a dining table, fire pit and sunshades embellish the outdoor area. brbrPARKING: Parking is a privilege in Key West, but this home comes complete with off-street parking. brbrLOCATION: This mid-town location is perfect for biking or walking to the attractions of Key West, including Higgs Beach, Salute' on the Beach, and shopping at Fausto's Grocery Store. brbrPETS: This home is NOT pet-friendly. (If you have pets, please browse through our many homes that are pet friendly).brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Outdoor only security camera(s) are in use at this property, and may be used to verify guest occupancy and guest safety. Security camera(s) are not present inside the property nor at the pool area.***brbr***Managed by Historic Key West Vacation Rentals***
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Bath 3

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Sleep 8

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$441.44

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Private Vacation Home

**SEA BREEZE VILLA @ GRINNELL GARDENS** Modern Townhome & Pool + LAST KEY SERVIC

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSEA BREEZE VILLA is an elegant two-story townhome located in the quiet residential community of Grinnell Gardens, a quaint and intimate community in the middle of Old Town. From this location, you’ll be only a handful of blocks from world famous Duval Street in one direction, and a handful of blocks from Higgs Beach in the other direction. SEA BREEZE VILLA offers access to the heated community pool and one designated off-street parking space. Paired with Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, SEA BREEZE VILLA is an ideal setting for your month stay in paradise.brbrTHE LOCATION & COMMUNITY…brbrSEA BREEZE VILLA is situated in the quaint Grinnell Gardens, a private, gated community made up of 7 townhouses that surround a large community pool. You’ll be a short walk to all the sights and sound of Duval Street, and an easy walk or bike ride to the Atlantic beaches. You’ll also be within walking distance to several of Key West's best and most unique restaurants, including El Siboney, Salute! On the Beach, and Louie’s Backyard. While you won't need a car to get around, this home does have one designated off-street parking space should you decide to bring one.brbrTHE LIVING AREA, HOME OFFICE, & BACK PATIO...brbrUpon arriving, you will be greeted by the picturesque front porch that leads you into the villa. Inside, you’ll feel right at home with the calming earth tones and tropical décor. The open living area features a plush sectional sofa, which pulls out to a Queen sleeper, and a large flat screen TV. Custom cabinetry, gorgeous countertops, and high-end appliances set the tone in the fully equipped kitchen. You’ll have every tool you will need to prepare home-cooked meals. The eat-in dining table seats six comfortably and there’s a convenient half bathroom located just off the living area. Upstairs is a private home office in case you need to get work done during your vacation.brbrSlide open the back doors and step out to the spacious private patio. Relish in the island breezes while lounging in the patio furniture or treat your group to an outdoor meal using the propane grill and outdoor dining table with seating for up to six.brbrTHE ACCOMMODATIONS…brbr** Master Suite – Located on the Second floor with a King bed, a large flat screen TV, a closet, direct access to the private balcony, and an en-suite bathroom with a walk-in shower.brbr** Second Bedroom - Located on the Second floor with Two Twin beds OR One King bed, a flat screen TV, and access to the hall bathroom with a walk-in shower.brbr** Queen-sized sleeper sofa in the living room.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 Backyardbr** Community Pool Accessbr** Propane BBQ grillbr** Off-Street Parking for 1 vehiclebr** Home OfficebrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 6 adultsbr** Pets Not Allowed
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Exceptional(3)

$538.24

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Condo

Casa Bonita Key West ~ by Rent Key West Vacations

Key West, Florida, United States

Life is best lived from the balcony of this tranquil oceanfront condo. Feel like your feet are touching the sand, but yet your balcony is a floor above the actual sand with both sunrise and White St Pier views. This two bedroom, two bath condo is about to have an owner change and these photos are temporary until the owners complete the personalization of their new getaway.brbrThis oceanfront oasis is located in the Key West Beach Club, an upscale, gated community with two oceanfront pools, pavilion area, workout room and tennis court. The Key West Beach Club is one of the very few condo communities on the island that sits directly on the coastline.brbrEnter the open living, dining, kitchen with your eye drawn immediately to the view. The living room has light blue walls with dark wood flooors and features a modern sectional leather sofa with leather accent chairs & natural wood accent tables. The dining area has a spacious natural wood Room and Board dining table for 6. The kitchen features a full wall of cabinets and stainless appliances The coffee bar is a nice feature to enhance the kitchen. It is the counter height table in the kitchen that steals the show, with its surfboard inspired design and bar stools as another dining space or perfectly used as a serving area.brbrThe Primary Bedroom is being updated with a king tropical style bed and new mattress. The ensuite bath has a long vanity and large walk in shower. A concealed window in the shower allows you to see the ocean while showering, but the view is obscured from the bedroom for privacy. The guest room will feature a queen bed and desk for multipurpose use of the space. A hallway door between the guest rooom and guest bath will close to allow the large bathroom with walkin showere to serve as a second ensuite.brbrThe balcony offers a lounge area, outdoor dining and chaise loungers for relaxing oceansidde. brbrUnit Features:brCentral A/C, Wi-Fi, washer/dryer, security entry, garage parking and elevator access.brbrCommunity Amenities: Resort-type amenities include two oceanside pools (heated), tennis court, outside cooking facilities and pavilion, fitness center and sauna. Since the shoreline is natural, beach access is best at the public beaches on either side of the community. Smather’s Beach is around the corner to the right when exiting the property and Higgs Beach is just past White Street Pier to the left. There are plenty chaise lounges around the pool areas as well as the covered pavilion to enjoy during those sunny island afternoons.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.
Bed 2

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Bath 2

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Sleep 6

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Exceptional(4)

$1350.0

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Apartment

Hyatt Windward Pointe 2 bdrm 2 ba full kitch view

Key West, Florida, United States

2 bedroom suites sleep 6. Full kitchen, dining area, washer/dryer, balcony terrace. There are mostly 4 night stays, but shorter or longer stays are possible, and there are huge discounts for 5,6-, or 7-night stays, huge discounts, inquire.brbrThe spacebrThe Unit -- A spacious residential-style condominium featuring king-size bed and spa tub in master bedroom; queen-size bed in 2nd bedroom; queen sleeper sofa and a 25 inch or larger TV in living area, private screened-in balcony, ceiling fans, complimentary Wi-Fi Internet access, dataport, dishwasher, fully equipped kitchen, individual air conditioning control, in-room safe, microwave, radio alarm clock, separate sitting area, stereo system, in-room washer and dryer, additional tv(s) in bedroom(s), cable/satellite tv channels, coffee maker, dining area, DVD player, hairdryer, individual heat control, iron/ironing board, oven, refrigerator, two telephones, walk-in shower. Can sleep up to 6 guests.brbrAmenities -- Complimentary parking; concierge services; lagoon-shaped pool with outdoor whirlpool; picnic tables and barbeque grills; DVD rentals; baby sitting arranged by request and cribs & high chairs based on availabilitybr.brGuest accessbrGuests will have full access to all of the resorts current amenitiesbrbrOther things to notebrFor stays shorter than 7 nights. the resort may or may not charge a split week fee of $40-60. This is essentially a cleaning fee collected by the resort at check-out.brbrGovernment-issued photo identification and a credit card, debit card is required at check-in
Bed 2

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Bath 2

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Sleep 6

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