Vacation Rentals By Owner In Key West, FL

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThere’s no doubt you’ve heard of Duval Street; phenomenal restaurants, eclectic shops and legendary nightlife. This immaculate condo is just a half block away, giving you access to everything Duval Street has to offer while still allowing you to get a restful night’s sleep. SOUL OF DUVAL truly captures the essence of what makes Key West so special, with its playful decor, luxurious accommodations and fantastic location. Pair this with Last Key Realty’s Five Star Guest Services and your vacation in paradise will be truly unforgettable.brbrTHE LOCATION...brbrWith a prime Duval Street address, SOUL OF DUVAL is the choice location for anyone looking to have everything Key West offers at their fingertips. From the Southernmost Point and Hemingway House to famous spots like Sloppy Joe’s and Irish Kevin’s, SOUL OF DUVAL puts you in the heart of the action. Located on the ‘tamer’ 600 block of Duval, you’re within steps of Cuban Coffee Queen—a local favorite for your morning Con Leche! And with a dedicated, gated parking space, your car will be well protected while you stroll around Old Town.brbrTHE LIVING AREA...brbrSOUL OF DUVAL is the perfect place to retreat for a long weekend with a few friends. The living area is ideal for relaxing after a day full of exploration or after being out on the water. Relax in front of the large flat-screen smart TV while enjoying the comfortable seating perfect for your group. A dining table is available, along with a work space for those wishing to ‘work from paradise’. Enjoy your morning cup of coffee on the private balcony that overlooks the promenade leading to Duval.brbrTHE KITCHEN...brbrThe fully-outfitted kitchen sits off the living area with luxury appliances and tools, equipped with everything you'll need to prepare a meal at home in between enjoying the fantastic array of Old Town restaurant options, all just a few blocks walk away. Featuring both a drip coffee maker and a Keurig, not to mention Cuban Coffee Queen is right downstairs, all of your coffee needs will be well taken care of.brbrTHE ACCOMMODATIONS...brbr** Suite #1 - Queen bed, full closet and balcony access.brbr** Suite #2 - Queen bed and full closet.brbrThe shared bathroom features a full shower with a tub.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TV in Living Roombr** 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 & full cable includedbrbrIn addition, this fully stocked condo also includes, but is not limited to the amenities on this list:brbr** Reserved, gated parking space for 1 vehiclebr** Balcony overlooking the pathway to DuvalbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 4 adultsbr** Pets Not Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**SOUL OF DUVAL @ DUVAL** Modern/Centrally Located + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$222.28

OLD TOWN CUTIE CABANA…brBask in the charm of Old Town Key West as you approach this intimate and picturesque 2 bedroom townhome, located in the cozy enclave of Southernmost Cabana Community, just one block from famous Duval Street and the island's most popular spots. A rare find, this quaint getaway promises both proximity to all of the southernmost excitement yet tucked into a peaceful nest of serenity. Your perfect island retreat awaits you!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brA classic white picket fence greets you as you enter your tropical front yard and welcomes you to sit on your porch for a lovely cup of morning coffee and people watching. Ease into the entry where high ceilings and modern touches envelop you and open living and kitchen areas invite you to congregate with loved ones for entertaining and relaxation. Craft your favorite meals in the kitchen that boasts spacious countertops, stainless steel appliances and chef tools galore. Converse and dine at the breakfast bar for 3 or the cozy dining table for 4, then sprawl out on plush furnishings and enjoy a movie escape on your large wall-mounted TV. A full size washer/dryer closet and a full shower bathroom are located downstairs for your convenience.brbrSLEEPING ARRANGEMENTS...brFollow the stairs up to 2 plush king bedrooms that will tuck you in for an amazing night of slumber and rejuvenation. The primary bedroom offers an ensuite shower/tub combination and a private balcony for star-gazing and a nightcap. The guest bedroom features an ensuite shower bathroom. Both rooms are equipped with clothing dressers, storage closets and TVs for your enjoyment.brbrOUTDOOR LIVING...brStep outside to your spacious private back deck with ample and comfy seating and toss your fresh catch and steaks on the grill while sipping on a frosted cocktail. Enjoy the peace of listening to balmy breezes tickling swaying palms and the joyful sounds of nature in this ultimate serene setting. Follow the beautiful stone pathway that ambles throughout the cabana community and delights your senses with the grandeur of mature treescapes and lush gardens. You are only steps away from the gorgeous shared pool with a soothing waterfall feature. brbrPARKING...brThis home comes with 1 off street covered parking spot.brbrPETS...brThis home does not allow pets.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrSETTLE DOWN IN HEAVEN…

STAR OF THE SEA ~ Renovated 2 BR, 2.5 Ba Townhome w/ Shared Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$402.75

Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include:brbr2 bedrooms 1 bath {queen and 2 twins (or we can convert the 2 twins to a king bed with a king converter) plus a sleeper sofa in the living room.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.brSecond floor condo with outdoor balconies (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 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. brbrWe have many other Key West Truman Annex vacation rental listings that can be accessed via VRBO. Let us know if you have a particular interest or property size in mind.

Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0

Key West, Florida, United States

Bed

Bath

Sleeps

$488.45

Enjoy beautiful views of the Atlantic Ocean while sitting on your private porch. Located in the scenic La Brisa complex, this two bedroom condo features a large open floor plan with amazing views. Air conditioning and ceiling fans located in every room. Amenities include a pool, hot tub and tennis courts. Just a few steps across the street in Smathers Beach which offers beach chairs, umbrellas, paddle boards, kayaks and sailboats available for rent. brbrIf you are looking for entertainment- only five minutes away is Duval Street which features entertainment for all ages. Only five minutes Key West International Airport. brbrExtra features include one covered parking spot, three televisions, WiFi included, Cable TV, washer/dryer, fully equipped kitchen. brbrbrParking for two carsbrbrBecause of the beautiful property there are no trailers allowed to park. Just to unloading items

La Brisa - Ocean Views Across from Smathers Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$707.63

Summary:brbrSunnyside Up is a charming Conch-style home on United Street, just steps from Key West’s Old Town. With an open kitchen and living area that blends seamlessly with the outdoor space, it’s perfect for relaxing or entertaining. The tropical backyard includes a shared pool with the beach and local restaurants are only a few blocks away. This prime location makes it the ideal spot for your next vacation!brbrbrbrThe Space:brbrSunnyside Up is a spacious two-bedroom, two-bathroom unit with soaring ceilings and stylish furnishings throughout. The first bedroom features a queen bed and an extra-long twin bed, along with access to the balcony, while the second bedroom offers a queen bed and its own balcony access. The living area includes two queen pull-out couches, a work-from-home space, and smart TVs with all your favorite streaming services. The galley kitchen is fully equipped for home-cooked meals and morning coffee. French doors open to the back patio, where you can enjoy a tropical oasis complete with a shared pool, dining area, lounge chairs, and a grill.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrThis property is centrally located in Old Town, just a 10-minute walk to the beach and a 15-minute stroll to Duval Street. White Street Pier, nearby, offers volleyball nets and tennis courts. For activities close to Sunnyside Up, you can enjoy yoga classes at Shakti Yoga or visit The Local Butcher & Market. There are also plenty of excellent local restaurants nearby, including favorites like El Siboney, Frenchie’s Cafe, and Louie’s Backyard.brbrbrbrGetting Around:brbrOne of the best things about staying in Key West is how close everything is. The island’s compact size makes it easy to get around, and there are plenty of fun ways to do so. If you’re not in the mood to walk, you can bike to breakfast or take a scenic ride along the water at sunset. Fury and Island Bicycles offer rentals with convenient pick-up and drop-off services. For a more relaxed pace, rent a scooter or golf cart from Minty’s and feel like you’re on island time. If you prefer a ride, Uber, Lyft, or a taxi are always available, and Pink Taxi is a reliable, affordable option for airport transfers.brbrbrbrOther Things to Note:brbrPets are welcome! Our requirements are as follows: •40lb maximum per pet •$25/night • 2 pet maximum brbrPlease let us know if you plan on bringing your pet. brbrMid-stay cleans are available upon request.brbrHouse features a shared pool.brbrPrivate washer/dryer.

Sunnyside Up - Shared Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$286.57

Chicken Run at Custom House Inn | Stay on Duval Street!brbrWelcome to Chicken Run, a vibrant and uniquely themed studio located at the Custom House Inn—right in the heart of historic Duval Street. This newly remodeled studio offers modern, edgy design with a splash of bright green, perfectly complementing the colorful atmosphere of Key West. Whether you're visiting for a weekend getaway or an extended stay, you'll find yourself surrounded by the best food, entertainment, and culture the island has to offer.brbrThe Ambiance:brStep into a modern oasis with a King-size bed and a convenient Queen-size pullout couch, making Chicken Run ideal for couples or small groups. The studio features a sleek walk-in glass door shower and stylish sliding barn door, adding a touch of Key West's charm to the modern design. Inside, you'll enjoy a cable TV, mini-fridge, and coffee maker, providing all the essentials for a comfortable stay. Plus, guests can unwind on the turf balcony with cozy sectional couches, perfect for socializing or relaxing in the island breeze.brbrGuest Access:brOur contactless check-in system ensures a seamless arrival. You'll receive a personalized access code before your stay, allowing for easy entry. Chicken Run is conveniently located on the first floor for easy access.brbrThe Neighborhood:brLocated on the iconic 100 block of Duval Street, the Custom House Inn places you in the heart of Key West. Step outside and explore some of the island's most famous spots, including The World's Smallest Bar, Irish Kevin's, and the Hemingway House. Whether you're in the mood for local flavors at Mangoes or a lively night out at Willy T's and Fat Tuesday's, everything is within walking distance. While the lively atmosphere of Duval Street means some noise, you'll be right where all the action happens—perfect for those looking to experience the vibrant nightlife of Key West.brbrGetting Around:brKey West is incredibly walkable, and Chicken Run's central location puts many attractions just steps away. If you prefer to explore on wheels, you can easily rent a bike, scooter, or golf cart. Pedicabs, Uber, and taxis are also readily available to help you navigate Duval Street with ease.brbrParking Information:brPlease note there is no on-site parking for these units. However, several pay-to-park options are available nearby:br- Fleming Street Pay-to-Park Lot (closest option)br- 204 Simonton Streetbr- Caroline Street Outdoor Parking Lotbr- Park N Ride Old Town GaragebrbrOther Things to Note:br- For larger groups, you can reserve additional suites at Custom House Inn to accommodate up to 20 guests.br- The exterior of the building is equipped with security cameras to ensure a safe and enjoyable stay for all guests.br- This suite is located on the first floor.br- No washer/dryer on-site.br- No pets allowed.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrBook your stay at Chicken Run at Custom House Inn and enjoy the ultimate Key West vacation experience, right in the heart of Duval Street!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Chicken Run at Custom House Inn | Unbeatable Location!

Key West, Florida, United States

Bed

Bath

4

Sleeps

$843.75

AVAILABLE ONLY MAY MAY 30-JUN 6.brPhotos are from the resort website and may vary from the actual unit.brHyatt Vacation Club at Beach House offers spacious, island-inspired two-bedroom villas designed for comfort and relaxation. Perfect for families, couples traveling together, or extended stays, each villa provides the space and convenience of a private residence combined with resort-style amenities.brbrThe two-bedroom villa features a luxurious king-size bed in the primary suite, creating a peaceful place after a day in the sun. The second bedroom is equally comfortable, offering generous sleeping space and storage. A full bathroom (many villas include two full baths) provides modern fixtures, a large vanity, and a shower/tub combination for added convenience.brbrThe heart of the villa is the fully equipped kitchen, complete with full-size refrigerator, stove, oven, microwave, dishwasher, cookware, dishes, and utensils — everything needed to prepare meals with ease. The open-concept living and dining area offers comfortable seating, a dining table, and access to a private balcony or patio where you can enjoy tropical breezes.brbrAdditional features include:brbrComplimentary Wi-FibrbrFlat-screen TVsbrbrCentral air conditioningbrbrAmple closet and storage spacebrbrSurrounded by lush landscaping, the resort also offers a large outdoor pool, hot tub, and relaxing lounge areas. Located in Key West, guests enjoy easy access to beaches, water activities, dining, and the charm of Old Town.brbrWhether you're planning a family vacation or a relaxing island escape, this two-bedroom villa at Hyatt Vacation Club at Beach House provides comfort, space, and the perfect Key West atmosphere.

Beautiful two bedroom villa Hyatt Vacation Club Available only May 30 –Jun 6,

Key West, Florida, United States

Bed

Bath

Sleeps

$284.66

Location, location, location!brbrSituated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this nightly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided.brbrThis property will meet all of the demands a vacationer might have. Other amenities include a 1930's claw–foot soaking tub, free WIFI and digital HD cable.br

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Key West, Florida, United States

Bed

Bath

2

Sleeps

$466.0

Welcome to Higgs Beach Hideaway, your stylish island home in the heart of Key West’s desirable Casa Marina neighborhood, just minutes from world-famous Higgs Beach and local cafés, waterfront parks, and outdoor activities. This fully renovated tropical retreat blends comfort, convenience, and classic Keys charm — perfect for families, couples, or friends looking for a relaxing escape.brbrStep inside to an open-concept living area with plenty of space for gathering, playing games, or lounging after a day in the sunshine. The newly remodeled kitchen is fully equipped with modern appliances and essentials for cooking everything from casual breakfasts to gourmet dinners.brbrThe bright solarium invites you to open French doors straight to your private outdoor oasis — complete with a sparkling pool, waterfall feature, and plenty of room to soak up the tropical breeze.brbrWhether you’re enjoying morning coffee on the patio or unwinding poolside under the palms, this hideaway is your perfect Key West base.brbr** Space DetailsbrBedrooms – Sleeps Up to 8brbrPrimary Bedroom: King bed — sweet island sleep with cozy linens.brbrSecond Bedroom: Queen bed — comfortable and bright.brbrThird Bedroom: Two twin beds — ideal for kids or friends.brbrLiving Room: Queen sofa sleeper — extra bedding for flexibility.brbr** Bathroomsbrbr2 Full BathroomsbrbrStylishly remodeled guest bath with large glass-door shower.brbrPrimary bath adjacent to master suite.brbr** Kitchen & DiningbrbrFully outfitted kitchen with modern appliances and cookware.brbrBreakfast nook for casual meals plus a separate dining area for group dinners.brbr** Outdoor & LeisurebrbrPrivate heated pool with waterfall and lounging deck.brbrSpacious patio with seating — great for sunbathing or al fresco dining.brbrOutdoor tropical landscaping enhances privacy and island vibes.brbr** Location HighlightsbrbrMinutes to Higgs Beach, White Street Pier, Indigenous Park & dining.brbrQuiet, residential Casa Marina district with shops and cafés close by.brbr** Guest Comfort & EssentialsbrbrAir-conditioned throughout.brbrHigh-speed Wi-Fi, washer/dryer, iron/board.brbrParking for multiple vehicles.brbr** Best for…brbrFamilies, friends getaway, remote work stays (long-term comfort), and guests seeking a spacious tropical home near Key West’s beaches and attractions.

Tropical 3BR Casa Marina Retreat w/ Private Pool — Steps to Higgs Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$441.42

Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located near the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, boat tours, and more.brbrProperty amenities include: onsite washer and dryers, wireless internet access, pool, hot tub, and excellent location. Take a stroll or bike ride and enjoy the Truman Annex, The harbor, Mallory Square, Duval street and much more.brbrBike rentals available just outside the property on the Harbor walkwaybr.brWelcome to the perfect location in old town Key West. Situated on the western side of the island, this property overlooks the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, boat tours, and more.brbrThis 1 Bedroom, 1 Bath Condo sleeps 4, the primary suite has a king bed and connecting bath. The unit offers a fully-equipped kitchen, dining area, seating area with TV. The living room also features a sleeper sofa.brProperty amenities include: onsite washers and dryers, wireless internet access, pool, hot tub, and excellent location. Take a stroll or bike ride and enjoy the Truman Annex, The harbor, Mallory Square, Duval street and much more.brbrBike rentals available just outside the property on the Harbor walkwaybrbrNearby attractions include Mallory Square - 4 minute walk, The Green Room - 4 minute walk, and Tree House - 5 minute walk.brbr- Parking is approximately $27 per day, or approximately $55 per week (subject to change)br- An ID and a credit card are required upon arrival for a refundable security deposit.brbr*Fees are subject to change.brbrStays of less than 1 week may require additional housekeeping for a fee.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

Sunset Harbor - Old Town Key West Location - Beautiful Property

Key West, Florida, United States

Bed

Bath

Sleeps

$374.51

TRANQUIL BEAUTY: 3 BR’s, 2 Baths Private Haven paradise with huge private heated pool and landscaped back yard!brENJOY KEY WEST at its peaceful best in your 3BR, 2 bath private hideaway in a quiet neighborhood near Higgs and Smathers beaches and only a 10 minute bike or Uber ride from Duval Street. brOUTDOORS: Refresh while listening to the waterfall and getting some sun floating in your large, very private, heated and chilled pool. Rinse in the outdoor shower. Enjoy the recently upgraded and well-maintained landscaping Visit with friends or read a book and listen to the rain on your fully-shaded, large, tiled patio. Play cards, at the shaded outdoor dining table and / or sip cool drinks from the nearby beverage refrigerator. Or, if you like, enjoy takeout from Paradise Café only a block away. Take walks through the gorgeous midtown west neighborhood or bike to beautiful Higgs or Smathers beaches only a 5 minute ride away.brINSIDE: This charming cottage offers 3 bedrooms, 2 baths, and comfortable indoor and outdoor seating spaces. When you enter, light shines through the window in the vaulted ceiling above the fully equipped kitchen with its quartz countertops and new stainless steel appliances. The breakfast bar seats three. The kitchen opens into a living area that’s an ideal spot for watching your favorite tv shows on the cable TV or via high-speed fiber optic Wifi. On the other side of the kitchen is a dining room with its 6-person table, its beverage center, and multiple French doors that merge your indoor with your outdoor living. The two guest bedrooms and their shared bath with walk-in shower form a suite located just off the kitchen. The master bedroom suite with its vaulted ceiling, French doors overlooking the pool, and modern en suite bath with walk-in shower is located off of the dining room.brPARKING: There is off-street parking for up to three vehicles or a boat trailer and 1or 2 vehicles.

Tranquil Beauty-Private Pool - Outside Lanai-Beaches Nearby

Key West, Florida, United States

Bed

Bath

Sleeps

$239.57

This 2 bedroom 2 bath town-home is just what you are looking for. The amenities include two community pools, a gym, and a butterfly garden. This community is located on Stock Island which is five miles from Duval Street and all of the Historic Old Town Key West attractions. The property is also located two miles from some of the best beaches on the island. Enjoy world-class fishing access either using your own boat with nearby deep-water access to the Atlantic, or by chartering a boat at any of our local marinas. All properties are outfitted with washer/dryer, pots, pans, towels, linens, have central air conditioning, parking for up to 2 vehicles and access to two community pools. THIS HOME RENTS FOR 28 NIGHTS MINIMUM.br**Pets considered with additional non refundable fee upon owner approval**

It's a Salt Life After All at the Golf Club in Key West

Key West, Florida, United States

2

Bed

2

Bath

6

Sleeps

$575.92

Hyatt Windward Pointe in Key West is a tranquil resort offering a luxurious escape on the island’s serene southeast coast. Overlooking the Atlantic Ocean, the resort features spacious two-bedroom suites with fully equipped kitchens, private balconies, and elegant living spaces, perfect for relaxing or entertaining.brbrGuests can unwind in the lush tropical gardens, enjoy the sparkling infinity-edge pool, or lounge in the whirlpool spa. The resort also offers a poolside restaurant, poolside barbecue area and convenient access to nearby attractions, including beaches, watersports, and the vibrant Key West nightlife. brbrThe poolside restaurant and market, Abbey Road was named after the Beatles who stayed at this address under the former property name, Key Wester Motel. The Hyatt Windward Pointe was built to replace the Key Wester Motel. Abby Road serves lunch and dinner 11 a.m. to 7 p.m. in casual surroundings. Abbey Road also carries those essentials you may have forgotten at home or the souvenir you may want to bring home!brbrWith its peaceful ambiance, stunning ocean views, and upscale amenities, Hyatt Windward Pointe provides an idyllic retreat for couples, families, and anyone seeking the perfect Key West getaway.brbrLOCATION: Enjoy the white sands of the world-famous Smathers Beach. Only 3 miles away is the famous southernmost point, old town Key West and all the fun of Duval Street. Just minutes away guests will find the Fort East Martello Museum, world-class fishing, and excellent restaurants.brbr.brThis beautiful 2-Bedroom features a master suite with king bed and adjoining bath with walk-in shower and jetted tub, guest bedroom with queen bed and full bath and a living room with a pull out sleeper sofa, TV and Wi-Fi internet access. The unit can accommodate up to 6 people. It features a full kitchen with granite countertops and appliances, including a full size fridge, stove-top burners, a microwave, a sink, a coffee maker, and a toaster. The unit also features a washer and dryer. brbrROOM AMENITIES INCLUDE:br- Entertainment with WiFi, phone, and premium TV channels, alarm clockbr- Kitchen with refrigerator, microwave, stove-top, oven, coffee/tea maker, toaster, sink, cookware, dishware, and utensilsbr- Shower & Jetted tubbr- In-room climate control (air conditioning)br- Free toiletriesbr- Hair dryer Iron/ironing boardbr- Separate sitting areabr- In-room safebr- Sofa bedbr- Cribs/infant beds available upon requestbrbrAn ID and a credit card are required upon arrival for a refundable security deposit.brPhotos representative of units. Specific unit assigned at check-in (including floor and location). Lower floor units view may be obstructed by landscaping.brbrStays of less than 1 week may require additional housekeeping for a fee, as well as a split week fee.brbrThe resort will be undergoing an enhancement project from May 2026 to August 2026. During this time, guests may experience limited-view obstructions if located in building under renovation. Additionally, anticipate minor construction noise between the hours of 9AM to 5PM.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

Hyatt Windward Pointe 2 Bedroom

Key West, Florida, United States

Bed

Bath

Sleeps

$538.87

Hyatt Windward Pointe in Key West is a tranquil resort offering a luxurious escape on the island’s serene southeast coast. Overlooking the Atlantic Ocean, the resort features spacious two-bedroom suites with fully equipped kitchens, private balconies, and elegant living spaces, perfect for relaxing or entertaining.brbrGuests can unwind in the lush tropical gardens, enjoy the sparkling infinity-edge pool, or lounge in the whirlpool spa. The resort also offers a poolside restaurant, poolside barbecue area and convenient access to nearby attractions, including beaches, watersports, and the vibrant Key West nightlife. brbrThe poolside restaurant and market, Abbey Road was named after the Beatles who stayed at this address under the former property name, Key Wester Motel. The Hyatt Windward Pointe was built to replace the Key Wester Motel. Abby Road serves lunch and dinner 11 a.m. to 7 p.m. in casual surroundings. Abbey Road also carries those essentials you may have forgotten at home or the souvenir you may want to bring home!brbrWith its peaceful ambiance, stunning ocean views, and upscale amenities, Hyatt Windward Pointe provides an idyllic retreat for couples, families, and anyone seeking the perfect Key West getaway.brbrLOCATION: Enjoy the white sands of the world-famous Smathers Beach. Only 3 miles away is the famous southernmost point, old town Key West and all the fun of Duval Street. Just minutes away guests will find the Fort East Martello Museum, world-class fishing, and excellent restaurants.brbr.brThis beautiful 2-Bedroom features a master suite with king bed and adjoining bath with walk-in shower and jetted tub, guest bedroom with queen bed and full bath and a living room with a pull out sleeper sofa, TV and Wi-Fi internet access. The unit can accommodate up to 6 people. It features a full kitchen with granite countertops and appliances, including a full size fridge, stove-top burners, a microwave, a sink, a coffee maker, and a toaster. The unit also features a washer and dryer. brbrROOM AMENITIES INCLUDE:br- Entertainment with WiFi, phone, and premium TV channels, alarm clockbr- Kitchen with refrigerator, microwave, stove-top, oven, coffee/tea maker, toaster, sink, cookware, dishware, and utensilsbr- Shower & Jetted tubbr- In-room climate control (air conditioning)br- Free toiletriesbr- Hair dryer Iron/ironing boardbr- Separate sitting areabr- In-room safebr- Sofa bedbr- Cribs/infant beds available upon requestbrbrAn ID and a credit card are required upon arrival for a refundable security deposit.brPhotos representative of units. Specific unit assigned at check-in (including floor and location). Lower floor units view may be obstructed by landscaping.brbrStays of less than 1 week may require additional housekeeping for a fee, as well as a split week fee.brbrThe resort will be undergoing an enhancement project from May 2026 to August 2026. During this time, guests may experience limited-view obstructions if located in building under renovation. Additionally, anticipate minor construction noise between the hours of 9AM to 5PM.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

Hyatt Windward Pointe 2 Bedroom

Key West, Florida, United States

Bed

Bath

Sleeps

$460.84

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 2 1/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within the historic old town. Just 2 blocks from Duval Street, and also just 2 blocks from the beach. You really can have it all! brbrWe are proud to bring this property to the community. We have been looking at the key west market for the past 3 years and truly believe this property is the one we have been waiting for! Sleeping 6, its located in the premier resort in Key West. Santa Maria resort is Number 1 on TripAdvisor and regularly obtains awards as one of the best boutique hotels in the US. The property is over the top two levels of a stunning corner townhouse. Overlooking the pool and located on the side walkway which leads directly from the car park into the resort. brbrAs an owners unit, you do not pay the daily resort fee of $35 a day. This economic alternative means you wont receive daily cleaning (although you are welcome to upgrade to daily cleaning for an additional fee). You still get full enjoyment of the pool and we provide you with a parking permit which allowed one car to park within the car park by the hotel (this is on a first come first serve basis) brbrAs you are not paying this fee to the hotel you do not get access to the reception, happy hour, hotel pool towels. You do get access to the gym (although the water bottles are only provided for hotel guests)brbrTHE PROPERTY LEVEL 2 The unit itself has been perfectly designed with 4 balconies. 2 of which have fantastic views overlooking the pool!brbr We give you access by remote codes for the duration of your stay. The entrance up a flight of stairs provides a very private experience. You enter into a beautifully appointed living room which consists of a sofa bed which sleeps 2. The kitchen at the rear has been fully equipped and includes all eating and cooking utensils. On the same level you can also enjoy a half bathroom, and the unit enjoys its own washer/dryer. There is a balcony directly from the living room with outdoor furniture. brbrLEVEL 3 The upper level has two bedrooms with their own bathrooms and plenty of closet space. Each room has its own tv. The master bedroom has its own balcony overlooking the pool. We provide linen, towels and towels for the pool area

Key West dream townhouse -Sleeps 6 Like new! Old Town - Perfect location

Key West, Florida, United States

Bed

Bath

Sleeps

$531.46

Everyone enjoys time in Key West, and staying at The Orchid Oasis take it to a new level. We are a family of Conchs that have been born and raised in Key West for seven generations, and we look forward to welcoming you to stay in our home. brbrThis home is located just minutes from everything that's great about Key West. You can walk or ride a bike to both Smather's Beach or Higgs Beach in under five minutes, and you're just two minutes from White Street pier where you can watch the most amazing sunsets you'll ever see!brbrOur pictures show you all the great aspects of this home so be sure to look through them to get a good feel for the house and the layout. brbrWe offer all the comforts you need for your stay in paradise including WiFi, flat screen TVs, laundry, lovely and inviting pool with waterfalls and ample parking space. There is a 4 person maximum limit to this home (NO EXCEPTIONS). brbrThis home is in a quiet area of Key West and is not recommended for parties or group celebrations. We ask you to please be respectful of the neighbors and keep the noise level to a minimum.brbrWe can also provide home cooked meals for an additional fee! Want authentic Cuban roast pork with rice and black beans and the best Key Lime Pie on the island Or maybe a custom made batch of Key Lime Fudge made by the woman who invented it Or Key West Pink Shrimp & Cheese Grits WE CAN DO THEM ALL! brbrThis property has a ONE MONTH minimum stay requirement.brbrNOTE: We are VERY selective about who we rent to! This home is right next to our primary residence so we only rent to couples or groups of four or less. If you are coming to party, be loud and make a mess please don't even inquire. We want tenants who are going to treat this home like they're own.

Orchid Oasis - Only Minutes from Smather's and Rest Beaches!

Key West, Florida, United States

Bed

Bath

Sleeps

$914.51

Summary:brbrLuxury 2BD/ 2BA Suite with Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Porch with Amazing ViewsbrbrbrbrThe Space:brbrEscape the Ordinary....brbrbrbrThe Carysfort Lighthouse Suite is a luxury 2 BD/ 2BA stand-alone house located directly in front of one of our two brand new oasis pools with direct access to the pool deck and brand-new property amenities that sleeps up to 6 guests. Completely renovated in 2024, the suite is our premier unit and offers breathtaking pool views through the rear glass folding doors with Key West Lighthouse and partial Duval Street views from the private front porch located on a quiet Key West Lane. The suite also comes with an exclusive off-street parking spot for your stay.brbrbrbrSuite Amenities:brbrbrbr• Luxury king master bedroom with premium linensbrbr• Luxury queen bedroom with premium linensbrbr• Queen sleeper sofabrbr• Fully equipped brand new kitchen with bar seatingbrbr• Spa quality glass master en-suite bathroombrbr• Second bathroom with showerbrbr• Hardwood flooring throughout the suitebrbr• Spacious front porch with lighthouse and partial Duval St. viewsbrbr• Smart TVs with the latest Roku device for apps and streamingbrbr• High-speed Fiber Wi-Fibrbr• Washer and dryerbrbr• Luxury well-appointed furnishing and artworkbrbr• Reserved and exclusive off-street parking space for one vehiclebrbr• Accordian door access to one of the property's two oasis pools directly behind the unitbrbr• Our largest suite at more than 800 square feetbrbr• Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Carysfort Reef Lighthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind. This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr• Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr• Brand-new spacious pool decks around each poolbrbr• Six luxury teak chaise loungers with umbrellas and pillowsbrbr• Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr• Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr• A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr• Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr• Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr• Covered bar kiosk for enjoying a cocktailbrbr• Key West tropical foliage throughout the property with lighted step-stone pathsbrbr• Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr• Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3, two-bedroom suites, 2, one-bedroom suites, 1, one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr• The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr• The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr• The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr• Key West Lighthouse Museum, 2-minute walkbrbr• Ernest Hemingway Home and Museum, 2-minute walkbrbr• Blue Heaven Restaurant, 5-minute walkbrbr• Southernmost Point Buoy, 8-minute walkbrbr• Key West Butterfly Conservatory, 8-minute walkbrbr• Sloppy Joe’s Bar, 12-minute walkbrbr• Key West Amphitheater and Park, 12-minute walkbrbr• Mallory Square Sunset, 12-minute walkbrbr• Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!

Carysfort Reef Light Suite

Key West, Florida, United States

Bed

Bath

Sleeps

$523.51

Welcome to Old Key West. Our Classic Old Town style duplex, with two independent fully renovated homes in the same property, ideal for families with kids, big groups, business travelers, couples get away, and friends vacation. This elegant homes are very well located in the middle of all the fun, but with the privacy and the peace of this paradise island; fully equipped for your convenience and at walking distance to great views, parks, beach and excellent restaurants.brThe spacebr*Please note that this home only allows minimum stays of 28 nights or longer.brbrCome and live a real Old Town experience in Key West. Our home from 1929, is located in a quiet, residential area near the Historic Seaport, beaches, sport activities, the Southernmost Buoy and the iconic Duval street, where food, wine, art and music are fused magically.

Two fully independent units in a Duplex, with independent entrances. One Rent!

Key West, Florida, United States

Bed

Bath

Sleeps

$273.7

Birds of a Feather at Custom House Inn | Vibrant Stay on Duval Street!brbrDiscover the heart of Key West at Birds of a Feather, one of five uniquely themed suites at the Custom House Inn, right on famous Duval Street. This bright and colorful hideaway offers modern comforts and a fun, edgy design, providing the perfect base for your island adventure. Surrounded by incredible dining, nightlife, and iconic landmarks, you'll be in the middle of it all while enjoying a cozy retreat when it's time to unwind.brbrThe Ambiance:brStep into Birds of a Feather, a lively pink-accented suite designed for up to four guests. Relax in style with the following amenities:br- A plush King-sized bed for ultimate comfortbr- A Queen-sized sleeper sofa for additional guestsbr- A stylish bathroom featuring a walk-in glass shower and charming sliding barn doorbr- In-room conveniences like a mini fridge, coffee maker, and cable TVbrbrStep outside to the shared turf balcony with a comfy sectional for socializing or enjoying the buzz of Duval StreetbrLocated on the second floor with stair access, this suite offers plenty of space to relax after a day of exploring Key West.brbrGuest Access:brSkip the hassle of check-ins! With our easy, contactless check-in system, you'll receive personalized access codes before arrival, allowing you to walk right in and start your vacation stress-free.brbrThe Neighborhood:brSituated on the lively 100 block of Duval Street, Birds of a Feather is perfectly positioned to give you direct access to the best of Key West. Just steps from the inn, you'll find local hot spots like The World's Smallest Bar, Fogarty's, Irish Kevin's, and Moondog Café. Historic attractions such as the Hemingway House, Key West Lighthouse, and the Southernmost Point are just a short walk away, making it easy to explore the island's culture and history.brbrLooking for a night out Iconic bars like Willy T's, Rick's, and Fat Tuesday's are practically on your doorstep. Embrace the lively energy of Duval Street while enjoying the convenience of being close to everything!brbrGetting Around:brKey West is made for exploring, and with so many transportation options, getting around is a breeze. Rent a bike, scooter, or golf cart to cruise around the island, or hop on a pedi-cab for a fun ride. Many attractions are within walking distance, but you can also grab an Uber, Taxi, or Lyft if you prefer a quick ride. Need suggestions on where to go or what to do We're happy to help with recommendations!brbrParking Information:brPlease note there is no on-site parking for these units. However, several pay-to-park options are available nearby:br- Fleming Street Pay-to-Park Lot (closest option)br- 204 Simonton Streetbr- Caroline Street Outdoor Parking Lotbr- Park N Ride Old Town GaragebrbrOther Things to Note:br- For larger groups, you can reserve additional suites at Custom House Inn to accommodate up to 20 guests.br- The exterior of the building is equipped with security cameras to ensure a safe and enjoyable stay for all guests.br- This suite is located on the second floor.br- No washer/dryer on-site.br- No pets allowed.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrBook your stay at Birds of a Feather at Custom House Inn and enjoy the ultimate Key West vacation experience, right in the heart of Duval Street!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Birds of a Feather at Custom House Inn | Perfect Stay on Duval Street!

Key West, Florida, United States

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