Vacation Rentals By Owner In Key West, FL

Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool.brThe home has is well stocked with towels, bedding and house hold appliances and blow dryer.brThis beautiful home is close to ocean and the beach. Only three blocks to Jimmy Buffets, Sloppy Joes and Duval Street entertainment. One of the nicest homes in the best area of Key West.brbr30 Night minimum stay is required.

Tropical State of Mind Key West FL

Key West, Florida, United States

Bed

Bath

Sleeps

$263.75

Amazing LOCATION! Truman Annex: SHABBY CHICKEN - come stay at the large & proud bird in town!! Large front yard and porch to watch Key West pass by. Beautiful, sunny and spacious living areas with private, large landscaped backyard with two dining areas. Ground Floor. See what's so special about the Shabby Chicken...it's not too shabby after all. POOL within 1 minute walk.brbrDISCOUNTED MONTHLY RATES. brThe Shabby Chicken is one of largest condos in the Shipyard. With a spacious, sunny, ground floorplan it's a perfect place to call your own for month(s) at a time.**brbrOur fantastic cleaner has been with us for 14 years. Read our reviews, historically we always been known to have a spotless, clean place. Stay with us!brbrSUMMARYbr120!! 5-STAR rating and the best floor plan around. It feels more like a home than a condo and great for long stays.br* Exceptional, over-sized floor plan with 2 bedrooms on OPPOSITE sides of condo (Guest room is King bed OR Twin beds), br*Large double vanity bath, full-size kitchen is only offered in a couple of units in the Truman Annex Shipyard. br* Spacious deck along with a outdoor patio/dining area. Relax at the Truman Annex Shipyard POOL - which is a minute walk from the condo. brbrBEDROOMS & IDEAL FLOOR PLANbrTwo very spacious bedrooms, located on OPPOSITE sides of condo for privacy br*Primary bedroom has KING bed br*Guest bedroom can be King OR two twin beds br* Each bedroom has ample room to store clothes. Currently the living room and only the guest room has a TV.brbr*Large bathroom with double sink vanity, nice walk-in shower. brbr*Centrally located living roombr* Full Size kitchenbr*Spacious, sunny with plenty of windowsbr* In-unit washer and dryerbr br**Our outdoor space is 2-3 times the size of other condos. brbrDETAILSbrLIVING AREA & KITCHEN...brThe central living area with new large, leather sectional couch with a full size kitchen provides a great floor plan for 2-4 people. The kitchen is equipped with all new appliances, countertop, modern backsplash and finishes. There is counter-top seating and a large dining table with beautiful lighting and seating for four or more that is stylish and functional. brWasher and dryer!brbrOUTDOORS...brTwo sets of French doors lead to the HUGE, MULTI-SPACE OUTDOORS. LUSH landscaping and privacy.brEnjoy morning coffee or an intimate dinner at the comfortable dining table on the large, covered, private deck. Step down to the herringbone brick patio that is able to accommodate a small party to dine alfresco. Or take a relaxing nap or read a book on the lounger under the palm.brbrPOOL...brLess than a one minute walk to the poolbrbrAMENITIES...brThis ground floor condo is very clean, and has well-appointed bedrooms which have been completely updated with linens, art work and comfortable beds. A new washer/dryer are located within the unit for your convenience. The fully equipped kitchen with all new appliances, pots & pans, towels & linens and central air conditioning provide all the amenities you want for long- and short-term stays. brbrYou'll also enjoy TV in the living room with an Italian-made large, comfortable leather sectional. Secure wireless Wi-Fi and and Bluetooth speaker for your device to connect to for music.brbrWasher and Dryer in the unitbrbrOur condo is outfitted with beach towels, beach chairs, a cooler, etc. brbrPARKING SPOTbrWe also have on-site parking with a designated parking spot, although it's likely you will not need (or want) to get in your car while you're here. NOTE: Our parking lot cannot accommodate oversized vehicles over 18' long (measured from bumper to hitch) or 80 wide.brbrWHAT MAKES IT SPECIAL...brThe Shabby Chicken (for it's shabby chic design) has interesting design elements, such as vintage clocks, modern geometric patterns, original artwork from Cuba and local artists, wood carvings from the Philippines and India, along with beautiful tapestries. The place feels very luxurious, contemporary, and relaxing.brbrPROXIMITY TO PLACES...brThe Shabby Chicken is within easy walking and biking distance to everything Old Town Key West has to offer, including Fort Zachary Beach and a one minute walk to the Truman Annex pool. Walk down to the Truman Annex waterfront to take in a special and low-key sunset for which only the locals know about. Walk or bike through the gorgeous Truman Annex over to happening Mallory Square for shops, museums, and special events. brCondo Updates:br2024: New air handler and furnacebr2023 All New Highly Insulated Windows and Doorsbr2022 Completely landscaped front and backyardbr2021: New ACbr2020: New washer and dryer appliancesbr brWe request a 7+ night minimum. brDISCOUNT MONTHLY RATES. **Reservations made for 28 days or more will have a 60 day (rather than 30 day) cancellation policy.brbrCheers! Marie and Tom

Sunny & Beautiful 1st flr, Large In/Outdoors, 2BR K/T, 1 Bath, Truman Anx, Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

This newly renovated shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautiful weather and evening cocktails. This is a nicely appointed unit with 2 full bedrooms and 1 freshly renovated bathroom. This unit has 2 flat screen TV's and wireless internet access. Perfect location and just 2 blocks from Duval. This condo is just minutes from all the sun-kissed festivities, yet perfectly situated a block off Duval in a gated community giving you the best of both worlds. brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Best Time at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

4

Sleeps

$210.52

AGE REQUIREMENT:brEveryone must be 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbr Just two blocks off iconic Duval Street which offers the best in entertainment, attractions, restaurants, shopping and more. This cottage is part of a three home complex surrounding a shared pool. It is strolling distance to historic Fort Zachary Taylor Beach, Truman Waterfront Park, the Hemingway Home and Lighthouse Museums, and everything Old Town has to offer.brbrWelcome to your island getaway, an enchanting Key West conch cottage that radiates tropical charm inside and out. Just two blocks from lively Duval Street, this colorful retreat perfectly blends the energy of Old Town with the laid-back comfort of home.brbrStep inside and you’ll be greeted by soaring beam ceilings, trapezoid windows, and an airy, light-filled floor plan. The new owner has leaned into Key West’s playful spirit with bold flamingo wallpaper, bright accent pieces, and fun, tropical furnishings that bring each space to life. A modern kitchen with stainless steel appliances, gas stove, and composite counters adds convenience while keeping the island vibe. The two cozy bedrooms provide flexible sleeping arrangements, One king size adjustable bed inside the main house and the other in the bonus small pool house with a futon bed along with updated bathroom in main house and half bath in pool house with an outside shower balance comfort and style. One designated off street parking space. Features include high-speed wireless, flat screen TVs in the bedroom, kitchen/living room, outside living area and in the bonus pool house.brbrOutdoors, the mosaic-tiled pool shimmers in shades of sea and sand, offering the perfect place to cool off under swaying palms. A whimsical pool house with futon, half bath, and outdoor shower creates a private oasis for guests, while the covered patio—complete with outdoor TV setup—is ideal for entertaining. Brick pavers, tropical landscaping, and colorful details carry the vibrant design from indoors to out. Enjoy dining on your own covered brick patio that overlooks the shared pool area. Guests are welcome to enjoy the pool and shared deck space, while being mindful of the close proximity to the other homes in the compound. In addition to the back deck, the front porch is the perfect spot for morning coffee or for refreshing afternoon beverages.brbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. Pets allowed upon approval.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.

Flamingo Cottage charming in Old Town with a pool & 1 Offstreet parking space

Key West, Florida, United States

Bed

Bath

Sleeps

$232.89

Oceanfront Elegance – Renovated 2BR/2BA Condo at 1800 Atlantic, Key WestbrbrWelcome to paradise at 1800 Atlantic! This stunning, fully renovated 2-bedroom, 2-bath oceanfront condominium offers the perfect blend of luxury, comfort, and unbeatable views of the Atlantic Ocean.brbrLocated in a prime spot within the complex, this unit is just steps from the Olympic-size heated lap pool and features easy access to parking and elevators—ideal for guests with accessibility needs. The highlight of the property is the expansive 60-foot wraparound balcony, accessible from the living room and both bedrooms, where you can relax and enjoy breathtaking ocean vistas.brbrInside, the condo has been completely remodeled with thoughtful design and upscale finishes. The spacious primary suite includes a cozy sitting area and a private en-suite bath. The guest bedroom is furnished with a brand new queen bedroom set. brbrResort-style amenities include:brbr Heated Olympic-size lap pool & 20-person oceanfront jacuzzibr Sauna and fully equipped fitness centerbr 3 lighted tennis courts (including one clay court)br BBQ grills and beautifully landscaped courtyard areasbr Small sunning beach on-site; Smathers Beach is just a 5-minute walk awaybr One assigned covered parking space per unitbrbrConveniently located just 1.5 miles from the Atlantic end of Duval Street and 2.5 miles from Mallory Square, you’ll be close to all the action while enjoying a peaceful, private retreat.brbrWhether you're here to relax, explore, or hit the tennis courts, this condo at 1800 Atlantic is the perfect home base for your Key West adventure.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Oceanfront Luxury Panoramic Views & Designer Finishes Key West Beach location

Key West, Florida, United States

Bed

Bath

Sleeps

$388.43

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrThe moment you arrive at this midtown mansion, you’ll know your time in Key West is going to be special. The circular driveway and covered portico provide a grand entrance, which set the stage for what awaits you inside. At over 3,900 square feet, ISLAND OPULENCE is one of the largest private residences in Key West. This impressive ranch-style home offers an open and airy layout that allows for guests to congregate both indoors and out. Luxury is in no short supply here, you’ll feel like a golden age Hollywood star escaping to your mansion in the tropics. Best of all, your rental includes Last Key Realty’s unrivaled Five-Star Guest Services, known for providing unforgettable vacations with the hospitality and concierge access you would expect from a lavish resort.brbrTHE LIVING AREA…brbrEntering through the majestic front door, you’ll immediately notice the high-end finishes and just how spacious the home truly is. ISLAND OPULENCE has soaring ceilings and high windows that flood the main living area with natural light. The living room offers plenty of oversized, comfortable seating to entertain or to simply enjoy a movie on the enormous flat screen TV.brbrThe fully equipped chef’s kitchen is open to the living room and features top-of-the-line appliances, and includes a coffee bar and built-in ice maker. The extra-large dining table offers seating for ten. If you’re an early riser, you can grab a cup of coffee and enjoy a moment of peace at the breakfast nook.brbrTHE BACKYARD & POOL…brbrStepping outside through the double sets of French doors, you’ll be transported to your very own private oasis. The backyard is surrounded by a concrete privacy wall and features lush tropical landscaping. You’ll have plenty of room for everyone to lay out and relax or enjoy an outdoor meal. Taking a dip in the heated pool is the perfect way to relax after a day of exploring the island. Treat everyone to a poolside BBQ using the luxurious propane grill and outdoor dining tables. There’s even a convenient half bathroom located by the pool area.brbrTHE LOCATION…brbrAll of this splendor in a centralized mid-island location, on a quiet residential street. You’ll be away from the hustle & bustle of Duval St, yet only be a short 10 minute drive or Uber ride down to the heart of the action. There’s plenty of off-street parking in the driveway for cars, golf carts, scooters, and bikes.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom: Located on the First Floor with a King bed, a flat screen TV, a desk, a massive walk-in closet and a gorgeous en-suite bathroom with double sinks, a walk-in shower, and luxurious bathtub. The master bedroom also has French doors that open to the pool area.brbr** Second Bedroom: Located on the First Floor with Two Twins OR One King bed, a flat screen TV, and access to the full bathroom in the hall.brbr** Third Bedroom: Located on the First Floor with a King bed, a flat screen TV, and access to the full bathroom in the hall.brbr** Fourth Bedroom: Located on the Second Floor with a King bed, a flat screen TV, a desk, a private balcony, a Queen sleeper sofa, and an en-suite bathroom with a walk-in shower.brbr** A Full-sized Murphy bed on the first floor provides additional accommodations for one guest.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room & All Bedroomsbr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Private Yardbr** Private Heated Poolbr** Propane BBQ Grillbr** Off-street Parking for Multiple Vehiclesbr** Queen Sleeper Sofabr** Full Murphy BedbrbrOther 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 11 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per pet

**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$644.52

THE PROPERTY: Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quaint cottage, you can sit back and relax in the comfortable living room with ample seating for you and your guests. The room is enhanced by a vaulted ceiling, coveted Dade County pine, and French doors that lead out to the lush gardens. A wet bar area is complete with a beverage refrigerator, a bar sink, microwave and a coffee maker. Beyond the family room is a convenient first-floor full bath with a walk-in shower. Just outside this bath is an open staircase that provides access to the upstairs open loft bedroom. This sleeping area has a window and is complete with a queen bed, chair, lamps, and dresser storage. Towards the rear of the home is the sunny first floor primary ensuite bedroom with king bed, storage closet and French doors. The ensuite bath has a beautiful walk-in shower, double sinks, and enclosed water closet. Please note this home has no washer/dryer at this time. Enjoy island life in Hibiscus Cottage- a convenient location with a shared pool!brbrBED CONFIGURATION: One king bed on the first floor and a queen bed in the upstairs open loft space. brbrOUTDOOR AMENITIES: A large shared pool is available for Hibiscus Cottage guests; it is located at the back of the complex and is surrounded by swaying palms and tropical landscaping. Loungers are in place for your use.brbrPARKING: No designated parking. Limited on-street parking may be available in the neighborhood.brbrLOCATION: Historic Old Town, walkable to Duval Street, shops, bars, and restaurants. Enjoy nearby entertainment on Mallory Square. 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 STRICT NON SMOKING HOME AND COMPLEX.brbr***Guests must be 25 years of age or older to rent; please note this is an18 and older complex.brbr***Hibiscus Cottage is independently managed by Historic Key West Vacation Rentals. At this time, it does not participate in the amenities and activities offered at the resort***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.***br***Managed by Historic Key West Vacation Rentals***

Cottage

~Hibiscus Cottage~ 18+ Adult Only cottage near Duval St

Key West, Florida, United States

Bed

Bath

Sleeps

$169.72

CLASSIC KEY WEST CHARMER...brWelcome to this historic one bedroom one bath abode that features an additional sleeping loft for guests! This quaint delight is just a short stroll from world-class restaurants, famous bars, shopping, museums and historical points of interest, such as the Lighthouse and Hemingway House. This is an ideal location for living your authentic island life, close to all the exciting action yet tucked into a quiet and colorful neighborhood.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brWalk through your private white picket gate and enter this adorable cottage that features a bright and updated living room and kitchen area. Tropical sunshine is abundant through large windows and vaulted ceilings that give this charmer a spacious feel. Cool off and relax on the couch and cushioned chair while you enjoy your movies on the wall-mounted TV. The living area opens to the spacious and modern dine-in kitchen. Sharpen your creative culinary skills in this fully equipped kitchen that offers stainless appliances and stone countertops. The bathroom is adjacent to the kitchen and has been fully renovated. Wash your cares away in the walk-in glass door rain shower. A stacked washer and dryer occupy the bathroom closet for your convenience. brbrSLEEPING ARRANGEMENTS…brThe queen bedroom will invite you to rest and recharge after your day in paradise. Snuggle up with your favorite book or enjoy your wall-mounted tv in the plush bedding that promises sweet slumber. Unpack your shorts and sandals in the hanging/storage closet and clothing dresser. There is also a loft that is accessed by a wall ladder. It offers an additional queen bed for guests.brbrOUTDOOR LIVING…brThe darling front porch is a wonderful spot for morning coffee and quiet reflection. A very private backyard patio can be accessed through the French doors in the kitchen, a perfect space for grilling up your fresh catch, rinsing off in the outdoor shower and an intimate conversation while star gazing. brbrPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.brbrPETS...brThis home allows for pets under 35 lb and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests.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). brbrAUTHENTIC ISLAND LIVING…

BEACHY KEEN ~ Charming 1 BR, 1 Ba Home w/ Loft in Great Location!

Key West, Florida, United States

Bed

Bath

4

Sleeps

$373.0

Hyatt Vacation Club at Beach House is an oceanfront resort located along the Gulf side of Key West. The property features tropical landscaping, waterfront views, and a peaceful setting that highlights the natural beauty of the island.brbrGuests can relax at the oceanfront pool, unwind in the hot tub, or enjoy outdoor seating areas overlooking the water. The resort provides a quiet retreat while still being within a short drive of Key West’s vibrant Old Town and Duval Street attractions.brbrThis two-bedroom villa offers a spacious layout designed for families or groups traveling together. The residence typically includes a primary bedroom with a king bed, a second bedroom with additional bedding, and a comfortable living area with a sleeper sofa.brbrThe villa also includes a full kitchen equipped with appliances, cookware, and dining space for preparing meals during your stay. A private balcony provides a relaxing outdoor space where guests can enjoy tropical breezes and views of the surrounding island environment.brbrThe resort is located along the Gulf side of Key West, offering a peaceful waterfront setting while still being close to the island’s attractions. Guests can easily visit Duval Street, Mallory Square, and historic Old Town for restaurants, shops, and famous sunset celebrations.brbrThe island also offers boating, fishing, snorkeling, and sunset cruises throughout the surrounding waters of the Florida Keys.brbrKOALA Disclosure Summary:brbr-IMPORTANT: Payments appear as “KOALA VACATIONS” on credit card statements.brbr- BEFORE YOUR CHECK-IN: This booking requires the name and address of the person checking in. THE PERSON CHECKING IN MUST MATCH THE PHOTO ID PROVIDED TO US.brbr- This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.brbr- The primary guest checking in must be at least 21 years old.brbr- Resorts own and manage all units/amenities; unit assignments at check-in.brbr- Room photos are samples; actual furniture/layout may vary.brbr- The Resort is responsible for maintenance, may alter/close select amenities due to COVID-19 or other factors. KOALA is only responsible for ensuring your check-in and unit category.brbr- KOALA is not responsible for unit condition or resort services. For resort, unit or guest related issues after check-in, please contact the resort management.brbr- Check cancellation policy before booking. No refunds after the cancellation deadline due to any reason, including COVID-19 (except full resort closures), natural disasters, or personal changes. For these reasons we always recommend purchasing trip insurance for unforeseen circumstances like these. This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.

Hotel Resort

Key West Resort Stay – 2BR Villa Near Beaches & Sunset Views

Key West, Florida, United States

Bed

Bath

Sleeps

$571.0

Hyatt Vacation Club at Beach House is an oceanfront resort located along the Gulf side of Key West. The property features tropical landscaping, waterfront views, and a peaceful setting that highlights the natural beauty of the island.brbrGuests can relax at the oceanfront pool, unwind in the hot tub, or enjoy outdoor seating areas overlooking the water. The resort provides a quiet retreat while still being within a short drive of Key West’s vibrant Old Town and Duval Street attractions.brbrThis two-bedroom villa offers a spacious layout designed for families or groups traveling together. The residence typically includes a primary bedroom with a king bed, a second bedroom with additional bedding, and a comfortable living area with a sleeper sofa.brbrThe villa also includes a full kitchen equipped with appliances, cookware, and dining space for preparing meals during your stay. A private balcony provides a relaxing outdoor space where guests can enjoy tropical breezes and views of the surrounding island environment.brbrThe resort is located along the Gulf side of Key West, offering a peaceful waterfront setting while still being close to the island’s attractions. Guests can easily visit Duval Street, Mallory Square, and historic Old Town for restaurants, shops, and famous sunset celebrations.brbrThe island also offers boating, fishing, snorkeling, and sunset cruises throughout the surrounding waters of the Florida Keys.brbrKOALA Disclosure Summary:brbr-IMPORTANT: Payments appear as “KOALA VACATIONS” on credit card statements.brbr- BEFORE YOUR CHECK-IN: This booking requires the name and address of the person checking in. THE PERSON CHECKING IN MUST MATCH THE PHOTO ID PROVIDED TO US.brbr- This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.brbr- The primary guest checking in must be at least 21 years old.brbr- Resorts own and manage all units/amenities; unit assignments at check-in.brbr- Room photos are samples; actual furniture/layout may vary.brbr- The Resort is responsible for maintenance, may alter/close select amenities due to COVID-19 or other factors. KOALA is only responsible for ensuring your check-in and unit category.brbr- KOALA is not responsible for unit condition or resort services. For resort, unit or guest related issues after check-in, please contact the resort management.brbr- Check cancellation policy before booking. No refunds after the cancellation deadline due to any reason, including COVID-19 (except full resort closures), natural disasters, or personal changes. For these reasons we always recommend purchasing trip insurance for unforeseen circumstances like these. This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.

Hotel Resort

Key West Resort Stay – 2BR Villa Near Beaches & Sunset Views

Key West, Florida, United States

Bed

Bath

Sleeps

$466.11

Welcome to Mermaids RetreatbrbrEscape to the tropical charm of Mermaids Retreat, where comfort meets convenience in a serene island setting. This spacious home features a full-sized kitchen and a cozy dining area, perfect for preparing and enjoying meals with family or friends. Unwind on the front and back porches, ideal for soaking in the warm, year-round island breeze.brbrOn the main floor, you’ll find a comfortable bedroom just off the living room and a full bathroom for added convenience. Upstairs, there are two generously sized bedrooms, each with a king-sized bed and private en suite bathroom. Enjoy the island air from the large open porch, and take advantage of the stackable washer and dryer for all your laundry needs.brbrParking is available in a nearby outdoor lot, with space for up to two vehicles.brbrJust steps from your front door, enjoy access to the community pool and clubhouse, complete with a small fitness center.brbrExplore local flavor right in the neighborhood—Stock Island is home to several popular dining spots:brbr Roostica and Hog Fish Bar & Grill serve up local favorites,br El Siboney offers authentic Cuban cuisine,br The Docks features a fresh seafood market, andbr Croissant De France, located directly across the street, tempts with a delicious selection of baked goods.brbrWhether you're looking for relaxation or adventure, Mermaids Retreat is your perfect island getaway.

Mermaid's Retreat at Coral Hammock Key West Island living at its best

Key West, Florida, United States

Bed

Bath

Sleeps

$575.07

MARITIME-INSPIRED LIVING…brCome unwind in this desirable retreat, tucked in a quiet and private lane just a stone's throw from all the excitement of Duval Street. Your location is ideal with swaying palm trees and gentle sea breezes all around. This upscale delight beckons you into your tropical haven beneath the twinkling stars of Key West. Allow your delightful island story to unfold.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brThe open concept features a custom gourmet kitchen with luxury appliances and a uniquely furnished living area with inspiring design pieces that invites you to sit for a spell and enjoy the grand yet cozy surroundings. The Master Shaker craftsman-built kitchen is a gourmet cook's dream and the nearby sliding glass doors bring the back yard inside while you concoct your next culinary creation. A large flat screen smart TV invites you to sink down into the plush accommodations and enjoy your favorite movie or sporting event. brbrSLEEPING ARRANGEMENTS…brThe primary suite offers a plush king bed with an en-suite bathroom and access to the beautiful backyard area. A queen guest room resides steps away with access to the hallway bathroom with a shower/tub combination. The third bedroom houses a king bed with an ensuite bathroom with double sinks and a shower and access to a private front porch for your morning coffee. All bedrooms have flat screen TVs and ample closets or dresser drawer space for your unpacking convenience. A loft area above the living space makes a fun place to escape for a good book on the bench or for a quick afternoon nap on one of the two twins beds that can convert to a king.brbrOUTDOOR LIVING...brVenture out through the sliding doors to your gorgeous private lanai and pool area that includes an outdoor kitchen with a wet bar, TV and dining area hosting seating for six. Take a dip with a margarita in hand and delight in the beautiful tile work and water feature followed by a rinse in the outdoor shower. Stretch out for a nap in the pool lounge area before firing up the large propane grill for dinner under the bewitching stars. brbrPARKING...brThe home offers off-street parking for one vehicle.brbrPETS...brDogs ONLY are considered at this home and a pet fee is required. Please include the size and breed when inquiring. 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).brbrCOME AND STAY A WHILE…

LOVE LANDING ~ Charming 3 Bedroom, 3 Bathroom Home w/ Pool and Parking!

Key West, Florida, United States

Bed

Bath

8

Sleeps

$413.4

Seas the Breeze – Poolside Condo Near the BeachbrbrRelax in this poolside island retreat on the quiet side of Key West. This 2BR condo offers a peaceful setting with a heated pool, hot tub, and tennis courts, and just minutes from the beach.brbrSeas the Breeze is a laid-back island escape overlooking the pool, tucked within the lush grounds of Sunrise Suites, this tranquil two-bedroom condo blends peaceful surroundings with nearby adventure. With the shoreline just a short drive away and Old Town’s vibrant energy within easy reach, it’s the perfect balance of relaxation and exploration.brbrInside, the space is designed for comfort and effortless vacation living. The open layout creates a relaxed atmosphere, while large windows and coastal touches bring in that unmistakable Key West feel. Guests can enjoy access to resort-style amenities including a temperature-controlled pool, bubbling spa, tennis courts, and scenic paths ideal for morning strolls or bike rides.brbrDesigned with comfort and island living in mind, Seas the Breeze features a spacious and open-plan inviting layout:brbr• Primary Bedroom: King bed with private en-suite bathroom, flat screen TV, large walk-in closetbr• Guest Bedroom: Queen bed with private entry to the hallway bathroom, flat screen TV, large double-door closetbr• Living Area: Plush sofa that converts to a queen bed, accommodating up to 6 guests comfortablybrbr• Kitchen & Buffet Bar: Fully equipped kitchen with cookware, cutlery, oven, refrigerator, microwave, stove, dishwasher, Keurig coffee maker, blender, toaster, dining sets, and much more. Buffet bar accommodates 4 guests.brbrStep out onto your private balcony with seating for 4, the perfect spot for morning coffee or evening cocktails. Inside, unwind in the bright, tropical-inspired living space with cable TV and plenty of room to relax.brbrParkingbrbr• Each stay includes a parking space available on a first-come, first-served basis.br• Proximity to your vacation rental isn’t guaranteed, with potential for an additional spot based on availability.br• As guests at Sunrise Suites, parking is free of charge.brbrCheck-In / Check-Outbrbr• Check-In: 4:00 PMbr• Check-Out: 10:00 AMbrbrCommunity & LocationbrbrLocated within the upscale Sunrise Suites Resort Community, you’re just minutes from Key West International Airport, making arrivals and departures effortless. For added convenience, the community also features an on-site convenience store and spa.brbrWhen you’re ready to explore beyond the peaceful setting of Seas the Breeze at Sunrise Suites, you’re just a 10-minute drive from the heart of Key West. Discover vibrant restaurants, boutique shopping, live entertainment, and the world-famous Duval Street. Don’t miss Mallory Square, where you can take in Key West’s stunning nightly sunset celebrations — an unforgettable island experience, all just moments away.brbrGetting Around Key Westbrbr• Walk to the beach and nearby attractionsbr• Rent bikes for scenic rides along the islandbr• Cruise by scooter or golf cart for the full island experiencebr(We recommend Pirate Scooter Rentals for scooters and bikes.)br• Uber, Lyft, and local taxis are readily availablebrbrGuest Communicationbrbr• We use the Lodgify messaging app as well as text messages to interact with our guests.br• Contactless entry instructions are typically sent on the day of check-in.br• Depending on when you book, prior messages and texts will clearly outline any additional instructions.brbrSunset Vacation and Management homes are rented to family groups and responsible adult groups only.brbrCooler Rentals Availablebrbr• Cooler rentals are available for the duration of your stay for a flat fee of $50.br• Available options include large insulated coolers in approximately 70-quart capacity (40” x 18”) and 60-quart capacity (24” x 17”), as well as a rolling insulated cooler for easy transport.br• A round YETI-style bucket cooler with an approximate 45-quart capacity is also available.br• Complimentary drop-off and pick-up service is included for a seamless and hassle-free experience during your stay.brbrGuest Accessbrbr• Keyless entrybr• Elevator and stairs access

Apartment

Seas the Breeze – Poolside Condo Near the Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$531.27

️Thank you for your interest in our stunning Oceanfront 3-bedroom property in Key West! brBefore proceeding , we kindly request you to contact the owner directly for stays less than 28 days as minimum rental is 28 days. This will ensure that all your requirements are addressed and you receive the best possible experience during your stay.brbrOur Oceanfront property is truly a gem and provides an unparalleled experience by placing you directly on the shoreline, with nothing between you and the soothing sensation of the ocean. The breathtaking views are visible from every room, and the expansive 90-foot scenic balcony allows you to relish magnificent unobstructed ocean vistas. Imagine starting your day with a captivating sunrise on one end of the balcony and ending it with a mesmerizing sunset on the other.brbrThis oversized 3-bedroom suite offers ample space for you and your guests to enjoy. With a generous 2,200 square feet under air, you'll find ultimate comfort and privacy. Each bedroom boasts its own spectacular ocean view, ensuring that everyone gets to savor this unique experience. The suite is tastefully furnished with one king-size bed, one queen bed, and two single beds that can be combined to make a king upon advance request. Additionally, there are two single roll-away beds and an oversized sectional in the living room, providing extra sleeping options.brbrThe property has undergone recent upgrades to enhance your stay. You'll have access to free high-speed wireless internet, smart televisions with Hi-Definition Cable in all bedrooms, and a new washer and dryer for your convenience. The master bathroom features a luxurious spa design shower with a body sprayer, while his and hers separate vanity areas and large walk-in closets provide ample space. The gourmet kitchen is fully equipped with high-end appliances, including Sub-Zero and Jennair, allowing you to prepare meals and enjoy dining in the comfort of your oceanfront retreat.brbrAs for amenities, our property offers everything you need for a blissful vacation. You can take a dip in the 70 ft. heated Olympic pool, located just feet from the water's edge, or unwind in the oversized 12-person in-ground heated Jacuzzi. The lush landscape surrounding the pool area features well-manicured orchards and tropical flowers. We also provide BBQ facilities near the shaded pavilion, and poolside bathrooms, lockers, and Hot Stone saunas for your convenience.brbrFor outdoor enthusiasts, Smathers Beach, Key West's longest beach, is just a few steps to the left of our property. You'll find various activities there, including volleyball, sailboat rentals, and parasailing. If you're interested, local bike rental companies can deliver Beach Cruisers to your doorstep, allowing you to explore the numerous bike paths, trails, and the vibrant Duval Street area.brbrFurthermore, we encourage you to try something different and rent a scooter or electric car to enhance your island adventure. These options provide a fun and exciting way to discover the hidden gems of Key West. Tennis enthusiasts will be pleased to know that our property includes one of the few clay tennis courts on the island, along with two lighted hard courts and handball courts.brbrWe prioritize your safety and security throughout your stay. The property features a full-time, around-the-clock security patrol, ensuring a worry-free experience. One covered off-street parking space is provided, and ample guest parking spots are available outside.brbrOur convenient location offers easy access to the airport, car rental area, and is approximately two miles away from popular attractions

️3 Bdrm - Ocean View Every Room-Secluded -Quiet-OCEAN FRONT- 90 FT BALCONY

Key West, Florida, United States

Bed

Bath

Sleeps

$423.94

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrMODERN IN THE MEADOWS proves you can blend modern and tropical styles into a beautifully laidback yet chic home. This fabulous monthly rental shines with its high-end upgrades, refined decor and upscale accommodations. Located in the quiet, sought-after Meadows neighborhood you’ll be treated to a month of relaxation in a newly renovated home that features a spacious wrap-around balcony, your own private pool and four spacious bedroom suites. In combination with Last Key Realty’s Five-Star Guest Services, your month at MODERN IN THE MEADOWS will leave you wanting for nothing!brbrbrbrbrTHE TWO LIVING AREAS...brbrFrom the moment you enter, you’ll be enchanted by the open floor plan that allows the Florida sunlight to radiate throughout the first floor. The gorgeous wooden flooring brings a natural feel to an otherwise modern home. The downstairs living room has comfortable seating options for everyone in your group to utilize while enjoying the large flat screen TV. There’s also a powder room conveniently located just off the downstairs living room. The downstairs living room flows into the dining area where you’ll find a classy dining table that harkens back to the picnic table we lovingly remember eating at in summers past. Modern decor is showcased in the kitchen, accentuated by the unique chandelier overhead. The spacious, fully equipped kitchen has everything the chef in your group will need to create delicious meals.brbrClimb the stairs to the second floor where you'll find a second living area, which features a large flat screen TV and plush sofa. In addition, this space includes a desk and chair in case you need to work during your month stay in paradise. The upstairs living room sofa pulls out to a queen sleeper for those extra guests that pop by. brbrTHE PRIVATE POOL… brbrbrWhen you head out back you’ll find your private pool waiting for you to take a plunge. If you’re visiting during the cooler months we can turn up the heat to ensure you’re nice and toasty. And in the summer, there are chaise loungers to enjoy so you can soak up the rays in-between refreshing dips. Bringing home a fresh catch Toss it on the BBQ and dine like a true local.brbrTHE LOCATION…brbrThe Meadows is a residential district of Old Town Key West. This quiet neighborhood with primarily residential homes and noiseless streets is perfect for peaceful evening strolls, but also within walking distance of the commercial area of White Street with restaurants, shops, and Fausto's grocery store. This home is located less than a mile from Duval Street, an easy bike ride or walk any day. Although you won't need a vehicle to get around from this ideal location, there's on-street parking available in front of the house on Pine Street if you decide to bring one.brbrbrTHE ACCOMMODATIONS… brbrbrbr** Master Bedroom: Located on the First Floor with a King bed, a flat screen TV, large closet and a gorgeous en-suite bathroom with double vanity and luxurious walk-in shower.brbr** Second Suite: Located on the Second Floor with a King bed, a flat screen TV, and an en-suite bathroom reminiscent of a private spa.brbrbrbr** Third Suite: Located on the Second Floor with a Queen bed, a flat screen TV, and an en-suite bathroom reminiscent of a private spa.brbrbrbr** Fourth Suite: Located on the Second Floor with a Queen bed, a flat screen TV, and an en-suite bathroom reminiscent of a private spa.brbrbrbrALL LAST KEY VACATION HOMES INCLUDE:brbrbrbr** Washer & Dryerbrbr** Central Heat and A/Cbrbr** Ceiling Fansbrbr** Flat Screen Cable TVs in Living Room & All Bedroomsbrbr** Fully-Equipped Kitchenbrbr** Basic stock of spicesbrbr** Starter supply of paper productsbr** Starter set of cleaning productsbrbr** Linens and Towels providedbrbr** Wireless high-speed Internet access and full cable is includedbrbr** Full Time Concierge ServicebrbrbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbrbrbr** Fully Fenced & Landscaped Private Yardbrbr** Private Heated Poolbrbr** Propane BBQ Grillbr** Queen Sleeper SofabrbrbrbrOther notes:brbrbr** In person welcomebrbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 10 adultsbrbr** Small Dogs Allowed - Max of 2 dogs allowed with an additional fee of $200 per pet to apply

**MODERN IN THE MEADOWS @ THE MEADOWS** Chic Private Home & Pool + LAST KEY SERV

Key West, Florida, United States

Bed

Bath

Sleeps

$725.58

We know that you will enjoy staying in this oasis of comfort in the paradise of Key West. Our Cuban Club Condo is an immaculately maintained and spacious 1500 sq. ft. retreat with cathedral ceilings, and elegant and comfortable furnishings. It also features a 30-foot balcony overlooking Duval Street for small gatherings or to just relax with a cocktail and people watch.brbrOur two-bed, two-bath condo can sleep up to 8. The master bedroom has a king-size bed and pull out queen sleeper sofa, private en-suite bathroom and balcony. The second bedroom has a queen-size bed and connecting private bathroom. There is a queen-size sleeper sofa in living room for two additional guests. brbrOur condo features: wireless high speed internet; flat screen TVs in living room, and both bedrooms; an assigned parking spot in our Cuban Club Condo private parking lot; and a fully-equipped kitchen which includes blender, toaster, drip coffee machine, and crockpot.brEnjoy Key West in style and comfort!brbrOld Town Key West is hub of shopping, dining, live entertainment, art galleries, water sports, museums and sightseeing. Within a few blocks you will find: Flamingo Crossing for delicious ice cream; the Rum Bar for amazing frozen drinks and other delights; The Wine Bar for a relaxing drink (right across the street); the Butterfly Museum; La Ti Da Restaurant for a great meal and live entertainment; the Southern Most Beach; and the Southernmost Point iconic buoy.brbrAnd, within a short walk you can enjoy all that downtown Key West has to offer, but you will greatly appreciate coming back to your spacious and peaceful oasis at the end of the day (or night).brbrFor sun-lovers there are: Smather's Beach (free), Higgs Beach; Fort Zachary Taylor Park Beach (pay to park) and the Southern Most Beach (free). And, no trip is complete without a visit to Dante's Pool, where you can hang out in a massive pool with live DJ, full bar, and tasty food.brbrOccupancy is 2 - 8 people. Additional guests over 6 people are 25.00 extra per person per night. There is a four night stay minimum. Prices change according to number of nights, seasons and special event weeks. Five night minimum stay is required during Holiday and Special Event weeks. brbrKeywords: Duval Street, Condo, Old Town, Key West, A Cuban Club, two bedroom

A Duval Street Oasis with balcony overlooking Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$412.77

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: brBegin to relax and unwind as you ferry between two Keys in less than 5 minutes. Feel the soft breezes on your face and your tensions melt away, as you traverse the calm waters between Key West and Sunset Key. brbrUpon arriving at this private island, you will immediately notice the peaceful quiet that car-free, traffic-free living affords. The security and privacy that this island offers make this a great place for families, children, or couples. Upon entering the home via its foliage-lined pergola, you can decide whether to take a dip in the shared pool just steps from the home or enjoy the partial water view from the third-floor covered deck. brbrThis lush island is home to a gourmet restaurant just a few feet from the home, a sunset bar, tennis and basketball courts, spa, and pool. Nightlife on Duval is another attractive option via the island’s 24-hour ferry service. Whether you choose to take day trips from Key West or enjoy its many shops, restaurants, and bars, you can always return to your stress-free vacation retreat on Sunset Key. If you return prior to dark, you will witness the most beautiful sunsets on earth.brbrThis 2-bedroom, 3 baths home sleeps 6 and features 3 levels of living. An open-concept kitchen/living and dining area as well as a full bathroom with walk-in shower are located on the first floor. An office nook is ready for your work or study time. The kitchen also has breakfast bar seating. Whether you prepare cocktails from the bar, read a book on one of the private decks, or enjoy the sunshine on the island’s beach, this escape to paradise is truly special.brbrBED CONFIGURATION:brThe bedrooms are located on the second floor. The primary suite includes a king size bed and ensuite bath with walk-in shower. The second bedroom has two twin beds that can easily be converted to a king and also has an ensuite bath with tub/shower combo. There is a queen sleeper sofa on the first floor along with the third full bathroom, which has a walk-in shower. Not an early riser You won't hear the Key West roosters from this secluded location.brbrOUTDOOR AMENITIES:brA beautiful swimming pool steps away, tennis and basketball courts, spa, private beaches just a few hundred yards away, hammocks, and comfortable lounges complete the outdoor experience.brbrLOCATION: Sunset Key, a private small island minutes from Key West. brbrNEARBY: All the attractions of Key West and Duval Street are just a brief ferry excursion from Sunset Key.brbrPETS: This is not a pet-friendly home. Please view our many other pet-friendly homes!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***Managed by Historic Key West Vacation Rentals***

~The Escape ~ Your own tropical escape on private island!

Key West, Florida, United States

Bed

Bath

Sleeps

$333.88

EXPLORE YOUR MAGICAL GARDEN....brImmerse yourself in this exquisite, adult only, tropical compound of Travelers Palm offering beautiful garden views to refresh your soul. We are only three blocks from all of the fine dining and entertainment of Duval Street, yet tucked away in a private setting that soothes your senses and pushes your worries aside. The ROYAL PALM STUDIO is a traveler's delight that lures you in offering updated tropical furnishings and creature comfort essentials. Enjoy your island getaway in style with a private deck that overlooks tranquil and lush gardens and a pool with a waterfall feature. This cozy unit offers a kitchenette for easy breezy food prep and can sleep 2 people. A contactless check in/out process with a virtual innkeeper allows for a seamless experience! br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES: brYour serenity begins as you step foot into this casual compound with a delightful private porch and conch-style suite that will captivate your island soul. Carry your crafted cocktail to the deck area and pool which comes heated in the winter months, cooled by the protective canopies, exquisite swaying palms and gentle breezes. Stretch out in a deck chair with your favorite mystery novel or toss some kabobs on the shared outside grill for an al fresco treat.brbrSLEEPING ARRANGEMENTS...brEnter the inviting studio where you are greeted by Key West inspired decor, separate bedroom and kitchenette areas, flat screen tv and ample space for unpacking your bathing suits and funwear. This well-lit unit encompasses a bedroom with a newly-remodeled king bed with luxurious bedding, ceiling fan and wall-mounted HDTV. Wash the day off in your private en suite bathroom with enclosed glass and marble tiled shower, quartz sink counter and large bathroom mirror. Slip outside to your private deck to view our botanical gardens that overlook the pool and stone waterfall.brbrPARKING...brParking is offered on a first come first serve basis, and there is plenty of free street parking available if a space is not available upon your arrival.brbrBEACHES...brHiggs Beach is 0.6 mi.brSmathers Beach is 1.9 mi.brFort Zachary Taylor Beach is 1.6 mi. brSouth Beach is 0.5 mi.brSimonton Beach is 1.2 mi.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrYOUR HEAVENLY HIDEAWAY AWAITS YOU...

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Key West, Florida, United States

Bed

Bath

Sleeps

$345.26

This 1-bedroom, 1-bathroom property is located in Key West. The property offers 450 square feet of living space with a private entrance and on-property parking spot. The 1/1 is completely renovated with marble floors, washer and dryer, and A/C units in both the bedroom and the living room. Kitchen is fully fit with a refrigerator, stove top, oven, microwave and dishwasher. Ideal for those seeking a compact living space in a quiet residential area in Key West. First, Last and Security.

Charming private one bedroom in Key West

Key West, Florida, United States

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Bath