Vacation Rentals By Owner In Key West, FL

PERFECT TROPICAL POOL RETREAT…brIf you've been searching for the ideal island getaway, look no further. This classic Key West jewel is precisely what your island soul has been yearning to find. This quintessential tropical nest beckons you inside its private gated entrance, where sumptuous living and sultry breezes collide in a perfect storm of blissful pleasure. Tucked into the quiet neighborhood of Midtown, you are close to pristine beaches, White Street Pier, bustling restaurants and a short bike ride to famous Old Town.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brStep inside this oasis where you are surrounded by a privacy fence that encompasses lushly landscaped front and back yards. The serene refuge of this home offers respite after a day of adventure under the southernmost sunshine. Craft your icy cocktail in the modern, fully-equipped and beautifully updated kitchen with a gas range and under counter beverage fridge, then ease onto the cozy furnishings in the adjacent living room and relax with your favorite tv show, a good book or dive into a board game together. The spacious dining room is a perfect setting to share stories over delicious cuisine with your friends and family. This home is equipped with wall mounted Roku enabled SmartTVs in every room and free WIFI. throughout. A washer/dryer is available for your convenience as well. brbrSLEEPING ARRANGEMENTS...brAll of the 4 bedrooms (to include the one in the pool house), offer smart TVs and cooling ceiling fans. The main house features a king bedroom, a queen bedroom and a twin bedroom that can convert to a king bed upon request. The king and queen rooms have desks and a laser wifi printer for those working remotely. The bedroom in the pool house offers twin beds that can also convert to a king (shown as King in photos). Both glass walk-in showers reside in the main house. brbrOUTDOOR LIVING...brThe impressive backyard oasis is a focal point of this spectacular island gem, boasting a sparkling heated pool, al fresco dining table for 10 and seating with sail shade, large propane grill, cooling outdoor shower, cafe table with seating, and pool loungers. It all adds up to an exquisite day under shaded palms and healing sunshine. Sway on the front yard hammock or hop on of of the 5 beach cruisers so you can stroll the charming lanes of Key West to the nearby Pickleball and Bocce courts!brbrPARKING...brThere is off street parking available for this home.brbrPETS...brPets are considered at this home and a pet fee is required. Please include the size/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 offered only as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCANCELLATION...brBookings canceled at least 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).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!brbrTHIS IS YOUR HAPPY PLACE...

BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/ Pool!

Key West, Florida, United States

4

Bed

Bath

8

Sleeps

$525.56

Kingfish Keep | Lively Escape on Duval! Balcony!brbrKingfish Keep is the perfect escape in the heart of the historic district! This charming flat features an upstairs balcony that offers lovely views of the Duval Street, just steps away from shopping, dining, and the beach.brbrThe Space:brKingfish Keep comfortably accommodates up to four guests, ideal for families or friends. Inside, you'll find a cozy kitchenette equipped with a microwave, stove, and fridge, along with a private bathroom and dining area. The property includes a king bed for a restful night's sleep, while the balcony invites you to sip your morning coffee and enjoy some people-watching. This condo is also part of a larger home, Pescado Penthouse, allowing for group rentals if you're traveling with family or friends. Explore the vibrant atmosphere of Duval Street, where you can enjoy fine dining at nearby restaurants.brbrGuest Perks:brThis suite is dog-friendly. Stay connected with complimentary WiFi and two cable TVs. Access is made easy with our digital e-lock system, ensuring a smooth check-in process.brbrNeighborhood Highlights: Kingfish Keep places you at the center of it all! Right on Duval Street, you're just a short walk from the beach and iconic attractions like the famous Southernmost Point. Discover local cafes, shops, and nightlife right at your doorstep.brbrGetting Around: Key West is best explored on foot, but bike and scooter rentals are readily available for those looking to venture further. Rideshare options like Uber and Lyft make getting around the island convenient.brbrOther Things to Note:br- No parking is available on-site.br- Dogs are welcome! One dog (30 lbs maximum) with a $20 per night fee.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt 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.

Kingfish Keep | Lively Escape on Duval! Balcony!

Key West, Florida, United States

Bed

Bath

Sleeps

$454.16

Yellowfin Ledge | Inviting Getaway On Duval! Balcony!brbrYellowfin Ledge is the ideal choice for your Key West adventure! This inviting, dog-friendly condo offers a perfect home base, just moments away from the lively bars, shops, and restaurants of Duval Street. With a kitchenette, two TVs, and complimentary WiFi, you'll enjoy all the comforts of home.brbrThe Space:brYellowfin Ledge features a cozy layout with one comfortable queen bed and a small twin sleeper sofa, making it perfect for couples or small groups. Step out on the balcony and soak in the vibrant atmosphere of the main drag. Central air conditioning ensures your comfort after a day of exploration. This condo is also part of a larger home, Pescado Penthouse, allowing for group rentals if you're traveling with family or friends. Explore local attractions like the Ernest Hemingway House, just five blocks away, or stroll four blocks to relax at Southernmost Point beach.brbrGuest Perks:brEnjoy hassle-free check-in with our secure e-lock system. One small dog (30 lbs or less) is welcome for a nominal fee, making it easy to bring your furry friend along. Please note that parking is not available on-site.brbrNeighborhood Highlights:brYellowfin Ledge is perfectly situated for you to experience the energetic charm of Key West. You'll be within walking distance to an array of cafes, bars, and unique shops, immersing you in the island lifestyle.brbrGetting Around:brKey West is very walkable, but bike and scooter rentals are available nearby for further exploration. Rideshare services like Uber and Lyft are convenient options for getting around the island.brbrOther Things to Note:br- This rental is located on the second floor.br- Parking is not available on the property.br- Dogs are welcome! One dog (30 lbs maximum) with a $20 per night fee.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt 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.

Yellowfin Ledge | Ideal Getaway On Duval! Balcony

Key West, Florida, United States

Bed

Bath

Sleeps

$410.81

Wahoo Way | Charming Hideaway On Duval Street!brbrEscape to Wahoo Way for an unforgettable couple's retreat in Key West! This delightful suite is perfectly situated on vibrant Duval Street, placing you just moments away from the finest nightlife, dining, and attractions the island has to offer. Plus, the iconic Southernmost Point and the beach are just a short stroll away, making it easy to soak up the sun.brbrThe Space:brWahoo Way features a cozy ambiance ideal for couples, complete with a well-equipped kitchenette, including a fridge, stove, microwave, and coffee maker. Enjoy in-room entertainment with cable TV and stay connected with complimentary WiFi. This condo is also part of a larger home, Pescado Penthouse, allowing for group rentals if you're traveling with family or friends.brbrGuest Perks:brEnjoy the convenience of seamless, contactless entry with our digital E-lock system. This pet-friendly suite welcomes one small dog (30 lbs or less) to accompany you on your getaway. Please note that parking is not available on-site.brbrNeighborhood Highlights: Wahoo Way is centrally located right on Duval Street, allowing you to easily explore the vibrant culture of Key West. Just steps away, you'll find a variety of cafes, bars, and shops, all set against the backdrop of the island's unique charm.brbrGetting Around: Key West is best experienced on foot, but bike and scooter rentals are available nearby for those looking to explore further. Rideshare services like Uber and Lyft are also convenient options for getting around.brbrOther Things to Note:br- This suite is located on the second floor.br- Please inquire about parking options if needed.br- Dogs are welcome! One dog (30 lbs maximum) with a $20 per night fee.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt 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.

Wahoo Way | Charming Hideaway On Duval Street!

Key West, Florida, United States

Bed

Bath

Sleeps

$1225.05

Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!brbrPescado Penthouse is the ultimate getaway for families or friends seeking adventure in Key West! This unique property combines three charming condos—Kingfish Keep, Wahoo Way, and Yellowfin Ledge—into a single rental, providing ample space and convenience right in the heart of the historic district. With stunning views from the balconies and just steps away from the vibrant energy of Duval Street, you'll have easy access to shopping, dining, and the beach.brbrThe Space:brThis expansive rental comfortably accommodates up to nine guests, making it perfect for larger groups. Kingfish Keep features a king bed, a double sleeper sofa, and a cozy kitchenette, while Wahoo Way offers an additional king bed, both ideal for couples or small families. Yellowfin Ledge completes the trio with its inviting atmosphere, a comfortable queen bed, and a small twin sleeper sofa. Each condo includes its own private bathroom, ensuring everyone has their space. Enjoy morning coffee or evening cocktails on the balconies, taking in the lively sights and sounds of Duval Street.brbrTraveling with a smaller group Each of the three condos that make up Pescado Penthouse can be booked individually as well. Explore these unique spaces for the perfect Key West getaway! brbrKingfish Keep - https://www.colocada.com/rentals/kingfish-keepbrWahoo Way - https://www.colocada.com/rentals/wahoo-waybrYellowfin Ledge - https://www.colocada.com/rentals/yellowfin-ledgebrbrGuest Perks:brExperience the ease of contactless entry with our digital e-lock system for all units. The property is dog-friendly, allowing two small dogs (30 lbs or less) to join your stay for a small nightly fee. Stay connected with complimentary WiFi and unwind with cable TV in each unit.brbrNeighborhood Highlights:brPescado Penthouse places you at the center of it all! With Duval Street just outside your door, you're a short walk from the beach and iconic attractions like the Southernmost Point. Discover local cafes, bars, and shops, immersing yourself in the unique charm of Key West.brbrGetting Around:brKey West is best explored on foot, but bike and scooter rentals are readily available for those looking to venture further. Rideshare options like Uber and Lyft make getting around the island convenient.brbrOther Things to Note:br- This rental is located on the second floor.br- No parking is available on-site.br- Dogs are welcome! Two dogs (30 lbs maximum) with a $20 per night fee.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt 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.

Pescado Penthouse | Vibrant Retreat on Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$739.28

All rentals will be in seven-night increments with a Friday through Sunday for check-in. brbrThank you for choosing Dash Realty Group of Windermere, Florida. We are a registered Fla. Seller of Travel Ref. No. ST42435. brbrWith a stay at Hyatt Residence Club Key West, Sunset Harbor in Key West (Old Town), you'll be steps from Harry S. Truman Little White House and 4 minutes by foot from Duval Street. This condo is 0.2 mi (0.4 km) from Mallory Square and 0.2 mi (0.3 km) from Key West Shipwreck Museum.brbrMake yourself at home in one of the 92 air-conditioned rooms featuring refrigerators and microwaves. Satellite programming and DVD players are provided for your entertainment, while complimentary wireless Internet access keeps you connected. Private bathrooms have complimentary toiletries and hair dryers. Conveniences include safes and coffee/tea makers.brbrTake advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless Internet access and concierge services.brbrBeginning 2026, the resort will charge $75 per tidy-up service request. Towels will be changed at no cost, but you must call the front desk to request. brbrBooking through VRBO is fast and easy. Dash Realty Group/ DashWeek will email you the updated confirmation once you book through VRBO. Please note that VRBO provides an instant quote that may not be accurate and may require us to send an adjusted price quote and adjusted dates based on what is available for your requested dates.brThis is based on higher demand weeks and resorts that may be higher than the initial quote. The VRBO calendar does help provide instant availability and estimated price quotes. However, because availability and rates vary constantly, the calendar feature and instant quote feature is not always 100% accurate. brbrThe photos are a good representation of what your villa will look like. Layouts may vary. The resort updates and maintains the villas at this resort and your villa is assigned upon check-in. Views will vary, resort views are standard, ocean views are priced higher and the view will vary depending upon the location of your villa. We cannot guarantee the quality of your view.

Hotel Resort

Hyatt Sunset Harbour Resort-Prime location on Key West!!

Key West, Florida, United States

Bed

Bath

6

Sleeps

$363.1

Consider this cottage your home away from home while you visit Key West. This pet friendly property features 2 bedrooms with king beds, 2 bathrooms, one with a jetted bathtub, a newly renovated kitchen and all the necessary amenities for a comfortable stay. Whether you're looking to unwind in the cozy living space or explore Key West, this cottage is the perfect retreat for guests. We hope you enjoy what our place and Key West has to offer.

Cottage

Charming pet friendly 2 bed/2 bath cottage 3 blocks from Duval

Key West, Florida, United States

Bed

Bath

4

Sleeps

$502.19

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrIt is not so often that something new is built in Old Town, the historic district of Key West known for quintessential conch homes and walkable streets. But recently a spectacular development called Old Town Villas was constructed smack dab in the middle of Old Town. SEAPORT SENSATION is one of the newly built breathtaking townhomes at Old Town Villas that allows you to enjoy the luxury of brand-new construction in the prime location you've been searching for. Typically, a prime location comes with noise, but not with this newly constructed home - you cannot hear a sound from inside! Other benefits of renting SEAPORT SENSATION include:brbr** Three spacious bedrooms, each with an en suite bathroombrbr** A private elevator reaching ground floor to top floorbrbr** Access to the large community poolbrbrAlso included with your rental is Last Key Realty's Five Star Guest Services, known for providing memorable Key West vacations. You couldn't fathom a better vacation home to experience all that Old Town Key West has to offer.brbrTHE LOCATION...brbrOld Town Villas is a unique gated community just developed in a prime area of Old Town Key West. There are 20 townhomes with one large shared pool, all accessible by electronic gates to which you will have your own key. You'll be in the epicenter of Key West, just steps from local favorites like A&B Lobster, Sloppy Joe's, and Schooner Wharf. Ride bikes to Fort Zachary Taylor State Park Beach, just a half-mile down the road. While you won't need a car to get around, your private two-car garage provides off-street parking.brbrTHE COMMUNITY POOL...brbrSoak up the sun at the large Community Pool, located just steps away from your front door. There are chaise lounges surrounding the pool for your comfort and a large cabana with restrooms for your convenience.brbrTHE LIVING AREAS & KITCHEN...brbrUse the private elevator to access every level of this home without the use of stairs. The first living level features a sitting room, dining area, and a top of the line gourmet kitchen. The sitting room has a large flat screen SMART TV, comfortable seating options, and a balcony. The gourmet kitchen has beautiful granite countertops and is fully equipped with stainless steel appliances and all of the tools needed to prepare a meal from home.brbrHop in the elevator (or get your steps in using the stairs) and head up to the top floor where you'll find the main living area with soaring vaulted ceilings, a large flat screen SMART TV, and plenty of comfortable seating. This living room also includes a full wet bar, a convenient half bathroom, and a large outdoor terrace, complete with outdoor seating and dining.brbrTHE ACCOMMODATIONS...brbr** First Master Suite: Located on the Third Floor with a King bed and an en-suite bathroom with dual sinks, a garden tub, and a shower.brbr** Second Master Suite: Located on the Third Floor with a King bed and an en-suite bathroom with a large glass shower.brbr** Third Bedroom: Located on the Second Floor with Two Twins OR One King bed and an en-suite bathroom with a shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat & A/Cbr** Ceiling Fansbr** Flat Screen State-of-the Art HD TVs in all bedrooms and main living areabr** Fully Equipped Chef's Kitchen with Stainless Steel Appliancesbr** 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** Community Pool Accessbr** Private Elevatorbr** Off-Street Parking in Private 2 Car GaragebrbrOther notes:brbr** In person welcome when possible, after hours check in availablebr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** This property will accommodate 8 adults

**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$299.32

Summary:brbrRunaway Bills- 2 BDR Main house with 1 BDR Cottage and pool in the Key West downtown.brbrbrbrThe Space:brbrThis charming and stylish Conch home is tucked away on a quiet lane in the heart of Old Town Key West, offering the perfect island retreat. Surrounded by historic architecture and vibrant neighborhoods, this inviting property is just a short stroll from the famous Duval Street, placing you within easy walking distance of restaurants, galleries, shops, and nightlife.brbrbrbrThe main house features two comfortably sized bedrooms, each with king beds, and one full bathroom. Beautiful hardwood floors throughout create a warm coastal character that blends perfectly with the relaxed Key West atmosphere. The fully equipped chef’s kitchen is ideal for guests who enjoy cooking, while the open living area flows seamlessly to a covered outdoor dining space overlooking the pool and deck, perfect for entertaining or relaxing.brbrbrbrAcross the pool, a separate pool house cottage provides additional privacy and includes a third bedroom with a full-size bed, a half bath with toilet and sink, and a private outdoor shower, creating a unique tropical guest suite.brbrbrbrThe fully fenced backyard surrounds a refreshing swimming pool and sun deck, offering a private oasis where guests can unwind after a day exploring the island.brbrbrbrPets are welcome with a non-refundable pet fee, and the property includes the rare convenience of two assigned parking spaces.brbrbrbrAdditional Featuresbrbrbrbr• Central air conditioning and ceiling fans throughoutbrbr• Washer and dryerbrbr• Wireless high-speed internetbrbr• Linens, bath towels, and pool towels providedbrbr• Fully stocked kitchen with cookware, dishes, flatware, and glasswarebrbr• Starter supply of paper and cleaning productsbrbr• Outdoor showerbrbr• Optional housekeeping services availablebrbrbrbrSleeping ArrangementsbrbrbrbrRoadside Bedroom – King BedbrbrMiddle Bedroom – King BedbrbrLiving Room – FutonbrbrPool House Bedroom – Full BedbrbrbrbrThis peaceful yet centrally located home offers the best of Key West living—a private tropical setting just minutes from the island’s most iconic attractions.brbrbrbrGuest Access:brbrE- lock code will be providedbrbrbrbrThe Neighborhood:brbrThe home is located in the heart of Old Town Key West, one of the island’s most charming and historic neighborhoods. Known for its colorful Conch-style homes, tropical landscaping, and laid-back island atmosphere, Old Town captures the authentic spirit of Key West.brbrbrbrJust a short walk away is the world-famous Duval Street, where you’ll find an exciting mix of restaurants, cafés, art galleries, boutiques, and lively nightlife. Guests can enjoy everything from waterfront dining and sunset cocktails to local music and cultural attractions.brbrbrbrThe neighborhood is also close to beautiful beaches, historic landmarks, and parks, including Fort Zachary Taylor Historic State Park, known for its scenic shoreline and excellent snorkeling. Despite being near all the activity, the surrounding streets remain quiet and residential, offering a peaceful retreat after a day exploring the island.brbrbrbrWith its walkable streets, tropical charm, and vibrant local culture, Old Town Key West is truly the perfect place to experience the island lifestyle. brbrbrbrGetting Around:brbrGetting around Key West is easy and part of the fun of visiting the island. Most guests enjoy walking or biking, as many of the main attractions, restaurants, and shops are within a short distance. From the home, you can easily stroll to Duval Street and explore Old Town at a relaxed pace.brbrbrbrBicycles and golf carts are also very popular ways to get around and can be rented nearby. Taxis and rideshare services are readily available, and the Duval Loop shuttle provides a convenient free service throughout much of Old Town. With the island being just a few miles long, it’s simple to explore everything Key West has to offer. brbrbrbrInteraction with Guests:brbrSelf check in

Runaway Bills

Key West, Florida, United States

Bed

Bath

Sleeps

$577.36

Please call or text if you’d like to book our home br702 232... 3750brbrWhen booking our home please include a brief description of who you’ll be traveling with and what brings you to the area with your reservation request. We like to know who will be staying in our home brbrWelcome to your front row seat of the New Truman Waterfront Park with water views and beautiful sunsets right from our porch. There are only a few homes in the Shipyard with a view like this! Most of the Shipyard has views of other units balconies and aren’t as private. There really is nothing like sitting on our balcony and watching the activity at the park and the ocean. brbrIf you're coming for any of the events that Key West offers you can see the parades from our balcony! Fantasy Fest, Speed Boat races and many others are right in front of you.brbrWelcome to your home away from home and enter through the canopy of trees to the secure, patrolled Shipyard Condominium's in the desirable Truman Annex Complex. We are one of the few in the Shipyard with an ocean view. Professionally designed to maximize relaxation and encourage adventure.brbrRelax on the balcony with your glass of wine and you're bound to see a cruise ship, sailboat or parasailer pass by. It's the perfect seat to watch the parades or boat races. Fort Zachary Taylor State Beach is a 2 minute bike ride away. This wonderful home has been newly decorated with a beach chic theme, comfortable outdoor furniture, professionally designed bedrooms with new queen beds in each room , fully stocked kitchen, living room, washer/dryer. Some of the amenities include WIFI, SMART TV's, and an assigned parking spot . Steps from the world famous Duval Street, sunset celebration and all the downtown action one desires. You are only one block down from The Green Parrot, rated the 3rd best bar in America. The Shipyard is the closest residential location to Fort Zachary State Park and Beach. You are in the heart of Old Town, Mallory Square (sunset celebration) and on the grounds of Harry Truman's Little White House located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are landscaped with 30’ palms and exotic flowering plants. It is just a short stroll to the Historic “Little White House” where President Truman called home whenever he could. You are close by the warm tropical waters of the Gulf of Mexico where you can hop on a fishing boat for flats or deep sea fishing, take the Ferry to Sunset Key for lunch or dinner, go parasailing, snorkeling, diving, shopping, dining or wherever your dreams might take you. Just another short stroll takes you to Mallory Square where the world renowned “Sunset Celebration” occurs every day! This event is a “don’t miss” of things to do in Key West.brbrWe provide all of your kitchen essentials, just bring the cook, spices, and the food! Spacious living room where the living room doors open up into the private deck making your vacation a true Tropical experience.brbrbrWhat is provided:brbrWe provide 1 towel and wash cloth per guest listed in the reservation; if this is not enough please bring your own. brbrWe provide 2 rolls of toilet paper and 1 roll of paper towels per reservation. Please bring extra if this is not enough.brbrDaily maid service is not provided.

Key West Rooster

Key West, Florida, United States

Bed

Bath

Sleeps

$656.1

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. This two bedroom Villa Vista is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. brbrThe number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West. br1/2 block to Hard Rock Cafebr2 blocks to Margaritavillebr2 blocks to Sloppy Joe’sbr3 blocks to the Historic Seaportbr4 blocks to Mallory Squarebr4.5 blocks to Schooner Wharfbr6 blocks to Hemingway’s HousebrbrEmail us for availability, even if we look full. Please be aware of scams asking for wire transfers or offers from Craigslist. If you have any questions, please call our reservations desk.

Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$335.19

Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and dining area. The living room features comfy furniture and a panel TV. One queen bedroom and one twin bedroom. Enjoy outdoor dining on the brick patio surrounded by a tropical landscape. brVilla Fleur is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former U.S. Navy property of Truman's Little White house. Just steps from Duval St. and located near the Ft. Zach beach and Hemingway's house, all of Old Key West's sites are within easy walking distance. Our private oasis can be your tropical retreat. brbrCOVID-19 UPDATE after May 1, 2020. Please note our 60 day refund policy. We will no longer offer a cash refund after the 60 day period has passed. We will offer a credit if local authorities issue travel restrictions that prevent your visit to Key West.

Villa Fleur at Shipyard Condominiums

Key West, Florida, United States

Bed

1

Bath

4

Sleeps

$577.25

SOUTHERN CROSS:brWelcome to this charming home in Bahama Village - Old Town Key West. This modern and elegant home was constructed in 2021 and features 3 bedrooms, 3.5 baths, off-street parking, and your own private pool! Available for rental stays of 28 days or longer, this home is perfectly situated in the heart of Old Town Key West. Guests are just 1.5 blocks to iconic Duval Street which features some of the best shopping, restaurants, and live music in the country. You're 2 blocks to the historic Key West Lighthouse and Hemingway House Museum, and 3.5 blocks to Southernmost Point or Key West's best restaurant...Blue Heaven!brbrDETAILS & AMENITIES:brEnjoy the enchanting atmosphere of this home which features the perfect blend of luxury, comfort, and island living! The home is complete with modern amenities like a private swimming pool, air conditioning, WiFi, a gas grill, two sets of washers & dryers, tankless hot water heaters for long & relaxing showers, ceiling fans in each bedroom, an EV charging station, and off-street parking, The bright, open layout also features impact-rated doors and windows, solid wood cabinetry, Dade County pine floors, quartz countertops, and professional-grade Viking appliances in a chef's dream kitchen. Each bedroom is spacious and filled with natural light, while the bathrooms are elegantly appointed and strategically placed for convenience--including a half bath with outdoor access, perfect for poolside guests.brbrSLEEPING ARRANGEMENTS:brThis home features a king bedroom suite on the main level with its own private bathroom. The master bedroom suite is upstairs and features a king bed with a large tiled shower with glass surround. The third bedroom suite is also on the second level and contains a full bed and a twin bed...also with its own private bathroom. A half bath is located on the main level and is perfect for pool guests or simple convenience. brbrOUTDOOR LIVING:brEnjoy the best of island outdoor living with a private concrete swimming pool, covered front and rear porches with composite decking, and a gas grill for delicious cookouts.brbrPARKINGbrThis home has two designated off-street parking spots in the front driveway. There is also ample on-street parking in the neighborhood if you have extra guests.brbrPETS:brThis home allows small dogs only.brbrBOOKING DATES:brThe home is only available as a monthly rental (28 night minimum).brbrCANCELLATION:brBookings canceled at least 60 days before the start of the reservation will receive a 100% refund. Cancellations inside of 60 days are non-refundable.

SOUTHERN CROSS: 3 BR, 3.5 BA home in Old Town Key West with Private Pool & AC!

Key West, Florida, United States

Bed

Bath

Sleeps

$1371.38

Key West is waiting for you at this superb 4-bedroom resort. Fresh and new inside and out, With 2 king beds, 1 queen bed, 2 twin XL beds, and 1 futon, guests will have plenty of space to relax. The 4 bathrooms feature a large pool and private back deck tub, 4 showers, and jetted bathtubs for a terrific stay. It's easy to see why you'll be able to unwind at our place. Excellent location just a couple blocks from Southern buoy and Duval. Play pickle ball and lounge on the beach just 2 blocks. Includes 4 bikes

4-bedroom resort style home in awesome Key West with large pool and private deck

Key West, Florida, United States

Bed

Bath

Sleeps

$702.89

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom villa is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. brbrThe number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West. br1/2 block to Hard Rock Cafebr2 blocks to Margaritavillebr1 1/2 blocks to Sloppy Joe’sbr3 blocks to the Historic Seaportbr4 blocks to Mallory Squarebr4.5 blocks to Schooner Wharfbr6 blocks to Hemingway’s HousebrbrEmail us for availability, even if we look full. Please be aware of scams asking for wire transfers or offers from Craigslist.

Rose Lane Villas - Villa Alta - 1 bedroom - Sleeps 2 - Downtown Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$390.06

STUNNING KEY WEST RETREAT…brJust renovated, this island gem exudes the utmost island spirit with authentic historic character. Meticulously preserved with the finest of luxuries, the blissful functionality of this home exceeds a standard of excellence that cannot be missed. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brA charming glance to a picture-perfect front porch greets you to this peacefully located cottage. Walls wrapped in rich Dade County Pine draw you in as you enter this aesthetically pleasing, modern abode. Breathtaking at first glance, the open Great Room boasts high, open beam cathedral ceilings with wood flooring and modern décor throughout. Large sliding doors beyond a cozy seating area with a flat screen smart TV with streaming capabilities can be perched open creating an inviting indoor/outdoor gathering space. Pristine detail lies at every end of the bright kitchen equipped with top of the line appliances, island bar seating for 2 and banquette dining seating that overlooks your tropical paradise. brbrSLEEPING ARRANGEMENTS…brDiscover opulent comfort in the downstairs king master suite furnished with a flat screen TV, storage space for all your belongings and a lavish en suite full bathroom showcasing exquisite décor, a double sink vanity and a glass walk in shower. Follow the stairs above to a guestroom with two twin trundle beds, one of which creates a king bed. Steps down the hall lies another king guestroom with a cheerful queen sleeping nook. Both rooms share a hallway full bathroom equipped with a walk in glass shower. The downstairs sofa sleeper pulls out to a queen bed with convenience to a nearby full bathroom with a walk in glass shower. brbrOUTDOOR LIVING…brLook no further than this incredibly peaceful outdoor sanctuary to find your zen. A retractable awning allows for ample shade resting over a seating area overlooking the heated dip pool and tranquil waterfall. Rinse off in the outdoor shower and take evening strolls through the attractive setting of the highly coveted neighborhood of “The Meadows.” 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...brDogs considered, but no cats or other animals please. 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. A pet fee is required.brbrMULTI MONTH RESERVATIONS...brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay clean brPool/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). brbrPICTURE PERFECT…

WANDERLUST ~ Stunning 3 Bed, 3 Bath Retreat in Peaceful Neighborhood w/ Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$536.29

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.brbrbrbrStunning 2-Bedroom Ocean-View Oasis at 1800 Atlantic – Key WestbrbrWelcome to your perfect tropical escape! This beautifully maintained, family-owned 2-bedroom, 2-bath vacation rental at the prestigious 1800 Atlantic in Key West offers breathtaking ocean views and all the comforts of home.brHighlights of Your Stay:brbr Spacious Accommodations:brbr Master Suite with a new king bedbr Guest Bedroom with a brand-new king bedbr Queen sleeper sofa in the living roombrbr Island-Inspired Interiors:brbr Bright Mexican tile flooring enhances the coastal vibebr Fully renovated kitchen (2022) with modern amenitiesbrbr Resort-Style Amenities:brbr Olympic-size heated pool overlooking the Atlanticbr 20-person Jacuzzi tubbr Tennis courts, including the only clay court in Key West and two additional hard courtsbrbr Unbeatable Location:brbr Directly on the Atlantic Ocean, next to Smathers Beachbr Just minutes from Key West’s historic district, famous for its bars, dining, and entertainmentbr Easily accessible by car (5 mins) or bike (10 mins)brbrParking & Connectivity:brbr Free assigned parking for one regular-sized vehicle — no extra fees!br High-speed internet access includedbrbrWhether you're relaxing poolside, hitting the beach, or exploring the vibrant local scene, our ocean-view condo is your perfect home base. Call us or stop by our office — we’re always happy to share local tips and favorite hidden gems.brbrWe look forward to welcoming you to paradise — we’re confident you’ll be back again!

Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals

Key West, Florida, United States

Bed

Bath

Sleeps

$464.66

This listing is for a room within a hotel.brbr✦ Your room is 200 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Street parking – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. extra charge of $50 per nightbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Hotel

Room w/ Queen Bed in Vibrant Key West! Enjoy Romantic Ambience near Attractions

Key West, Florida, United States

Bed

Bath

Sleeps

$456.75

This listing is for a room within a hotel.brbr✦ Your room is 320 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Street parking – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. extra charge of $50 per nightbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Hotel

King Bed Room in the Heart of Key West! Perfect for Friends & Couples Vacation

Key West, Florida, United States

1

Bed

1

Bath