Home Vacation Rentals By Owner In Key West, FL

Showing 740 Of 2059 Vacation Rentals
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Exceptional(32)

$452.2

/ Nightly
Condo

Grand Marina Suite - Poolside & Waterfront Condo

Key West, Florida, United States

Summary:brbrA beautiful oceanfront suite located at the best marina in the Keys. Situated on the glistening Atlantic Ocean, our Grand Marina Suite is a tranquil respite with on-site access to boat dockage and world-class fishing charters. Located minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate lodging experience unlike any hotel.brbrbrbrThe Space:brbrGrand Marina Suite is a full two-bedroom suite, with a full kitchen, living room and outdoor lanai. Each of the two bedrooms feature luxurious king sized beds and en suite bathrooms. There is a sleeper sofa in the living room. Outside of the Suite, our guests are encouraged to take advantage of our on-site pool, beach, sauna and fitness center.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrOur property is secluded and private yet minutes away from the excitement of Key West. This condo is located at the private Key West Harbour Marina, in Stock Island, the authentic and revitalized fishing and arts community located directly east of downtown Key West.brbrbrbrGetting Around:brbrArrive by boat, plane or car. On-site golf cart rentals are available, or take advantage of the many taxi and ride-sharing services available for short trips around Key West.brbrbrbrThere are assigned parking spots in front of the Harbour Residences marked as Condo 1, Condo 2, or Condo 3. You have 2 private parking spots located in front of your unit included with your stay.brbrbrbrOther Things to Note:brbr-For the purpose of creating a safe environment for our guests, the exterior of the building is monitored by security cameras.brbr-Please note the onsite restaurant is no longer open.brbr- Not pet friendly
Bed 2

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Bath 2

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Sleep 6

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$779.95

/ Nightly
Private Vacation Home

Casa Rosa: 4BR/4BA house, pool, near Duval

Key West, Florida, United States

Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.brbr*Saturday-to-Saturday Rentals OnlybrbrProperty Overview:brbrPrime Location: brCasa Rosa is situated in a picturesque neighborhood, just one block away from Key West's renowned Duval Street. Casa Rosa is one of the 75 historic eyebrow homes remaining in Key West, Florida. Immerse yourself in the rich local culture with nearby attractions like the Key West Historic Seaport, Ernest Hemingway Home and Museum, the Southernmost Point, and the lively street performances at Mallory Square.brbrbrThe kitchen and dining area overlooks the tropical pool and patio area. The spacious living room, with its plush seating, provides a perfect setting for relaxation or social gatherings.brbrElegant and Comfortable Living Spaces: brCasa Rosa features four beautifully appointed bedrooms and four pristine bathrooms. Two bedrooms have a king-sized bed. The third bedroom has a queen-sized bed. Each room showcases a unique blend of cozy furnishings and tropical-inspired décor, ensuring a restful night's sleep. The fourth bedroom, though more compact, is comfortably fitted with a full-sized bed and is perfect for guests or children, directly accessible through the third bedroom. The Master Bedroom and Bedroom 2 have an ensuite bathroom. The spacious living room, with its plush seating and elegant interior columns, provides a perfect setting for relaxation or social gatherings.brbrbrbrKitchen and Dining Area:brPrepare delicious meals in the kitchen, complete with appliances and ample counter space. There is a Keurig and Mr. Coffee. Adjacent to the kitchen, the dining area offers a large wooden table with seating for eight, ideal for a family dinner or a brunch with friends. brbrbrOutdoor Features: brStep outside to discover a private oasis. The backyard features a swimming pool surrounded by lush tropical foliage, creating a serene environment to unwind or enjoy outdoor dining on the patio. Relax in the hot tub, which is located in the gazebo.brbrbrHighlights Include:br-Master Bedroom: A luxurious retreat with a king-sized bed, ensuite bedroom, and direct access to the pool.brbr-Charming Decor: Wooden floors and pastel-hued walls that echo the laid-back charm of Key West.brbr-Climate Control: Air conditioning brbrbr-Laundry: Washer and dryer available for guest convenience.brbrbrParking:brOne designated parking space is available at the house, suitable for a small compact car. Additional paid street parking is also available nearby.brbrbrExplore the Area: brDiscover the enchanting streets of Key West, dine at exquisite seafood restaurants, or partake in water sports like snorkeling and sailing. The property is also a short walk to the beach, perfect for sunset strolls and day-long relaxation. There are a variety of great ways to explore Key West whether it be by bicycle, pedi-cab, scooter, golf cart, Uber, Lyft, Taxi, or foot. Being in the heart of downtown Key West, many attractions are within walking distance.brbrbrMake Your Reservation: brBook your stay at Casa Rosa today! Don’t miss out on the opportunity to experience Key West from this exquisite home-away-from-home!brbrbrCasa Rosa awaits to provide you with an unforgettable vacation experience, where every detail ensures comfort and the quintessential Key West charm.brbrbrSaturday-to-Saturday Rentals OnlybrCheck-in and check-out are available on Saturdays only. A 7-night minimum stay is required.brbr*Pool heat is available for a fee of $250+ tax per week. Please request at time of reservation or up to one week prior to the reservation start date.brbrbrVACA 20-887 VRA-21-58
Bed 4

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Bath 4

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Sleep 8

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Exceptional(22)

$463.5

/ Nightly
Condo

Grand Marina Suite - Poolside & Waterfront Condo

Key West, Florida, United States

Summary:brbrA beautiful oceanfront suite located at the best marina in the Keys. Situated on the glistening Atlantic Ocean, our Grand Marina Suite is a tranquil respite with on-site access to boat dockage and world-class fishing charters. Located minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate lodging experience unlike any hotel.brbrbrbrThe Space:brbrGrand Marina Suite is a full two-bedroom suite, with a full kitchen, living room and outdoor lanai. Each of the two bedrooms feature luxurious king sized beds and en suite bathrooms. There is a sleeper sofa in the living room. Outside of the Suite, our guests are encouraged to take advantage of our on-site pool, beach, sauna and fitness center.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrOur property is secluded and private yet minutes away from the excitement of Key West. This condo is located at the private Key West Harbour Marina, in Stock Island, the authentic and revitalized fishing and arts community located directly east of downtown Key West.brbrbrbrGetting Around:brbrArrive by boat, plane or car. On-site golf cart rentals are available, or take advantage of the many taxi and ride-sharing services available for short trips around Key West.brbrbrbrThere are assigned parking spots in front of the Harbour Residences marked as Condo 1, Condo 2, or Condo 3. You have 2 private parking spots located in front of your unit included with your stay.brbrbrbrOther Things to Note:brbr-For the purpose of creating a safe environment for our guests, the exterior of the building is monitored by security cameras.brbr-Please note the onsite restaurant is no longer open.brbr- Not pet friendly
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Bath 2

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Sleep 6

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$457.35

/ Nightly
Private Vacation Home

Andros Suite | Perfect Location with Pool!

Key West, Florida, United States

Andros SuitebrbrDiscover Andros Suite, a serene island hideaway just moments from the energy of Duval Street—where the character of Old Town Key West blends seamlessly with a tranquil garden setting, ideal for guests looking to unwind while staying close to it all.brbrThe Space:brAndros Suite features a thoughtfully designed two-story layout that balances comfort and functionality. On the main level, you'll find a cozy living area with a queen sleeper sofa to accommodate additional guests, a convenient half bathroom, and a fully equipped kitchen with updated appliances—perfect for preparing meals at home. Upstairs, the spacious king bedroom serves as a peaceful retreat, complete with a dedicated workspace, generous storage, and a private ensuite bathroom. Filled with natural light and styled coastal touches, this townhome offers a welcoming and relaxing home base for your Key West getaway.brbrGuest Perks:brEnjoy seamless, contactless check-in with a personalized entry code provided prior to arrival. Guests also have access to a shared, lushly landscaped courtyard featuring a heated plunge pool, onsite laundry facilities, and comfortable outdoor seating areas—perfect for soaking in the laid-back island atmosphere.brbrNeighborhood Highlights:brLocated just off the southern end of Duval Street, Andros Suite puts you within easy walking distance of some of Key West's most iconic attractions, including the Southernmost Point, the Ernest Hemingway Home and Museum, and the Key West Lighthouse. You'll also be steps from local favorites like Blue Heaven, Moondog Café, Rams Head Southernmost, and Better Than Sex Dessert Restaurant. From historic landmarks to vibrant dining spots, the best of Old Town is right outside your door.brbrGetting Around:brTake advantage of easy contactless check-in with a personalized access code provided before arrival. Getting around the island is effortless—many attractions are within walking distance, or you can rent a bike, scooter, moke, or golf cart for added flexibility. Rideshare services, taxis, and pedi-cabs are widely available, and street parking can be found nearby on a first-come, first-served basis.brbrOther Things to Note:br- Pet-friendly property! Up to two dogs (40 lb max each) are welcome with a $20 per pet, per night fee.br- Shared washer and dryer available onsite.br- Heated plunge pool located in the shared courtyard.br- Minimum age to book is 25 years old.br- The primary bedroom is located on the second floorbrbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrAt Colocada Vacation Rentals, our goal is to make your Key West stay effortless and unforgettable. If you need assistance or local recommendations, we're always here to help you make the most of your time in paradise.brbrTo promote guest safety, exterior security cameras are in place around common outdoor areas, including pathways, entrances, and the courtyard. No cameras are located inside the home or in private spaces
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Bath 1

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Sleep 4

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$338.48

/ Nightly
Private Vacation Home

KNOT A WORRY so close to Duval at this monthly rental

Key West, Florida, United States

Knot A Worry is a monthly vacation home in the heart of Old Town Key West! Just one block from famous Duval Street, you'll be close to the action but still have a quiet oasis to return to. This house comes fully furnished with all the amenities you'll need for a month or multi-month stay including a private pool, gourmet kitchen, and off-street parking for a small compact car. brbrEnjoy taking in the views of the neighborhood from the second floor front porch and then retire to the private patio and pool where you can catch some rays, grill, or relax in the shade under the covered area. Finish your day with an outdoor shower under the stars to truly live the island lifestyle.brbrInside, the spacious living area features a large flat screen cable TV, dining room table, and lots of comfortable seating with sliding glass doors out to the pool and patio. There is also a first floor half bathroom. The kitchen has granite countertops and a breakfast bar along with full size refrigerator, stove, microwave, toaster, Keurig coffee machine, dishwasher, blender, and all your cooking utensil necessities.brbrUpstairs there are two large bedrooms. The primary bedroom has a king bed, two closets, and a private bathroom with a shower and separate tub. The second bedroom has two queen beds, a closet, and its own bathroom with a shower. The washer and dryer is also located in the second floor hallway.brbrThis property has everything you need to enjoy the ideal Key West vacation. Within close walking distance to incredible restaurants, historic bars, art galleries, cinema, shopping, and grocery and liquor stores, you're sure to fill your days easily. Take bikes for a short ride to the beach, Key West Seaport, or take a relaxed a sightseeing tour. The Duval Loop bus also has a stop right next door and provides free rides around the Duval Street areas.brbrThis is a monthly rental and only rents from the first of the month to the end of the month. We cannot split months.
Bed 2

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Bath 2

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Sleep 6

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Exceptional(74)

$373.67

/ Nightly
Condo

LA CASA CUBANA @ Cuban Club Suites

Key West, Florida, United States

Sitting on the famous Duval Street, this spacious one-bedroom property is so relaxing and beautiful that you will never want to leave! The breezy private balcony is a great place to sit and soak up the rising sun as Duval Street buzzes with morning activity. The loft bedroom upstairs features two comfortable queen beds, a 32 flat-screen TV, two large closets, and a shared nightstand with a reading lamp. The sizable living room is adorned with Cuban art in recognition that the property was built in 1917 as a “club” for Cuban cigar makers. The queen sleeper sofa comfortably accommodates two people, allowing La Casa Cubana to sleep 6 people while still remaining competitively priced. The kitchen features a full-sized refrigerator, oven, dishwasher, toaster, microwave, and coffee maker to do all or none of the cooking while enjoying the island life.brbrYou’ll want to take pictures at the Southernmost Point in the continental United States (only 3.5 blocks away), and fulfill all of your shopping desires at the dozens, if not hundreds, of shops and stores distributed along Duval and the adjoining streets. One block away is Banana Cafe, a fantastic French restaurant for breakfast with crepes, baguettes, and croissants. The sandy shores of South Beach are just 3 blocks away, with the Southernmost Cafe right there for lunch. The best sushi in town is served at Origami, also located one block away. It’s all there for you, so come and enjoy!brbrPLEASE NOTE THAT THIS PROPERTY DOES NOT HAVE A POOL. You may use the pool at Dante’s if you utilize their food and beverage services or you may purchase a day pass using the link below at any of the hotels located near your rental. br brhttps://www.resortpass.com/s/us/fl/key-west/pool search_term=Key+West%2C+Florida&city_alias_id=26
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Bath 1

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Sleep 6

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Exceptional(78)

$493.86

/ Nightly
Cottage

Eyebrow Suite - 2bd/1.5ba Suite off Duval

Key West, Florida, United States

Eyebrow Suite is a spacious two-bedroom suite with one of the best locations on the island. Its large front porch and palm tree-filled fenced-in yard invite you to a private oasis on Olivia street, just a half block from Duval Street. You'll feel like a local as you sip a drink, read the newspaper, or just people watch from the front porch.brbrThis luxuriously appointed unit has been thoroughly renovated while preserving its turn-of -the century historic charm. Furnished with bamboo furniture, bright accents, and Cuban-inspired artwork, the open floor plan offers total comfort and convenience. Each bedroom features a queen bed, TV, and ensuite bathroom which makes it ideal for families and couples traveling together. Although the the second bedroom is only a half bathroom, an outdoor shower awaits on the large private deck just outside the bedroom door. The six-person Jacuzzi, sitting area, gas grill, and spacious living area makes this the ideal property for entertaining family and friends.brbrThis home offers everything you need for the perfect Key West vacation!brbrNote: Parking in Key West is very limited. This property has no assigned parking and is street parking only. You are responsible for finding parking for your vehicle.brbrPLEASE NOTE THAT THIS PROPERTY DOES NOT HAVE A POOL. You may use the pool at Dante’s if you utilize their food and beverage services or you may purchase a day pass using the link below at any of the hotels located near your rental.
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Bath 1

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Sleep 4

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Exceptional(130)

$1027.17

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Private Vacation Home

Spacious Townhome on Windsor Lane 3/3.5

Key West, Florida, United States

Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has been created to meet your every need. The location is perfect; just three short blocks from Duval Street and tucked away on a quiet lane so you can choose your level of activity. The over 1700 square foot townhome is easily accessible to the action of Duval, and yet private and quiet for those wanting peace and tranquility.brbrWindsor Townhomes #3 consists of three ensuite bedrooms, a modern kitchen with high-end appliances, and a generous dining room and family room. The kitchen is fully equipped and has a granite counter and bar top for prepping. Morning coffee may be made using the Keurig or the regular drip coffee maker. The openness of the family room, dining room, and kitchen offers a fantastic space for family and friends to gather before and after experiencing the wide array of activities offered in Key West.brbrOf course, this property comes equipped with great outdoor space that includes a private dipping pool. There is also a gas grill and outdoor dining table on your private deck. The Palms at Windsor truly has everything a group or family needs to enjoy a memorable vacation in Key West.brbrEntering the second floor main bedroom, you will be greeted by a stately king bed and seating area that includes a pull out sofa. The ensuite bathroom is richly appointed with a tiled shower and a dual sink vanity. The additional second floor bedroom includes another king bed and ensuite bathroom with a tub and private balcony. The first floor bedroom contains two twin beds and has a private bathroom with shower. Each bedroom comes with a large flat panel TV and iPhone chargers. brbrThe family room has a flat screen TV and blu-ray DVD to enjoy your own streaming video services. The laundry room with new washer and dryer is on the first floor. The townhome has central air conditioning and heat. brbrCome experience Key West the right way by staying in this luxurious property.brbrThis vacation rental property offers secure, coded keyless entry with contactless check in.brbrBedding: 2 kings, 2 twins, and 1 pullout sofa in main bedroom.brPool Heat included (Nov. thru April).brParking: One off-street parking space.
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Bath 3

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Sleep 8

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Exceptional(161)

$291.28

/ Nightly
Apartment

Hollinsed House Studio - Great Location!!

Key West, Florida, United States

Welcome to Harvey's Haven—a beautiful studio in the heart of Old Town Key West! Conveniently located at the Hollinsed House on Southard Street, one block from famous Duval Street, this ground-floor studio suite is equipped to make your stay on the island comfortable and convenient. Harvey's Haven is both removed from and integrated into Old Town Key West. It is tucked away in a quiet neighborhood, but close enough to walk to any bar, restaurant, shop, or gallery. This is a non-smoking unit designed to accommodate two people.brbrThis charming suite is comfortably furnished with a king bed, comfortable couch, dining table, flat-screen TV, and tropical artwork. Transom windows and an open floor plan create a breezy atmosphere in Harvey’s Haven. The full kitchen features a coffee maker, oven, stove, refrigerator, and the accessories to make any chef happy. A spacious bathroom with standing shower and full-length mirror completes this wonderful accommodation.brbrLush tropical surroundings characterize the Hollinsed House compound. The architecture of this lovely restored Victorian home is complimented by gardens and a courtyard fountain. Relax and socialize in lounge chairs beside the sparkling heated pool or enjoy outdoor dining nestled beneath the swaying palm trees. Harvey’s Haven is walking distance from fine restaurants, bars, clubs, and the best shopping on the island. Just a short bike ride down Southard Street is Fort Zachary Taylor State Park, where the Gulf of Mexico meets the Atlantic Ocean at one of Key West's best beaches. Swim and snorkel, tour the historic fort, bike along the shaded trails, or just kick back and enjoy the spectacular sunset.brbrThe Hollinsed House, with its wraparound porches and gingerbread trimmings, best represents Key West: a blend of history and modernity, smack in the middle of Old Town.This tropical retreat is truly an island oasis!brbrParking in Key West is very limited.  This property has no assigned parking and is street parking only. You are responsible for finding parking for your vehicle. brbrIndividual making the reservation must be 25 years or older with proper identification and be an occupant of the property. The maximum people allowed in this property is 2. If there are more than 2 people are in your party upon arrival, your party will be asked to leave without compensation. Violation of ANY house rules will result in your party being asked to leave without compensation.
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Bath 1

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Sleep 2

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$321.45

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Private Vacation Home

CONCH EASY LIVING -1 block to Duval-Monthly rental

Key West, Florida, United States

Discover Conch Easy Livin' at this monthly vacation home in the heart of Old Town Key West! You'll get a real feel of the Keys in this traditional Conch-style house located just one block from famous Duval Street where you'll be close to the action but still have a quiet oasis to return to. This house comes fully furnished with all the amenities you'll need for a month or multi-month stay including private pool, gourmet kitchen, off-street covered parking, bikes for guests to use, and more!brbrEnjoy taking in the views of the neighborhood on one of the two front porches and then retire to the private garden patio surrounded with lush vegetation, where you can take a dip in the heated pool, catch some rays, grill, or relax in the shade under the covered area. Finish with an outdoor shower under the stars to make the day complete.brbrInside, the spacious dining and living area features a large flat screen cable TV, a dining room table, and lots of comfortable seating with sliding glass doors out to the pool and patio. There is also a first floor bathroom with a shower for your convenience and the living room couch can be converted to a sleeper sofa. The kitchen has granite countertops and a breakfast bar along with full size refrigerator, stove, microwave, toaster, Keurig coffee machine, dishwasher, blender, and all your cooking utensil necessities.brbrUpstairs there are two large bedrooms. The primary bedroom has a king bed, two closets and a private bathroom with shower and separate tub. The second bedroom has two queen beds, a closet, and its own bathroom with a shower. The washer and dryer is also located in the second floor hallway.brbrThis property has everything you need to enjoy the perfect Key West vacation. Just a short walking distance to incredible restaurants, historic bars, art galleries, cinema, shopping, grocery and liquor stores. Take the bikes for a short ride to the beach, Key West Seaport, or enjoy a sightseeing tour. The Duval Loop bus also has a stop right next door and provides free rides around the Duval Street areas.brbrThis is a monthly rental and only rents from the first of the month to the end of the month.  We cannot split months.
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Bath 3

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Sleep 6

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