Vacation Rentals By Owner In Key West, FL

Welcome to Coral Oasis, a charming 3-bedroom townhouse nestled in a gated community just over Cow Key Bridge from Key West! brbr brbrEnjoy the best of both worlds—a peaceful retreat with easy access to the excitement of Duval Street, pristine beaches, and world-famous attractions just minutes away! Step inside to find a spacious, well-appointed home designed for comfort and relaxation. The open living area is perfect for unwinding after a day of island adventures, while the fully equipped kitchen makes dining in a breeze. Each bedroom offers a cozy retreat, ensuring a restful night's sleep. Outside, soak up the Florida sun at the shared heated pool, or take a short drive to nearby beaches, marinas, and waterfront dining. With off-street parking for up to two vehicles and pet-friendly accommodations, Coral Oasis is ideal for families, couples, or friends looking to experience the Keys in style. Book your stay today and enjoy the perfect blend of convenience, comfort, and island charm at Coral Oasis! brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1 (Upstairs): King Bed, En-Suite Bathroom, Smart TV brbr brbrBedroom 2 (Upstairs): King Bed, En-Suite Bathroom, Smart TV brbr brbrBedroom 3 (Downstairs): Queen Bed, Smart TV brbr brbrLiving Room: Sectional Sofa, Smart TV brbr brbrKitchen: Nicely Equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Heated Pool brbr brbr- Two Parking Spaces brbr brbr- Keurig, Drip Coffee Maker, Toaster brbr brbr- Linens and towels (bath and pool) provided brbr brbr- 3 miles to Smathers Beach brbr brbr- 4 miles to Duval Street brbr brbr- 4.5 miles to Southernmost Point brbr brbr- 4.5 miles to Key West Historic Seaport brbr brbr- 5.1 miles to Mallory Square Sunset Pier brbr brbr- 5.2 miles to Fort Zachary Taylor State Park Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPet Policy: Up to two friendly and well-behaved dogs 25 LBS or less will be considered with a $30/night pet fee and pet registration with the HOA. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, two exterior security cameras monitor the front porch and back porch. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

Coral Oasis – Spacious 3BR Retreat, Shared Pool, Dog Friendly, Parking, Minutes to Downtown Key West

Key West, Florida, United States

Bed

Bath

6

Sleeps

$205.4

Enjoy below deck life during a one of a kind stay on Stock Island. Our sailboat offers a unique twist to a typical vacation rental. Docked at The Perry Resort and Marina, with shore power, ice cold A/C, and all amenities of a 4-star resort (pools, restaurants, a free shuttle, parking, and a gym).brbrMinutes from downtown Key West presents the ability to enjoy what the island has to offer, while keeping a quaint escape from the chaotic day to day bustle. Enjoy nature at this unforgettable escape.brbrThe spacebrBOAT:brbr-The king-size main bed has room to sit up against the headboard. This bed sleeps 2 guests.brbr-The secondary bed is a V-Berth at the Bow of the boat, depending on the guests' heights, potentially needing to be folded out for more room. The V-Berth bed can sleep an additional guest if needed.brbr- Access onto the boat and into the cabin can be difficult for some people who are older or have disabilities, so please consider that before booking a sailboat.brbr- The kitchenette has a mini fridge for food and drinks. A coffee maker is also on board with many pod options. A grill is installed on the back deck for your convenience.brbr- The bathroom has a marine toilet with instructions for use onboard and a sink/shower head without hot water. This is a tiny area to shower, however, and I commonly suggest using the marina shower options instead. These are clean and modern showers with several located throughout the marina. Guests will be given codes to access the gates and all facilities.brbrGuest accessbrPrivate Gated Marina Community - Guests have access to pools, marina washrooms, bar, restaurant, and a gym.brbrOther things to notebrPlease note this is a well kept and recently updated sailboat and not a Luxury Yacht. This unique stay offers an affordable option for a typical destination vacation with high end resort amenities. Amenities include 2 nice pools, a fire pit, 2 restaurants, an ice cream and coffee shop, a convenience store, a gym, and to top it all off, a free shuttle to downtown KW, leaving on the hour between 9am - 10pm. It’s also a functioning marina, so besides other rentals and foreign sailboat charters, day-to-day traffic does occur.brbrAsk us about taking the sailboat or the small sandbar boat out for charters! While I am unable to include charter prices in the nightly rate, I am able to offer them as an add on at a great discount for guests staying on the boat. Charters are completely optional, you do not have to charter the boat out and are welcome to stay on it as an accommodation only in the marina/resort as well.

House Boat

Key West Sailboat Getaway

Key West, Florida, United States

Bed

Bath

Sleeps

$456.56

Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon became the center of social and community life for the Cuban population in Key West. After the original Cuban Club burned down in 1983, it was restored and converted to luxurious and spacious suites. brbrEscape the stress and cares of your daily life with a vacation to the wonderful Cuban Paradise! This roomy two-bedroom condo has a private balcony to enjoy all the hustle and energy of the famous Duval Street. The primary bedroom sits in a loft overlooking the living room, and it features a four-post queen-sized bed, two nightstands with reading lamps, an alarm clock, private ensuite bathroom, large closet, and a small electronic safe. Located downstairs is another bedroom with a queen-sized bed, private ensuite bathroom, a nightstand with reading lamp, large closet, and a flat-screen TV. brbrThe expansive living room features two plush sofas (one of which folds into a sleeper sofa), a coffee table, glass kitchen table with six comfy chairs, and a flat-screen TV. If cooking is your passion, then you’ll love the fully-stocked kitchen, which includes a full-size refrigerator, dishwasher, stove, coffee maker, toaster, and microwave.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 Street and the adjoining streets. brbrOne block away is Banana Cafe, a fantastic French restaurant for breakfast with crepes, baguettes, and croissants. The sandy shores of South Beach are just three 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

Condo

Escape to the wonderful Cuban Paradise!

Key West, Florida, United States

Bed

Bath

Sleeps

$744.46

The Penthouse at Custom House Inn | Serene Coastal Escape on Duval Street!brbrImmerse yourself in the calm and comfort of Key West at The Penthouse, a spacious and stylish suite at the Custom House Inn, located right on the lively 100 block of Duval Street. This modern maritime retreat blends coastal elegance with understated luxury, offering the perfect setting for your island getaway. With its soothing muted tones, minimalist design, and unbeatable location, The Penthouse invites you to relax, recharge, and experience the very best of Key West.brbrThe Ambiance:brStep into The Penthouse, a refined 3-bedroom, 3-bathroom suite designed with earthy hues, clean lines, and nautical touches that echo the tranquility of the sea. Ideal for up to six guests, this expansive unit features:brbr- Three private bedrooms, each with a plush King-sized bed and serene coastal decorbr- Three sleek, modern bathrooms with walk-in glass showers and soft ambient lightingbr- A stylish living room with comfy seating and a smart TV for unwinding after a day in the sunbr- A minimalist kitchen equipped with essential appliances, perfect for light meals and morning coffeebrbrEnjoy shared access to the covered balcony, where a cozy sectional awaits for you to sip cocktails or simply enjoy Key West vibe. Located on the second floor with stair access, this suite is the ideal blend of peaceful retreat and prime location.brbrGuest Access:brOur streamlined, contactless check-in system makes arrival a breeze. You'll receive personalized access codes prior to your stay—no lines, no waiting, just walk in and start soaking up the Key West sun.brbrThe Neighborhood:brSituated in the vibrant heart of Old Town Key West, The Penthouse places you just steps from some of the island's best restaurants, bars, and attractions. From iconic watering holes like Irish Kevin's and Fat Tuesday's to the legendary Hemingway House and Southernmost Point, everything is within walking distance.brbrGrab breakfast at Moondog Café, lunch at Fogarty's, and enjoy the nightlife just outside your door. Whether you're here for the culture, the cocktails, or the sunsets, The Penthouse puts you at the center of it all.brbrGetting Around:brKey West is best explored like a local—on foot, by bike, or via scooter. Rent a golf cart for a fun ride around the island or hop into a pedi-cab for a breezy cruise. Prefer a quick ride Uber, Taxi, and Lyft are always available. Need insider tips Just ask—we're happy to share our favorite spots!brbrParking Information:brPlease note: there is no on-site parking at the Custom House Inn. Nearby paid parking options include:br- Fleming Street Pay-to-Park Lot (closest option)br- 204 Simonton Streetbr- Caroline Street Outdoor Parking Lotbr- Park N Ride Old Town GaragebrbrOther Things to Note:br- For larger groups, reserve additional suites at Custom House Inn to accommodate up to 20 guests.br- The exterior of the property is monitored by security cameras for your safety and peace of mind.br- This unit is on the second floor (no elevator access).br- No washer/dryer on-site.br- No pets allowed.br- Guests must be 25 years of age or older to reserve this property.brbrCheck-in time: 3:00PMbrCheck-out time: 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrBook your stay at The Penthouse at Custom House Inn and enjoy the perfect mix of style, space, and seaside serenity—right in the heart of Key West.brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Apartment

The Penthouse at Custom House Inn | New!

Key West, Florida, United States

Bed

Bath

Sleeps

$549.57

Tropical Cottage is a quintessential 1930s-era Conch bungalow, lovingly renovated with contemporary island elegance. The sage-green exterior blends Caribbean and Victorian influences: crisp white trim, abundant windows, and black Bahamian shutters. This charming cottage is set back from the street and shaded by gardens, mature palms, and gumbo limbo trees in a quiet, upscale, gated enclave of six historic Old Key West vacation rentals. The spacious pea-gravel courtyard boasts tropical landscaping, coral and rock hardscaping, and stone walkways leading to the shared pool area.brSip Cafe Cubano on the private back deck as Caribbean breezes rustle palm fronds. Prepare a home-cooked meal in the modern kitchen. Dine alfresco when nights are fragrant with jasmine and frangipani. Relax poolside with a Margarita. The central common area, with a pool, picnic tables, and gas grill, is shared by guests of this upscale enclave. There’s also a shared laundry area with commercial washers and dryers.brStroll to great seafood, fine dining, beaches, and iconic attractions like the KW Butterfly & Nature Museum, Southernmost Point, Higgs Beach, and West Martello Tower. After a day at the beach, shower off in either of two hot-water outdoor showers. Street parking is available. Tropical Cottage is ideal for families, groups of friends, couples, and snowbirds. The home has an all-new water filtration system. brLiving:brThe bright, contemporary living space has polished, rich wood flooring, which imbues a warm island vibe. The driftwood gray interior pops with accents of white and cream. Relax on the plush sofa or armchairs to socialize, read, or stream your favorite shows on the wall-mounted SmartTV with Roku. Stylish coffee tables, lamps, a ceiling fan, and large windows enhance the space. This living space has French doors, which open to a private deck with alfresco dining. brJust off the primary bedroom is a sunroom/breakfast nook with extra living space. This bonus room offers multi-purpose space (TV lounge/office/kid or teen space) and has a private entrance from the courtyard. This cozy room has an authentic island vibe with colorful mosaic floors, a wall of windows, a ceiling fan, and an air conditioner. Relax on the key-lime colored loveseat to stream movies on the Smart TV. The dinette can seat two or more.brKitchen/Dining:brThe open-concept kitchen/living space makes for easy entertaining and socializing. The sleek, fully-stocked modern kitchen has cream-colored, custom hardwood cabinets, granite countertops, and stainless appliances, including a glass-top electric stove, oven, microwave, dishwasher, full-size fridge, and farmhouse-style island sink. Prepare a tropical feast after a day at the beach! brOpen the French doors for a seamless indoor/outdoor entertaining space. The deck dining table has an adjustable umbrella. There are poolside picnic tables in the common area and a dinette in the breakfast nook.brBedrooms/Baths:brTropical Cottage has two bedrooms and two bathrooms. The living room has a twin-size sleeper sofa. Both air-conditioned bedrooms have tile floors and ceiling fans. Both sparkling-clean, beautifully remodeled bathrooms have water-saving toilets, toiletries, and hair dryers.brThe primary bedroom has a King bed, matching nightstands with lamps, a bureau, a closet, and an ensuite bathroom. This primary bathroom has a walk-in, glass door shower with a rain showerhead and hand-held shower wand. There’s an oversized, single-sink white granite vanity. brThe guest bedroom has two twin beds, a nightstand with lamp, a bureau and access to a hallway bathroom with a glass door shower and an oversized, single-sink white granite vanity.brTwo refreshing outdoor showers offer rustic tropical serenity, perfect for rising off the sand or chlorine after a day of island fun. brOutdoor Amenities:brA tall exterior fence, lush gardens, mature trees, and gardens provide privacy, security, and a peaceful, tropical ambiance. Enjoy a private dining space on your fenced back deck. This shaded dining space seats six.brA garden courtyard and whitewashed fence buffer your private hideaway from a central common area. Cool off in the sparkling blue swimming pool, or doze poolside on a cushioned lounge chair. The poolside deck features a gas grill and two wrought-iron picnic tables with seating for eight or more. Gather for an afternoon cookout in paradise! Mature palms, mango trees, and vibrant bougainvillea shade the pool deck.brSince laundry never sleeps (even when you're on vacation), the common area offers a laundry shed with two commercial washers and two commercial dryers. brDiscover the ultimate amenity: stroll just two blocks to Higgs Beach. Dip your toes in the emerald ocean. Collect seashells and savor serene Caribbean sunsets in pink, violet, and gold hues. Park your car in shaded street parking spots out front. Stroll or bike to attractions.brbrThe Neighborhood:brbrThe proximity of Tropical Cottage to the Casa Marina Hotel and the beautiful beaches adds to the appeal, making it a perfect blend of history, culture, and coastal living. Picturesque south island streets are lined with beautifully preserved Conch-style homes, each exuding character and charm. Lush, tropical landscaping adds to the serene atmosphere, making every walk or bike ride a delightful experience. brbrA car is not necessary on the island. Make the green choice. Park out front or along shaded side streets and enjoy the island on foot, by bicycle, scooter, trolley, or bus. The island trolley stop is one block away. The Duval Loop City bus stop is four blocks away. brStroll .07 miles to The Ernest Hemingway Home and Museum, which offers a fascinating glimpse into the life of one of America's greatest writers. Enjoy the diverse culinary scene with various restaurants, cafes, and bars offering everything from fresh seafood to classic Cuban cuisine. Local favorites such as Blue Heaven, Louie’s Backyard, and Sloppy Joe’s are within easy reach, providing unforgettable dining experiences. brDon't miss the chance to explore West Martello Tower during your stay! Just a 10-minute walk or a quick 3-minute bike ride from Tropical Cottage, this hidden gem is a tropical garden paradise on the site of a historic Civil War fort. The gardens, maintained by the Key West Garden Club, are open to the public. brHiggs Beach, approximately 0.5 miles (a 10-minute walk or a 3-minute bike ride), is the closest beach. Enjoy crystal-clear waters, perfect for swimming or snorkeling. The nearby White Street Pier offers panoramic sea views and excellent fishing opportunities. brApproximately 1.5 miles away, Smathers Beach is Key West’s largest public beach. This two-mile stretch of sugary sand is ideal for sunbathing, beach volleyball, and water sports such as kayaking, paddleboarding, and windsurfing. brFort Zachary Taylor Historic State Park Beach, approximately 2 miles away, offers natural beauty and historical intrigue. Visitors and locals gather here and at Mallory Square to celebrate each and every exquisite island sunset. brSeeking family-friendly activities or rainy-day excursions Check out the Key West Aquarium, the Butterfly and Nature Conservatory, The Shipwreck Treasure Museum, and the Lighthouse and Keepers Quarters Museum. Nightlife and live music abound in Key West! Take in a show at the Tropic Cinema. Catch a live band at the Green Parrot.

Cottage

TROPICAL COTTAGE by RENT KEY WEST VACATIONS - Quiet & gated. Pool/Deck/Pet frien

Key West, Florida, United States

Bed

Bath

Sleeps

$451.6

Tropical Hideaway comprises the ground level of a quintessential conch home, set back from the street and shaded by gardens and mature trees in a quiet, gated complex of six historic vacation rentals. The sunlight-yellow exterior blends Caribbean and Victorian influences: crisp white trim, decorative railings, restored original woodwork, and Bahamian shutters. brbrPrepare a home-cooked meal in the modern kitchen. Dine alfresco on the screened-in back porch. brbrThe shared central common area has a pool, picnic tables, gas grill and laundry area.brbrStroll to fine dining, beaches, and iconic attractions like the KW Butterfly and Nature Museum, Southernmost Point, Higgs Beach, and West Martello Tower. Street parking is available nearby. Tropical Hideaway is ideal for families, couples, and snowbirds. brbrLiving:brThe bright living space has original heart pine wood paneling. Relax, socialize, read, or stream your favorite shows on the wall-mounted SmartTV with Roku. The living space has French doors that open to a garden courtyard with easy access to the pool area.brbrKitchen/Dining:brJust off the living room is a galley kitchen with sleek black granite counters, tile floors, glass-top stove, oven, microwave, dishwasher, full-size fridge, and farmhouse sink. brbrThe kitchen’s back door opens to a screened-in porch with an original brick floor. Two dining tables seat six or more. This covered porch with a ceiling fan is a sublime spot to sip morning cappuccino or fresh-squeezed citrus juice. brbrBedrooms/Baths:brTropical Hideaway has two queen bedrooms and one bathroom. Both bedrooms have nightstands, ceiling fans, air conditioners, and Smart TVs. The front bedroom has a bureau and closet with a safe. The back bedroom has a door that opens out to the screened-in porch. The bedrooms share a jack-and-jill bathroom with a glass door, walk-in shower, and single-sink white granite vanity. The bathroom has a rain shower head, towels, toiletries, and hair dryers. brbrOutdoor Amenities:brA tall exterior fence, lush gardens, and mature trees provide privacy, and a peaceful, tropical ambiance. Enjoy a private dining space on your screened-in back porch.brbrThe front garden of Tropical Hideaway features a vibrant, original metal sculpture by John Martini, an internationally renowned artist who resides in Key West. Martini’s sculptures are shown in galleries and museums in New Mexico, Paris, and Italy, as well as in Lucky Street Gallery in Key West. Bold, electric colors characterize Martini’s work, which he creates by cutting metal with torches. These torches leave burn marks that are a hallmark of his sculptures.brbrA garden courtyard and whitewashed fence buffer your private hideaway from a central common area. Cool off in the sparkling blue swimming pool, or doze poolside on a cushioned lounge chair. The poolside deck features a gas grill and two wrought-iron picnic tables with seating for eight or more. Gather for an afternoon cookout in paradise! Mature palms, mango trees, and vibrant bougainvillea shade the pool deck.brbrThe Neighborhood:brTropical Hideaway’s proximity to the Casa Marina Hotel and the beautiful beaches adds to the appeal, making it a perfect blend of history, culture, and coastal living. Picturesque south island streets are lined with beautifully preserved Conch-style homes, each exuding character and charm. Lush, tropical landscaping adds to the serene atmosphere, making every walk or bike ride a delightful experience. brbrA car is not necessary on the island. Make the green choice. Explore the island on foot, by bicycle, scooter, trolley, or bus. The island trolley stop is one block away. The Duval Loop City bus stop is four blocks away. brbrStroll .07 miles to The Ernest Hemingway Home and Museum, which offers a fascinating glimpse into the life of one of America's greatest writers. Enjoy the diverse culinary scene with various restaurants, cafes, and bars offering everything from fresh seafood to classic Cuban cuisine. brbrHiggs Beach is the closest beach to Tropical Hideaway. Enjoy crystal-clear waters, perfect for swimming or snorkeling. The nearby White Street Pier offers panoramic sea views and excellent fishing opportunities. Fort Zachary Taylor Historic State Park Beach, approximately 2 miles away, offers natural beauty and historical intrigue. Visitors and locals gather here and at Mallory Square to celebrate each and every exquisite island sunset. brSeeking family-friendly activities or rainy-day excursions Check out the Key West Aquarium, the Butterfly and Nature Conservatory, The Shipwreck Treasure Museum, and the Lighthouse and Keepers Quarters Museum. Nightlife and live music abound in Key West! Take in a show at the Tropic Cinema. Catch a live band at the Green Parrot.

Tropical Village: Tropical Hideaway - Quiet & gated. Pool/Patio

Key West, Florida, United States

Bed

Bath

Sleeps

$713.28

Toon Hall is a quintessential 1930s-era Conch home, lovingly renovated with contemporary island sophistication. A parquet brick walkway leads from the garden gate to the columned front entry of this iconic tropical retreat. The sage-green exterior blends Caribbean, Victorian, and contemporary influences: crisp white trim, detailed woodworking, and abundant windows. brThis charming cottage is set back from the street and shaded by gardens, mature palms, and gumbo limbo trees in a quiet, upscale, gated complex of five historic Old Key West vacation rentals. The spacious pea-gravel courtyard boasts tropical landscaping, coral and rock hardscaping, and stone walkways leading to the shared pool area. The central common area, with a pool, picnic tables, and gas grill, is shared by guests of this upscale 5-plex. There’s also a shared laundry area with commercial washers & dryers.brToon Hall was aptly named by owner Jeff MacNelly (1947-2000), lauded as one of the most brilliant political cartoonists. In 1977, MacNelly launched his comic strip Shoe, characterized by wit, wry humor, and cynicism. He became The Chicago Tribune’s syndicated editorial cartoonist. Newsweek Magazine described MacNelly’s style as “goofy gracefulness.” In his lifetime, MacNelly received three Pulitzers and two Reuben Awards, the highest honor of the National Cartoonists Society. Since Jeff MacNelly’s death in 2000, the Shoe comic strip has been kept alive by Chris Cassatt, Gary Brookins, and Susie MacNelly. brJeff MacNelly and his wife Susie cherished the vibrant Key West arts scene as a wintertime retreat. Today, Toon Hall offers a laid-back retreat where guests can embrace their goofy side, laugh amidst the company of friends and loved ones, and remember not to take life too seriously.brSip Cafe Cubano on the private back deck as Caribbean breezes rustle the palm fronds, or relax poolside with a Margarita. Prepare a home-cooked meal in the modern kitchen. Dine alfresco when nights are fragrant with jasmine and frangipani. Stroll to great seafood, fine dining, beaches, and iconic attractions like the KW Butterfly & Nature Museum, Southernmost Point, Higgs Beach, and West Martello Tower. brAfter a day at the beach, shower off in the private, hot-water outdoor shower. Street parking is available out front. Toon Hall is ideal for families, groups of friends, couples, and snowbirds. The home has an all-new water filtration system. brInterested to learn more about the life and work of Jeff MacNelly Pop into The Gallery on the Greene, the exclusive KW gallery representing MacNelly. Cartoons, pen and ink drawings, and original canvases are on display. brbrLiving:brBright, airy living spaces have tile floors, large windows, ceiling fans, and an interior color palette of earthy, neutral, and crisp white. Plush suede sofas, nicely arranged around distressed coffee tables, provide a relaxing space for conversation, socializing, or family gatherings. A built-in bookshelf boasts a Smart TV with Roku. Stream your favorite shows or movies. French doors open to a front deck with built-in benches. Enjoy easy-breezy indoor/outdoor living space. brA den offers a rattan-style computer desk and vintage rolling desk chair.brKitchen/Dining:brThe sunny kitchen has tile floors, large windows, hardwood cabinets, and granite countertops. Appliances include a glass-top electric stove, oven, microwave, dishwasher, full-size fridge, and farmhouse-style sink. Prepare a tropical feast after a day at the beach! A door from the kitchen leads directly to a side deck with alfresco dining, making for seamless indoor/outdoor entertaining.brThe indoor dining room has tile floors, a ceiling fan, grand windows, and a solid yet rustic farmhouse-style dining table with seating for eight. brbrBedrooms/Baths:brToon Hall has three bedrooms and two bathrooms. There are two King beds, one Queen bed, and two double sofa beds. All three air-conditioned bedrooms have Smart TVs, tile floors, ceiling fans, closets, and rattan-style furniture (headboards, nightstands, bureaus & TV stands). brBoth sparkling-clean, remodeled bathrooms have granite vanities, water-saving toilets, toiletries, and hair dryers. An outdoor shower offers rustic, tropical serenity, perfect for rinsing sand or chlorine after a day of island fun. brBedroom Overview:brPrimary: King Bed, Ensuite bath w/ walk-in shower brBedroom #2: King Bed, access to hallway bath w/ tub/shower combobrBedroom #3: Queen bed, access to hallway bath w/ tub/shower combobrLiving Room: Two Twin Sofa Beds, access to private outdoor showerbrbrOutdoor Amenities:brA tall exterior fence, lush gardens, and mature trees provide privacy, security, shade, and a peaceful, tropical ambiance. Enjoy a private dining space on your fenced side deck. This dining space seats six. The front deck, with built-in benches, is an idyllic spot for entertaining and socializing. A garden courtyard and whitewashed fencing buffer your private space from the central common area. brCool off in the sparkling blue swimming pool, or doze poolside on a cushioned lounge chair. This swimming pool will delight families, children, the very young, and the young at heart. (The common pool area is shared by guests of this upscale 5-plex.) The poolside deck features a gas grill and two wrought-iron picnic tables with seating for eight or more. Gather for an afternoon cookout in paradise! Mature palms, mango trees, and vibrant bougainvillea shade the pool deck.brSince laundry never sleeps (even when you're on vacation), the common area offers a laundry shed with two commercial washers and two commercial dryers. brDiscover the ultimate amenity: stroll just two blocks to Higgs Beach. Dip your toes in the emerald ocean. Collect seashells and savor serene Caribbean sunsets in pink, violet, and gold hues. Park your car in shaded street parking spots out front. Stroll or bike to attractions.brbrbrThe Neighborhood:brbrThe proximity of Toon Hall to the Casa Marina Hotel and the beautiful beaches adds to the appeal, making it a perfect blend of history, culture, and coastal living. Picturesque south island streets are lined with beautifully preserved Conch-style homes, each exuding character and charm. Lush, tropical landscaping adds to the serene atmosphere, making every walk or bike ride a delightful experience. brbrA car is not necessary on the island. Make the green choice. Park out front or along shaded side streets and enjoy the island on foot, by bicycle, scooter, trolley, or bus. The island trolley stop is one block away. The Duval Loop City bus stop is four blocks away. brStroll .07 miles to The Ernest Hemingway Home and Museum, which offers a fascinating glimpse into the life of one of America's greatest writers. Enjoy the diverse culinary scene with various restaurants, cafes, and bars offering everything from fresh seafood to classic Cuban cuisine. Local favorites such as Blue Heaven, Louie’s Backyard, and Sloppy Joe’s are within easy reach, providing unforgettable dining experiences. brDon't miss the chance to explore West Martello Tower during your stay! Just a 10-minute walk or a quick 3-minute bike ride from Toon Hall, this hidden gem is a tropical garden paradise on the site of a historic Civil War fort. The gardens, maintained by the Key West Garden Club, are open to the public. brHiggs Beach, approximately 0.5 miles (a 10-minute walk or a 3-minute bike ride), is the closest beach to Southern Cross. Enjoy crystal-clear waters, perfect for swimming or snorkeling. The nearby White Street Pier offers panoramic sea views and excellent fishing opportunities. brApproximately 1.5 miles away, Smathers Beach is Key West’s largest public beach. This two-mile stretch of sugary sand is ideal for sunbathing, beach volleyball, and water sports such as kayaking, paddleboarding, and windsurfing. brFort Zachary Taylor Historic State Park Beach, approximately 2 miles away, offers natural beauty and historical intrigue. Visitors and locals gather here and at Mallory Square to celebrate each and every exquisite island sunset. brSeeking family-friendly activities or rainy-day excursions Check out the Key West Aquarium, the Butterfly and Nature Conservatory, The Shipwreck Treasure Museum, and the Lighthouse and Keepers Quarters Museum. Nightlife and live music abound in Key West! Take in a show at the Tropic Cinema. Catch a live band at the Green Parrot.

Tropical Village: Toon Hall - Quiet & gated. Spacious! Pool/Decks/Pet friendly

Key West, Florida, United States

Bed

Bath

10

Sleeps

$1800.0

Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resort's observation deck guarantees a stunning view from sunrise to sunset, and even to gaze at the stars.brbrRent a boat for a private viewing of the Keys or take a jetski for a spin right from the resort's marina. Work up a sweat at the on-site exercise room and afterwards, relax your body and mind in the sauna. brbrThe Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios house two people and are equipped with a small refrigerator, coffee maker and microwave oven. One-bedroom suites sleep up to four while most two-bedroom suites sleep up to six, while both include a full kitchen, dining area and decked out living area. Each is lovingly furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West.brbrThe Galleon Resort is perfectly positioned, sitting only two blocks from Duval Street - a legendary road that boasts top-notch restaurants, dazzling nightlife and non-stop soirees. Party until dawn at a carnival, swing by a cuban cigar stand or bring your camera to the exotic butterfly conservatory, all located on this versatile street that's earned its reputation. At the northwest end of Duval Street lies Mallory Square, a plaza which is famous for its Sunset Celebration - tourists gaze at the sunset while arts and crafts displays and entertainers amuse the gatherers. Key West's oldest attraction, the Key West Aquarium is a hit with families - everyone will enjoy scoping out the menagerie of rainbow-hued fish.brbrA few things to note.... The resorts require a credit card at check-in to cover incidentals. Please note parking fees may apply and are not included in the price quoted here. The room view and bed may vary and is not guaranteed here unless agreed upon before booking. If you would like an upgrade to a specific view or bed please let me know and if available I can do that, additional fees may be required. Additionally some resorts have various towers/buildings and may vary, please check with us in advance to discuss the view/building/unit and. Finally, Tourist Accommodation Taxes must be paid directly to the resort; this is standard procedure for resorts. brbrbrbrResort policies and rules

Hotel Resort

2 Galleon Resort, Hot Tub, Pool, Marina, Gym!

Key West, Florida, United States

Bed

Bath

Sleeps

$352.98

Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap around porch, a pool deck and a heated dipping pool/large hot tub. The house and yard are quite spacious by Key West standards. The decor, while maintaining the character of a grand old Florida Keys home, features first rate appointments such as: quartz counter tops, new plumbing fixtures, modern kitchen appliances, flat screen TVs in the living room and in all 4 bedrooms, wireless Internet, air conditioning, heat, washer, dryer, comfortable furniture and lush landscaping.The location is ideal. Situated in the peaceful Meadows neighborhood on the edge of Old Town, the house is close enough to Duval Street to access the party, but far enough to ensure quiet rest.brbrbrPicture yourself sipping a drink with your friends in the shade or sunshine on the spacious porch and pool deck, enjoying the heated dipping pool/hot tub or relaxing on the porch swing all evening after dinner. And outdoor entertaining is made easier with a half bath that opens directly onto the deck!brbrThe house has the rare ability to sleep quite a few people. Perfect for a family or a group of couples, the house has four (4) bedrooms, one on the first floor and three on the second floor. And special considerations have been taken to help assure you can get the recuperating rest you'll need, such as new windows, solid core doors and full insulation.brbrThe First Floor Master Suite features a king sized bed, two spacious closets, a flat screen TV, a private restroom with a shower. This suite also has a door leading directly to the pool deck.brbrThe Second Floor Master Suite features a king sized bed, two closets, a flat screen TV and private restroom with a shower.brbrBedroom 3 features a king sized bed, two closets, a small desk nook, a flat screen TV and shares a restroom with a shower/bath with Bedroom 4.brbrBedroom 4, the smallest bedroom, features a full sized bed, a closet, a flat screen TV and shares a restroom with a shower/bath with Bedroom 3.brbrAll linens and towels are provided for the bedrooms and restrooms.brbrOlivia Place is available to rent on a monthly basis only. Availability is very limited, so we suggest you inquire about your dates and book well in advance of your stay.br brbrbrKeywords: house

Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews

Key West, Florida, United States

Bed

Bath

Sleeps

$730.13

You and your guests will have exclusive use of this 40ft yacht all to yourselves. The yacht stays docked, the entire reservation, at the Perry Hotel, which invites you to complimentary use of two stunning waterfront swimming pools, live music, three restaurants, complimentary shuttle service, & more. You and your guests can come and go on the yacht anytime, day or night.brbrDue to local regulations, it is required that you choose at least one of the following options during your reservation: a two-hour excursion, a four-hour excursion, an eight-hour excursion, a ten-hour excursion, or a 24-hour excursion.brbr- 2-hour excursion: $900+tax & gratuitybr- 4-hour excursion: $1450+tax & gratuitybr- 8-hour excursion: $1950+tax & gratuitybr- 10-hour excursion: $2200+tax & gratuitybr- 24-hour excursion: $2500+tax & gratuity brbrThe prices listed above are per excursion and not per person. The cost of the excursions must be paid directly to our company at the time of booking. The prices listed above include the captain's fee and fuel.brbrThese excursions are highly recommended by our previous guests and are sure to provide you with a memorable experience. During these outings, you'll have the opportunity to learn how to navigate the yacht, snorkel around the coral reef, fish from the yacht, spot dolphins and sea turtles, and much more. Our 24-hour charter is particularly popular as it combines the activities of a day excursion with the unique experience of spending a night anchored on the ocean with a limit of 6 total guests. If you are staying for more than two nights, you can even enjoy multiple excursions during your reservation period.brbrJust imagine sleeping under the stars with no neighbors next to, above, or below you like in a hotel room. You can spend your days and nights fishing from the boat, relax on the deck while listening to the sounds of tropical fish jumping in the water, and experience the thrill of being away from the marina, anchored on the ocean. If you're seeking an adventurous and extraordinary vacation surrounded by breathtaking ocean views, wildlife, and fish, this is the perfect choice for you. You might never want to return to land again!brbrThe weather in this area is ideal throughout the year for activities such as snorkeling, fishing, lobster catching (seasonal), kayaking, paddleboarding, learning to sail, scuba diving, or simply enjoying a relaxing sunset cruise.brbrIn addition to our excursions, we provide an exceptional concierge service that brings luxury directly to you. For an additional cost, our offerings include VIP packages, chef services, catering, provisioning, limo service, golf cart rentals, sporting goods rentals, and much more.brbrThe Perry Hotel is a pristine resort located in the heart of a turquoise paradise with crystal-clear waters. Your stay at the hotel includes access to two waterfront swimming pools, live music performances, a fitness room, three restaurants, retail shops, marina showers, laundry facilities, and more. The Perry Hotel also offers complimentary shuttle service to and from downtown Key West, which is conveniently located nearby. Additionally, the resort is in close proximity to retail shops, grocery stores, restaurants, and various attractions.brbrThis yacht is one of a kind with its three stateroom layout. The entire starboard side is a master suite with a private shower and a small desk area. The two other staterooms are separated by a bathroom with shower. One has a double bed, the other a queen. The kitchen area has a settee that converts to a queen bed that can sleep two.brbrIf you're interested in a bareboat charter to the Dry Tortugas, please note that a minimum of five nights is required. In addition to the payment made through VRBO, you would need to purchase three 24-hour excursions, allowing you to spend one night at the Dry Tortugas. On your way to and from the destination, you would also stay at the Marquesas Islands, which are located halfway. This charter is truly a once-in-a-lifetime experience that will provide memories to cherish forever. Due to the distance, it is not possible to make the trip to the Dry Tortugas and back in just one day. brbrWe also offer charters to popular destinations such as Little Palm Island, Bahia Honda State Park, Marathon, Islamorada, Key Largo, and more.brbrThe excursions/charters offered are discounted from the regular price and must be paid directly to our company outside of VRBO at the time of booking.brbrWe also offer bareboat day charters where you do not have to stay overnight on the boat. This type of charter must be booked directly through our company as VRBO is only set up for overnight accommodation bookings.brbrOur company also offers snorkel gear, wet suits, fishing gear, e-bikes, scooters, golf carts, kayaks, and paddle board rentals, for an additional cost, to truly take in Key West. brbrIf you want to operate the boat or tender yourself you must book directly with our company to go through an approval process. Taking the vessel yourself (and not hiring a captain) is subject to prior experience on similar vessels. brbrThe advertised price on this listing covers the cost of insurance that covers you and the crew during your reservation period as well as the cost to survey the boat after you leave. You will be required to undergo a bareboat contract and will take full responsibility of the operation and safety of the yacht, crew, and all passengers.brbrGuests must be able to walk up & down stairs inside the boat and be able to make a longer than usual step at times to get on and off the boat.brbrPlease contact us if this yacht does not meet your specifications as we have other yachts that may.brbrAdditional House Rules:brbr1. There is a $50 charge per night per person over four. There is a $100 fee to make any changes to your charter after your paperwork has been drafted and emailed to you up to 3 days prior to check in. There is a $200 fee to make any changes to your charter after your paperwork has been drafted and emailed to you 3 days or less prior to check in.brbr2. There is a $150 fee to add additional guests on an excursion, not staying overnight after your paperwork has been processed, up to 3 days prior to check in, and $200 per guest not staying overnight, 3 days or less prior to check in on a day charter. brbr3. As posted in this listing, you must pay our company directly for at least one excursion at the time of booking. In the event you refuse to book an excursion, your reservation will be canceled with no refund. There is no refund for a paid excursion in the event the excursion is canceled and there is available time left in your reservation to reschedule it to.brbr4. There are no refunds for a change in number of guests. There is $100 extra guest fee per person that is joining you on a day charter that is not staying overnight.

House Boat

NEW VRBO Listing! Elegant 40' Yacht in 5-Star Resort

Key West, Florida, United States

Bed

Bath

8

Sleeps

$316.61

Waterfront Comfort Minutes from Key WestbrbrWelcome to Seaside Cottage, a beautifully maintained 2-bedroom, 2-bath canal-front retreat offering the perfect blend of comfort, space, and classic Florida Keys living. Set along a crystal-clear boating canal with fast access to open water, this property is ideal for guests seeking relaxation, convenience, and plenty of room to spread out.brbrStep inside to an inviting open layout featuring a spacious, updated kitchen with wood cabinetry, ...stainless steel appliances, granite countertops, and a generous island designed for effortless entertaining. The sunlit living area flows onto a private porch overlooking the wateran ideal spot for morning coffee, evening cocktails, or simply watching the boats go by.brbrBoaters will appreciate the 80' concrete seawall, providing excellent docking space and easy navigation. A fully furnished, this home offers peace of mind and modern comfort.brbrThe home provides ample parking for your boat trailer, kayaks, and other toys, Three vehicles/trailer parking on site. brbrThis home has lush landscaping adds to the home's tropical appeal with a grassy rear yard. After a day on the water, return to your private slip, rinse off your gear, and unwind in your own Lower Keys sanctuary. Twin Hammocks are provided to watch the stars at night. brbrWhether you're seeking a serene waterfront getaway or a home base close to Key West's attractions, Seaside Cottage delivers the best of island living and quick access to down town key west.brbrThis home has bedding for 4 if you are bringing 6 people please bring your aero bed.brbrBook now and enjoy your slice of paradise!brbrThis home is a 28 night minimum.brbrYou must be 25 or older to rent. (25 year old must be present during entire stay)brbrThis is a 28 day minimum rental.brbrThis property is dog friendly, so you are required to select the pet fee option when booking if you are bringing a dog. All dogs must be approved prior to booking. There are breed restrictions due to insurance reasons. Dogs 20lbs or less allowed - must be pre-approved. Pet fee is non-refundable & taxable. If you are booking onAirbnb~ the pet fee will be asked for after booking, as it will not be included in the total cost. The fee is based on the breed & size. Dog friendly only - NO cats or other animals. Max allowed is 2. Failure to disclose the dog and pay the pet fee will result in a charge of up to $500 and will be asked to vacate without a refund. brbrCheck-in is 4 pm on day of arrivalbrbrCheck out is 10 am on the day of departurebrbrVacation Rentals of the Florida Keys provides a complimentary starter kit of soap, toilet paper, paper towels, dishwasher detergent, and laundry detergent. Guests will need to provide ongoing supplies for your stay.brbrVacation Rentals of the Florida Keys (Vrotfk) has Terms and Conditions of use for this property and all the properties we manage. As a party to this transaction, you and your party understand that by renting this property, you expressly agree to the Terms and Conditions of Vacation Rentals of the Florida Keys (Vrotfk). Once a deposit is received by Vrotfk, or through any other platform you choose to book the property, that act will acknowledge and accept these Terms and Conditions. Terms and Conditions are attached to every reservation confirmation. Terms and Conditions will be sent via an e-signature document that is required to be signed after booking.brbrAmenities Include:brbr- Air Conditioning: Yesbrbr- Kitchen: Yesbrbr- Private Entrance: Yesbrbr- Smoke Detector: Yesbrbr- Bed Size 1st/Master: Quenbrbr- Bed Size 2nd Rm: Queenbrbr- Child Friendly: Yesbrbr- Coffee Maker: Yesbrbr- Dockage: Yes 80 ftbrbr- Pet Friendly: Yesbrbr- BBQ Grill: Yesbrbr- Ceiling Fans: Yesbrbr- Internet Access: Yesbrbr- Micro/Dishwash/Disp.: Yesbrbr- Refrig And Ice Maker: Yesbrbr- Square Footage, Est.: 1160brbr- Stove/Oven Elec/Gas: Yesbrbr- TV Cable/Satellite: Streamingbrbr- TVs/VCR/DVD: Yesbrbr- View: Canalbrbr- washer dryer: Yesbrbr

Seaside Cottage minutes to Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$526.43

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrMODERN MAJESTY is a stunning, freshly renovated three-bedroom condo that checks every box for the perfect vacation rental. This large unit is laid out over one floor, meaning you don’t have to worry about stairs. The three bedrooms are luxuriously appointed suites, each with their own en-suite bathroom. The kitchen is as functional as it is beautiful. Once you step outside onto your spacious private patio, with the breathtaking ocean and sunset views, you’ll behold the true majesty of Key West. Coupled with Last Key Realty’s unrivaled Guest Services, your month at MODERN MAJESTY will be the stay of a lifetime. brbrTHE LOCATION...brbrLocated in the private gated community of Truman Annex, you’ll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town Key West. While close to all the action, you'll benefit from the peace and tranquility Truman Annex is known for. While you can walk to most places, if you bring a car to this excellent location, there is a reserved off-street parking space located in the garage.brbrTHE LIVING AREA…brbrThe owners spared no expense when it came to the renovations and the outfitting of the property, which is apparent from the moment you walk in. From the high ceilings to the meticulously chosen decor, every turn showcases another touch of class. brbrWhen you enter, you’ll quickly find yourself in the kitchen, where you can’t miss the beautiful natural bar with seating for 4. The kitchen itself is outfitted with every appliance and accessory you might need for those nights you wish to cook at home. From the kitchen, you’ll move into the living room, which features high-end furniture and comfortable seating that you’ll melt into.brbrGo from the living room to the grand private patio outside. If we put a basketball hoop at each end you’d have a full court! This incredible outdoor space has seating for all and includes a propane grill to cook up the day’s fresh catch. We have a feeling you’ll spend most nights relaxing on the patio as the sun sets in the distance.brbrTHE POOL & FORT ZACHARY TAYLOR STATE PARK…brbrThe Community Pool is right downstairs, located directly on the waterfront. There are plenty of chaises for your comfort and a cabana with restrooms for your convenience. Best of all, you’ll have “orchestra seats” to watch the sunset on the Gulf of Mexico. Fort Zachary Taylor State Park is a half mile away, with the prettiest beach in Key West.brbrTHE ACCOMMODATIONS…brbr** Master Suite - a King bed, a flat-screen TV, a large walk-in closet, and an en-suite bathroom with double sinks and a spacious walk-in shower, and a shared balcony with Suite Twobrbr** Suite Two - a King bed, a flat-screen TV, and an en-suite bathroom with double sinks and a spacious walk-in shower, and shared balcony with the Master Suitebrbr** Suite Three - a King bed, a flat-screen TV, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbrbr** Washer and Dryerbrbr** Central Heat and A/Cbrbr** Ceiling Fansbrbr** Flat Screen TVs in Living Room & All Bedroomsbrbr** Fully Equipped Kitchenbrbr** Basic stock of spicesbrbr** Starter supply of paper productsbrbr** Starter set of cleaning productsbrbr** Linens and Towels providedbrbr** Wireless high-speed Internet access & full cable includedbrbrbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbrbr** Large Heated Community Poolbrbr** One Garaged Off-street Parking SpacebrbrbrbrOther notes:brbrbr** Interim housekeeping provided upon requestbrbr** This property will accommodate up to 6 adultsbrbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

Condo

**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR/3.5BA Condo & Pool + LAST KEY SERVI

Key West, Florida, United States

Bed

Bath

Sleeps

$258.55

IMAGINE PARADISE…brPicture your very own tropical estate enhanced with luxurious perks to include an expansive outdoor oasis with a large pool and tiki hut! This adorable private residence is centrally located area of “Mid Town” offering tranquil surroundings just a short distance to everything! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brA vibrant first impression greets you to this island hideaway with front porch seating to soak up the serene surroundings. Step inside to find an open space showcasing tile flooring throughout and coastal decor. A cozy seating area with a tv begins your journey with a fully equipped and renovated kitchen steps away. Granite counters, gorgeous custom cabinetry, stainless steel appliances and bar seating for 3 occupy this cheery space. Adjacent to the kitchen is a light filled, air-conditioned sunroom equipped with comfortable furnishings, a pool table and TV. An office room is also available for those working remotely. Cable is offered in the living room. The guest rooms and outside TVs are smart TVs. brbrSLEEPING ARRANGEMENTS…brEnjoy a peaceful evening’s rest in either queen guest room – both equipped with a flat screen TV and ceiling fans to keep you cool. The shared hallway bathroom comes with a walk-in glass shower. An additional full bathroom with a walk-in glass shower is located right off the sunroom. brbrOUTDOOR LIVING…brThis dream home come true is surrounded by mature landscaping, a large heated private pool and a charming tiki hut with plenty of bar and dining seating for the whole crew for incredible entertaining. Rinse off the the outdoor shower, catch an island breeze in one of the loungers and enjoy a movie on the flat screen TV.brbrPARKING...brPlenty of street parking is available here on the 2300 Block of Staples Ave.brbrPETS...brThis home is NOT pet friendly. 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).brbrLET THE STRESS MELT AWAY…

BAREFOOT BUNGALOW~2 Bedroom, 2 Bathroom Home w/ Office, Pool and Tiki Hut!

Key West, Florida, United States

Bed

Bath

4

Sleeps

$1329.77

Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and beautiful contemporary design creates an environment of relaxation and restoration. Guests are encouraged to slow down and relax, to dip into the outdoor pool and whirlpool hot tub while soaking up some famed Floridian rays. Guests will also receive privileges at the adjacent Hyatt Key West Resort & Marina, offering even more ways to keep occupied even on your off days. The right size, the perfect view and the must-have amenities... Hyatt Sunset Harbor Resort's residences become the perfect home-away-from-home during your stay in Key West! Classic studios offer a king-size bed, casual living area, TV and DVD player. The one- bedroom tropical-style residence features a deluxe queen bed, fully-equipped kitchen, dining area, ceiling fans, seating area with TV, stereo, DVD player and private balcony. The beautiful two-bedroom residence is even more luxe, and includes a master suite with king-sized bed, adjoining bath and spa tub, a guest suite with queen bed and full bathroom. In addition, enjoy a fully-equipped kitchen, seating area, TV, DVD player and balcony! Hyatt Sunset Harbor isnu2019t just another Key West property - itu2019s in the heart of Old Town, the heart and soul of one of Americau2019s most treasured vacation destinations. Nearby, you can also enjoy Duval Street shopping or nightlife and Mallory Square. Of course, if you're looking for more natural pursuits, you have plenty of options - Key West is a haven for fishers, and the unique ecosystem is well-suited to those seeking to explore by foot or bike. Plenty of unique attractions await those looking for a change of pace - check out the The Harry S. Truman Little White House, Key West Aquarium, Key West Lighthouse Museum and Mel Fisher Maritime Heritage Museum! On-Site Features & Amenities Concierge Internet access Outdoor pool Shared laundry facilities Whirlpool/hot tub Nearby Attractions Bar Boating Drug store Fitness center Golf Grocery store Hiking Live entertainment Ocean Park Restaurant River Shopping area Snack bar Spa services Tennis Water skiing Wind surfing Policies No Pets No SmokingbrbrPlease be advised that we cannot assume responsibility for any inconvenience, unavailability,bror interruption of services due to necessary repairs, ongoing improvements, on-sitebrconstruction, closure of amenities, or other circumstances beyond our control. Guests will bebrpromptly notified of any such issues as they come to our attention. Please note that room viewsbrand bed configurations may vary at some resorts while accommodating the same number ofbrguests. We encourage guests to seek clarification prior to booking and to inform us of anybrspecial requests, which we will endeavor to accommodate if feasible. Additionally, all resortsbrrequire a valid ID of the person on the reservation and a major credit card at check-in to coverbrpotential charges for damages, liabilities, and incidentals.

Hotel Resort

Sunset Harbor Resort, Marina, In Town, Hot Tub, Pool, Balcony

Key West, Florida, United States

Bed

Bath

Sleeps

$307.44

Welcome to OFF THE HOOK — Your Perfect Key West Getaway!brbrEscape to this stunning, meticulously updated 3-bedroom, 3-bathroom home located in desirable mid-town Key West. Just under a mile from the vibrant heart of Duval Street, local beaches, and Garrison Bight Marina, OFF THE HOOK offers the ideal blend of comfort, style, and convenience for your next vacation.brbrProperty Highlights:brbrBedrooms: 3 (King Primary Suite, Queen Family Suite, Guest Suite with 2 Twins/convertible King)brbrBathrooms: 3 full baths, including ensuite in primary bedroombrbrLocation: Mid-town Key West, less than 1 mile from downtown and beachesbrbrParking: Private gated parking plus ample street parking for boats/trailersbrbrInside the Home:brbrStep inside to a bright and airy living space filled with natural light and featuring wood-like tile flooring and recessed lighting throughout. Relax in the spacious living room with a 65” Smart TV and easy access via French doors to the private pool area.brbrThe kitchen is fully equipped and opens to a cozy bistro-style dining area—perfect for meals at home or entertaining guests.brbrGuest Suite: Located on the main floor, this room offers two twin beds that can be converted to a king bed upon request, perfect for flexible sleeping arrangements.brbrPrimary Suite: Upstairs, enjoy a peaceful retreat with a king bed, Smart TV, ample closet space, and a luxurious ensuite bathroom.brbrFamily Suite: Also upstairs, the large family suite includes a queen bed, full-size futon, large closet, Smart TV, and access to a shared full bathroom with tub/shower combo.brbrOutdoor Oasis:brbrYour backyard paradise awaits with a private swimming pool surrounded by loungers and a comfortable artificial turf area. Enjoy outdoor dining and entertaining in the dedicated patio space. For cooler months (Nov 15–May 1), pool heating is available for an additional daily fee.brbrAdditional Amenities & Details:brbrImpact-resistant windows and doors for added safety and comfortbrbrSecure property access with a 6-foot privacy/security fence around the compoundbrbrBeach chairs and towels provided for your conveniencebrbrClose proximity to local attractions: Duval Street nightlife, beaches, Garrison Bight Marina (1 block away)brbrBoat owners: Ample street parking available for trailersbrbrImportant Notes:brbrPool Heat: Optional Nov 15–May 1, $20/day, must be arranged before check-in.brbrPet Policy: Pre-approval required for dogs. Max 1 dog, up to 50 lbs. Pet fee $20/day, reduces total guest occupancy by 1. Fees due prior to arrival.brbrGet OFF THE HOOK from everyday life and experience the best of Key West in style and comfort. We look forward to hosting you!

OFF THE HOOK - 3 Bedroom / 3 Bathroom W/ Pool & Parking

Key West, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

Condo

Spacious Key West Condo at Coconut Mallory Resort & Marina

Key West, Florida, United States

Come and explore all that Key West has to offer! This unit at Coconut Mallory is a one level condo with both bedrooms and bathrooms, the full kitchen, dining room, and living room with a queen-size sleeper sofa and connecting balcony all on one level. There is an elevator in the building to reach our unit and there are laundry facilities outside of the units on the top floor at each end of the building.br Coconut Mallory's amenities include wireless internet, two pools, a hot tub, grills, a marina with its own clubhouse, a four minute ride to the beach, and close proximity to the many Key West activities and attractions.brbrDamage and incidentals: you will be responsible for any damage to the rental property caused by you or your party during your stay.

Bed

Bath

Sleeps

$213.85

This 3 bedroom home is located one block from where Tennessee Williams home was located. The home has a true historic flavor including the neighborhood. Lush garden with outside pool and Jacuzzi for enjoyment and relaxation. The backyard is fenced for privacy. Inside offers large living room with soaring ceilings, private bedrooms and full size kitchen with dining room overlooking the pool. brOne off street parking spot for your use. Located close to the beaches and downtown area. Great local restaurants- El Siboney on Catherine Street is in the area as well as a locally owned grocery store-Faustos. Live like a local conch and stay in the ambiance and charm on Duncan Street Property.brbrNote: The property is set up for no contact check-in. The unit has been cleaned and sanitized by a professional cleaning company prior to your arrival. If Key West closes to tourists due to COVID related travel shutdown, you will recieve 100% refund minus credit card fee of 3.5%.

Lush Gardens-Pool-Jacuzzi-No Contact Check-In

Key West, Florida, United States

Bed

Bath

6

Sleeps

$1594.08

The Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios house two people and are equipped with a small refrigerator, coffee maker and microwave oven. One-bedroom suites sleep up to four while most two-bedroom suites sleep up to six, while both include a full kitchen, dining area and decked out living area. Furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West. Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resort's observation deck guarantees a stunning view from sunrise to sunset, and even to gaze at the stars. Rent a boat for a private viewing of the Keys or take a jetski for a spin right from the resort's marina. Work up a sweat at the on-site exercise room and afterwards, relax your body and mind in the sauna. The Galleon Resort is perfectly positioned, sitting only two blocks from Duval Street - a legendary road that boasts top-notch restaurants, dazzling nightlife and non-stop soirees. Party until dawn at a carnival, swing by a cuban cigar stand or bring your camera to the exotic butterfly conservatory, all located on this versatile street that's earned its reputation. At the northwest end of Duval Street lies Mallory Square, a plaza which is famous for its Sunset Celebration - tourists gaze at the sunset while arts and crafts displays and entertainers amuse the gatherers. Key West's oldest attraction, the Key West Aquarium is a hit with families - everyone will enjoy scoping out the menagerie of rainbow-hued fish. -brbrPlease be advised that we cannot assume responsibility for any inconvenience, unavailability,bror interruption of services due to necessary repairs, ongoing improvements, on-sitebrconstruction, closure of amenities, or other circumstances beyond our control. Guests will bebrpromptly notified of any such issues as they come to our attention. Please note that room viewsbrand bed configurations may vary at some resorts while accommodating the same number ofbrguests. We encourage guests to seek clarification prior to booking and to inform us of anybrspecial requests, which we will endeavor to accommodate if feasible. Additionally, all resortsbrrequire a valid ID of the person on the reservation and a major credit card at check-in to coverbrpotential charges for damages, liabilities, and incidentals.

Hotel

Hotel Room Galleon Resort, Pool, Hot Tub, In Town!

Key West, Florida, United States

Bed

Bath

Sleeps

$933.77

Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and beautiful contemporary design creates an environment of relaxation and restoration. Guests are encouraged to slow down and relax, to dip into the outdoor pool and whirlpool hot tub while soaking up some famed Floridian rays. Guests will also receive privileges at the adjacent Hyatt Key West Resort & Marina, offering even more ways to keep occupied even on your off days. The right size, the perfect view and the must-have amenities... Hyatt Sunset Harbor Resort's residences become the perfect home-away-from-home during your stay in Key West! Classic studios offer a king-size bed, casual living area, TV and DVD player. The one- bedroom tropical-style residence features a deluxe queen bed, fully-equipped kitchen, dining area, ceiling fans, seating area with TV, stereo, DVD player and private balcony. The beautiful two-bedroom residence is even more luxe, and includes a master suite with king-sized bed, adjoining bath and spa tub, a guest suite with queen bed and full bathroom. In addition, enjoy a fully-equipped kitchen, seating area, TV, DVD player and balcony! Hyatt Sunset Harbor isnu2019t just another Key West property - itu2019s in the heart of Old Town, the heart and soul of one of Americau2019s most treasured vacation destinations. Nearby, you can also enjoy Duval Street shopping or nightlife and Mallory Square. Of course, if you're looking for more natural pursuits, you have plenty of options - Key West is a haven for fishers, and the unique ecosystem is well-suited to those seeking to explore by foot or bike. Plenty of unique attractions await those looking for a change of pace - check out the The Harry S. Truman Little White House, Key West Aquarium, Key West Lighthouse Museum and Mel Fisher Maritime Heritage Museum! On-Site Features & Amenities Concierge Internet access Outdoor pool Shared laundry facilities Whirlpool/hot tub Nearby Attractions Bar Boating Drug store Fitness center Golf Grocery store Hiking Live entertainment Ocean Park Restaurant River Shopping area Snack bar Spa services Tennis Water skiing Wind surfing Policies No Pets No Smoking Check-in time: 4:00 PM Check-out time: 10:00 AM -brbrPlease be advised that we cannot assume responsibility for any inconvenience, unavailability,bror interruption of services due to necessary repairs, ongoing improvements, on-sitebrconstruction, closure of amenities, or other circumstances beyond our control. Guests will bebrpromptly notified of any such issues as they come to our attention. Please note that room viewsbrand bed configurations may vary at some resorts while accommodating the same number ofbrguests. We encourage guests to seek clarification prior to booking and to inform us of anybrspecial requests, which we will endeavor to accommodate if feasible. Additionally, all resortsbrrequire a valid ID of the person on the reservation and a major credit card at check-in to coverbrpotential charges for damages, liabilities, and incidentals.

Hotel Resort

Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.

Key West, Florida, United States

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