33040, Florida, United States Vacation Rental Homes By Owner - Page 88

Chicken Water Cabana at Custom House InnbrbrLocated in the heart of vibrant Duval Street, Chicken Water Cabana at Custom House Inn offers the ultimate Key West experience with two beautifully designed, modern, adjacent suites, Underwater Cabana and Chicken Run. Just steps from the island's best bars, restaurants, and attractions, these colorful, freshly renovated suites are perfect for groups of up to 8 guests. Whether you're here for a relaxing getaway or an adventure-filled vacation, you'll love the convenience and charm of staying in this prime downtown location.brbrThe Ambiance:brEach suite is thoughtfully designed to maximize space and comfort. Whether you're working remotely or unwinding after a day of exploring, you'll feel right at home.brbrSuite 1 - Underwater Cabana: A lively blue-themed room featuring a King Bed and Queen Pullout Couch, perfect for a restful night after a day of fun in Key West.brSuite 2 - Chicken Run: A relaxing green-themed space with a King Bed and Queen Pullout Couch, offering the same comfort and style.brbrEach suite comes equipped with modern amenities, including a private mini-bar, TV, mini-fridge, and coffee maker. Plus, a large rooftop deck with sectional sofas and a turf floor offers a cozy outdoor space to relax with friends or family.brbrGuest Perks:brContactless Check-In: Enjoy a hassle-free arrival with a personalized access code for self-check-in. Please note that parking is not available on-site.brbrShared Amenities: brRelax on the rooftop deck, perfect for evening socializing or a morning coffee.brbrNeighborhood Highlights:brThe Custom House Inn is located on the 100 block of Duval Street, placing you in the heart of Key West's entertainment and culture. Enjoy the vibrant nightlife, local bars, and iconic landmarks, all within walking distance. Whether you're heading out to explore the famous bars or wandering through local shops, everything is just steps away.brbrTransportation Tips:brKey West is very walkable, and with everything so close, you'll find plenty to see on foot. However, you can easily rent bikes, scooters, or even hop on a pedi-cab to get around. For longer distances, rideshare services like Uber and Lyft are readily available. While there's no on-site parking, there are several nearby overnight parking lots for your convenience.brbrParking Information:brPlease note there is no on-site parking for these units. However, several pay-to-park options are available nearby:br- Fleming Street Pay-to-Park Lot (closest option)br- 204 Simonton Streetbr- Caroline Street Outdoor Parking Lotbr- Park N Ride Old Town GaragebrbrOther Things to Note:br- For larger groups, you can reserve additional suites at Custom House Inn to accommodate up to 20 guests.br- The exterior of the building is equipped with security cameras to ensure a safe and enjoyable stay for all guests.br- These are two adjacent suites located together on the first floor.br- No washer/dryer on-sitebr- No pets allowedbr- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrBook your stay at Chicken Water Cabana at Custom House Inn and enjoy the ultimate Key West vacation experience, right in the heart of Duval Street!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Chicken Water Cabana at Custom House Inn | Two Modern Suites!

Key West, Florida, United States

Bed

Bath

Sleeps

$2179.76

Custom House Inn | Colorful Suites & Rooftop Vibes on Duval Street!brbrExperience the ultimate group getaway at Custom House Inn, a modern, one-of-a-kind condo complex located directly on Key West's iconic Duval Street. Perfect for larger groups, this vibrant property features five uniquely designed suites for up to 25 guests. Whether you're planning a family vacation, reunion, or special celebration, Custom House Inn offers the perfect mix of comfort, style, and location for exploring everything Key West has to offer. You won't find anything this spacious and stunning on this end of Duval Street—this rare gem offers far more than expected. Truly one-of-a-kind!brbrThe Ambiance:brEach suite at Custom House Inn is thoughtfully designed to maximize space and comfort while reflecting the island's rich history and lively culture. From bold, colorful décor to plush bedding, every room provides a cozy retreat after a day of sightseeing. Here's what each room offers:br- Underwater Cabana: A calming blue suite with a King bed and Queen pullout couchbr- Chicken Walk: A relaxing green suite with a King bed and Queen pullout couchbr- Citrus Queen: A bright orange-themed suite with a King bed and Queen pullout couchbr- Birds of a Feather: A picturesque pink suite with a King bed and Queen pullout couchbr- Sunshine State: The largest one-bedroom suite with a King bed, 1.5 baths, and a Queen pullout couch in the living area—perfect for 3 guestsbrbrInside each suite, you'll find a mini-bar, mini fridge, coffee maker, and cable TV. Step outside to the shared rooftop deck, where sectional seating and turf flooring create a perfect spot for lounging or gathering with friends.brbr- The Penthouse: As the largest suite at Custom House Inn, this stylish three-bedroom, three-bath modern maritime escape is the perfect anchor for your group. As part of the compound, it creates a private retreat for up to 6 guests, complete with a sleek minimalist kitchen, full living room, and luxurious nautical vibes.brbrGuest Access:brOur convenient contactless check-in process ensures a smooth arrival. Personalized access codes will be sent prior to check-in for easy entry. The property includes both first- and second-floor units, each designed for comfort and privacy.brbrThe Neighborhood:brLocated in the heart of Duval Street, Custom House Inn is steps from Key West's best restaurants, bars, and attractions. Enjoy local favorites like The World's Smallest Bar, Fogarty's, Irish Kevin's, and Moondog Café, or stroll to the Hemingway House and other historic sites. For nightlife, Willy T's, Rick's Complex, and Fat Tuesday's are minutes away. While Duval's vibrant energy brings some noise, it also delivers unmatched excitement and convenience—allowing you to fully embrace the Key West experience!brbrGetting Around:brGetting around Key West is a breeze. Rent a bike, scooter, or golf cart, or hop on a pedi-cab for a fun ride. Many attractions are walkable, but Uber, Taxi, and Lyft are also available. Need help planning We're happy to offer recommendations!brbrParking Information:brPlease note there is no on-site parking. Several pay-to-park options are nearby:br- Fleming Street Pay-to-Park Lot (closest)br- 204 Simonton Streetbr- Caroline Street Outdoor Parking Lotbr- Park N Ride Old Town GaragebrbrOther Things to Note:br- Two suites and The Penthouse are on the second floor; three suites are on the firstbr- No washer/dryer on-sitebr- No pets allowedbr- Guests must be 25+ to reservebrbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo 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 Custom House Inn and enjoy the ultimate Key West vacation!brbrAt Colocada Vacation Rentals, we're dedicated to making your stay as relaxing and memorable as possible. Questions or need tips We're here to help!

Guest House

Custom House Inn | 8 BR Suite Compound on Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$1237.5

- Secret Villa II - brbrA Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own private pool. Secret Villa II is available for rent exclusively on VRBO and HomeAway. We have recently completed a total update of the pool deck to match the beauty and size of her sister property, Secret Villa I. Please Note there is a Security Camera On the Front porch. Please Contact the Property Manager To Have It Disconnected if you Wish brbrSecret Villa II is the perfect vacation rental for discerning, upscale clientele. The property is a newly renovated 3BR, 3BA home with a heated pool situated in the heart of old town on a quiet and private lane. The fenced-in private pool is surrounded by lush gardens, natural vegetation, and tropical canopies, providing our guests with the privacy and intimacy that Key West visitors are looking for. Newly renovated inside and out so that you and your party experience Key West in a clean & comfortable environment where everything is just right.brbrIf you are looking for additional accommodations our sister property Secret Villa I is available in the same compound. Please see our VRBO listing #754594 for availability. br- The Location - brbrSVII is just 1.5 blocks from Key West's most famous party area - Duval Street! Enjoy the hustle and bustle of live music and world renowned restaurants, then you and your party can retire to SVII's private, fence enclosed sanctuary. brbrSVII is conveniently located on a private lane just off Simonton, between Southard and Fleming (just behind the Marquesa Hotel). It’s an extremely unique location for such a large Villa. SVII provides the convenience of being within walking distance to all the action Old Town has to offer, while still allowing guests to retreat to the sanctuary, a much more tranquil atmosphere that only a home on a quiet Key West lane can provide. Although a driveway is provided, most guests find they leave the keys at home and instead walk or bike to local attractions - fine dining, bars, galleries, nightlife, shopping, museums, and much, much more! And although the heated pool may encourage you to relax and sunbathe at home, three of the most popular Key West beaches are within a minute's bike ride.brbrPlease note - one mid-sized car or small SUV can comfortably fit in the driveway.brbr- Secret Villa II is a Healthy Environment Experience -brbrAnyone who has traveled in the tropics knows humidity is the enemy, quickly turning even elegant venues into musty unhealthy experiences. No matter how much a place is cleaned or overly scented with perfumes to hide the problem, the only way to have a healthy house is to address humidity and air quality head on!brbrAt Secret Villa II, the entire structure has been renovated including the air quality and air handling equipment. All furniture, draperies, mattresses, pillows and linens are clean and new. All duct work was either replaced or cleaned with eco-friendly antimicrobial agents. The HVAC system includes HEPA filtration and whole house dehumidification. The house has hurricane impact windows and doors that seal in the low humidity and HEPA-clean air making it pleasant throughout the entire house.brbrAlso while guests may smoke their Havana cigars out by the pool, we have a “No Smoking” policy inside the house. The result is an extraordinarily healthy environment where guests wake up feeling refreshed, energized, and ready to meet the day!brbr- The Accommodations -brbrAll SVII rooms are large and comfortable making the house a perfect getaway for 2 to 3 couples. The 2nd floor has 2 master bedrooms each with an en suite bathroom - one with a California King bed and the other with a King bed. The upstairs bedrooms share a large outside porch where guests can enjoy a late night glass of wine while watching the night sky and taking in a cool evening breeze. The first floor bedroom shares a bath with the living room and comes furnished with a Queen sized bed. The first floor bedroom is perfect for in-laws or grandparents that may be part of your vacation party.brbrAll beds have recently been updated with double pillow tops, ultra luxurious, extra firm mattresses. All bedrooms include extra soft, high thread count sheets with 6 pillows, a comforter, extra sheets, blankets, towels, dark make-up removing towels, a ceiling fan, black-out curtains, smoke detector, safe, and flat screen TV. Every convenience has been thought-of and added, including even small conveniences such as powerstrips with USB connections on both sides of the bed. Although designed for 3 couples, the living room also includes a full-sized pullout bed.brbr- The Private Pool -brbrOne of the highlights of this home is the private pool area. Fully fenced and surrounded by lush tropical greenery for safety and complete privacy, this will undoubtedly be a primary gathering place for your group. The comfortable chaise lounges can be pulled into the sun or the shade right beside the pool. Sun bathing can be on the upper terrace or poolside, and multiple pool towels are provided. brbrThe pool area includes a propane grill for an outdoor BBQ by the pool. Enjoy the view from the upper terrace that overlooks the rooftops and the trees of Old Town, or mix-up some much-deserved cocktails in the blender as you watch the rest of your group play in the pool and the burgers cook on the grill. br br- The Living Area & Kitchen - brbrSecret Villa II boasts an extra large living room with high ceilings and luxurious modern furnishings including a 60” LED HDTV with Disney+, Hulu, and ESPN. Secure high-speed internet with wifi is available throughout the property. Floor to ceiling double french doors allow natural light to pour into the first floor all day while blackout curtains provide privacy at night. A full complement of games are located in the credenza under the living room TV (i.e. Poker chip set and playing cards, Clue, Monopoly, Cards Against Humanity, Yahtzee, Scrabble, etc.). brbrAmateur and master chefs alike will love their cooking experience in the fully equipped and spacious kitchen. If you enjoy staying in and creating your own meals, every high-end modern kitchen appliance can be found right in the comfort of your vacation home. The kitchen includes state of the art appliances and all of the tools and utensils you will need to prepare a meal at home when taking a break from the restaurant options of Key West. Open shelving allows guests to easily select the right wine, beer, or cocktail glass for your own happy hour (blender provided!). The outdoor patio, accessible from either the kitchen or living room, has seating for eight. brbrConveniently located at the end of the kitchen is a state-of-the-art, over-sized washer and dryer, making laundry tasks quick, easy, and finished while you’re out and about enjoying the town. brbr- Summary -brbrSVII is more than fantastic – instead it’s actually JUST RIGHT! Newly renovated, clean, comfortable, spacious, private, lush, and centrally located. brbrSecret Villas Key West is proud to represent this paradise home and to provide you with the vacation experience you’ve always wanted and deserved.

Villa

Secret Villa II @ Old Town: with Private Pool, close to Duval!

Key West, Florida, United States

Bed

Bath

6

Sleeps

$881.2

This is the luxury boutique resort you and your family and friends deserve. A few steps to famous Mallory Square and all of Key West’s attractions and restaurants. Gorgeous rooms, and pools. Sleeps 6. Right on the marina with all the cool yachts! You’re going to love it! Although we can’t guarantee a water view, it is right outside your door. The resort assigns the actual unit number when you arrive depending on who has checked the week prior. You may get lucky with the view because we are owners and always request a view. Have fun it’s a blast here! Order food in or just stroll outside for hundreds of food and drink choices. There is also a full kitchen to cook or make your own cocktails!

Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 20-27, 2026

Key West, Florida, United States

Bed

Bath

Sleeps

$246.92

Garden of Roses | Private Hot Tub, Prime Key West Location!brbrExperience the essence of Key West living at Garden of Roses, a beautifully restored conch-style home in a fantastic location. Just a block away from Duval Street, this monthly rental offers the perfect retreat for those looking to enjoy both comfort and convenience. With a private hot tub, lush gardens, and secure off-street parking, it's the ideal setting for a tropical escape.brbrThe Ambiance:brBlending historic charm with modern upgrades, this cozy Key West home comfortably sleeps up to 8 guests. The thoughtful layout provides privacy and space for everyone:br- Bedroom 1: King Bedbr- Bedroom 2: Queen Bedbr- Bedroom 3: Two Twin Bedsbr- Living Room: Sofa Bed for additional sleeping optionsbrbrThe open-concept living area is filled with natural light, creating a bright and airy atmosphere. Whether you're here to relax or work remotely, you'll appreciate the high-speed WiFi and multiple smart TVs with cable and streaming services. The modern kitchen, with granite countertops and stainless steel appliances, is fully equipped for meal prep, and the adjoining patio area offers a gas grill and outdoor dining space, perfect for enjoying a meal in the fresh air.brAfter a day exploring the island, unwind in the private hot tub or relax in one of the three serene outdoor seating areas, surrounded by lush greenery and sunshine.brbrGuest Access:brOur simple, contactless check-in process ensures a smooth arrival. You'll receive a personal access code ahead of time for quick entry.brbrThe Neighborhood:brLocated at the corner of Whitehead and Louisa Streets, this home puts you right in the heart of Key West. You're just steps away from the lively Duval Street, home to popular dining, shopping, and entertainment venues. Visit iconic landmarks like the Southernmost Point, the Ernest Hemingway Home, and the famous Blue Heaven restaurant. For beach lovers and history buffs, Fort Zachary Taylor Historic State Park is also nearby, offering both sandy shores and a historic fort to explore.brbrGetting Around:brKey West is easy to navigate by foot, but if you prefer to explore on wheels, there are many bike and scooter rental options close by. Fury and Island Bicycles offer convenient pick-up and drop-off services, and Minty's provides scooters and golf carts to get you into the island spirit. Alternatively, rideshare options like Uber and Lyft, or local taxis, such as Pink Taxi, are readily available. The home includes a spacious off-street parking area for those traveling by car.brbrOther Things to Note:br- The home is equipped with a private washer and dryer for your conveniencebr- Pets are welcome—just reach out for additional details. br- You'll also benefit from off-street parking, which is perfect for larger vehicles. br- Central air conditioning to keep you comfortable throughout your stay.br- Mid-stay cleaning services are available upon request.br- Relax and unwind in your very own private hot tub.br- Guests must be 25 years of age or older to reserve this property.br- A minimum stay of 30 days is required, in accordance with local regulations.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, pool, and common outdoor areas. No cameras are placed in private or interior spaces.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.

Private Vacation Home

Garden of Roses | Private Hot Tub, Prime Key West Location!

Key West, Florida, United States

Bed

Bath

8

Sleeps

$309.38

This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size bed and a balcony (resort view). This unit has a brand new kitchenette featuring new wood cabinets, granite countertop and new stainless appliances including a mini-refrigerator, microwave, 2 burner countertop range, coffee maker and dishes. The bathroom is also new with a beautifully tiled shower and vanity with granite countertop. New entertainment center features tons of storage, large flat screen cable connected TV and DVD player. For your added convenience, it comes with free wireless internet, iron & ironing board and an in-room safe.brbrThe Galleon Resort and Marina is located at the end of Front Street, 2 blocks from Duval and 3 blocks from Mallory Square. All of the attractions, shopping, fine restaurants and famous bars are only steps away. The Galleon is at the very beginning of the 'Harbor Walk' where you can find numerous charter boats, parasailing, snorkeling and scuba diving, glass bottom boat tours and sunset sailing. This is the best location in Key West and you will not need a car. The Galleon Resort has a beautiful pool and spa, exercise room, sauna, BBQ grills, waterfront restaurant and bar. Scooter, bicycle, jet skis and boat rentals are available on-site.

Galleon Resort Efficiency in the old town

Key West, Florida, United States

Bed

Bath

Sleeps

$437.68

Here in Key West we believe in One Human Family where everyone is welcome and treated like family. brbrKey West! .....it’s not just a place on the map, it’s a frame of mind, an Attitude…… come and let us share that Key West Attitude with you!brbrFully Renovated This is a Luxury Executive 1 Bedroom 1 Bathroom Penthouse. brOur kitchen features high end stainless steel appliances and a Keurig Coffee station with frothier. brbrThe interior features a dedicated work station, faux shutter doors on the bedroom and bathroom for privacy, Ship lap accent walls, vaulted ceilings and nautical colors.brbrThis 1 bedroom condo is considered to be very large by Key West Standards. 2 sets of Patio Doors opening on to the Balcony that provides a peek of the ocean, King Size Bed and a Queen Size Murphy Bed, Large well equipped Kitchen.brbrOur renovated bathroom features a Couples walk in shower (the shower heads both operate at the same time or individually.)brbrWe offer:br- Dedicated work areabr- Secure High Speed Wireless internetbr - Local and long distance telephone for continental USA and Canada.br- Printerbr- 2 Adult bicycles (The Best Way to Explore our little Island) br_ 2 Comfy chairs on the balconybr- Central A/Cbr- High quality Bedding and Linens. br- Stainless Steel appliances. br- Full size Washer and Dryer br- 2 Large Smart TV's ( Living area and Bedroom)br- HD Cable br - Assigned garage parking for 1 vehicle (Oversized vehicles and Golf Carts have to park outside)br- Poolbr- Hot tub br- Gym br- Sauna br- Private natural beach area br- Picnic/Grilling areabr- Tennis courts ( 1 clay court and 2 regular) br- Laid back Costal Decorbr- Stunning Courtyard with lots of little surprises, here you will see that Orchids do grow on trees! This is our little piece of Paradise!brbrIt should be noted that NOT everyone here is on vacation there are many full time residents so it is important to be considerate and respectful understanding that not everyone is in vacation mode. If you are looking for something a little wild this may not be the space for you.

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Key West, Florida, United States

Bed

Bath

Sleeps

$507.2

Your spacious oceanfront balcony will be a front row seat for a panorama of azure blue ocean and sky. There are touches of tropical whimsy everywhere, like the “Windblown Table Lamp” in the reading alcove, a quirky reminder that you have arrived in America's Tropical Paradise. And since you are in the tropics, it goes without saying that there are overhead fans in every room.brbrThe living area is bright and airy, with plenty of room for everyone to stretch out and relax. There's a large high definition flat screen TV with expanded cable service. Large sliding glass doors open onto that spacious ocean view balcony. The kitchen is completely equipped and newly renovated with brand new appliances and everything else you would need to prepare the most ambitious meal. The master bedroom has a queen size bed, walk-in closet and also has sliding glass doors to the balcony. The en-suite bathroom has twin vanities and a separate “water closet” for the toilet and oversize glass shower. The second bedroom has twin beds that convert to a king. The third bedroom has a queen bed. If desired, the second and third bedrooms become one spacious suite. The second bathroom has an extra large shower. 28 night Minimum Stay Please Inquire.brbrA POOL & JACUZZI RIGHT ON THE OCEAN...brbrThe large community pool and Jacuzzi are situated right on the oceanfront; you'll have those cooling ocean breezes all the time. There are a generous number of chaises and tables with umbrellas, and gas grills for those BBQ parties on the pool. If you have brought your own boat, you'll be able to keep it at one the many dry slips or wet slips available. Stand Up Paddleboard, Kayak, Jetski rentals are available. Contact the Dockmaster @ 305-360-2909.brThe Yellowfin bar and restaurant is across the parking lot.br28Day Min. Rental

Oceanfront Marina Condo With All Luxuries

Key West, Florida, United States

Bed

Bath

Sleeps

$426.14

Welcome to your dream residence in the heart of Key West, Florida! Nestled in a prime location, this 2-bedroom apartment offers the perfect blend of comfort, convenience, and the laid-back charm that defines Key West living. Situated in the heart of Key West, this apartment is a stone's throw away from the vibrant energy of Duval Street and the historic charm of Old Town. Immerse yourself in the island's unique culture, where lively restaurants, art galleries, and boutiques line the streets. Step into a thoughtfully designed living space that reflects the relaxed atmosphere of Key West. The open-concept layout seamlessly connects the living and dining areas, creating an inviting space for both relaxation and entertainment. The interiors are adorned with tasteful furnishings, capturing the essence of island-inspired living. This apartment features two bedrooms 2 bath's each offering a tranquil retreat after a day of exploring the island. Enjoy a restful night's sleep in well-appointed rooms designed with your comfort in mind. One of the highlights of this property is the inviting common pool area. Dive into the refreshing waters or lounge under the warm Florida sun. It's the perfect spot to unwind, socialize, or simply enjoy the tropical surroundings. With a location that boasts a high Walk Score, everything you need is within easy reach. From world-class dining options to quaint cafes and eclectic shops, Key West's best offerings are just a stroll away. Embrace the carefree island lifestyle and leave the car behind as you explore this enchanting community on foot. Welcome to your 2-bedroom sanctuary in the heart of Key West, where every day is an opportunity to soak in the sun, savor delicious cuisine, and relish the vibrant atmosphere that surrounds you. Don't miss the chance to make this apartment your vacation spot and experience the magic of paradise. Your perfect Key West lifestyle awaits!brbr** No elevator, stairs only to apartment

Winter Months Open Frogmore on Fleming in Downtown Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$190.13

STEPS TO DUVAL! WALK EVERYWHERE-- ALL THE SHOPS, RESTAURANTS AND BARS OF OLD TOWN! You wont need a car with this location. You can walk, bicycle, rent a scooter or golf cart to get around.brbrLA DOLCE VITA is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Historic District!! brbrSouthernmost Point and Southernmost Beach on the Atlantic Ocean are just 3 short blocks away! Southernmost Cafe also has a great Happy Hour!brAlso, one of our favorite spots is the Seaside Cafe which is on the water and has great drinks, pizza, salads. It is located next to Southernmost Cafe. brbrPlease check out our calendar for availability and our photos and video. brbr The condo is on the second floor of an old, beautiful, Key West style building with a wraparound balcony.br It has high 14 ft ceilings, a granite galley style kitchen, stainless steel appliances, refrigerator, freezer, ice maker, 2 burner glass cook top and microwave . It has cherry wood laminate floors, queen size bed w/ memory foam mattress, 75 inch flat screen Smart TV in living room, 35' Roku TV in bedroom, ceiling fans in living room and bedroom, full bathroom, crown molding throughout with recessed lighting on dimmer switches and also rope lighting on the ceiling throughout the condo for a cozy, relaxing feel. brbr The condo has a shared porch with 2 sitting chairs on a large wrap around balcony. brbrThere is a public pool at 300 Catherine St. one block away. It is the Community Center and has picnic tables, basketball courts and playground. Weekend hours vary. Their phone number is 305-809-3876. brbrDante's Pool & Raw Bar is located at 951 Caroline St, which has a large pool, full bar, Tiki bar and grill. It is a short bike ride away. Pets are welcome.brbrJust 3 short blocks away is Southernmost Beach which has Southernmost Cafe and offers breakfast, lunch, dinner and happy hour. brbrThree blocks to Southernmost Point on the Atlantic Ocean. Also, a few blocks away is Fort Zachary Taylor Beach which is a 20 minute walk. Fort Zachary Taylor Beach is Key West's most beautiful beach!brbrYou will not need a car with this location! Walk to all the shops, restaurants, bars and beaches of Old Town, Key West! brbrIf you would like to purchase any of the artwork in the condo, please inquire. Thanks! :)

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

Key West, Florida, United States

Bed

Bath

Sleeps

$350.36

This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, toaster, coffee maker. Perfect for a quick getaway, to enjoy the beautiful sunsets of Key West. The Galleon Resort is steps away from the famous Duval Street. Sunset tiki bar and Pirates Cove on premises. 3 blocks from Mallory Square and the beginning of “ Harbor Walk”. Scooter, bicycle, jet skis and boat rentals available on site. No need for a car once here.

Galleon Resort efficiency

Key West, Florida, United States

Bed

Bath

Sleeps

$298.76

Kingfish Keep | Lively Escape on Duval! Balcony!brbrKingfish Keep is the perfect escape in the heart of the historic district! This charming flat features an upstairs balcony that offers lovely views of the Duval Street, just steps away from shopping, dining, and the beach.brbrThe Space:brKingfish Keep comfortably accommodates up to four guests, ideal for families or friends. Inside, you'll find a cozy kitchenette equipped with a microwave, stove, and fridge, along with a private bathroom and dining area. The property includes a king bed for a restful night's sleep, while the balcony invites you to sip your morning coffee and enjoy some people-watching. This condo is also part of a larger home, Pescado Penthouse, allowing for group rentals if you're traveling with family or friends. Explore the vibrant atmosphere of Duval Street, where you can enjoy fine dining at nearby restaurants.brbrGuest Perks:brThis suite is dog-friendly. Stay connected with complimentary WiFi and two cable TVs. Access is made easy with our digital e-lock system, ensuring a smooth check-in process.brbrNeighborhood Highlights: Kingfish Keep places you at the center of it all! Right on Duval Street, you're just a short walk from the beach and iconic attractions like the famous Southernmost Point. Discover local cafes, shops, and nightlife right at your doorstep.brbrGetting Around: Key West is best explored on foot, but bike and scooter rentals are readily available for those looking to venture further. Rideshare options like Uber and Lyft make getting around the island convenient.brbrOther Things to Note:br- No parking is available on-site.br- Dogs are welcome! One dog (30 lbs maximum) with a $20 per night fee.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Kingfish Keep | Lively Escape on Duval! Balcony!

Key West, Florida, United States

Bed

Bath

4

Sleeps

$265.42

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

Yellowfin Ledge | Ideal Getaway On Duval! Balcony

Key West, Florida, United States

Bed

Bath

Sleeps

$246.36

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

Wahoo Way | Charming Hideaway On Duval Street!

Key West, Florida, United States

Bed

Bath

Sleeps

$766.93

Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!brbrPescado Penthouse is the ultimate getaway for families or friends seeking adventure in Key West! This unique property combines three charming condos—Kingfish Keep, Wahoo Way, and Yellowfin Ledge—into a single rental, providing ample space and convenience right in the heart of the historic district. With stunning views from the balconies and just steps away from the vibrant energy of Duval Street, you'll have easy access to shopping, dining, and the beach.brbrThe Space:brThis expansive rental comfortably accommodates up to nine guests, making it perfect for larger groups. Kingfish Keep features a king bed, a double sleeper sofa, and a cozy kitchenette, while Wahoo Way offers an additional king bed, both ideal for couples or small families. Yellowfin Ledge completes the trio with its inviting atmosphere, a comfortable queen bed, and a small twin sleeper sofa. Each condo includes its own private bathroom, ensuring everyone has their space. Enjoy morning coffee or evening cocktails on the balconies, taking in the lively sights and sounds of Duval Street.brbrTraveling with a smaller group Each of the three condos that make up Pescado Penthouse can be booked individually as well. Explore these unique spaces for the perfect Key West getaway! brbrKingfish Keep - https://www.colocada.com/rentals/kingfish-keepbrWahoo Way - https://www.colocada.com/rentals/wahoo-waybrYellowfin Ledge - https://www.colocada.com/rentals/yellowfin-ledgebrbrGuest Perks:brExperience the ease of contactless entry with our digital e-lock system for all units. The property is dog-friendly, allowing two small dogs (30 lbs or less) to join your stay for a small nightly fee. Stay connected with complimentary WiFi and unwind with cable TV in each unit.brbrNeighborhood Highlights:brPescado Penthouse places you at the center of it all! With Duval Street just outside your door, you're a short walk from the beach and iconic attractions like the Southernmost Point. Discover local cafes, bars, and shops, immersing yourself in the unique charm of Key West.brbrGetting Around:brKey West is best explored on foot, but bike and scooter rentals are readily available for those looking to venture further. Rideshare options like Uber and Lyft make getting around the island convenient.brbrOther Things to Note:br- This rental is located on the second floor.br- No parking is available on-site.br- Dogs are welcome! Two dogs (30 lbs maximum) with a $20 per night fee.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Pescado Penthouse | Vibrant Retreat on Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$508.84

MODERN TROPICAL JEWEL WITH STUNNING OCEAN VIEWS…brThis contemporary and spacious custom-built gated home will beguile your senses, luring you inside with the finest of amenities and stunning design. Just a stone's throw away from the infamous Southernmost Buoy, you are truly seated in the heart of paradise in this small gated community. Designer finishes and top-of-the-line fixtures can be found throughout and will soothe and spoil your inner pleasure-seeker. This vibrant and bustling area is ideal for those looking for all the excitement and frivolity of Key West and may not be ideal for those guests who are particularly sensitive to outdoor noises. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brLush landscaping beckons you onto the front porch where you can sit and sip your morning java while marveling over the exquisite view of the Atlantic Ocean. Enter your retreat and pass by a powder room before entering the Great Room. The crisp white-out kitchen comes complete with quartz waterfall-counter island, stainless steel appliances, walls of impact-resistant windows with loads of island sunshine spilling in to brighten your spirits. There is a desk area with a window view that adjoins the kitchen. Enjoy your fresh catch at the dining table with for 4, then scoot across the room to collapse on the roomy sectional and binge on your favorite shows with a nearby Sonos speaker system (also in all bedrooms).brbrSLEEPING ARRANGEMENTS:brOne downstairs bedroom is just off the living area and has two cozy twin beds (can be converted to a king), with matching bedside tables and reading lamps, large tv, clothing dresser, and hanging closet. The private bathroom features custom floor-to-ceiling tile, glass-door shower with single sink vanity. Travel up the stairs to access two more bedrooms. The first offers a plush queen bed, large TV and a bathroom with floor-to-ceiling tile shower/tub. The third bedroom has a luxurious king bed and sitting area. Two large TVs offer viewing in bed and sitting area. Enjoy another ocean view from your room! A huge walk-in closet stores your clothing and the bathroom offers a double sink vanity, floor-to-ceiling tile and a large glass-door shower with rain shower head. A laundry closet with stacked washer/dryer is included.brbrOUTDOOR LIVING…brLush foliage surrounds the home exterior and lures you outside to your private dipping pool (heated in the winter months), outdoor shower, gas grill and sun lounging chairs. A rooftop terrace and two levels of front porches with seating look out to unobstructed views of the glorious Atlantic vista.brbrPARKING...brThere is one designated parking space for this home.brbrBOOKING DATES:brThis home is only available as a monthly rental (28 night min). 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.brbrPETS...brDogs that are 30 lbs and under are permitted and a pet fee is required.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)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).

Private Vacation Home

SEA FOREVER ~ Downtown Ocean View Home w/ 3 BR, 3.5 Ba w/ Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$973.13

GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY VIEWS OF KEY WEST HARBOR, SUNSET KEY AND THE GULF OF MEXICO. (These views are also available from the master bedroom, living area and kitchen all day, every day)brbr4th FLOOR OCEANFRONT CONDO RENTALbrSleeps 6 / 1 Master King - 1 Guest Queen / 1 Queen pullout / Large private oceanfront balconybrbrEXCEPTIONAL LOCATION & CONVENIENCEbrThe Galleon Resort is located at the end of North Front St (literally steps from your elevator to Seaport Boardwalk happy hour bar menus, shops & multiple restaurants) / 2 blocks to Duval St + more restaurants, Mallory Square, Front Street eateries, bars and shopping—or cook steaks & seafood on our newly renovated paver picnic patio with 2 extra large Pro BBQ grills and free propane gas on demand + 3 round umbrella picnic tables / 3 HD cable TVs in condo / Free wireless internet / Free private parking / Secluded but very close to all the action / Car not necessary / Rental scooters, bikes, electric golf carts, fishing tour boats, wave runners all on-site to explore Key West from land or water / Oceanfront Tiki Bar & Pirates Cove Marina Bar & Grill on premisesbrbrRECOGNIZED & VOTED IN 2016-17-18 AS A TOP-25 TIMESHARE RENTAL RESORT BY TIMESHARE USERS WORLDWIDEbrbrBEAUTIFULLY LANDSCAPED OCEANFRONT SWIMMING POOL & HOT TUB, LARGE NEW OCEANFRONT COVERED TIKI BAR, NEW SUN DECKS & GAZEBOS, SMALL PRIVATE BEACH & OCEAN SWIM AREA w PLATFORM, PRIVATE FISHING PIER & NEW BBQ PATIObrbrFull-service resort with on-premises concierge, housekeeping, maintenance and security staffing with computerized door entry cards, security cameras, and room safes for guests.brbrChildren welcome. Suitable for seniors and handicapped with four elevators, ramps to pool, outdoor hot-tub, beach, Granite sitting ledges in Master Bathroom and open entry from walk-in shower to JacuzzibrbrThis 96-unit oceanfront property is accessible by car or boat, with free parking and rented boat slips / Great for families & sailboat crews / Marina next to resort to dock your boat / Full laundry, sauna / At the entrance to the Historic Seaport boardwalk / On the ocean in the heart of Key West's incomparable Old Town w tin-roof conch houses, historic museums & homes, unique shops, artist galleries, and quirky Duval Street entertainment / *Don't miss the nightly, world-famous Mallory Square Sunset Celebration (Unique Entertainment-Food-Art-Crafts) just 2 blocks from your condobrbrTHIS CONDO has a full size, fully equipped kitchen, breakfast area, wet bar w wine storage, washer-dryer, dining area, living room with entertainment center (55” TV, DVD player, AM-FM stereo, extra wardrobe closet, drawers) in living area, master bedroom with ensuite 2-sink vanity, closet, makeup vanity with extra device outlets, shower w attachments & jet-tub Jacuzzi, guest bedroom with full bathroombrbrFULL BALCONY with lighting has four chairs & table, and is accessible thru French doors in both the living room and master bedroom with sweeping front and corner views of Key West Harbor, Sunset Key and Gulf of Mexico.brbrEXTRA AMENITIES include 3 HD TVs with cable, DVD player, AM-FM stereo, iron & ironing board, jacuzzi tub, in-room safe and free private/secured wireless internet / Pool towels & bed linens provided / Kitchen and Master bath received complete granite & appliance renovation with new living room furniture in last 2-3 years / There is 1 free parking space for each unitbrbrQuiet and secluded, yet very close to restaurants & shopping / On-premises large oceanfront swimming pool with jetted hot tub / New oceanfront decking, lounges and umbrellas surround the resort / On-premises oceanfront TIKI BAR and Marina-side PIRATES COVE breakfast & lunch bar-grill / On-premises GIFT SHOP with unique, hand-painted & personalized souvenirs at driveway entrance / Small private beach with private fishing pier / New picnic patio with new extra large Pro BBQ grills and umbrella picnic tables / Roof-top observation deck provides amazing 360 degree views of Key West

SEAPORT PANORAMA at Galleon Resort-Beach-Pool-King-BBQ-Kitchen views!

Key West, Florida, United States

Bed

Bath

6

Sleeps

$410.63

Luxury 46-ft Sea Ray yacht in Key West! Sleep up to 6 guests in 2 private cabins, each with ensuite bath and A/C. Perfect for romantic getaways or small groups seeking an unforgettable waterfront experience. Wake up to dolphins, explore pristine waters, and watch stunning sunsets from your private deck. This meticulously maintained express cruiser offers hotel comfort with the freedom of the open sea. Your paradise floating retreat awaits! Discounted ocean excursions available upon request!brbrThe spacebrbrWelcome aboard your private floating hotel in Key West!brbrWe have two identical yachts available on VRBO – perfect for larger parties or multiple families traveling together! This is Grand Admiral 1.brbrThe Grand Admiral is our smallest yacht but it offers plenty of space for up to 6 guests. It has 2 full bed and 2 full baths plus an extra pull out bed that could sleep an additional 2 guests or kids.brbrNote: if you have needs to fit a larger sized group please check out our other listings! We have additional yachts in the same marina that you can book for bigger groups. Just let us know how many beds and cabins you need and we will make you a special offer to accommodate your group size!brbrYou will love waking up on the water in the peaceful Stock Island Marina. A break from the ordinary hustle and stress of a hotel experience.brbrThe Stock Island Marina features tons of amenities which you have full access to:brbrBarbrPoolbrGymbrSaunabrParkingbrLaundry areabrTiki Grilling AreabrBeach (one of the few in Key West)brAccess to public transport (minutes from downtown Key West)brAnd more!brbrOur private on site concierge will help you with any questions you may have and help you plan out your activities for Key West.brbrWe also offer optional ocean excursions for you to take the yacht out for either a sunset cruise or a half day or full day experience on the water. Inquire about the excursions as you can get a discount for being our guest through VRBO.brbrThe Grand Admiral Floating Resort is perfect for:brbrCouplesbrFamiliesbrAnyone wanting a break from the ordinarybrBoat enthusiastsbrbrIf you have questions let us know and we will help you plan the perfect Key West Getaway with our floating hotel and resort!brbr- Vadim from LaRoma YachtsbrbrGuest accessbrGuests have access to the yacht and all the resort amenities including:brbrGymbrPoolbrBeachbrParkingbrTiki Bar PierbrGeneral StorebrAccess Point for public transportationbrbrOther things to notebrThis listing is for your very own floating hotel in Key West. You can use it to explore the area and enjoy the wonderful amenities included.brbrIf you would like to book an additional ocean excursion, just let us know! We will give you a nice discount on either a sunset cruise or full or half day out on the water.

House Boat

Romantic Yacht Stay Key West + Amenities Unit 1

Key West, Florida, United States

Bed

Bath

Sleeps

$781.93

Charming Key West Oasis – Your Private Slice of Paradise!brbrEmbark on a month-long journey of relaxation and exploration at Seacret Paradise, a hidden gem tucked away in the heart of Old Town Key West. Located just two blocks from the Key West Express and Dry Tortugas ferry terminal, and mere steps from Old Town Bakery, Dive Bar, and Eaton Good, this private retreat blends peace, comfort, and unbeatable access to all the island’s magic.brbrThis charming four-bedroom, three-and-a-half-bath home comfortably accommodates up to nine guests and is ideal for couples, families, or anyone looking to immerse themselves in the Key West lifestyle. Enjoy bright indoor-outdoor living, a sunny balcony, a fully equipped kitchen, and a quiet lane location just minutes from the best dining, music, and waterfront sights in Old Town.brbrBooking Requirements: To ensure a smooth stay, all reservations require a signed rental agreement and a refundable security deposit hold. The deposit hold is $500 for and will be placed on a credit card 2–3 days prior to arrival and released within 5–7 days after check-out, provided no damage or policy violations occur. A Guest Service Fee is included in all reservations and varies based on length of stay.brbrPlease note: In accordance with City of Key West regulations, this property requires a minimum 28-day stay. This allows you to settle in, unwind fully, and explore the island at your own pace.brbrPet Policy: One dog under 30 lbs allowed with owner approval and pet depositbrbrCleaning Fee Breakdown:brTo ensure cleanliness and comfort during your extended stay, the $650 cleaning fee includes a Mid-Stay Clean (A full refresh halfway through your 28-day visit) and a Post-Departure Clean (A deep clean to prepare the space for future guests)brbrSome Additional Amenities (see amenities for full list):brPack-n-play and portable high chair available in upstairs bedroom closetbrFast Wi-FibrSmart TVsbrStrong A/CbrWasher/dryerbrDishwasherbrIce Maker in FreezerbrOne off-street parking spot (compact fit)brbrbrWhether you're here to write your next chapter, chase sunsets, or enjoy fresh croissants every morning, Seacret Paradise offers everything you need to live like a local—luxuriously.

Private Vacation Home

Old Town Seacret Paradise! 4 BR with Pool!

Key West, Florida, United States

4

Bed