Vacation Condo Rentals By Owner In Key West, FL

$360.8

Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach

Key West, Florida, United States

This condo has been grandfathered in to allow for weekly rentals. One of only a few with City approval. This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in the Truman Annex, a gated community of private homes and condominiums. Located inside the Truman Annex is Truman's Little White House Museum, Eco-Discovery Center, Water Park for small children and Fort Zachary State Park. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin beds that are easily converted to a king sleeper, a sofa sleeper, full kitchen, living room, washer/dryer and two private balconies one overlooking the swimming pool and the other facing the courtyard. Free assigned parking spot and Free Wi-fi. Steps from famous Duval Street, sunset celebration and all the downtown action one desires. High demand book early.

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6

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$732.8

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Porter Paradise at the Truman Annex in Key West

Key West, Florida, United States

This charming getaway in the prestigious Porter Court is located in the award winning Truman Annex in Old Town Key West. Beautifully appointed with relaxation and fun in mind, this property has recently been updated. The master bedroom features a king bed and a twin. The second bedroom overlooking the pool includes a private deck, a queen sized bed, and an en suite full bathroom. The first floor includes a washer and dryer and a powder room. There are 19 town homes nestled around a central crystal blue pool. We like to call this the 'gated community within a gated community' as this compound has security gates for access. It's the perfect spot to decompress and let life's worries slip away, and enjoy your own little piece of paradise. There is assigned parking and quick & easy access to Duval/Old Town/nightlife/restaurants/beaches and water activities. brPlease note: This property is monthly rental - the minimum rental period is 29 nights/30 days, except for February, which is 28 nights!!!

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3

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6

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Select Dates for Price

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Island Time Casa – Modern Key West Oasis w/ Pool

Key West, Florida, United States

Welcome to Island Time Casa, your ultimate family-friendly retreat nestled in the heart of Key West’s prestigious Casa Marina district. This spacious condo boasts three beautifully-appointed bedrooms and three and a half modern bathrooms, accommodating up to ten guests with ease, making it the ideal choice for multi-family gatherings or multi-generational vacations. brbrExperience the charm of Key West with sunny porches and breezy balconies that are perfect spots for sipping morning coffee, enjoying leisurely family meals, or watching breathtaking island sunsets. Inside, you'll find a full kitchen equipped with all the essentials to cook up delicious meals, coupled with a cozy dining area that invites family and friends to gather around. brbrThe convenience of an in-unit laundry adds to the comfort, ensuring sandy towels and swimming suits are dealt with effortlessly. Step outside to enjoy the exclusive amenities such as a shimmering pool, tennis courts for the sport enthusiasts in the family, and a grill area for the quintessential vacation barbecue. brbrIsland Time Casa is suitably located within walking distance to all local attractions including the Southernmost Point, and the vibrant scenes of Duval Street. Leave your car behind in our free parking area and explore the neighborhood by foot or bike, embracing the laid-back island life. Take peaceful walks, build sandcastles on the beach, or simply soak in the salt air — every moment is a treasure at Island Time Casa. brbrThe property promises a blend of relaxation and accessibility, providing the perfect backdrop for creating lifelong family memories. Whether you’re here to unwind or explore, you're officially on Island Time.brbrPlease note: All cancellations are subject to a cancellation fee, which varies depending on the cost of your booking.

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$450.91

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Tropical Escape at Sunrise

Key West, Florida, United States

This luxurious recently renovated condo features a wonderful contempory interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests only. Must be 25 and older.brbrThe spacebrOur place is good for couples, business travelers and families with kids.

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$192.25

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ADRIFT IN KEY WEST at the Truman Annex in Key West

Key West, Florida, United States

Stunning, Modern Nautical-themed 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completely transformed. Fully appointed, sleek kitchen with all new appliances (oven/microwave combo unit), lighted kitchen drawers, washer/dryer in unit, comfortable private back patio oasis with comfortable furniture for lounging and entertaining. and outdoor Shower. End unit, bike rack right outside, gated community. Conveniently located in the Shipyard Complex of the Truman Annex just steps from the active lifestyle of Duval Street, shopping, dining, and night life. Also steps from Mallory Square for gorgeous sunset views and the new Truman Waterfront Park. Assigned off street parking for 1 vehicle. brPlease note: This property will require a minimum of a 28 night stay.

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$527.19

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Waterfront Property - Marina Access - Spacious - Excellent Key West Condo

Key West, Florida, United States

Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just three miles from vibrant Duval Street, and four miles from historic and majestic Mallory Square.brbrThe property features two pools, a hot tub, park-style grills, picnic tables, onsite bar, and much more.brThis spacious two bedroom condo features a king primary suite with hardwood flooring, a connecting ensuite full bathroom with shower and bath tub. The guest bedroom features a queen bed with wood flooring. The condo also features a full kitchen, with a full refrigerator, microwave, stove, oven, dishwasher, coffee maker (drip style), toaster, blender, dishes and utensils. The living room features a queen-size sleeper sofa, HD TV, a dining area and access to a private patio. This is a two-story condo and the bedrooms are upstairs.brbr*Must climb stairs — Stairs required to access the unit, Stairs may be required to access bedroomsbrbrGuest must be 25 yrs old to rent and check-in to this unit.brbrUnits are assigned in seven night increments, multiple week stays may be booked, room moves may be required.brOccupancy limits are strictly enforced.brbrNo RVs, campers or mobile homes may be parked on the premises. Parking is limited to two (2) vehicles per unit.brbrWelcome Center hours of operation are: Sunday to Thursday 9am – 5pm and Friday/Saturday 8am – 10pm. Late arrivals must call the welcome center for arrangements.brbrAn ID and a credit card is required upon arrival for a refundable security deposit.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.brbrGumbos is not currently operating as a bar or restaurant.brbrLaundry facilities located on top floor of buildings for a fee. Towel Exchange is not available.brbrPictures are representative of units on property. All feature similar layouts, decor and amenities. Property features most 2 story units. There exists a chance you may be assigned a single story unit. Specific unit is assigned at check-in by the front desk.

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$326.25

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Tropical Paradise In Key West-Coconut Beach Resort - Avail 4/24/27 to 5/1/27

Key West, Florida, United States

Book it before it's gone! 7 Day rental - available from Saturday 4/24/27 to Saturday 5/1/27 only.brbrCozy and comfortable 1 BR efficiency condo at the spectacular Coconut Beach Resort! Enjoy the lap of luxury at this private Timeshare property in beautiful Key West, located along the southern coast of the island. With its private beach, large pool, and sun deck, this exclusive property is a paradise, complete with lush tropical landscaping everywhere you look. This unit itself was completely renovated recently, has a private entrance, faces the street, and is well appointed and comfortable. It features a king-size bed, a full bath and central air conditioning. Step out onto your own private balcony, where you can relax and listen to the breeze through the palm trees. The hidden closet provides some unexpected surprises too, including a microwave, small refrigerator, even a coffee maker. You’ll spend your days where everyone does, around the magnificent common area facing the ocean, where the trees and tropical foliage abound. The pool area is amazing, with plenty of places to relax – either right in the sun, or in your own shady spot. The heated pool itself is magnificent, and you’ll love the swimming. You’ll want for nothing – there’s a hot tub out there, gas grills, rest rooms, even a water cooler to keep you hydrated. You can even enjoy your own private sunsets, right on the premises if you like. CBR is a stunning, beautiful place and it’s a short walk (or bike) to all the fun on Duval Street.brbrThis is a Timeshare Resort, and I’m the owner of this specific week. This is a Saturday to Saturday rental. Check-in time is Sat at 4pm (you can sometimes get in earlier), and you’ll need to check out on the following Saturday by 10am. There is a mid-week housekeeping crew that will tidy things up as well – no extra charge.brbrI’ve posted some of my own personal photos, and have been an owner at Coconut Beach Resort for over 20 years. Check out more photos on CBR’s site - coconutbeachresort . combrbrRent elsewhere for MUCH MORE per night, and you won’t get the amenities that CBR has. The dates and price are not flexible, and this unit is a 7 Day rental only, and available from Saturday 4/24/27 to Saturday 5/1/27 only.

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1

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2

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$305.76

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The Butterfly Nest | Newly Updated w/ Shared Pool

Key West, Florida, United States

The Butterfly Nest | Newly Updated w/ Shared PoolbrbrEscape to The Butterfly Nest, a serene, beautifully designed 2-bedroom condo located in the tranquil Sunrise Suites community on the southeast side of Key West. Just a mile from the pristine beach and a quick 10-minute ride to the lively Duval Street, The Butterfly Nest offers the perfect blend of relaxation and adventure. Whether you're basking by the pool, exploring local attractions, or enjoying the comforts of this charming retreat, The Butterfly Nest promises an unforgettable Key West experience.brbrThe Ambiance:brStep into The Butterfly Nest and immerse yourself in a cozy, thoughtfully decorated retreat that exudes comfort and charm. The condo features a master bedroom with a king-sized bed and a private ensuite bathroom, while the second bedroom offers a queen-sized bed with convenient access to the hall bathroom. A plush blue sofa in the living room converts into a queen-sized sleeper, making the space perfect for up to six guests. The open-concept living area invites relaxation, whether you're enjoying a meal prepared in the fully equipped kitchen, lounging on the couch with cable TV, or stepping out onto the private balcony with seating for four. With central air conditioning and all the comforts of home, The Butterfly Nest is the ideal space to unwind and recharge.brbrGuest Access:brEnjoy a seamless arrival with our contactless check-in process—guests receive a personalized access code three days before arrival. During your stay, take advantage of Sunrise Suites' exceptional shared amenities, including:brbr- Communal heated pool and hot tubbr- Tennis courtbr- Scenic walking paths and biking trailsbr- The unit is easily accessible via stairs or elevator, ensuring convenience for all.brbrLocation Highlights:brThe Butterfly Nest is ideally located in the peaceful Sunrise Suites community, offering easy access to Key West's best attractions. The beach, with its turquoise waters and loungers, is just a mile away, while the vibrant restaurants, bars, and nightlife of Duval Street are only a 10-minute drive. Key West International Airport is also conveniently close, making travel a breeze.brbrGetting Around:brThe condo includes parking for your convenience. Bike, scooter, and golf cart rentals are readily available nearby, allowing you to explore Key West's charming streets with ease. Taxis and rideshare services are also a great option for getting around.brbrOther Things to Note:br- Pet-Friendly Policy: Pets are welcome!br- Maximum weight: 40 lbs per petbr- $20/night per pet (2-pet maximum)br- Please notify us if you plan to bring your furry friend!br- A private stackable washer/dryer is available in the unit for added convenience.br- 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, pool, parking areas, 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.

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2

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6

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$314.6

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The Andros | Incredible Views w/ Shared Pool

Key West, Florida, United States

The Andros | Incredible Views w/ Shared PoolbrbrEscape to The Andros, a serene, beautifully designed 2-bedroom, 2-bath condo nestled in the tranquil Sunrise Suites community on the southeast side of Key West. Just a mile from the beach with its stunning aqua-blue waters and loungers, this charming retreat offers the perfect mix of relaxation and adventure. Whether you're soaking in the hot tub, exploring the vibrant attractions of nearby Duval Street, or unwinding on your private balcony with breathtaking sunset views, The Andro's is your ideal Key West getaway.brbrThe Ambiance:brStep into The Andros and experience a harmonious blend of modern comfort and tropical charm. This inviting fourth-floor condo accommodates up to six guests, featuring a king-sized bed in the master bedroom, a queen-sized bed in the second bedroom, and a queen pullout sofa in the living area for extra guests. The fully equipped kitchen makes cooking a pleasure, while the private balcony provides exquisite views of the surrounding salt marshes. With central air conditioning, free WiFi, and cable TV, Butterfly Nest offers all the comforts of home in a serene island setting.brbrGuest Access:brArrive with ease through our contactless check-in process, where you'll receive a personalized access code three days before your stay. During your visit, take advantage of the many shared amenities, including:brbr- A heated pool and hot tubbr- Tennis courtbr- Walking paths and biking trailsbr- The unit is easily accessible via stairs or elevator, ensuring convenience for all guests.brbrLocation Highlights:brThe Andros is perfectly situated within the peaceful Sunrise Suites Resort, just 10 minutes from the lively restaurants, art galleries, and nightlife of Duval Street. For breathtaking evening entertainment, visit the nearby Sunset Celebration at Mallory Square. The resort itself offers a corner store, spa, and scenic trails, while the Key West airport is conveniently located nearby for stress-free travel.brbrGetting Around:brEnjoy the convenience of one private parking spot under the building (spot #155), with additional parking available on a first-come, first-served basis. Explore Key West by bike, scooter, golf cart, or even on foot, with many attractions within walking distance. Rideshare services and taxis are also readily available for longer trips.brbrOther Things to Note:br- Pets are welcome (40 lbs maximum per pet) with a $20 per pet, per night fee. Please let us know in advance if you'll be bringing pets.br- A private stackable washer/dryer is available in the unit for added convenience.br- The unit is located near the airport, offering easy accessibility.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, pool, parking areas, 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.

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$235.98

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Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!

Key West, Florida, United States

BIlly's Blue Heaven is fresh, clean and Pristine. We have updated the condo with all new paint, a new Smart Tv in the second bedroom, new additional living room chairs, new beds/linens/pillows throughout, all new flush mount ceiling lighting and all new wall switch controlled ceiling fans. Our condo Includes one private parking spot directly in front of the condo. Just a two minute walk to Duval Street and only 300 steps to the world famous Ricky's Blue Heaven Restaurant. The balcony overlooks Truman Annex 's lush landscaping and just a 30 second walk to the shared swimming pool. A short walk or bike ride to Fort Zachary Taylor State Park and Beach. One of the best beaches on the island. You are a moment from Mallory Square where sunset is celebrated every night with world class street theater. The condo is outfitted with a washer/dryer, fully equipped kitchen, pots and pans, towels, linens, central air conditioning, off street parking for one auto and pool with close beach access. This is a Saturday to Saturday rental and is non smoking.brbrA unique feature of this property is our three bicycles so you don't have to rent! Key West is only two miles by four miles so nothing is too far away. Fly into Key West Airport and take a taxi to Truman Annex. You have THREE bikes and there's really no need to rent a car during your stay, as there's always the free trolley to get you around the island if you're not into bike riding! Big baskets on our bikes make shopping easy. Our kitchen has a blender. The bathroom has a newly remodeled freshly tiled walk in shower with dual shower heads and a rain water hand held sprayer.brbrOne bedroom has a queen bed and the second bedroom has two twin beds. Maximum of four guests at our condo!Gorgeous decor includes home theater sound system with Bluetooth, flat screen TV's, DVD, and a CD player. brbrTRAVEL INSURANCE IS NOW AVAILABLE THROUGH GENERALI/CSA - CALL FOR INFORMATION AT 800-349-8218 AS HOMEAWAY HAS RECENTLY PARTNERED WITH THEM!

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$282.45

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Seaside Condo, DECEMBER SPECIAL

Key West, Florida, United States

Upon waking in the morning we hear the murmuring of tropical birds , feel the gentle sea breezes and the fragrance of jasmine. When we go out from the apartment we can see the sea across the street and catch the sun rise if we wake early. Relax with a drink on the south facing balcony that looks out onto a spacious enclosed garden with palm trees, bougainvillea and 2 pools. Walk across the street to Smather's Beach for swimming and and snorkeling. Later take a stroll in Old Town or visit Fort Taylor Park and its beautiful beaches. In the evening pick up some fresh shrimp to prepare a gourmet meal in our full kitchen with the freshest seafood on the east coast. Or if you prefer head for downtown where there are literally dozens of sophisticated and alluring restaurants. The apartment is spacious and bright and filled with the art of my wife Marina's father. Key West is the ultimate winter beach destination.brATTENTION: Utilities included. Tenant will pay amounts exceeding $100 per month for ELECTRICiTY usage brbrKeywords: flat, apartment

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$585.49

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Key West's Crown Jewel

Key West, Florida, United States

Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath with approximately 1350 square feet of living space. Guests will enjoy absolutely breathtaking ocean views and the colors of the sunset from the 35-foot balcony, as well as from both bedrooms and the living room.brbrThe Living spaces:brThe wood beamed, soaring ceilings of the living room provide an extremely open feeling. Upgraded appointments include high speed (up to 100 mbps) wireless internet access via cable modem (via your wireless device), a 65” Samsung Ultra HD LED TV with high-definition Cable TV, Blu-Ray Player and a Bose Soundtouch music system in the living room. Queen-size sleeper sofa with memory foam topper in living room. A large, fully-equipped renovated kitchen with granite countertops and stainless steel appliances. Keurig Coffeemaker.brbrThe Bedrooms:brThe main bedroom has king-size bed with Tempur pedic Brand memory foam mattress with ensuite bathroom. The bath has 'spa style' shower with body sprays.brbrThe second bedroom has king-size bed with memory foam mattress and luxurious linens on the beds.brbrSamsung flat-screen TV's with Hi-Definition Cable TV and Blu-Ray Players in both bedrooms, access to YOUR Netflix, Hulu, HBO GO, Amazon Video accounts via Smart TV Hub in living room and both bedrooms, USB charging station at all bedsides, Bluetooth speaker at bedsides. Enjoy Key West IN STYLE!brbrThe property features a 70 ft pool fronting the Atlantic Ocean. A 12-person jacuzzi awaits. A courtyard changing room sauna is yours to enjoy. There is a Fitness Room, large picnic and barbecue area surrounded by the tropical gardens.brbrOne clay and two hard court lighted tennis courts are yours to enjoy at no additional cost. The largest beach in Key West, Smather's Beach, is adjacent to this condominium complex, offering white sand, palm trees, lounge chair and umbrella rentals, volleyball nets, sailboat rentals, and parasailing. An extensive leisure trail for walking, jogging, and bike riding fronts this beach.brbrOld Town, Key West's hub of shopping, dining, live entertainment, art galleries, and sightseeing, is just one-and-one-half miles away. Here you will enjoy all that ''downtown Key West'' has to offer, but will greatly appreciate coming back to your peaceful surroundings at the end of the day (or night!) to recharge. Parking for one vehicle in reserved space in the gated garage is also included. There is also elevator access. br*Disclaimer**br*The peak sargassum season in Key West is typically from July thru September and possibly June. You may see significant amounts which can impact your stay. While the naturally occurring seaweed itself is not dangerous, it can accumulate on beaches, producing a foul odor and potentially harboring organisms that cause skin irritation. We do not provide discounts for the situation.

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$441.0

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Waterfront Property - Marina Access - Spacious - Excellent Key West Condo

Key West, Florida, United States

Featuring direct marina access and located just 2 miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just 3 miles from vibrant Duval Street, and 4 miles from historic and majestic Mallory Square.brbrThis two bedroom condo features a spacious primary bedroom with a king size bed and hardwood flooring, a connecting ensuite full bathroom with shower and bathtub. The guest bedroom features a queen size bed with wood flooring as well. The condo also features a full kitchen, with full sized refrigerator, microwave, stove, oven, dishwasher, coffee maker (drip style), toaster, blender, dishes and utensils. The living room features a queen-size sleeper sofa, HDTV, dining area and access to a private patio. Most condos are two stories and the bedrooms are upstairs.brbrThe property features two pools (seasonally heated), a jacuzzi, park-style grills, picnic tables, and much more.brbr*Please note, unit may have stairs, use of stairs may be required to occupy the unit.brbrGuest must be at least 25 yrs of age to rent and check-in to the unit.brbrGumbos is not currently operating as a bar or restaurant.brbrLaundry facilities located on top floor of buildings for a fee. The property does not offer towel exchange.brbrPictures are representative of units on property. All feature similar layouts, decor and amenities. Property features most 2 story units. There exists a chance you may be assigned a single story unit. Specific unit is assigned at check-in by the front desk.brbrOccupancy is limited to six guests total, per two-bedroom unit. With two people, per bedroom plus an additional two people on the sleeper sofa. Property will not allow overcrowding of the unit beyond the existing bedding, with no exceptions.brbrNo RV's, campers or mobile homes may be parked on the premises. Parking is limited to two vehicles per unit.brbrEarly check-ins are not available. Check out time is 10 a.m. Please observe this rule, as the housekeeping staff needs time to prepare for the next arrival. Upon leaving, please secure all windows and doors, load the dishwasher and start, remove all trash, and strip beds.brbrLimited - service availability of marina onsite. Boat slip is $200. Parking on gravel is $75 (very limited availability). Parking boat in a parking spot is $150. (No boat ramp - no fuel supplied on premises). Please inquire for availability prior to booking. (subject to change at any time).brbrAlthough Coconut Mallory is a non-pet friendly resort the property does allow Service Animals in accordance with the Americans with Disabilities Act. Guests may also be accompanied by a certified Emotional Assistance Animal as long as written documentation of the Emotional Support Animal's legitimacy is provided at check-in. A Non-refundable $320.00 Cleaning Fee for your Assistance Animal will be due at the time of check-in.brbrThe property will provide bed linens, starter packages of detergents, bath soap and paper products. Please be sure to pack any specialty items that you may require during your stay.brbrCoconut Mallory requires a credit card and photo id at the time of check-in. This credit card is held for potential unit damage, missing items, or incidental charges during the stay.brbrPictures are representative of the unit, decor may vary. Units are assigned after booking, in seven night increments. Multiple week stays may be booked, room moves may be required.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

2

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2

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6

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$253.13

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Key West-Coconut Beach Resort - Avail 11/14/26 to 11/21/26

Key West, Florida, United States

Book it before it's gone - 7 day rental - available from Saturday 11/14/26 to Saturday 11/21/26 only.brbrCozy and comfortable 1 BR efficiency condo at the spectacular Coconut Beach Resort! Enjoy the lap of luxury at this private Timeshare property in beautiful Key West, located along the southern coast of the island. With its private beach, large pool, and sun deck, this exclusive property is a paradise, complete with lush tropical landscaping everywhere you look. This unit itself was completely renovated recently, has a private entrance, faces the street, and is well appointed and comfortable. It features a king-size bed, a full bath and central air conditioning. Enjoy sitting out on the private balcony outside of your room, where you can relax and listen to the breeze through the palm trees. The hidden closet provides with some unexpected surprises too - including a microwave, a toaster, small refrigerator, even a coffee maker. You’ll spend your days where everyone does, around the magnificent common area facing the ocean, where the trees and tropical foliage abounds. The pool area is amazing, with plenty of places to relax – either right in the sun, or in your own shady spot. The heated pool itself is magnificent, and you’ll love the swimming. You’ll want for nothing – enjoy the hot tub, gas grills, rest rooms, even a water cooler to keep you hydrated. You can even enjoy your own private sunsets, right on the premises if you like. CBR is a stunning, beautiful place and it’s a short walk (or bike) to all the fun on Duval Street. brbrThis is a Timeshare Resort, and I’m the owner of this specific week. This is a Saturday-to Saturday-rental. Check-in time is Saturday at 4pm (you can usually get in earlier), and you’ll need to check out on the following Saturday by 10am. There is a mid-week housekeeping crew that will tidy things up as well – no extra charge.brbrI’ve posted some of my own personal photos, and have been an owner at Coconut Beach Resort for over 20 years. Check out more photos on CBR’s site - coconutbeachresort . combrbrRent elsewhere for MUCH MORE per night, and you won’t get the amenities that CBR has. The dates and price are not flexible, and this unit is a 7 Day rental only, and available from Saturday 11/14/26 to Saturday 11/21/26 only.

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$188.91

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THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!

Key West, Florida, United States

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCHARMING 2ND FLOOR CONDO IN STUNNING SHIPYARD COMMUNITY OF TRUMAN ANNEX…brDelight in this cozy gem of southernmost island living, a 2 bedroom, 1 bath second floor dwelling with a balcony that overlooks verdant landscaping and a sparkling shared pool! Slide on your comfiest sandals and immerse yourself in the excitement of Duval Street, just 2 blocks away. You are walking distance to the island's hot spots: Fort Zachary State Park Beach, The Green Parrot, Sloppy Joe's, Hemingway's Home and Mallory Square - home of the famous nightly Sunset Celebration.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter this light and airy open living area that is colorfully and tastefully decorated to ease you into a sense of well-being and tropical tranquility. You and your loved ones will enjoy a cool respite after a day in the sultry sun, sharing relaxed conversation on the cozy furnishings or decompressing with your favorite movies on the wall-mounted TV. The fully equipped and well-stocked kitchen will inspire you to practice your culinary skills, complete with granite countertops, stainless steel appliances and all the tools a chef will need. Dine or play your favorite board game at the table for 4. brbrSLEEPING ARRANGEMENTS…brSlip into a peaceful sleep in one of the two bedrooms with plush queen beds. Both rooms offer flat screenTVs, cooling ceiling fans, clothing dressers and nightstands with power ports. The shared bathroom has been updated with a walk-in shower and there is a full washer/dryer closet for your convenience.brbrOUTDOOR LIVING…brOpen the French doors of the coastal living room to your balcony with umbrella table and chairs, a superb spot for morning coffee or dining outdoors. a second balcony resides just off the kitchen, with a lounge chair for napping or reading your favorite novel. The Shipyard in Truman Annex is a charming, tree-shrouded hideaway with serene walking paths and lanes. The beautiful community pool is lined with lounge chairs and is perfect for soaking up the Key West sun.brbrPARKING...brThis home does offer parking for one vehicle, just steps from the front door - (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community.brbrPETS...brThis is a pet friendly home with a required pet fee. Please include the size and breed when inquiring. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet 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. brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.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!brbrYOUR SLICE OF PARADISE IS CALLING...

2

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1

Bath

4

Sleeps

$130.98

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Back to the Island - Old Town Key West 2nd Floor Condo

Key West, Florida, United States

The front door to this second floor 1 bedroom / 1 bath vacation spot opens to a perfect lesson in space mastery and historic spirit. Hardwood floors, a myriad of bright windows, and vaulted ceilings bring warmth and light in. Step out onto the front balcony or the back balcony to experience the stunning weather of the island firsthand. There’s a lovely, heated pool & spa for the exclusive use of guests in this compound of four units. Another coveted amenity is the assigned off-street parking. And if that’s not enough, the location, less than four blocks off the amazing Duval Street, puts you in very easy reach of all that Key West has to offer. brbrWalking through the front door finds you in an open room design so prevalent in old Florida floor plans. Straight ahead is the living space. A ceiling fan and contemporary spotlights dot the ceiling. The area is appointed with a couch that can convert to a full bed. Two handsome and comfortable recliner chairs round out the seating. All are perfectly positioned for watching sports or movies or whatever suits your taste on the large flat screen TV. Of course there’s A.C., high speed internet, and cable TV to make you feel right at home. A flax-colored sisal area rug over the darker hardwood floors delineates the space nicely.brbrIn the flow of things, a rectangular dining table is located to the right and can serve many purposes. Four can sit here comfortably to eat a meal or to play a round of Key West Monopoly. Or maybe sometimes it becomes a workspace for writing or checking email.brbrThe kitchen is next. The dark wood floor and extended blue tile back splash anchor the space visually. Cabinets above and below provide space for all the kitchen accoutrements and appliances you would need to make a cup of coffee, to warm leftovers from dinner out the night before, or to prepare a three-course meal. Here also is a cabinet for the all-in -one washer/dryer topped with blond hard wood matching and extending the kitchen counter workspace. Refrigerator, cook-top stove, microwave, dishwasher are all arranged ergonomically in a U shape. Behind a louvered door is a closet for cleaning supplies. brbrStraight through from here you can see out French doors to the back balcony. But before you get that far, there’s a glass-top table and two chairs just perfect for a morning coffee and a delicious croissant from Frenchie’s Café just a few blocks down the street. The doors open onto a private balcony overlooking a spacious and gleaming pool and spa. The whole back area oasis is ringed by green palms that provide beauty and privacy for the exclusive use of the four units in the building. An ample brick deck surrounds the pool and provides chaise loungers and chairs for your comfort when you decide you are finished swimming or floating leisurely. Or maybe it’s time to return to your second-floor balcony where there’s a table, two chairs and a market umbrella that provides shade and distinction. It’s the perfect place for morning coffee or evening cocktails or for reading that novel you brought along.brbrBack inside is the bedroom and full bath. You’ll be happy to find the bed is a very comfy queen as you sink into it at night. Two small bedside tables with drawers hold lamps and leave a space for your cell phone. The room has plenty of windows for light or you can close the venetian blinds for darkness. A chest of drawers and a closet create plenty of put-away room for your hanging things or your foldable things. Adjacent is the full bath with shower and tub. Here again is a window that gracefully brightens the whole space.brbrBesides being a perfect vacation residence, the location is only blocks off the famous/infamous Duval Street. Closest to Upper Duval or what is known as “Uptown,” this end of Duval runs toward the Atlantic and has a reputation for being quieter and more relaxed than Lower Duval. Upper Duval boasts of multiple beaches such as Dog Beach, Higgs Beach, Reach Beach, and Smathers Beach. But of course, it has its bars and restaurants too. Most prominently Louie’s Back Yard, Dorada at Casa Marina, and Salute! On The Beach.brbrThe whole fourteen blocks of Duval, upper and lower, provide access to food, drink, tours, museums, galleries, and shopping. Cultural activities such as live music, art exhibitions, and plays are also plentiful. Perhaps let a butterfly land on your shoulder at Key West Butterfly and Nature Conservatory or catch a movie on one of the three screens at the locally run Tropic Cinema. Then stop in at Books & Books to catch a glimpse of the author Judy Blume stocking the shelves. And don’t forget to set your watch for sunset so you don’t miss the world-famous sunset party at Mallory Square at the Gulf end or lower end of Duval.brbrCredit Card Surcharge Notice: The owner of this unit asks guests to cover the processing fees for credit card payments. If you’d like to avoid the 3% surcharge, please reach out to our office to make your reservation and arrange payment by check. brbrThe Property may only be used for residential accommodations. No special events, parties, or functions of any kind are permitted on the Property. If this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We do not guarantee that the information VRBO (and affiliated sites) obtains from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.brbr**For Pet Friendly (dog) homes there are restrictions that include, but may not be limited to, the following: pet friendly means dogs, no other animal is permitted. Dogs are restricted to one (1) large dog or two (2) small dogs per stay. Due to Homeowner Insurance restrictions we are unable to accommodate the following breeds: Pit Bull Terriers, Staffordshire Terriers, Rottweilers, German Shepherds, Presa Canarios, Chows Chows, Doberman Pinschers, Akitas, Wolf-hybrids, Mastiffs, Cane Corsos, Great Danes, Alaskan Malamutes, Siberian Huskies nor any mixed breed that contain one of the preceding as part of that mix. Guest is responsible for an additional pet fee of $200.

Bed

Bath

Sleeps

$370.96

/ Nightly

Condo

Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today

Key West, Florida, United States

Pool & Jacuzzi Resurfacing NoticebrbrPlease be advised that the pool and jacuzzi area will be closed for resurfacing beginning:brJuly 6th – August 30th (weather permitting)brbrThe entire pool and jacuzzi area will be fully closed off during this time to allow the contractor to safely complete the work.brThis project is part of our ongoing efforts to maintain and improve our community amenities for everyone’s enjoyment.brbrbrOceanfront Oasis – 2BR/2BA Condo with Balcony Views at La Brisa brbrWelcome to your perfect tropical getaway! This beautifully appointed 2-bedroom, 2-bathroom condominium on the 3rd floor of the East Building at La Brisa offers sweeping ocean views and all the comforts of home—plus resort-style amenities.br Comfortable & Flexible Sleeping Arrangements:brbr Primary Bedroom: King bed, en suite bathroom, and direct balcony access.brbr Guest Bedroom: Two twin beds (convertible to a king).br Living Room: Queen-sized sleeper sofa—perfect for extra guests.br brFully Equipped Kitchen:brbrWhip up your favorite meals with ease. The kitchen features:brbr Keurig & drip coffee makersbr Crock-potbr Full cookware and utensilsbrbrRelax & Recharge:brbr Spacious balcony for sunrise views and ocean breezesbr Tile flooring throughoutbr Washer & dryer in-unit for conveniencebr Cable TV & high-speed Wi-FibrbrResort-Style Amenities at La Brisa:brbr Heated swimming pool & hot tubbr Sauna for ultimate relaxationbr Hard tennis courtbr Direct access to walking & biking trails along Smather’s BeachbrbrWhether you're here to unwind or explore, this condo is the ideal blend of comfort, location, and style. Your Oceanfront Oasis awaits!

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Bath

Sleeps

$227.68

/ Nightly

Condo

SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool!

Key West, Florida, United States

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCOMFORT AND VALUE IN TRUMAN ANNEX…brThis two bedroom first floor condominium is located in The Shipyard, a neighborhood of the coveted Truman Annex in the heart of Old Town Key West! Enjoy this comfortable ground floor front porch to sit and take in the passersby in true Key West fashion while you sip your coffee or relax with a glass of wine. With a preferred location and in exceptional condition, this little gem has a remodeled kitchen and bathroom and is located on the ground floor for your convenience. Throw your cares to the wind as you unwind in this charming, tree-shrouded neighborhood with walking paths and lanes. You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! The Shipyard also offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brComfort and functionality greet you as you enter this delightful abode. The fully equipped kitchen has everything you need to create a delicious meal for your loved ones, with a full size refrigerator, dishwasher, microwave, oven/stove and mini island. Gather around the dining table for 4 and then curl up on the couch in the adjacent living area to watch your favorite shows and movies. brbrSLEEPING ARRANGEMENTS…brUnwind from your day of island fun in one of the two comfy bedrooms. There is a twin bedroom that can be converted to a king if desired and a second room with a queen bed. Both rooms offer a clothing dresser, small flat screen tv and storage/hanging closets. Enjoy a shared hallway bathroom with a large glass-door shower and a washer/dryer closet adjacent to it.brbrOUTDOOR LIVING…brOpen the French door to the fenced private patio, inviting sultry breezes and Key West sunshine inside. This wonderful extension to the living space has a table for four where you can have your morning coffee or enjoy a cocktail after a long day of exploring. Fire up the grill and cook your fresh catch of the day!brbrPARKING...brThis home does offer parking for one vehicle (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community.brbrPETS...brThis is not a pet friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet 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 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrCOME STAY A WHILE...

2

Bed

1

Bath

4

Sleeps

$216.85

/ Nightly

Condo

Modern 2BR Condo Old Town/Balcony & Pool

Key West, Florida, United States

*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close to all the action & far enough away to enjoy a quiet getaway. Get comfortable in this clean & comfy home, which offers two private balconies, updated kitchen & modern bath. Desirable Southard Square is surrounded by tranquil tropical gardens & a heated 20x40 pool. Centrally located, this condo is 4 blocks from Duval St, Seaport Historic Pier & a short walk or bike ride anywhere on the island!

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Bath

Sleeps

$181.0

/ Nightly

Condo

A SEAGLASS PARADISE ~ Charming 2 BR/1 Ba 1st Floor Condo in Truman Annex!

Key West, Florida, United States

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCHARMING 1ST FLOOR CONDO IN BEAUTIFUL SHIPYARD COMMUNITY OF TRUMAN ANNEX…brThis adorable retreat with a community pool is located in the prestigious gated community of Truman Annex in Key West's famous Old Town neighborhood. With 2 bedrooms and 1 bath, it's cozy perfection for 2 couples or a small family. You will revel in the location which is only 2 blocks from the vibrant excitement of Duval Street and only 1/4 mile from the pristine beach of Fort Zachary Taylor State Park. You are walking distance to the island's hot spots: The Green Parrot, Sloppy Joe's, Hemingway's Home and Mallory Square - home of the famous nightly Sunset Celebration.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brYour southernmost serenity begins as you enter the sun-filled living area, a perfect space to unwind after an exciting day on the town. The fully appointed kitchen has been totally remodeled with new cabinets, and granite countertops and will inspire you to conjure up your favorite tropical dishes. Decompress and read your favorite novel on the comfortable furnishings or indulge in relaxed conversation over a crafted cocktail. Enjoy hardwood floors, and ceramic tile throughout the home. A washer and dryer are provided for your convenience.brbrSLEEPING ARRANGEMENTS…brSlip into tranquil slumber in one of the two bedrooms with plush queen beds. The living room also offers a sleeper sofa. The shared bathroom has a walk-in shower and single vanity. brbrOUTDOOR LIVING…brThe Shipyard in Truman Annex is a charming, tree-shrouded hideaway with serene walking paths and lanes. The beautiful community pool is lined with lounge chairs and is perfect for soaking up the Key West sun. This unit features a beautiful landscaped courtyard located next to the community pool.brbrPARKING...brThis home does offer parking for one vehicle, just steps from the front door - (vehicle cannot exceed 18 ft.). Oversized trucks and extra large SUVs are not permitted and will have to park outside of this community. brbrPETS...brThis is a dog friendly home (no cats) with a required pet fee. Please include the size and breed when inquiring. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet 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. brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.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!brbrYOUR ESCAPE TO PARADISE IS CALLING...

2

Bed

1

Bath

4

Sleeps

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