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$2,060,000
5 Beds ⋅ 3 Baths ⋅ 620686 MLS
Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys, with SELLER FINANCING OFFERED! Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat. Featuring an adjacent oceanfront parcel with a private beach, kayaks, and a floating dock for fishing or docking boats up to 24 feet, this property provides everything needed for fun and relaxation. Outdoors, enjoy a sparkling swimming pool, soothing hot tub, tropical landscaping with coconut palms and banana trees, and a screened-in porch for al fresco dining. Inside, the open floor plan includes four king bedrooms and a fifth bedroom with a queen and single bed, smart TVs, and updated appliances. Centrally located at MM21.5, Fandango is just 20 minutes from Key West, 10 minutes from Big Pine Key, and 15 minutes from Bahia Honda State Park, with dining options nearby, including a 5-star restaurant within a mile. This property is offered fully furnished and equipped, including bookings into 2027 and 10-years' average income of $160+k. Professional property management is in place, ensuring both secure investment returns and worry-free family vacations. This low-maintenance, turn-key home offers the rare opportunity to own one of the few legally licensed short-term rentals in the Lower Keys. Owning a vacation rental property means you're not just paying for vacations--you're building equity and unlocking financial benefits, all while eliminating the scramble for accommodations every trip. Show up, relax, and let your investment work for you.

94 Sacarma Dr, Cudjoe
$449,999
1 Beds ⋅ 1 Baths ⋅ 620685 MLS
Ocean-View Waterfront Retreat in Gated Venture Out on Cudjoe Key. NIGHTLY RENTALS ALLOWED Enjoy the Florida Keys lifestyle in this well-maintained 1-bedroom, 1-bathroom waterfront home located in the highly desirable gated community of Venture Out. With ocean views, direct boating access, excellent amenities, and nightly rentals permitted, this property is ideal as a vacation home, income-producing investment, or full-time residence. The home features numerous updates, including a new roof in 2018, air-conditioning system in 2020, and hot water heater in 2025. Additional improvements include newer impact-resistant windows, Bahama shutters, powder-coated storm panels, and updated mobile home tie-downs for added peace of mind. Boaters will appreciate the 35-foot concrete seawall with dock whips and quick access to the backcountry, offshore waters, and Atlantic Ocean. A concrete slab beneath the home provides valuable storage for fishing gear, kayaks, bicycles, and other Keys essentials. Venture Out offers an impressive array of amenities, including a large oceanfront saltwater swimming pool, community marina with fuel station, boat ramp, and boat wash-down area. Residents and guests also enjoy lighted tennis and pickleball courts, basketball and bocce courts, a recreation hall, waterfront pavilion, and regular community activities. The golf-cart-friendly neighborhood makes it easy to enjoy everything the community has to offer. Whether you are searching for a relaxing island escape, strong rental opportunity, or waterfront home in the Lower Keys, this property delivers an exceptional combination of location, boating access, amenities, and investment potential. Schedule your private showing today and experience this special Cudjoe Key property for yourself.

701 Spanish Main Dr Unit 246, Cudjoe
$2,800,000
4 Beds ⋅ 3 Baths ⋅ 619615 MLS
SPECIAL DAILY TRANSIENT LICENSE!!! Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers the scale, privacy, and setting luxury buyers search for but rarely find. From the moment you enter, the home is designed around the water. Expansive living areas, soaring ceilings, and oversized windows frame endless blue views while natural light fills the interior. The spacious layout offers multiple entertaining zones, generous bedroom suites, and the kind of footprint that allows a buyer to enjoy immediately or elevate into a signature Keys showplace. Outside is where this property separates itself from nearly everything else on the market. The massive parcel creates room to breathe, entertain, and enjoy waterfront living on a level almost impossible to replicate today. A private pool, sandy beach area, dockage, mature tropical grounds, and open-water backdrop combine to create a true resort atmosphere. Sunrise coffee, sunset cocktails, paddleboarding, boating, and stargazing all happen from your own backyard. Under the home, an immense garage / storage / workshop space offers rare functionality for collectors, boating gear, vehicles, trailers, hobbies, or business use. Very few waterfront homes in the Keys offer this level of usable enclosed space. For investors, this property's transient rental license potential is a major value driver. Large open-water estates with acreage and premium amenities command exceptional demand in the vacation market. With the right presentation and management plan, this is the type of asset that can serve as both a personal retreat and a high-performing income property. Lets take a look!!!

21640 Overseas Hwy, Cudjoe
$3,099,000
4 Beds ⋅ 3 Baths ⋅ 619589 MLS
Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with 235' of waterfront this home is designed with life on the water in mind. Featuring two boat lifts, 15,000 lb and 12,000 lb, providing flexibility for multiple vessels along with a 2-car Garage for additional storage for all of your gear. Inside, the spacious 3 Bedroom, 3 Bath 3,056 sq. ft. home comfort and style blend with ease. The kitchen stands out with 6-burner Viking Range, Viking dishwasher, cabinet-front refrigerator, stainless appliances, pantry and generous space for entertaining, flowing seamlessly into the main living areas. Soaring ceilings fills the home, creating a bright and inviting atmosphere throughout. Upstairs a loft-style office and a dedicated theatre room offering a bar with beverage center provides the perfect setting for movie nights or game-day gatherings. The primary suite serves as a private retreat, complete with a lavish bath with bidet, separate shower and a relaxing jet tub, ideal for unwinding at the end of the day. Porches on both sides of the home overlook the canals and lead to a unique sandy point at the corner, offering a peaceful setting to take in water views and stunning sunset skies. After a day on the water relax by your waterfront heated salt pool or enjoy sipping cocktails on the screened lanai. Additional amenities include impact windows and doors, whole house generator and ice machine. Cudjoe Gardens is an upscale waterfront community known for its ground-level concrete homes thoughtfully built above the floodplain. The neighborhood is home to Cudjoe Gardens Marina, a convenient full-service stop for fuel, bait, and refreshments on your way to world-class fishing and diving. Residents also enjoy The Bent Prop, a beloved waterfront restaurant offering a true taste of the Keys lifestyle.

21090 5th Ave, Cudjoe
$595,000
2 Beds ⋅ 2 Baths ⋅ 618979 MLS
Owner says ''Bring All Offers'' Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed. Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a cozy and inviting interior, complete with all the essentials for a seamless transition. The open-concept living area flows effortlessly, providing a warm atmosphere for gatherings or quiet evenings. Outside, you'll find a concrete seawall, perfect for fishing enthusiasts and water lovers alike. The included fish cleaning station makes it easy to prepare your catch right at home. With ample outdoor storage space underneath the house, you'll have plenty of room for kayaks, fishing gear, or seasonal decorations. Located in a prime area that allows for nightly rentals, this property is not only a fantastic home but also a lucrative investment opportunity. Whether you're looking to enjoy your own slice of paradise or generate rental income, this home has it all. Don't miss your chance to own this charming coastal retreat. As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the marina store and fuel station. Sports enthusiasts will love the two lighted tennis courts, pickleball, basketball, and bocce courts. The recreation hall and community pavilion host a variety of activities and events, making it easy to connect with neighbors and make new friends. This golf cart-friendly community also features a boat ramp, giving you direct access to the stunning waters of the Florida Keys. Whether you're looking for a vacation home, rental investment, or a permanent paradise, this property has it all!

701 Spanish Main Dr Unit 604, Cudjoe
$535,000
2 Beds ⋅ 2 Baths ⋅ 617289 MLS
Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day on the water. A resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area with tiki huts and more! Cruise around the property in your golf cart to the community store or to join in on the numerous community activities. Live with peace of mind in an exclusive gated community which adds a sense of security and prestige. This home is ready for you to move in and enjoy! Don't miss this rare opportunity to own a piece of paradise! Nightly Rentals Allowed! Plenty of potential for rental income.

701 Spanish Main Dr Unit 247, Cudjoe
$2,795,000
4 Beds ⋅ 3 Baths ⋅ 618526 MLS
Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully arranged for relaxed living and effortless entertaining. Recent renovations elevate the home even further, with the kitchen and primary bath completely and tastefully reimagined by D'Asign Source. The stunning chef's kitchen now features Omega cabinetry, elegant quartzite stone surfaces, premium KitchenAid appliances, and a striking black walnut round dining table that anchors the space with warmth and natural beauty—perfect for gathering with family and friends. Pocket sliding doors open the living areas to a spacious screened Florida Room (approx. 494 sq. ft.), seamlessly blending indoor and outdoor living. Outside, enjoy mature tropical landscaping, extensive paved driveways and walkways, and resort-style spaces designed for relaxing and entertaining. For boating enthusiasts, this property truly shines: approx. 4' control depth, quick access to the reef and backcountry, protected canals, and proximity to a full-service marina. The seawall is fully equipped with a cut-in boat slip, 15,000 lb. boat lift, davits, swim ladder, and outdoor shower—everything you need for life on the water. Additional highlights include a barrel tile roof, an attached 2 car garage, a versatile 676 sq. ft. garage space ideal for storage, hobbies, or island toys. Whether you're hosting sunset gatherings by the pool, heading out for a day on the water, or simply unwinding in your own tropical retreat, this remarkable property offers the perfect blend of comfort, style, and true Florida Keys lifestyle. Come see this exceptional canal-front retreat, where every day feels like a getaway.

20920 5th Ave, Cudjoe