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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.

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

$5,750,000

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor. 5 (2 bedroom one bath cottages) and one (3 bedroom 2 bath house), 6 water meters, 6 electric meters. Heated salt water pool. The property is also listed with 9 additional units MLS #612522.

13 Beds ⋅ 7 Baths ⋅ 620213 MLS

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor. 5 (2 bedroom one bath cottages) and one (3 bedroom 2 bath house), 6 water meters, 6 electric meters. Heated salt water pool. The property is also listed with 9 additional units MLS #612522.

21470 Overseas Hwy, Cudjoe

$235,000

This 24 point offshore lot has been evaluated by Monroe County and is eligible for dedication back to Monroe County so you can use those 24 points to add to your ROGO points to assist in receiving a building permit through the ROGO system.

620165 MLS

This 24 point offshore lot has been evaluated by Monroe County and is eligible for dedication back to Monroe County so you can use those 24 points to add to your ROGO points to assist in receiving a building permit through the ROGO system.

Lot 7 Parcel 10, Cudjoe

$2,800,000

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!!!

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

$1,725,000

Oceanfront living on Cudjoe Key, where broad covered balconies, generous outdoor space, and a private boat launch put Keys waterfront life within reach. This four-bedroom, three-bath home is a study in coastal architecture -- large impact glass doors and windows frame open water views and pull natural light into every room. Soaring 26' ceilings and rich wood beams anchor the open-concept main level, which includes a renovated kitchen, dining space, living room, laundry, and two bedrooms with two full baths. Upstairs, a third bedroom sits at the top of the stairs, and a catwalk leads to the fourth bedroom with ensuite bath and a walkout deck framing panoramic open water views. The home has been restored to its former glory with modern updates layered in -- rustic accents meet open, light-filled spaces that let the oceanfront setting do the talking. Adjacent lot also available for even more ocean enjoyment. Seller financing available: 50% down, 6% for 15 years, no flood or wind insurance required. This home needs to be seen to be fully appreciated. Schedule your showing today.

4 Beds ⋅ 3 Baths ⋅ 619558 MLS

Oceanfront living on Cudjoe Key, where broad covered balconies, generous outdoor space, and a private boat launch put Keys waterfront life within reach. This four-bedroom, three-bath home is a study in coastal architecture -- large impact glass doors and windows frame open water views and pull natural light into every room. Soaring 26' ceilings and rich wood beams anchor the open-concept main level, which includes a renovated kitchen, dining space, living room, laundry, and two bedrooms with two full baths. Upstairs, a third bedroom sits at the top of the stairs, and a catwalk leads to the fourth bedroom with ensuite bath and a walkout deck framing panoramic open water views. The home has been restored to its former glory with modern updates layered in -- rustic accents meet open, light-filled spaces that let the oceanfront setting do the talking. Adjacent lot also available for even more ocean enjoyment. Seller financing available: 50% down, 6% for 15 years, no flood or wind insurance required. This home needs to be seen to be fully appreciated. Schedule your showing today.

22542 Jolly Roger Dr, Cudjoe

$499,000

Oceanfront lot in the Lower Keys overlooking Cudjoe Bay. Build your dream with expansive open-water views and ocean breezes. Prime waterfront setting with incredible potential. No current building permit; buyer to verify process and timelines. Rare opportunity to own a slice of paradise.

619557 MLS

Oceanfront lot in the Lower Keys overlooking Cudjoe Bay. Build your dream with expansive open-water views and ocean breezes. Prime waterfront setting with incredible potential. No current building permit; buyer to verify process and timelines. Rare opportunity to own a slice of paradise.

22552 Jolly Roger Dr, Cudjoe

$5,750,000

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor The property is also listed with 9 additional units MLS #612522.

13 Beds ⋅ 7 Baths ⋅ 618705 MLS

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor The property is also listed with 9 additional units MLS #612522.

21470 Overseas Hwy, Cudjoe

$879,000

This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side is fully equipped with six heavy duty dock posts and cleats, ideal for boating, fishing, and easy water access. This beautifully maintained home features two bedrooms and two full bathrooms, with tile flooring throughout, a metal roof, central air conditioning and abundant storage. The bright, open interior is surrounded by windows galore in the living area, perfectly framing the stunning outdoor scenery and flooding the home with natural light. The primary bedroom opens directly to a large covered porch, where you can wake up to breathtaking sunrises over the Atlantic. Outside, enjoy a spacious patio perfect for evening gatherings, moonrises and watching the incredible sealife. Additional features include accordion shutters and a full line of appliances, making this home as functional as it is beautiful. Located in Venture Out on Cudjoe Key, a private and gated community. Residents enjoy 24 hr gated security and patrol, two pets allowed and transient rentals permitted. The community amenities are unmatched and include: Oceanfront heated saltwater pool, hot tub, marina with ship store, fuel dock, two boat ramps, two tennis courts, two pickleball courts, basketball, bocce ball and playground for the kids. This is a rare opportunity to find your happy place in paradise. Seller says bring offers

2 Beds ⋅ 2 Baths ⋅ 618239 MLS

This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side is fully equipped with six heavy duty dock posts and cleats, ideal for boating, fishing, and easy water access. This beautifully maintained home features two bedrooms and two full bathrooms, with tile flooring throughout, a metal roof, central air conditioning and abundant storage. The bright, open interior is surrounded by windows galore in the living area, perfectly framing the stunning outdoor scenery and flooding the home with natural light. The primary bedroom opens directly to a large covered porch, where you can wake up to breathtaking sunrises over the Atlantic. Outside, enjoy a spacious patio perfect for evening gatherings, moonrises and watching the incredible sealife. Additional features include accordion shutters and a full line of appliances, making this home as functional as it is beautiful. Located in Venture Out on Cudjoe Key, a private and gated community. Residents enjoy 24 hr gated security and patrol, two pets allowed and transient rentals permitted. The community amenities are unmatched and include: Oceanfront heated saltwater pool, hot tub, marina with ship store, fuel dock, two boat ramps, two tennis courts, two pickleball courts, basketball, bocce ball and playground for the kids. This is a rare opportunity to find your happy place in paradise. Seller says bring offers

701 Spanish Main Dr Unit 265, Cudjoe

$1,399,000

Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you to your deeded dock equipped with water and electric, giving you effortless ocean access just steps from your door. The interior is light, open, and welcoming, with a focus on bringing the outside in. Enjoy a wraparound porch that frames panoramic views of the Atlantic, while inside you'll find an open floor plan with tile floors and island-inspired charm throughout. The entire second level is dedicated to a spacious primary suite, complete with a cozy sitting area overlooking the sea. Cudjoe Cove offers low HOA dues, a resort-style pool with waterfall, and trailer storage. Just 20 minutes from Key West and moments from restaurants, a marina, and conveniences — this home is ideal as a full-time residence, a second home, or a vacation getaway.

3 Beds ⋅ 2 Baths ⋅ 618382 MLS

Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you to your deeded dock equipped with water and electric, giving you effortless ocean access just steps from your door. The interior is light, open, and welcoming, with a focus on bringing the outside in. Enjoy a wraparound porch that frames panoramic views of the Atlantic, while inside you'll find an open floor plan with tile floors and island-inspired charm throughout. The entire second level is dedicated to a spacious primary suite, complete with a cozy sitting area overlooking the sea. Cudjoe Cove offers low HOA dues, a resort-style pool with waterfall, and trailer storage. Just 20 minutes from Key West and moments from restaurants, a marina, and conveniences — this home is ideal as a full-time residence, a second home, or a vacation getaway.

21250 Conch Dr, Cudjoe

$12,999,999

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment

31 Beds ⋅ 19 Baths ⋅ 610484 MLS

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment

21540 21470 Overseas Hwy, Cudjoe

$12,999,999

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions) over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Excellent rental history, shared coin laundry, 2 swimming pools. 2 parcels on US 1 are zoned Sub Urban Commercial, 3 private driveways. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment. Seller is licensed Realtor

31 Beds ⋅ 19 Baths ⋅ 612522 MLS

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions) over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Excellent rental history, shared coin laundry, 2 swimming pools. 2 parcels on US 1 are zoned Sub Urban Commercial, 3 private driveways. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment. Seller is licensed Realtor

21540 21470 Overseas Hwy, Cudjoe