Islamorada, FL Homes for Sale under $300,000

Move-in ready townhouse located in the heart of Islamorada! This 2-bedroom, 1.5-bath home has been well maintained and features impact windows and doors, fresh interior paint, a metal roof in 2024, newer AC, upgraded electrical throughout and a washer and dryer in the unit. The galley kitchen provides ample cabinet space, induction stove top, dishwasher and pantry. Enjoy convenient access to the

Sharon Kelly-Brown Sharon J. Kelly Realty, Inc.

6+ Month/Annual-- Rental--Beautiful Double Waterfront Lot in Prestigious Plantation Key Colony. This stunning 4-bedroom, 2-bath waterfront home sits on a Rare Double Lot with a Private Boat Ramp & Boat lift. Step outside to your Private Oasis complete with a Private Tiki hut - Gorgeous secluded in-ground Pool and Cabana Hut Bungalow - The open-concept kitchen features Granite countertops and

Tracey Petrusha Venture Realty Group

Escape to the Florida Keys and enjoy Bay Views, brilliant Sunsets, and effortless Boating Access from this stunning 3-bedroom, 2.5-bath canal-front home — just one lot from Florida Bay. Designed for island living, the first level offers a spacious screened waterside patio perfect for entertaining or relaxing. Watch the game on the big-screen TV, cook in the outdoor kitchen, or unwind by the water

Terri Bodker Ocean Bay Realty of the Keys

The perfect spot to call home. Plantation Villas unit G101 is a ground-level end unit in the quiet back corner of the community. This one-bedroom, one-bath home has been updated this past year with a new kitchen featuring all new appliances, Quartz stone countertops, under-cabinet LED lighting, and LED ceiling lights. The bathroom features a tile shower and a built-in Bluetooth music speaker.

Steven Conley Compass Florida LLC - Tavernier

Turnkey, located in Plantation Key Colony, 2 bedrooms/ 1.5 bathrooms upstairs. Wrap around and screened porch, fully fenced backyard, open floor plan, preferable upgrades throughout including ss appliances, all in one combo unit washer and dryer. Access to HOA Boat Ramp and Park. Walking distance to schools, stores, and restaurants. No Pets, Utilities included, Furnished. F/L/S

The Jude Lindback Te Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

Charming Waterfront Home in Tavernier - Old Keys Style Living! Discover the beauty of waterfront living in this charming ground-level concrete home in Tavernier. Featuring two bedrooms, one bathroom, and an open living floor plan, this home offers comfort and convenience in a serene setting. Enjoy breathtaking bay views from the expansive screened porch and huge back yard, perfect for relaxing

Lisa Frins Century 21 Prestige Realty Grp, Tavernier

LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY ON MILLIONAIRES' ROW IN PLANTATION BY THE SEA! LOCATED ON PLANTATION KEY/ISLAMORADA IN THE BEAUTIFUL FLORIDA KEYS! TURN KEY STUNNING AND REMODELED, FULLY FURNISHED 2 BEDROOM 1.5 BATH CONDO IS MOVE IN READY! ALL YOU NEED ARE YOUR CLOTHES AND TOOTHBRUSH! GLASSWARE, STEMWARE, SHEETS, TOWELS, ALL ARE FURNISHED FOR YOU! BEAUTIFUL OPEN CONCEPT

Anthony Garcia The Keyes Company

Furnished 3 Bed / 2 Bath - All Utilities IncludedBeautifully furnished upper-level unit featuring 3 bedrooms and 2 bathrooms. Rent includes utilities, cable, lawn care, and pool service for a truly hassle-free living experience. Located in a quiet neighborhood close to restaurants, shopping, and top-rated schools.Interested in more space? The entire house (6 Bed / 4 Bath) is also

Tracey Petrusha Venture Realty Group

Nice and quiet 1/1 located in the desirable Plantation Villas on Plantation Key. This is a upper corner unit with Tile throughout. Impact Cat 5 hurricane windows and newer AC. Tub shower combination in bath. Large walk-in closet in bedroom with lots of storage and ceiling fans throughout. Beautiful Yard area for outdoor enjoyment. This development has a pool, clubhouse and picnic area. Located

Sharon Kelly-Brown Sharon J. Kelly Realty, Inc.

2 Bedroom, 2 Bath Townhome for Rent Enjoy resort-style living in this beautifully maintained 2-bedroom, 2-bath townhome featuring an array of desirable community amenities. Residents have access to a sparkling pool, private beach area, tennis courts, BBQ facilities, and a welcoming clubhouse. Conveniently located near top-rated schools, shopping, Founders Park, and the local hospital, this home

Lizette Miller Coldwell Banker Schmitt Islamorada

***Available starting November 15, 2026. *** Experience elevated living in this fully furnished, luxury studio 1/1 apartment located at Mile Marker 91.5 Oceanside in Tavernier. Recently renovated from top to bottom, this turnkey residence features designer furnishings, modern appliances, and premium finishes throughout. Ideally positioned in the heart of the Upper Keys, the property offers

Kevin Cornell Cornell Commercial Real Estate, Inc.

Two-story waterfront home located on a canal with direct access to the bay. Ideal for boating enthusiasts, this property offers a functional layout, great natural light, and beautiful water views. Enjoy easy access to open water from your backyard, perfect for fishing, kayaking, or relaxing by the canal. Great opportunity for full-time living or a vacation home in the Florida Keys.

Adriana Alvarez A.M.A. Realty Group Inc.

Welcome to this mobile home in Tavernier! This cozy 2-bedroom, 1-bathroom mobile home offers the perfect blend of affordability and location. Nestled in a prime spot close to the beach, boat ramps, picnic areas, and ball fields. Tavernier is known for its picturesque surroundings, friendly community, and easy access to local amenities, shops, and dining options.

Lisa Frins Century 21 Prestige Realty Grp, Tavernier

Experience the ultimate Florida Keys retreat at Pickle Ball Estate, a stunning new luxury rental in the heart of Islamorada, thoughtfully crafted by 4 Keys Construction. This brand-new four-bedroom, five-bathroom residence combines sophisticated coastal design with exceptional amenities, creating the perfect escape for extended stays and seasonal living.Designed for both relaxation and

Alexander Pinero Pine River Realty, LLC

3 Bedroom 2 bathroom updated home walking distance to Harry Harris park. Centrally located in Tavernier and close to schools, shopping, and other great amenities Tavernier has to offer. Pets are welcome with owner approval and pet deposit. Utilities are not included. Unfurnished. Available immediately.

Kenneth Smith American Caribbean Real Estate, Christie's International Real Estate

Waterfront Canal Home located in the Best Islamorada Plantation key Location.COMPLETELY FURNISHED TURNKEY HOME. Large bedrooms with King Beds. Metal Roof , Smart TVs, Quartz countertops , open kitchen , Modern bathrooms, Great living room with open kitchen, Washer & Dryer, Screened in wrap around porch overlooking the water. 60 ' of Canal Frontage. HUGE enclosed Garage area underneath , New

Jonathan Minerick Homecoin.com

LONG TERM RENTAL OPPORTUNITY!Ground-level living in the heart of Islamorada! Situated on an oversized parcel, this beautifully completely remodeled 2-bedroom, 2-bath home offers comfort and an unbeatable location. The tastefully updated interior includes porcelain tile throughout the home including showers, quartz countertops and brand new LG appliances and offers an open living area and

Lisa Frins Century 21 Prestige Realty Grp, Tavernier

Experience elevated living in this fully furnished 1 bedroom / 1 bathroom luxury apartment located at Mile Marker 91.5 Oceanside in Tavernier. Recently renovated from top to bottom, this turnkey residence features designer furnishings, modern appliances, and premium finishes throughout. Ideally positioned in the heart of the Upper Keys, the property offers unmatched convenience with restaurants,

Kevin Cornell Cornell Commercial Real Estate, Inc.

LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY ON MILLIONAIRES' ROW IN PLANTATION BY THE SEA! LOCATED ON PLANTATION KEY/ISLAMORADA IN THE BEAUTIFUL FLORIDA KEYS! TURN KEY STUNNING AND REMODELED, FULLY FURNISHED 2 BEDROOM 1.5 BATH CONDO IS MOVE IN READY! ALL YOU NEED ARE YOUR CLOTHES AND TOOTHBRUSH! GLASSWARE, STEMWARE, SHEETS, TOWELS, ALL ARE FURNISHED FOR YOU! BEAUTIFUL OPEN CONCEPT

Anthony Garcia The Keyes Company

Breathtaking Bayfront Retreat in Hammer Point! Experience waterfront living at its finest in this stunning canal-front home with direct bay and ocean access. Located in the desirable Hammer Point community, you'll enjoy postcard-worthy sunsets and a relaxed island vibe. This beautifully renovated residence offers 3 bedrooms and 2 bathrooms upstairs plus a legal 1/1 guest suite downstairs. The

Claudette Mell Ocean Sotheby's International Realty

Newly built (2024) home located at Mile Marker 90 on Plantation Key available May 1st for annual rental! Located directly across from the community boat ramp with 72 hour dockage and direct access to both the Bay and Ocean via Tavernier Creek. Offering a total of 4 bedrooms and 3 bathrooms, this home provides beautifully appointed fixtures and finishes throughout and ample space for comfortable

Natalie Bevis Berkshire Hathaway HomeServices Keys Real Estate - Islamorada