Lower Keys Vacation Rentals – Homes in Big Pine, Sugarloaf, and More

Escape the crowds and discover the relaxed pace of the Lower Florida Keys. From Big Pine Key to Sugarloaf Key, this island chain offers a quiet, laid-back experience that feels miles away from the rush of Key West. Our Lower Keys vacation rentals provide the ideal setting for travelers looking for peace, natural beauty, and easy access to the water.

Whether planning a fishing trip, a romantic getaway, or a family gathering, these rentals bring you closer to what makes the Keys special. Stay near scenic beaches, wildlife refuges, and some of the best boating spots in the region. Many of our homes include private docks, pools, and open-water views—perfect for watching the sun melt into the horizon.

Snorkel the Looe Key Reef, kayak through mangrove tunnels, or eat at a nearby seafood shack. Every island in the Lower Keys has its charm, and staying in one of our vacation homes gives you the space and comfort to take it all in.

All of our Lower Keys vacation rentals come with the full support of our local team. Whether you need help finding the right home or tips on what to do nearby, we're here to make your stay easy and memorable. Ready to experience the quieter side of the Florida Keys?

Please browse our selection of Lower Keys vacation rentals and find your perfect island hideaway today.

12 properties available

TIDEWATER VIEWS is a cozy 820 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out, a residential community with a heated 80-foot pool with large Jacuzzi and Kiddie Pool, tennis courts

Tidewater Views

Cottage

$200^.00 - $788^.00 / per night

The vacation opportunity of a lifetime awaits at CASSIE’S PARADISE. A secluded oceanfront experience, this breathtaking home sits on over half an acre and is less than 20 miles from Key West. The 4,300 sq ft interior affords your group plenty of room to spread out. The real showstopper of this home is the backyard - complete with 120 feet of privat

Cassie's Paradise

Estate

$3,800^.00 - $6,888^.00 / per night

Formerly known as Playland in Paradise, the ultimate Keys vacation awaits you at BAYPOINT OASIS! This spacious waterfront property is perfect for large groups, featuring an open floor plan, six bedrooms, including three master suites, and expansive outdoor space. BAYPOINT OASIS offers every amenity you could ask for in a vacation home… and then som

Monthly Rental

A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)

Baypoint Oasis

Private Home

$255^.00 - $964^.00 / per night

What could be better than spending your tropical vacation in a newly built waterfront home that offers spectacular views and easy access to the beautiful waters of the Florida Keys. POSTCARD POINT is an elevated 2 bedroom home that allows you to enjoy the luxury of brand-new construction in the waterfront location you've been searching for. Picture

Postcard Point

Private Home

$244^.00 - $1,023^.00 / per night

AZURE DAYDREAM, a beautifully renovated waterfront home located 25 miles north of Key West, epitomizes Florida Keys living at its finest. From spending your days on the boat exploring the Lower Keys, to hosting the ultimate family game night in the game room, there’s no shortage of fun to be had at AZURE DAYDREAM. This 4-bedroom home was recently u

New Property

Fabulously Fresh New Property!!

Monthly Rental

Azure Daydream

Private Home

$200^.00 - $810^.00 / per night

From the moment you arrive to this spectacular Florida Keys home, you will feel all your stresses and worries simply melt away. CAREFREE ON CUDJOE is an expansive waterfront property that evokes the easy-going nature of Keys living and provides an ideal setting for those looking to enjoy a ‘carefree’ vacation. There will certainly not be a shortage

Monthly Rental

Carefree on Cudjoe

Private Home

$265^.00 - $910^.00 / per night

Life in the Florida Keys is all about spending time outdoors, indulging in the things you love with the ones you love; and BLUE HORIZON is the perfect vacation home to experience Keys living for yourself. Whether your ideal day is floating around the large pool with a cold drink in hand, cruising the waters of the Lower Keys in your boat, or gather

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Monthly Rental

Blue Horizon

Private Home

$295^.00 - $1,026^.00 / per night

Escape the “changing tides” of your day-to-day routine by spending a month in the Keys. MARINER’S HIDDEN HAVEN provides an ideal island setting for re-centering your compass by way of your own private waterfront retreat. Picture mornings sipping coffee on the dock, lazy days by the pool, and beautiful sunsets on your boat. The home’s open layout an

Monthly Rental

Mariner's Hidden Haven

Private Home

$175^.00 - $551^.00 / per night

Looking to make a big ‘splash’ for your next tropical vacation? MERMAID MAGIC is your answer! This newly built elevated 2 bedroom home offers incredible views and easy access to the beautiful waters of the Florida Keys. In addition, you’ll have access to the wonderful on-site amenities offered at Venture Out Resort: a heated 80-foot pool with large

Mermaid Magic

Private Home

$300^.00 - $1,058^.00 / per night

Does your fast-paced, day-to-day routine have you dreaming of a relaxing vacation in the Florida Keys? KEYSIE DOES IT will turn that dream into reality! This elevated home offers the modern conveniences of newer construction in a gated, waterfront community. In addition to the in-home amenities, you’ll have access to wonderful community amenities a

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Keysie Does It

Private Home

$215^.00 - $851^.00 / per night

As if a vacation to the Florida Keys wasn’t memorable enough, the million-dollar views from INFINITE HORIZONS are ones you’ll never forget. Located about 10 minutes north of Key West on Big Coppitt Key, INFINITE HORIZONS sits on an oversized, open water lot with a private pool and beach placed against the stunning backdrop of the gorgeous Gulf of M

Monthly Rental

Infinite Horizons

Private Home

$517^.00 - $1,169^.00 / per night

TURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of the Florida Keys and the home com

Turtle Cove Views

Cottage

$222^.00 - $757^.00 / per night

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