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.


Properties Available 12 properties available
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 Monthly Rental
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 Pet Friendly
$255.00 - $949.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (6)
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 Pet Friendly
$3,500.00 - $6,553.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (6)
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
Hot HOT 28
Monthly Rental Monthly Rental
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)
Blue Horizon
Private Home Pet Friendly
$295.00 - $1,011.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (1)
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
Hot HOT 25
Tidewater Views
Cottage Pet Friendly
$200.00 - $741.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (309)
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 Monthly Rental
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)
Mariner's Hidden Haven
Private Home Pet Friendly
$175.00 - $551.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (4)
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 - $971.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (48)
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 Monthly Rental
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)
Carefree on Cudjoe
Private Home Pet Friendly
$265.00 - $894.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating Rating Rating Rating Rating 5 (3)
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 - $994.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (113)
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
Monthly Rental Monthly Rental
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)
Azure Daydream
Private Home Pet Friendly
$200.00 - $799.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (2)
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
Hot HOT 34
Keysie Does It
Private Home
$215.00 - $809.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (40)
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
Hot HOT 34
Turtle Cove Views
Cottage Pet Friendly
$222.00 - $712.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (151)
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 Monthly Rental
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)
Infinite Horizons
Private Home Pet Friendly
$517.00 - $1,152.00 / per night
Bedrooms 6 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (1)

Tell us what you're looking for and someone will contact you with available options.

I agree

Frequently Asked Questions

What part of the Florida Keys is considered the Lower Keys?

The Lower Keys stretch from just past Marathon to Key West, including islands like Big Pine Key, Cudjoe Key, Sugarloaf Key, and Summerland Key. These islands offer a more peaceful atmosphere compared to the Upper Keys and Key West.

Are Lower Keys vacation rentals close to the beach?

Many vacation rentals in the Lower Keys are near the water, with some offering direct beach access or waterfront views. Popular beach spots nearby include Bahia Honda State Park and the shoreline around Big Pine Key.

Is it better to stay in the Lower Keys or Key West?

The Lower Keys are a great choice for visitors looking for a quiet, nature‑focused experience with easy access to boating, snorkeling, and fishing. Key West is more lively and crowded, while the Lower Keys offer a slower pace and more space to relax.

Can I rent a vacation home in the Lower Keys with a boat dock?

Yes, several vacation homes in the Lower Keys include private docks or canal access. These are perfect for guests bringing boats or looking to rent one during their stay.

What activities are popular in the Lower Keys?

Guests enjoy snorkeling at Looe Key Reef, kayaking through mangroves, fishing in the backcountry, and visiting wildlife areas like the National Key Deer Refuge on Big Pine Key.

Are pets allowed in Lower Keys vacation rentals?

Some properties do allow pets, though it depends on the individual home. Be sure to check each listing for pet policies or contact the rental team for help finding a pet‑friendly option.

//