Florida Keys Vacation Rentals

Browse Florida Keys vacation rentals with Seven Keys Vacations and find a home base that fits the way you want to experience the islands. Our collection includes vacation homes, condo rentals, waterfront stays, private pool homes, pet-friendly rentals, boat dock homes, and longer stay options across Key West, Key Largo, Islamorada, Marathon, Big Pine Key, and the Lower Keys.

Every part of the Keys has its own rhythm. Stay in a Key West vacation rental for walkable dining, historic streets, nightlife, and sunset celebrations. Choose Key Largo vacation rentals for easy access to snorkeling, diving, and boating. Settle into Islamorada vacation rentals if fishing, marinas, and waterfront restaurants are high on the list. For a central island stay, browse Middle Keys vacation rentals near Marathon, or look to Lower Keys vacation rentals for a quieter, more laid-back escape.

Find the Right Florida Keys Rental for Your Trip

Planning a family vacation, fishing trip, couples getaway, remote work stay, or longer island escape? Use the filters to compare Florida Keys house rentals, Florida Keys condo rentals, ocean view rentals, pet-friendly homes, private pool rentals, and vacation rentals with boat docks. You can also narrow your search by travel dates, bedrooms, location, amenities, and stay length.

If you are staying for a full week or longer, our weekly rentals in the Florida Keys make it easier to settle in and enjoy the islands at a slower pace. Guests planning an extended winter stay, remote work trip, or seasonal getaway can also explore monthly rentals in the Florida Keys for more time on the water, more flexibility, and a little less suitcase chaos.

Browse available Florida Keys vacation rentals below and book direct with Seven Keys Vacations for a more personal, locally focused rental experience.

Florida Keys vacation rentals with turquoise water, palm trees, and waterfront scenery

Properties Available 224 properties available
Welcome to Your Private Slice of Paradise in the Florida Keys 🌴 Bayfront Sunset Oasis | Private Beach • Pool • Dock • Kayaks • Wildlife Encounters Escape to the ultimate coastal retreat at this spectacular four-bedroom Marathon estate, featuring an additional bunk room off the master suite, and front-row access to the natural w
7-night minimum 7-night minimum
Oceanfront
- Marathon
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
Dog Friendly Dog Friendly
This spacious home offers a great ocean view and is located on a canal with a dock and room for a boat up to 24 feet in length. Spread out over two levels, this spacious getaway features a full kitchen, a lower-level kitchenette, a patio, and a private, outdoor pool. This rental is an easy walk or bike ride to Sombrero Beach as well as the Turtle H
7-night minimum 7-night minimum
Canalfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 3 baths
Make your next tropical getaway one for the ages at this Key Colony Beach vacation rental, a breezy waterfront home with access to the Cabana Club. Wind down with a bit of poolside relaxation, or grab a cocktail at its bar and lounge. From its beach, you could also sunbathe, build sand castles with your kids, or swim out into the ocean. The home
7-night minimum 7-night minimum
KC01 - Captain's Haven Rating 5 (49)
Canalfront
- Key Colony Beach
Bedrooms 3 bedrooms
Bathrooms 3 baths
Escape to paradise in this lovely bayfront Key Colony Beach retreat! Right by the canal with its very own 35-foot dock space and access to the local Cabana Club, this home will be the best vacation home base you ever imagined. The quaint town of Key Colony Beach offers perfect beach living for everyone. Catch a charter and go find some dolphins, or
7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Welcome to DOCKSIDE, your perfect Keys escape! This charming canalside home is designed for couples seeking relaxation, romance, and adventure on the water. What You’ll Love • Large private dock just 215 feet from open water—bring your boat and enjoy quick access to the Atlantic. • Expansive deck & outdoor shower for sun-s
7-night minimum 7-night minimum
MA106 - Dockside Rating 5 (42)
Canalfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
The fresh ocean breeze will meet your skin every day when you settle down at this sun-filled Marathon condo! Open and spacious, special moments with your loved ones can be spent preparing delicious dishes in the full kitchen and sitting back and streaming on the living room's plush seating. Upstairs, the expansive primary bedroom offers its own
7-night minimum 7-night minimum
MA189 - La Nereida Rating 5 (18)
Condo
- Marathon
Bedrooms 1 bedroom
Bathrooms 2 baths
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit of being right in the heart of the island! You'll be in the cente
28-night minimum 28-night minimum
House
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
Dog Friendly Dog Friendly
Escape to the sunshine and soft sands of the Florida Keys with this amazing home in Sunrise Suites Resort in Key West with a shared pool. Sporting updates such as brand-new appliances, new sound-proof flooring, and a stackable washer/dryer, your stay is guaranteed to be a comfortable one.Back at home, you can stroll down a wooden walkway past a pri
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Situated in the heart of Key West, this unbelievable retreat will be the perfect place for entertaining the whole family! With three stories, high-end furnishings, and ample areas to spread out, there will ample room for everyone to indulge in their own kind of vacation. As if that isn't enough, recent renovations to enhance your stay include n
28-night minimum 28-night minimum
House
- Key West
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half Baths 1 half bath
Dreaming about a tropical vacation? This two-bedroom, one-bathroom cottage in Key West is the perfect destination - a private hot tub, garden, and a great location downtown will make this your best vacation yet!Located only half a block from the restaurants and bars on Duval Street, you'll have plenty to do within walking or biking distance of this
KW33B - Windward Isle Rating 5 (153)
House
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Dog Friendly Dog Friendly
Experience the very best of Key West living at this unique Old Town Truman Avenue Eyebrow home. Tucked away in a small, gated community, this luxury two-bedroom retreat showcases tranquil tropical decor and comes well-appointed with all the modern essentials of home. Whether you're visiting with the kids or sneaking away for a romantic couple&#
7-night minimum 7-night minimum
KW335WK - Dancing Palms Rating 5 (19)
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
This charming oceanfront two story townhouse offers uninterrupted water views and the laid-back luxury that Duck Key is known for. Perfect for families seeking a peaceful retreat with easy access to world-class boating, fishing, and waterfront relaxation. Step inside to a bright, coastal-inspired living space with comfortable seating and large wind
Canalfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath

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