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 223 properties available
An escape to the Keys is never a bad idea, so treat yourself to a stylish getaway and kick back in bliss here at Coral Delight! Sitting right on the coast, you will have no delay in getting your fill of sweet sunshine, sandy toes, and sun-kissed skin. As soon as you step inside, you will be greeted by the tropical decor, plush furnishings, and plen
28-night minimum 28-night minimum
Canalfront
- Key Largo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
Dog Friendly Dog Friendly
Welcome to Gray Pelican House, your perfect canal-front escape in the heart of Key Colony Beach, one of the Florida Keys’ most peaceful and walkable communities. Whether you're visiting to relax, explore, or fish the open waters, this home puts island living right at your fingertips. Nestled on a deep-water canal with a 37-foot dock, the
7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
A true beach bungalow with a slice of private shoreline and a dock to boot, this full duplex is perfect for a relaxing getaway. Gather the whole family, including your canine pals (for a small nightly fee), and head to the land of sunshine and shorelines. One dog is also welcome to join you for an additional nightly fee. This home comprises two sep
7-night minimum 7-night minimum
Oceanfront
- Long Key
Bedrooms 4 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Come and experience everything the Sunshine State has to offer when you book this pleasant waterfront duplex! This splendid home away from home oozes a bohemian tropical vibe and enjoys an unbeatable location right behind Marathon International Airport and just a stone's throw from US 1. There's plenty to explore close to home. You can walk
7-night minimum 7-night minimum
MA172 - Bohemian Haven Rating 5 (3)
Canalfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
Bask in the peaceful sunshine of Key West and feel all your stress melt away when you stay at this cozy dog-friendly cottage right in town. With a private hot tub in the garden area out back plus all the conveniences of home, what's not to love?Sitting only half a block from all the fun and excitement of Duval Street, park your car in the private s
KW33A - Leeward Isle Rating 5 (75)
House
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Dog Friendly Dog Friendly
With fun beach decor, a bright interior, and plenty of room for everyone to spread out, no one will have trouble slipping into relaxation mode. Step out to your balcony with a fresh cup of coffee each morning or a glass of wine in the evening and breathe the salty air. After a full day of fun in the sun, the open layout of the full kitchen, dining
DK12 - Harbor Villa 7103 Rating 5 (67)
Dry Lot
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
Located on the banks of Sister Creek, this waterfront home is a coastal jewel! Book a snorkeling excursion to Sombrero Reef or hit the links at Florida Keys Country Club. Explore a variety of local dining options off Overseas Highway. Sip a crisp beverage as you take in views of Boot Key from the shaded cabana. Grill your local catch and dine alfre
7-night minimum 7-night minimum
Canalfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
✨ Waterfront Paradise with Private Beach, Dock & Ocean Views – Your Ultimate Keys Getaway! Discover your own slice of paradise in the Florida Keys at this sparkling, sun-kissed retreat! Nestled right on the water, this serene home offers the best of island living with unobstructed views of the inlet and open ocean, a private sandy beach,
7-night minimum 7-night minimum
KC85 - Casa Del Mar Rating 5 (14)
Oceanfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 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
*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.* This dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street. Nestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Ma
28-night minimum 28-night minimum
KW80FLR - Paradise Suite Rating 5 (13)
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
Half Baths 1 half bath
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
This stunning oceanfront property offers breathtaking views that provide the perfect backdrop for your vacation. The waterfront deck feels like a mini resort paradise with tropical thatched awnings, swaying palm trees, and classic beach-style furnishings. Make the most of your trip with access to the Cabana Club, offering beach access, a heated swi
7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 4 bedrooms
Bathrooms 4 baths
Dog Friendly Dog Friendly

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