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 216 properties available
🌴 TROPICAL BLISS ESCAPE – Key Largo Waterfront Getaway Escape to the laid-back charm of Key Largo, Florida, and discover the perfect blend of relaxation and adventure at this 3-bedroom, 2-bath waterfront retreat. With a private pool, guest dockage for boats up to 28 feet, and unbeatable access to both Florida Bay and the Atlantic Ocean, this
28-night minimum 28-night minimum
Canalfront
- Key Largo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Welcome to Ohana Keys, your island getaway where stress drifts away on the breeze and paradise greets you at every turn. Nestled in the sought-after Kawama Yacht Club, this vibrant townhome offers not only comfort and style but also access to world-class amenities: a private beach with firepits and tiki bars, sparkling pools, a swimmable lagoon, gr
KL201 - Ohana Keys Rating 5 (10)
Condo
- Key Largo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Welcome to your slice of paradise in Key West’s coveted Truman Annex. Tucked within the charming Shipyard community, this inviting townhome places you in the heart of it all—just steps from the sugar-white sands of Fort Zachary Taylor Beach and a short stroll to Mallory Square’s legendary sunset celebrations. With Duval Street onl
28-night minimum 28-night minimum
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Complete with upscale resort amenities like a shared pool and hot tub, tennis courts, and a private, covered parking space, this comfortable rental is sure to become your new favorite tropical getaway. One dog is allowed. This rental is
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
The Tree Lane Fish Camp: Updated, Cozy home in TavernierBed Sizes: 2 Queen, 1 Double Trundle Bed, 2 Double Sleep SofasWelcome to your laid-back diving retreat in Tavernier, where life moves with the tides and every day ends with a sunset over the water. Nestled in the heart of the Florida Keys, this home is built for anglers, boaters, and anyone wh
28-night minimum 28-night minimum
Dry Lot
- Tavernier
Bedrooms 3 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
*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 (15)
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
Half Baths 1 half bath
Dog Friendly Dog Friendly
Everything you need for a carefree Florida Keys escape is right at your fingertips in this laid-back bungalow. Boasting direct canal access by way of a private dock, this waterfront retreat also features a tropical outdoor area and recent home upgrades including an all-new kitchen and primary bathroom. A fully screened-in lanai offers a breezy perc
28-night minimum 28-night minimum
Canalfront
- Summerland Key
Bedrooms 3 bedrooms
Bathrooms 2 baths
The Keys are calling, so spoil yourself with an unforgettable stay in this fantastic canal-front home! You won't have to leave home base to soak up some of the best views, as the calm canal waters await right outside, as well as a 122-foot private dock to tie up any kayaks and toys. The exterior is a fun, bright green color, just adding to the
28-night minimum 28-night minimum
Canalfront
- Key Largo
Bedrooms 4 bedrooms
Bathrooms 3 baths
Slip into the beach lifestyle and leave the daily grind behind when you book your stay at this oceanfront Layton cottage. With a dock, expansive deck, and a stunning beach location, you may never want to leave. With historic roots as the home to the 1900's author, Zane Grey, and easy access to a bevy of beach activities, your stay promises to b
7-night minimum 7-night minimum
Oceanfront
- Long Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Dog Friendly Dog Friendly
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 priv
KW33A - Leeward Isle Rating 5 (114)
House
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Dog Friendly Dog Friendly
*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 home is perfect for anyone coming to the Keys to spend time on the water. The two-story home sits on the widest canal in Hammer Point that leads to Florida Bay and has its own private dock capable
28-night minimum 28-night minimum
TA06FLR - Tarpon Cove Rating 5 (17)
Canalfront
- Tavernier
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
This home is just perfect for your Keys getaway! The open floor plan and well-appointed kitchen will make your stay more than comfortable. French doors off the living room and primary bedroom offer beautiful views of the private pool and the lush tropical landscape in the enclosed yard. You will enjoy the private outdoor living area, including the
28-night minimum 28-night minimum
House
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly

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