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
*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.* Head to Key West and revel in access to a shared pool, dog-friendly accommodations, and close proximity to beautiful beaches and major attractions when you stay at this three-bedroom, three-bath home fo
House
- Key West
Bedrooms 3 bedrooms
Bathrooms 3 baths
Dog Friendly Dog Friendly
✨ Tollgate Tides blends comfort and adventure in one perfect waterfront escape. Whether you’re here for fishing, snorkeling, sunset cruises, or simply soaking up the tropical vibe, you’ll find everything you need to create unforgettable Florida Keys memories.⭐ Location Highlights Robbie’s of Islamorada (10 miles): Feed the famous
Canalfront
- Islamorada
Bedrooms 2 bedrooms
Bathrooms 2 baths
☀️ SNOWBIRD-FRIENDLY ISLAND ESCAPE - WALK TO DUVAL, BALCONY VIEWS, POOL & BEACH ACCESS! Welcome to your charming Key West hideaway, where coastal comfort, garden views, and an unbeatable location come together to create the perfect island retreat. This snowbird-friendly, two-story condo is nestled just a short stroll from the beach and blocks
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Ease into the pleasures of a tropical vacation with this two bedroom, two bathroom condo in Key West. With a charming atmosphere, entertainment, and two private parking spaces to save you any headaches, you'll speak nothing but praise during your stay in paradise! Located in the downstairs of a historic building just one block from the exc
KW31A - Gardenia Getaway Rating 5 (282)
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Perched on Little Torch Key, this charming house offers breathtaking views of Pine Channel, creating a serene backdrop for your vacation. With a BBQ area and a private dock, you can enjoy outdoor dining while watching the boats go by or try your hand at fishing right from your doorstep. Inside, you'll find a cozy retreat with all the amenities
Canalfront
- Little Torch Key
Bedrooms 3 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Relaxation comes easy at this canal-side home in the private Yacht Harbor neighborhood in Marathon. A private, sparkling pool completes your resort-style outdoor oasis. A screened patio at the rear of the house offers a relaxed social space with a pair of loungers and a high-top table. Sunbathe on lounge chairs between refreshing dips. You can soak
MA118 - Coral Cove Rating 5 (43)
Canalfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
Slip into island time at this one-bedroom, one-bath condo for four in Key West, where you'll have entertainment and nearby beach access in an awesome central location. Sitting right downtown on Simonton Street, you're one street over from all the restaurants and bars on Duval, and within easy walking or biking distance from all the main att
KW31C - Jasmine Suite Rating 5 (308)
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
Find a relaxing respite for days spent fishing, boating, and swimming at this two-story condo in Marathon, the perfect setting for embracing the Florida Keys lifestyle. Ocean Isles Fishing Village is ideal in many ways, with grounds including a waterfront swimming pool and sundeck. One small kayak and three paddle boards so you can easily get out o
Condo
- Marathon
Bedrooms 1 bedroom
Bathrooms 2 baths
Stylish seaside studio situated near the northern end of Marathon, you'll enjoy a convenient location for all your favorite Florida Keys activities - both on and off the water. Additional on-site perks including an oceanfront pool and shady, palapa-style picnic benches let you indulge in waterfront leisure just steps from your front door. Some
MA186 - Ocean Isles 50 Rating 5 (15)
Condo
- Marathon
Bathrooms 1 bath
With a 60-foot dock right on the canal and access to the nearby Cabana Club's shared pools and private beach, this dog-friendly bungalow is perfect for your next getaway to sunny Florida! Located in Key Colony Beach, this home for six is located on a canal, with swimming and fishing available in your backyard - you even have a bait freezer. The
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
*Please note that this home only allows minimum stays of 7 nights or longer. This is enforced by the city and we cannot make any exceptions. Fisherman's Hideaway is the perfect home base for your next fishing trip to Conch Key! This snowbird-friendly studio comes with access to open water via the deepwater docking out back, as well as use of a
Canalfront
- Conch Key
Bedrooms 1 bedroom
Bathrooms 1 bath
This canal-front home has a nice upper-level balcony overlooking the water, which is excellent for morning coffee or evening cocktails. The spacious living area invites everyone to kick back, relax, and enjoy watching TV or planning their next adventure. Take advantage of the well-equipped kitchen and treat your group to a tasty homemade meal. WHAT
Canalfront
- Key Largo
Bedrooms 2 bedrooms
Bathrooms 1 bath

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