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 213 properties available
Enjoy the unbeatable location of this two-story home only a block away from Duval Street. Take advantage of the large open concept living room, kitchen, and dining spaces while relaxing indoors. You can also beat the Florida heat by cooling off in the pool. This home is ready-made for group getaways with plenty of space to hang out together while s
KW230 - Last Minute Rating 5 (109)
House
- Key West
Bedrooms 3 bedrooms
Bathrooms 2 baths
Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of luxury and total relaxation. This rental is part of the upscale Sunrise Suites Resort, loca
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Escape to Key West's beaches during a stay at Atlantic Ocean View, where you'll enjoy prime island location and access to a shared pool. This condo accommodates up to six, so it's a great choice for the whole family! The Florida Keys Overseas Heritage Trail sits right outside the building, offering you easy access to Smathers Beach (hal
KW23 - Atlantic Ocean View Rating 5 (103)
Oceanfront
- 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
Oceanfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath
Welcome to Sunset Suite -- Catalina Suite 311, your slice of paradise in vibrant Key West! This inviting two-bedroom condo is part of the upscale Sunrise Suites Resort, where tropical comfort meets resort-style amenities. Step onto your private deck to soak in the island breeze, then spend your day swimming in the heated pool, unwinding in the hot
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Welcome to your waterfront escape in the Florida Keys, where breathtaking Gulf views, a private pool, and endless boating adventures await!Whether you're planning a relaxing getaway or an unforgettable family vacation, this beautifully remodeled two-bedroom canal-front home offers everything you need to experience the very best of island living
7-night minimum 7-night minimum
MA97 - Marathon Memories Rating 5 (36)
Canalfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 1 bath
Dog Friendly Dog Friendly
Escape to paradise at this inviting pool-view townhome in the sought-after Kawama Yacht Club in Key Largo! With fantastic community amenities, comfortable indoor and outdoor spaces, and easy access to the beach, this home is the perfect setting for a relaxing Florida Keys vacation.Enjoy your morning coffee from the screened porch, take a refreshing
KL60 - Kawama Yacht Club A4 Rating 5 (31)
Marina
- Key Largo
Bedrooms 2 bedrooms
Bathrooms 2 baths
This lovely waterfront duplex hosting lush interiors and incredible water views will surely be the highlight of your next Key Colony Beach escape! Ideally located for fun and recreation, you’ll find Key Colony Beach Golf, Sunset Park, and Florida Keys Aquarium Encounters all within a two-mile radius. Spend a day playing a leisurely round of g
7-night minimum 7-night minimum
KC202 - Ocean Oasis III Rating 5 (4)
Canalfront
- Key Colony Beach
Bedrooms 5 bedrooms
Bathrooms 3 baths
Step back in time—while enjoying every modern comfort—in this beautifully appointed three-story condo nestled within the legendary grounds of the historic Long Key Fishing Club in Layton, Florida. Once the prized fishing destination of icons like Theodore Roosevelt and Zane Grey, this area was famously known as Henry Flagler’s Lon
28-night minimum 28-night minimum
Condo
- Layton
Bedrooms 2 bedrooms
Bathrooms 3 baths
Half Baths 1 half bath
Bask in the tropics of Key West at this inviting cottage with a private heated pool and a lush backyard garden. This lovely cottage is located in Old Town near Duval Street, minutes from restaurants, museums, and the daily sunset celebration at Mallory Square. Stay cool with air conditioning, cook up food on the gas grill, and dine outside on pleas
KW24 - Key Lime Calypso Rating 5 (277)
House
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
This second-floor tropical studio has a private outdoor seating area and plenty of space for your vacation crew. Spend time splashing in the shared pool or catch some rays on the sundeck. Located in a residential neighborhood two blocks from the southernmost beach and just one block from Duval Street for the area's best restaurants, shops, terr
House
- Key West
Bathrooms 1 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 (309)
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath

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Florida Keys Vacation Rental FAQs

What types of Florida Keys vacation rentals are available?

Florida Keys vacation rentals include houses, condos, waterfront properties, oceanfront stays, and accommodations with a variety of amenities. Available options vary by destination, travel dates, property size, and minimum-stay requirements.

Where should I stay in the Florida Keys?

The best location depends on the type of vacation you are planning. Key Largo is popular for diving, snorkeling, and boating, Islamorada is well known for fishing and waterfront activities, Marathon provides a convenient Middle Keys location, the Lower Keys offer a quieter island setting, and Key West combines historic attractions, dining, entertainment, beaches, and nightlife.

Are waterfront Florida Keys vacation rentals available?

Yes. Waterfront, canalfront, oceanfront, and water-view vacation rentals may be available throughout the Florida Keys. Water access and views vary by property, so review each individual listing for current details.

Can I find Florida Keys vacation rentals with boat docks?

Boat-dock rentals are available among select Florida Keys properties. If you are bringing a boat, check the individual property listing for dock dimensions, water depth, boat restrictions, trailer parking, and other boating information before booking. You can also browse Florida Keys rentals with boat docks to narrow your search.

Are Florida Keys vacation rentals with private pools available?

Yes. Some Florida Keys vacation rentals feature private pools, while others may provide access to a shared or community pool. Browse Florida Keys rentals with private pools or check the amenity details on each property page.

Are pet-friendly Florida Keys vacation rentals available?

Pet-friendly vacation rentals may be available throughout the Florida Keys. Pet policies, fees, size limits, and the number of permitted pets vary by property. Visit our pet-friendly Florida Keys rentals page or review the individual property listing before booking.

How long can I stay in a Florida Keys vacation rental?

Minimum-stay requirements vary by property, location, season, and travel dates. Some rentals allow shorter stays, while others require seven nights, 28 nights, or longer. Guests planning an extended trip can also browse Florida Keys weekly rentals and Florida Keys monthly rentals.

How do I narrow down the Florida Keys vacation rentals?

Start by entering your arrival and departure dates, then use the available filters to narrow rentals by location, bedrooms, bathrooms, property type, and amenities such as boat docks, pools, ocean views, parking, and pet-friendly accommodations.

Can I search Florida Keys vacation rentals by destination?

Yes. You can browse rentals by destination, including Key Largo, Islamorada, the Middle Keys, the Lower Keys, and Key West.