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 204 properties available
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
KW33B - Windward Isle Rating 5 (171)
House
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Dog Friendly Dog Friendly
Welcome to your tropical escape in the heart of the Florida Keys!Leave the everyday behind and settle into island time at this beautifully appointed retreat, where sunshine, adventure, and relaxation await. Whether you're looking for a peaceful getaway or an action-packed vacation, this is the perfect home base for experiencing all that the Flo
7-night minimum 7-night minimum
Condo
- Marathon
Bedrooms 1 bedroom
Bathrooms 2 baths
Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a private pool completely surrounded by a rustling wall of palm trees, this upscale rental offers a private, tranquil getaway right in the bustling heart of Key West. This home lies just two blocks away from Higgs Beach and the Edw
28-night minimum 28-night minimum
KW219FLR - Sunshine Drive Rating 5 (7)
House
- Key West
Bedrooms 3 bedrooms
Bathrooms 3 baths
Right by the glistening waters of Florida lies this beautiful home! You'll be within driving distance of some amazing attractions such as the National Key Deer Refuge Nature Center, where you can experience the natural beauty of the world around you and contribute to something greater, and Big Pine Key Park, where you'll be able to set up a
28-night minimum 28-night minimum
Canalfront
- Big Pine Key
Bedrooms 2 bedrooms
Bathrooms 2 baths
Bougainvillea Villas – Marathon, FloridaEscape to the exclusive Bougainvillea Villas, a private, secured‑gated community in Marathon, FL, featuring just 14 stunning homes. This beautifully appointed house offers access to a shared bayside pool and fishing pier, creating the perfect setting for a tranquil waterfront retreat.🌴 Luxury & Com
7-night minimum 7-night minimum
MA216 - Villa del Sol Rating 5 (3)
House
- Marathon
Bedrooms 3 bedrooms
Bathrooms 3 baths
Book this newly renovated home that sits on a major canal, where guests can tie off a boat, in the Indian Waterways neighborhood. The nautical-themed decoration throughout the house will truly help you leave all of your worries behind and focus on having a great time! The family dog is also welcome to join in the fun here. The home features a 60-fo
28-night minimum 28-night minimum
TA08FLR - Islamorada Haven Rating 5 (12)
Canalfront
- Tavernier
Bedrooms 2 bedrooms
Bathrooms 1 bath
Dog Friendly Dog Friendly
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
License number: 25,230-1322,99. Welcome to Paradise in Key Largo – your private waterfront oasis just one mile from the breathtaking John Pennekamp Coral Reef State Park! Whether you're looking for outdoor adventures, a family retreat, or simply peace and quiet in the Florida Keys, this spacious and beautifully appointed home offers the p
28-night minimum 28-night minimum
Canalfront
- Key Largo
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath
Dog Friendly Dog Friendly
Say hello to pure coastal bliss right on the harbor at this fabulous Duck Key escape. Sea and Sky will have you slipping into vacation mode in no time, as you can wake up, brew a fresh pot of coffee, and step out to your furnished deck to watch the sunrise over calm waters, mere steps away. The private dock will also be just the place to launch the
28-night minimum 28-night minimum
MA143FLR - Sea and Sky Rating 5 (3)
Oceanfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Paradise truly abounds at this modern waterfront masterpiece in the heart of the Florida Keys. Designed with marble finishes, soaring ceilings, and walls of sunlight, Tropical Delight invites you to relax in style while enjoying the laid-back island lifestyle. ✨ Interior Highlights Step into the open-concept living space, where the living room, din
7-night minimum 7-night minimum
MA183 - Tropical Delight Rating 5 (18)
Canalfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
Spend your days soaking up the sun and cruising the Florida Keys when you escape to this light-filled, waterfront home, beautifully situated among the canals and palms of Key Colony Beach. Enjoy your own 60-foot dock, a canalside patio, and a wonderful location for golfing, fishing, and beach-going. This single-story home sits at the edge of an oce
7-night minimum 7-night minimum
KC100 - Breezy Keys Rating 5 (12)
Canalfront
- Key Colony Beach
Bedrooms 4 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy? This complex of three condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could hope for on a tropical vacation! Sitting only one block from the cent
KW31 - Three Flowers Guesthouse Rating 5 (115)
Condo
- Key West
Bedrooms 4 bedrooms
Bathrooms 4 baths

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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.