Weekly Rentals in the Florida Keys
Florida Keys weekly vacation rentals—defined as homes that rent for 7 days or more— offer the perfect way to settle into island life and truly experience everything the Keys have to offer. With a 7-night stay, you’ll have time to slow down, explore at your own pace, and enjoy both the water and the moments in between. From Key Largo to Key West, our homes are designed for longer stays that feel relaxed, comfortable, and complete.
Whether you're traveling with family, friends, or planning an extended getaway, weekly rentals provide the space and flexibility to make the most of your time in the Florida Keys.
Why Choose a Weekly Stay?
A week in the Florida Keys gives you the chance to experience more than just a quick visit. Instead of rushing from one activity to the next, you can settle in, explore different areas, and enjoy a more natural rhythm to your days.
Spend time boating, fishing, snorkeling, or simply relaxing by the pool—then return to your home base each day without feeling like your trip is flying by.
More Time to Explore the Keys
With a full week, you can experience the unique character of each part of the island chain. Discover the natural beauty of Islamorada, enjoy the variety of activities in Marathon, or plan a day trip to Key West for dining, shopping, and entertainment.
A longer stay means you don’t have to choose—you can experience it all.
Settle In & Feel at Home
Weekly vacation homes are ideal for creating a true home-away-from-home experience. With multiple bedrooms, full kitchens, and comfortable living spaces, you’ll have room to spread out, cook meals, and enjoy time together.
Many homes also feature outdoor living areas, pools, docks, and water access—giving you everything you need to enjoy the Florida Keys lifestyle throughout your stay.
A Better Way to Vacation
There’s something different about staying a full week. You start to recognize the views, fall into a routine, and experience the Keys like a local. Mornings feel slower, evenings feel longer, and the entire trip becomes more meaningful.
Book Your Florida Keys Weekly Stay
If you’re looking for a more relaxed, immersive vacation, a 7-night stay is the way to do it. With more time to explore, unwind, and connect, weekly rentals offer the full Florida Keys experience.
Browse our weekly vacation rentals and start planning your next island escape.
76 properties available
Welcome to DOCKSIDE, your perfect Keys escape! This charming canalside home is designed for couples seeking relaxation, romance, and adventure on the water. What You’ll Love • Large private dock just 215 feet from open water—bring your boat and enjoy quick access to the Atlantic. • Expansive deck & outdoor shower for sun-s
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
Get a taste of the coastal lifestyle in Key Colony Beach when you make this newly updated home your retreat away from home! Sitting on the area's unique canal system, enjoy your favorite drinks on the patio with views of the water. Bright and spacious, the interior features all of the comforts of home. Though it will be hard to leave the comfor
Welcome to your deluxe beach getaway here in Key Colony Beach, where you can enjoy exclusive access to the Cabana Club! With waterfront views, you'll have the perfect setting for a relaxing vacation. This property features a patio with a gas grill, ideal for alfresco dining while enjoying the ocean breezes. Inside, the well-equipped, full kitch
Make your next trip to the Florida Keys the best one yet with this Key Colony beach home, which offers a Cabana Club membership, access to a private beach, and private 35-foot dock for the ideal Florida vacation. This canal-side home is perfect for boaters and fans of watersports, with easy access to scuba diving, snorkeling, and sport fishing! Bac
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
This colorful, waterfront home, located right on the canal with a dock, offers easy access to the ocean or the Gulf. This location is the perfect spot for families to build memories while enjoying your favorite watersports. The home has a full kitchen for easy meal preparation and plenty of space for dining both inside or outside on the furnished b
This spacious home offers a great ocean view and is located on a canal with a dock and room for a boat up to 24 feet in length. Spread out over two levels, this spacious getaway features a full kitchen, a lower-level kitchenette, a patio, and a private, outdoor pool. This rental is an easy walk or bike ride to Sombrero Beach as well as the Turtle H
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
Located in Marathon, FL, this spacious house is the perfect retreat for families or groups looking to enjoy the beauty of the Florida Keys. With a private pool, patio furniture, and a gas grill, the outdoor space is ideal for soaking up the sun and enjoying al fresco dining. The house features multiple levels, providing plenty of space for everyone
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
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
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