Florida Keys Weekend Getaways
Need a quick getaway to relax, recharge, and get out on the water? The Florida Keys are made for long weekends—easygoing days, warm breezes, and just enough adventure to make it feel like a true escape.
Many of our properties offer nightly rentals, so you can slip away for a few days without committing to a full week. A long weekend in the Keys is the perfect way to unwind, reconnect, and trade your routine for something a little more memorable. Whether you’re planning a laid-back couples’ trip, a fishing weekend with friends, a family getaway, or a solo reset, these islands offer the ideal backdrop for a stress-free coastal escape.
A Home Base for Island Living
Unlike a hotel, a vacation home gives you the space and comfort to truly settle in. Start your mornings slowly with coffee on the patio, spend afternoons out on the water or by the pool, and wind down with easy dinners and open-air evenings. From waterfront homes with boat docks in Islamorada to relaxed retreats in Marathon and charming cottages in Key West, there’s a stay to match every kind of weekend.Closer to the Water
In the Keys, everything revolves around the water—and staying close to it makes all the difference. Wake up to canal or ocean views in Key Largo, step out for a quick boat ride in Islamorada, or enjoy sunset skies in Key West. Whether you’re looking for open-water views or quiet canal-front access, these homes keep your weekend simple and immersive.A Stress-Free Escape
You don’t need a full week to experience the Florida Keys—just a few good days. Spend your time however you want: fishing, snorkeling, boating, exploring local shops, or settling in with fresh seafood and a waterfront view. With a private home, everything feels easier, more comfortable, and entirely your own pace.Make Every Moment Count
Long weekends go fast—so make the most of every minute. Skip the hassle, settle in quickly, and spend more time enjoying the things that matter: sunshine, salt air, good food, and time with your favorite people.Perfect for Any Occasion
- Romantic Getaway – Sunset views, waterfront dinners, and slow mornings together.
- Family Getaway – Days on the water, pool time, and memory-making in a relaxed setting.
- Friends’ Weekend – Fishing trips, boat days, grilling out, and easy nights by the water.
- Solo Reset – Quiet mornings, open views, and the kind of calm you don’t get at home.
Book Your Florida Keys Long Weekend
Your next escape doesn’t have to wait. Browse our vacation homes across Key Largo, Islamorada, Marathon, and Key West, and find the perfect place to relax, recharge, and enjoy a long weekend in the Florida Keys.Not sure what you're looking for? Keep Searching: Oceanfront Rentals in the Florida Keys, Homes With Private Pools, Pet Friendly Vacation Rentals, Homes With Boat Docks, Homes That Offer Short Stays
19 properties available
You deserve a dreamy beach vacation, and this coastal condo is just the place to kick back and soak up that salty air. Wake up and look out at the greenery and unique landscape with a cup of coffee in hand. Head into the fully equipped kitchen and whip up a hearty breakfast for the group on modern appliances. When it is time to head out for the day
Welcome to your oceanfront retreat in Duck Key, FL! This charming townhouse offers a cozy and inviting atmosphere, perfect for a family getaway or a relaxing retreat. With stunning ocean views, you'll feel like you're in paradise from the moment you arrive. This family-friendly townhouse features a well-equipped kitchen with modern applianc
Set up on the fourth floor with a front-facing view of the adjacent waterway, this comfortable condo is an excellent option for that next romantic escape to the Keys! This property is less than a mile from groceries, shops, and restaurants. Inside this condo, you'll find a well-equipped, full kitchen, a four-seater dining table for mealtimes or
Escape to this charming townhouse in the heart of Hawks Cay Resort, where breathtaking water views greet you from the deck, balcony, and patio. Relax in the coastal breeze as you unwind with the soothing sounds of the waves—your perfect island getaway awaits. Step inside to find a well-equipped kitchen complete with a fridge, stove, oven, dis
Sun-soaked days and cool ocean breezes await you when you book your next retreat to this oceanfront Key Largo getaway. Featuring sweeping ocean views and shared amenities like a pool, on-site tennis, and beach access, fun will always be easy to find! Steps from the gently rolling waves, and just over seven miles from the heart of the island, you
Book your next vacation hideaway at this pool-view townhome, located at the amazing Kawama Yacht Club. You’ll love the community amenities, which include an outdoor pool, an outdoor kitchen, tennis courts, and a playground. Head down to the private beach with one of the community kayaks. An on-site marina offers services for additional usage
Escape to this waterfront, two-bedroom, one-and-a-half-bath Duck Key villa boasting breathtaking sunset views from your patio and balcony! This two-story end unit features nautical-inspired design elements paired with lots of natural light and privacy. Pick up a local fishing kit or bring your own, then spend leisurely afternoons fishing from the s
Gorgeously situated at the edge of an ocean canal, this Duck Key townhome is a place for azure water views, fragrant sea breezes, and basking in the blissfully slower pace of the Florida Keys. Spend your days fishing, getting out on the water, and unwinding in peace and scenery on your two-story waterfront porch. You'll also have access to a bo
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
Welcome to your Keys escape in Tavernier, Florida! This oceanfront condo puts you right at the water’s edge, where endless blue horizons and island breezes set the tone for your stay. Blending comfort with the laid-back charm of the Keys, it’s the perfect retreat for couples, families, or friends ready to soak up paradise. Start your mo
Welcome to your perfect vacation retreat in Key Largo, FL! This modern and spacious townhouse is ideally located in the Kawama Oceanside community, offering the closest proximity to the marina and beach area. With 3 bedrooms and 3 baths, there's plenty of room for the entire family to relax and unwind. Inside the townhouse, you'll find a li
With a wonderful location and a private sandy beach just steps away, this family-friendly townhouse is all set up for your beach getaway. Step inside and you'll be greeted by the charming full kitchen, remodeled as of spring 2021 and featuring granite countertops and full-size appliances for your cooking projects. Central air-conditioning will
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