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
18 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
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
Located on the upscale Duck Key in a quiet neighborhood known as the Village in Hawks Cay, this waterfront townhouse offers the ideal restful retreat. Take in breathtaking views of the Duck Key Marina, Toms Harbor, and the Seven Mile Bridge in the distance! Spend leisurely afternoons fishing from the shoreline, right outside your door. You'll a
With fun beach decor, a bright interior, and plenty of room for everyone to spread out, no one will have trouble slipping into relaxation mode. Step out to your balcony with a fresh cup of coffee each morning or a glass of wine in the evening and breathe the salty air. After a full day of fun in the sun, the open layout of the full kitchen, dining
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
Feel the stress melt away as you step through the front door of this tropical Key Largo condo, boasting serene oceanfront views from two private balconies. The top-floor location immerses you in beautiful water views and gentle breezes on your private Tavernier Escape. Enjoy on-site amenities like the community pool and gazebo, a waterfront caf&eac
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
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
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
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
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
Make vacation wishes come true at this two-bedroom, two-and-a-half-bath Duck Key waterfront villa. Set right on a canal in the heart of the Florida Keys, this lovely retreat features shimmering water views. Take in the beautiful vistas from the private pool or head directly to the water to launch the provided kayak and paddleboard. The beauty of th
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