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
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
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
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
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
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
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
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
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
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
Welcome to Ohana Keys, your island getaway where stress drifts away on the breeze and paradise greets you at every turn. Nestled in the sought-after Kawama Yacht Club, this vibrant townhome offers not only comfort and style but also access to world-class amenities: a private beach with firepits and tiki bars, sparkling pools, a swimmable lagoon, gr
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
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