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
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
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
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 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
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
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
Sun‑soaked days and cool ocean breezes await you at this oceanfront Key Largo retreat. With sweeping ocean views and shared amenities such as a pool, on‑site tennis, and private beach access, you'll find that fun and relaxation are always within reach.Just steps from the gently rolling waves and a little over seven miles from the heart of the i
Feel the stress melt away as you step into this coastal Key Largo condo, where breezy tropical charm and peaceful surroundings set the tone for your stay. Wake up to lush greenery and the unique island landscape from your private balcony, coffee in hand, as the day begins at your own relaxed pace.Inside, the open, light‑filled layout features coast
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
Create unforgettable memories in the heart of the Florida Keys with a stay at this delightful waterfront townhouse on picturesque Duck Key. Set along a serene canal with easy proximity to nearby restaurants, spas, and excursions, this home offers everything you need for a relaxing and adventure-filled getaway. Step inside to find a bright, coastal-
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
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
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