Florida Keys Weekend Getaways

Plan a Florida Keys weekend getaway and trade the usual routine for warm weather, waterfront views, fresh seafood, and a few well-spent days on island time. Select Seven Keys vacation rentals offer shorter stays, making it easier to plan a quick couples trip, family getaway, fishing weekend, or last-minute escape without booking an entire week.

Choose a vacation rental in Key Largo for snorkeling, diving, and easy access from South Florida. Browse Islamorada vacation rentals for fishing, boating, marinas, and waterfront dining. Stay near Marathon and Duck Key with our Middle Keys rentals, or head farther south for a relaxing stay in the Lower Keys or an activity-filled weekend in a Key West vacation rental.

Find a Florida Keys Rental for a Short Stay

A vacation rental gives you more room and flexibility than a traditional hotel stay. Enjoy separate bedrooms, comfortable living areas, kitchen space, outdoor seating, and the privacy to follow your own schedule. Available properties may include waterfront homes, Florida Keys condos, private pool rentals, pet-friendly homes, and rentals with boat docks.

Florida Keys weekend rentals are a great fit for romantic getaways, family trips, boating adventures, fishing weekends, celebrations, or a quiet few days away. Spend your time snorkeling, paddling, exploring local restaurants, relaxing by the pool, or simply enjoying the view from your rental.

Planning Your Florida Keys Weekend Getaway

Short-stay availability and minimum-night requirements vary by property, season, and travel dates. Enter your preferred arrival and departure dates to view rentals available for your trip. Before booking, review the individual property details for sleeping arrangements, parking, pool access, dock information, pet policies, and other amenities.

Browse available Florida Keys weekend getaways below and book direct with Seven Keys Vacations for a locally managed rental experience.

Florida Keys weekend getaway with turquoise water, palm trees, and waterfront vacation scenery

Properties Available 57 properties available
Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Complete with upscale resort amenities like a shared pool and hot tub, tennis courts, and a private, covered parking space, this comfortable rental is sure to become your new favorite tropical getaway. One dog is allowed. This rental is
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Bask in the peaceful sunshine of Key West and feel all your stress melt away when you stay at this cozy dog-friendly cottage right in town. With a private hot tub in the garden area out back plus all the conveniences of home, what's not to love? Sitting only half a block from all the fun and excitement of Duval Street, park your car in the priv
KW33A - Leeward Isle Rating 5 (114)
House
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Dog Friendly Dog Friendly
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
Marina
- Tavernier
Bedrooms 2 bedrooms
Bathrooms 2 baths
Treat your family to an unforgettable stay in Key West with this dog-friendly condo. Modern conveniences combine with a great location and first-class resort amenities - you'll love this adventure so much, you'll never want to head back home! When you're done swimming in the shared pool or soaking in the shared hot tub, you can towel of
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Charming Key West Cottage – Walk to Duval Street & Relax by the PoolEscape to the laid-back charm of Key West and enjoy a relaxing stay in this inviting one-bedroom, one-bathroom cottage, perfectly designed for couples seeking an unforgettable island getaway.Nestled in a peaceful setting just off Truman Avenue, this charming retreat place
KW37 - Oceana Suite Rating 4.9 (282)
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
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
Oceanfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath
Welcome to your beautifully renovated Key West retreat at Sunrise Suites Resort!Whether you're planning a romantic getaway, a family vacation, or a relaxing escape with friends, this stunning two-bedroom condo offers the perfect combination of modern luxury, resort-style amenities, and the laid-back charm of Key West.Completely remodeled from t
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
This second-floor tropical studio has a private outdoor seating area and plenty of space for your vacation crew. Spend time splashing in the shared pool or catch some rays on the sundeck. Located in a residential neighborhood two blocks from the southernmost beach and just one block from Duval Street for the area's best restaurants, shops, terr
House
- Key West
Bathrooms 1 bath
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
Canalfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath
Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of luxury and total relaxation. This rental is part of the upscale Sunrise Suites Resort, loca
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Tropical comfort abounds when you stay at this wonderful condo on the shores of Key West. Complete with a shared pool & hot tub, tennis courts, and a private, covered parking space, you'll have everything you need for an unforgettable Florida Keys escape. One dog is allowed. Located on the eastern side of the island, this condo is part of t
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly

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