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 54 properties available
Ideal for a small group or two couples traveling together and looking for a private, amenity-rich experience, this cozy second-floor tropical studio offers a well-equipped kitchenette, a furnished deck, and access to a swimming pool at the heart of a beautifully maintained tropical courtyard. Located two blocks from the southernmost beach and one b
House
- Key West
Bathrooms 1 bath
Soak up incredible west-facing views from the comfort of this elegant, dog-friendly Key West condo. First-rate amenities like a shared pool, exquisite tropical landscaping, and a private deck create a serene atmosphere that'll have you relaxed in no time. This condo is part of the upscale Sunrise Suites development, located on the eastern edge
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Experience Key West in style with this lovely vacation rental in the heart of Old Town! Up to six guests will enjoy a private hot tub and typical home comforts including a private washer/dryer, street parking, and free WiFi. Situated just one block from Duval Street, this cottage has no shortage of activities nearby. Sample some of the local restau
KW44 - Conch Casa Rating 5 (294)
House
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Whisk your special someone off to this enchanting Key West townhouse. Enjoy the shared pool and courtyard. The family dog is also welcome to join you for an additional nightly fee. Notice: This is in a residential area. Quiet Hours are 10 pm to 8 am. Park your car on the street and walk everywhere! This home is half a mile from the Southernmost Poi
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
Half Baths 1 half bath
Dog Friendly Dog Friendly
Breathe the fresh ocean air and gaze upon tropical sunsets on your next trip to Key West with this one-bedroom, one-bathroom condo. You'll enjoy entertainment, private parking, and a great central location that lets you make the most of your vacation. Part of a complex with three other condos in the middle of downtown, you'll be an easy wal
KW31D - Orchid Suite Rating 5 (272)
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
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
KL101 - Coastal Living Rating 4.9 (21)
Marina
- Key Largo
Bedrooms 3 bedrooms
Bathrooms 3 baths
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
Welcome to Ohana Keys, a bright and inviting townhome in the sought-after Kawama Yacht Club in Key Largo, where island adventures, resort-style amenities, and laid-back Florida Keys living come together.Whether you're here to relax by the pool, spend the day on the water, or explore the Keys, Ohana Keys gives you the perfect home base for your
KL201 - Ohana Keys Rating 5 (10)
Condo
- Key Largo
Bedrooms 2 bedrooms
Bathrooms 2 baths
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
Canalfront
- Duck Key
Bedrooms 4 bedrooms
Bathrooms 3 baths
Dog Friendly Dog Friendly
Escape to Key West's beaches during a stay at Atlantic Ocean View, where you'll enjoy prime island location and access to a shared pool. This condo accommodates up to six, so it's a great choice for the whole family! The Florida Keys Overseas Heritage Trail sits right outside the building, offering you easy access to Smathers Beach (hal
KW23 - Atlantic Ocean View Rating 5 (104)
Oceanfront
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy? This complex of three condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could hope for on a tropical vacation! Sitting only one block from the cent
KW31 - Three Flowers Guesthouse Rating 5 (116)
Condo
- Key West
Bedrooms 4 bedrooms
Bathrooms 4 baths

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