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 52 properties available
Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back - what's not to love? Located half a block from
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KW33 - Tradewinds Rating 5 (181)
House
- Key West
Bedrooms 4 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
This turn-of-the-century Key West vacation rental is ready and waiting to be your home away from home for your next family getaway. Spacious enough for up to eight guests and a dog (for a small nightly fee), this home comes with a tropically landscaped back yard and a private, outdoor hot tub. This home also comes with convenient off-street parking
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Fall & Holiday Savings – Rates Reduced 15–20%!

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KW48 - Hemingway's View Rating 5 (240)
House
- Key West
Bedrooms 3 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Relax and enjoy the best of the Florida Keys from this charming canal-front retreat at Skipjack in Marathon. Perfectly located near the beach and just a short drive from downtown, this comfortable condo makes a great home base for a relaxing Keys getaway.The space features two queen beds, making it ideal for couples, friends, or a small family
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Canalfront
- Marathon
Bedrooms 1 bedroom
Bathrooms 1 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
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Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Plan your next getaway to this quaint tropical studio, complete with a well-equipped kitchenette, furnished patio, and access to a swimming pool, well-maintained tropical courtyard, and sundeck. This complex is located in a quiet, residential neighborhood, and street parking is available during your stay. Walk two blocks to the southernmost beach f
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Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

Condo
- Key West
Bathrooms 1 bath
Enjoy the unbeatable location of this two-story home only a block away from Duval Street. Take advantage of the large open concept living room, kitchen, and dining spaces while relaxing indoors. You can also beat the Florida heat by cooling off in the pool. This home is ready-made for group getaways with plenty of space to hang out together while s
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Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

KW230 - Last Minute Rating 5 (110)
House
- Key West
Bedrooms 3 bedrooms
Bathrooms 2 baths
Feel the stress melt away as you step through the front door of this tropical Key Largo condo, where serene oceanfront views greet you from two private balconies. Perched on the top floor, your Tavernier Escape offers sweeping water views and gentle breezes that set the tone for a peaceful getaway.Enjoy on‑site amenities including the community poo
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TA30 - Tavernier Escape #4408 Rating 4.9 (129)
Oceanfront
- Tavernier
Bedrooms 2 bedrooms
Bathrooms 2 baths
Ease into the pleasures of a tropical vacation with this two bedroom, two bathroom condo in Key West. With a charming atmosphere, entertainment, and two private parking spaces to save you any headaches, you'll speak nothing but praise during your stay in paradise! Located in the downstairs of a historic building just one block from the exc
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KW31A - Gardenia Getaway Rating 5 (284)
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
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
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DK21 - Palm Breeze - Villa 5030 Rating 4.9 (40)
Oceanfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half 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
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Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
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
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Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

DK12 - Harbor Villa 7103 Rating 5 (84)
Dry Lot
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath

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