Florida Keys Vacation Rentals

Browse Florida Keys vacation rentals with Seven Keys Vacations and find a home base that fits the way you want to experience the islands. Our collection includes vacation homes, condo rentals, waterfront stays, private pool homes, pet-friendly rentals, boat dock homes, and longer stay options across Key West, Key Largo, Islamorada, Marathon, Big Pine Key, and the Lower Keys.

Every part of the Keys has its own rhythm. Stay in a Key West vacation rental for walkable dining, historic streets, nightlife, and sunset celebrations. Choose Key Largo vacation rentals for easy access to snorkeling, diving, and boating. Settle into Islamorada vacation rentals if fishing, marinas, and waterfront restaurants are high on the list. For a central island stay, browse Middle Keys vacation rentals near Marathon, or look to Lower Keys vacation rentals for a quieter, more laid-back escape.

Find the Right Florida Keys Rental for Your Trip

Planning a family vacation, fishing trip, couples getaway, remote work stay, or longer island escape? Use the filters to compare Florida Keys house rentals, Florida Keys condo rentals, ocean view rentals, pet-friendly homes, private pool rentals, and vacation rentals with boat docks. You can also narrow your search by travel dates, bedrooms, location, amenities, and stay length.

If you are staying for a full week or longer, our weekly rentals in the Florida Keys make it easier to settle in and enjoy the islands at a slower pace. Guests planning an extended winter stay, remote work trip, or seasonal getaway can also explore monthly rentals in the Florida Keys for more time on the water, more flexibility, and a little less suitcase chaos.

Browse available Florida Keys vacation rentals below and book direct with Seven Keys Vacations for a more personal, locally focused rental experience.

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

Properties Available 202 properties available
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
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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 1 bedroom
Bathrooms 1 bath
Half Baths 1 half bath
Dog Friendly Dog Friendly
Right on the canal, this half-duplex is perfect for your Florida vacation. With its own private dock and access to the Cabana Club, this home is perfect for water lovers! Key Colony Beach's small size puts you within walking distance of much of what the city has to offer. Plus, since you're right on the canal, you'll be able to enjoy yo
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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!

7-night minimum 7-night minimum
KC22 - Ninth Street Getaway Rating 5 (70)
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Get a daily dose of sunshine and sea breezes at this waterfront retreat in Key Colony Beach. Primed for carefree coastal living, this breezy bungalow comes fully renovated throughout with all the modern comforts and essentials of home. Enjoy direct water access by way of private dock and take in the views on the covered lanai furnished for outdoor
Specials Tag View Special
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!

7-night minimum 7-night minimum
KC90 - Vitamin Sea Rating 5 (28)
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
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-
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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!

DK27 - Key Lime Villa 7003 Rating 5 (62)
Canalfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 2 baths
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
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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!

Oceanfront
- Tavernier
Bedrooms 2 bedrooms
Bathrooms 2 baths
The fresh ocean breeze will meet your skin every day when you settle down at this sun-filled Marathon condo! Open and spacious, special moments with your loved ones can be spent preparing delicious dishes in the full kitchen and sitting back and streaming on the living room's plush seating. Upstairs, the expansive primary bedroom offers its own
Specials Tag View Special
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!

7-night minimum 7-night minimum
MA189 - La Nereida Rating 4.9 (24)
Condo
- Marathon
Bedrooms 1 bedroom
Bathrooms 2 baths
Your Key West Hideaway – Historic Charm Meets Island StyleCome experience the colorful character and unmistakable charm of Key West from this beautifully updated classic cottage! With a welcoming atmosphere, comfortable accommodations for up to eight guests, and a central location close to the island’s beloved attractions, this three-be
28-night minimum 28-night minimum
KW302FLR - Key Rest Rating 5 (2)
House
- Key West
Bedrooms 3 bedrooms
Bathrooms 2 baths
Your Oceanfront Escape Awaits in Tavernier!Imagine waking up to endless ocean views, sipping your morning coffee on a private balcony, and feeling the warm island breeze. Welcome to your Florida Keys getaway in beautiful Tavernier, where relaxation, adventure, and laid-back island living come together!This inviting oceanfront condo offers the perfe
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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!

Marina
- Tavernier
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
Specials Tag View Special
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!

House
- Key West
Bathrooms 1 bath
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
Specials Tag View Special
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
License number: 25,230-1322,99. Welcome to Paradise in Key Largo – your private waterfront oasis just one mile from the breathtaking John Pennekamp Coral Reef State Park! Whether you're looking for outdoor adventures, a family retreat, or simply peace and quiet in the Florida Keys, this spacious and beautifully appointed home offers the p
28-night minimum 28-night minimum
Canalfront
- Key Largo
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath
Dog Friendly Dog Friendly
Welcome to Your Waterfront Escape in Key Largo! Tucked along a peaceful canal with stunning water views, this tropical retreat is your gateway to both relaxation and adventure in the Florida Keys. Perfectly positioned between the Atlantic Ocean and Florida Bay, you’re just minutes from world-class boating, fishing, snorkeling, and sunsets you
28-night minimum 28-night minimum
Canalfront
- Key Largo
Bedrooms 3 bedrooms
Bathrooms 3 baths

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Florida Keys Vacation Rental FAQs

What types of Florida Keys vacation rentals are available?

Florida Keys vacation rentals include houses, condos, waterfront properties, oceanfront stays, and accommodations with a variety of amenities. Available options vary by destination, travel dates, property size, and minimum-stay requirements.

Where should I stay in the Florida Keys?

The best location depends on the type of vacation you are planning. Key Largo is popular for diving, snorkeling, and boating, Islamorada is well known for fishing and waterfront activities, Marathon provides a convenient Middle Keys location, the Lower Keys offer a quieter island setting, and Key West combines historic attractions, dining, entertainment, beaches, and nightlife.

Are waterfront Florida Keys vacation rentals available?

Yes. Waterfront, canalfront, oceanfront, and water-view vacation rentals may be available throughout the Florida Keys. Water access and views vary by property, so review each individual listing for current details.

Can I find Florida Keys vacation rentals with boat docks?

Boat-dock rentals are available among select Florida Keys properties. If you are bringing a boat, check the individual property listing for dock dimensions, water depth, boat restrictions, trailer parking, and other boating information before booking. You can also browse Florida Keys rentals with boat docks to narrow your search.

Are Florida Keys vacation rentals with private pools available?

Yes. Some Florida Keys vacation rentals feature private pools, while others may provide access to a shared or community pool. Browse Florida Keys rentals with private pools or check the amenity details on each property page.

Are pet-friendly Florida Keys vacation rentals available?

Pet-friendly vacation rentals may be available throughout the Florida Keys. Pet policies, fees, size limits, and the number of permitted pets vary by property. Visit our pet-friendly Florida Keys rentals page or review the individual property listing before booking.

How long can I stay in a Florida Keys vacation rental?

Minimum-stay requirements vary by property, location, season, and travel dates. Some rentals allow shorter stays, while others require seven nights, 28 nights, or longer. Guests planning an extended trip can also browse Florida Keys weekly rentals and Florida Keys monthly rentals.

How do I narrow down the Florida Keys vacation rentals?

Start by entering your arrival and departure dates, then use the available filters to narrow rentals by location, bedrooms, bathrooms, property type, and amenities such as boat docks, pools, ocean views, parking, and pet-friendly accommodations.

Can I search Florida Keys vacation rentals by destination?

Yes. You can browse rentals by destination, including Key Largo, Islamorada, the Middle Keys, the Lower Keys, and Key West.