Florida Keys Vacation Rentals

Compare 299 vacation rentals.
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USA > Florida > Florida Keys

Make Florida Keys your next getaway

Escape to island time in the Florida Keys. From Key Largo to Key West, the Florida Keys offer a one-of-a-kind tropical getaway where life moves a little slower, the sunsets are a little brighter, and the ocean is always calling. Whether you’re craving an adventure-filled trip or a serene beachside retreat, our Florida Keys vacation rentals provide the perfect home base for exploring this island paradise.

Explore Florida Keys house rentals, condo rentals, duplexes, and more

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House rentals

View 150 House rentals
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Condo rentals

View 70 Condo rentals
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Duplexes

View 35 Duplexes

Popular amenities for Florida Keys vacation rentals

Popular
Dog-friendly Hot tub Internet
Sunrise Suites - Cozumel Suite 112
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Cozumel Suite 112 - Key West, FL

$343 avg / night
4.31 (121)
Sunrise Suites - Antigua Suite 312
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Antigua Suite 312 - Key West, FL

$363 avg / night
4.49 (111)
Old Town Garden Villas - Abaco Suite
1 Bedroom | 1.5 Bath | Sleeps 4

Old Town Garden Villas - Abaco Suite - Key West, FL

$527 avg / night
4.71 (119)
Atlantic Ocean View
2 Bedroom | 2 Bath | Sleeps 6

Atlantic Ocean View - Key West, FL

$575 avg / night
4.18 (92)
Conch Casa
2 Bedroom | 1 Bath | Sleeps 6

Conch Casa - Key West, FL

$597 avg / night
4.51 (122)

View 294 more homes

Browse more vacation rental amenities in Florida Keys

Pool | Electric vehicle charger | Lake view | Ocean view | Oceanfront | Riverfront | Sound view | Soundfront | Water view | Waterfront

Recent Florida Keys guest reviews

We loved the nautical theme and the overall vibe of the house. We wish from the house porches the view was better but a short little walk within the neighborhood the sunsets were great.
Rob M. | Apr 2025
Easy to walk to most things you likely want to do, but still back in the neighborhoods at bit, so it's pretty quiet at night. The photos are accurate and the property is taken care of nicely. Definitely would stay here again.
Daniel K. | Apr 2025
The peaceful view and great home
Andres P. | Apr 2025
Florida Keys vacation rental FAQ

Yes, 112 of our Florida Keys homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 298 of our Florida Keys vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Florida Keys vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Florida Keys team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Florida Keys, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Why vacation in the Florida Keys?

Unbeatable water adventures

Snorkel the only living coral reef in the continental U.S., go deep-sea fishing, or kayak through mangrove tunnels.

Iconic island vibes

Stroll the colorful streets of Key West, sip a rum runner in Islamorada, or enjoy fresh seafood at a dockside restaurant.

Endless sunshine

With warm temps year-round, there’s never a bad time to visit.

World-ramous sunsets

Gather for the nightly sunset celebration at Mallory Square or enjoy a quiet moment on your private balcony.

From oceanfront condos and private homes with docks to luxurious retreats with pools, find your perfect Florida Keys vacation rental with Vacasa.

Does Vacasa offer snowbird or long-term rentals in the Florida Keys?

Live like Ernest Hemingway. Like our weekly rentals, we offer a variety of different snowbird rentals in the Florida Keys to choose from, including beachfront cottages surrounded by palm trees, places to stay near The Key West Butterfly and Nature Conservatory, homes with private pools, pet-friendly rentals in Florida, and so much more.

Florida Keys travel inspiration

The ultimate escape: Key West cottages with private pools Best places to stay in the Florida keys for snorkeling 4 scenic Florida Keys races and marathons for every skill level

Nearby destinations

Gulf Coast   |   Florida's Atlantic Coast   |   South Florida   |   Southeast Florida   |   Everglades National Park   |   Middle Keys, FL   |   Lower Keys, FL   |   Old Town Key West   |   Mallory Square - Key West   |   Bahama Village - Key West   |   Historic Key West   |   Coco Plum Beach - Marathon   |   Fat Deer Key - Key Colony Beach   |   Biscayne National Park   |   Upper Keys, FL   |   Sunrise Suites Resort - Key West   |   Papa's Hideaway - Key West, FL   |   Stock Island   |   Shipyard Condos - Key West   |   Skipjack Resort & Marina - Marathon, FL   |   Saddlebunch Keys   |   Duval Square - Key West   |   Tropical Village - Key West   |   Palm Gardens - Key West, FL   |   Little Torch Key   |   Islamorada   |   Big Pine Key   |   Key Largo   |   Marathon   |   Duck Key   |   Key West   |   Sugarloaf Key   |   Tavernier   |   Long Key   |   Summerland Key   |   Cudjoe Key   |   Key Colony Beach   |   Conch Key   |   Florida
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