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Florida Keys vacation rentals

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Top-rated vacation rentals in Florida Keys

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Condo in Key Colony Beach
Keys Breeze Ocean View Condo & Pool - Key Colony
Gorgeous Florida Keys studio condo in Key Colony Beach with beautiful ocean front location. The condo features all new furniture and furnishings with a crisp, modern interior and kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Condo has one king-sized bed and sleeps 2 people. We just finished a full bathroom remodel adding all new walk-in shower, tile, vanity, etc. This condo is simply exquisite!
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Home in Marathon
Oceanfront Tiny Villa in the Heart of the FL Keys
Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!
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Rental unit in Key West
At Mine | Key West Suite steps from Duval Street
Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, hangers, TV, and A/C. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Florida Keys beach vacation rentals

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Home in Marathon
Oceanview Oasis! Porch & Theater
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Rental unit in Key Largo
Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi
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Home in Key Largo
Little Cottage on an island
Rental unit in Key West
Leo's Lodge by Brightwild | Studio w/Kitchenette
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Condo in Key Colony Beach
Coastal Keys Condo, Oceanfront Complex Sleeps 4
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Condo in Marathon
Tiki Bar, Resort Pool, Marina, Pickleball, Beach!
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Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
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Condo in Tavernier
It's Tiki Time in the Keys! Mid-Mod 1 Br/1Ba
Condo in Key West
Sky Loft by Brightwild | Penthouse in Prime Spot!
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Tiny home in Key Largo
Relax by the sea & No cleaning fee !
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Rental unit in Key West
Key West - Sunrise ❀ The Green House
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Hotel room in Key West
Speakeasy Inn - Room 1A (1 Queen Bed & 1 Single)

Private Florida Keys vacation rentals

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Rental unit in Key West
At Mine | Elegant Suite steps from Duval Street
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Rental unit in Key West
Key West - Sunset ❀ The Green House
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Rental unit in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
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Rental unit in Key West
Curry House by Brightwild | Balcony & Pool - Rm #2
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Condo in Key Colony Beach
Beachside Unit 36 Private Patio & Beach Plus Pool
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Condo in Tavernier
SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
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Rental unit in Key Largo
Waterfront Studio 2| Couples Oasis | Kayaks | Pool
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Vacation home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
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Condo in Key Colony Beach
Key Colony Beach Luxury Condo, New Modern Interior
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Condo in Key Colony Beach
Steps to the Beach Condo Key Colony Beach Sleeps 4
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Home in Marathon
No Name Cottage
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Condo in Marathon
Tropical Paradise ~ The Reef Marathon, 2BR Villa!
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Florida Keys fishing vacation rentals

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Tiny home in Key Largo
Oasis2 in Key Largo With a million dollar view
Home in Marathon
Grouper Getaway @ Ocean Isles Fishing Village
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Guesthouse in Key Largo
Bayside Cabin beach romantic sunsets & fishing.
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Rental unit in Key Largo
2/1 Oceanfront Apartment with Dockage
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Home in Marathon
Sombrero Beach house w/45’ dock Ocean access
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Home in Key Largo
Oceanside Kawama Villa R5
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Guest suite in Marathon
CANAL, Dock Waterfront, HOT-Tub, Kayak and E Bike!
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Rental unit in Key Largo
Overlooking Marina/Ocean view & FREE GOLF CART
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Condo in Key Largo
Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike
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Home in Marathon
Coconut Palms in Marathon
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Home in Key Largo
5 O'clock Somewhere - Key Largo
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Tiny home in Key Largo
Delightful Waterfront Tiny Home

Your guide to Florida Keys

All About The Florida Keys

From vibrant Key West to the mysteriously named No Name Key, the Florida Keys offer historical intrigue and geographical wonder in a graceful archipelago, stretching out from the Everglades towards Havana. Postcard-worthy turquoise waters make the Keys a popular destination for sports fishing, scuba diving, and boating. If you fancy a more leisurely set of activities during your visit, boat rides in the tropical sun and snorkeling let you set your own pace for exploring the dazzling coral islands.

The strong culinary culture of the Keys is centered around fresh seafood, from mahi-mahi to snapper to blackfin tuna, alongside other edible delights, like Key lime pie on a stick. For those wanting to explore both land and sea, consider venturing into the Mel Fisher Maritime Heritage Museum or the Key West Shipwreck Treasure Museum, both of which are excellent forays into the impact the ocean has had on the history of these islands.


The best time to stay in a vacation rental in Florida Keys

The best time to look for Florida Keys vacation rentals is between March and May. There are typically fewer crowds during this time and the weather is still warm without being humid, unlike in the muggier summer months.. The islands also host a variety of events in the spring. The 7 Mile Bridge Run in April is an annual marathon spanning the entirety of one of the island’s bridges. The Taste of Key West, also in April, is an annual celebration of the various cuisines that call the archipelago home, and feature everything from fine dining to seafood shacks and food trucks. The Key West Songwriters’ Festival in May has been going strong for 25 years and features dozens of performers across genres such as country, reggae, and rock.


Top things to do in Florida Keys

Duval Street

Duval Street, running from Mallory Square to the Southernmost Point marker, is one of Key West’s most lively streets. Host to museums, shops, galleries, and cafes, Duval Street is great not only for people-watching, with its many annual parades and events, but also for learning about the history of the Florida Keys, with attractions such as the Ernest Hemingway Home and Museum, and the former Strand Theater.

Dry Tortugas National Park

Dry Tortugas National Park, 70 miles from Key West, is only accessible by boat or plane, but is a worthwhile stop on any trip to the Florida Keys. An archipelago of seven beach-ringed islands, one is taken up entirely by the preserved ruins of Fort Jefferson, which stands guard over the coral, seagrass, and shipwrecks that welcome snorkelers from around the world. Popular snorkeling spots are the Historic Coaling Pier, Fort Jefferson's moat wall, and Garden Key. Boaters can explore around Loggerhead Key's Little Africa Reef and the Windjammer Wreck.

Marathon

Not to be confused with the activity, or the location of the same name in Greece, Marathon is the sportfishing center of the Florida Keys. Charters are easily arranged here for deep-sea, reef, and flats fishing. A variety of beaches and beachfront restaurants line the strip, while the former Seven Mile Bridge on the island makes a scenic path for walkers, joggers, and cyclists.

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