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.

Condo in Marathon
Tropical Paradise
Completed remodeled 1/1 condo in the Keys. Centrally located in the heart of Marathon. Minutes from Sombrero beach via car, 10 minute golf cart/bicycle ride. Boat slip on premises for a small fee. When booking, you can call the doc master for a slip( $2 a ft). Fully furnished and full working kitchen. Tiki bar, restaurant, and pool on premises. Publix, local stores, and Cranes Point are 1 minute down the road. Turtle Hospital, restaurants, and other tourist attractions are in close proximity.
$143 per night
Condo in Key Colony Beach
Coastal Keys Condo, Oceanfront Complex Sleeps 4
Lovely coastal Keys studio condo in Key Colony Beach oceanfront complex with heated pool and private beach. Unit #17 has new beds with memory foam mattress toppers and renovated kitchen with granite countertops stocked with everything needed to cook a complete meal (dishes, cookware, appliances and of course blender, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.
$220 per night
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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!
$255 per night
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Florida Keys house rentals

Home in Key Largo
Little Cottage on an island
$115 per night
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Home in Marathon
Waterfront Private Home w/Pool-Family&Pet Friendly
$535 per night
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Home in Marathon
Private waterfront sleeps 8 dock heated pool pets
$251 per night
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Home in Marathon
Clara`s Ocean Gem Condo 2bed 2bath third floor wit
$147 per night
Home in Marathon
P30 - 1200 30th
$436 per night
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Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
$378 per night
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Home in Marathon
Beach House, Private Pool & Dock, Gulf Sunset view
$406 per night
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Home in Marathon
Direct Oceanfront Private Paradise - Pool/Spa/Dock
$770 per night
Home in Marathon
Blue Chair Haven, Sombrero beach area, canal, pool
$403 per night
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Home in Marathon
Oceanfront Tiny Villa in the Heart of the FL Keys
$293 per night
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Home in Marathon
Searenity Vacation Rental! Pool, Tiki Hut, Dockage
$365 per night
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Home in Islamorada
Waterfront, Location, Private, Dock, Pool, Charm.
$730 per night

Florida Keys beach vacation rentals

Condo in Key Colony Beach
Beachside Unit 27 - The Beach is Calling You!
$208 per night
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Condo in Key Colony Beach
Amazing Ocean Front Views, Sleeps 4 Key Colony Bch
$254 per night
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Condo in Key Colony Beach
Beachside Unit 12- Pool, Private Beach & Tiki Huts
$253 per night
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Rental unit in Marathon
Beachfront Condo w/ Ocean Views in Marathon
$284 per night
Rental unit in Key West
At Mine | Lovely Suite steps from Duval Street
$165 per night
Condo in Marathon
Waterfront, Marina, pool, tiki bar, boat ramp
$196 per night
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Serviced apartment in Marathon
Knight's Key Suites Premium Apartment w/Kitchen
$230 per night
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Guest suite in Marathon
Dolphin Drive
$175 per night
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Rental unit in Key West
Banana Split - Pool, Parking & Private Balcony!
$271 per night
Condo in Key Colony Beach
Poolside 2 Bdrm in Oceanfront Complex, sleeps 6
$337 per night
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Rental unit in Key West
Creme Brulee Suite- 1 Block To Duval & Shared Pool
$217 per night
Rental unit in Key West
Royal Palm- 1 Block to Duval with Grill & Hot Tub!
$278 per night

Florida Keys winter vacation rentals

Condo in Key West
Salt Cay Suite - Pet Friendly, Modern Condo!
$294 per night
Condo in Key Colony Beach
Exquisite Luxury Oceanfront Complex, Sleeps 4
$236 per night
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Condo in Key Colony Beach
Beachside Unit 39 Tiki Huts, Private Beach & Pool
$253 per night
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Condo in Key Colony Beach
Beachside Unit 28 - Private Beach, Pool & Paradise
$253 per night
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Rental unit in Key West
Curry House- Balcony & Pool, Room #2
$199 per night
Condo in Marathon
WATER FRONT 1bed/1bath, pool, tiki bar, boat ramp
$220 per night
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Rental unit in Key West
Cozy and fully equipped Apartment with pool #1
$214 per night
Cottage in Islamorada
FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
$171 per night
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Serviced apartment in Marathon
Knight's Key Suites Deluxe Double w/Kitchen
$151 per night
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Condo in Tavernier
Condo in the Keys, Peaceful ocean view retreat!
$145 per night
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Rental unit in Key Largo
Waterfront Studio 2| Couples Oasis | Kayaks | Pool
$206 per night
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Private room in Marathon
Casa Mariposa: Easy walk to Sombrero Beach
$189 per night
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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.


When is 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.


What are the 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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