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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.

Condo in Key Colony Beach
Steps to the Beach Condo Key Colony Beach Sleeps 4
Newly renovated condo in Key Colony Beach ocean front complex with heated pool and private beach. Unit #16 is a studio condo with crisp interior (impeccably clean) featuring tropical decor and kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach just steps away with lounge chairs, patio tables, tiki's and BBQ grills for guest use.
$210 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!
$235 per night
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Condo in Key Colony Beach
Beachside Unit 27 - The Beach is Calling You!
Unit 27 Details: Main Floor, Walk-in shower, King Bed plus a Queen Pull-Out Sofa, Maximum Occupancy 3-4 Guests, Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.” Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean.
$181 per night
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Florida Keys beach vacation rentals

Condo in Marathon
Tropical Paradise
$211 per night
Guest suite in Marathon
Dolphin Drive
$163 per night
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Condo in Key Colony Beach
Amazing Ocean Front Views, Sleeps 4 Key Colony Bch
$298 per night
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Condo in Key Colony Beach
Beachside Unit 32 - Pool & Private Beach Sleeps 4
$215 per night
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Home in Key Colony Beach
Turtle-By-The-Sea: the Best Deal in KCB!
$184 per night
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Condo in Marathon
Waterfront, Marina, pool, tiki bar, boat ramp
$182 per night
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Rental unit in Key West
Key Lime Cottage - Free Parking, Steps to Duval St
$223 per night
Rental unit in Key West
Leo's Lodge - Cozy Efficiency at Galleria #7
$142 per night
Townhouse in Key West
Poolside Cottage #412
$185 per night
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Home in Marathon
Beach House, Private Pool & Dock, Gulf Sunset view
$445 per night
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Rental unit in Key West
Banana Split - Pool, Parking & Private Balcony!
$281 per night
Serviced apartment in Marathon
Knight's Key Suites Premium Apartment w/Kitchen
$220 per night
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Weekend vacation rentals in Florida Keys

Cottage in Islamorada
FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
$156 per night
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Condo in Key Colony Beach
Beachside Unit 34- Pool, Private Beach and Tiki's!
$215 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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Townhouse in Key West
Poolside Cottage #411
$180 per night
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Rental unit in Marathon
Beachfront Condo w/ Ocean Views in Marathon
$275 per night
Rental unit in Key West
Cozy upstairs apartment with pool #3
$250 per night
Condo in Tavernier
Condo in the Keys, Peaceful ocean view retreat!
$155 per night
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Condo in Key Colony Beach
Poolside 2 Bdrm in Oceanfront Complex, sleeps 6
$350 per night
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Vacation home in Key Largo
Key Largo's Best Kept Secret | Oceanfront Cabanas
$186 per night
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Home in Marathon
P30 - 1200 30th
$436 per night
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Condo in Key West
The Island Suite @ KW vacation
$247 per night
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Rental unit in Islamorada
A blissful boho studio in the FL Keys
$106 per night
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Florida Keys winter vacation rentals

Condo in Key Colony Beach
Anchors Away Condo, Key Colony Oceanfront Sleeps 4
$235 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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Condo in Marathon
Waterfront Marina Pool Tiki Bar Boat Ramp Sleeps 4
$209 per night
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Rental unit in Key West
Royal Palm- 1 Block to Duval with Grill & Hot Tub!
$261 per night
Condo in Key Colony Beach
Beachside Unit 01 - Property on Atlantic Ocean
$215 per night
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Rental unit in Key Largo
Waterfront Studio 2| Couples Oasis | Kayaks | Pool
$209 per night
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Rental unit in Key West
At Mine | Lovely Suite steps from Duval Street
$199 per night
Loft in Marathon
Cabana Club Suite: Key Colony Beach, Florida Keys
$189 per night
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Vacation home in Marathon
Cabana Club Condo: Key Colony Beach, FL
$399 per night
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Private room in Marathon
Casa Mariposa: Easy walk to Sombrero Beach
$189 per night
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Condo in Marathon
Pool, Tiki Bar, Marina & more!
$216 per night
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Condo in Marathon
Marathon 1BR Villa on Beautiful Resort w/Amenities
$305 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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