Florida Keys Vacation Rentals

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15 miles south of Miami you will discover the beautiful Florida Keys; 126 miles of islands stretching to our southernmost point of the Continental United States. Just 90 miles from Cuba, the Keys can feel like a foreign destination hidden in our backyard. In total there are over 1,700 individual islands making up the keys, however, most are uninhabited and only 43 are connected via bridges. When thinking about Flordia Keys vacation rentals think about visiting Key West for the obvious nightlife and restaurants or some of the lesser known islands such as Marathon, Islamorada or Key Largo. The main chain of islands is connected by the Overseas Highway which is a 127 mile stretch of U.S. 1 and includes the famous seven-mile bridge.

 

Things To Do

Key West

For those looking for the best nightlife and culture, Key West is a must. Perfect for birthdays, family vacations and of course bachelor and bachelorette parties. It is a great mix of history, cultural diversity, architecture and natural beauty. Key West has played home to Ernest Hemingway, Tennessee Williams, and of course Jimmy Buffet, who we can thank for dubbing it “Margaritaville.” The tin-roofed houses and mini mansions get their roots from the Bahamian and Cuban heritage that influences the island. Take in the sunset with a nightly celebration at Mallory Square, sip on frozen drinks from one of the many festive bars on Duval Street, visit the Hemingway House and its famous six-toed cats, or venture all the way down to the Southernmost point for an iconic picture. Off the beaten path is the Cuban Coffee Queen, a tiny Cuban coffee shop known to the locals with the best coffee and breakfast sandwiches anywhere on the island. No matter how you choose to spend your time in Key West it is sure to memorable and unlike any other.

 

Other great Key West activities:

Day trip to the Dry Tortugas

Parasailing or snorkeling trip

Harry S Truman Little White House

 

Must try Key West restaurants/nightlife:

Blue Heaven (outstanding Brunch)

Hot Tin Roof

Sloppy Joes Bar

Captain Tony’s Saloon

La-Te-Da (famous for cabaret, not for the faint of heart)

Islamorada

Made up of 6 islands, Islamorada is situated between the waters of the Everglades and the waters of the Florida Strait. It is a fisherman’s dream with a high demand for deep sea fishing charters and saltwater fly fishing. You could be lucky to catch a Sailfish offshore and then hunt for Tarpon and Snook in the backcountry in the same day. Islamorada is not just for fisherman, the Theater of the Sea and the History of Diving museum will delight the whole family. You can even hand feed tarpon off the dock of Robbie’s Marina while you wait for a table at the Hungry Tarpon.

Key Largo

The northernmost key and closest to solid ground is Key Largo. Home to a national park and two state parks, it has some of the best wildlife and botanical scenery in Florida. The Humphrey Bogart Film Festival calls Key Largo home each year to play tribute to the great legend. Whether you book a dolphin encounter program or go bird watching in the Everglades, Key Largo is definitely a place for nature lovers. The island also is home to an underwater hotel located in the lagoon of the Key Largo Undersea Park.

Marathon

Primarily comprised of three main islands, visitors like to enjoy the “old keys” lifestyle in Marathon which is home to some of the best accommodations the keys has to offer. It has some of the best eco-attractions including wreck and reef diving, The Turtle Hospital and the Dolphin Research Center. Just off the coast is the tiny island of Pigeon Key where visitors can experience going back in time to where the workers who built the Over-Sea Railroad lived.

 

Where to Stay

Booking a private vacation home in the Florida Keys is the best way to experience the authenticity of the islands. It forces you to immerse into the local culture more and experience the different restaurants, bars and activities they have to offer. Browse from hundreds of vacation rentals in the Keys and let us help you find the perfect vacation home.

 

Weather

March is by far the best month! But peak season is January to May with amazing warm weather and low humidity, plus it will be colder almost everywhere else in the country. The amazing weather can, however, make things very busy and very expensive. So if you don’t mind a little heat and humidity, visiting during the off season (June to December) can save you a pretty penny. September is the wettest month with an average of 6 inches of rain.

Wherever you are right now, you can almost be certain the weather is better in the Keys. The Keys have a year round average temperature of 86 degrees and plenty of sunshine with average water temperatures in the mid-80s.

 

MonthHighLow
January
75
65
February
75
66
March
79
69
April
82
72
May
85
76
June
88
79
July
89
80
August
89
79
September
88
79
October
84
76
November
80
71
December
76
67

8 vacation rentals

  • A Sunshine 4A

    Newly Remodeled Kitchen and Bathrooms and New A/C2 Bedroom / 2 Bath1 King, 2 Twins & Sofa Sleeper3 TV'sFREE WiFiFree Calling to US & CanadaGulf...

    2 Bedroom / 2 Bathroom
    Sleeps 6

    $21.59 - $37.86
    per night
  • Sea Club #50

    2 Bedroom /2 BathQueen, Double and a TwinFREE Wi-Fi50", 47", 19" LCD TV'sWashers & DryersBalcony20 foot x 50 foot Heated PoolFishing pier and ...

    2 Bedroom / 2 Bathroom
    Sleeps 5

    $19.01 - $28.41
    per night
  • Chateaux 101

    1 Bedroom / 1 BathKing bedFREE Wi-Fi Broadband Internet access*Free calling to US & Canada2 Recliners in living roomLarge balcony, direct Gulf...

    1 Bedroom / 1 Bathroom
    Sleeps 2

    $20.98 - $32.76
    per night
  • Chateaux 204

    1 Bedroom / 1 BathKing and 2 Queen Sleeper SofasLarge balcony, direct Gulf frontFree Wi-FiFree Calling to US and CanadaComplex Washers & Dryers...

    1 Bedroom / 1 Bathroom
    Sleeps 6

    $17.98 - $31.31
    per night
  • Chateaux 205

    1 Bedroom / 1 BathKing and Queen sofa sleeperLarge balcony, direct Gulf frontFREE Wi-Fi InternetFREE Local callingComplex Washers & DryersNon...

    1 Bedroom / 1 Bathroom
    Sleeps 4

    $20.98 - $32.76
    per night
  • Chateaux 301

    1 Bedroom / 1 Bath1 King BedLarge corner balcony (46 feet long), direct Gulf frontFREE Wi-FiFREE Calling to US & CanadaComplex Washers & Dryers...

    1 Bedroom / 1 Bathroom
    Sleeps 2

    $20.98 - $32.76
    per night
  • Tahitian Towers 203

    1 Bedroom / 1 Bath1 Queen*FREE Wi-FiLarge balcony, wonderful Gulf viewLocated in Indian ShoresNon Smoking, No PetsPool Not Heated*** One mon...

    1 Bedroom / 1 Bathroom
    Sleeps 2

    $9.46 - $15.48
    per night
  • Tahitian Towers 303

    1 Bedroom / 1 Bath1 QueenNewly Remodeled*FREE Wi-FiLarge balcony, wonderful Gulf viewLocated in Indian ShoresNon Smoking, No PetsPool Not He...

    1 Bedroom / 1 Bathroom
    Sleeps 2

    $10.48 - $21.71
    per night