Happy Days Key West

vacation Paradise

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Rates From $99/night

Dates: December – April

Rates From $79/night 

Dates: April – December

Key West Hotel Maps

Off-Season Map >>>
April-Dec. $79 – $185

Season Map >>>
Dec.-April $99 – $370

Key West

Welcome to Happy Days Key West. This site offers the best deals on Key West Hotels and resorts available for seasonal dates. We list accommodations by price during the busiest and slowest times of the year. The phone numbers to the hotels are provided so that you can book directly and get the best rates. From the cheapest to the most expensive in a convenient list depending on when you plan to vacation.

Key West is the southernmost point of the Florida Keys in Monroe County, Florida. Located 129 miles (3 hour drive) south of Miami, and 90 miles north of Cuba. The island is a very popular destination for cruise ships to stop as they travel through the Caribbean. You can fly directly into the Key West airport from Miami. It’s a short flight that only takes about 30 minutes.

Downtown (Oldtown) is the area surrounding the main street named Duval Street, and includes much of the southwest corner of the island. The island is only two by four miles. The remaining part of the island (Newtown) is mainly residential with a few hotels and resorts along the ocean front and beach. Many visitors consider the southernmost beach (south beach), to be the best beach on the island. It’s surrounded by luxury resorts and has a cafe with spectacular ocean views. As a guest of one of the resorts you can get a complimentary beach chair and have cocktails delivered while you bask in the sun.

The official island motto is “One Human Family.” Key West Fl was relatively isolated until 1912 when it was connected to the Florida mainland via the Overseas Railway. The dream of Henry Flagler was to bring people to the American Caribbean for vacation and sun. One of the most famous residents, there is a museum dedicated to Flagler and his railroad located downtown. There are still many spans of old rail crossings throughout the Keys you’ll see as you drive down. Completed in 1938, the US Government rebuilt the rail lines as a highway, which is now US 1 / the Overseas Highway. In 1939 Franklin Roosevelt toured the road and the island for the first time. He loved Key West and the first road you turn onto is named after him. The Conch Republic is a nick-name applied to the city. It was first used during a mock protest secession of the Keys from the United States on April 23, 1982. The term continues to be used as a tourism slogan, and is even part of the official flag. Key West celebrates Conch Republic Independence Day every April 23 as part of a week-long festival of activities involving numerous businesses in the city.

The most popular festival of the year (which there are many) is at the end of October, called Fantasy Fest. The theme is different every year and the finally is an all-night street party that begins with a parade. Key West is the only city in the lower 48 states never to have had a frost. Because of the proximity of the Gulf Stream in the Straits of Florida, about 12 miles south and southeast, and the tempering effects of the Gulf of Mexico to the west and north, Key West Fl has a notably mild, tropical climate. The main high season for vacation rentals and tourism is from December to April. The island is packed with vacationers escaping the snow and cold up north. Because the island so small, we recommend making advanced reservations whether you come during season or off season.

The official island motto is “One Human Family.” Key West Fl was relatively isolated until 1912 when it was connected to the Florida mainland via the Overseas Railway. The dream of Henry Flagler to bring people to the American Caribbean for vacation and sun. One of the most famous residents, there is a museum dedicated to Flagler and his railroad located downtown. There are still many spans of old rail crossing through the Keys you can see as you drive down. Completed in 1938, the US Government rebuilt the rail lines as a highway, which is now US 1 / the Overseas Highway. In 1939 Franklin Roosevelt toured the road and the island for the first time. He loved Key West and the first road you turn onto is named after him. The Conch Republic is a nick-name applied to the city. It was first used during a mock protest secession of the Keys from the United States on April 23, 1982. The term continues to be used as a tourism slogan, and has been used in Key West television commercials and is part of the official flag. Key West celebrates Conch Republic Independence Day every April 23 as part of a week-long festival of activities involving numerous businesses in the city. The original protest event was motivated by a U.S. Border Patrol roadblock and checkpoint which greatly inconvenienced residents and was detrimental to tourism in the area. Tourism was, and is today the number one source of income for local residents. The most popular festival of the year (which there are many) is at the end of October, called Fantasy Fest. The theme is different every year and the finally is an all night street party that begins with a parade. Key West is the only city in the lower 48 states never to have had a frost. Because of the proximity of the Gulf Stream in the Straits of Florida, about 12 miles south and southeast, and the tempering effects of the Gulf of Mexico to the west and north, Key West Fl has a notably mild, tropical climate. The main high season for vacation rentals and tourism is from December to April. The island is packed with vacationers escaping the snow and cold up north. Because the island so small, we recommend making advanced reservations whether you come during season or off season.

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