Roosevelt Cottage 5 BD 4 BR

Roosevelt Cottage - Captiva Vacation Rentals.

Roosevelt Cottage – Captiva Vacation Rentals!

Captiva Vacation Rentals: Roosevelt Cottage – Lovely direct bay front home with private heated pool and boat dock.

Easy walk down the drive to the private beach across Captiva Drive. Our home has many updates and features that set it apart from others including custom furnishings and finishes.

The main part of the house features a main level master bedroom suite with a king bed, TV and en-suite bathroom with claw foot tub, shower and walk in closet. You can see wonderful views of the Roosevelt Channel from the large doors and attached lanai. The main level of the home also features a private office, half bathroom, sitting area, den, full kitchen, dining room and laundry area with two sets of stack washer/dryers.

Go upstairs where we have a spacious loft area with seating, wet bar and a flat panel TV. There is a guest bedroom on each side of the loft both with queen sized beds and a full bathroom in between.

Attached by the deck, but just outside the main house is a separate guest suite with a king bed, living room sitting area, dining table, compact kitchen, full bathroom and washer/dryer.

For additional guests, there is another guest suite above the garage (stairs) complete with a king sized bed, full bathroom and seating.

Roosevelt Cottage has plenty of space with nearly 5,000 sq ft of space combined.

Please note that the entire property consists of 3 residences, two of which are occupied by the owner and property manager.

We offer a separate dock for the Roosevelt Cottage, however, the owner may use the private dock which is not available for guest use.

Roosevelt Cottage can accommodate up to 10 guests and may rent for one week or longer.

Pets not allowed.

Roosevelt Cottage: Bay View

Roosevelt Cottage Location: Captiva Island

Roosevelt Cottage: House

Please click here for more information and booking Roosevelt Cottage.


Captiva Island: Background, History, Hurricanes & Rise As A Quiet Sport Fishing & Family-oriented Vacation Island. Roosevelt Cottage & Many More Captiva Vacation Rentals.

“Where ‘somebuddies’ go to be ‘nobuddies.'”
Roosevelt Cottage - Captiva Vacation Rentals.
Roosevelt Cottage – Captiva Vacation Rentals.

“Captiva Island is an island in Lee County in southwest Florida, located just offshore in the Gulf of Mexico. Captiva Island is just north of Sanibel Island.

The Wall Street Journal selected Sanibel and Captiva Islands as one of the 10 Best Places for Second Homes in 2010.[6]

Captiva was the full-time home of artist Robert Rauschenberg. His home still stands there.

Roy Lichtenstein, the American pop artist, also had a home on Captiva.”


“According to local folklore, Captiva got its name because the pirate captain José Gaspar (Gasparilla) held his female prisoners on the island for ransom (or worse). However, the

Captiva Vacation Rentals: Teddy Roosevelt On Boat In Captiva, Courtesy Of Captiva Historical Society.
Captiva Vacation Rentals: Teddy Roosevelt On Boat In Captiva, Courtesy Of Captiva Historical Society.

supposed existence of José Gaspar is sourced from an advertising brochure of an early 20th-century developer and may be a fabrication.

Around 3000 B.C., the sands of Captiva started to erode, resulting in the eventual formation of Sanibel Island. The Gulf of Mexico waters were eight feet lower than they are today. It is said that the first inhabitants of Captiva were The Calusa Indians.[1] The population of the Calusa is believed to have reached as many as 50,000 people. “Calusa” means “fierce people”, and they were described as a war-like people. The Calusa Indians were resistant to colonization and attacked any explorers who came into their territory. Calusa Indians built their houses on stilts without walls. They wove palmetto leaves together to build roves (twisted strands of fibers). The Calusa Indians fished for food on the coast, bays, rivers, and waterways. They did not farm. “The men and boys of the tribe made nets from palm tree webbing to catch mullet, pinfish, pigfish, and catfish. They used spears to catch eels and turtles. They made fish bone arrowheads to hunt for animals such as deer. The women and children learned to catch shellfish like conchs, crabs, clams, lobsters, and oysters.”[citation needed] The Calusa Indians used the shells on the island for utensils, jewelry, tools, weapons, and ornaments.

By the late 1700s, most of the Calusa Indians had died out. Many were captured and sold as slaves while others died from diseases such as smallpox and measles.

An Austrian named Binder (b. 1850) was on a German freighter headed to New Orleans when the ship crashed and he was shipwrecked off Boca Grande. He then washed up to shore on what has been since 1921, Upper Captiva. “He lived for several weeks on what the unoccupied

Captiva Vacation Rentals: Teddy Roosevelt, Captiva Island, At Snyder Outdoor School for Boys, Courtesy Of Captiva Island Historical Society.
Captiva Vacation Rentals: Teddy Roosevelt, Captiva Island, At Snyder Outdoor School for Boys, Courtesy Of Captiva Island Historical Society.

island had to offer, built a makeshift raft, and got himself to Pine Island, where he was helped to return to his home. By 1888, due to his having fought with the U.S. Army, he became naturalized and was allowed to homestead on Captiva in 1888, when he was 38 years old. For 10 years he was Captiva’s first and only inhabitant. He died in 1932.” [2]


“Originally part of neighboring Sanibel Island to the southeast, it was severed in 1926 when a hurricane‘s storm surge created a new channel, Blind Pass. The channel filled in over subsequent years but was reopened by dredging in the summer of 2009. Like Sanibel, Captiva is a barrier island to Pine Island (to the east of Captiva and north of Sanibel), however, it is much narrower. The only automobile access to Captiva is via the Sanibel Causeway and Sanibel-Captiva Road, which ends in the CDP of Captiva, the island’s only CDP. Captiva was homesteaded in 1888 and a tiny cemetery next to The Chapel by the Sea has the grave of the original resident, William Herbert Binder (1850–1932), an Austrian. Half the island is in private ownership, with “Millionaire’s Row”, luxury homes on gulf and bay side of Captiva Drive. The South Seas Island Resort entry gate is at the end of this road. Roosevelt Channel on the east side of the island is named for Theodore Roosevelt who fished there.

North Captiva Island or Upper Captiva is another island, in turn, severed from Captiva in a 1921 hurricane, creating Redfish Pass. North Captiva has power from lines that originate on the north end of Captiva and is privately owned. With about 300 homes built and 300 vacant lots, the island is about halfway to build-out. Since the island can be accessed by boat or small plane only, North Captiva real estate values are generally lower than on Captiva.”

Captiva Vacation Rentals: Hurricane Charley, August 2004

Photos & video here.

“Captiva was seriously damaged in August 2004 when the eastern eyewall of Hurricane Charley struck North Captiva, immediately before hitting Charlotte Harbor to the north-northeast.

Captiva Vacation Rentals: Manatees, Captiva Island, December 2017.
Captiva Vacation Rentals: Manatees, Captiva Island, December 2017.

Initial reports indicated that 160 buildings were destroyed and another 160 seriously damaged. Reports indicate that the storm surge cut a path 491 yards (449 m) wide across the narrowest part of North Captiva, separating the island. The separation of the two halves of the island began three years earlier during a series of tornadoes caused by Tropical Storm Gabrielle that passed through the area in September 2001.[3]

The new pass filled in within a few years and is now back to its pre-Charley state. Most of the invasive Australian pines on the island blew over in the hurricane, making room for native mangroves and sabal palms.”

Captiva Vacation Rentals: Hurricane Irma, September 2017

Captiva Island escaped Hurricane Irma largely unscathed.

There was some tree damage and a lot of foliage cleanup post the storm, but the storm shifted

Captiva Vacation Rentals: Snook A Smile, Captiva Island, November 2017.
Captiva Vacation Rentals: Snook A Smile, Captiva Island, November 2017.

east after Hurricane Irma’s “second landfall was made, as a Category 3 hurricane, at Marco Island at 3:35 pm. EDT [on September 10, 2017].[239]

A 7 ft (2.1 m) storm surge occurred in Naples, which Irma passed over as a Category 2 hurricane after being downgraded at 5 pm. EDT.[240][241][242]

Part of Tampa Bay (at Hillsborough Bay) was drained in a reverse storm surge caused by strong offshore winds, prior to the arrival of the eye of the hurricane.[243]

Sarasota Bay was also drained, resulting in the stranding of two manatees which were then rescued.[244][245] The hurricane was downgraded to Category 1, prior to reaching Tampa.[246]”

More background here.

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