10 Incomparable Island Locations to Explore (Southwest Florida's Best)

Bookelia Island

History abounds on this special island, considered the Tarpon fishing capital of the world. Charlotte Harbor is also within vicinity and just a few moments away. Several cottage style listings freshly updated and remodeled making it iconic.

All Active and Currently Available Bookelia Island MLS Listings (124 Properties Total)

Most Expensive Bookelia Island Listing Fall/Winter 2021 - $1,999,900

Captiva Island

A special place in which you will discover and come to learn that when the sun goes down no one heads home just yet. Secluded location at the end of an already beautiful waterfront island location. Tennis, beaches, shopping, all private.

All Active and Currently Available Captiva Island MLS Listings (14 Properties Total)Currently 

Most Expensive Captiva Island Listing Fall/Winter 2021 - $10,995,000

Hideaway Beach

A private shoreline enchantment with some of the most dazzling waterfront views available in the world. Situated on more than 300 acres including a private owner's beach club. Hideaway Beach is exactly that, a hidden Florida secret.

All Active and Currently Available Hideaway Beach MLS Listings (11 Properties Total)

Most Expensive Hideaway Beach Listing Fall/Winter 2021 - $10,088,000

Isles of Capri

Comprised of a total of 600 acres with four merged mangroves this fantastic opportunity is just 2 miles north of Marco Island's bridge along state road 951. A slower pace of life awaits for visitor's and future homeowner's headed here.

All Active and Currently Available Isles of Capri MLS Listings (13 Properties Total)

Most Expensive Isle of Capri Listing Fall/Winter 2021 - $5,980,000

Keewaydin Island

Consider it paradise and then some. This is a barrier island primarily off the coast of Naples down towards Marco Island. The only way to explore it and reach it is via boat. Boarded by inland waterway to the east and the Gulf of Mexico too.

All Active and Currently Available Keewaydin Island MLS Listings (2 Properties Total)

Most Expensive Keewaydin Island Listing Fall/Winter 2021 - $2,650,000

Key Marco

A most luxurious location off the beaten path. While most residents and visitors coming to the area will stay to the right and head toward Marco Island, for those intrigued with quiet beauty, Key Marco's gated entrance awaits to the left.

All Active and Currently Available Key Marco MLS Listings (14 Properties Total)

Most Expensive Key Marco Listing Fall/Winter 2021 - $3,450,000

Marco Island

By taking a 20 mile drive south of Naples Florida you may come upon something you wish you had discovered a long long time ago - Marco Island. Just 198 nautical miles away from Havana, Cuba, this is southwest Florida at it's best.

All Active and Currently Available Marco Island MLS Listings (235 Properties Total)

Most Expensive Marco Island Listing Fall/Winter 2021 - $18,000,000

North Captiva Island

If there is one paramount way of putting it, then thanks to a hurricane in 1921 this magical true island life would never have been created. Now, only accessible by boat or seaplane, North Captiva is for the serious explorers at heart.

All Active and Currently Available North Captiva Island MLS Listings (23 Properties Total)

Most Expensive North Captiva Island Listing Fall/Winter 2021 - $2,650,000

Sanibel Island

Considered one of the most popular getaway destinations in all of the United States. Sanibel is home to a sea shell collectors most imagined dream come true. White sandy beaches for miles lined with ultra mansions and luxury condos.

All Active and Currently Available Sanibel Island MLS Listings (66 Properties Total)

Most Expensive Sanibel Island Listing Fall/Winter 2021 - $7,995,000

Useppa Island

It is as if we saved the best for last but truly we did not. The content islands profiled in this article are in alphabetical order. However, Useppa Island is one the top rated island luxury destinations in the world. We do not state this lightly.

All Active and Currently Available Useppa Island MLS Listings (12 Properties Total)

Most Expensive Useppa Listing Fall/Winter 2021 - $3,195,000

Contributed by Paul Adams, Realtor - Downing Frye Realty, Inc.