Calico Jack's Lookout

Top Reasons to Book Calico Jacks Lookout:

* Roof Top Deck with Separate Sleeping Quarters and Ensuite Bathroom and Hot Tub

* The Beach is Right Across the Street at Island Tower's Resort

* Beach Views from the Front Porch and Top Floor Deck

* Plenty of Parking, 3 Parking Spaces

* 180 Feet to Beach Access #17

* 2.3 Miles to Times Square

* Professionally Managed; 24/7 Service

*This property does not allow parties of adults under the age of 25. *

Welcome to Calico Jack’s Lookout, a stunning coastal retreat where breathtaking Gulf views, a private heated pool, modern beachside luxury, and the spirit of island adventure come together on beautiful Fort Myers Beach.

Perfectly situated directly across from the beautiful sands and turquoise waters of the Gulf, this beautifully appointed home offers an exceptional location on Estero Boulevard with easy beach access just steps away. After a day at the beach, come home and unwind in your private heated pool, surrounded by comfortable pool loungers that create the perfect setting for soaking up the Florida sunshine, enjoying a refreshing swim, or simply relaxing with a good book. Publix and a few local restaurants are also a short walk from the home. Inspired by the lookout points sailors once used to scan the horizon, Calico Jack’s Lookout invites guests to experience Fort Myers Beach from a truly elevated perspective.

Inside, you’ll find bright, coastal-modern interiors adorned with thoughtfully curated artwork, comfortable furnishings, and an open, welcoming atmosphere designed for relaxation. Expansive windows and outdoor living spaces showcase spectacular Gulf views, allowing the beauty of Fort Myers Beach to become part of every moment of your stay.

The crown jewel of the home is the private rooftop retreat. Ascend to the top-floor lookout suite, where a cozy full sleeper sofa creates the perfect spot to unwind while taking in panoramic views of the Gulf, stunning sunsets, and the island skyline. Step outside onto the rooftop deck and soak in the hot tub as gentle sea breezes drift by and the sun melts into the horizon.

Whether you’re enjoying morning coffee while watching beachgoers stroll the shoreline, lounging beside your private heated pool, spending the day shelling and swimming, or gathering under the stars after sunset, every experience at Calico Jack’s Lookout is designed to help you embrace the laid-back luxury of island life.

Located on the desirable mid-island section of Fort Myers Beach, you’ll be close to local restaurants, shopping, marinas, and all the activities that make this island paradise a favorite destination year-round.

Drop anchor, settle in, and discover why Calico Jack’s Lookout offers one of the most unforgettable vantage points on Fort Myers Beach.

The Bed Set-up

Primary Bedroom: King Bed

Guest Bedroom 1: King Bed

Guest Bedroom 2: Twin over Full Bunk

Living Room: Sofa Sleeper - Queen

Bonus: Also includes Lookout Sleeping Space-Sofa Sleeper

Area Activities:

Welcome to Fort Myers Beach! There are multiple state parks nearby that are waiting for your adventures. Jump on the trolley to take you south to the secluded Lover's Key State Park or go north to Bowditch Point Park. The Fish Tale Marina offers boat rentals and dockage for those wanting to get out on the water. Travel around the island in style in a rented Moke or golf cart. Trolley service is also available from Estero Boulevard to the Times Square area, the central hub of Fort Myers Beach. If a day trip is what you are looking for check out the Key West Express for an unforgettable trip to Key West. Don’t forget to see Sanibel Lighthouse, which is less than 15 miles away!

4841 Estero Blvd
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