




Discover the ultimate island escape at Roosevelt Cottage, a stunning Gulf-to-Bay estate offering pure island luxury in Captiva, Florida. Tucked along one of the most coveted stretches of shoreline, this rare property blends timeless charm with modern comfort across nearly 5,000 square feet of beautifully designed living space. Whether you are traveling with an extended family or a multi-generational group, this estate provides a private, peaceful slice of Captiva magic.
The property is thoughtfully arranged across three separate structures to maximize privacy and relaxation. The main home features 5 bedrooms and 4 bathrooms, accommodating up to 12 guests. The layout includes a serene primary king suite with a luxurious ensuite bathroom featuring a claw-foot soaking tub, walk-in shower, a generous walk-in closet, and a private office/den with its own half bath. The upper level boasts a spacious loft with a queen sleeper sofa and flat-panel TV, flanked by beautifully appointed queen guest bedrooms with access to full bathrooms.
For those seeking additional seclusion, the estate includes a charming standalone Guest Cottage—the original fishing cottage of the property—featuring a king bedroom, full bathroom, fully equipped kitchen, and private washer/dryer. Additionally, the Carriage House King Suite located above the garage offers a king bed, full bathroom, seating area, and a convenient morning kitchen.
Experience the best of bayside living with an expansive screened lanai leading to a private dock and fishing pier on the Roosevelt Channel. Here, you can fish at sunrise, launch kayaks, or watch dolphins and manatees glide by. The grounds also feature a private heated pool oasis hidden among lush tropical landscaping with a cascading waterfall.
Located just 0.1 miles from the Tween Waters Island Resort & Marina, guests enjoy the luxury of full resort access (based on availability), including two resort pools, restaurants, and bars. With the soft white sands of the Gulf beaches just moments away, you have the perfect balance of calm bay waters and iconic sunset strolls.
Practical Information:
From the attentive support of a dedicated on-site property manager to the authentic island charm of the cottages, Roosevelt Cottage is a hidden gem where every day feels like a postcard.
This description is for informational purposes. Please verify all details, including amenities, policies, fees, and availability, on the booking platform before booking.
You’ll be staying in someone’s home, so please treat it with care and respect.

