Gone with the Wind Beach to Bay Estate Main House & Guest Cottage

Bedrooms: 5    Bathrooms: 4    Sleeps: 12    Save to Favorites

  • Property 896348
  • Platinum (5 Star)
  • Captiva Island & North Captiva
  • Privately Owned Professionally Managed®
  • Minimum Stay: One Week
  • Average Rate: $1,562/Night
  • Low Season Rate: $1,401/Night
  • Peak Season Rate: $3,032/Night
  • Rates do not reflect taxes and fees and are subject to change without notice.
  • Location: 5 Stars
  • Interior Decor: 5 Stars
  • Distance to Beach: 4 Stars
  • View: 4 Stars
  • On-Call Management: 5 Stars

Why Book with Emerald Kite?

Your vacation deserves more than a gamble! When renting with private owner listing platforms it's easy to miss critical details about a property. You may end up in a home that doesn't suit your needs.

Emerald Kite provides detailed, one-on-one consultations BEFORE booking to discuss the property, proximity to attractions, and special requirements.

Why settle for less?

Call Our Local Agent

USA: 941.900.4552

Intl: +1 941.900.4552

7 Days a Week 9am - 10pm EST



Captiva Island is a hidden treasure, boasting a prime location just 1 mile from the renowned ‘Tween Waters Island Resort & Spa. This exceptional property combines comfort and elegance, making it an ideal choice for families and friends seeking a memorable getaway. With its open floor plan, the home invites you to experience a seamless flow between the spacious living area and a chef's gourmet kitchen, equipped with a four-burner gas range and upscale appliances. The design encourages gatherings, whether for a casual breakfast or a sumptuous dinner. The primary suite, located in the northern wing of the main house, features a luxurious king bed, an en-suite bathroom complete with a clawfoot tub, and a walk-in closet that ensures you have everything you need at your fingertips. The property’s layout is thoughtfully designed for both relaxation and entertainment. The formal dining room sets the stage for elegant meals, while an additional den off the kitchen provides a cozy retreat for movie nights. The convenience of a large laundry room with two sets of stackable washer/dryers adds to the ease of your stay, allowing you to focus on enjoying your vacation rather than chores. The expansive screened lanai offers breathtaking views of the dock and Roosevelt Channel, making it a perfect spot for morning coffee or evening cocktails as you soak in the tranquil surroundings. As you ascend to the upper level, a spacious loft awaits, featuring a comfortable queen-size sleep sofa and a flat-panel TV for your entertainment needs. This area is flanked by two guest bedrooms, each furnished with queen-sized beds, ensuring ample sleeping space for family and friends. A full bathroom with a tub/shower combination serves this level, providing convenience and privacy for all guests. Just steps away from the main house, the charming guest cottage adds to the allure of this property. Originally a fishing cottage, it now serves as a cozy retreat equipped with a living area, TV, and Wi-Fi. The kitchenette, complete with a refrigerator, stove, and microwave, allows guests to prepare meals with ease. The inviting sleeping area features a king-size bed, a full bathroom, and a utility room with a washer and dryer, making it a self-sufficient haven for visitors. For those requiring even more space, the carriage house guest suite is a delightful addition. This suite comfortably accommodates two guests with a king-size bed and a full bathroom, along with a spacious seating area equipped with a flat-screen TV. A morning kitchen adds convenience, allowing guests to enjoy breakfast in the comfort of their private space. Nestled above the carriage garage, this suite offers an extra layer of privacy while still being part of the larger estate. One of the standout features of this property is the private heated pool, surrounded by lush, mature vegetation that creates a serene oasis. The tranquil sound of a waterfall adds to the ambiance, making it an ideal spot for relaxation after a day of exploring the island. The large private boat dock and fishing pier provide direct access to the water, perfect for those looking to indulge in boating or fishing adventures during their stay. Roosevelt Cottage is not just a vacation rental; it’s a place where extended family and friends can come together, creating lasting memories in a beautiful setting. The thoughtful design and ample accommodations ensure that everyone has their own space while still being able to enjoy shared moments. The property’s charm and amenities make it a hidden gem on Captiva Island, offering a unique blend of luxury and comfort. Emerald Kite has been welcoming visitors to the area for over 20 years. We provide one-on-one assistance on our phone line where you can discuss this property or alternate options that may be available in the Captiva Island area for your chosen dates. All guests are treated as VIPs and will receive complimentary concierge services prior to and during their stay, ensuring a personalized experience that caters to their every need.

Available! Call Local Agent - 941.900.4552

Note: Rentals are a minimum of 7 nights, from Saturday to Saturday.

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Photo Disclaimer: Images represent the overall interior and furnishings of a property at the time photographs are taken. Owners do and will continue to decorate and change furnishings, beds, etc. at their discretion and these updates/changes may not be reflected. Views of the property's closest beach, mountain or ski areas may also be represented, however, these images may not reflect the view from the actual accommodation. Views from the property may be limited by natural tree growth outside of our control.