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

Property number 896348

Platinum Entire home Captiva, FL All Captiva Island & North Captiva rentals
Emerald Kite Rate Advantage

Let us negotiate your rate

Before you book, give us the opportunity to work for you. Our Villa Specialists can contact this home’s management team or owner and try to obtain the best available rate for your dates.

Marni - Emerald Kite destination agent
Marni Captiva Island & North Captiva specialist

Property number 896348

CALL A VILLA SPECIALIST941.900.4552

Live agent direct line. Call for best pricing and ask about daily discounts.

International +1 941.900.4552 7 days a week, 9 a.m. to 10 p.m. EST
Or send your stay details
Starting rate
$1,562 / night
Minimum stay: one week

Rates can change with dates, length of stay, guest count, season, demand, promotions, fees, and management flexibility. A Villa Specialist will confirm the current total and any applicable mandatory fees and taxes.

Request availability & pricing

Gone with the Wind Beach to Bay Estate Main House & Guest CottageCaptiva Island & North Captiva · Property #896348This home is automatically attached to your inquiry.

Would you like a Villa Specialist to call you about this property?

Can’t find exactly what you’re looking for?

Security check loads when you begin your inquiry.

This is a request, not a reservation. A Villa Specialist will reconfirm availability and pricing for your dates and can answer questions about the property, the area, and your stay.

Rates and availability are confirmed for your dates. No particular rate or savings is guaranteed.

Entire home in Captiva Island & North Captiva

Privately owned, professionally managed

5 bedrooms
4 bathrooms
Sleeps 12
1 half bath
Private poolA pool for the use of this property only.
Room for 125 bedrooms, so the whole party stays under one roof.
Platinum rankedEmerald Kite's ranking of the interior furnishings only - not the price, the view or the location.

About this home

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.

What this place offers

24 features listed by the management company.

Inside

Washer / Dryer in Unit
Wireless Internet Access
Ceiling Fans
Air Conditioning
Heated Accommodation
Designed with Indoor/Outdoor Living In Mind
Professionally Designed
Upscale Coastal Decor
Collectable Artwork
Upscale Interior Furnishings
Fully Equipped Kitchen
Breakfast Bar
Top of the Line Appliances
Two Dishwashers
Granite Counters

Outside

Boat Dock
Bay View
Short Walk to Beach
Assigned Parking at Property
Balcony
Deck
Patio
Private Outdoor Pool (Not Caged)

House rules

No Pets

Where you’ll sleep

Bedroom 1King bed
Bedroom 2King bed
Bedroom 3King bed
Bedroom 4Queen bed
Bedroom 5Queen bed
Additional sleepingSleeper sofa · Separate den

Where you’ll be

Captiva, FL. The exact address is confirmed with your agent when you book.

Emerald Kite’s Assessment

Our independent expert assessment of this property, scored out of five.

Not a guest rating or review. Emerald Kite assesses properties independently using our own standards. The Interior score reflects the furnishings and interior quality only—not the price, view, or location.

Location 5/5
Interior decor 5/5
Distance to the beach 4/5
View 4/5
On-call management 5/5

Before you book

What does this property cost?

The owner publishes a starting rate of $1,562 per night, with a minimum stay of one week. Rates move with the season and the length of stay, so call and we will price your exact dates.

Can I book this home online?

No, and that is deliberate. Emerald Kite books by phone so that a specialist who knows Captiva Island & North Captiva can confirm what is genuinely available on your dates and check the home suits your group before anything is committed.

Who looks after the property during our stay?

An established local management company. It is responsible for cleaning, maintenance and guest support while you are there, and your Emerald Kite agent stays reachable for the duration of the stay.

Can we bring a pet?

No - this property is filed as not accepting pets. Use the pet-friendly filter on the Captiva Island & North Captiva page to see homes that do.

When can we check in?

Check-in and checkout times vary by property. Your Villa Specialist will confirm both times, along with the arrival instructions, for this home before your stay.

Booking with Emerald Kite

What you get that a listing site does not

Professionally ManagedPrivately owned and locally managed by a professional cleaning, maintenance, and guest support team during your stay.
A Concierge, at No ChargeOur complimentary VIP concierge service team assists with organizing an array of activities, along with villa pre-stocking and in-property dining and services.
Rate AdvantageOnce your luxury accommodation is selected, a Villa Specialist can contact the home's management team or owner and try to obtain the best available rate for your dates.
Personalized ServiceWhy book online when you can discuss your requirements with your own knowledgeable local accommodation specialist?
Keep exploring

Looking for something different?

Search other Captiva Island & North Captiva vacation rentals. Dates are sent as a request for a Villa Specialist to confirm; they are not a live-availability filter.

Property number 896348

Call a specialist Request pricing

Talk with a Villa Specialist

When should we call you?

Share a few details and an Emerald Kite specialist will call you now or in five minutes.

If you provide a mobile number, you consent to receive messages about your vacation planning. Carrier rates may apply; you can opt out at any time.

Security check loads when this window opens.

Requests after 10 p.m. Eastern Time will be returned the next day.

Having trouble? Use the full Contact page.