Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. | House in Captiva
5 Bedroom House in Captiva
INTRODUCING ROOSEVELT COTTAGE — A GULF‑TO‑BAY CAPTIVA ESTATE OF PURE ISLAND LUXURY
Tucked along one of Captiva’s most coveted stretches of Gulf‑to‑Bay shoreline, Roosevelt Cottage is a rare island estate offering timeless charm, modern comfort, and an unforgettable resort‑style experience. With nearly 5,000 sq ft of beautifully designed living space across three separate structures, this property is made for extended families, multi‑generational groups, and anyone seeking a private, peaceful slice of Captiva magic.
HOME FEATURES
Elegant, Expansive and Designed for Gathering.
The main home welcomes you with an open, airy floor plan that blends coastal sophistication with relaxed island living. A spacious living area flows seamlessly into the chef’s gourmet kitchen, complete with upscale appliances, a 4‑burner gas range, and a sunny breakfast nook perfect for slow mornings.
PRIMARY KING SUITE RETREAT
The northern wing of the main house features a serene primary king suite with:
• A luxurious ensuite bathroom with claw‑foot soaking tub and walk‑in shower
• A generous walk‑in closet
• A private office/den with TV and half bath — ideal for quiet work or relaxation
UPPER‑LEVEL LOFT + GUEST BEDROOMS
The upper level offers a spacious loft with a queen sleeper sofa and flat‑panel TV — a perfect hangout zone for kids or teens. On each side of the loft, you’ll find beautifully appointed queen guest bedrooms, each with access to a full bathroom featuring a tub/shower combination.
GUEST COTTAGE
Once the original fishing cottage on this tropical estate, this charming standalone retreat includes:
• A cozy living area with TV and WiFi
• A fully equipped kitchen (refrigerator, stove, microwave)
• Dining area
• King bedroom
• Full bathroom
• Private washer/dryer
It’s the perfect hideaway for guests seeking extra privacy and old‑Florida charm.
CARRIAGE HOUSE KING SUITE
Located above the garage, this spacious suite offers:
• A king bed
• Full bathroom
• Comfortable seating area with flat‑screen TV
• Morning kitchen for added convenience
Ideal for couples or guests who enjoy their own quiet corner of the estate.
GULF‑TO‑BAY LIVING AT ITS FINEST
DEDICATED ON‑SITE PROPERTY MANAGER
Enjoy true peace of mind with a professional on‑site property manager available throughout your stay. From coordinating requests to offering local insight and ensuring everything runs seamlessly, guests receive attentive, concierge‑style support from the moment they arrive.
PRIVATE HEATED POOL OASIS
Hidden among lush, mature tropical landscaping, the private heated pool feels like a secluded resort. A cascading waterfall adds to the ambiance, creating a serene retreat for sunbathing, swimming, or unwinding after a day on the water.
PRIVATE DOCK & FISHING PIER ON ROOSEVELT CHANNEL
Step onto your expansive screened lanai and out to your private dock overlooking the tranquil Roosevelt Channel. Perfect for:
• Fishing at sunrise
• Watching dolphins and manatees glide by
• Launching kayaks or paddleboards
• Docking a rental boat for island‑hopping adventures
This is true bayside living — peaceful, scenic, and endlessly relaxing.
EASY GULF ACCESS
With Gulf beaches just moments away, you’ll enjoy the best of both worlds: calm bay waters for wildlife and boating, and soft white sand for swimming, shelling, and sunset strolls.
FULL ACCESS TO 'TWEEN WATERS ISLAND RESORT & MARINA
Located just 0.1 miles from the resort, Roosevelt Cottage guests enjoy access (based on availability) to:
• Two resort pools
• Restaurants & bars and more
THE CAPTIVA EXPERIENCE
Roosevelt Cottage is a true hidden gem — a place where families reconnect, friends unwind, and every day feels like a postcard. From peaceful mornings on the dock to sunset walks on the Gulf, this estate offers a rare combination of luxury, privacy, and authentic island charm.
HAVE QUESTIONS?
Call the Sanibel Captiva Island Vacation Rentals Team for more information, including local vendors for bicycles, baby gear, and more.
Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch is located in Captiva. Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch provides accommodation, featuring Kitchen, Laundry, TV, among other amenities. This House features Kitchen, Laundry, TV, to make your stay a comfortable one.
Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch has 5 Bedrooms , 4 Bathrooms, and max occupancy of 12 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Captiva has interesting places to visit. If you want to learn more about the House in Captiva, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Policies
Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation
Reviews
FAQ's
Is this Captiva house pet-friendly for guests?
Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.
Does the Captiva house have a swimming pool?
Yes, this Captiva house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in Captiva house?
Best-rates for the Captiva house starts from $1,014 per night with includes Entertainment, Private Pool, Bedding/Linens, Fireplace/Heating, Pool, Ocean View, Security/Safety, Air Conditioner, Parking, Pet Friendly, Balcony/Terrace, Wellness Facilities, Barbecue/Outdoor Cooking, Kitchen, Laundry, TV, View, Child Friendly, Internet with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is Captiva house a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the Captiva house wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Captiva house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the Captiva house?
Based on the information reported by the owner or manager, the Captiva house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for Captiva house?
Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
