5 Br Private Vacation Home Vacation Rental In Captiva, Florida

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.

Located in Captiva, this vacation home is on the waterfront. Sanibel Island Lighthouse is a notable landmark, and the area's natural beauty can be seen at Bowman's Beach and Sanibel Island Southern Beach. Sanibel Captiva Conservation Foundation and Bailey - Matthews Shell Museum are also worth visiting. Take an opportunity to explore the area for outdoor excitement like hiking.