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ROOSEVELT COTTAGE

House in Captiva, FL

12 guests·5 bedrooms·4.5 bathrooms
4.8 · 25 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Private heated pool framed by lush landscaping offers serene island luxury.

Entertainment & Amenities

Entertainment & Amenities

Resort-pass access to Tween Waters adds pools, dining, and live entertainment.

Location & Accessibility

Location & Accessibility

Short walk to Gulf beaches and Captiva shops enhances convenience.

What guests are saying

Summarized with AI
Star icon

4.8

Rated 4.8 out of 5 from 25 reviews

Guests consistently highlight the spaciousness and beauty of the property, with many praising the well-appointed kitchen and comfortable gathering areas. The private pool and access to nearby amenities enhance the overall experience. Reviewers appreciate the attentive property management and the serene, well-maintained surroundings. Families find it an ideal setting for reunions, with ample room for relaxation and fun. Overall, guests express high satisfaction and recommend this property for future stays.

See all 25 reviews.

Property details

Stunning Gulf to Bay Private Captiva Island Getaway. 7-night minimum stay 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.

Sleeping arrangements

Bedroom 1

3 King Beds

Bedroom 2

2 Queen Beds

Bedroom 3

1 Sofa Bed

What’s included

  • Self check-in

    Self check-in

  • Parking

    Parking

  • Pool

    Pool

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Pets allowed

    Pets allowed

Guest reviews

Star icon 4.8 | 25 reviews
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Ed M.

Beautiful Beach Home

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May 2025

We had an amazing stay at this beautiful Captiva home. We had plenty of space for 7 adults and 2 children . Large, well appointed kitchen and living area. We enjoyed beach access, private pool as well as passes to Tween Waters Resort. Would highly recommend this property!

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Charlie B.

Spacious with a Great Location

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April 2025

This was our second year staying at Roosevelt Cottage — 2 weeks in 2024 and 3 weeks in 2025. The rental is unique in checking some really key boxes for us: dockage on Roosevelt Channel (we rent a boat during our stay), a nice pool area, and a short walk to the beach. The house is spacious and very comfortable and generally in good condition, especially in wake of hurricanes that have hit Captiva in recent years. Walking proximity to Tween Waters and short drives to other Captiva restaurants are a plus. A friendly, responsive and very capable property manager/handyman is also nearby. With five bedrooms the property could accommodate a pretty large group.

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Adina

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December 2024

Lovely house for a comfortable family vacation with three generations incl young kids. Lots of room to spread out, swim, loved pool and pickleball at Tween Waters resort. Great beach access!

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Nancy S.

The perfect place for family time

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June 2024

Roosevelt cottage was perfect for our family. This is the second year we've stayed there and everything was close to perfect. My whole family loved being there and wish we could have even more time.
Michael and his staff could not have been more accommodating. It was a great experience.

Know before you go

Self check-in

House rules

Check-in: 4:00pm

Checkout: 10:00am

Pets allowed

No smoking

No parties

Have a question about this property?

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