Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch.

Captiva, Florida
$972 avg/night
Bed 5

Bed

Bath 4

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

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, multiR09;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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    2 Total (up To 50 Lbs Per Pet) Pet Friendly Welcoming Dogs Only
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    WiFi Available (fee Applies)
  • OUTDOORS

    Barbecue Grill Dock Fenced Yard Garden Lanai
  • POOL/SPA

    Heated Pool Private Pool
  • BATHROOMS

    4.5 Bathrooms Hair Dryer Shower Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Fishing On Site Hiking Nearby Hiking/biking Trails Nearby
  • ENTERTAINMENT

    DVD Player Flat-screen TV
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair
  • LOCATION HIGHLIGHTS

    On The Lake On The River On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Rates & Availability

Review Review

  • Matt H.

    Submitted Aug 2, 2025

    Stayed Jul 26, 2025

    Great property that is perfect for families. Thank you!

  • Annie G.

    Submitted Jun 8, 2024

    Stayed Jun 1, 2024

    We have stayed at this lovely home before and have loved it though the construction surrounding it. Unfortunately, the neighbors directly to the south of your property are complete jerks. Music blaring until 2 in the am...during the day, the music shook the windows and made it lousy to be in the pool or on the back porch...one of my favorite spots. Due to those ****** we probably will not return.

  • Shelbie W.

    Submitted Apr 30, 2022

    Stayed Apr 23, 2022

    Wonderful property!!! Excellent location!!

  • Terri H.

    Submitted Apr 12, 2022

    Stayed Apr 2, 2022

    The house was just perfect for us. The food prep and eating area were spacious and the pool was steps from the front door. We are thinking about coming back again next year

  • Cheryl Anderson

    Submitted Mar 28, 2022

    Stayed Dec 31, 1969

    Everything we hoped for and more! Delightful and friendly on the phone as well as at check-in. Directions to this particular property should be more specific ( especially the fact that the driveway is the entrance to the home that faces the road).

  • Karen H.

    Submitted Mar 6, 2022

    Stayed Feb 26, 2022

    The house is beautiful and comfortable. It worked perfectly for our family. The main house is spacious with an open feel, yet has many smaller rooms to escape the family noise if needed. The extra living areas on the property worked fantastic for privacy for our children's families. Everything was clean. It was a week of paradise!

  • Michele T.

    Submitted Jan 25, 2022

    Stayed Jan 15, 2022

    The house is beautiful and the location is wonderful. We were very happy with the property manager but there were some problems. There was no wifii and cell service to the cottage and apartment over the garage when we checked in. I assumed this was just what we needed to accept. What this meant was the first night we were in the house and the tornado warnings sounded those of us in these two locations were not aware. Those in the main house were not aware we didn't have the service so they didn't warn us. When we entered the house for breakfast we realized we didn't get these warnings - very scary. On the 5th day of our stay, the service came on in the cottage - which means it should have been on from the beginning. Just think guests should be made aware of this situation. The other issues, no hot water in the cottage for the day and no air conditioning in the upstairs of the main house for a few days was taken care of by the property manager Mark who was very pleasant.

  • austin h.

    Submitted Jan 18, 2022

    Stayed Jan 8, 2022

    The house was perfect for our vacation. Very private setting and relaxing

  • scott w.

    Submitted Jan 8, 2022

    Stayed Jan 1, 2022

    We absolutely loved everything about this home and will be back. The only constructive thing we can add is that beach chairs should always be available to your guests. The ones at the home are all broken.

  • Mike Cardwell

    Submitted Jul 12, 2021

    Stayed Dec 31, 1969

    Like I said, we LOVED the house and property! It was perfect and the dock was well used by our avid anglers! However, we have a few suggestions: 1) Ensure the home is in working order (or inform the renters of any pending issues). 2) Inform the renters of the hose to the left of the garage to rinse your sandy feet, before entering the pool. This was not located until the day before we left. 3) The home really needs extra garbage/recycling bins for a garbage pick-up 1 x week. The garage could easily store them... 4) It would be a WISE INVESTENT to place a 3M FILM to help cut down on the Eastern Sun Rise HEAT that barrels in the main living area/kitchen. I personally did this to my Key's home, and it cut my electric bill down considerably, along with making the home more comfortable, while enjoying the views. https://www.3m.com/3M/en_US/home-window-solutions-us/solutions/uv-protection/ The team members were great, we had no issues. Upon dropping the keys, we expressed our concerns. The team was apologetic, and unaware of the problems we had.

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Total

Includes taxes and fees
$972+
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