Lush, Private Captiva Island Getaway Gulf to Bay Along 'Tween Waters Stretch

Easy Beach Access from Main Home, Guest Cottage and Carriage Guest Suite

  12 guests
  5 bedrooms
  4 full / 1 half bathrooms
  Has Pool
  Allows Pets
  5716 sq. ft.

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Sleeping Arrangement

Bedroom 1
1 King
Bedroom 2
1 King
Bedroom 3
1 King
Bedroom 4
1 Queen
Bedroom 5
1 Queen
Common Space
1 Sofa Bed



This charming bayfront home on Captiva Island is a gulf to bay estate, has private beach access and is on the Tween Waters stretch. The property has a guest dock and private heated pool surrounded by lush tropical landscaping. This tropical estate home offers the main home, guest cottage and carriage guest suite accommodating up to 12 guests. Located on the Tween Waters stretch, Roosevelt Cottage offers a convenient waterfront location with easy beach access. This island treasure continues to be one of the island's favorite vacation rentals on Captiva. This is a Charmer! Offers seclusion, views, beach access with numerous amenities. This home will welcome your family dog with approval. 


Roosevelt Cottage features an open floor plan for extended family and friends with a spacious living area opening into the chef's gourmet kitchen with 4 burner gas range, upscale appliances and casual breakfast area.

The northern wing on the main living level features a master bedroom suite with a king bed, TV and en-suite bathroom with claw foot tub, shower and walk in closet. This wing also offers a spacious den office area with TV and half bath which is convenient to the master suite as well as the main living area. The main level also features a formal dining room an additional den with TV off of the kitchen area plus a large laundry room providing two sets of stack washer/dryers for your convenience.

The property features an expansive screened lanai overlooking the dock and Roosevelt Channel. The upper level of the main home offers a spacious loft area with comfortable queen size sleep sofa, wet bar and a flat panel TV. There is a guest bedroom on each side of the loft both with queen sized beds and a full bathroom with a tub/shower combination. The floor plan is expansive and offers privacy and comfort.

Just outside the main home is the charming guest cottage which was the original fishing cottage on this tropical oasis. The guest cottage offers a quaint living area with TV and WIFI and a handy kitchen with an under-counter refrigerator, stove and microwave plus a dining area. The guest cottage also has a comfortable sleeping area with a king-size bed, full bathroom and utility room with a washer and dryer.  

For additional family and friends, there is an additional carriage house guest suite which sleeps 2 with a king size bed, full bathroom and spacious seating area equipped with flat screen TV.  A morning kitchen in this suite is convenient for guests without going into the main home for early morning coffee or late night snack. This suite is located above the carriage garage and is just steps from the main home. Roosevelt Cottage has plenty of space with nearly 5,000 sq ft of space combined in three separate structures. The carriage suite also provides a queen blow up bed for additional sleeping or can be moved to the main home into the private den or sunroom off of the kitchen. 

Our favorite feature and center of attention you will find the private heated pool hidden among the lush mature vegetation with a soothing waterfall feature. Roosevelt Cottage offers a large private boat dock and fishing pier.  Private charters are available for fishing, shelling, eco-tours and sunsets. This estate home is a hidden gem you and your family will treasure while enjoying the perfect vacation destination. Roosevelt Cottage estate offers extended family and friends many options for sleeping and providing a relaxing atmosphere and privacy.

This private guest dock will accommodate your boat or a boat rental up to 30 feet. When you walk down the driveway to go to the private beach, enjoy the convenience of a beach wagon, beach chairs, beach towels and umbrella for your island escape! Pac N Play, booster chair and high chair also available.


Captiva is known for its array of waterfront activities including, boating, fishing, shelling and a laid back relaxing atmosphere. Captiva offers 6 miles of award winning beaches with fantastic shelling. Sanibel and Captiva Island has consistently been named a top island vacation destination for couples and families — regionally, nationally and internationally. Sanibel and Captiva Island offers miles of pristine beaches (America’s best shelling beaches), as numerous award winning beach designations, 25 miles of bike paths, 250 kinds of shells and 0 stop lights. Top Sanibel Island attractions include: J.N. "Ding" Darling National Wildlife RefugeCROW-Clinic For the Rehabilitation Of Wildlife, the Bailey-Matthews National Shell Museum and Sanibel Lighthouse & Fishing Pier.


Enjoy our exclusive Renter's Rewards with free access to some of the finest resorts on Captiva and Sanibel — complete with free or discounted values of more than $250 on local dining, beverages, shopping, spa services, family photography, boating, kayaking, fishing, paddleboarding, golfing and more.

Have questions? Call the Sanibel Captiva Island Vacation Rentals Team for more information, including a list of local vendors that rent items such as bicycles, kayaks, and baby equipment.


  • Private Beach Access
  • Private Guest Dock (boat length up to 30 feet) /Fishing Pier
  • Heated Pool
  • Fishing Pier
  • Gas Grill (Direct Gas Line)
  • Washer/Dryer In Main Home
  • Washer/Dryer In Cottage
  • Washer/Dryer in Garage
  • Keurig
  • Nespresso
  • Waterview
  • Garage Access
  • Landline For Local Calls
  • 3 King
  • 2 Queen
  • Queen Sleep Sofa
  • Pac N Play
  • High Chair
  • Booster Seat
  • Water Sports Discounts
  • Boat Rental Discounts
  • Paddleboards And Kayaks Can Be Launched From Property
  • Pets Welcome With Approval
  • Boat Trailer Storage Available During Your Stay



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Write a Review
Orlando, US
Reviewed: Jun 14, 2021
Property Manager
affton, US
Reviewed: Jun 1, 2021
Property Manager
courteous, informative, quick to respond to issues
All of our family (9+5 kids) loved property. We produced a lot of trash and recycling. As trash comes middle of the week bigger and more trash receptilces (including recycling) would be ideal.
Leawood, US
Reviewed: Apr 27, 2021
Property Manager
Dublin, US
Reviewed: Mar 1, 2021
Property Manager
coral gables, US
Reviewed: Jan 15, 2021
Property Manager
Pinson, US
Reviewed: Dec 22, 2020
Property Manager
The team I spoke with while awaiting the time for our trip were helpful in dealing with the covid anxiety regarding our stay and travel. The rental office had a variety of well documented properties for choosing the perfect place.
We plan to rent this property again. It was a perfect fit for our family of parents and grown children to relax away for the holiday. This property was everything we wanted for our stay. We enjoyed a family Christmas celebration here. It is the most wonderfully peaceful and secluded place and yet convenient to anything we wished to venture out and do. We hope to continue to stay here for a family Christmas tradition. It was perfect!
The Woodlands, US
Reviewed: Jun 29, 2020
Property Manager
We loved it. It is a beautiful home with an incredible location - on the bay, close to the beach. The beach was wonderfully secluded with no parking nearby, we felt like it was all ours. The cottage and garage apartment are so fantastic. It really was a perfect spot for our family get away.
Reviewed: Sep 28, 2019
Very nice place to stay.
Reviewed: Aug 20, 2019
Property Manager
Sue and the staff were attentive, professional and very courteous. They responded quickly to any inquiry.
Excellent property, very spacious, clean and homey. We had an amazing time with our 4 boys.
Northville, US
Reviewed: Apr 8, 2019
Property Manager
Reviewed: Feb 9, 2019
We just got back from a wonderful week in this house (mansion!). We usually stay in a condo in Sanibel, but we had both grandparents with us, so we opted for a house instead. We were so happy to change it up, and it was neat to try Captiva for the first time. There is more than enough room for everyone - master bedroom downstairs, downstairs den that we put the pack-and-play in for the baby, two bedrooms upstairs, a cabin with a small kitchen for my parents, and a room on top of the garage that actually went unused! The biggest perk of this place is the awesome heated pool. The kids loved it, and we swam our hearts out! Other perks of this place are the large main kitchen, view of the intercostal waterway, short walk down the driveway to the beach (sunsets every night were awesome), lush landscaping, and how QUIET and serene it is in and around the house. We also loved that they provided a pack-and-play (however we brought our own - didn't know they had one on sight), and there is an umbrella stroller & beach gear in the garage.
Reviewed: Nov 17, 2018
Fabulous, beautiful place for families or couples. Three large bedrooms in the main house, cozy guest house with little kitchen and sitting area and a bedroom and bath over detached garage. The farmhouse kitchen has a big harvest table that easily seated 12 for Thanksgiving. Beautiful bay view (with private dock) and just a short walk to the very quiet beach. Well be back!
Reviewed: Jul 3, 2018
Amazing rental... layout and style of decor was really great! Perfect setup for two families and two grandparents although wish the upstairs bedrooms had twins versus double beds.
Reviewed: Apr 25, 2018
Wonderful Captiva experience, complete with seeing the green flash twice!
Reviewed: Apr 2, 2018
We had the perfect vacation at Roosevelt Cottage! Captiva is amazing, of course, but Roosevelt Cottage was as much a part of our vacation as the island. The home is beautiful, spacious and comfortable. The pool was perfect for playing and relaxing. ReMax was attentive and helpful with all of our questions. We loved every second and we look forward to a return trip next year!
Reviewed: Mar 26, 2018
Great experience on Captiva. Central location, about 1mi south of the mini-village with restaurants on Captiva. Guest dock on back-side for our Boston Whaler. Generous common areas in a nicely designed and tastefully appointed house. Felt roomy for our group of 10. Master down for our 80+ YO uncle. Two beds up and two separate sleeping areas in out buildings. Nicely private. Sunny weather, too!
Reviewed: Mar 19, 2018
We loved the place, it was comfortably elegant. No complaints but a few

Comfortabley elegant no complaints. Just a few suggestions maybe have twin beds in one of upstairs bedrooms to accommodate younger children and or pull out sofa in loft area. In kitchen area A four slice toaster, martini shaker and a booster seat for smaller children. Another lounge chair or two in pool area and
a wagon for beach stuff. Just suggestions we will definitely rebook.