**One of the best features of this home is having FULL resort access to 'Tween Waters Island Resort and Spa where you can enjoy two pools, restaurants, live entertainment, additional beach access, and so much more!**

HOME FEATURES
Roosevelt Cottage is located on Captiva Island .1 miles from ‘Tween Waters Island Resort & Spa. This home 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 breakfast area. The northern wing in the main house features a primary king bedroom suite, TV and en-suite bathroom with claw foot tub, shower and walk in closet. This wing also offers a spacious office area with TV and half bath which is convenient to the master suite. 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 with comfortable queen size sleep sofa 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.

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 a 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 a 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. This suite is located above the carriage garage. Roosevelt Cottage has plenty of space with nearly 5,000 sq ft of space combined in three separate structures.

Our favorite feature and center of attention you will find the private heated pool hidden among the lush mature vegetation with a waterfall. Roosevelt Cottage offers a large private boat dock and fishing pier. 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.

Vacation Rental Reviews

• Beautiful Beach Home

  Stayed 7 days ending in May, 2025

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  a guest from Lakeland, Florida recommends this vacation rental

  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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• Spacious with a Great Location

  Stayed 21 days ending in April, 2025

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  Charlie B from Madison, Wisconsin recommends this vacation rental

  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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• A Month by the Sea

  Stayed 28 days ending in February, 2025

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  a guest from Mystic, CT recommends this vacation rental

  We’ve booked Roosevelt cottage for a third year in a row. Its location is perfect. Quiet bay side with private dock and quick walk across Captiva Drive to the Gulf. Begin the day with sunrise from the house and end the day with sunset over the Gulf. The house is cozy in spite of its large size and feels very much like a family home. The house is in a very private and quiet location surrounded by lovely well care for landscaping. Birds are abundant, A family of Osprey nesting on the property were a highlight. Full time caretaker, Mark, was always at the ready to assist with anything we needed. Property rental agents, Michael and Rachel, offer great customer service. Thanks you to the owners for sharing this property with us. Looking forecast to 2026.

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• Amazing and Wonderful Spot in Captiva

  Stayed 7 days ending in January, 2025

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  a guest from Winchester, Massachusetts recommends this vacation rental

  This is a perfect family reunion home. We had 8 adults and 4 young ones. Plenty of privacy and lovely gathering spots in gracious kitchen, screened in porch, out by the pool or at the beach! Property management team helpful and very responsive for any questions. Can’t complain - Enjoy!

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• The perfect place for family time

  Stayed 7 days ending in June, 2024

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  a guest from Water Springs, FL recommends this vacation rental

  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.

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• Excellent place

  Stayed 7 days ending in May, 2024

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  Teresa L from Gainesville, GA recommends this vacation rental

  Rental agency was very responsive and accommodating. House was beautiful and well stocked. Very roomy. Ice machine awesome. Pool was great. We had party of 8. Couldn't have been better! Mark the property manager was a hoot!

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• Lovely Home with Terrific Location

  Stayed 14 days ending in April, 2024

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  Charlie B from Madison, Wisconsin recommends this vacation rental

  What an exceptional home! Perfectly situated between the channel and beach, the home offered easy access to both. We docked a boat at the house during our stay, and spent some days in Pine Island Sound, others on the gulf beach, and yet others at the lovely pool. Home is spacious with an expansive and well appointed kitchen. Mark the property manager lives next door and quickly and courteously attended to any minor issues. Access to the gym and restaurants at Tween Waters was fun and convenient, and we greatly enjoyed other Captiva restaurants which are bouncing back strongly from the hurricane. We will likely stay at this home again in the future!

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• A Captiva Month By the Sea

  Stayed 28 days ending in February, 2024

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  a guest from Mystic, CT recommends this vacation rental

  We’ve spent January in Captiva for 20 years. It was wonderful to be back having to skip 2023 due to Hurricane Ian. Our usual accommodation for 20 years was not yet repaired.
  
  Rachel and Michael from Sanibel Captiva Island Vacations went out of their way to secure a place for us to stay this year. Roosevelt Cottage was perfect. A dock on the bay and an easy quick walk to the beach along a private access point. Mark the caretaker of the property was always available to help with anything we needed.
  
  Rachel and Michael have secured us a place for January 2025, another one of their properties, that is more suited size wise for two of us. We are very grateful.
  
  Roosevelt Cottage is perfect for an extended family gathering or group of friends. We highly recommend it.

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• Captiva House

  Stayed 7 days ending in July, 2022

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  a guest from Lakeland, FL recommends this vacation rental

  This house holds the breathe and beauty of Florida! The expansive sleeping and lining areas are a perfect match for a family reunion !

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• A Tropical Paradise

  Stayed 14 days ending in July, 2022

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  Rosemary C from Royal Palm Beach FL, Florida recommends this vacation rental

  An ideal house for our multi-generational family vacation, plenty of space to be together or off on your own. We enjoyed the beautiful views of the channel and the sunrise from the much used screened patio. While we did not fish off the dock we did use tie up the boat we had for part of the time, highly recommend doing this, you see so much more out on the water! We had a couple of maintenance issues that were handled quickly by the on-site caretaker.

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• Paradise

  Stayed 7 days ending in May, 2022

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  Carrie B from Orting, WA recommends this vacation rental

  Loved every minute

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• Spring Break #5 at Roosevelt Cottage

  Stayed 7 days ending in April, 2022

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  Molly W from Arlington, VA recommends this vacation rental

  Absolute perfection, as always! Roosevelt Cottage was exactly what we needed as we relaxed in Captiva for our 5th straight Spring Break. Comfortable, clean, best pool for playing, relaxing and happy hour. Lots of snook action off the dock each night. Sanibel Captiva Island Vacation Rentals made it all easy and convenient.

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• Family Spring Break Vacation

  Stayed 7 days ending in March, 2022

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  Vicki U from Garden City, KS recommends this vacation rental

  Our whole family had a wonderful vacation at this wonderful vacation home. There were eleven of us, five of those grandchildren from 8 to 15 and they all relaxed with fishing, game playing and swimming. The living area was comfortable for our whole group. We were able to also have our separate spaces for relaxing and sleeping. We rented a boat and enjoyed catching fish and viewing dolphins and manatees. It really met our expectations of an island getaway! This is a beautiful property.

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