Onsite parking is available at the property.

Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. Reviews, Deals & Photos 2026

Q: Does Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. have a pool?

Yes, this property has a pool. Pool types include heated pools.

Q: Is Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

Q: Where is Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. located?

Situated in Captiva, this vacation home is within a 10-minute walk of Captiva Beach and J. N. Ding Darling National Wildlife Refuge. Captiva Chapel By the Sea and Jensen’s Marina are also within 2 mi (3 km).

10/10 Excellent

Matt H.

Aug 2, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property that is perfect for families. Thank you!

Stayed 7 nights in Jul 2025

10/10 Excellent

Charles Y.

Sep 9, 2019

Liked: Cleanliness, check-in, communication, location, listing accuracy

Roosevelt Cottage

Our Family had a great time !

8/10 Good

Annie G.

Jun 8, 2024

Liked: Cleanliness, check-in, communication, listing accuracy

Lousy neighbors

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.

Stayed 7 nights in Jun 2024

10/10 Excellent

sarah d.

Feb 26, 2019

Fantastic Stay!

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. A couple CONS: the mattress in the cabin is pretty hard and uncomfortable, and the pillows throughout need to be replaced. There were fire ants near the pool, but the ant spray we found in the house took care of them. We are already planning on coming back next year. What a fantastic stay we had! Thank you!!

Stayed 7 nights in Feb 2019

10/10 Excellent

Shelbie W., Leesburg, FL

Apr 30, 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Booked Again!

Wonderful property!!! Excellent location!!

Stayed 7 nights in Apr 2022

10/10 Excellent

Terri H.

Apr 12, 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spring Break with family

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

Stayed 7 nights in Apr 2022

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10/10 Excellent

Cheryl Anderson

Mar 28, 2022

Everything we hoped for and more! Delightful and friendly on the phone as well as at check-in.

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).

10/10 Excellent

Karen H.

Mar 6, 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Week!

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!

Stayed 7 nights in Feb 2022

8/10 Good

Michele T., Wayland, MA USA

Jan 25, 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property, great location but...

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.

Stayed 7 nights in Jan 2022

10/10 Excellent

austin h., Bloomfield

Jan 18, 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property

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

Stayed 7 nights in Jan 2022

10/10 Excellent

scott w.

Jan 8, 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Christmas Vacay

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.

Stayed 7 nights in Jan 2022

This review comes from a trusted partner site and has not been verified.

8/10 Good

Mike Cardwell

Jul 12, 2021

Like I said, we LOVED the house and property! It was perfect and the dock was well used by our avid

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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10/10 Excellent

Rich Gookin

Jun 28, 2021

A clear/net covering on the pool would negate the mosquitos and enable visitors to enjoy the pool.

10/10 Excellent

Megan S.

Jun 12, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for extended family stay

Absolutely gorgeous property. Loved sitting on the screened-in porch and watching the boaters go by. The kitchen/family room were our hub... plenty of room for everyone. Master bedroom and bathroom were incredible. Two queen bedrooms upstairs had some temperature issues (too cold and then too warm), but not bad enough to call the property manager. Kids loved spending time in the upstairs loft area. Both outbuildings were well-appointed. Fisherman's cottage had some ants/spiders/roaches, and the property manager came out right away to spray. Appreciated being able to use the garage to store our rental bikes and beach equipment. We did not end up using any of the property's equipment except for the wagon, which worked great for hauling chairs/umbrellas/coolers/toys down the long driveway to the beach. Could not ask for a better beach location! Almost no neighbors, and TONS of great shells (especially at low tide). Biggest drawback on the entire property is the smell in the pool area. We thought it was the neighbor's construction's porta-potty (which is right next to the pool)... but the property manager told us that the house's septic system is right by the pool. So, every time we went to the pool, we always smelled septic/sulfur/stink. The property manager said it would just be when the wind was blowing a certain direction... but we noticed it all the time. We still used the pool frequently, but would have been able to enjoy it more without the smell. Also, it's Florida in summer, so make sure to bring bug spray and sunscreen if you plan to stay outdoors for any length of time.

Stayed 7 nights in Jun 2021

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

charles canter

May 31, 2021

All of our family (9+5 kids) loved property.

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. courteous, informative, quick to respond to issues

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Timothy Donnelly

Apr 26, 2021

The only thing I would recommend is leaving a little larger supply of starter items: soap, toilet pa

The only thing I would recommend is leaving a little larger supply of starter items: soap, toilet paper, paper towels, etc...

10/10 Excellent

Annie G.

Apr 20, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Escape

Loved the property. Construction on either side was a bit frustrating but not totally distracting. Only issue was possible disruption of septic field/tank by next door construction crew.

Stayed 7 nights in Apr 2021

10/10 Excellent

danica j.

Mar 23, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Captiva Spot

Our stay at Roosevelt included 4 BFF senior girls and 2 sets of parents (our COVID pod). One set of parents stayed in the main house master with the 4 girls and the other parents in the cottage. We walked across the street to the beach every day, used the pool every day, and cooked meals in the kitchen every day. The private beach access leads to a VERY quiet section of Captiva. We rented a boat and tied it up at the dock. The house is lovely and convenient. 100% would book this property again.

Stayed 7 nights in Mar 2021

10/10 Excellent

keith a.

Mar 16, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family reunion for March birthdays

We found the property to fit our needs of 8 adults and 1 child under 2 just fine - 4 separate families, so the many different sleeping arrangements fit just great. We loved the big screened porch facing the Roosevelt Channel, the wonderful big kitchen table that fit us all for meals and evening games; the close proximity to the beach by beach wagon filled with beach chairs and kid toys. The living room was good for evenings of chatting; we didn't turn on one tv the entire 2 weeks. Grocery convenience store was right down the road for quick last-minute pick ups- otherwise, the bigger grocery stores on Sanibel weren't too far away. There are several restaurants close by the property, but we opted for lunches out and cooking dinners in, so don't have alot of food reviews to offer. We did like Doc Ford's , key lime pie at Keylime Bistro, cakes from the Bubble Room. My only complaints would be the property advertised bikes to use, but both bikes were inoperable (flat tires, no seats); and we stayed for two weeks but the complimentary welcome kits only gave us 2 packets of dishwasher soap, 3 garbage bags,, 1 packet of laundry soap ( we brought laundry soap, knowing we had a toddler). I would suggest perhaps more supplies for those staying for more than one week, considering the price of the property. We loved our stay here on Captiva Island - a great family time!

Stayed 14 nights in Feb 2021

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Lisa Leach

Dec 21, 2020

We plan to rent this property again.

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 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.

This review comes from a trusted partner site and has not been verified.

8/10 Good

Ted Oberg

Jun 29, 2020

We loved it.

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.

This review comes from a trusted partner site and has not been verified.

8/10 Good

Karen Bloom

Jan 1, 2020

The TV's in the Carriage House and Guest Cottage are 10-15 years old.

The TV's in the Carriage House and Guest Cottage are 10-15 years old. The TV in the Guest Cottage was very pixelated. One of the TV's in the big house has a yellow cast to it. The large TV in the big house was great. My children were supposed to stay in the Carriage House but there was a fragrance there that gave my daughter a headache so we had to switch. We paid to have the house cleaned but nobody asked us when we wanted it cleaned. Since Christmas was on Wednesday, we assumed it would be cleaned on Tuesday. We did cancel the cleaning on Thursday as we were leaving Saturday. I did call your office to complain about the lack of wifi in the two buildings. A man came over to verify that there was no wifi. He told me to tell the owner to put in routers. I thought that was strange as he was from your office and the office, not I communicates with the owner.

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Charles Yanes

Aug 19, 2019

Excellent property, very spacious, clean and homey.

Excellent property, very spacious, clean and homey. We had an amazing time with our 4 boys. Sue and the staff were attentive, professional and very courteous. They responded quickly to any inquiry.

10/10 Excellent

Kim B.

Apr 20, 2019

Excellent

It was a wonderful vacation & the property was beautiful

Stayed 8 nights in Mar 2019

10/10 Excellent

Jenny B., Knoxville, TN

Dec 10, 2018

Roosevelt Cottage

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. We’ll be back!

Stayed 7 nights in Nov 2018

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

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