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

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exterior
exterior
exterior
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Reviews

9.8 out of 10
Exceptional
5 bedrooms4+ bathroomsSleeps 12

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Outdoor space

Rooms & beds

5 bedrooms (sleeps 12)

BEDROOM

1 King Bed

BEDROOM

1 Queen Bed

BEDROOM

1 Queen Bed

BEDROOM

1 King Bed

BEDROOM

1 King Bed

4 bathrooms, 1 half bathroom

Bathroom

Bathtub · Shower only

Bathroom

Bathroom

Bathtub · Shower only

Bathroom

Shower only

Bathroom

Shower only

Spaces

Kitchen
Garden

About this property

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

**ONE OF THE BEST FEATURES OF THIS HOME IS HAVING FULL RESORT ACCESS TO 'TWEEN WATERS INN AND MARINA WHERE YOU CAN ENJOY TWO POOLS, RESTAURANTS, LIVE ENTERTAINMENT, ADDITIONAL BEACH ACCESS, AND SO MUCH MORE! **

** Based on availability.



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.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load the dishwasher
Strip any used beds and gather used towels
Remove personal items and take out the rubbish
Turn off the lights
Failure to complete these may result in a negative review from the host.
100% refund if reservation is cancelled at least 60 days before the arrival date

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Captiva

Captiva is home to this holiday home. Captiva Chapel By the Sea and Sanibel Historical Village and Museum are local landmarks, and some of the area's activities can be experienced at Jensen’s Marina and McCarthy's Marina. Sanibel Captiva Conservation Foundation and Bailey - Matthews Shell Museum are also worth visiting. Take the opportunity to explore the area for outdoor excitement like hiking/biking trails.
View more Holiday homes in CaptivaOpens in a new window
Map
Captiva, FL

What's nearby

  • Captiva Beach - 1 min walk - 0.2 km
  • J. N. Ding Darling National Wildlife Refuge - 1 min drive - 0.2 km
  • Captiva Chapel By the Sea - 3 min drive - 2.4 km
  • Jensen’s Marina - 4 min drive - 2.7 km
  • McCarthy's Marina - 4 min drive - 2.7 km

Getting around

  • Fort Myers, FL (RSW-Southwest Florida Intl.) - 74 min drive

Restaurants

  • ‪The Green Flash Waterfront Restaurant - ‬3 min drive
  • ‪Starbucks - ‬5 min drive
  • ‪The Bubble Room - ‬4 min drive
  • ‪The Shipyard - ‬8 min walk
  • ‪The Mucky Duck - ‬4 min drive

Frequently asked questions

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.

How much does it cost to stay at Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch.?

As of 18 March 2026, prices found for a 1-night stay for 2 adults at Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. on 18 April 2026 start from NZ$1,651, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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 23 kg per pet.

How much is parking at Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch.?

On-site parking is available at the property.

What time is check-in at Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch.?

Check-in begins at 4:00 PM.

What time is check-out at Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch.?

Checkout is at 10:00 AM.

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

Situated in Captiva, this holiday 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 miles (3 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 25 out of 30 reviews
Rating 8 - Good. 5 out of 30 reviews
Rating 6 - Okay. 0 out of 30 reviews
Rating 4 - Poor. 0 out of 30 reviews
Rating 2 - Terrible. 0 out of 30 reviews

10/10

Cleanliness

9.6/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Matt H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property that is perfect for families. Thank you!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Charles Y.

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

Roosevelt Cottage

Our Family had a great time !
Verified

8/10 Good

Annie G.

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
Verified

10/10 Excellent

sarah d.

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
Verified

10/10 Excellent

Shelbie W.

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

Booked Again!

Wonderful property!!! Excellent location!!
Stayed 7 nights in Apr 2022
Verified

10/10 Excellent

Terri H.

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
From a partner site

10/10 Excellent

Cheryl Anderson

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).
Verified

10/10 Excellent

Karen H.

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
Verified

8/10 Good

Michele T.

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
Verified

10/10 Excellent

austin h.

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
Verified

10/10 Excellent

scott w.

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
From a partner site

8/10 Good

Mike Cardwell

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.
From a partner site

10/10 Excellent

Rich Gookin

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

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

10/10 Excellent

Megan S.

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
From a partner site

10/10 Excellent

charles canter

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
From a partner site

10/10 Excellent

Timothy Donnelly

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...
Verified

10/10 Excellent

Annie G.

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
Verified

10/10 Excellent

danica j.

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
Verified

10/10 Excellent

keith a.

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
From a partner site

10/10 Excellent

Lisa Leach

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.
From a partner site

8/10 Good

Ted Oberg

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.
From a partner site

8/10 Good

Karen Bloom

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.
From a partner site

10/10 Excellent

Charles Yanes

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.
Verified

10/10 Excellent

Kim B.

Excellent

It was a wonderful vacation & the property was beautiful
Stayed 8 nights in Mar 2019
Verified

10/10 Excellent

Jenny B.

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

About the host

Hosted by Sanibel Captiva Island Vacation Rentals

Host profile image
Sanibel Captiva Island Vacations is part of Sanibel Captiva Beach Resorts, a leader in Southwest Florida lodging management and marketing since 1931. Sanibel Captiva Beach Resorts offers outstanding beach resorts, vacation rentals, restaurant and entertainment venues, marinas, spa, plus recreational opportunities.

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