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

Captiva vacation home with private pool

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

5 bedrooms, iron/ironing board, WiFi, bed sheets
A heated pool
Exterior
Fridge, oven, stovetop, dishwasher
Flat-screen TV, DVD player

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 12

Popular amenities

  • Pet friendly
  • Parking available
  • Dryer
  • Washer
  • Pool
  • Kitchen

Explore the area

View in a map
Captiva, FL
  • Place, Captiva Beach
    ‪1 min walk‬
  • Place, J. N. Ding Darling National Wildlife Refuge
    ‪1 min drive‬
  • Place, Jensen’s Marina
    ‪4 min drive‬
  • Airport, Fort Myers, FL (RSW-Southwest Florida Intl.)
    ‪62 min drive‬

Room options

About the neighborhood

Captiva

In Captiva .Within a 10-minute walk of the vacation home, you'll find 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).
View more Vacation Homes in CaptivaOpens in a new window

What's nearby

  • Captiva Beach - 1 min walk - 0.1 miles
  • J. N. Ding Darling National Wildlife Refuge - 1 min drive - 0.2 miles
  • Captiva Chapel By the Sea - 3 min drive - 1.5 miles
  • Jensen’s Marina - 4 min drive - 1.7 miles
  • Jungle Drums - 4 min drive - 1.9 miles

Getting around

  • Southwest Florida Intl. Airport (RSW) - 74 min drive

Restaurants

  • ‪Starbucks - ‬5 min drive
  • ‪The Green Flash Waterfront Restaurant - ‬3 min drive
  • ‪The Shipyard - ‬8 min walk
  • ‪RC Otter's Island Eats - ‬4 min drive
  • ‪The Mucky Duck - ‬4 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.



Please Note: Captiva Island is scheduled to undergo a beach renourishment project which may begin 9/1 at Blind Pass and move north through 10/31 that may result in temporary beach access limitations, construction activity, or noise near your property. While we strive to provide accurate updates, timelines and impacts are subject to change and beyond our Sanibel Captiva Island Vacations control.



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.

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Property amenities

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: WiFi (surcharge)

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Dishwasher
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 private bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • DVD player
  • Flat-screen TV

Outdoor areas

  • Barbecue grill
  • Dock
  • Fenced yard
  • Garden
  • Lanai

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Housekeeping (limited availability)
  • Iron/ironing board
  • Phone

Things to do

  • Fishing
  • Heated pool
  • Hiking/biking trails nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Check-out instructions

The host requires you complete the following before checking out:
Load the dishwasher
Strip any used beds and gather used towels
Remove personal items and take out the trash
Turn off the lights
Failure to complete these may result in a negative review from the host.

Rules

100% refund if reservation is cancelled at least 60 days before the arrival date

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Property is also known as

Bayfront Captiva Home Private Beach Access Pool/dock House
Bayfront Home Private Beach Access Pool/dock House
Bayfront Captiva Home Private Beach Access Pool/dock
Bayfront Home Private Beach Access Pool/dock
Bayfront Captiva Home Private Beach Access Pool/dock House
Bayfront Home Private Beach Access Pool/dock House
Bayfront Captiva Home Private Beach Access Pool/dock
Bayfront Captiva Home Private Beach Access Pool/dock House
Bayfront Home Private Beach Access Pool/dock House
Bayfront Captiva Home Private Beach Access Pool/dock
Bayfront Captiva Home With Private Beach Access Pool/dock
Bayfront Home Private Beach Access Pool/dock
Bayfront Captiva Home With Private Beach Access Pool/dock
5 bedroom accommodation in Captiva Captiva
5 bedroom accommodation in Captiva Private vacation home
Bayfront Captiva Home With Private Beach Access Pool/dock
5 bedroom accommodation in Captiva Private vacation home Captiva
7899-231569

Frequently asked questions

How close is Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. to the airport?

This vacation home is 36.5 mi (74-min drive) away from the Southwest Florida Intl. Airport (RSW) airport, the closest popular airport to the property.

Does Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. to the beach?

This vacation home is a short 3-minute walk from Captiva Beach and 5.8 mi (13-min drive) from Sanibel Island Southern Beach. Don't forget your sunscreen!

Does Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch.?

No, there is no casino at this vacation home.

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

Check-in begins at 4:00 PM.

Is there free parking at Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch.?

Free parking is not available at this vacation home.

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

Yes, there's a private pool.

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

There are no spa services available at this vacation home.

How close is Roosevelt Cottage | Gulf to Bay Getaway Along Captiva 'Tween Waters Stretch. to downtown Captiva?

This vacation home is 1.1 mi away from Captiva.

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

Reviews

9.8

Exceptional

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

Reviews

10/10 Excellent

Matt H.

Liked: Cleanliness
Great property that is perfect for families. Thank you!
Stayed 7 nights in Jul 2025

8/10 Good

Annie G.

Liked: Cleanliness

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

Shelbie W., Leesburg, FL

Liked: Cleanliness

Booked Again!

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

10/10 Excellent

Terri H.

Liked: Cleanliness

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

10/10 Excellent

Karen H.

Liked: Cleanliness

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

Liked: Cleanliness

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

Liked: Cleanliness

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.

Liked: Cleanliness

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

10/10 Excellent

Megan S.

Liked: Cleanliness

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

10/10 Excellent

Annie G.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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

10/10 Excellent

Charles Y.

Liked: Cleanliness

Roosevelt Cottage

Our Family had a great time !

10/10 Excellent

Kim B.

Excellent

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

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

10/10 Excellent

Jenny B., Knoxville, TN

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