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

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Flat-screen TV, DVD player
A heated pool
Exterior
Marina
Fridge, oven, stovetop, dishwasher

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 12

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning

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.)
    ‪61 min drive‬

Room options

About the neighborhood

Captiva

With a stay at this vacation home in Captiva, you'll be on the waterfront, within a 15-minute drive of Sanibel Island Southern Beach and Captiva Beach. .This vacation home is 0.3 mi (0.5 km) from J. N. Ding Darling National Wildlife Refuge and 1.1 mi (1.8 km) from Captiva Chapel By the Sea.
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
  • McCarthy's Marina - 4 min drive - 1.7 miles

Getting around

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

Restaurants

  • ‪The Green Flash Waterfront Restaurant - ‬3 min drive
  • ‪The Bubble Room - ‬4 min drive
  • ‪American Legion Post 123 - ‬14 min drive
  • ‪The Mucky Duck - ‬4 min drive
  • ‪Starbucks - ‬5 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.

INTRODUCING ROOSEVELT COTTAGE — A GULF‑TO‑BAY CAPTIVA ESTATE OF PURE ISLAND LUXURY



Tucked along one of Captiva’s most coveted stretches of Gulf‑to‑Bay shoreline, Roosevelt Cottage is a rare island estate offering timeless charm, modern comfort, and an unforgettable resort‑style experience. With nearly 5,000 sq ft of beautifully designed living space across three separate structures, this property is made for extended families, multi‑generational groups, and anyone seeking a private, peaceful slice of Captiva magic.



HOME FEATURES

Elegant, Expansive and Designed for Gathering.

The main home welcomes you with an open, airy floor plan that blends coastal sophistication with relaxed island living. A spacious living area flows seamlessly into the chef’s gourmet kitchen, complete with upscale appliances, a 4‑burner gas range, and a sunny breakfast nook perfect for slow mornings.



PRIMARY KING SUITE RETREAT

The northern wing of the main house features a serene primary king suite with:

• A luxurious ensuite bathroom with claw‑foot soaking tub and walk‑in shower

• A generous walk‑in closet

• A private office/den with TV and half bath — ideal for quiet work or relaxation



UPPER‑LEVEL LOFT + GUEST BEDROOMS

The upper level offers a spacious loft with a queen sleeper sofa and flat‑panel TV — a perfect hangout zone for kids or teens. On each side of the loft, you’ll find beautifully appointed queen guest bedrooms, each with access to a full bathroom featuring a tub/shower combination.



GUEST COTTAGE

Once the original fishing cottage on this tropical estate, this charming standalone retreat includes:

• A cozy living area with TV and WiFi

• A fully equipped kitchen (refrigerator, stove, microwave)

• Dining area

• King bedroom

• Full bathroom

• Private washer/dryer

It’s the perfect hideaway for guests seeking extra privacy and old‑Florida charm.



CARRIAGE HOUSE KING SUITE

Located above the garage, this spacious suite offers:

• A king bed

• Full bathroom

• Comfortable seating area with flat‑screen TV

• Morning kitchen for added convenience

Ideal for couples or guests who enjoy their own quiet corner of the estate.



GULF‑TO‑BAY LIVING AT ITS FINEST



DEDICATED ON‑SITE PROPERTY MANAGER

Enjoy true peace of mind with a professional on‑site property manager available throughout your stay. From coordinating requests to offering local insight and ensuring everything runs seamlessly, guests receive attentive, concierge‑style support from the moment they arrive.



PRIVATE HEATED POOL OASIS

Hidden among lush, mature tropical landscaping, the private heated pool feels like a secluded resort. A cascading waterfall adds to the ambiance, creating a serene retreat for sunbathing, swimming, or unwinding after a day on the water.



PRIVATE DOCK & FISHING PIER ON ROOSEVELT CHANNEL

Step onto your expansive screened lanai and out to your private dock overlooking the tranquil Roosevelt Channel. Perfect for:

• Fishing at sunrise

• Watching dolphins and manatees glide by

• Launching kayaks or paddleboards

• Docking a rental boat for island‑hopping adventures

This is true bayside living — peaceful, scenic, and endlessly relaxing.



EASY GULF ACCESS

With Gulf beaches just moments away, you’ll enjoy the best of both worlds: calm bay waters for wildlife and boating, and soft white sand for swimming, shelling, and sunset strolls.



FULL ACCESS TO 'TWEEN WATERS ISLAND RESORT & MARINA

Located just 0.1 miles from the resort, Roosevelt Cottage guests enjoy access (based on availability) to:

• Two resort pools

• Restaurants & bars and more



THE CAPTIVA EXPERIENCE

Roosevelt Cottage is a true hidden gem — a place where families reconnect, friends unwind, and every day feels like a postcard. From peaceful mornings on the dock to sunset walks on the Gulf, this estate offers a rare combination of luxury, privacy, and authentic island charm.



HAVE QUESTIONS?

Call the Sanibel Captiva Island Vacation Rentals Team for more information, including local vendors for bicycles, baby gear, and more.
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Wireless internet access (surcharge) keeps you connected, and a DVD player is provided for your entertainment.
Take in the views from a garden and make use of amenities such as barbecue grills.
Guests will find features like wireless internet access and onsite parking.

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
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • 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

  • Air conditioning
  • Heating

Pets

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

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • On a lake
  • On a river
  • On the waterfront

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: 18

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
Information provided by the property may be translated using automated translation tools

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 allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 50 lbs per pet)

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

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

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 25 out of 31 reviews
Rating 8 - Good. 6 out of 31 reviews
Rating 6 - Okay. 0 out of 31 reviews
Rating 4 - Poor. 0 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

9.8/10

Cleanliness

Reviews

8/10 Good

J David C., Longmont, CO USA

Liked: Cleanliness
-Kitchen equipment needs updating (pots/pans/utensils/hot pads and mittens)-wood decking needs either refinishing or replacement. Dangerous on bare feet with splinters and exposed nails. -doors need new locks and hinges-room above garage needs updating and new carpet (torn/moldy)-alarm system malfunctioningGreat location, great property overall. Would stay again, but for the price expect fine-tuning the issues noted
Stayed 7 nights in Mar 2026

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