Cottages to Castles of Sanibel & Captiva, Inc.

Cottages to Castles of Sanibel & Captiva, Inc. From simple to simply elegant, we offer the finest cottages, condominiums & homes for rent on Sanibel.

Founded in 1997 as the island’s original boutique agency, we connect the dots to ensure your vacation is memorable for all of the right reasons We are the original Islander-owned vacation rental agency on Sanibel & Captiva Islands, and we've been connecting the dots to make memorable vacations for guests and owners for over 20 years. From Simple to Simply Elegant, we bring the extra to the ordinar

y, and represent the most unique cottages, condominiums, homes and estates available for rent on Sanibel & Captiva Islands. Our Properties have been featured on MTV, HGTV's Dream Vacations and in Martha Stewart 'Living'. Our properties are available for rent daily, weekly, monthly and seasonally. They are ideal for families, romantic getaways, corporate retreats, weddings and events.

🌊 New Listing Alert: Sanibel Surfside 117! 🌊We're excited to offer this stunning Gulf-front condo to you. Gulf-front. Tw...
06/20/2026

🌊 New Listing Alert: Sanibel Surfside 117! 🌊

We're excited to offer this stunning Gulf-front condo to you.

Gulf-front. Two private lanais. A view that makes you forget what day it is. 🌊

This one is perfect for the family trip you've been promising everyone, the milestone birthday that deserves a beach backdrop, or the babymoon/anniversary that you're excited to plan.

🛏️ 2 Bedrooms / 2 Bathrooms — Sleeps 4 -6
🏊 Community pool, tennis & BBQ grills
🍳 Full kitchen, in-unit washer/dryer, free Wi-Fi
🌅 Gulf-front with gorgeous water views
🏖️ Sanibel is waiting for you.

📅 Click on the photo below to book your stay now, or call us at 239-472-6385 | Toll-free 800-472-5385 📞

Sanibel Surfside 117 is a 2-bedroom / 2-bathroom Gulf-front condo on Sanibel Island with fantastic views. Within the beautiful ocean-style décor you'll find tile...

05/25/2026

On this Memorial Day, we pause to honor the brave men and women who gave everything to protect the freedoms we cherish — including the simple joy of a beautiful day by the water.





We’re blushing 😊
05/24/2026

We’re blushing 😊

A HUGE Thank you to everyone who watched our episode of House Hunter’s last night! It was our first time viewing it, too! We are incredibly grateful to own a small part of this special island. I am so glad that there was a glimpse of our boys painting their shells included in the episode!!

Susan Ives with Premier Sotheby’s of Sanibel was our realtor, and we cannot praise her enough. She has spent her whole life on Sanibel/Captiva and has such expansive knowledge of the island real estate market. She hustled to make the deal happen, and she is now our forever friend!

The custom art at the reveal at the end was done by an incredibly talented artist based out of Seattle, Washington named Blake Blanco. He listened to our vision of the piece and brought it to life. He is an awesome human being and friend on top of it all! He ships his art all over- so don’t be deterred by the distance! We have had the opportunity to view his work in person at galleries in Seattle, and honestly the pictures don’t do it justice. My favorite part about his art besides the vibrant colors is how he incorporates real material objects into it. https://www.blakeblanco.com

Sharon Michie at Cottages to Castles of Sanibel & Captiva, Inc. is an absolute gem. We have rented through Cottages in the past and had such wonderful experiences that we knew we wanted to have her as our property manager. As soon as we started our search, Sharon was a wealth of knowledge for us. She sat with us for hours in her office off of Periwinkle discussing the properties, their rental attributes, and THE SPREADSHEETS! She also put her boots on and went under the crawlspace of the house to make sure there weren’t any hidden issues! This was all before we had even signed a contract with her. She genuinely just wanted the best for us and our future Sanibel investment! As soon as we closed on the house Sharon and her assistant Deanna went to work marketing it, helped us decorate, and made it the perfect vacation spot. SHE HAD IT BOOKED WITHIN WEEKS! Those two women never stop hustling to help us keep it rented so that we can afford it! Also, the original fridge broke within a few weeks of taking ownership. Poor Sharon and Deanna cleaned out defrosted frozen bait and our beloved, melted stash of The Shack of Sanibel frozen custard without skipping a beat! If you need a rental or need to rent out a property- call them!!!!

Thank you to The City of Sanibel, Florida for allowing us to film and supporting our little adventure! I got to have a call with Eric Jackson, the Public Information Officer, who was a delight to speak with!

Thank you to Tiffany at the Sanibel-Captiva Islander | Island Reporter | Captiva Current for taking the time to interview us and write that beautiful article! You captured our journey perfectly!

And of course- thank you to Magic Bus on Sanibel and The Sanibel Sprout for fueling my iced coffee addiction!

05/24/2026
Did you choose the Lazy Ray Retreat for the win?!Share your favorite moments of the show with us!If you’d like to experi...
05/24/2026

Did you choose the Lazy Ray Retreat for the win?!

Share your favorite moments of the show with us!

If you’d like to experience the Lazy Ray Retreat, book your stay here:

https://www.cottages-to-castles.com/

It’s almost showtime!
05/24/2026

It’s almost showtime!





Are you ready for it? Stay tuned…
05/24/2026

Are you ready for it? Stay tuned…

It's official! Spread the word, set your DVR and tune in to HGTV's "House Hunters" on May 23 at 10pm EST to follow the R...
05/19/2026

It's official!

Spread the word, set your DVR and tune in to HGTV's "House Hunters" on May 23 at 10pm EST to follow the Ray family as they find their forever Sanibel home.

This episode has all the feels 💓

🌺👣🚴‍♂️🐬🐚⛺️🏡🏫

05/18/2026

We are getting hyped for the premier of the Sanibel episode of HGTV's House Hunters this Saturday at 10pm EST, so we thought we'd do a throwback to an episode we filmed with HGTV back in 2015 at our Point of View home.

This fabulous home was featured on the series "Vacation House For Free" back in 2015, Season 2, Episode 2. It was referred to as the "Seaside Sentiment" property for the show.

While Point of View did sustain damage in Hurricane Ian, she has been put back together as good as new and is almost ready to welcome returning guests. Stay tuned for booking information.

Please enjoy watching "Sanibel Sanctuary," and keep an eye out for glimpses of the The Island Cow and other island favorites.

Click the link below to watch!

Address

2427 Periwinkle Way
Sanibel, FL
33957

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm
Saturday 9am - 5pm

Telephone

+12394726385

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