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 ordinary, 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 Property Alert! Rest A Shore is back and ready for rentals!If you’re looking for a getaway for a month or longer, th...
09/29/2026

New Property Alert! Rest A Shore is back and ready for rentals!

If you’re looking for a getaway for a month or longer, the Rest A Shore home could be your home away from home.

With 3 bedrooms, 2 baths and a pool, this darling bungalow has been tastefully updated and features an open-air sun deck with a grill, as well as a screened lanai overlooking the pool.

Rest A Shore is within walking distance of the beaches of Gulfside City Park, and the Sanibel Golf Club, nearby restaurants and shops are a short bike or car ride away.

🐾 A small non-shedding dog is welcome at Rest A Shore with owner approval and payment of a non-refundable pet fee.

πŸ“ž Call 239-472-6385 to book or click the link below to book online.

Rest Ashore: A Monthly Rental Near Beach Cottage on Sanibel IslandEnjoy true island-style living at Rest Ashore, one of Sanibel Island's original near...

Four years ago today, Hurricane Ian changed Sanibel forever. 🌊Our homes, our businesses, our favorite spots β€” so much of...
09/28/2026

Four years ago today, Hurricane Ian changed Sanibel forever. 🌊

Our homes, our businesses, our favorite spots β€” so much of it was gone overnight. And yet here we are. Perspective is everything. We're still rebuilding properties, and we're EXCITED.

We've shared a few "before" and "current situation" photos to show that progress does take time, and it is worth the wait.

Today we're not marking what we lost. We're celebrating everything that brought us back:
πŸ’› Neighbors who showed up with chainsaws, hurricane rations, and hugs
πŸ’› Homeowners who trusted us to help them rebuild
πŸ’› Guests who kept asking "When can we come back?" (answer: NOW!)
πŸ’› The crews, volunteers, first responders and city officials who never quit
πŸ’› An island that refused to be anything but beautiful

The sunsets never left. Neither did we.

Thank you for standing with Sanibel and Captiva. πŸ™

What's YOUR favorite Sanibel comeback moment?

Cancellation Alert: The Blue Pelican is a forever favorite of many of our longtime guests, and it has just become availa...
09/24/2026

Cancellation Alert:

The Blue Pelican is a forever favorite of many of our longtime guests, and it has just become available for the Winter 2026 season. Enjoy the beaches, neighborhood, wildlife and the Sanibel Sanibel Island Farmers Market during your Sanibel getaway.

βœ“ 28 night minimum stay required
βœ“ Pet Friendly 🐾
βœ“ 3 bedroom, 3 bath - perfect for couples & families
βœ“ Grill
βœ“ Walking distance to Bowman's Beach
βœ“ Hi speed Wi-fi
βœ“ Community Pool, Tennis next door
βœ“ Heart of Captiva = 5 miles
βœ“ Heart of Sanibel = 5 miles

This property won't be available for long!
Book at the link below or πŸ“ž 239-472-6385 | 800-472-5385

Blue Pelican: Your Sanibel Island Sanctuary~Discover Your Perfect Island Retreat~Imagine waking to the sound of gentle waves and tropical birds,...

Day  #1452:The fabulous and newly reimagined pool at Tarpon Beach Condominiums is OPEN!Featuring a Malibu ledge for easy...
09/19/2026

Day #1452:

The fabulous and newly reimagined pool at Tarpon Beach Condominiums is OPEN!

Featuring a Malibu ledge for easy entry and a chair lift for those requiring assistance, this pool features the best of the best.

20 chaise lounges and multiple tables and chairs are available for relaxing on the oversized deck, along with Tuuci umbrellas for when you’d like a little shade.

Book your getaway now πŸ—“οΈπŸ“ž239-472-6385 | 800-472-5385
www.Cottages-to-Castles.com

09/11/2026

Waves of Remembrance.

No day shall erase you from the memory of time. - Virgil
πŸ‡ΊπŸ‡ΈπŸ‡ΊπŸ‡ΈπŸ‡ΊπŸ‡ΈπŸ‡ΊπŸ‡ΈπŸ‡ΊπŸ‡Έ

Attention All Shellers! Have a Shelluva Time planning your day around the best time to shell on Sanibel and Captiva Isla...
08/18/2026

Attention All Shellers!

Have a Shelluva Time planning your day around the best time to shell on Sanibel and Captiva Islands with this fabulous new page created by Rachel Pierce (and family)!

Bookmark the site on your phone, tablet or computer, grab your mesh shelling bag and warm up by doing 3 sets of 10 Sanibel Stoops to prepare!

The best beach and time window for shelling on Sanibel and Captiva today, from NOAA tide predictions derived for our amazing beaches.

It's National Lazy Day! It's National Lazy Day, so we're celebrating by sharing our two favorite Lazy things on Sanibel....
08/10/2026

It's National Lazy Day!

It's National Lazy Day, so we're celebrating by sharing our two favorite Lazy things on Sanibel.

First up: Did you know our Lazy Ray Retreat- home was featured on HGTV's House Hunters this past May? It's already become a guest favorite with its comfy indoor outdoor living spaces, easy access to the West Gulf Drive beaches and proximity to restaurants, the refuge and more.

While you're on island, be sure to stop in to the Lazy Flamingo 2 and enjoy their famous conch fritters, grouper sandwich or catch of the day, beans and rice and a cold beverage!
🏑🦩

πŸ“ž Book the Lazy Ray by calling 239-472-6385 or toll-free 800-472-5385

Here's a secret the crowds haven't caught onto yet: late summer and fall are the BEST time to book Sanibel & Captiva. 🌴W...
07/25/2026

Here's a secret the crowds haven't caught onto yet: late summer and fall are the BEST time to book Sanibel & Captiva. 🌴

Warmer Gulf water. Quieter beaches. Better rates. And still every bit of the island magic β€” sunset shelling, dolphins cruising the shoreline, and that first cocktail on the lanai that makes you exhale for the first time in months.

We've still got open dates this season and we'd love to get you here. Which island memory are you overdue for β€” shelling, sunsets, or just doing absolutely nothing? Tell us below. πŸ‘‡

Call πŸ“ž 239-472-6385 | 800-472-5385 or click the website link in comments.

🌊 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.

πŸ›οΈ 2 Bedrooms / 2 Bathrooms β€” Sleeps 4 -6
🏊 Community pool, tennis & BBQ grills
🍳 Full kitchen, in-unit washer/dryer, free Wi-Fi
πŸŒ… Gulf-front with gorgeous water views
πŸ–οΈ Sanibel is waiting for you.

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

Sanibel Surfside 117 is a 2-bedroom / 2-bathroom Gulf-front condo on Sanibel Island with fantastic views. Within the beautiful ocean-style dΓ©cor 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 β€” including the simple joy of a beautiful day by the water.





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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