From Simple to Simply Elegant

Cottages to Castles represents unique privately owned cottages, condominiums, homes and estates on the Islands.

Since 1997, our boutique vacation rental agency has been providing personalized service to help our guests find their home away from home and create memories to last a lifetime. Each year, Cottages to Castles welcomes families and friends from around the world to these idyllic, scenic and tranquil islands. With sandy beaches, world-class fishing, shelling, bird watching, shopping, galleries, restaurants, live theater – and more – Sanibel and Captiva are your paradise without a passport.

Quality and value go hand-in-hand, and we recognize that your vacation time is valuable. We strive to provide you with peace of mind by providing a level of service and properties that will exceed your expectations. Won’t you come and join us?

Immerse yourself - The home away from home you select is thoughtfully appointed and designed for comfort and style. Your vacation should be as comfortable as it is memorable. Can’t find what you’re looking for? Contact us and we’ll work with you to find your dream vacation property.

Effortless relaxation - Experience a hassle-free stay with seamless check-in, personalized communication, and a dedicated team to assist you in planning your getaway so that you can focus on what matters - creating lasting memories.

Trusted Local Connections - We believe in community, and as our guest, you’re part of it. We are committed to you and will work to connect the dots prior to and during your stay to ensure that it is a memorable one for all of the right reasons. You will receive a custom Insiders Guide that will have you living like a local in no time, whether you’re here for a week, a month, or longer. Explore, dine and stay where we do!

Learn More About Us

List Your Property With Us

AN OWNER FIRST FOCUS: Cottages to Castles was founded on the idea that if we collaborate with and take excellent care of our Owners and their properties, the guests will follow and the revenue will flow. We take our business with you personally, and this “Owner-first” focus is at the core of the property management services we provide. Our reputation relies on it.

SIMPLIFY YOUR LIFE: We put the “IT” in Hospitality. As the trusted on-island full-service vacation rental company, we provide you with a turnkey booking solution, dedicated Owner Portal, streamlined communication and integrated technology, along with enhanced income opportunities. In addition, we are able to coordinate project management/interior design/construction services, real estate services and disaster recovery efforts on your behalf.

QUALITY vs QUANTITY: We are able to provide the legendary service and personalized attention that we are known for and that your property requires because we are a small company with a limited and balanced property portfolio. Let’s Do This Together. It’s What We Do.

learn more about property management

What Our Guests Say

Wonderful Memories

Thanks so much for making our vacation wonderful. The condo has served us well, comfy and good location. We’ve been pleased with the crew at Cottages To Castles! Cheers!
Perfect. Just Perfect

This condo is beautiful, spacious, comfortable, and ideally located. With the elevator right at the parking space, it is easy to move in. With a fully stocked beach closet with chairs, umbrellas, and other beach/pool items, we were able to enjoy the beach immediately upon arrival. We spent a lot of time on the lanai and enjoyed the views, the breeze, and the sunsets. We are looking forward to booking again!
Great Stay

Thanks for the wonderful stay. Sharon at Cottages To Castles is wonderful. This is great location and your condo is so well equipped. My husband even made chocolate chip cookies from scratch! This is a great place, thanks for sharing.