Escape to Summerland Key with beautifully appointed vacation homes steps from the Gulf of Mexico. Wake to turquoise water, spend your days exploring island life, and let every evening end with a Keys sunset that takes your breath away.
From the moment you arrive, we take care of the details so you can focus on what matters — making memories with the people you love.
Our homes sit on the quiet side of Summerland Key, with direct access to the calm, crystal-clear waters of the Florida Bay and Gulf of Mexico.
Fully furnished kitchens, comfortable living spaces, and thoughtful touches that make every stay feel personal — not like a hotel room.
Whether you're planning a long weekend or a week-long island retreat, our rental options fit your schedule and your group size.
Right in the heart of the Keys, yet tucked away on a peaceful street. Key West, Dry Tortugas excursions, and local restaurants are all nearby.
We're local hosts who genuinely care about your experience. From check-in guidance to insider recommendations, we're here for you.
Professional cleaning between every stay, fresh linens, and regularly maintained properties — because your comfort is non-negotiable.
Captains and Mermaids Keys Rentals started with a simple belief: the best vacations feel like coming home to somewhere extraordinary. We fell in love with Summerland Key — its slow pace, its salt-kissed air, its legendary sunsets — and we wanted to share that feeling with you.
Each of our vacation rentals is thoughtfully furnished and designed to give you the full island experience — comfort, character, and a front-row seat to Keys living.
Waterfront
A cozy two-bedroom cottage with direct bay access, a private patio, and all the charm of island living.
Popular
A spacious three-bedroom villa with a screened pool, open kitchen, and wide lanai perfect for evening gatherings.
New
Our newest addition — a modern two-bedroom home with a private dock, stunning bay views, and a chef-inspired kitchen.
Summerland Key is your gateway to some of the most unforgettable adventures in the Caribbean's backyard.
World-class reefs just minutes from our doors. The Florida Keys Reef Tract is one of the few barrier reefs in the continental U.S.
Chart a boat from nearby marinas and chase tarpon, snook, mahi-mahi, and more in the warm Gulf waters.
From Siesta Key to quieter hidden spots, the Keys' beaches are some of the softest, whitest sand on the planet.
Take a seaplane or ferry to Fort Jefferson and one of the most remote, beautiful national parks in the country.
The best part of hosting isn't the beautiful homes — it's the stories our guests bring back from the Keys.
We've stayed at resorts all over the Keys, but nothing compares to the feeling of coming back to our own little home on Summerland Key. The sunset views from the patio were absolutely magical every single evening.
Three generations of our family spent a week here and there was something for everyone. The kids loved the water, my parents loved the quiet, and I just loved not having to deal with a hotel lobby. Truly a home away from home.
From the moment we arrived, everything was seamless. The home was spotless, the directions were clear, and the recommendations for local restaurants were spot on. We're already planning our return trip.
Tell us when you'd like to come, how many are traveling, and what kind of experience you're looking for. We'll find the perfect home for your group.
Have a question about a property, need travel advice, or ready to book? Reach out however you're most comfortable.
27396 Dominica Ln
Summerland Key, FL 33042-5453
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