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Book Your Gulf Coast and Bahamas Vacation In Confidence

Our Top Priority is the Well Being of Our Guests. Click Here to Learn More about our Commitment to Safe Cleaning and our Flexible Cancellation Policy.

Welcome To Mainsail Vacation Rentals

A Family-Friendly Beach Vacation Awaits

Enjoy more than just a simple beach vacation when you book a condo or house rental with Mainsail Vacation Rentals. We provide quality, comfort, and accessibility to all so you can take the vacation you deserve without having to empty your wallet. From Beachfront Condos to Houses with private boat docks all the way to our Resort Property in The Bahamas, our vacation rentals offer more than just a place to rest your head.

Our inventory includes 2-Bedroom Condos and 3-Bedroom Condos located in Holmes Beach, FL, or you can check out our 2-Bedroom House in Sarasota or our 3-Bedroom House in Bradenton. If you want to spread your wings and really take in the 5-Star, VIP experience, then check out the Ole Ike Bay Resort Property in The Bahamas!

There is never a dull moment when you stay in a Mainsail Vacation Rental. With all the local shopping, exquisite dinning, and fun-filled attractions, Anna Maria Island will provide memory after memory for you and your guests. The Bahamas Resort, Ole Ike Bay can accommodate up to 9 guests and offers 3.5 acres of seclusion surrounded by miles of crystal-clear Atlantic water.

Take the vacation you and your family deserve! Welcome to Mainsail Vacation Rentals, your Gulf Shore and Atlantic Ocean Vacation headquarters. 


Things To Do



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  • We rented a three bedroom and a two bedroom condo on the first floor with the bigger one facing the beach. It was beautiful to watch the glorious sunsets each evening

    - Judith T.

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  • We stayed on the 3rd floor in unit 7. The condo was clean, spacious and had everything we needed. The ocean view was the highlight of this condo. Matthew was amazing and so helpful. The location was easy to get to anywhere on the island. The beach and sand are right out your backyard which made it so easy to get on the beach. Highly recommend this place!

    - Anonymous

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  • Had a terrific time. Everything about the Mainsail exceeded our expectations.

    - Anonymous

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  • wonderful location and very clean. The only complaint was the outside deck. Horrible condition and also the furnature needed painting. That would make a big difference.

    - Susan T.

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Property Management

Our fantastic marketing and direct booking process means you can spend less time worrying, and more time relaxing.

See How Easy It Can Be!
AMI Chamber of Commerce

CONTACT US

Mainsail Vacation Rentals
5325 Marina Drive,
Holmes Beach, FL 34217
866-724-5287

PROUD PARTNER

Homes & Villas by Marriott International

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