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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 had a wonderful stay at Mainsail. Located just steps from the beach was heaven! The 3 BR townhouse was extremely clean with the cutest decor. The kitchen had everything we needed for our stay and the bathroom amenities were helpful too. I wish all rooms had queen or king beds (vs. a full in one) and wish the upstairs seating was a bit more comfortable. But this truly was a wonderful place to stay. The staff was so incredibly friendly and helpful and the location by the trolley stop made getting around without a car so easy. I would absolutely recommend Mainsail and hope to stay there again some day!

    - Sarah B.

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  • Just returned from our second trip to Mainsail. It really is a special place. We stayed in Unit 7 this time having stayed in Unit 8 last time. Both are top floor beach front with beautiful views. Accommodations are extremely clean and equipped with everything you could need. The setting right on the beach is just wonderful and the sunsets are incredible. Staff very friendly. Great easy check in / out system,loved the digital code instead of a key. Lots of great places to eat near by, Slims Place & Pizza Social we’re favs. This place has it all. Anna Maria Island is a very beautiful quiet place we would highly recommend. Will definitely be back.

    - Andrea L.

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  • We loved the wood floors and the “homey” feel of the inside. Unit 9 was very spacious and the 2 balconies were wonderful. Bev went above and beyond to help....examples, she not only unlocked the chairs, she took one all of the way down to our area. The next day, she came to check on the guests who were at the beach.

    - Robyn H.

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  • We were in Unit 2, beachfront, main floor 2/2. Everything was wonderful! Matthew and Rhoda were fantastic hosts. Location is incredible, right on the beach, between the two main pier restaurant/shop areas. We loved riding the bikes and using the paddleboards. The chairs and umbrellas were perfect for everyday use and it was nice to have to pool for a dip when we had enough salt water! We would 100% stay here again!

    - Christine M.

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Property Management

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CONTACT US

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

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Homes & Villas by Marriott International

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