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Interior of vacation rental in Islamorada

Introducing The Maison, Mainsail’s Luxury Islamorada Vacation Rentals

On your next Islamorada vacation, select only the best luxury vacation rental to call your home– The Maison. You’re sure to find Islamorada to be a great place to relax, unwind and reconnect with family and friends, and our luxury... Read more
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Introducing Mello on the Beach, Our Latest Anna Maria Island Vacation Rental

You’ve got lots of options when it comes to choosing an Anna Maria Island vacation rental. But when you want an upscale vacation rental filled with all the luxurious amenities you could ask for, look no further than Mello on... Read more
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Book Your Anna Maria Island Vacation with Confidence When You Purchase Travel Insurance

Whether you’re taking a trip across the country or just driving across Florida, anything can happen before your vacation. You can get sick, natural disasters can strike, or family emergencies can happen. You don’t want to cancel your vacation, but... Read more
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Holiday Festivities in Anna Maria Island

Will you be home for Christmas, or are you planning to spend the holidays on spectacular Anna Maria Island? There are plenty of festive Anna Maria Island events you can enjoy. There are many wonderful places to stay in Anna... Read more
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3 Reasons Why You Should Visit Anna Maria Island in the Off-Season

When thinking of how to save money on an Anna Maria Island vacation, consider visiting us in the off-season. You’ll be able to spend some time on the amazing island, enjoying the amazing Anna Maria Island weather even if it’s... Read more
anna maria island beach path

Mainsail Supports Love it Like a Local

It’s true when they say Anna Maria Island is more than a vacation destination; it’s a home. Whether staying year-round or visiting for a weekend during the summer, Anna Maria Island is cherished by hundreds of thousands of people for... Read more
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How to Navigate Around Anna Maria Island

Anna Maria Island is one of the most underrated vacation spots in Florida, but if you’re looking for a relaxing getaway, you want to know about this place! The island is just seven miles long, but there are lots to... Read more

Scuba Diving Near Anna Maria Island – How, Why, and Where

If you’re planning to book an Anna Maria Island vacation rental for your next family trip, you’re likely looking to spend lots of time in the water. But you don’t have to stick with fishing, swimming, or boating to get... Read more
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Why Anna Maria Island is Ideal for Family Vacations

Looking for a family vacation destination in Florida? Anna Maria Island is the perfect spot. It is significantly less crowded than other Florida cities like Tampa or Orlando, so you’ll truly get to relax on your getaway. You’ll be greeted... Read more
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Travel Information: COVID-19 Response

The wellbeing of our guests and associates is of paramount importance. Take the risk out of booking with more control and flexibility. Mainsail Vacation Rentals is committed to your safety and experience. We are closely monitoring the Centers for Disease... Read more

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