News

Baseball field on Anna Maria Island

Don’t Miss Spring Training this February in Anna Maria Island

There are plenty of things to do while visiting the area, like Anna Maria Island boat tours and the local parks on AMI, but if you are staying in one of our Anna Maria Island vacation rentals this February, you... Read more
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
ami park by the water

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
travel insurance papers, a pen, and other travel necessities

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
couple on the beach at anna maria island

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
Couple walking on Anna Maria Island Beaches

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
girl by the ocean

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
a rack full of kayaks and canoes

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

CONTACT US

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

PROUD PARTNER

Homes & Villas by Marriott International

RESOURCES

Terms & Conditions
Travel Insurance
Area Info
Homeowner Benefits
Owner F.A.Q
Guest F.A.Q
Mainsail Beach Inn
Mello on the Beach
Waterline Villas & Marina
Rentals A-Z
Diversity
Careers

CONNECT

Sign up for our newsletter for access to our latest specials and updates.
  • This field is for validation purposes and should be left unchanged.

HAVE A QUESTION?
Contact Us
© Copyright 2025 Book with Confidence | Mainsail VR | Privacy Policy | Website Accessibility Policy | Website managed by RealTech Webmasters