Top 10 Anna Maria Island Waterfront Rentals for Families

Looking for some rentals in Anna Maria Island right by the water? We are here to help! Below are the top 10 Anna Maria Island waterfront rentals suitable for the whole family.

anna maria vacation rentals

Waves Edge Anna Maria

We wouldn’t be surprised if at least a few of your family members spent the entire vacation lounging by this incredible pool admiring the water views from a stone’s throw away. It’s a massive space. This home offers 4 bedrooms, 3 bathrooms, and sleeps 8 guests with access to a shared heated pool, spa, outdoor shower, and other convenient amenities. This rental on Anna Maria Island is certainly one that stands out from the crowd.

rentals in Anna Maria Island

2810 Avenue E- North Side

This Holmes Beach duplex is fitted with everything you could ask for, including a bold patio overlooking the gulf, some nice furnishings, a bold and colorful style, and a huge king size bed in a master suite. The patio isn’t just near the beach- it’s on it. You can hear even the waves cascading through your windows.

beachfront homes for rent on anna maria island

2903 Avenue F

You will fall in love with the funky design of the bathroom and the incredibly spacious and open patio of our Avenue F waterfront property. Utilize a small flattened sand walkway to get right out to the water. If you want to get a nice elevated look, just pass the furnished kitchen and wind your way up the spiral staircase.

anna maria island vacation rentals

505 KEY ROYALE DR

This Anna Maria Island vacation rental has a spectacular pool and a hot tub fore relaxing in a screened porch. You can enjoy this four bedroom, four bath rental home set on the Wakins Bayou. You’ll family will love the tropical setting on the canal front with airy rooms, pool/ping-pong table, and just a short walk from the beach!

rentals in Anna Maria Island

Paradise

This cozy one-bedroom, one-bathroom is a delight. Take advantage of the fully-furnished kitchen, wall-mounted television, and cozy bedroom space. Spend your afternoons out in the shared-property heated pool or by the beach. You are only a few steps away.

beachfront homes for rent on anna maria island

Magnolia

The Magnolia is a fascinating and exquisite waterfront home. Its massive space gives you plenty of room to relax. You sit just down the street from the acclaimed and historic city pier. The location is great for water enthusiasts. You are right up against the canal.

holmes beach vacation rentals

Flotilla Dr Island

Three bedrooms, three bathrooms, and plenty of fun, the Flotilla Dr Island home boasts new appliances, an open patio space, and a tiki bar. Take a break from the bar to hang out in the pool in the private, fenced-in backyard.
Don’t forget your direct water access, anytime of the day.

anna maria waterfront vacation rentals

69th Street

This canal-front home was recently redone, top to bottom, making it possibly our freshest and most impressive property to date. Lounge out in a spacious seating area or utilize one of three en-suite bathrooms – one for each room.

beachfront homes for rent on anna maria island

Tree House

The delightful Tree House has views of the water from just about every angle. The large screened porch is just the place to hang out. You can dip to the top floor for some spectacular views or rest out on the open sun deck.

beachfront homes for rent on anna maria island

Hemingway’s Hideaway

Could we have saved the best for last? The past guests of Hemingway’s Hideaway would certainly say so.

This outstanding home sits right on the beach. The dining area is surrounded by big windows, so you can comfortably eat for the evening with the gulf as your backdrop – or just take your dinner party outside on the spacious patio.

Plan Your Visit

Our Anna Maria waterfront vacation rentals elevate your vacation getaway. It is more than just a place to stay. It is a full experience, and we provide the tools for a rewarding and whimsical tropical escape.