Anna Maria Island Rentals That Will Make You Want to Drop Everything

You’ve got your vacation destination in mind: Anna Maria Island, Florida.

Yet you might be struggling to find places to stay which have that good ol’ Florida appeal. If that’s the case, Anna Maria’s northern tip has some stunning but quiet resorts that offer relaxation and easy access to the Gulf shoreline while the southern areas offer funky boutique shops and fun family adventures.

Here are a few of the top places to stay on Anna Maria Island that will make you want to book a trip right now.

Balcony view from luxury Anna Maria Island vacation rental

The Beach Front

Want to stay somewhere with a magnificent view of the Gulf of Mexico? The Beach Front is situated right on the beach front, as its name suggests. You can access a private walkway leading from the balcony to the beach.

If you get tired, you can stay inside and enjoy DSL high-speed internet, a television show, or take a swim in the heated swimming pool.

If you have several people in your group, you’ll find this place to be spacious. The Beach Front sleeps two to six people across its three bedrooms, two bathrooms. It is one of the bigger Anna Maria Island places to stay on the water.

Outside view of big vacation rental in Anna Maria, FL

Southern Exposure

Southern Exposure is a new rental located several blocks from the Bay and Gulf beaches. It has five bedrooms and 4.5 bathrooms. You’ll have plenty of room to lounge out if you’re bringing your family or a large group of friends along.

While it isn’t on the beach front, this luxury home is tucked away in a quiet neighborhood that offers a convenient walk to several restaurants. Sign of the Mermaid, The Sandbar, and Two Scoops ice cream parlor are all just a few minutes away!

Aerial shot of amazing luxury vacation rental in Bradenton Beach, FL

Anna Maria Grand Beach House

Prepare to have your breath taken away at this all-new, professionally decorated rental home. At Anna Maria Grand Beach House, you can simply walk out on the rooftop deck and take in a full view of the Gulf. There is a private heated pool that includes a swim-up bar and spa. Oh, and there’s even a waterfall!

Bringing your dog along? For a reasonable fee, your beloved pup is welcome to stay on the property.

outside view of vacation rental in Holmes Beach, FL

Caribbean Dream

Caribbean Dream lives up to its name. This five-bedroom rental is a 2.5-minute walk from the beach and offers a gorgeous view of both the Bay and Gulf. It is also close to plenty of eateries and stores, but it still manages to offer serene relaxation.

The real highlight of the Caribbean Dream is the private heated pool, which is adorned with tropical features.

If you don’t feel like going out to eat, there is a gourmet kitchen on the uppermost living level that is freshly stocked with delicious food.

Living room view of gorgeous Anna Maria vacation home

Paradise Point

Paradise Point might be just across the street from the vast Gulf, but it feels exceedingly intimate. You can enjoy time in the heated pool, which is fenced in for privacy. The outdoor area is truly the high point, with its huge balconies and impressive view of Bean Point.

Comfort is key at Paradise Point. You don’t even have to worry about washing your own laundry or packing your suitcase. All of that is taken care of for you by Paradise Point’s friendly staff.

View of back yard and pool area at a vacation rental in Bradenton Beach

Mandalay Bay

Looking to stay in a rental that really stands out? Mandalay Bay has a lovely rooftop deck that offers a panoramic view of the Gulf and Bay waters. You can even see the sailboats moored in front of Cortez Bridge. Enjoy fishing off the dock, complete with a fish cleaning station.

Mandalay Bay’s interior is just as delightful. Rejuvenate in the master bathroom’s steam shower or grab some grub from one of the two Sub Zero refrigerators.

Regardless of where you stay, you can take the free trolley anywhere you wish to go on the island. Having access to all of the marvelous views, restaurants, shops, and resort amenities makes staying on Anna Maria Island so comforting.