Top 15 Anna Maria Island Beach Cottage Rentals

Anna Maria Island beach cottage rentals are the perfect way to experience this old Florida vacation destination. There aren’t many places like the island anymore. You won’t find any high rises, big night clubs or chain store outlets in this quaint coastal getaway. Such a charming gulf island, a beautiful vacation cottage is the perfect match.

Anna Maria Island Beach Cottage Rentals

Here is a list of 15 of the best Anna Maria Island beach cottage rentals for you to try out! All offer a little something different. Additionally, these range from old to new, and from bronze to platinum rated. Arranged by city location in Anna Maria, Holmes Beach or Bradenton Beach, these great cottages also span the entire island.

Anna Maria beach cottage rentals

Sea Song is a direct gulf front cottage. Updated in December 2015, the beach is your backyard! Sleep up to six in this two bedroom home with beautiful beach views and amenities. Gold rated.

Anna Maria Island beach cottage rentals
Sea Song 103 Sea Grape Lane.

The Seashell Cottage is just down the street from gulf beaches, and is within walking distance to Pine Avenue shopping and dining. This quaint cottage also sleeps six guests with two bedrooms. Silver rated.

Anna Maria Beach cottage rental
The Seashell Cottage 118 Palmetto Avenue.

Fish House is really something special! Sleep eight guests with three bedrooms. Enjoy high end luxury mixed with an old fish camp feel. Heated pool and spa too! Gold rated.

Anna Maria cottage vacation rental
Fish House 231 Oak Avenue.

Dolphin Watch is similarly a great beach front cottage. Furthermore, this home sleeps six with two bedrooms, and beach views. Gold rated.

Anna Maria beach rental.
Dolphin Watch 12108 Gulf Drive.

Blue Bayou is a stylish updated cottage. Sleeps six with three bedrooms on direct canal front. Undoubtedly a beautiful location with heated pool and spa! Platinum rated.

Anna Maria Rental Cottage
Blue Bayou 229 Chilson Avenue

Hacienda Del Mar is in fact one of the larger cottage beach rentals offered on the list. Sleep eight guests with four bedrooms. Also on direct gulf front, and recently updated. Gold rated.

beach rental Anna Maria
Hacienda Del Mar 765 North Shore Drive.

Holmes Beach cottage rentals

Minnie Cottage is surely the ideal Holmes Beach cottage. Also sleeps eight guests, but with three bedrooms. This raised cottage has a heated pool and is a newer home. Platinum rated.

Holmes beach cottage rental
Minnie Cottage 125 47th Street.

Blue Lagoon 6 Osprey is a popular cottage. In contrast to others, this cottage is located in a small complex. Sleeps four with two bedrooms, and just a short walk to the beach. Gold rated.

Beach Cottage rental Holmes Beach
Blue Lagoon 6 – Osprey – 215 67th Street.

Beach Comber is great for a no frills cottage. That is to say, this rental offers all the basics, but with the addition of direct gulf views. Also sleeps six with two bedrooms. Bronze rated.

Anna Maria Island vacation rental Holmes Beach
Beach Comber 3020 Avenue F.

Captains House is a funky Florida cottage. To clarify, this home has a retro feel that is super fun. Sleep eight with three bedrooms, and also a loft style with two living levels. Bronze rated.

Beach house rentals anna maria island
Captains House 208 Haverkos.

Misty Beach has an updated beach style, and sleeps six guests with two bedrooms. This cottage offers a heated pool too! Gold rated.

Vacation cottage Holmes Beach
Misty Beach 5802 Imperiore Avenue.

Pelican Landing AMI is a spacious cottage with three bedrooms for up to eight guests. This great home also has a fun backyard Tiki hut and heated pool. Gold rated.

Rental cottage Holmes Beach
Pelican Landing AMI 306 55th Street.

Jackie’s Cottage is an updated canal front cottage with a heated pool. Manatees frequent this canal too! Sleep eight guests with four bedrooms. Gold rated.

Anna Maria Island cottage rental Holmes Beach
Jackie’s Cottage 209 North Harbor Drive.

Bradenton Beach cottage rental

A Pirate’s Cove is a 1950’s cottage updated with modern coastal charm and amenities. Heated pool, and also just a block from gulf beaches. Sleep six with two bedrooms. Gold rated.

Bradenton Beach cottage rental Anna Maria Isalnd
A Pirate’s Cove 2109 Avenue C.

Katie’s Beach Bungalow is a short walk to gulf beaches, and has a heated pool and spa! Sleep four guests with two bedrooms. Bronze rated.

Cottage rental Anna Maria Island
Katie’s Beach Bungalow 108 8th Street South.

Enjoy the perfect Old Florida paradise getaway by the beach with one of these charming Anna Maria Island beach cottage rentals. Visit IslandReal.com today to reserve your stay.

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