Anna Maria Island – So Close yet So Far

It offers a little bit of everything: traditional Florida vibes, access to the Gulf of Mexico, peace, quiet and convenience. Anna Maria Island is just off the coast, but traveling here will make you feel like you’ve landed on a different planet.


Island living always offers an unparalleled sense of relaxation, so just the act of depositing yourself here will do wonders for your state of mind. Once you have your bearings, though, check out the area attractions…


Eco-tourism is a hot ticket, meaning that you’ll have the chance to learn and enjoy nature to the max. Bird watching, kayak tours and combing the beach for shells are a few ideas, so keep your eyes open for jumping dolphins, floating manatees and diving pelicans as you meander around.


On a less wild note, there’s plenty of shopping and dining to be had, and the delicate comforts of your vacation house or condo will leave you feeling downright pampered. Cottages with beach views and bungalows with all the fixings are bound to make evenings, nights and in-between moments as comfortable as can be.


If you can’t find what you need at the nearby supermarkets or tire of the tennis courts, skate park, ocean activities and sunset views offered in the Anna Maria Island Area (it’s unlikely that you will, but just in case…) visit one of the nearby towns. Bradenton, Bradenton Beach, Holmes Beach and Sarasota are a few options that will widen the lens of your vacation, but keeping things simple is just fine, too.


This Florida isle is treasured as something of a secret, so feel lucky that you’ve discovered it.

Destination: Search

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Vacation Rentals on Anna Maria Island

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Luxury Corner Townhome with Spectacular Bay Views in Ruskin – Property 245150

  • Anna Maria Island rental - townhome, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, beach, resort, pool
  • $900 - $1,000/week
  • Calendar Last Updated On: Nov 8, 2009
Luxury corner Townhome with gorgeous views of the bay. Close to golf course, restaurants,and a privat beach. The townhome is a new end unit, build in 2007 and part...

A Beach Place - North End - Heated Pool - Steps to Gulf and Bay – Property 220758

  • Anna Maria Island rental - house, 2 bedrooms, sleeps 6, beach, near the ocean, pool
  • $850 - $1,100/week
  • Calendar Last Updated On: Nov 8, 2009
Situated at the quiet north end of Anna Maria Island. Removed from the condos, hotels, and crowds. We are one short block from sunrises on the bay, and the historic...

Paradise Found in this beautiful and private canal/pool retreat with dock – Property 256237

  • Anna Maria Island rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, near the ocean, waterfront, pool
  • Calendar Last Updated On: Nov 8, 2009
Come and relax and enjoy our island paradise at our beautiful Anna Maria Island canal front home with private dock. This beautiful professionally designed and...

Dreamy villa with pool and boat upon request – Property 517287

  • Anna Maria Island rental - villa, 3 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, private pool
  • $950 - $1,150/week
  • Calendar Last Updated On: Nov 8, 2009
Is it a coincidence or fate that we and now you have found this dream house? Enter and enjoy the stunning view of the spacious pool area with a partially covered...

Beautiful Condo on the Beach – Property 54340

  • Anna Maria Island rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, communal pool
  • $1,000 - $1,450/week
  • Calendar Last Updated On: Nov 8, 2009
Relax watching the dolphins play and listening to the gentle surf from the spacious balcony of this beautiful condo which is situated directly on a sugar soft white...

Charming Studio w/Lanai - Island Decor – Property 223748

  • Anna Maria Island rental - studio, sleeps 2, 1 bathroom, beach, garden
  • $500 - $650/week
  • Calendar Last Updated On: Nov 7, 2009
Come stay at Mermaid's Reef Gulf Side Unit and relax in the shade below our tall palms just steps from Anna Maria's beautiful uncrowded beach.

Key West Style Cottage with Private Garden Pool / a block from beach – Property 125606

  • Anna Maria Island rental - cottage, 3 bedrooms, sleeps 6, 3 bathrooms, beach, near the ocean, pool
  • $1,600 - $2,500/week
  • Calendar Last Updated On: Nov 7, 2009
Charming Key West style cottage with secluded garden pool on the desirable north end of the island. Beach access at the end of the block to one of the best and most...

Breakers 4 at Sandcastle – Property 7031835

  • Anna Maria Island rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, adventure, beach
  • $1,575 - $2,625/week
  • Calendar Last Updated On: Nov 7, 2009
Breakers 4 at the Sandcastle, located at 200 Gulf Drive South in Bradenton Beach is a luxury Gulf front condominium that embodies the old Florida lifestyle.

Stunning gulf pool villa overlooking golf course with wi-fi – Property 85718

  • Anna Maria Island rental - villa, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, rural, village, private pool
  • $774 - $856/week
  • Calendar Last Updated On: Nov 7, 2009
Stunning pool home on Imperial Lakewoods, 550 acre award winning Golf Course overlooking course and lakes. The course has 14 lakes and a host of wildlife - an...

Luxury 5 bed & 3 bed Gulf Coast Villas, private pools - close to IMG Bollettieri - Runabout Way – Property 55435

  • Anna Maria Island rental - villa, 3 bedrooms, sleeps 8, 2 bathrooms, near the ocean, private pool
  • $807 - $970/week
  • Calendar Last Updated On: Nov 8, 2009
These family owned luxury villas are decorated and furnished to a very high standard. They offer spacious living areas complete with every luxury to ensure you and...

Tropical Resort Vacation Home – Property 229611

  • Anna Maria Island rental - house, 5 bedrooms, sleeps 16, 4 bathrooms, beach, resort, jacuzzi
  • $1,200 - $1,800/week
  • Calendar Last Updated On: Nov 6, 2009
This elegant 5 bed, 4 bath private home is in West Bradenton - less than 10 minutes from the Island Beaches, Gulf of Mexico. The property is surrounded by tropical...

Island Paradise steps from the Gulf and the Bay! Openings in January ! – Property 258102

  • Anna Maria Island rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, resort, pool
  • $750 - $1,200/week
  • Calendar Last Updated On: Nov 7, 2009
This 2 bedroom 2 bathroom ground floor condo is located at Beautiful Runaway Bay. The vacation resort located between the Gulf of Mexico and Sarasota Bay, has been...

Directly on the Beach! Beautiful Ground Floor Condo – Property 221436

  • Anna Maria Island rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, waterfront, pets considered
  • $805 - $1,085/week
  • Calendar Last Updated On: Nov 6, 2009
This is a beautifully updated clean condominium inside and out. The complex just completed a major exterior renovation. You will love our professionally decorated...

Gulf Front Luxury Condo – Property 110772

  • Anna Maria Island rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, beach, waterfront, air-conditioning
  • $1,100 - $1,500/week
  • Calendar Last Updated On: Nov 6, 2009
Enjoy this completely re-modeled condo directly on the Gulf of Mexico. View the heated pool and white sand beach from the large balcony, master bedroom and living...

Anna Maria Island Vacation Rentals, Anna Maria Island, Florida Beach Rentals – Property 115036

  • Anna Maria Island rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, pool
  • $1,000/week
  • Calendar Last Updated On: Nov 5, 2009
Our Anna Maria Island beach rentals condo is completely surrounded by four tropical bodies of water with the Gulf of Mexico to the West, Tampa Bay to the North,...

Anna Maria Island Vacation Rental... A Pool & Condo at the beach.. – Property 213272

  • Anna Maria Island rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, near the ocean, resort, sauna
  • $550 - $1,275/week
  • Calendar Last Updated On: Nov 8, 2009
This condo is located on the second floor in Runaway Bay. Runaway Bay is a lovely vacation resort on beautiful grounds between the Gulf of Mexico and Sarasota Bay...

Sunsets and Memories – Property 7031849

  • Anna Maria Island rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, adventure, balcony
  • $1,775 - $2,850/week
  • Calendar Last Updated On: Nov 5, 2009
Sunsets and Memories, located at 302 65th Street in Holmes Beach is a beautiful, new, four bedroom, three and one half bath home on a quiet residential street, only...

Luxurious Lakeside / Golf View Home with own Private Heated Pool – Property 17188

  • Anna Maria Island rental - villa, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, near the ocean, resort, private pool
  • $800/week
  • Calendar Last Updated On: Nov 5, 2009
This fully equipped 3 Bed / 2 Bath home is on a larger than usual plot and in the prestigious gated community of Heritage Harbour.

Large 5 bed / 4 bath House with Private, Heated Pool & Spa near Gulf Coast – Property 84991

  • Anna Maria Island rental - villa, 5 bedrooms, sleeps 10, 3 bathrooms, 1 half bath, resort, private pool
  • $1,100 - $1,800/week
  • Calendar Last Updated On: Nov 5, 2009
Backing on to unspoilt 'Preserve' land bordering the Manatee River, this 2 storey, 5 bedroom / 4 bath 'executive home' sleeps up to 10 people comfortably and is...

Updated Condo on Anna Maria Island at Runaway Bay – Property 155477

  • Anna Maria Island rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, tennis court
  • $575 - $1,000/week
  • Calendar Last Updated On: Nov 5, 2009
This updated condo is located on the second floor in Runaway Bay. Runaway Bay is a lovely vacation resort on beautiful grounds between the Gulf of Mexico and...
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