Search by Location
Bedrooms
Min Price
Max Price
Updating Results
90 Listings Match Your Search

Anna Maria Island Vacation Rentals

Anna Maria Island Vacation Rentals

About Anna Maria Island

Travelling to Anna Maria Island, Florida

Located along Florida’s southern coast, at the southern tip of Tampa Bay and the Gulf of Mexico, Anna Maria Island and its vacation rentals lie scattered amongst sea oats and Australian pines, in “Old Florida” neighborhoods close to the water’s edge. 

The towns of Anna Maria, Brandenton Beach, and Holmes Beach line the eleven-kilometre long barrier island, famed for its sugar-white sand beaches and emerald waters. Several beaches provide areas for sunbathing, swimming, and beachcombing. Boating, sea kayaking, and windsurfing are possible in bays and on the Gulf. Fishing is another popular island-wide activity, from one’s boat or any one of the three piers. Several parks and trails provide opportunities to catch glimpses of manatees, sea turtles, and dolphins, as well as egrets, herons, and pelicans. 

Anna Maria Island is home to a variety of boutiques, galleries, restaurants, cafés, and ice cream shops, including Mama Lo’s and Dips Ice Cream & Candy Store. While most of the island can be explored on foot or by bike, there is also a free trolley service that takes you wherever you want to go. Anna Maria Island offers natural and outdoors attractions, as well as a variety of amenities and rental accommodation options, and is less than a thirty minutes’ drive northwest of Sarasota

What to Do Here

What to do in Anna Maria Island, Florida

On The Ocean
Beach
Hot Weather
Golf

Articles

Travel Articles About Anna Maria Island, Florida

Anna Maria Island Vacation Rentals & Vacation Homes

Villa Marisol - 797ns

Vacation Homes in Anna Maria Island, Florida

4
Beds

3.5
Baths

$3,500
Week

Villa Marisol, on the enviable north beach of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Lakeview Cottage – 216 Lakeview

Condo Rentals in Anna Maria Island, Florida

2
Beds

1.5
Baths

$595
Week

A wonderful mid-century modern cottage lovingly built by a master craftsman who turned down work from Frank Lloyd Wright himself! Most of the beautiful trees on… More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Grand Oak - 6358goak

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$475
Week

Grand Oak Circle is in a great location to take advantage of eveything that Sarasota, Bradenton and Anna Maria Island has to offer. Exploring other areas of FL … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Lacasa Costiera

Cottage Rentals in Anna Maria Island, Florida

3
Beds

1
Baths

$3,192
Week

You'll be hard-pressed to find something more luxurious than this beautiful three bedroom, two-and-a-half bath unit at the prestigious La Casa Costiera. These … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

The Shore 113

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$3,000
Month

The Shore is a Gulf-front complex located near the north end of the island, with exquisite views from everywhere on the property. If you treasure your time on … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Beach Villa – 207 71st St - Condo Rental

Beach Villa – 207 71st St

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$443
Week

The perfect spot for the budget-conscious, beach-loving vacationer! This comfortable and clean 2 bedroom/2 bath elevated duplex is only 200 yards from the … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

111 Willow - Condo Rental

111 Willow

Condo Rentals in Anna Maria Island, Florida

3
Beds

2
Baths

$1,500
Week

Tour: http://www.pfretour.com/2688 Spend your vacation just steps from our beautiful beaches and crystal-clear waters! Casa Blanca is in the heart of the … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Casa Nana - 109will - Cottage Rental

Casa Nana - 109will

Cottage Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$900
Week

Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 4 houses from the beach! One Florida family has spent over four decades building … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Beach Castle Unit-6 - Condo Rental

Beach Castle Unit-6

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,190
Week

A view of the Gulf, but more economical than one of the other Gulf Front apartments at the Beach Castle, the owners have spared no expense in updating this … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Villa Nora South - 600ns - Condo Rental

Villa Nora South - 600ns

Condo Rentals in Anna Maria Island, Florida

2
Beds

1
Baths

$903
Week

Only a block to the pristine white sands of our Gulf of Mexico beaches, this lovely two bedroom/two bath duplex is nestled at the end of a long shell driveway, … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Palm Cove - 410 79th - Condo Rental

Palm Cove - 410 79th

Condo Rentals in Anna Maria Island, Florida

3
Beds

1
Baths

$1,400
Week

Enjoy your Anna Maria Island vacation in this marvelous three bedroom/two bath pool home just 300 yards to the beach! You'll feel instantly at home in this … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Beach Castle Unit-26 - Bc26 - Condo Rental

Beach Castle Unit-26 - Bc26

Condo Rentals in Anna Maria Island, Florida

1
Beds

1
Baths

$798
Week

Enjoy one of the best views of Sarasota Bay in the entire complex from this one bedroom, one bath second floor unit. Completely redecorated with new tile … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Beach Castle Unit-9 - Condo Rental

Beach Castle Unit-9

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,050
Week

A view of the Gulf, but more economical than the other Gulffront condominium at the Beach Castle Resort, the owners have spared no expense in renovating this … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Unit 16 Bermuda Bay Townhome - Condo Rental

Unit 16 Bermuda Bay Townhome

Condo Rentals in Anna Maria Island, Florida

3
Beds

2.5
Baths

$1,025
Week

Miles of White Sandy Beaches. Gorgeous unit, three private decks to relax on. Two car garage for secure and covered parking. Fully equipped Kitchen with … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Ami Beach Resort Rm 11 - Condo Rental

Ami Beach Resort Rm 11

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,450
Week

Two bedroom, pool side and garden view, nicely furnished. In the heart of Anna Maria Island, this resort has it all, King size bed, and Queen size bed in 2nd … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Bermuda Bay Unit 22 - Condo Rental

Bermuda Bay Unit 22

Condo Rentals in Anna Maria Island, Florida

3
Beds

2.5
Baths

$900
Week

Miles of White Sandy Beaches Gorgeous unit, three private decks to relax on. Two car garage for secure and covered parking. Fully equipped Kitchen with … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Ami Beach Resort Room 9 - Condo Rental

Ami Beach Resort Room 9

Condo Rentals in Anna Maria Island, Florida

1
Beds

1
Baths

$1,000
Week

One bedroom, Gulf View, nicely furnished on the second level. In the heart of Anna Maria Island, this resort has it all, King size bed, fully equipped mini … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Beach Castle Unit-5 - Condo Rental

Beach Castle Unit-5

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,190
Week

This updated first floor 2 bedroom, 2 bath condominium has a partial view of the Gulf of Mexico from the screened in lanai, and is just steps away from the … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Gulfview Townhome Unit 02 - Condo Rental

Gulfview Townhome Unit 02

Condo Rentals in Anna Maria Island, Florida

2
Beds

2.5
Baths

$750
Week

Miles of White Sandy Beaches. Very spacious two bedroom with a side den like area in the living room for extra guest(charge for extra guest). Large flat … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Paradise Charm – 213 Spring Ave - Condo Rental

Paradise Charm – 213 Spring Ave

Condo Rentals in Anna Maria Island, Florida

3
Beds

2
Baths

$1,400
Week

Tour: http://www.pfretour.com/3016 Overview Kick back and relax in this inviting 3 bedroom/2 bath pool home just two short blocks from the beach, and right in … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

1 - 20 of 90 Rentals

Sort

Trending Rentals in Anna Maria Island

Marketplace

Your One Stop Shop for Cottage Essentials

View More Items →