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

Paradise Gulf Cottage - 6485gmd

Condo Rentals in Anna Maria Island, Florida

3
Beds

2
Baths

$1,500
Week

Enjoy a terrific holiday at Fairway Bay, one of south Longboat Key's most coveted addresses! It's easy to see why people love to stay at this beautiful, … 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

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

Bermuda Bay Unit 09 - Condo Rental

Bermuda Bay Unit 09

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 10 - Condo Rental

Ami Beach Resort Room 10

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,200
Week

Two Bedroom, Pool side, partial gulf view, nicely furnished on the second level. In the heart of Anna Maria Island, this resort has it all, King size beds, … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Perico Island Flamingo Cay - Condo Rental

Perico Island Flamingo Cay

Condo Rentals in Anna Maria Island, Florida

3
Beds

2
Baths

$1,200
Week

Located in Flamingo Cay in Perico Bay area just off of Anna Maria Island. This is a gorgeous 3 bedroom home with a very relaxing interior atmosphere. Carpet in … 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

Triplex Unit A - Condo Rental

Triplex Unit A

Condo Rentals in Anna Maria Island, Florida

2
Beds

1
Baths

$1,050
Week

Nice two bedroom with Pool and BBQ area. This unit is in an excellent location. It has all the amenities needed either for a short stay or longer. This Unit is … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Unit 04 Bermuda Bay Townhome - Condo Rental

Unit 04 Bermuda Bay Townhome

Condo Rentals in Anna Maria Island, Florida

3
Beds

2.5
Baths

$1,050
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

River Club Unit Rc403 - Condo Rental

River Club Unit Rc403

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$500
Week

Downtown Bradenton 15 minutes from beach. This unit has a spectacular view of the Manatee River. Two bedroom nicely furnished, fully equipped kitchen, Cable TV… 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

Gulf Beach Place Unit 02 - Condo Rental

Gulf Beach Place Unit 02

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$925
Week

On first level up, view of beach. Very spacious two bedroom Condo with a patio area off the living room. Flat screen TV, fully equipped kitchen with all the … 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 03 - Condo Rental

Bermuda Bay Unit 03

Condo Rentals in Anna Maria Island, Florida

3
Beds

2.5
Baths

$900
Week

Miles of White Sandy Beaches This is 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

Triplex Unit C - Condo Rental

Triplex Unit C

Condo Rentals in Anna Maria Island, Florida

1
Beds

1
Baths

$850
Week

Cute one bedroom on Unit on Anna Maria Island. This unit is in an excellent location. It has all the amenities needed either for a short stay or longer. This … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Triplex Unit B - Condo Rental

Triplex Unit B

Condo Rentals in Anna Maria Island, Florida

2
Beds

1
Baths

$900
Week

Nice Two Bedroom with Pool area and BBQ. This unit is in an excellent location. It has all the amenities needed either for a short stay or longer. This Unit is… More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Ami Beach Resort Rm 02 - Condo Rental

Ami Beach Resort Rm 02

Condo Rentals in Anna Maria Island, Florida

1
Beds

1
Baths

$900
Week

One Bedroom, garden view, nicely furnished. In the heart of Anna Maria Island, this resort has it alll. King size bed, fully equiped kitchen with Refrigerator, … More →

CottageCountry.com Secure PaymentsCottageCountry.com Refund Protection

Gulf Sands Unit 206 - Condo Rental

Gulf Sands Unit 206

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,200
Week

2 bedroom, 2 bath with beautiful view of Gulf from balcony, large heated pool. Very spacious two bedroom Condo with a patio area off the living room. Flat … 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 →