We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation rentals in Anna Maria Island, FL

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 694 Rentals in Anna Maria Island
loading...
Sort by
From
$255
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
33 photos Details
Reviews (8) Make Enquiry
From
$164
Per Night
Bradenton Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
11 photos Details
Reviews (1) Make Enquiry
From
$211
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
32 photos Details
Reviews (4) Make Enquiry
Also consider
C-view Florida, Canal/Dock/Heated Pool/Near Gulf
5 Bedrooms, sleeps 10
$301 - $383 / night
Happy Ours-Changes in Attitude, Gulf of Mexico!
1 Bedroom, sleeps 4
$164 / night
Sunset Terrace Beach Front Condo
2 Bedrooms, sleeps 6
$157 - $236 / night
The Shady Mango ~ Anna Maria Island's Most Charming Coastal Cottage!
2 Bedrooms, sleeps 4
$274 - $383 / night
From
$104
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
32 photos Details
Reviews (2) Make Enquiry
From
$219
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
21 photos Details
Reviews (7) Make Enquiry
From
$126
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 5
Bookings
10 photos Details
Reviews (2) Make Enquiry
From
$230
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
25 photos Details
Reviews (5) Make Enquiry
From
$181
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
9 photos Details
Reviews (1) Make Enquiry
Get the List
From
$203
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
24 photos Details
Reviews (3) Make Enquiry
From
$180
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
64 photos Details
Reviews (1) Make Enquiry
From
$1,205
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
18 photos Details
Reviews (2) Make Enquiry
From
$219
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
14 photos Details
Reviews (1) Make Enquiry
From
$110
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
33 photos Details
Reviews (10) Make Enquiry
From
$274
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
-128 photos Details
Reviews (13) Make Enquiry
From
$94
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Reviews (4) Make Enquiry
From
$120
Per Night
Bradenton Beach
1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
21 photos Details
Reviews (14) Make Enquiry
From
$849
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
18 photos Details
Reviews (6) Make Enquiry
From
$110
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
23 photos Details
Reviews (20) Make Enquiry
From
$186
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
41 photos Details
Reviews (5) Make Enquiry
From
$192
Per Night
Bradenton Beach
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
21 photos Details
Reviews (2) Make Enquiry
From
$126
Per Night
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
57 photos Details
Reviews (19) Make Enquiry
From
$137
Per Night
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
9 photos Details
Reviews (3) Make Enquiry
From
$110
Per Night
Anna Maria
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
8 photos Details
Reviews (9) Make Enquiry
From
$274
Per Night
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
78 photos Details
Reviews (1) Make Enquiry
From
$126
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
24 photos Details
Reviews (1) Make Enquiry
From
$274
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
127 photos Details
Reviews (8) Make Enquiry
From
$99
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
10 photos Details
Reviews (1) Make Enquiry
From
$219
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
35 photos Details
Reviews (17) Make Enquiry
From
$159
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (2) Make Enquiry
From
$120
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
12 photos Details
Reviews (3) Make Enquiry
From
$107
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
45 photos Details
Reviews (13) Make Enquiry
From
$186
Per Night
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
52 photos Details
Reviews (8) Make Enquiry
From
$406
Per Night
Bradenton Beach
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
24 photos Details
Reviews (1) Make Enquiry
From
$192
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 3
22 photos Details
Reviews (1) Make Enquiry
From
$164
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
11 photos Details
Reviews (1) Make Enquiry
From
$294
Per Night
Anna Maria
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
37 photos Details
Reviews (3) Make Enquiry
From
$159
Per Night
Anna Maria
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
12 photos Details
Reviews (6) Make Enquiry
From
$148
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
19 photos Details
Reviews (1) Make Enquiry
From
$493
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
20 photos Details
Reviews (1) Make Enquiry
From
$211
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
27 photos Details
Reviews (4) Make Enquiry
Go to map view
Popular cities
Book Online(160)
Use filters to find the best results!

Suitability

  • Wheelchair access (44)
  • Elder access (240)
  • Suitable for children (309)
  • Pet friendly (142)
  • Smoking allowed (1)

Amenities

  • Internet (598)
  • All pools (455)
  • Grill (453)
  • Other outdoor space (414)
  • Parking (381)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Waterfront vacation rentals on Anna Maria Island

Whether an experienced or a first-time vacation home renter, you’ll enjoy the many choices for beachside getaways on Anna Maria Island. Luxury gulf side villas, quaint beach cottages and canal front condos offer breathing-room space and countless amenities that traditional hotel stays can’t match. Beyond the advantage of preparing some meals at home, your beach rental allows you to slide right into islander life and feel very much at home.

“Old Florida” charm and easy island living

Three small communities share Anna Maria Island – Bradenton Beach, Holmes Beach and Anna Maria. Each gathers along 7 miles of silky white beach overlooking the Gulf of Mexico. The island offers the village feel of Old Florida, with simple beach cottages and sandy lanes dipping under lazy Florida oaks and beachfront villas overlooking turquoise bays. There’s plenty to do on the family-friendly island, but nothing quite as important as simple relaxation. Rent a bike to roam the island or a kayak to explore the waterways. Fish, sail, comb the beaches for shells, and pack a little picnic for a sunset meal.

One-of-a-kind dining and shopping

Shop names reveal that island boutiques are anything but ordinary. The Painted Gate, Egret’s Landing, Paper Panache and other local establishments offer everything from resort wear to arts and crafts. The free island trolley runs North and South, as a convenient way to explore. Ginny's and Jane E's at the old IGA is a popular spot, where vintage furniture mixes with home-baked quiches and brioches in an internet café setting. One restaurant you can’t miss is Rod & Reel located at the end of a wooden pier jutting out into the bay. Kick back, fish, eat and let that tropical seascape deliver complete relaxation.

Take a side trip south to “Shangri-la”

Don your best resort wear and head south along Highway 789 that links Anna Maria Island to Longboat and St. Armand Keys. The gulf front drive leads you to famous St. Armand’s Circle, where elite shopping and pampered dining venues merge in an elegant European atmosphere. After a gourmet lunch, venture over to Sarasota for a visit to the cherished Ringling enclave, home to the Museum of Art and Ca d’Zan Mansion. Set in a lush 20-acre garden overlooking the water, the Venetian mansion is considered “the last of the Gilded Age mansions” built in America.

Vacation rental homes, a superb value for families and friends

Spacious living areas, plenty of baths and bedrooms and every imaginable amenity explain why vacation homes are today’s most popular travel choices. From the comfort of your own island getaway, you’ll enjoy every pleasure Anna Maria Island offers.