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.

Holiday Villas Anna Maria Island, FL

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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
All 819 Rentals in Anna Maria Island
loading...
Sort by
From
$167
Per Night
Anna Maria
2 Bedrooms, 1 Bathroom, Sleeps 6
19 photos Details
Reviews (3) Make Enquiry
From
$192
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (1) Make Enquiry
From
$289
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (1) Make Enquiry
Also consider
Anna Maria Island
2 Bedrooms, sleeps 6
$138 / night
Private, pet-friendly home 2 blocks from beach
3 Bedrooms, sleeps 6
$106 - $152 / night
Calm Horizon unit D gorgeous pool,steps to beach
2 Bedrooms, sleeps 6
$160 - $250 / night
Sun Porch - Florida Island Beach House
2 Bedrooms, sleeps 4
$149 / night
From
$160
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (2) Make Enquiry
From
$383
Per Night
Holmes Beach
3 Bedrooms, 4 Bathrooms, Sleeps 6
43 photos Details
Reviews (6) Make Enquiry
From
$126
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 7
14 photos Details
Reviews (7) Make Enquiry
From
$1,230
Per Week
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 7
22 photos Details
Reviews (1) Make Enquiry
From
$241
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
34 photos Details
Reviews (1) Make Enquiry
Get the List
From
$1,267
Per Week
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (8) Make Enquiry
From
$153
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
16 photos Details
Reviews (18) Make Enquiry
From
$292
Per Night
Holmes Beach
4 Bedrooms, 3 Bathrooms, Sleeps 8
36 photos Details
Reviews (1) Make Enquiry
From
$182
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
14 photos Details
Reviews (1) Make Enquiry
From
$857
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (3) Make Enquiry
From
$117
Per Night
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details
Reviews (1) Make Enquiry
From
$2,982
Per Night
Bradenton Beach
3 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details
Reviews (14) Make Enquiry
From
$378
Per Night
Holmes Beach
5 Bedrooms, 4 Bathrooms, Sleeps 12
27 photos Details
Reviews (3) Make Enquiry
From
$329
Per Night
Holmes Beach
5 Bedrooms, 8 Bathrooms, Sleeps 10
40 photos Details
Reviews (1) Make Enquiry
From
$105
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
22 photos Details
Reviews (4) Make Enquiry
From
$237
Per Night
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 6
27 photos Details
Reviews (4) Make Enquiry
From
$1,913
Per Week
Bradenton Beach
5 Bedrooms, 3 Bathrooms, Sleeps 14
22 photos Details
Reviews (1) Make Enquiry
From
$895
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
19 photos Details
Reviews (1) Make Enquiry
From
$99
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 7
14 photos Details
Reviews (2) Make Enquiry
From
$647
Per Night
Anna Maria
9 Bedrooms, 6 Bathrooms, Sleeps 26
22 photos Details
Reviews (4) Make Enquiry
From
$895
Per Week
Holmes Beach
2 Bedrooms, 3 Bathrooms, Sleeps 4
22 photos Details
Reviews (6) Make Enquiry
From
$138
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (7) Make Enquiry
From
$634
Per Week
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (1) Make Enquiry
From
$310
Per Night
Anna Maria
3 Bedrooms, 3 Bathrooms, Sleeps 8
29 photos Details
Reviews (2) Make Enquiry
From
$857
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
22 photos Details
Reviews (7) Make Enquiry
From
$164
Per Night
Bradenton Beach
1 Bedroom, 1 Bathroom, Sleeps 4
18 photos Details
Reviews (1) Make Enquiry
From
$2,124
Per Week
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
22 photos Details
Reviews (23) Make Enquiry
From
$134
Per Night
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (8) Make Enquiry
From
$1,752
Per Week
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
22 photos Details
Reviews (23) Make Enquiry
From
$133
Per Night
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 6
5 photos Details
Reviews (5) Make Enquiry
From
$1,006
Per Week
Bradenton Beach
1 Bedroom, 2 Bathrooms, Sleeps 5
20 photos Details
Reviews (12) Make Enquiry
From
$969
Per Week
Bradenton Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
20 photos Details
Reviews (11) Make Enquiry
From
$150
Per Night
Anna Maria
2 Bedrooms, 1 Bathroom, Sleeps 4
14 photos Details
Reviews (2) Make Enquiry
From
$932
Per Week
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (4) Make Enquiry
From
$256
Per Night
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Reviews (2) Make Enquiry
From
$1,901
Per Week
Holmes Beach
3 Bedrooms, 4 Bathrooms, Sleeps 12
22 photos Details
Reviews (17) Make Enquiry
From
$2,130
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (24) Make Enquiry
Go to map view
Popular cities
Book Online(130)
Use filters to find the best results!

Suitability

  • Wheelchair access (41)
  • Elder access (215)
  • Suitable for children (262)
  • Pet friendly (165)
  • Smoking allowed (2)

Amenities

  • Internet (735)
  • All pools (514)
  • Parking (474)
  • Grill (415)
  • Other outdoor space (374)
  • 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.