An aerial view of a coastal town with a long pier extending into turquoise waters.

Anna Maria Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Anna Maria Island vacation rentals

1. Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (482 reviews)
"Great location and walking distance to the beach"
United States
Francesca
The price is CA $191
CA $241 total
includes taxes & fees
Nov 29 - Nov 30
Pelican Post at Anna Maria Island Inn

2. Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (174 reviews)
"It was just a beautiful stay and love to come back next year!!"
United States
Allison
The price is CA $102
CA $789 total
includes taxes & fees
Nov 2 - Nov 3
Palm Tree Villas

3. Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (153 reviews)
"Beautiful place"
United States
Danay
The price is CA $280
CA $354 total
includes taxes & fees
Nov 18 - Nov 19
Seabreeze at Anna Maria Island Inn

4. Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (494 reviews)
"perfect"
United States
Danielle
The price is CA $222
CA $281 total
includes taxes & fees
Nov 29 - Nov 30
Haley's at The Anna Maria Island Inn

5. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (843 reviews)
"I loved this hotel"
United States
Raisare
The price is CA $376
CA $464 total
includes taxes & fees
Nov 29 - Nov 30
Bridgewalk Resort

6. Anna Maria Sunsets - studio

Anna Maria Sunsets - studio
Bradenton Beach
9.0 out of 10, Wonderful, (276 reviews)
"Loved our stay!"
United States
Vincent
The price is CA $189
CA $401 total
includes taxes & fees
Oct 31 - Nov 1
Anna Maria Sunsets - studio

7. Anna Maria Sunsets - studio

Anna Maria Sunsets - studio
Bradenton Beach
9.2 out of 10, Wonderful, (290 reviews)
"We had a wonderful stay! The place was clean, comfortable, and exactly as described. The location was great, and everything we needed was available. The host was friendly, responsive, and made the whole experience easy and enjoyable. We would definitely stay here again and highly recommend it! ⭐️⭐️⭐️⭐️⭐️"
United States
Elizabeth
The price is CA $176
CA $385 total
includes taxes & fees
Nov 1 - Nov 2
Anna Maria Sunsets - studio

8. Anna Maria Beach Condo 1/1

Anna Maria Beach Condo 1/1
Bradenton Beach
9.8 out of 10, Exceptional, (238 reviews)
"Great place to stay!"
United States
Donna B.
The price is CA $220
CA $531 total
includes taxes & fees
Oct 30 - Oct 31
Anna Maria Beach Condo 1/1

9. Fabulous 1-bedroom condo with AC in Bradenton Beach

Fabulous 1-bedroom condo with AC in Bradenton Beach
Bradenton Beach
9.0 out of 10, Wonderful, (39 reviews)
"Everything about my stay was great! Will definitely be back!"
United States
Darian
The price is CA $176
CA $394 total
includes taxes & fees
Nov 1 - Nov 2
Fabulous 1-bedroom condo with AC in Bradenton Beach

10. Cozy 1-bedroom condo with AC in Bradenton Beach

Cozy 1-bedroom condo with AC in Bradenton Beach
Bradenton Beach
9.4 out of 10, Exceptional, (46 reviews)
"Enjoyed the proximity to beach access, free trolley, and restaurants. "
United States
DanRoxy R.
The price is CA $183
CA $429 total
includes taxes & fees
Nov 1 - Nov 2
Cozy 1-bedroom condo with AC in Bradenton Beach

11. The Pelican's Perch, a Beachfront studio condo w/ balcony

The Pelican's Perch, a Beachfront studio condo w/ balcony
Bradenton Beach
10.0 out of 10, Exceptional, (11 reviews)
"Host was awesome and the location was perfect."
United States
Diane S.
The price is CA $320
CA $631 total
includes taxes & fees
Nov 1 - Nov 2
The Pelican's Perch, a Beachfront studio condo w/ balcony

12. Island Life #7 Beach Club AMI RVA

Island Life #7 Beach Club AMI RVA
Bradenton Beach
9.0 out of 10, Wonderful, (93 reviews)
"Love the proximity to the beach. Pool and hot tub are great"
United States
Kimberly H.
The price is CA $184
CA $430 total
includes taxes & fees
Oct 30 - Oct 31
Island Life #7 Beach Club AMI RVA

13. Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Anna Maria
10.0 out of 10, Exceptional, (44 reviews)
"Loved the easy access to the beach and the fact that the property had beach supplies available for you to use. We had great service when needed and will definitely visit again !"
United States
Meagan
The price is CA $279
CA $738 total
includes taxes & fees
Nov 9 - Nov 10
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

14. Sugary Sands 1 Bed Condo and One Block to Beach!

Sugary Sands 1 Bed Condo and One Block to Beach!
Bradenton Beach
9.4 out of 10, Exceptional, (26 reviews)
"Very pleasant stay. Short walk to beach and we had access to wagon and beach chairs. Location is great, very close to Bridge St. and many restaurants.Property manager had emailed all necessary information for condo. We enjoyed our stay at Sugary Sands!"
United States
Christine S.
The price is CA $236
CA $805 total
includes taxes & fees
Nov 6 - Nov 7
Sugary Sands 1 Bed Condo and One Block to Beach!

15. Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
Anna Maria
9.6 out of 10, Exceptional, (31 reviews)
"Very short walk to the beach. We enjoyed our stay. "
United States
Stacey D.
The price is CA $291
CA $774 total
includes taxes & fees
Nov 7 - Nov 8
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

16. Updated bayside condo with heated pool - across the street from the beach

Updated bayside condo with heated pool - across the street from the beach
Anna Maria
9.2 out of 10, Wonderful, (108 reviews)
"It is a very nice little unit. Recently renovated and comfortable. We had some problems with the front door lock that they are aware of, so it took a bit of time to initially enter the property. If the upper floor is occupied, it is a bit noisy from the activity overhead. The location is very good for walking to restaurants and shops. The Waterfront Restaurant is excellent!"
United States
Rick C.
The price is CA $190
CA $670 total
includes taxes & fees
Nov 20 - Nov 21
Updated bayside condo with heated pool - across the street from the beach

17. Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
Anna Maria
9.8 out of 10, Exceptional, (34 reviews)
"We loved our stay at 107A! It was perfect for the two of us, We loved the short walk to the beach and how walkable it was to local restaurants and stores. Thank you for a great stay!"
United States
Kathryn M.
The price is CA $284
CA $756 total
includes taxes & fees
Nov 15 - Nov 16
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

18. Amazing View, Updated Beachfront Condo

Amazing View, Updated Beachfront Condo
Bradenton Beach
9.2 out of 10, Wonderful, (63 reviews)
"Exceptional beach condo, great view and clean."
United States
Paul W.
The price is CA $287
CA $875 total
includes taxes & fees
Nov 15 - Nov 16
Amazing View, Updated Beachfront Condo

19. Anna Maria Beach Condo 1/1

Anna Maria Beach Condo 1/1
Bradenton Beach
9.8 out of 10, Exceptional, (269 reviews)
"Great location right by the beach"
United States
enrique
The price is CA $227
CA $538 total
includes taxes & fees
Nov 1 - Nov 2
Anna Maria Beach Condo 1/1

20. Sun, Sand & Style #6 Beach Club AMI RVA

Sun, Sand & Style #6 Beach Club AMI RVA
Bradenton Beach
9.4 out of 10, Exceptional, (96 reviews)
"Nice condo and great location! Perfect for 2 people. The front desk people are super nice and very helpful."
United States
Joretta B.
The price is CA $207
CA $460 total
includes taxes & fees
Oct 30 - Oct 31
Sun, Sand & Style #6 Beach Club AMI RVA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Anna Maria Island Hotel Reviews

Find out more about Anna Maria Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Anna Maria Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia