Search Cottages in Anna Maria Island

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Check prices for these dates

Compare 70 Cottages in Anna Maria Island with updated reviews, rates, and availability.

We will be accepting new reservations from January 2025 going forward only.

9.8 out of 10, Exceptional, (187)
"We enjoyed our stay. The rental is close to beaches and trolley takes you anywhere on the island. Rental is clean and owner checks in with you often. "
We will be accepting new reservations from January 2025 going forward only.

Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!

10.0 out of 10, Exceptional, (258)
"We had an amazing getaway! The best location and amenities! The cottage is stocked with everything you need and more.. and it's decor is so cute! Highly recommend staying here. Thank you to our wonderful hosts - very accommodating they're super nice!!! We plan on a return trip! "
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

10.0 out of 10, Exceptional, (1)
"This was perfect for our family. It was a quick walk to the beach. We loved it!"
The price is SARĀ 750
SARĀ 1,910 total
includes taxes & fees
11 Apr - 12 Apr
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (263)
"Cindy was the best host weā€™ve ever encountered. She is so accommodating and communicative. She made our trip so easy! The location is perfect, just a few minutes walk to the beach or the bay, a couple blocks over from all of the shopping and restaurants on Pine Street and just down the street from a trolley stop. She has all the amenities for making the beach trip easy & comfortableā€¦a wagon to hold the chairs, an umbrella, a cooler and all of your bags. I would highly recommend!"
Charming cottage in quiet area, close to beach & bay.

Shell Cottage - sleeps 2

9.8 out of 10, Exceptional, (34)
"We could not ask for any better of a vacation"
Shell Cottage - sleeps 2

Great Location, steps to beach, 2 bd home w/ private pool

9.8 out of 10, Exceptional, (27)
"We had an awesome time on our trip, the house was CLEAN and even better than the pictures. The couches were different than the pics, way better, beautiful beachy green and brand new looking. LOVED the private pool, just the right size for two adults and two kids. The washer/dryer was soo nice, brand new looking as well. Loved the location, couldnā€™t have asked for a better place to stay for a family of 4. "
Great Location, steps to beach, 2 bd home w/ private pool

Tropical Paradise On The Beach Permit VRC17-000168

9.2 out of 10, Wonderful, (127)
"Quaint beach cottage tucked away from the hustle an bustle of the island. The upper unit had a spectacular view of the beach and sunsets.Communication with the property managers was great!We have already booked again for next year!Thank you for a wonderful stay!"
Tropical Paradise On The Beach Permit VRC17-000168

Beautiful Condo on Pine Ave, 2 Blocks to Beach

9.0 out of 10, Wonderful, (21)
"Great location, clean, and spacious. Pool didnā€™t work fir a couple of days but they got it fixed the day before we left "
Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beach Basket Cottage: Cute Old Florida Style Beach Cottage just steps to the Beach!

10.0 out of 10, Exceptional, (43)
"The beach basket cottage was perfect for our family of 6! It was clean, well stocked, and in a great location! It was a little cozy for all 6 of us, but we made it work and the location and communication more than made up for it. Great stay!!"
Beach Basket Cottage: Cute Old Florida Style Beach Cottage just steps to the Beach!

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK

8.8 out of 10, Excellent, (71)
"This house on Anna Maria Island was a perfect vacation. The island is obviously still recovering from hurricane damage, but in a way that probably made this stay better. It was super quiet - even with construction going on - which was expected. This house has an awesome backyard with the privacy fence and pool. The pool was heated, and although cold first couple days because I'm sure they had just finished filling it for us, the last several days with it were really nice! The beach is literally...
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK

Great location, cute cottage, 2 min walk to beach, 2bd/2ba home w/private pool

9.8 out of 10, Exceptional, (27)
"Great little beach cottage one block from the beach! Perfect for my husband and I and was well-appointed with everything we needed. Loved the very private backyard. A good number of restaurants and shops are open again after the hurricane so we were able to experience them. The property management company was informative and responsive. Thank You!"
Great location, cute cottage, 2 min walk to beach, 2bd/2ba home w/private pool

Charming Ground Level Resort Style 3 unit Condo - unit C

9.6 out of 10, Exceptional, (12)
"The rental was exactly as stated. It is small but it has everything you need for a perfect vacation. You canā€™t beat the location and the pool was a big bonus. We would definitely stay here again in the future."
Charming Ground Level Resort Style 3 unit Condo - unit C

Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!

9.4 out of 10, Exceptional, (19)
"The house was clean, had all the items needed to feel at home. Comfortable beds. Decorated nicely. Tucked into the property to allow for privacy. We enjoyed the area a d the realaxing time. Holmes beach was the nicest beach in the area. Not too crowded."
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!

Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach

10.0 out of 10, Exceptional, (18)
"Clean, well equipped condo with the beach for the back yard. Great location, close to Publix and local shops, restaurants and beaches, Tammy was welcoming and responsive."
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach

Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6

8.0 out of 10, Very Good, (3)
"We rented the SeaShell Cottage for the weekend of our daughter's wedding for our son, daughter - in - law and their daughter. It was only 2 blocks from the Venue - The Sandbar which was very convenient for them with an infant. The cottage was super clean and just down right adorable! We would definitely recommend and would love to return soon. "
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (34)
"Great property in such a cute area and just a short walk to the beach. Love the pool area and all the rooms were perfect for my friends and family."
Adorable Cottage with Covered Balconies and Private Pool

Cozy, family/pet friendly less than a block to white sandy beaches. Trolley stop

8.0 out of 10, Very Good, (1)
"Pros of this rental: the location to the beach which was less than 2 blocks away, easy off street parking, dog friendly, beach chairs, umbrella and toys for our use. The place is the right size for a couple or a small family. Cons: no dishwasher & the couch had a couple of large stains on them from previous renters, we covered them with sheets and notified the rental company"
Cozy, family/pet friendly less than a block to white sandy beaches. Trolley stop

Coastal Cottage On Holmes Beach With Private Heated Pool! 1 Block to beach.

9.8 out of 10, Exceptional, (68)
"Property is perfect. Great location, great set up, great owners. My only complaint is that I have to leave. "
Coastal Cottage On Holmes Beach With Private Heated Pool! 1 Block to beach.

Home with Private Backyard and Heated Pool - Gulf Breeze Villa B

9.8 out of 10, Exceptional, (28)
"We really enjoyed this property. Although it is a duplex, it has a private backyard and pool. Very quiet, we never heard the neighbor present on the other side. Perfect place for a couple to relax. Nice neighborhood. "
Home with Private Backyard and Heated Pool - Gulf Breeze Villa B

Anna Maria Cottage with Golf Cart

9.6 out of 10, Exceptional, (5)
"Great stay! Would recommend renting from these folks! Thanks again we really enjoyed our stay and will book again!"
Anna Maria Cottage with Golf Cart
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.
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Other property types in Anna Maria Island

Anna Maria Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (191)
"Property was fabulous. Very clean right on the ocean "
The price is SARĀ 2,298
SARĀ 2,908 total
includes taxes & fees
6 Apr - 7 Apr
Anna Maria Beach Resort

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (266)
"Beautiful boutique resort. Clean rooms, great pool and hot tub. Walking distance around Anna Maria Island. Parking included. I highly recommend :)"
The price is SARĀ 1,324
SARĀ 1,675 total
includes taxes & fees
22 Apr - 23 Apr
Pelican Post at Anna Maria Island Inn

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (49)
"Enjoyed our stay very much, Cannot wait to go back!!"
The price is SARĀ 2,283
SARĀ 4,860 total
includes taxes & fees
24 Apr - 25 Apr
Adorable Beach cottage just steps Bean Point beach!
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.

Frequently asked questions

What are the best cottages in Anna Maria Island?
Slide right into vacation mode and take life at a leisurely pace in one of Anna Maria Islandā€™s multiple cottages. With a total average guest review rating of 9.3, thereā€™s a place for everyone, no matter your style and budget. Many visitors to Bradenton Beach prefer staying at Queenā€™s Gate Resort, a 2.5-star cottage retreat with a swimming pool and a barbecue grill. Another top-rated choice in this buzzing city is 105b 12th Street South Front 2 Bedroom Apts By Redawning. This 3-star getaway has a swimming pool and a barbecue grill.
Why book your cottage in Anna Maria Island with Expedia?
Reserving a cottage in Anna Maria Island is as simple as entering your travel dates and choosing an ideal place for a getaway in nature. From ritzy retreats to affordable properties and cottages that feature amenities like a kitchenette, Expedia has something for all traveler styles. As for the best offers around? Weā€™ve got them as well!
How can I find cheap cottages in Anna Maria Island?
With Expediaā€™s helpful filter tool, sourcing cheap cottages in Anna Maria Island has never been simpler. To discover accommodations thatā€™ll make your hip pocket happy, tailor your search results by budget, amenities and star rating.