Search Cottages in Anna Maria Island

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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, (188)
"We had stayed here for a month last year and once again this year and are looking forward to the same nextcyear. I cannot say enough wonderful things about the extraordinary efforts by Ed and Audrey to make our stay possible this year after the devastating hurricanes! We are eternally grateful "
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, (262)
"We loved our stay at the Castaway Cottage. The owners are so nice and met us on arrival. The house was clean and had all the things we needed to cook meals. The pool and landscaping are amazing and still feels very private. The proximity to Bean Point Beach was so convenient too especially with a little one. We also loved using the included golf cart and had so much fun riding around Anna Maria. This is a great place to stay for a small family or couple"
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 SAR 750
SAR 1,910 total
includes taxes & fees
23 Apr - 24 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, (268)
"We had everything we needed and then some. Our stay was comfortable and the location was perfect! We were close to the beach, shops, and restaurants. Thank you!"
Charming cottage in quiet area, close to beach & bay.

Shell Cottage - sleeps 2

9.8 out of 10, Exceptional, (34)
"Shell Cottage was cute as can be . It was very clean , beautifully decorated and well equipped. However; there is an alarm on the entry door that is ear shattering. The check-in information states it is part of the rental license rules which I understand. There was no grey box on the outside of the door which can be pressed to allow entry within 45 seconds before the alarm goes off. There was a button on the inside that allowed us to leave the cottage.. I’m not sure I would stay here again...
Shell Cottage - sleeps 2

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

9.8 out of 10, Exceptional, (28)
"If we had better weather we would have enjoyed the pool and quiet backyard retreat Overall was a great place to stay. Great location Funny thing the place we stayed at last year was right behind us but this place was sooo much better!"
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, (128)
"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

8.8 out of 10, Excellent, (23)
"Great location, very comfortable property! We loved the 2 covered porch areas at the front and back of the unit. We had a little trouble with the AC but the owner was very responsive. We would certainly rent this unit again!"
The price is SAR 1,418
SAR 3,846 total
includes taxes & fees
20 May - 21 May
Beautiful Condo on Pine Ave, 2 Blocks to Beach

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

8.8 out of 10, Excellent, (73)
"It was myself, husband and 2.5 year old son who stayed at the property. The pool, proximity to the beach and walking distance to restaurants and ice cream shops couldn't have been any better. The house itself has some serious wear and tear though. Although I believe the cleaners did a great job, the condition/cleanliness of the furniture, and wear and tear on the house made it feel a little uncomfortable and dirty. We ate in for every meal and felt the kitchen was sparsely stocked, but we made...
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)
"Perfect location with anything needed. Was great to get out of the cold and snow and into the sunshine. Forest time on Anna Maria Island and this VRBO exceeded our expectations. "
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, (19)
"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

8.6 out of 10, Excellent, (4)
"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, (36)
"We vacation multiple times at AMI. Our group loved the location right on Pine Avenue. Amenities were all top-notch everything you need. It was there."
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, (69)
"We had a blast at the Coastal Cottage! Our kids absolutely loved the pool, the house was in perfect shape and so clean, and Ken and Susie were excellent hosts. The location was great - quiet and close to the beach as well as a short trip to restaurants and shops. It was our first trip to AMI and I can’t wait to come back."
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, (29)
"Perfect place for a couple with amenities galore"
Home with Private Backyard and Heated Pool - Gulf Breeze Villa B

Anna Maria Cottage with Golf Cart

9.8 out of 10, Exceptional, (7)
"This cottage was the perfect anniversary getaway. Centrally located and easy to visit the beaches and explore the island on the provided golfcart"
Anna Maria Cottage with Golf Cart

Seahorse Cottage - sleeps 2 guests in 1 bedroom

9.8 out of 10, Exceptional, (49)
"Our stay was great! Cottage had everything we needed. "
Seahorse Cottage - sleeps 2 guests in 1 bedroom
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, (198)
"Highly recommend this property. Our unit was very updated and had a full kitchen with everything we needed for a comfortable stay. The beds were comfortable. The swimming pool was great and heated and the beach access was within a few steps. The location was quaint but easily accessible and lots of dining options near by. Would stay here again. "
The price is SAR 1,944
SAR 2,460 total
includes taxes & fees
21 Apr - 22 Apr
Anna Maria Beach Resort

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (267)
"Beautiful boutique resort. Clean rooms, great pool and hot tub. Walking distance around Anna Maria Island. Parking included. I highly recommend :)"
The price is SAR 1,147
SAR 1,451 total
includes taxes & fees
21 Apr - 22 Apr
Pelican Post at Anna Maria Island Inn

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (372)
"Family and I stayed here for spring break and the facilities were awesome. The staff was friendly and helpful. The are is still cleaning up after the hurricane, but it definitely did not affect the fun in the area. We will be planning a return trip."
Tradewinds Beach Resort
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.