Search Cottages in Anna Maria

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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 24 Cottages in Anna Maria with updated reviews, rates, and availability.

We will be accepting new reservations from January 2025 going forward only.
Beach nearby, sun loungers, beach towels

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!
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (261)
"Family of 4 stayed here comfortably for 3 nights in April. Had an excellent time on the island. And we were really impressed with the property and its location. Cool little trail, steps from the door take you straight to Bean Point."
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!
Charming cottage in quiet area, close to beach & bay.
Sun loungers, beach towels

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
Beach nearby

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
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Terrace/patio

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!"
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Beach

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

8.8 out of 10, Excellent, (72)
"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
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Beach nearby

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
A heated pool

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (35)
"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
Seahorse Cottage - sleeps 2 guests in 1 bedroom
Beach nearby

Seahorse Cottage - sleeps 2 guests in 1 bedroom

9.8 out of 10, Exceptional, (48)
"Seahorse Cottage was perfect and fit all our needs. Close to the beach, great pool, and the accommodations were very nice. We both would have preferred a firmer mattress on the bed but that would not stop us from visiting again. Idyllic Holiday Properties was very easy to deal with and Liane had excellent communication skills in planning for our trip. Debbie, the Property Manager in Anna Maria, was also very quick to respond to texts while we were there. All around, a great experience and a...
Seahorse Cottage - sleeps 2 guests in 1 bedroom
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
A heated pool

Beautiful, well-maintained home w/ heated private pool - walk to beach & dining

9.6 out of 10, Exceptional, (77)
"We were in town for a lacrosse tournament and this house was so perfect, clean and relaxing."
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Beach towels

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

9.6 out of 10, Exceptional, (112)
"Located fairly close to City Pier area. View of inlet. There are 15 wooden steps up into the house. Quiet neighborhood. "
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Fridge, microwave, oven, stovetop

Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

9.8 out of 10, Exceptional, (71)
"The location of this property was unbeatable. Steps to the beach and restaurants but still peaceful and quiet. Anthony and Joann were more than gracious hosts and made me, my husband and my kids feel very welcome."
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel
Property grounds

Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel

10.0 out of 10, Exceptional, (35)
"Great house, great location, great weather!"
Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel
Starfish Cottage - sleeps 4 guests in 2 bedrooms
Beach nearby

Starfish Cottage - sleeps 4 guests in 2 bedrooms

9.8 out of 10, Exceptional, (42)
"Every thing was just as described on the listing. Cute cottage super close to the beach with a cute pool in the backyard. We had a great vacation! "
Starfish Cottage - sleeps 4 guests in 2 bedrooms
Beautiful Guest House Near the Beach with Private Pool!
A heated pool

Beautiful Guest House Near the Beach with Private Pool!

8.4 out of 10, Very Good, (26)
"Great place, super clean, convenient location, awesome pool!"
Beautiful Guest House Near the Beach with Private Pool!
Guest House in the Business District with Private Pool
Fridge, microwave, oven, stovetop

Guest House in the Business District with Private Pool

9.4 out of 10, Exceptional, (22)
"Location was amazing! Walking distance to all shops, restaurants and beach. Property had everything we needed even beach chairs which was so great since we flew. It was clean and comfortable. "
Guest House in the Business District with Private Pool
Canalfront Anna Maria Cottage w/ Pool & Hot Tub!
Interior

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

3.0 star property
Canalfront Anna Maria Cottage w/ Pool & Hot Tub!
Serenity Cottage
Pool

Serenity Cottage

2.0 star property
Serenity Cottage
Sunrise Shore
Outdoor pool

Sunrise Shore

3.5 star property
Sunrise Shore
Going Coastal by SeaBreeze
Cottage, 2 Bedrooms, Private Pool, Canal View | Terrace/patio

Going Coastal by SeaBreeze

3.0 star property
Going Coastal by SeaBreeze
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

Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!
Aerial view

Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

9.6 out of 10, Exceptional, (11)
"The interior was all new. Furnishings, decor, kitchen supplies, and everything fresh and tastefully done. Quiet neighborhood just a couple blocks from beach. Exterior privacy will improve as landscape recovers. Parking and access easy. "
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!
Adorable Beach cottage just steps Bean Point beach!
A heated pool

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (51)
"This house felt like it was brand new. Loves hanging in the backyard by the soaking pool. Sun hit part of the backyard all day. House was well stocked for everything you need for a relaxing beach vacation. "
Adorable Beach cottage just steps Bean Point beach!
Anna Maria Home with Saltwater Pool Near Beaches & Shopping - Sunrise Shore
A heated pool

Anna Maria Home with Saltwater Pool Near Beaches & Shopping - Sunrise Shore

9.4 out of 10, Exceptional, (47)
"This was a great stay, the only reason I didn't give a 5 star on everything was because we were missing a bedroom door on the main level. "
Anna Maria Home with Saltwater Pool Near Beaches & Shopping - Sunrise Shore
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.