Search Cottages in Anna Maria Island

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Compare 58 Cottages in Anna Maria Island with updated reviews, rates, and availability.

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

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

9.8 out of 10, Exceptional, (23)
"Excellent location, close to the beach, stores, and restaurants. Wasn't as clean as it should be. There were spots around beds, that looked like they hadn't been cleaned in a long time. House was as advertised. Very nice for 2 couples and a small baby as we had. Pool was nice, although it needed some cleaning too. Overall, a very nice stay."
Great Location, steps to beach, 2 bd home w/ private pool
Charming cottage in quiet area, close to beach & bay.

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

9.8 out of 10, Exceptional, (254)
"Always wonder what the placees lookes like veerry small but cute places . My only sugggestion, whhsjcj make at mosdtcprlces ie stay is a ccoi"
Charming cottage in quiet area, close to beach & bay.
Shell Cottage - sleeps 2
Pool

Shell Cottage - sleeps 2

9.8 out of 10, Exceptional, (33)
"We could not ask for any better of a vacation"
Shell Cottage - sleeps 2
Castaway Cottage
Pool view from porch

Castaway Cottage

10.0 out of 10, Exceptional, (3)
"The property was very easy to find and was everything we expected and more.comfy beds and a really nice pool/hot tub combo. Being Very close to beach access was nice nothing beats a 5 minute stroll to the ocean."
Castaway Cottage
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
Fresh, bright open floor plan with new tongue and groove ceilings with kitchen skylight.

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

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

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

9.6 out of 10, Exceptional, (109)
"Great little cottage with amazing views, warm and welcoming place to stay! Owner was responsive and wonderful to work with, super flexible letting us get a golf cart dropped off before checkin and was great to work with. Great vacation in the beautiful quiet part of AMI!"
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Conveniently located Bungalow with private pool and tropical landscaping
Peach Bellini-Anna Maria Island Accommodations

Conveniently located Bungalow with private pool and tropical landscaping

9.4 out of 10, Exceptional, (23)
"We loved staying at this property! The pool and patio were perfect and location close to everything we needed. The walk to the beach was short for us- about 1.5 blocks, less than 5 minutes. Kitchen was stocked with pots, pans, baking dishes, sheet pans, etc. Having a washer and dryer on site was so convenient! I would definitely stay at this property again!"
Conveniently located Bungalow with private pool and tropical landscaping
Stay at Sun Daze: Private Pool, 3 Minutes to the Beach!
Private Pool, Outdoor Dining

Stay at Sun Daze: Private Pool, 3 Minutes to the Beach!

9.2 out of 10, Wonderful, (25)
"Great location within blocks of the beach, Gulf Drive, and many restaurants and shopping places, but still in a quiet neighborhood. All the needed items in the kitchen, beach towels, beach chairs, and cart. Beautifully landscaped and private backyard pool. Hope to make it back here again!"
Stay at Sun Daze: Private Pool, 3 Minutes to the Beach!
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Duplex Cottage seen from the Beach

Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

9.8 out of 10, Exceptional, (88)
"We loved the historical feel of the cottage and proximity to the beach. It was a relaxing, rejuvenating visit and we appreciated the hospitality basket upon our arrival. We have found most VRBO’s do not offer this simple but much appreciated touch. On top of everything, the owner, Alice, is a delight"
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Perfect family vacation home near the beach
Addison's Beach House

Perfect family vacation home near the beach

9.4 out of 10, Exceptional, (29)
"Had a wonderful week at this home. Large clean kitchen, good sized rooms and bathrooms. Pool was clean and larger than expected. Only issue was that the pool handle on the stairs was gone and broken off. Only covered by a pvc pipe that stuck out of the water and was a major hazard for our 2 small kids as they could have easily gotten very hurt. Not having a handle was also challenging for my older parents who stayed with us as it was hard to get in and out of the pool. I wish this would have...
Perfect family vacation home near the beach
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
Duplex Cottage seen from the patios

Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1

10.0 out of 10, Exceptional, (85)
"My wife and i had a great weekend in Alice's cottage..Pkace was clean and clearly well maintained. Oh and did i mention only a few steps to a white, soft sandy beach? Yes this was a great old Florida' experience. Not many of these gems left"
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
Enjoy Coastal Charm Throughout

Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...

9.6 out of 10, Exceptional, (40)
"The property was as described and absolutely amazing! It was beautiful inside, beds were comfortable, living area had comfortable furniture. Amenities were excellent. Not a bad thing to say about this place. Easy check in/out. Will definitely stay there again! "
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!
Road View

Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!

10.0 out of 10, Exceptional, (6)
"Great private pool and newer duplex, everything you could want, beach walking distance 5 min, great central spot to the island, the back yard and pool was the highlight for me..to be able to spend time at beach then come back and relax in pool is the best. Thank you for a nice stay"
Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!
Great location, cute cottage, 2 min walk to beach, 2bd/2ba home w/private pool
Exterior

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
Beach Dream Cottage: Steps from the Beach with Private Pool and Spa!
Beach Dream Cottage by Anna Maria Island Accommodations

Beach Dream Cottage: Steps from the Beach with Private Pool and Spa!

9.8 out of 10, Exceptional, (39)
"Great location. House was clean and pool was nice. It was a short 5 minute walk to the beach restaurants and ice cream. Nice family vacation would stay here again no concerns at all. "
Beach Dream Cottage: Steps from the Beach with Private Pool and Spa!
Bradenton Beach Home w/ Outdoor Bar & Heated Pool!
Pool

Bradenton Beach Home w/ Outdoor Bar & Heated Pool!

3.0 star property
2.0 out of 10, (1)
Bradenton Beach Home w/ Outdoor Bar & Heated Pool!
Charming Ground Level Resort Style 3 units Condo of a TRIPLEX- unit A
Property grounds

Charming Ground Level Resort Style 3 units Condo of a TRIPLEX- unit A

10.0 out of 10, Exceptional, (19)
"Our 2nd visit was everything we hoped for. Location is great, and accomodations were teriffic. You dont hsve to pack anything but a bathing suit! One slight observation. Lighting in the living area seemed dark. Maybe a slim floor lamplamp near the sofa or a dimmer on the overhead. However. Not enough of an issue to keep us rebooking. We will definitely be back."
Charming Ground Level Resort Style 3 units Condo of a TRIPLEX- unit A
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6

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
Newly renovated Cozy Beach Cottage A1/2 of a duplex, 3min walk to beach
Beautiful Holmes Beach sunset

Newly renovated Cozy Beach Cottage A1/2 of a duplex, 3min walk to beach

9.8 out of 10, Exceptional, (19)
"We are a family of two adults and one child who stayed 7 days at the duplex. The duplex is adequately equipped including extra towels, beach wagon, kitchen supplies/eating utensils, etc. Location wise you are a very short walk to the beach (same street there is an access point). You’ll have to walk (or drive) a bit further if you want a coffee shop or to the cluster of restaurants. The trolley is easily accessible equal distance on the bay side or the beach side. You can also easily walk to the...
Newly renovated Cozy Beach Cottage A1/2 of a duplex, 3min walk to 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.
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Other property types in Anna Maria Island

Anna Maria Beach Resort
Exterior

Anna Maria Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (188)
"All stay was friendly, very clean. Rooms cleaned daily. Would rate 5 "
The price is SAR 2,098
SAR 2,655 total
includes taxes & fees
24 Feb - 25 Feb
Anna Maria Beach Resort
Tradewinds Beach Resort
Living area

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (366)
"Me encantó el lugar, las casitas estan muy bien ubicadas con la playa, tienen un muelle que se puede pescar, la limpieza buena con excepción del sofá cama que no lo revisaron antes de entregar la habitación y estaba lleno de basura y el cubre colchón estaba sucio, lo recomiendo a pesar de este inconveniente."
Tradewinds Beach Resort
Pelican Post at Anna Maria Island Inn
Pool

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (265)
"Beautiful boutique resort. Clean rooms, great pool and hot tub. Walking distance around Anna Maria Island. Parking included. I highly recommend :)"
Pelican Post at Anna Maria Island Inn
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

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