Search Anna Maria Island Cottage Rentals from CA $253

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Browse Select Anna Maria Island Cottages

Outdoor pool, pool umbrellas, sun loungers
Queen's Gate Resort
2.5 star property
9.0 out of 10, Wonderful, (379)
"Amazing property and super friendly staff. We had the best time and our room was perfect. Full kitchen with everything we needed to make any meal. Washer/dryer that we could use plus so many little extras in the supply house we could use if needed! Pool was clean and beautiful. Beach was super close, just about a minutes walk away. Will definitely be returning in the future! "
Queen's Gate Resort
Beach nearby, sun loungers, beach towels
Charming cottage in quiet area, close to beach & bay.
10.0 out of 10, Exceptional, (233)
"This charming 2 bed, 1 bath cottage is in the perfect location. It is in walking distance to coffee shops, breakfast spots and dinner restaurants. Close to the beach one direction and city pier the other. It is well stocked with all you would need and exceptionally clean. The screened porch in back with solar lighting in the back yard is ideal for your evening glass of wine! Definitely recommend!"
Charming cottage in quiet area, close to beach & bay.
A heated pool
Great location, cute cottage, short walk to beach, 2 bd home w/private pool
10.0 out of 10, Exceptional, (24)
"We were very pleased with this rental, particularly the private pool and 3 minute walk to a pristine beach."
Great location, cute cottage, short walk to beach, 2 bd home w/private pool
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Pool
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
9.8 out of 10, Exceptional, (37)
"Love everything about this place! Great location! Close to beach, close to shopping, close to restaurants!! What more could we ask for! Will be back!!"
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
Property grounds
Sunny 1-bedroom island cottage with shared pool
10.0 out of 10, Exceptional, (17)
"This was a perfect little spot...super clean, super cute, super easy walk to the beach."
The price is CA $410
CA $669 total
includes taxes & fees
May 28 - May 29
Sunny 1-bedroom island cottage with shared pool
Aerial view
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
9.4 out of 10, Exceptional, (17)
"We had a lovely stay at this rental! Kids loved proximity to beach and places to go. Easy check in and out. Owners communicated very well. Nice stay on AMI!"
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
Beach nearby
COZY APT IN QUADRAPLEX HOME. 1BR/1BA Sleeps up to 4. POOLSIDE. STEPS TO BEACH!
10.0 out of 10, Exceptional, (147)
"Family beaxh vacation mom, dad and 2 children"
COZY APT IN QUADRAPLEX HOME. 1BR/1BA Sleeps up to 4. POOLSIDE. STEPS TO BEACH!
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
9.8 out of 10, Exceptional, (67)
"My friend and I, to celebrate Mother's Day without kids, spend 4 days at this delightful cottage on Anna Maria Island. I have only glowing reports regarding the location and the hosts. This cute and old-fashioned cottage sits in a great location and is in walking distance to shops, the Anna Maria Pier, restaurants and especially, the beach! It sits next to Capt Anthony's fish market which would have been interesting to watch; however, the owners were on vacation so we missed the action. Joanne...
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Property grounds
Cheerful 1-bedroom Island Cottage with shared pool
9.6 out of 10, Exceptional, (32)
"My husband and I rented this unit for our 30th wedding anniversary and we cannot be happier with our decision! The location is perfect, just a short walk to the beach, or to the free trolley bus stop…no need to move the car if you don’t want to. The apartment was perfectly clean and beautifully decorated. My only recommendation is that the mattress needs to be changed and the coffee maker requires Keurig coffee cups and the ones left at the apartment, were from a different brand so we couldn’t...
Cheerful 1-bedroom Island Cottage with shared pool
Beach towels
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
9.6 out of 10, Exceptional, (34)
"Stayed for 9 nights and had a wonderful time. Twin dolphin is a clean, cute, and cozy place to stay. Very convenient area for walking. I highly recommend staying here. You won’t regret it."
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
A heated pool
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
9.6 out of 10, Exceptional, (72)
"We loved our stay. Everything was perfect. We have 3 kids ages 3-7 and the layout and location was excellent. I also appreciate how clean it was when we arrived. Kitchen is very well stocked and we did most meals at the home. The walk to beach is just across the street. Highly recommend!"
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
Beach nearby
Experience the passion of hospitality, cleaning, and good location!
9.6 out of 10, Exceptional, (124)
"The place was quaint and was the perfect location to the beach and downtown area."
The price is CA $253
CA $458 total
includes taxes & fees
May 30 - May 31
Experience the passion of hospitality, cleaning, and good location!
Beach nearby, beach towels
Charming & Vintage Anna Maria Cottage. Easy Walk to Beaches, Stroll Pine Avenue!
8.0 out of 10, Very good, (3)
"Quiet, shaded convenient location. The Enchanted Cottage was exactly as advertised and a wonderful choice for two seniors. We loved it."
Charming & Vintage Anna Maria Cottage. Easy Walk to Beaches, Stroll Pine Avenue!
Private kitchen
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
10.0 out of 10, Exceptional, (12)
"We stayed here for our honeymoon, and had the BEST time. It was so conveniently located, and we had everything we needed. My only complaint was the furniture was a tad uncomfortable, but we definitely plan to stay here again so it wasn’t that bad. It was nice that we had nice beach chairs and umbrellas, and we didn’t have to buy or rent anything. Definitely one of my favorite VRBO’s."
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
Sun loungers, beach towels
Romantic, Cute Cottage on Anna Maria Island. Close To Everything. Pet Friendly!
10.0 out of 10, Exceptional, (9)
"Amazing stay for Spring break 2024. Your cottage was absolutely perfect and we had an amazing time exploring all of beautiful AMI. Loved watching the sunset from the rooftop and having our morning coffee on the back deck. Boys loved the outdoor shower and everything about your cottage was perfect! We can’t wait to come back! Perfect location in all the action. Loved the bike path over to Longboat key and Beer Can Island was such a gem. Thank you for an amazing time. Cheers!!!"
Romantic, Cute Cottage on Anna Maria Island. Close To Everything. Pet Friendly!
Beach nearby
A lovely 2 bed and 2 bath property just moments from the beach
10.0 out of 10, Exceptional, (18)
"Perfect location, calm, relax, peaceful"
A lovely 2 bed and 2 bath property just moments from the beach
Outdoor pool, a heated pool
New 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"
New Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!
Beach nearby
Vibrant Anna Maria Island Retreat: Walk to Gulf!
9.2 out of 10, Wonderful, (21)
"Perfect little getaway. Cottage was clean and absolutely adorable. The pool area was like a tropical paradise. The landscaping was perfect and added privacy from nearby neighbors. 2 minute walk to the beach was perfect. ‘Big Jenga’ was a huge hit and we played for hours. Would highly recommend and can’t wait to go back."
Vibrant Anna Maria Island Retreat: Walk to Gulf!
On the beach
Sailfish Gulf Suites #2, Beachfront, Steps to the Sand
9.8 out of 10, Exceptional, (9)
"Great host, very responsive. Excellent location - on the beach and close to Manatee Beach and amenities including the trolley stop. We loved our stay and hope to return."
Sailfish Gulf Suites #2, Beachfront, Steps to the Sand
Fridge, microwave, oven, stovetop
A night full of stillness - a breeze comes telling the stars too many to count.
9.6 out of 10, Exceptional, (4)
"This vacation home is spotless and very cozy. Big back yard if you want to relax outside or just a walk to the beach. Near restaurants and shops…very nicely located. The owner was great and provided everything we needed. Thank you for a great stay!"
A night full of stillness - a breeze comes telling the stars too many to count.
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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.

Other property types in Anna Maria Island

On the beach, white sand, beach towels
Anna Maria Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (155)
"Had an amazing stay. Will definitely be back!"
The price is CA $918
CA $1,152 total
includes taxes & fees
Jun 2 - Jun 3
Anna Maria Beach Resort
A heated pool
Perfectly Located Home with Pool and Spa
9.8 out of 10, Exceptional, (21)
"The house is great, with the ease of having a pool and the beach being only 2 blocks away. This was our first time visiting Anna Maria. We have been finding other options the last couple years since we used to go to Captiva and that was destroyed in the hurricane almost 2 years ago. The island is pretty small but has different sections to explore. We enjoyed Coquina beach for a coupem hours one day, the restaurants were good very vactiony normal island grub type places. We did enjoy a great meal...
Perfectly Located Home with Pool and Spa
Garden
Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (188)
"My favorite hotel to stay! Super clean and peaceful! My kids love the pool and beach is two minute walk. Stores and food are walking distance. "
The price is CA $474
CA $594 total
includes taxes & fees
May 29 - May 30
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.

Anna Maria Island Cottages information

Number of reviews
1,161
Accommodation
59 Cottages
Lowest Price
CA $253
Highest Price
CA $410

Recent Reviews in Anna Maria Island
Expedia verified reviews