Anna Maria Vacation Rentals

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Browse Select Anna Maria Vacation Homes

Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (168)
"The best place "
The price is CA $745
CA $1,442 total
includes taxes & fees
Oct 20 - Oct 21
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Near Bean Point!! Short stays available! Heated Pool
9.4 out of 10, Exceptional, (37)
"The property was exactly as described and had everything that we would need through our vacation. We had a small issue with the lock and communication was easy, they were very responsive, and had the issue fixed without any interruption in our vacation. The location was fantastic! It was nice and quiet and my kids really enjoyed the pool. We would absolutely stay here again!"
Near Bean Point!! Short stays available! Heated Pool
Dreamy Beach Condo w/Incredible Location, Shared Pool, Washer/Dryer, Free WiFi
8.6 out of 10, Excellent, (36)
"Excellent location, walking distance to beach in steps not miles, can walk on beach to Sandbar Restaurant/Bar for dinner or drinks on beach. Beautiful house with everything you need all the comfort of home."
The price is CA $111
CA $377 total
includes taxes & fees
Sep 29 - Sep 30
Dreamy Beach Condo w/Incredible Location, Shared Pool, Washer/Dryer, Free WiFi
Dog-friendly home with amazing backyard, pool, spa, putting green & game room
9.6 out of 10, Exceptional, (14)
"Very nice walkable neighborhood. Walk to beach and restaurants. "
Dog-friendly home with amazing backyard, pool, spa, putting green & game room
Comfortable Vacation Retreat-Short Walk to Beach with Private Pool, Spa, AC,...
3.0 star property
8.0 out of 10, Very good, (1)
"The property is outdated but yet comfortable and cozy. It’s well equipped with everything you need. Few blocks walk to the beach. Only thing we would suggest to the owners is that the pool should be deep cleaned. It was covered in green moss and the water smelled unpleasantly. "
Comfortable Vacation Retreat-Short Walk to Beach with Private Pool, Spa, AC,...
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
9.8 out of 10, Exceptional, (68)
"We stopped in Anna Maria Island for three days on our road trip visiting Florida beaches. We loved Anna Maria Island. The Naut 2 Shabby Cottage was the perfect location for exploring the island. We loved the quaint charm of the cottage. "
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
4 Free Bikes for New Fall Stays Sep 3-Nov 16
9.8 out of 10, Exceptional, (28)
"We enjoyed our stay at this house. It had plenty of room for our family (2 parents, 2 kids, 1 grandparent). We loved the pool and outdoor area and the proximity to local restaurants and the beach. Overall it was nice and we’d stay again. Some things to be aware of though, the house is minimally stocked with things like trash bags, dish detergent, toilet paper, no coffee provided, etc so you’ll have to go buy those supplies. I know these aren’t required but they are nice to have. "
4 Free Bikes for New Fall Stays Sep 3-Nov 16
Canal-front home with private dock, covered lanai with heated pool and grill
9.2 out of 10, Wonderful, (70)
"I have beer coming to AMI for many years and love staying in the North end. This house is near everything we love about the area. Walking distance to the beach and short car ride or bike ride to AMI pier, Rod and Reel and all the great shops on Pine St. Pool area was great and my grandchildren spent most of their time out there. Also loved being g on the canal. Great getaway"
Canal-front home with private dock, covered lanai with heated pool and grill
MAGICAL NEST ON THE BEACH Heated pool & hot tub, 5 master suites DIRECT ON BEACH
10.0 out of 10, Exceptional, (126)
"Our family spent the week and there isn't one thing I'd change about our stay. Perfect location and the home was fantastic. We will definitely be back. "
MAGICAL NEST ON THE BEACH Heated pool & hot tub, 5 master suites DIRECT ON BEACH
Perfect summer vacation home! Close to Bean Point, great pool!
10.0 out of 10, Exceptional, (22)
"We had an amazing time even with the tropical storm effects! The team was very communicative leading up to our stay l, providing real time weather and recommendations and answering all of our questions. The house is beautiful! The kids loved the ping pong table and the pool was awesome!! The beds were so comfortable and the kitchen table was a great gathering place. We will definitely be staying here again!!"
Perfect summer vacation home! Close to Bean Point, great pool!
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
10.0 out of 10, Exceptional, (130)
"Our family loved this property for our recent trip to Anna Maria. Katy is an awesome host and the property has everything you need!"
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
Beach Cottage Close to Beach with Community Pool and Grill - Southern Breeze #6
10.0 out of 10, Exceptional, (4)
"This was the perfect stay for our group. Space was clean, kitchen was well-stocked with necessities (except a real knife). 5 min walk to the best beach on AMI, Bean Point. You could also take a short walk to the bay side to see the sunrise. The pool was clean and not busy. The communal washer/dryer seemed nice but our group didn’t use them. Parking was easy with a driveway directly next to the unit. Management was communicative and helpful prior to and during our arrival. Overall would highly...
Beach Cottage Close to Beach with Community Pool and Grill - Southern Breeze #6
Marias Way - 3BR/2BA Pool Home - Anna Maria City -By Island Real Estate Vacation
9.8 out of 10, Exceptional, (19)
"Location was as described clean and with all amenities listed. The bikes and beach stuff is really nice and allowed for extra fun. Pool area is great for night fun too. Excellent place if you want to hang out at the beach. "
Marias Way - 3BR/2BA Pool Home - Anna Maria City -By Island Real Estate Vacation
Vibrant Island Home w/ Pool, 1 Block to Beach
9.6 out of 10, Exceptional, (33)
"Property was fantastic. Very clean and had everything we needed for a few days on the island. The pool area great. Bedrooms, bathrooms were all clean. And bonus, close to everything! We’d definitely return to this house. "
Vibrant Island Home w/ Pool, 1 Block to Beach
4 Free Bikes for New Fall Stays Sep 3-Nov 16
9.6 out of 10, Exceptional, (31)
"The house is nice, clean and cozy. Underestimated how small the rooms were from the pictures, couldn’t really figure out which was the master. House is nicely decorated but mattresses are very hard and uncomfortable. Kitchen is well equipped but dining table only fits 4. Backyard looks like a little oasis but unfortunately mosquitoes didn’t let us enjoy. Highly recommend fumigating in the summer months. Overall very nice and cozy home just a bit too small for my family size of 7 Given the...
4 Free Bikes for New Fall Stays Sep 3-Nov 16
Charming gulf-front home right on the beach - stunning views, dogs welcome
9.4 out of 10, Exceptional, (113)
"Overall we thoroughly had a fantastic week at your place. Sum it up "Location, location, location". For the money what more could you ask for to be beach front. I will say it might be somewhat considered "dated" and could be spiffed up which would only help you get more rental money but my wife and I can't ask for any more. We plan on renting this every year as long as we can afford it. If you want any recommendations I would add a nice level deck running to the front of the house that would...
Charming gulf-front home right on the beach - stunning views, dogs welcome
Exclusive North End of AMI One Level Saltwater Heated Pool Canal Front Boat Dock
10.0 out of 10, Exceptional, (192)
"We have historically stayed in Holmes Beach. This was our first time staying closer to Anna Maria. And it did not disappoint. The house was a great layout for my in-laws and for my kids. The 2 bunk beds were perfect. The boys loved having a canal in the back. They actually found a few crabs to play with. Relaxing moments on the back porch with a cup of coffee or playing cornhole by the pool were great ways to spend the days, followed by a quick walk to get ice cream. An amazing home for...
Exclusive North End of AMI One Level Saltwater Heated Pool Canal Front Boat Dock
4 Free Bikes for New Fall Stays Sep 3-Nov 16
9.8 out of 10, Exceptional, (19)
"This home was perfect for our stay. It’s in a great location/neighborhood and convenient to walking to great local restaurants and shopping. The home itself if nice inside with a beautiful private backyard and pool. It was nice to come back from the beach at the end of the day and lounge in the pool. "
4 Free Bikes for New Fall Stays Sep 3-Nov 16
Spacious, Desirable North-End Gem on Canal w/ Dock & Heated Pool
9.8 out of 10, Exceptional, (103)
"Perfect place to stay and unwind. Family of 5 enjoyed our 9 day stay. Loved the pool and the outside areas. Kitchen had all the tools and utensils that we needed. Did use the grill which worked great. Overall very pleased with setup and location. Would definitely stay again!"
Spacious, Desirable North-End Gem on Canal w/ Dock & Heated Pool
Dog-friendly house w/ heated private lagoon pool - two blocks from the beach
9.0 out of 10, Wonderful, (84)
"Location is everything! Just minutes from the beach! The house was immaculate and customer service top notch. Completely fenced in backyard was perfect for our pups. Pool was refreshing after a day at the beach and the tall palms provided privacy from the homes next door."
Dog-friendly house w/ heated private lagoon pool - two blocks from the beach
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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.
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Other property types in Anna Maria

Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
9.8 out of 10, Exceptional, (76)
"This cottage is very well located. 2 blocks from the ocean. It has a pool and is in a quiet area. If you rent this cottage you wont be disappointed. My wife and I will rent it in the future that’s how nice it is. "
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
8.0 out of 10, Very good, (64)
"Overall this worked great for us. About 2 blocks from the gulf coast. Fishing access on an inlet behind the house and pool was great for us and kids. Out of the way for major island traffic but close enough to the coast to walk and enjoy it"
The price is CA $262
CA $757 total
includes taxes & fees
Oct 6 - Oct 7
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Dog-friendly house w/ heated private lagoon pool - two blocks from the beach
9.0 out of 10, Wonderful, (84)
"Location is everything! Just minutes from the beach! The house was immaculate and customer service top notch. Completely fenced in backyard was perfect for our pups. Pool was refreshing after a day at the beach and the tall palms provided privacy from the homes next door."
Dog-friendly house w/ heated private lagoon pool - two blocks from the 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.