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Vacation rentals in Anna Maria Island

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Popular amenities for Anna Maria Island vacation rentals

House rentals in Anna Maria Island

Guest favorite
Home in Bradenton
4.9 out of 5 average rating, 10 reviews

Modern Resort-Style Townhouse

CrystalRating, 5 stars1 month ago
We had a great time at Gleb’s place. The townhouse was beautiful and very clean. Comfortable beds. The bunk bed has a trundle mattress on the bottom which worked out great for my youngest child. The clubhouse is amazing. Would definitely stay here again.
Guest favorite
Home in Tampa
4.88 out of 5 average rating, 334 reviews

Beautiful Home In S Tampa Near Water & Downtown

JulieRating, 5 stars2 weeks ago
We stayed for 6 nights while in town for our daughter’s wedding. Lovely historic home! Was spacious and clean, with nice little extras in the kitchen. Perfect location.
Guest favorite
Home in Sarasota
4.85 out of 5 average rating, 101 reviews

Private back yard. Southgate. 2 bedroom, 2 bath.

CharmianRating, 5 stars4 months ago
We had a wonderful stay at Evona’s house. It was so comfortable & nicely furnished with everything you could need for a relaxing stay. Super comfortable bed & sofa. Kitchen was great - spacious & well equipped. Especially appreciated the kettle being British! Loved the secluded garden & we had our thanksgiving dinner out there. The street was so quiet & next to the house was a pretty walkway which you could take - 10 mins walk to Aldi (supermarket) & the French bakery (highly recommended). Can’t say much about restaurants as we ate in most evenings but downtown is only a short ride away with lots of places to eat. Not a long drive to both Siesta & Lido beaches & Arlington park with its huge swimming pool is a very short drive or 20 mins walk away. We would love to return for thanksgiving next year.
Superhost
Home in Sarasota
4.75 out of 5 average rating, 114 reviews

Downtown New Construction House

SonyaRating, 5 stars2 weeks ago
Absolutely lovely accommodation, great air con, comfortable bed and fantastic location, walkable into town and beaches. Great communication. Thank you Maria!
Superhost
Home in Tampa
4.82 out of 5 average rating, 49 reviews

The day has arrived, enjoy.

MariaRating, 5 stars1 week ago
staying at Dianelis's place we're very nice had enough space for my family. the kids loved the pool. it were very peaceful and relaxing. love the outside area very relaxing for entertainment. thank you Dianelis's for the hospitality and letting me and my family stay in your home. also thank you for extending your checkout time for my family. really enjoyed and we will book again. thank you thank you
Superhost
Home in Tampa
4.74 out of 5 average rating, 102 reviews

Stylish Seminole Heights House

DesirRating, 5 stars3 months ago
This place was very cozy and literally walking distance from everything. Place was clean and it was super easy to contact the host and they contacted us back very quickly. The only that was a little inconvenient was we really needed the pull out couch for a bed and it was so uncomfortable and warn out that we had to buy an air mattress for us to accommodate the sleeping. Also there is only 1 tv for the whole place so when my niece who was sleeping in the living room went to bed we didn’t have entertainment throughout the night for the rest of us. My family works over night so we are night owls and more tvs would have helped a lot. Outside of that the place was amazing and definitely would book again with a smaller group
Guest favorite
Home in Wimauma
5 out of 5 average rating, 19 reviews

Lagoonside Escape

MichaelRating, 5 stars2 weeks ago
Perfect place for our quick trip. Host was very responsive and communicated well. She was able to answer all of my questions. The home was nice and in a quiet and safe area. Nice area to walk around the neighborhood. We will definitely rebook this place the next time we are in the area Thanks for being a great host
Superhost
Home in Holmes Beach
4.85 out of 5 average rating, 26 reviews

Fins Up – Cozy Retreat, Pool, Walk to Beach

TimoRating, 5 stars31 months ago
If Anna Maria island is one of the most beautiful destinations, this is definitely one of the most beautiful rentals to stay in. We enjoyed every moment there and were sad we had to leave 😊 Everything worked out very easy and the communication and service is great. Definately and recommendation!

Villa rentals in Anna Maria Island

Guest favorite
Villa in St. Petersburg
4.94 out of 5 average rating, 101 reviews

Heated Pool! Huge Walk In Shower! 5 min to beach!

JuliannaRating, 5 stars1 week ago
We had an amazing stay at this property! The location couldn’t be better—just a short drive to the beach. Everything needed for the beach in garage. The pool was clean, relaxing, and felt like a private oasis after a day in the sun. The place was spotless, beautifully decorated, and had everything we needed for a comfortable stay. Communication with the host was smooth and friendly throughout. Very comfortable beds! Had everything in the house needed. We would absolutely stay here again and highly recommend it to anyone looking for a beach getaway!
Top guest favorite
Villa in Sarasota
4.96 out of 5 average rating, 169 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

DarlaRating, 5 stars1 week ago
My mom and I came down for a long weekend and stayed at John’s place and we were thoroughly impressed! It was the nicest Air BnB I’ve stayed in! It was in a perfect location, walking distance to the beach and many restaurants and right across from a trolley stop too. The beds and bedding were SO comfy, that was probably the best I’ve ever slept in an Air BnB. The towels were oversized and fluffy, you wouldn’t think things like that would make a difference but they do. Everything was absolutely spotless and clean, all of the bedding and towels smelled fresh and clean too. They provided everything you could need, from toiletries and a hair dryer, to everything in the kitchen, to any beach gear that was needed. The house itself is very clean, comfy and cozy and you can tell they take pride in their place just from the landscaping outside, it makes it so pretty! We will definitely be back!
Guest favorite
Villa in Tampa
4.89 out of 5 average rating, 221 reviews

Busch Gardens, Moffitt, USF Tropical Villa

TerressRating, 5 stars2 days ago
The house was as described. It was clean and actually felt like a “home” when you walked in. Plenty of room, well stocked, and comfy. The location was PERFECT for our trip. Centrally located to shops, restaurants, and all the tourist attractions. BG, The Zoo, & The Aquarium were all less than 20 minutes away. We would definitely stay again.
Top guest favorite
Villa in Safety Harbor
5 out of 5 average rating, 133 reviews

Villa Key West "Villas by Christine"

DeniseRating, 5 stars4 months ago
We had an absolutely wonderful stay at Christine's Keywest Villa. It was clear that every detail had been carefully thought out. The Villa was immaculately clean. Highly recommend and we will definitely be back!
Superhost
Villa in Sarasota
4.75 out of 5 average rating, 126 reviews

Aloha Villa Pet Friendly 3 miles to Siesta Key #2

AwildaRating, 5 stars2 weeks ago
I visited Sarasota with my family from the state of Rhode Island from April 4 to April 7 and we stayed at Jason’s & Laura house and it was an amazing experience. The house was very clean and organized. The house is located on a great neighborhood, super safe and great amenities. The house was stocked with beach supplies like beach chairs, beach towels, a boogie board and a beach cooler that was so nice. The house was exactly what we were expecting, I would recommended to everyone. Thank you Josh and laura.
Guest favorite
Villa in Tampa
4.9 out of 5 average rating, 182 reviews

Villa Perdomo Family

JinaRating, 5 stars2 weeks ago
We loved our stay at Antonio’s! Place was very clean, had lots of space and had everything we needed. We used the fire pit and the pool each day. We were in town for the women’s basketball final four. Took a little longer to get downtown than we hoped but that was due to traffic. I would highly recommend!Antonio was very responsive, let us get in the house early and was quick to respond. If ever traveling to Tampa I would book again.
Guest favorite
Villa in Redington Shores
4.91 out of 5 average rating, 125 reviews

1 house to beach entrance. Peaceful. Walk to dine.

HannahRating, 5 stars8 months ago
This place was great! So close to the beach. We have been staying in this area for 20+ years and love coming here every time. Nancy’s home was clean and perfect for what we needed.
Superhost
Villa in Sarasota
4.89 out of 5 average rating, 202 reviews

Entire Standalone Villa,1.2k sf,1 block Lido Beach

IsaacRating, 5 stars1 week ago
Absolutely perfect location! Walking distance to Lido beach and St. Armand’s Circle. Rooms and amenities were very spacious and comfortable. Loved having beach equipment, beach towels, washer/dryer available. Easy checkin! Had the best time!

Condo rentals in Anna Maria Island

Guest favorite
Condo in Tampa
4.92 out of 5 average rating, 78 reviews

*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool

KatrenaRating, 5 stars3 weeks ago
Our family had a wonderful time at this condo! We enjoyed waking to see the ocean every day and also had enough space to relax on our vacation. Helena provides a beach bag with towels and sand toys that were a very nice touch for our beach day. The staff at the bar/restaurant were great and we also felt safe with the 24 hour security guards on duty. This place really made our trip extra special!
Superhost
Condo in Indian Shores
4.67 out of 5 average rating, 36 reviews

SPECTACULAR VIEW 3 bdm condo RIGHT ON the beach

ShanaRating, 5 stars17 months ago
The view was fantastic. It was quiet and close to anywhere we needed or wanted.
Guest favorite
Condo in Treasure Island
4.93 out of 5 average rating, 128 reviews

Beachfront w/ Stunning Sunsets in Prime Location.

KellyRating, 5 stars8 months ago
For an older building the unit was well maintained and was right on the beach and close to many restaurants as well as a grocery store.
Superhost
Condo in St. Pete Beach
4.82 out of 5 average rating, 72 reviews

Beach Nirvana - 2b /1b Condo

StaleyRating, 5 stars1 week ago
Our family really enjoyed our stay! The place was spacious enough for our family, and the location is absolutely perfect. We loved being able to have an easy walk to the beach, and to Paradise Grill (one of our favorite places to eat). It is also walking distance to other great restaurants. The place was very clean and the host was very friendly, responsive, and accommodating. Great stay!
Superhost
Condo in Madeira Beach
4.91 out of 5 average rating, 121 reviews

Arie Dam 302, Beach Front Condo - 2Bed/2Bath

MikeRating, 5 stars3 days ago
Our family of 6 had the best time! Our condo was so nice, clean, and comfortable. It was great to have beach towels and chairs to use as well!! The beach and view was amazing. We had no idea it would be so beautiful. The pool wasn’t quite ready but that didn’t matter (repairs due to the hurricane) the ocean was enough. Our son rented a fishing pole from Hubbards Marina and had the best time fishing off the shore while our other kids swam. We would go back and stay at the same place again. The beach was not crazy busy. Early mornings and late evenings were so peaceful.
Top guest favorite
Condo in Clearwater
4.93 out of 5 average rating, 145 reviews

5 *Waterfront Condo,3 Beds,2 Baths, Pool, HOT-TUB.

RobertRating, 5 stars4 days ago
The condo was beautiful. Clean and spacious. Lots of amenities. Close to the public beach, restaurants, bars, and shops. Plus David ordered a perfect week of weather for us! Wonderful.
Guest favorite
Condo in Bradenton
4.86 out of 5 average rating, 112 reviews

Florida Bella Rosa-2 spas & pools near IMG/beaches

LeahRating, 5 stars3 months ago
We are already looking to see when we can come back to Florida and stay in Daniel's rental again! It has everything you need, it is well-kept, and it is close to everything you want/need (the beach, Detwiler's, Publix, stores, restaurants). It is in a safe location. The Shorewalk ammenities (pools and hot tubs) are nice as well. Even though one pool's heater was broken, there was another pool to choose from and two hot tubs. He checked-in with us to make sure check-in went well and to make sure that our stay was going well. Daniel provided thorough instructions and recommendations for everything you could possibly need. He was a great host with a great home away from home!
Guest favorite
Condo in St. Petersburg
4.86 out of 5 average rating, 291 reviews

Breathtaking Waterview & Pool View Condo

Bob And ShellyRating, 5 stars1 month ago
Awesome view and wonderful host. Easy to find and easy access check in. Will return again.

Your guide to Anna Maria Island

Introduction

With its beautiful beaches and brilliant blue waters, this seven-mile barrier island offers a nostalgic idyll on the Gulf of Mexico. Over the years, residents have proudly resisted development, so Anna Maria’s vibe is decidedly low-key, with thatched-roof open-air bars and fresh fish restaurants dotting the waterfront. Here, where the island-wide speed limit is 35 miles per hour, the pace of life is literally slower. There are three small towns on the island — Bradenton Beach in the south, Holmes Beach in the middle, and the largest, Anna Maria, in the north — each with its own charms.


The best time to stay in a vacation rental in Anna Maria Island

January through April and October through December are popular months to visit as they offer temperatures between 70 and 80 degrees Fahrenheit. April and May bring temperatures in the high 80s, and June through September can be quite hot, with temperatures in the 90s. If you opt to book one of the area’s vacation rentals for a winter holiday, make sure to pack a layer for cooler evenings.


Top things to do in Anna Maria Island

Coquina Beach

You won’t have trouble finding a spot for your towel on this serene beach with sand dunes and waving beach grass. Although more sedate than nearby Manatee Public Beach, which draws more crowds, Coquina Beach doesn’t scrimp on amenities. There are picnic tables, bathrooms, and a lifeguard, making it an ideal spot for families. Bring a picnic, or fuel up at the Coquina Beach Cafe, which serves breakfast, fish tacos, and — for the grown-ups — frozen drinks at its tiki bar.

Coquina Baywalk

Get acquainted with the island’s unique ecosystem on this short walk through Leffis Key Preserve on an elevated wooden walkway. You’ll see mangrove trees alongside thousands of native plant species. You’re also likely to spot local wildlife such as geckos, crabs, stingrays, and birds — including the remarkable frigatebird, famous for showboating males who inflate an enormous red pouch under their beaks when courting.

Bean Point Beach

If you’re yearning for that Robinson Crusoe feel, Bean Point Beach is your best bet. Located on the northern tip of the island, this gorgeous stretch of sand is where the island’s founding family, chose to build their estate in 1892. Their homestead is long gone, but the beauty that drew them to the land is very much present. Off the beaten path, this public beach has no parking lots or lifeguard. What it does have is scenic splendor, a calming sense of privacy, and unobstructed sunset views.

Frequently Asked Questions

  • How is the weather in Anna Maria Island?

    Anna Maria Island has a subtropical climate with warm, humid summers and mild winters. The average summer temperature is 90°F (32°C), while in winter it drops to around 70°F (21°C). Rain is frequent from June to September, but showers are usually short and followed by sunshine.

  • What are some of the best things to do in Anna Maria Island?

    Visitors to Anna Maria Island often enjoy activities like paddling through the mangroves on a kayak, taking a dolphin watching tour, or exploring the Anna Maria Island Historical Society. For beach lovers, the island's seven miles (11.2 km) of coastline provide plenty of opportunities for swimming and shell collecting.

  • What is the best time of year to visit Anna Maria Island?

    The most popular time to visit Anna Maria Island is from February to May, when the weather is mild and rainfall is rare. During this time, the island hosts events such as the Anna Maria Island Art League's Springfest, a fine arts and crafts festival, and the Food and Wine on Pine, a celebration of local cuisine and vineyards.

  • What are the best places to stay in Anna Maria Island?

    The island is divided into three cities: Anna Maria, Holmes Beach, and Bradenton Beach. Each has its unique charm. Anna Maria is known for its laid-back vibe and historic buildings, Holmes Beach for its shopping centers and restaurants, and Bradenton Beach for its beachfront accommodations and lively nightlife.

  • What are the best places to visit in Anna Maria Island?

    Popular places to visit on Anna Maria Island include the Bean Point Beach, with its serene atmosphere and stunning sunsets, the Anna Maria Island Historical Museum, and the Anna Maria City Pier. The island also has a thriving arts scene, making the Island Gallery West a frequented spot.

  • What are some hiking trails in Anna Maria Island?

    Coquina Baywalk at Leffis Key is a great hike option in Anna Maria Island. It's a 1.5-mile (2.4 km) trail that meanders through mangrove tunnels and overlooks Sarasota Bay. Another recommended trail is the Robinson Preserve, just a 10-minute drive off the island. It has over 7 miles (11.2 km) of multi-use trails and is known for its diverse wildlife.

  • What are some family activities to do in Anna Maria Island?

    Families on Anna Maria Island frequently spend time building sandcastles at Manatee Public Beach, exploring the interactive exhibits at the Anna Maria Island Historical Society, or having a picnic at Bayfront Park. Additionally, the Island Scooter Store provides bike rentals for family cycling excursions.

  • What are some of the best day trip ideas in Anna Maria Island?

    Day trips from Anna Maria Island often include a visit to the Mote Marine Laboratory & Aquarium in Sarasota, a 30-minute drive away, or exploring the vibrant city of St. Petersburg, just an hour's drive from the island. Closer to home, the De Soto National Memorial offers historical exhibits and nature trails.

Destinations to explore