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Anna Maria Island vacation rentals

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Popular amenities for Anna Maria Island vacation rentals

Anna Maria Island house rentals

Guest favorite

Home in Anna Maria

5 out of 5 average rating, 22 reviews

Veselka - Canal front w private heated pool & dock

JulieRating, 5 stars2 months ago
We had such a fantastic stay, and Michael & Denzil were wonderful hosts. The house was just as it’s reflected in the photos, and was well stocked. We especially enjoyed the pool as well as the dock. Our boat captain was able to pick us up in our backyard, which was super convenient and allowed us to spend some time out on the water. We rented a golf cart that came in really handy for exploring, running to the corner store, and catching sunsets at Bean Point. We had an issue with the A/C during our stay, but Michael and Denzil were super responsive and had it fixed in hardly no time. A wonderful stay, wonderful hosts, and I highly recommend this lovely home. Hope to be back next year!
Guest favorite

Home in Holmes Beach

4.93 out of 5 average rating, 41 reviews

Backyard Bliss Anna Maria Island

DanaRating, 5 stars1 month ago
Loved this place! Looks exactly like pics. Few things I always look for- cold A/C, comfortable beds, strong water pressure and hot water when I shower. This place had all!! Place was clean and organized. Washer/dryer in garage. Pool was small but perfect after a hot day at the beach. Location was close to everything and convenient. Kit was great at communicating and very responsive. I would stay here again if I get back to the island!!!
Guest favorite

Home in Bradenton Beach

4.82 out of 5 average rating, 133 reviews

50 Steps to Beach Villa Hot Tub 1bd modern cottage

LucyRating, 5 stars1 month ago
I initially reserved three nights , then decided we couldn’t have enough of such beautiful home and beach !!! The home had literally everything you need!!! Please believe me when I say I over packed! Tom’s beach home has it all for the beach , chairs umbrellas ! Wheel cart ! Beach towels !! We ended staying 5 nights instead of three that’s how great the place is !! Even tho it was just two of us having one and half bathrooms was a luxury and I cannot say enough about the bed !! Super comfy , amazing pillows and clean!! Private front and fenced in ! Loved it loved it! This is our spot for ever. Literally we then decided it was so amazing there we we got hitched at South Coquina beach !!!! Woohooo omg had the best time . If I can post pictures I will ! If you are planning on visiting Ana Maria Island and want a relax and amazing stay that has it all ! Literally all !! This is your spot ! The marshmallow and chocolate complements of the house was so nice !!! Thank you till next stay !!!
Guest favorite

Home in Bradenton

4.9 out of 5 average rating, 41 reviews

The "Love shack" Bungalow

BillRating, 5 stars1 month ago
Had a great stay at the Love Shack. Felt comfortable and right at home. It had everything I could need. The location was perfect for access to dining, the beach and shopping. Enjoyed the screened porch in the evenings. Beautiful setting. I highly recommend and hope to stay there again in the future.
Guest favorite

Home in Holmes Beach

5 out of 5 average rating, 37 reviews

Couple’s Seatreat Summer Rate Specials

DianeRating, 5 stars1 month ago
Squeaky clean, comfortable bed, well equipped kitchen, super close to quiet beach, nice beach equipment provided. Enjoyed our week there.
Guest favorite

Home in Holmes Beach

4.95 out of 5 average rating, 94 reviews

The Peachy Beach House, steps to the gulf

ChrisRating, 5 stars2 months ago
The house was wonderful. We rotated between the beach (5 minute walk) and the backyard pool all week. There are many wonderful restaurants within a 10 minute golf cart ride. Frances was quick to respond anytime we had a question. We loved the house and the overall experience on the island. We’ll be back and will definitely book with Frances.
Guest favorite

Home in Indian Rocks Beach

4.98 out of 5 average rating, 119 reviews

Beachfront Bungalow w/ Pool & Hot Tub in IRB

JerrieRating, 5 stars1 month ago
The house was perfect! The pool and the beach access were amazing. They also have an abundance of beach and pool toys and beach chairs. The hot tub wouldn’t heat up while we were there but the hosts did refund me, which they really didn’t have to do. Safe to say we will definitely be booking again!
Guest favorite

Home in Bradenton

4.92 out of 5 average rating, 121 reviews

Luxurious 3 bedroom home with Hot Tub near AMI

SeasonRating, 5 stars2 months ago
Beautiful home! Spotless and clean. Comfy beds and decorated so nicely. Hot tub felt amazing after a long day at the beaches in the area.

Anna Maria Island villa rentals

Guest favorite

Villa in Safety Harbor

5 out of 5 average rating, 124 reviews

Villa Key West "Villas by Christine"

DebraRating, 5 stars1 week ago
Absolutely PERFECT!! Villa Key West is so cozy and comfortable. The decorations put you in a relaxed state of mind. We loved the back porch morning and night. The Villa is close to many excellent restaurants, shopping and the arts and music center. Dave and Christine were excellent hosts with a lot of recommendations for a good time. This is definitely a happy place to be. We can’t wait to go back!
Guest favorite

Villa in Tampa

4.91 out of 5 average rating, 158 reviews

Villa Perdomo Family

EmilyRating, 5 stars4 days ago
Antonio's place was wonderful! Very clean and spacious, perfect for a quick stop before boarding our cruise out of Tampa. The neighbors were a bit noisy but once inside the house you can't hear much at all! The outdoor space is beautiful and the house is very comfortable.
Guest favorite

Villa in Sarasota

4.84 out of 5 average rating, 128 reviews

Cozy, pet-friendly Home 3 miles to Siesta Key #1

IleanaRating, 5 stars7 months ago
Lauras place had all the amenities we needed, comfortable beds, dark bedrooms, beach accessories, laundry with a nice large washing machine, brita filter. The yard and patio areas were not nice enough to want to hang out in but that was irrelevant to us bc we were gone aaaalll day every day
Guest favorite

Villa in Holmes Beach

5 out of 5 average rating, 14 reviews

Waterfront in Paradise

SimonRating, 5 stars2 months ago
The easiest 5* review to write. Mimi’s place is fully refurbished, bright, modern and fully equipped. It is super clean, has the comfiest beds, well equipped kitchen, beach equipment, a dock with light/water hose and a patio with gas bbq, table, chairs and sun-beds. The location is great, on the water for boating & fishing, dolphin spotting, has floodlit tennis and pickle ball courts round the corner and a public boat ramp next to them too. The stunning beach is a short walk through to the opposite side of the island and Mimi has provided a trolley cart to use. We have had a great time made all the better by staying here.
Guest favorite

Villa in Siesta Key

4.91 out of 5 average rating, 151 reviews

Mermaid Villa Ocean Front!

MarcRating, 5 stars1 month ago
Couldn’t have picked a better spot! Barb was so easy to communicate with and very helpful. Place was just as described and made the trip so easy. Being that close to the downtown key was spectacular.
Guest favorite

Villa in Holmes Beach

4.97 out of 5 average rating, 65 reviews

Calico - Family Oasis - Steps from the Sand

SusanRating, 5 stars1 month ago
Our family was very impressed with this home and the area. Great care went into making sure that guests have such an enjoyable experience when staying there! Each room was carefully thought out and decorated as well.
Guest favorite

Villa in Tampa

4.86 out of 5 average rating, 110 reviews

Boho -Minimalist villa

HannahRating, 5 stars3 days ago
Very clean, great location, just like the pictures, and the hosts give very clear instructions
Guest favorite

Villa in Nokomis

4.92 out of 5 average rating, 151 reviews

NOV DIRTY! 159/nt Sarasota! New Villa 2 BR/2BTH

YvonneRating, 5 stars1 month ago
We had a wonderful and great time in this great and very clean accommodation. The furniture, the bed, the dishes, it's all made of high quality material. The washing machine with tumbler is also all new 👍👍 the hosts Chris and Michel, they were so helpful, very kind and friendly, always available, they gave us great recommendations for restaurants and excursions. The whole place feels like home. We come from Switzerland and have high expectations. The beautiful accommodation fulfilled all of our wishes. We'll be back 💙🇺🇲 Thank you Chris and Michelle 🙏

Anna Maria Island condo rentals

Guest favorite

Condo in Bradenton Beach

4.83 out of 5 average rating, 232 reviews

A+ location! Steps to beach, walk to Bridge St! #1

PhillipRating, 5 stars1 month ago
Sophie’s place was just right for us. We felt comfortable and at ease while unwinding there between our activities. You cannot beat walking a few yards to the idyllic beauty of Cortez Beach. The nearby trolley stop is so convenient for getting around the island. We were amazed that it was so quiet and peaceful. We would gladly stay with Sophie again.
Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 295 reviews

WE ARE OPEN—On the Beach; Siesta Key SunBum Studio

MarioRating, 5 stars1 month ago
The place is special. In addition to clean and truly steps from the beach, the hosts have thought of everything. They provide cooler, beach bag, umbrella, beach towels, sun screen, after sun lotion, k-cups for the coffee maker and more. It's a can't miss. The hosts are special people. Flexible, accommodating, helpful and want you to enjoy your vacation. Made a special effort to tell us the room was ready ahead of normal check-in. Our second stay was better than our first because of the improvements and we look forward to our third. Amazing hosts. Don't pass this one up...
Guest favorite

Condo in Indian Shores

4.99 out of 5 average rating, 108 reviews

Tropical Beachfront Penthouse-Beach Cottages II

BarryRating, 5 stars1 month ago
We have stayed at Beach Cottages several times, and this unit was the best yet! Large one bedroom, nicely furnished, easy access, great deck, plenty of little extras to make the stay comfortable and enjoyable. Will recommend to friends and hope to return next year.
Guest favorite

Condo in Longboat Key

4.91 out of 5 average rating, 160 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

ChrisRating, 5 stars2 months ago
Great location! Private beach, extremely quiet. Host gave great restaurant reccs. I would recommend or stay here again.
Guest favorite

Condo in Bradenton Beach

4.86 out of 5 average rating, 103 reviews

Oceanfront Condo for Beach Lovers

DonaldRating, 5 stars2 months ago
Ulrike's apartment was perfect for two couples. It was very clean and well maintained. The high quality furnishings were comfortable and met out needs. The view was outstanding! Parking under the first floor was a big plus, with an elevator to our floor. We felt safe and had privacy.
Guest favorite

Condo in Holmes Beach

4.85 out of 5 average rating, 143 reviews

Anna Maria Island-just a few steps to the beach

MarciRating, 5 stars2 months ago
Joe’s beach home is perfect! Has all the amenities of home! Fully functional kitchen. Wasn’t lacking anything. The condo itself was very clean and the complex was as well! We felt very safe and at home. The pool is right outside the door and down the steps. The beach is just a few steps away. Joe provides plenty of beach chairs, a beach umbrella and boogie boards etc. He is also very responsive to any questions we had. Could not have picked a better place for our first trip to AMI. Thanks Joe for allowing us to stay in your vacation home!!
Guest favorite

Condo in Longboat Key

4.99 out of 5 average rating, 112 reviews

One-Bedroom Condo on the Coast!

BradynRating, 5 stars1 month ago
This was my wife & I’s 2nd time staying with Heidi, but our 3rd visit to Silver Sands! *Heidi was booked the other time* We spoke to her months before our visit and told her we were coming back to the BEST AIR BNB with the BEST Host! She was just excited as we were. Throughout our visit she stayed in contact with us to make sure all was well and we were having a blast! The weather was fantastic and we couldn’t have had a better time. Luckily we dodged Hurricane Helene by just a couple of days, but there is no doubt we’ll be back.
Guest favorite

Condo in Holmes Beach

4.99 out of 5 average rating, 131 reviews

Beach Escape - Make Memories on Anna Maria Island!

PamRating, 5 stars2 months ago
My family and I were very comfortable in the condo during our week. It was roomy enough for the five of us and everything we needed was there. We loved the condo’s beachy decor and having two screened in porches. The short walk to the beach was not bad. It only took us a few minutes to get there. The host was very friendly and responsive, plus gave suggestions of restaurants, etc. We would definitely recommend staying here!

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