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Anna Maria Island vacation rentals

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Top-rated vacation rentals in Anna Maria Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Condo in Holmes Beach
Beach Escape - Make Memories on Anna Maria Island!
Relax and unwind at this updated beach condo with a heated pool and outdoor shower overlooking a peaceful park. Very short stroll through the park and then about 150 steps to the white sand beach. Quaint condo community with only 8 units total. Wonderful couple escape or family getaway. Sleeps 2-6 guests. Private, covered 2 car parking. Laundry in unit. Storage room with beach wagon, beach chairs, and Weber grill. Location is a hidden gem close to everything you need for a relaxing island stay.
Feb 24 – Mar 3
$229 per night
4.99 out of 5 average rating, 120 reviews
Guest favorite
Home in Anna Maria
Private 30' Pool and Boat Dock - Rated best on AMI
* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles than staying at Sunshine Cottage, located in the City of Anna Maria!
Dec 2 – 9
$462 per night
4.93 out of 5 average rating, 152 reviews
Guest favorite
Home in Holmes Beach
Sea AMI
This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.
Sep 25 – Oct 2
$241 per night
4.95 out of 5 average rating, 155 reviews

Popular amenities for Anna Maria Island vacation rentals

Anna Maria Island house rentals

Guest favorite
Home in Bradenton Beach
Paradise! Steps2 Private Beach & Tropical Yard!
Dec 9 – 16
$449 per night
4.97 out of 5 average rating, 149 reviews
Guest favorite
Home in Bradenton Beach
Ohana Beachside 2 BR Bungalow - 150 ft from beach
Oct 23 – 30
$195 per night
4.89 out of 5 average rating, 236 reviews
Guest favorite
Home in Holmes Beach
Captain's Quarters at Spinnakers Vacation Cottages
Aug 24 – 31
$395 per night
4.99 out of 5 average rating, 153 reviews
Guest favorite
Home in Holmes Beach
Twin Palms: Big House Steps to Beach w/Lush Pool
Aug 10 – 17
$470 per night
4.97 out of 5 average rating, 120 reviews
Guest favorite
Home in Bradenton
Home near Anna Maria Beach - Hot Tub + Fire Pit
Aug 14 – 21
$177 per night
4.97 out of 5 average rating, 185 reviews
Guest favorite
Home in Anna Maria
ami skyview
Nov 20 – 27
$875 per night
5.0 out of 5 average rating, 25 reviews
Guest favorite
Home in Anna Maria
My Private Beach
Jan 27 – Feb 3
$995 per night
4.96 out of 5 average rating, 49 reviews
Guest favorite
Home in Anna Maria
Lamantin- 2 bed/2bath North End, beach 2 min walk
Dec 25 – Jan 1
$407 per night
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Anna Maria
Manatee Harbour - heated pool, with canal access
Apr 10 – 17
$448 per night
5.0 out of 5 average rating, 71 reviews
Guest favorite
Home in Anna Maria
Sea la Vie
Dec 9 – 16
$920 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Anna Maria
Anna Margaritas by Beach Boutique Rentals
Aug 27 – Sep 3
$518 per night
4.95 out of 5 average rating, 20 reviews
Guest favorite
Home in Holmes Beach
Last Minute Availability! Gulf Views, 86° Pool/Spa
Nov 5 – 12
$870 per night
4.95 out of 5 average rating, 59 reviews

Anna Maria Island villa rentals

Superhost
Villa in Redington Shores
Beach steps from your door. W/D Priv patio
Apr 25 – May 2
$156 per night
4.88 out of 5 average rating, 103 reviews
Guest favorite
Villa in Sarasota
Newly Renovated- 150 Yards to Beach & Restaurants!
Oct 13 – 20
$207 per night
4.96 out of 5 average rating, 129 reviews
Guest favorite
Villa in Siesta Key
Mermaid Villa Ocean Front!
Aug 20 – 27
$682 per night
4.9 out of 5 average rating, 130 reviews
Guest favorite
Villa in Bradenton
Elegant private home 3Bdr/3bth
Apr 25 – May 2
$245 per night
4.82 out of 5 average rating, 130 reviews
Guest favorite
Villa in Sarasota
Entire Standalone Villa,1.2k sf,1 block Lido Beach
Jun 21 – 28
$204 per night
4.9 out of 5 average rating, 180 reviews
Guest favorite
Villa in Clearwater
V1-2 BR, direct waterfront, 2 min walk to beach
Nov 6 – 13
$233 per night
4.91 out of 5 average rating, 122 reviews
Guest favorite
Villa in Safety Harbor
Villa Key West "Villas by Christine"
Dec 30 – Jan 6
$236 per night
5.0 out of 5 average rating, 108 reviews
Guest favorite
Villa in Sarasota
Hansen- Gorgeous 3BR/2BA Villa near Siesta Key
Apr 6 – 13
$286 per night
4.91 out of 5 average rating, 173 reviews
Guest favorite
Villa in Sarasota
Cozy, pet-friendly Home 3 miles to Siesta Key #1
Feb 20 – 27
$179 per night
4.84 out of 5 average rating, 123 reviews
Superhost
Villa in St. Petersburg
St. Pete Beach Oceanfront Villa Saltwater Pool
Dec 3 – 10
$285 per night
4.84 out of 5 average rating, 104 reviews
Guest favorite
Villa in Tampa
Busch Gardens, Moffitt, USF Charming Villa
Jul 29 – Aug 5
$119 per night
4.91 out of 5 average rating, 166 reviews
Guest favorite
Villa in Tampa
Villa Perdomo Family
Aug 11 – 18
$171 per night
4.92 out of 5 average rating, 121 reviews

Anna Maria Island condo rentals

Guest favorite
Condo in Longboat Key
Sweet Seabreeze Studio
Oct 19 – 26
$275 per night
4.97 out of 5 average rating, 146 reviews
Guest favorite
Condo in Holmes Beach
Blanco and Sunset Villas on Anna Maria Island
Oct 11 – 18
$240 per night
4.93 out of 5 average rating, 137 reviews
Guest favorite
Condo in Longboat Key
Beachfront Resort, Ocean View, Pool, Tennis, Gym
Nov 27 – Dec 4
$268 per night
4.93 out of 5 average rating, 142 reviews
Guest favorite
Condo in Holmes Beach
Beautiful beachfront condo for perfect vacation
Jul 3 – 10
$310 per night
4.96 out of 5 average rating, 116 reviews
Guest favorite
Condo in Bradenton Beach
A+ location! Steps to beach, walk to Bridge St! #1
Sep 22 – 29
$206 per night
4.82 out of 5 average rating, 211 reviews
Guest favorite
Condo in Bradenton Beach
Your Tropical Paradise Destination
Jun 10 – 17
$166 per night
4.89 out of 5 average rating, 115 reviews
Guest favorite
Condo in Holmes Beach
NEW listing on AMI! Walk to fabulous beach front!
Dec 21 – 28
$185 per night
4.98 out of 5 average rating, 107 reviews
Superhost
Condo in Holmes Beach
Steps from the beach
Sep 9 – 16
$219 per night
4.86 out of 5 average rating, 108 reviews
Guest favorite
Condo in Bradenton
Luxury 3/3 Margaritaville Resort
Aug 7 – 14
$293 per night
4.98 out of 5 average rating, 142 reviews
Guest favorite
Condo in Longboat Key
The Beach Condo Unit #107 Beachfront
Jul 19 – 26
$189 per night
4.86 out of 5 average rating, 154 reviews
Guest favorite
Condo in Longboat Key
SRQ/Longboat Key Beach - kid friendly/romantic B1
Sep 22 – 29
$172 per night
4.8 out of 5 average rating, 206 reviews
Guest favorite
Condo in Siesta Key
On the Beach; Siesta Key SunBum Studio
Dec 6 – 13
$259 per night
4.96 out of 5 average rating, 263 reviews

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