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Anna Maria Island vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Anna Maria Island

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

Guest favorite

Home in Holmes Beach

4.96 out of 5 average rating, 157 reviews

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.

Oct 7 – 14

ﺩ.ﺇ1,101 per night
Guest favorite

Guest suite in Sarasota

4.98 out of 5 average rating, 100 reviews

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

Oct 15 – 22

ﺩ.ﺇ422 per night
Guest favorite

Condo in Redington Beach

4.97 out of 5 average rating, 455 reviews

AmazingBeachCondo/NoCleaningFee/AwesomeAmenities

Welcome to our condo. We have provided you with just about everything you need to come and vacation at this amazing beach area. The condo is right by the heated pool and a 2-minute walk to the beach. The complex has high-speed internet throughout and a laundry facility. Shopping/Grocery/Pharmacy are all close by. Restaurants/bars very close by. This is an amazing area of Florida, with so many things to see and do. You will love it here. We have also provided bikes for your use to get around.

Nov 9 – 16

ﺩ.ﺇ396 per night

Popular amenities for Anna Maria Island vacation rentals

Anna Maria Island house rentals

Guest favorite

Home in Anna Maria

4.93 out of 5 average rating, 152 reviews

Private 30' Pool and Boat Dock - Rated best on AMI

Oct 23 – 30

ﺩ.ﺇ1,952 per night
Guest favorite

Home in Bradenton Beach

4.97 out of 5 average rating, 149 reviews

Paradise! Steps2 Private Beach & Tropical Yard!

Dec 5 – 12

ﺩ.ﺇ1,897 per night
Guest favorite

Home in Holmes Beach

4.99 out of 5 average rating, 153 reviews

Captain's Quarters at Spinnakers Vacation Cottages

Jul 13 – 20

ﺩ.ﺇ1,678 per night
Guest favorite

Home in Bradenton

4.91 out of 5 average rating, 251 reviews

Palm Retreat Gold: Luxury Edition of #1 Rental

Dec 5 – 12

ﺩ.ﺇ1,073 per night
Guest favorite

Home in Bradenton

4.94 out of 5 average rating, 150 reviews

Peaceful Braden River Oasis: Cottage

Aug 30 – Sep 6

ﺩ.ﺇ379 per night
Guest favorite

Home in Bradenton Beach

4.89 out of 5 average rating, 236 reviews

Ohana Beachside 2 BR Bungalow - 150 ft from beach

Jan 4 – 11

ﺩ.ﺇ983 per night
Guest favorite

Home in Holmes Beach

4.97 out of 5 average rating, 123 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Aug 25 – Sep 1

ﺩ.ﺇ1,657 per night
Guest favorite

Home in Holmes Beach

4.91 out of 5 average rating, 23 reviews

Enjoy AMI sunsets | Chic home w/ Saltwater pool!

Dec 6 – 13

ﺩ.ﺇ689 per night
Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 11 reviews

Lamantin- 2 bed/2bath North End, beach 2 min walk

Aug 29 – Sep 5

ﺩ.ﺇ1,508 per night
Guest favorite

Home in Holmes Beach

5.0 out of 5 average rating, 46 reviews

Private Luxurious Ground Level Home

Sep 16 – 23

ﺩ.ﺇ1,489 per night
Guest favorite

Home in Anna Maria

4.88 out of 5 average rating, 34 reviews

Bean Pt. Bungalow - Half duplex w/private pool

Dec 5 – 12

ﺩ.ﺇ1,485 per night
Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 28 reviews

ami skyview

Sep 25 – Oct 2

ﺩ.ﺇ3,656 per night

Anna Maria Island villa rentals

Superhost

Villa in Nokomis

4.91 out of 5 average rating, 138 reviews

APR SALE! Sarasota Family BEACH Villa 2KING BR/2BA

Jun 16 – 23

ﺩ.ﺇ606 per night
Guest favorite

Villa in Siesta Key

4.9 out of 5 average rating, 133 reviews

Mermaid Villa Ocean Front!

Sep 21 – 28

ﺩ.ﺇ2,877 per night
Guest favorite

Villa in Sarasota

4.96 out of 5 average rating, 130 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

Jan 10 – 17

ﺩ.ﺇ1,058 per night
Guest favorite

Villa in Sarasota

4.89 out of 5 average rating, 181 reviews

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

Sep 13 – 20

ﺩ.ﺇ857 per night
Guest favorite

Villa in Redington Shores

4.9 out of 5 average rating, 121 reviews

Outstanding location 1 min to sand W/D Priv patio

Oct 8 – 15

ﺩ.ﺇ1,113 per night
Guest favorite

Villa in Bradenton

4.83 out of 5 average rating, 133 reviews

Elegant private home 3Bdr/3bth

Jun 29 – Jul 6

ﺩ.ﺇ1,105 per night
Guest favorite

Villa in Safety Harbor

5.0 out of 5 average rating, 109 reviews

Villa Key West "Villas by Christine"

Jun 1 – 8

ﺩ.ﺇ699 per night
Guest favorite

Villa in Clearwater

4.91 out of 5 average rating, 210 reviews

V3- 1 BR, waterfront villa, 2 min walk 2 beach

Dec 14 – 21

ﺩ.ﺇ686 per night
Superhost

Villa in St. Petersburg

4.84 out of 5 average rating, 106 reviews

St. Pete Beach Oceanfront Villa Saltwater Pool

Dec 3 – 10

ﺩ.ﺇ1,207 per night
Guest favorite

Villa in Holmes Beach

5.0 out of 5 average rating, 9 reviews

Waterfront in Paradise

Jul 9 – 16

ﺩ.ﺇ1,555 per night
Guest favorite

Villa in Holmes Beach

4.98 out of 5 average rating, 50 reviews

Calico - Family Oasis - Steps from the Sand

Aug 17 – 24

ﺩ.ﺇ2,416 per night
Superhost

Villa in HOLMES BEACH

4.7 out of 5 average rating, 23 reviews

Location! Steps from Manatee Beach 2BR

Jul 15 – 22

ﺩ.ﺇ731 per night

Anna Maria Island condo rentals

Guest favorite

Condo in Bradenton Beach

4.9 out of 5 average rating, 123 reviews

Beachfront condo in paradise

Dec 6 – 13

ﺩ.ﺇ1,192 per night
Guest favorite

Condo in Holmes Beach

4.96 out of 5 average rating, 116 reviews

Beautiful beachfront condo for perfect vacation

Jul 3 – 10

ﺩ.ﺇ1,316 per night
Guest favorite

Condo in Holmes Beach

4.99 out of 5 average rating, 121 reviews

Beach Escape - Make Memories on Anna Maria Island!

Oct 24 – 31

ﺩ.ﺇ975 per night
Guest favorite

Condo in Redington Beach

4.92 out of 5 average rating, 106 reviews

Royal Orleans and Redington Beach ( Studio 203 )

Dec 8 – 15

ﺩ.ﺇ344 per night
Guest favorite

Condo in Holmes Beach

4.92 out of 5 average rating, 156 reviews

Anna Maria Beach Place...footsteps to the sands

Nov 26 – Dec 3

ﺩ.ﺇ828 per night
Guest favorite

Condo in Longboat Key

4.93 out of 5 average rating, 143 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Nov 21 – 28

ﺩ.ﺇ1,129 per night
Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 142 reviews

1 BR direct beachfront! Now available May 22-27!

Oct 30 – Nov 6

ﺩ.ﺇ576 per night
Guest favorite

Condo in St. Pete Beach

4.92 out of 5 average rating, 200 reviews

Sunset Beach Condo in Treasure Island

Sep 13 – 20

ﺩ.ﺇ478 per night
Guest favorite

Condo in Siesta Key

4.9 out of 5 average rating, 149 reviews

Cozy Siesta Key studio 5 minute walk to Village

Nov 12 – 19

ﺩ.ﺇ549 per night
Guest favorite

Condo in Indian Rocks Beach

4.79 out of 5 average rating, 223 reviews

Waterfront Condo w/ Boat dock, 2 min walk to beach

Mar 20 – 27

ﺩ.ﺇ523 per night
Guest favorite

Condo in Treasure Island

4.99 out of 5 average rating, 150 reviews

Spectacular beach to bay views from this resort.

Sep 12 – 19

ﺩ.ﺇ720 per night
Guest favorite

Condo in Longboat Key

4.97 out of 5 average rating, 146 reviews

Sunset Studio on the Coast

Nov 30 – Dec 7

ﺩ.ﺇ1,161 per night

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