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.
Home in Holmes Beach
4.96 out of 5 average rating, 157 reviewsSea 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
Guest suite in Sarasota
4.98 out of 5 average rating, 100 reviewsMid-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
Condo in Redington Beach
4.97 out of 5 average rating, 455 reviewsAmazingBeachCondo/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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Anna Maria Island vacation rentals
Anna Maria Island house rentals
Home in Anna Maria
4.93 out of 5 average rating, 152 reviewsPrivate 30' Pool and Boat Dock - Rated best on AMI
Oct 23 – 30
Home in Bradenton Beach
4.97 out of 5 average rating, 149 reviewsParadise! Steps2 Private Beach & Tropical Yard!
Dec 5 – 12
Home in Holmes Beach
4.99 out of 5 average rating, 153 reviewsCaptain's Quarters at Spinnakers Vacation Cottages
Jul 13 – 20
Home in Bradenton
4.91 out of 5 average rating, 251 reviewsPalm Retreat Gold: Luxury Edition of #1 Rental
Dec 5 – 12
Home in Bradenton
4.94 out of 5 average rating, 150 reviewsPeaceful Braden River Oasis: Cottage
Aug 30 – Sep 6
Home in Bradenton Beach
4.89 out of 5 average rating, 236 reviewsOhana Beachside 2 BR Bungalow - 150 ft from beach
Jan 4 – 11
Home in Holmes Beach
4.97 out of 5 average rating, 123 reviewsTwin Palms: Big House Steps to Beach w/Lush Pool
Aug 25 – Sep 1
Home in Holmes Beach
4.91 out of 5 average rating, 23 reviewsEnjoy AMI sunsets | Chic home w/ Saltwater pool!
Dec 6 – 13
Home in Anna Maria
5.0 out of 5 average rating, 11 reviewsLamantin- 2 bed/2bath North End, beach 2 min walk
Aug 29 – Sep 5
Home in Holmes Beach
5.0 out of 5 average rating, 46 reviewsPrivate Luxurious Ground Level Home
Sep 16 – 23
Home in Anna Maria
4.88 out of 5 average rating, 34 reviewsBean Pt. Bungalow - Half duplex w/private pool
Dec 5 – 12
Home in Anna Maria
5.0 out of 5 average rating, 28 reviewsami skyview
Sep 25 – Oct 2
Anna Maria Island villa rentals
Villa in Nokomis
4.91 out of 5 average rating, 138 reviewsAPR SALE! Sarasota Family BEACH Villa 2KING BR/2BA
Jun 16 – 23
Villa in Siesta Key
4.9 out of 5 average rating, 133 reviewsMermaid Villa Ocean Front!
Sep 21 – 28
Villa in Sarasota
4.96 out of 5 average rating, 130 reviewsNewly Renovated- 150 Yards to Beach & Restaurants!
Jan 10 – 17
Villa in Sarasota
4.89 out of 5 average rating, 181 reviewsEntire Standalone Villa,1.2k sf,1 block Lido Beach
Sep 13 – 20
Villa in Redington Shores
4.9 out of 5 average rating, 121 reviewsOutstanding location 1 min to sand W/D Priv patio
Oct 8 – 15
Villa in Bradenton
4.83 out of 5 average rating, 133 reviewsElegant private home 3Bdr/3bth
Jun 29 – Jul 6
Villa in Safety Harbor
5.0 out of 5 average rating, 109 reviewsVilla Key West "Villas by Christine"
Jun 1 – 8
Villa in Clearwater
4.91 out of 5 average rating, 210 reviewsV3- 1 BR, waterfront villa, 2 min walk 2 beach
Dec 14 – 21
Villa in St. Petersburg
4.84 out of 5 average rating, 106 reviewsSt. Pete Beach Oceanfront Villa Saltwater Pool
Dec 3 – 10
Villa in Holmes Beach
5.0 out of 5 average rating, 9 reviewsWaterfront in Paradise
Jul 9 – 16
Villa in Holmes Beach
4.98 out of 5 average rating, 50 reviewsCalico - Family Oasis - Steps from the Sand
Aug 17 – 24
Villa in HOLMES BEACH
4.7 out of 5 average rating, 23 reviewsLocation! Steps from Manatee Beach 2BR
Jul 15 – 22
Anna Maria Island condo rentals
Condo in Bradenton Beach
4.9 out of 5 average rating, 123 reviewsBeachfront condo in paradise
Dec 6 – 13
Condo in Holmes Beach
4.96 out of 5 average rating, 116 reviewsBeautiful beachfront condo for perfect vacation
Jul 3 – 10
Condo in Holmes Beach
4.99 out of 5 average rating, 121 reviewsBeach Escape - Make Memories on Anna Maria Island!
Oct 24 – 31
Condo in Redington Beach
4.92 out of 5 average rating, 106 reviewsRoyal Orleans and Redington Beach ( Studio 203 )
Dec 8 – 15
Condo in Holmes Beach
4.92 out of 5 average rating, 156 reviewsAnna Maria Beach Place...footsteps to the sands
Nov 26 – Dec 3
Condo in Longboat Key
4.93 out of 5 average rating, 143 reviewsBeachfront Resort, Ocean View, Pool, Tennis, Gym
Nov 21 – 28
Condo in Indian Shores
4.96 out of 5 average rating, 142 reviews1 BR direct beachfront! Now available May 22-27!
Oct 30 – Nov 6
Condo in St. Pete Beach
4.92 out of 5 average rating, 200 reviewsSunset Beach Condo in Treasure Island
Sep 13 – 20
Condo in Siesta Key
4.9 out of 5 average rating, 149 reviewsCozy Siesta Key studio 5 minute walk to Village
Nov 12 – 19
Condo in Indian Rocks Beach
4.79 out of 5 average rating, 223 reviewsWaterfront Condo w/ Boat dock, 2 min walk to beach
Mar 20 – 27
Condo in Treasure Island
4.99 out of 5 average rating, 150 reviewsSpectacular beach to bay views from this resort.
Sep 12 – 19
Condo in Longboat Key
4.97 out of 5 average rating, 146 reviewsSunset Studio on the Coast
Nov 30 – Dec 7
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
- St Petersburg Vacation rentals
- Sarasota Vacation rentals
- Tampa Vacation rentals
- Key West Vacation rentals
- Naples Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- West Palm Beach Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Waterfront rentals Anna Maria Island
- House rentals Anna Maria Island
- Apartment rentals Anna Maria Island
- Rentals with pools Anna Maria Island
- Cottage rentals Anna Maria Island
- Rentals with outdoor seating Anna Maria Island
- Beach house rentals Anna Maria Island
- Rentals with an EV charger Anna Maria Island
- Condo rentals Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Townhouse rentals Anna Maria Island
- Villa rentals Anna Maria Island
- Monthly Rentals Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Rentals with a kayak Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Rentals with beach access Anna Maria Island
- Kid-friendly rentals Anna Maria Island
- Fitness-friendly rentals Anna Maria Island
- Rentals with lake access Anna Maria Island
- Rentals with a patio Anna Maria Island
- Rentals with a washer and dryer Anna Maria Island
- Rentals with a fire pit Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Wheelchair accessible rentals Anna Maria Island
- Beach condo rentals Anna Maria Island
- Beachfront rentals Anna Maria Island
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom