Anna Maria Island vacation rentals

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Top-rated vacation rentals in Anna Maria Island

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Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 236 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, kayaking, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

Nov 30 – Dec 7

ﺩ.ﺇ481 per night

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 19 – 26

ﺩ.ﺇ1,024 per night

Guest favorite

Condo in Holmes Beach

4.98 out of 5 average rating, 108 reviews

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean and comfortable, my unit at Sandy Pointe II is in a secluded setting just a few minutes walk to a less crowded, quieter section of beautiful AMI beach. From here the Island is at your fingertips! Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! A FREE Island trolly stop is steps from our entrance with grocery, drug store, beach shops and so much more just across E Bay Dr.

Dec 7 – 14

ﺩ.ﺇ692 per night

Guest favorite

Guest suite in Sarasota

4.98 out of 5 average rating, 103 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!

Nov 8 – 15

ﺩ.ﺇ422 per night

Guest favorite

Condo in Redington Beach

4.97 out of 5 average rating, 457 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 3 – 10

ﺩ.ﺇ396 per night

Guest favorite

Cottage in Bradenton

4.94 out of 5 average rating, 299 reviews

Historic Private King Bed Suite-Near Beach-D’Town.

Your relaxing vacation is here! Private Cottage with a huge deck. Wonderfully furnished with plush linens, beach towels/chairs. A great nights sleep with a king-size bed and pull-out couch which serves as 2nd bed. Private kitchen and bath. TV and fast WIFI. We are located in a historic and quiet neighborhood in DT Bradenton. There are 3 villas on our large corner property. Off street parking. Quiet times are between 10PM until 7:30AM. Please respect others. Walk to many great restaurants!

Jun 26 – Jul 3

ﺩ.ﺇ500 per night

Guest favorite

Apartment in Anna Maria

4.98 out of 5 average rating, 103 reviews

Beach Don't Kill My Vibe by Beach Boutique Rentals

*Features include* * Brand new vacation rental directly on Pine Ave! * King bedroom with TV * Queen bedroom with TV * Modern bathroom with walk in shower * Kitchenette with Full size refrigerator * Private deck with table and umbrella * Private back yard with putting green and outdoor seating * Trolley stop across the street * Steps to the beach! * Walkable to all shops and restaurants on Pine Avenue * Beach chairs, umbrella and cart * Off-street parking for one vehicle

Mar 22 – 29

ﺩ.ﺇ2,419 per night

Guest favorite

Guest suite in Bradenton

4.93 out of 5 average rating, 135 reviews

Live and Enjoy Arlet’s Dream

Enjoy the simplicity of this quiet and central accommodation from which you can easily access exquisite restaurants, fast food place, airports, shopping malls, cultural and recreational centers as well as the beautiful beaches that characterize this city .Feel the warmth and enjoy the great sunset of Ana Maria Island and Coquina beach.Walk along the white and fine sand of a set of beaches that will be within your reach due to the central and privileged location of this accommodation.

Nov 8 – 15

ﺩ.ﺇ439 per night

Guest favorite

Bungalow in Anna Maria

4.88 out of 5 average rating, 120 reviews

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

Oct 4 – 11

ﺩ.ﺇ1,080 per night

Guest favorite

Condo in Holmes Beach

4.96 out of 5 average rating, 116 reviews

Beautiful beachfront condo for perfect vacation

Beautiful, cozy, elegantly furnished, spacious (1350 sqf with a large terrace), beachfront, 2 bedroom - 2 bathroom condominium, in the best managed, boutique-style gulf front residential complex on Anna Maria Island in Florida for an ideal vacation. Heated pool and hot tub, 2 tennis courts, 2 elevators, top floor unit, high speed internet, washer/dryer in unit, beach chairs, close to supermarket (Publix) and restaurants, free island trolley, rich cultural life.

Jul 20 – 27

ﺩ.ﺇ939 per night

Guest favorite

Guest suite in Bradenton

4.97 out of 5 average rating, 120 reviews

Florida West Coast Get-Away

Enjoy Florida's beautiful West Coast in your own cozy, private apartment . One bedroom, living room, kitchenette with breakfast bar, attached bath with shower. Central air and heat. Free wi-fi. Private drive and gated entrance. Everything you will need is here just waiting for your arrival. You'll find this a beautiful place near everything you will need to enjoy your Florida vacation. Not available for guests with infants.

Aug 14 – 21

ﺩ.ﺇ279 per night

Guest favorite

Guesthouse in Bradenton

4.82 out of 5 average rating, 380 reviews

Luxury Suite near water, IMG anna Maria Island

This condo is attached to my home but is totally independant with private access. The condo is upstairs and accessible by a spiral staircase ( avoid large suitcase, may be challenging for some people) A large bedroom with a queen bed, an equiped kichen ( combined microwave/ oven), a bathroom ( large shower) and a living room with high ceiling. We follow cleaning recommendations. You can arrive anytime after check in time.

Sep 17 – 24

ﺩ.ﺇ336 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Anna Maria Island vacation rentals

Free parking on premises

Other great vacation rentals in Anna Maria Island

Guest favorite

Home in Bradenton Beach

4.97 out of 5 average rating, 152 reviews

Paradise! Steps2 Private Beach & Tropical Yard!

Dec 7 – 14

ﺩ.ﺇ1,897 per night

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

Nov 6 – 13

ﺩ.ﺇ1,952 per night

Guest favorite

Home in Bradenton

4.94 out of 5 average rating, 152 reviews

Peaceful Braden River Oasis: Cottage

Aug 22 – 29

ﺩ.ﺇ369 per night

Guest favorite

Home in Bradenton

4.96 out of 5 average rating, 198 reviews

Home near Anna Maria Beach - Hot Tub + Fire Pit

Aug 10 – 17

ﺩ.ﺇ703 per night

Guest favorite

Home in Bradenton Beach

4.89 out of 5 average rating, 237 reviews

Ohana Beachside 2 BR Bungalow - 150 ft from beach

Dec 15 – 22

ﺩ.ﺇ803 per night

Guest favorite

Home in Bradenton

5.0 out of 5 average rating, 10 reviews

The "Love shack" Bungalow

Jul 20 – 27

ﺩ.ﺇ420 per night

Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 12 reviews

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

Nov 1 – 8

ﺩ.ﺇ1,648 per night

Guest favorite

Home in Holmes Beach

4.91 out of 5 average rating, 23 reviews

Backyard Bliss Anna Maria Island

Mar 6 – 13

ﺩ.ﺇ1,807 per night

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Anna Maria Island villa rentals

Superhost

Villa in Redington Shores

4.88 out of 5 average rating, 110 reviews

Peaceful 1 min to sand W/D Priv patio

Jun 25 – Jul 2

ﺩ.ﺇ724 per night

Guest favorite

Villa in Siesta Key

4.9 out of 5 average rating, 136 reviews

Mermaid Villa Ocean Front!

Aug 31 – Sep 7

ﺩ.ﺇ2,877 per night

Superhost

Villa in Nokomis

4.92 out of 5 average rating, 142 reviews

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

Dec 18 – 25

ﺩ.ﺇ655 per night

Guest favorite

Villa in Sarasota

4.96 out of 5 average rating, 133 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

Jan 5 – 12

ﺩ.ﺇ1,058 per night

Guest favorite

Villa in Clearwater

4.92 out of 5 average rating, 212 reviews

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

May 7 – 14

ﺩ.ﺇ673 per night

Guest favorite

Villa in Safety Harbor

5.0 out of 5 average rating, 110 reviews

Villa Key West "Villas by Christine"

May 24 – 31

ﺩ.ﺇ699 per night

Superhost

Villa in St. Petersburg

4.83 out of 5 average rating, 109 reviews

St. Pete Beach Oceanfront Villa Saltwater Pool

Jun 9 – 16

ﺩ.ﺇ1,207 per night

Guest favorite

Villa in Sarasota

4.84 out of 5 average rating, 128 reviews

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

May 2 – 9

ﺩ.ﺇ605 per night

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Anna Maria Island condo rentals

Guest favorite

Condo in Holmes Beach

4.99 out of 5 average rating, 124 reviews

Beach Escape - Make Memories on Anna Maria Island!

Oct 24 – 31

ﺩ.ﺇ970 per night

Guest favorite

Condo in Indian Rocks Beach

4.79 out of 5 average rating, 224 reviews

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

Aug 16 – 23

ﺩ.ﺇ434 per night

Guest favorite

Condo in Longboat Key

4.93 out of 5 average rating, 144 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Oct 26 – Nov 2

ﺩ.ﺇ1,129 per night

Guest favorite

Condo in Madeira Beach

4.95 out of 5 average rating, 233 reviews

Steps Away 1st Floor-Bikes/Beach Access/ WI-FI

Aug 5 – 12

ﺩ.ﺇ363 per night

Guest favorite

Condo in Bradenton Beach

4.91 out of 5 average rating, 127 reviews

Beachfront condo in paradise

Dec 28 – Jan 4

ﺩ.ﺇ1,777 per night

Guest favorite

Condo in St. Pete Beach

4.91 out of 5 average rating, 207 reviews

Sunset Beach Condo in Treasure Island

Dec 11 – 18

ﺩ.ﺇ439 per night

Guest favorite

Condo in Redington Beach

4.94 out of 5 average rating, 356 reviews

Beach Condo, Heated Pool, 2 Minute Walk to Ocean

Dec 13 – 20

ﺩ.ﺇ370 per night

Guest favorite

Condo in St. Pete Beach

4.92 out of 5 average rating, 118 reviews

Beachside studio only steps to the beach

Aug 9 – 16

ﺩ.ﺇ482 per night

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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.

Anna Maria Island vacation rentals

Top-rated vacation rentals in Anna Maria Island

Vacation rentals for every style

Houses

Villas

Cottages

Popular amenities for Anna Maria Island vacation rentals

Other great vacation rentals in Anna Maria Island

Home in Bradenton Beach

Home in Anna Maria

Home in Bradenton

Home in Bradenton

Home in Bradenton Beach

Home in Bradenton

Home in Anna Maria

Home in Holmes Beach

Anna Maria Island villa rentals

Villa in Redington Shores

Villa in Siesta Key

Villa in Nokomis

Villa in Sarasota

Villa in Clearwater

Villa in Safety Harbor

Villa in St. Petersburg

Villa in Sarasota

Anna Maria Island condo rentals

Condo in Holmes Beach

Condo in Indian Rocks Beach

Condo in Longboat Key

Condo in Madeira Beach

Condo in Bradenton Beach

Condo in St. Pete Beach

Condo in Redington Beach

Condo in St. Pete Beach

Your guide to Anna Maria Island

Introduction

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

Top things to do in Anna Maria Island

Coquina Beach

Coquina Baywalk

Bean Point Beach

Frequently Asked Questions

How is the weather in Anna Maria Island?

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

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

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

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

What are some hiking trails in Anna Maria Island?

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

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

Destinations to explore