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 Holmes Beach

4.99 out of 5 average rating, 125 reviews

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.

Oct 17 – 24

G$54,849 GYD 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.

May 11 – 18

G$39,993 GYD 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.

Oct 28 – Nov 4

G$21,979 GYD per night

Guest favorite

Tiny home in Bradenton

4.95 out of 5 average rating, 307 reviews

Tiny Carriage House-Pool, Riverwalk, Downtown

In the historic district of Bradenton's riverside downtown the 2nd story 1898 Carriage House Retreat is an intimate 1room studio for a romantic weekend, a friends' getaway or business travelers. Fully renovated with every modern amenity, yet preserving its antiquity, it nestles behind our 1898 Queen Anne Victorian where we live. Where the horse and buggy would have been kept, the Carriage House sits with it's own private driveway & within steps of downtown's eateries, pubs, shopping & more!

Aug 13 – 20

G$32,903 GYD per night

Guest favorite

Apartment in Treasure Island

4.92 out of 5 average rating, 162 reviews

Treasure Island Beach Apartment #1

Location! Situated on Gulf Blvd, directly across from the 123rd Street beach access in Treasure Island. Walk to John's Pass for restaurants, shopping, bars and music, boat trips and fishing. Two bedroom, one bath private apartment, with all the amenities you need for a great beach vacation - beach chairs, umbrella, cooler, barbecue, bicycles. Master bedroom has queen bed, and Roku tv. Smaller bedroom has twin trundle bed, perfect for the kids. Full kitchen. Off street parking for one car.

Jan 2 – 9

G$26,486 GYD 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.

Dec 15 – 22

G$66,775 GYD 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

G$53,309 GYD per night

Guest favorite

Guesthouse in Bradenton Beach

5.0 out of 5 average rating, 119 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Sep 1 – 8

G$44,032 GYD 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.

Jun 21 – 28

G$15,850 GYD per night

Guest favorite

Guest suite in Bradenton

5.0 out of 5 average rating, 186 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.

Jul 15 – 22

G$24,669 GYD per night

Guest favorite

Cottage in Treasure Island

5.0 out of 5 average rating, 176 reviews

Island Time Stay: Sunset

Fantastic find! This one bedroom, one bathroom cottage is located on Gulf Blvd in Treasure Island, Florida. It is located less than 300 steps from the beautiful sand of Treasure Island Beach and 5 blocks from the world famous boardwalk, shopping and restaurants of John’s Pass in Madeira Beach. Come soak up the sun and sand in this relaxing retreat. The Tampa Bay area is wonderful for year round golf...bring your clubs!

Sep 8 – 15

G$32,369 GYD per night

Guest favorite

Cottage in Anna Maria

4.98 out of 5 average rating, 207 reviews

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Dec 4 – 11

G$74,106 GYD 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 Sarasota

4.96 out of 5 average rating, 128 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Jul 23 – 30

G$22,345 GYD per night

Guest favorite

Home in Holmes Beach

4.95 out of 5 average rating, 158 reviews

Sea AMI

Jan 6 – 13

G$79,844 GYD per night

Guest favorite

Home in Bradenton

4.94 out of 5 average rating, 152 reviews

Peaceful Braden River Oasis: Cottage

Aug 24 – 31

G$20,743 GYD 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

G$110,816 GYD per night

Guest favorite

Home in Bradenton Beach

4.97 out of 5 average rating, 153 reviews

Paradise! Steps2 Private Beach & Tropical Yard!

Apr 12 – 19

G$143,375 GYD per night

Guest favorite

Home in Holmes Beach

4.89 out of 5 average rating, 9 reviews

Anna Maria Island 2-bed/2 bath (side A of duplex)

Nov 12 – 19

G$34,108 GYD per night

Guest favorite

Home in Bradenton

5.0 out of 5 average rating, 10 reviews

The "Love shack" Bungalow

Jul 29 – Aug 5

G$23,240 GYD per night

Guest favorite

Home in Holmes Beach

4.92 out of 5 average rating, 24 reviews

Backyard Bliss Anna Maria Island

Mar 6 – 13

G$103,282 GYD per night

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Anna Maria Island villa rentals

Superhost

Villa in Redington Shores

4.88 out of 5 average rating, 111 reviews

Peaceful 1 min to sand W/D Priv patio

Jun 25 – Jul 2

G$41,077 GYD per night

Guest favorite

Villa in Siesta Key

4.91 out of 5 average rating, 137 reviews

Mermaid Villa Ocean Front!

Sep 3 – 10

G$163,346 GYD per night

Guest favorite

Villa in Sarasota

4.96 out of 5 average rating, 133 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

Jan 11 – 18

G$60,068 GYD per night

Guest favorite

Villa in Safety Harbor

5.0 out of 5 average rating, 110 reviews

Villa Key West "Villas by Christine"

Aug 21 – 28

G$39,698 GYD per night

Guest favorite

Villa in Clearwater

4.92 out of 5 average rating, 213 reviews

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

Sep 21 – 28

G$38,492 GYD per night

Guest favorite

Villa in Tampa

4.92 out of 5 average rating, 130 reviews

Villa Perdomo Family

Sep 29 – Oct 6

G$36,403 GYD per night

Guest favorite

Villa in Bradenton

4.83 out of 5 average rating, 136 reviews

Elegant private home 3Bdr/3bth

Apr 15 – 22

G$56,878 GYD per night

Guest favorite

Villa in Tampa

4.91 out of 5 average rating, 169 reviews

Busch Gardens, Moffitt, USF Charming Villa

Sep 4 – 11

G$29,371 GYD per night

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Anna Maria Island condo rentals

Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 143 reviews

1 BR direct beachfront! Now available Aug.18-24.

Dec 10 – 17

G$30,545 GYD 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

Jul 30 – Aug 6

G$20,368 GYD per night

Guest favorite

Condo in St. Pete Beach

4.91 out of 5 average rating, 208 reviews

Sunset Beach Condo in Treasure Island

Dec 4 – 11

G$24,340 GYD per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 236 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Apr 8 – 15

G$28,501 GYD per night

Guest favorite

Condo in Treasure Island

4.97 out of 5 average rating, 119 reviews

Funshine Pointe Capri - Pool on the Intercoastal!

Sep 24 – Oct 1

G$26,490 GYD per night

Guest favorite

Condo in Madeira Beach

4.9 out of 5 average rating, 137 reviews

Experience the charm of Gulf Gardens. The Pelican.

Oct 8 – 15

G$25,016 GYD per night

Guest favorite

Condo in Bradenton Beach

4.91 out of 5 average rating, 129 reviews

Beachfront condo in paradise

Nov 13 – 20

G$67,915 GYD per night

Guest favorite

Condo in St. Petersburg

4.96 out of 5 average rating, 142 reviews

Sea La Vie- Studio by the bay!

Dec 11 – 18

G$26,975 GYD 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 Sarasota

Home in Holmes Beach

Home in Bradenton

Home in Anna Maria

Home in Bradenton Beach

Home in Holmes Beach

Home in Bradenton

Home in Holmes Beach

Anna Maria Island villa rentals

Villa in Redington Shores

Villa in Siesta Key

Villa in Sarasota

Villa in Safety Harbor

Villa in Clearwater

Villa in Tampa

Villa in Bradenton

Villa in Tampa

Anna Maria Island condo rentals

Condo in Indian Shores

Condo in Redington Beach

Condo in St. Pete Beach

Condo in Tierra Verde

Condo in Treasure Island

Condo in Madeira Beach

Condo in Bradenton Beach

Condo in St. Petersburg

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