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Anna Maria Island to Bradenton Vacation Rentals

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Anna Maria Island and Bradenton Area Vacation Rentals By Owner

Welcome to the Anna Maria Island - Bradenton - Gulf Islands area, where pristine beaches and coastal charm invite you to unwind! Discover a variety of vacation rentals, from beachfront cottages to luxurious homes, and start your perfect beachside escape. From Anna Maria, Longboat Key and Bradenton areas start your search below!

Featured
Beachfront Condo on AMI
Last Minute!
From/Per night$156

Beachfront Condo on AMI

Holmes Beach Vacation Rentals
3/BR 2/BA SLEEPS 6
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Featured
Anna Maria Island Steps to Beach | Two Pools & Hot Tub | 3BR, 2BA & Balcony
Last Minute!
From/Per night$160

Anna Maria Island Steps to Beach | Two Pools & Hot Tub | 3BR, 2BA & Balcony

Bradenton Beach Vacation Rentals
3/BR 2/BA SLEEPS 7
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Featured
SeaDuction of Anna Maria Island
Last Minute!
From/Per night$130

SeaDuction of Anna Maria Island

Holmes Beach Vacation Rentals
2/BR 2/BA SLEEPS 6
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Family vacation on AMI w/pool 4BR, 2.5BA, 8 guests
From/Per night$300

Family vacation on AMI w/pool 4BR, 2.5BA, 8 guests

Holmes Beach Vacation Rentals
4/BR 2.5/BA SLEEPS 8
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River Strand is a Gated Resort Community located in Bradenton, FL - Monthly Rental
From/Per night$100

River Strand is a Gated Resort Community located in Bradenton, FL - Monthly Rental

Bradenton Vacation Rentals
2/BR 2/BA SLEEPS 2
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Seaside Inn
From/Per night$400

Seaside Inn

Anna Maria Vacation Rentals
3/BR 2/BA SLEEPS 6
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Americana AMI Lighthouse 3BR w/pool + rooftop deck
From/Per night$275

Americana AMI Lighthouse 3BR w/pool + rooftop deck

Holmes Beach Vacation Rentals
3/BR 2.5/BA SLEEPS 6
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CREEKSIDE PALMS: 4 mi. to ANNA MARIA ISLAND, Sleeps 14, Heated Pool, Fishing, Kayak and Beach Gear!
From/Per night$330

CREEKSIDE PALMS: 4 mi. to ANNA MARIA ISLAND, Sleeps 14, Heated Pool, Fishing, Kayak and Beach Gear!

Bradenton Vacation Rentals
4/BR 3/BA SLEEPS 14
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Anna Maria Island- less than 2 min walk to beach!
From/Per night$130

Anna Maria Island- less than 2 min walk to beach!

Bradenton Beach Vacation Rentals
2/BR 2/BA SLEEPS 6
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Sunkissed & Salty: Guest Favorite! Prime Island Location with Dreamy Amenities
From/Per night$1050

Sunkissed & Salty: Guest Favorite! Prime Island Location with Dreamy Amenities

Anna Maria Vacation Rentals
4/BR 4/BA SLEEPS 8
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Anna Maria Island -walk to the beach!
From/Per night$120

Anna Maria Island -walk to the beach!

Holmes Beach Vacation Rentals
2/BR 2/BA SLEEPS 6
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Nest on the Beach is magical!
From/Per night$1000

Nest on the Beach is magical!

Anna Maria Vacation Rentals
5/BR 5.5/BA SLEEPS 8
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Alecassandra Vacation Villas - From $300 Family Reunion Location, Villa 4 & 5, 4BR, 4BA, Sleeps 12
From/Per night$300

Alecassandra Vacation Villas - From $300 Family Reunion Location, Villa 4 & 5, 4BR, 4BA, Sleeps 12

Bradenton Beach Vacation Rentals
4/BR 4/BA SLEEPS 12
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Highlighted
Steps To The Beach, Private & Heated Pool, Renovated - Now Booking Summer/Fall!
From/Per night$300

Steps To The Beach, Private & Heated Pool, Renovated - Now Booking Summer/Fall!

Holmes Beach Vacation Rentals
3/BR 1/BA SLEEPS 6
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Buena Vista 1
From/Per night$1029

Buena Vista 1

Holmes Beach Vacation Rentals
4/BR 3.5/BA SLEEPS 8
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New! Waterfront Views w/Private Heated Pool/Spa & Luxury Resort Amenities Sleeps 16
From/Per night$500

New! Waterfront Views w/Private Heated Pool/Spa & Luxury Resort Amenities Sleeps 16

Anna Maria Vacation Rentals
6/BR 4/BA SLEEPS 16
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The GRAND ISLAND OASIS - LUXURY 8 BDRM PRIVATE HOME- ANNA MARIA ISLAND
From/Per night$799

The GRAND ISLAND OASIS - LUXURY 8 BDRM PRIVATE HOME- ANNA MARIA ISLAND

Bradenton Beach Vacation Rentals
8/BR 5/BA SLEEPS 18
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Beautiful Classy Gulf Coast Anna Maria Island, Private Pool, Close to Beach
From/Per night$225

Beautiful Classy Gulf Coast Anna Maria Island, Private Pool, Close to Beach

Holmes Beach Vacation Rentals
3/BR 2/BA SLEEPS 6
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The Peachy Beach House, Steps to an Anna Maria Beach
From/Per night$349

The Peachy Beach House, Steps to an Anna Maria Beach

Holmes Beach Vacation Rentals
2/BR 2/BA SLEEPS 5
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Highlighted
Sirenia By The Sea - Renovated - 5/5 Waterfront Dock Pool Hot Tub Putting Green - Steps to the Beach
From/Per night$500

Sirenia By The Sea - Renovated - 5/5 Waterfront Dock Pool Hot Tub Putting Green - Steps to the Beach

Anna Maria Vacation Rentals
5/BR 5/BA SLEEPS 12
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Backyard Bliss
From/Per night$249

Backyard Bliss

Holmes Beach Vacation Rentals
2/BR 2/BA SLEEPS 4
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PRIME LOCATION ON AMI ** DIRECTLY ON WHITE SUGAR SAND BEACH ** HEATED POOL
From/Per night$171

PRIME LOCATION ON AMI ** DIRECTLY ON WHITE SUGAR SAND BEACH ** HEATED POOL

Bradenton Beach Vacation Rentals
2/BR 2/BA SLEEPS 4
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Bayside Inn
From/Per night$800

Bayside Inn

Anna Maria Vacation Rentals
5/BR 5/BA SLEEPS 8
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Highlighted
Sirenia Cove - Htd Pool Hot Tub Waterfront Dock Ping Pong Outdoor Bar Backyard Beach Walk to Beaches
From/Per night$357

Sirenia Cove - Htd Pool Hot Tub Waterfront Dock Ping Pong Outdoor Bar Backyard Beach Walk to Beaches

Anna Maria Vacation Rentals
4/BR 3/BA SLEEPS 12
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Anna Maria Island to Cortez and Bradenton Rentals

Welcome to the Anna Maria Island - Bradenton Area, Florida - Your Epic Coastal Holiday!

Experience the enchanting allure of Anna Maria Island, Cortez, Longboat Key and Bradenton, where pristine beaches, historic charm, and endless outdoor adventures await. Nestled along Florida's stunning Gulf Coast, this idyllic region offers the perfect mix of relaxation and exploration. Whether you’re dreaming of a tranquil beachfront retreat, a vibrant coastal village, or an adventure-filled getaway, Anna Maria Island, Cortez, and Bradenton have it all. Explore our selection of vacation rentals and start planning your unforgettable escape to Florida’s Gulf Coast today!

When is High Season in the Anna Maria Island - Bradenton Florida area?

The high season for visiting the Anna Maria Island - Bradenton area is from December to April, when the weather is pleasantly warm and ideal for outdoor activities. During this time, visitors can enjoy vibrant local festivals like the Anna Maria Island Art League’s Winterfest and the Cortez Commercial Fishing Festival, which celebrate the area's rich cultural heritage and maritime history. High season also occurs in the peak summer months for locals looking to escape the heat of the mainland. The pristine beaches, bustling markets, and numerous water sports make this season perfect for a sun-soaked coastal getaway.

When is Low Season in the Anna Maria Island - Bradenton Florida area?

The low season in the Anna Maria Island - Bradenton area runs from August to December, offering a quieter and more relaxed atmosphere. During this time, visitors can enjoy uncrowded beaches, lower accommodation rates, and the chance to explore local attractions at a leisurely pace. October brings a special highlight with the Bayfest music and food festival, a local favorite that adds vibrant energy to the season, making it an ideal time to experience the area's charm without the peak season crowds.

What Type of Vacation Rental Accommodations are found in the Anna Maria - Bradenton area?

The Anna Maria Island - Bradenton area offers a diverse range of vacation rental accommodations to suit every traveler's needs. Visitors can find beachfront cottages, luxurious waterfront condos, and spacious family homes, many with private pools and direct beach access. For those seeking a more unique experience, there are charming bungalows, historic homes, and even eco-friendly rentals. Whether you're looking for a cozy retreat for two or a large property for a family gathering, the area has a variety of options that cater to different styles and budgets.

Longer Stays

In the Anna Maria Island - Bradenton area, you’ll find an array of monthly and seasonal vacation rental accommodations, especially in exclusive neighborhoods like Key Royale on Anna Maria Island and on the mainland in Harbour Isle, Bradenton, and Lakewood Ranch. Key Royale offers luxurious waterfront homes, many with private docks and easy access to the Gulf, perfect for extended stays. On the mainland, Harbour Isle features resort-style condos with stunning views and top-tier amenities, ideal for long-term rentals. Lakewood Ranch and other mainland resorts provide a mix of modern homes and condos, all within beautifully planned communities, making them ideal for snowbirds and those looking to immerse themselves in the Florida lifestyle for a month or more.

Is the Anna Maria Island - Bradenton area a Good Place to Visit?

Yes, the Anna Maria Gulf Island - Bradenton area is a fantastic place to visit, offering a perfect blend of natural beauty, rich history, and laid-back charm. Visitors can enjoy pristine, white-sand beaches, crystal-clear waters, and abundant outdoor activities like fishing, kayaking, and cycling. The area is also home to unique shops, art galleries, and local dining experiences that capture the essence of Florida’s Gulf Coast. With its welcoming atmosphere and diverse attractions, it’s an ideal destination for families, couples, and solo travelers alike.

What Cities are nearby Anna Maria Island - Bradenton Fl?

Nearby cities to Anna Maria Island and Bradenton, FL, include Sarasota, Palmetto, Ellenton, Cortez, and Longboat Key.

  • Sarasota, just a short drive south, offers a vibrant arts scene, upscale shopping, and beautiful gardens.
  • Palmetto, located across the Manatee River from Bradenton, is known for its historic downtown and scenic riverfront parks.
  • Ellenton, to the northeast, is famous for its outlet mall and relaxed, small-town atmosphere.
  • Cortez, a historic fishing village just west of Bradenton, provides a charming glimpse into the region's maritime heritage and offers fresh seafood and waterfront dining.
  • Longboat Key, situated to the south, is renowned for its luxurious resorts, golf courses, and stunning Gulf Coast beaches.

These neighboring cities and towns enhance the appeal of the Anna Maria Island - Bradenton area, offering a range of experiences and attractions.

What Else is Good for a Visitor to Know about the Anna Maria Island - Bradenton area?

For visitors to the Anna Maria Island - Bradenton area, here are some helpful insights and tips:

Beaches: Anna Maria Island is renowned for its pristine, white-sand beaches and clear turquoise waters. Popular spots include Holmes Beach, Bradenton Beach, and Bean Point, each offering a serene atmosphere and great for sunbathing, swimming, and shell collecting.

Local Dining: The area offers a variety of dining options from casual seafood shacks to fine dining. Popular spots include The Sandbar Restaurant on Anna Maria Island, known for its beachfront views, and Joe’s Eats and Sweets for delicious ice cream and desserts.

Outdoor Activities: Visitors can enjoy a range of outdoor activities such as kayaking, paddleboarding, and fishing. Explore the natural beauty of the local mangroves and waterways with a guided tour or rent equipment locally.

Cultural and Historical Sites: The Manatee Village Historical Park in Bradenton provides a glimpse into the area’s history with preserved historic buildings and exhibits. The Anna Maria Island Historical Society Museum also offers insights into the island’s past.

Shopping: The area has charming boutiques and shops. In Anna Maria, visit Pine Avenue for unique shops and local artisan products, while the Bradenton area offers larger shopping centers like the Ellenton Premium Outlets.

Events and Festivals: The Anna Maria Island area hosts various events throughout the year. The Anna Maria Island Concert Series and the Bayfest Music and Food Festival in October are highlights. The annual ArtSlam event in Bradenton is another favorite, celebrating local arts and culture.

Transportation: The island has limited parking, so consider using the free Island Trolley service to get around Anna Maria Island. Bicycles and golf carts are also popular for exploring the area.

Nature and Wildlife: Visit the Robinson Preserve and the Florida Maritime Museum in Cortez to experience local wildlife and learn about the region’s maritime history. Birdwatching and nature trails offer opportunities to see native species and enjoy the natural beauty of the area.

These aspects make the Anna Maria Island - Bradenton area a diverse destination with plenty to offer, whether you’re seeking relaxation, adventure, or cultural experiences.

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