Anna Maria Vacations

Anna Maria Vacations Anna Maria Vacations provides you with the perfect beach house or condo rentals from one-bedroom condos to nine-bedroom luxury homes and villas.

Anna Maria vacation rentals are the perfect getaway on Florida’s beautiful, serene Gulf. We are truly a unique rental company specializing in only the finest Anna Maria Island Vacation Rentals. Our hand-selected properties provide our guests the upscale vacation experience they desire. We have luxury Gulf beachfront homes and beach condos, bay waterfront homes, and many exquisite inland homes just

a few minutes' stroll to the beach. Whether you are looking to stay in Holmes Beach, Bradenton Beach, or the City of Anna Maria, our goal is simple – to always deliver the best vacation rental experience possible for our guests. Want to find out more about our wonderful Island before you visit? Then keep in touch and be informed! Simply check out our Anna Maria Island Travel blog for some great and insightful pieces.

Which Anna Maria Island neighborhood fits your vacation style?From peaceful mornings by the beach to walkable dining and...
08/07/2026

Which Anna Maria Island neighborhood fits your vacation style?

From peaceful mornings by the beach to walkable dining and island adventures, each part of Anna Maria Island offers something a little different.

Anna Maria – Charming, laid-back, and known for its quiet streets, local boutiques, and beautiful beaches.

Holmes Beach – The heart of the island, with easy access to beaches, restaurants, shopping, and everyday conveniences.

Bradenton Beach – Home to Historic Bridge Street, waterfront dining, local shops, and plenty of ways to enjoy the island.

No matter which neighborhood feels like the perfect fit, you'll find a vacation home that's just right for your getaway.

Which neighborhood would you choose for your next island escape? Tell us in the comments!

Browse vacation rentals across Anna Maria Island and start planning your stay: https://hubs.ly/Q04sk1Zy0

🌴Beach in four minutes or your own private pool?At Crab Shack, you don’t have to choose.Just two blocks from Manatee Bea...
08/05/2026

🌴Beach in four minutes or your own private pool?

At Crab Shack, you don’t have to choose.

Just two blocks from Manatee Beach, this cozy Holmes Beach retreat puts sunny beach days, poolside afternoons, and local favorites near Holmes Beach Towne Center all within easy reach. It’s an inviting option for families, couples, or small groups looking for a laid-back Anna Maria Island getaway.

Highlights:
🏡 2 Bedrooms | 2.5 Bathrooms
🛏️ 1 King + Twin-over-Queen bunk with Twin trundle
🏊 Private heated pool
🏖️ 4-minute walk to Manatee Beach
🪑 Beach chairs + beach cart included
🔥 Outdoor patio + grill
🧺 Washer + dryer
📍 Near Holmes Beach Towne Center
🚗 2 parking spaces
🌴 7-night minimum stay

Ready to make Crab Shack your home base for a week on Anna Maria Island?

Book your stay: https://tinyurl.com/ykcurhch

Sunsets hit different here. 🌅Imagine ending your day with your toes in the sand, your favorite island drink in hand, and...
08/04/2026

Sunsets hit different here. 🌅

Imagine ending your day with your toes in the sand, your favorite island drink in hand, and the Gulf Coast painted in shades of gold and pink. No rush. No packed schedule. Just the kind of evening you'll wish you could relive again and again.

The best part? This doesn't have to stay on your vision board. Your Anna Maria Island getaway is closer than you think.

Book your stay with Anna Maria Vacations and start counting down to sunsets that feel just like this. 🌴✨

📍Your island escape is waiting. Tap the link in our bio to find the perfect vacation home.

☀️ A laid-back island escape is waiting at Palm Breeze.Just a short walk from the sugar-white sands of Holmes Beach, thi...
08/04/2026

☀️ A laid-back island escape is waiting at Palm Breeze.

Just a short walk from the sugar-white sands of Holmes Beach, this inviting vacation home makes it easy to spend your days by the water and your evenings unwinding with family. Whether you're planning beach adventures, friendly game nights, or exploring the local shops and restaurants nearby, Palm Breeze puts it all within easy reach.

Highlights:
🏖️ Short walk to Holmes Beach
🛏️ 3 Bedrooms | 2 Bathrooms (Sleeps 6)
👑 2 King Beds + 2 Twin Beds
🏊 Community Pool
🏓 Game room with ping pong, foosball & co****le
🪑 Beach chairs provided
🧺 Washer & dryer
📍 Near Holmes Beach Towne Center, restaurants & shopping
🚗 Parking for 3 vehicles

Ready for your next island getaway? Book your stay at Palm Breeze - https://tinyurl.com/3zkfrmd9

Nothing says "vacation memories" quite like finding a place you can't wait to return to. 💙"We stayed at The Beach Front ...
07/31/2026

Nothing says "vacation memories" quite like finding a place you can't wait to return to. 💙

"We stayed at The Beach Front on Gulf Drive and it’s been our favorite place we’ve ever stayed on vacation. The location was perfect and the view from the living room was phenomenal. You could easily watch the sunset or sunrise straight through the glass doors, or from the covered porch. We’d love to stay here again!!" — Heather Wallace

From breathtaking Gulf views to unforgettable sunrises and sunsets, we're so grateful to hear The Beach Front became part of Heather's favorite vacation memories.

Thank you for sharing your experience - we can't wait to welcome you back to Anna Maria Island! 🌴

Explore The Beach Front: https://tinyurl.com/3vzr63cd

North End or Holmes Beach? 🌊Every corner of Anna Maria Island has its own charm - it just depends on the kind of getaway...
07/29/2026

North End or Holmes Beach? 🌊

Every corner of Anna Maria Island has its own charm - it just depends on the kind of getaway you're looking for.

🏡 Beach Paradise is perfect for those who love the peaceful atmosphere of the North End. Just four houses from Bean Point Beach, it's an ideal retreat for relaxing beach days, quiet morning walks, and soaking in the island's laid-back charm.

🌴 Tiki Sunshine puts you in the heart of Holmes Beach, where you're just a short walk from the beach, local restaurants, parks, shopping, and the free island trolley - making it easy to explore everything the island has to offer.

Which side of Anna Maria Island is more your style? Tell us in the comments! ⬇️

Explore these homes:

🏡 Beach Paradise
https://tinyurl.com/3e899tah

🌴 Tiki Sunshine
https://tinyurl.com/yued9mjj

Your vacation doesn't stop at the front door. View of the Gulf is designed for making the most of every moment outdoors ...
07/27/2026

Your vacation doesn't stop at the front door. View of the Gulf is designed for making the most of every moment outdoors - from sunny afternoons by the pool to evenings spent under the stars.

Relax in the private heated pool and spa, gather around the outdoor tiki bar, challenge your crew to a game of shuffleboard, or head up to the rooftop deck to take in the island breeze. And when you're ready for the beach, Holmes Beach is just a 2-minute walk away.

Highlights:

🛏️ 7 Bedrooms | 🛁 4.5 Bathrooms
🏊 Private heated pool & spa
🌅 Rooftop deck
🍹 Outdoor tiki bar & hammock
🔥 Gas grill & outdoor shower
🎯 Shuffleboard
🏖️ 2-minute walk to Holmes Beach
🚋 Near the free island trolley, boutiques, cafés & restaurants

Ready to enjoy the best of outdoor island living?
Explore View of the Gulf and book your stay: https://tinyurl.com/4wpe4ysr

Balcony Views or Backyard Gatherings? ☀️Whether your perfect vacation starts with panoramic water views or unforgettable...
07/23/2026

Balcony Views or Backyard Gatherings? ☀️

Whether your perfect vacation starts with panoramic water views or unforgettable moments around the pool, there's a stay on Anna Maria Island that's just your style.

🌅 The Blue Horizon offers breathtaking Gulf-front views, rooftop and beachfront decks, and front-row seats to every sunset.

🌴 Sugar Plum Beach is made for gathering, featuring a private pool, outdoor dining, and a spacious pergola perfect for family meals and evening barbecues.

Which would you choose for your next island escape? Tell us in the comments! ⬇️

Explore these homes:

🏡 The Blue Horizon - https://tinyurl.com/5b5ru8rx
🏡 Sugar Plum Beach - https://tinyurl.com/n5j8kns2

Looking for the perfect blend of peaceful bayfront living and easy beach access?Breakaway offers the best of both worlds...
07/20/2026

Looking for the perfect blend of peaceful bayfront living and easy beach access?

Breakaway offers the best of both worlds. Spend your mornings overlooking Tampa Bay, relax by your private heated pool, and take a short stroll to the sugar-white sands of Bean Point Beach.

With room for families, couples, and small groups, this island retreat puts you close to Pine Avenue's local shops, waterfront dining, and everything that makes Anna Maria Island unforgettable.

Highlights:
🛏️ 4 Bedrooms | 🛁 2 Bathrooms
🏊 Private heated pool
🌊 Bay views of Tampa Bay & the Skyway Bridge
🏖️ 6-minute walk to Bean Point Beach
🍽️ Outdoor dining & lounge area
🛍️ Minutes from Pine Avenue shops & waterfront restaurants

Ready for your next island escape? Explore Breakaway and book your stay:
https://tinyurl.com/4w6w64pf

Nothing makes us happier than hearing our guests had an unforgettable stay."This place exceeded our expectations! We lov...
07/17/2026

Nothing makes us happier than hearing our guests had an unforgettable stay.

"This place exceeded our expectations! We loved the fact that there are steps down to the Bay! The pool in front… smart. We saw next door the pool was full of birds all day! Amazing stay. We will be back!" — Karen Powell

From peaceful bayfront mornings to thoughtful touches that make every stay even better, reviews like this remind us why Anna Maria Island is such a special place to vacation.

Thank you, Karen, for sharing your experience. We can't wait to welcome you back for another island getaway!

Address

3018 Avenue C
Holmes Beach, FL
34217

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