Places to stay near Anna Maria Island

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

Experience life 4 blocks from the Gulf, ½ mile to Siesta Key — America’s #1 Beach. With effortless access to Sarasota’s dining & arts scene, Siesta’s white sand beaches, St. Armand’s, & Gulf Coast adventure! 2BR boutique bungalow • Sleeps 6 • 4 beds Situated in the coveted Coastal District (‘West of Trail’) — chef kitchen, beach gear, Smart TVs, marble spa bath, laundry, fast Wi-Fi. Grill lobster under stars, unwind in your tropical garden, & walk palm lanes to cafes, and waterfront sunsets.

Be an 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.

Island Time: Open Tomorrow, $175/nt + Fees!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Bayfront Beach access with Heated Pool!

Our modern yet beachy retreat is the perfect oasis on the North end of Anna Maria Island w/breathtaking panoramic views of Tampa Bay & the iconic Skyway Bridge. The backyard oasis features a refreshing saltwater pool & fully fenced backyard, complete w/artificial turf & outdoor shower. Just steps away, you'll find full access to a stunning white sandy beach & the crystal-clear waters of Tampa Bay! Conveniences have been carefully considered, creating the most ideal vacation destination!

2nd House from the Beach with No Roads to Cross

Seaside Sanctuary is the upper level unit of a beachfront duplex. It is the 2nd house from the beach with no roads to cross. The front yard is thirty steps from one of the most pristine beaches on the Gulf of Mexico. The house is located on a quiet residential street near the north tip of the island. The front deck is a great place to watch the sunset. The house is clean, comfortable and well appointed. We welcome well behaved dogs and have a fully fenced yard for your pup to play.

Starfish cottage w/heated pool in PRIME location

Welcome to an old Florida 'The Starfish Cottage" . Enjoy the private heated pool with lush tropical setting. Inside you'll find an open concept living space where dining area, kitchen and living room have been newly furnished with luxurious deep seat couches and lounge chairs, hardwood floors add to the charm. Fresh linens, bath and beach towels are provided along with basic toiletries. Decor has been collected over time and obtained from local artists for a unique old Florida style.

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Salty Harbor AMI pool retreat near the Beach

Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our calendar! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

Anna Maria Island-just a few steps to the beach

Our second-floor condo is located in Holmes Beach within a beachfront condo community that sits directly on the shores of the Gulf of Mexico in Holmes Beach. This 2 bedroom 2 bath condo has a full kitchen with all modern conveniences. Enjoy your morning coffee or your evening dinner on your private outdoor balcony. This recently renovated condo is perfectly situated overlooking the pool and just steps away from the beautiful sandy beach of Anna Maria and also a pickleball court.

Anna Maria retreat house

Elevated home with all the amenities. Walking distance to the beach, chairs and towels provided. Relax in the backyard patio, including pool with waterfall . The shaded balcony overlooks the pool if you need to escape the sunshine. There’s a free trolley that runs all day in AMI if you don’t want to take the car out. The house is located across the street from Bimini Bay, enjoy a jog through these side streets in the morning. Local shops and restaurants that will not disappoint .

Beach Don't Kill My Vibe by Beach Boutique Rentals

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

83rd St Villas West by Duncan Real Estate

Welcome to 83rd St Villas West! A stunning ground-level vacation villa just a 6-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen with Cafe appliances, ample counter space, cook top and oven, extra-large fridge/freezer making meal prep a breeze.