Holiday rentals with outdoor seating near Bean Point Beach

Beach & Bay Walk • 5 Minutes to AMI

Experience the ultimate beachside retreat in this newly renovated 1/1 condo, located within walking distance to the serene beauty of Palma Sola Causeway Parks Bayfront beach, jet-ski rentals, and horseback riding and also a quick drive/bike from the beaches of Anna Maria Island. This well-positioned condo offers the perfect balance of convenience and tranquility, providing easy access to the natural wonders of the island and the vibrant attractions nearby, including canal fishing, jet skis, etc.

Birdsong-Steps to Bean Point Beach Heated Pool!

Welcome to Birdsong, a picture-perfect 2-bed, 2-bath home situated in Anna Maria, Florida. Recently refreshed with coastal décor, this inviting property is ideal for families or small groups seeking a relaxing getaway. With just a short 3-minute walk to the beach, Birdsong provides an excellent blend of comfort & convenience, allowing you to fully immerse yourself in the beauty of Anna Maria Island. The fenced backyard features a heated pool, outdoor dining, BBQ grill, beach chairs, & cart.

Charming Beach house amongst huge Banyon Trees

Charming bright beach house set amongst grand Banyan trees on tip of Anna Maria. 3 min's stroll over a small fishing bridge to historic Pine Ave w/ quaint eateries and shops. Huge fenced yard voted "A Tropical Paradise" Porch sits among huge banyan trees with native birds. 7 min’s walk to bay front beach or rod and reel pier for fresh meals, cocktails, fishing w/ equip & bait supplied, from there stroll along The beach to "Bean Point" voted 1 of the most beautiful beaches in the world.

Breezy Harbor AMI pool retreat near the Beach

Charming Breezy 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 open 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

Beachfront in Pass-A-Grille w/ 2 bikes

Enjoy an intimate and relaxing stay on the best stretch of the St. Pete Beach of Pass-a-Grille. Walk out your door to the white sand towards the famous Don Cesar or dine on your deck facing the water. Free parking, 2 bikes, SUP board, towels, umbrella, beach chairs, & cooler! We are allowed 3 rentals under 28 yearly. Please inquire to see if you are one of the lucky guests to come. We love long term guests but understand not everyone can do this and simply need a little escape! 🤍

Beach House w/Private Pool & Spa

Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the beautiful beach is right by the house. This 3 bedroom 2 bathroom home is situated on a corner lot on a quiet street and is located just steps to the beaches of the Gulf of Mexico. Enjoy the private pool and spa, surrounded by tropical landscaping. Tons of beach gear included! It is located in a great area to explore by bike, ride to Pine Ave., Bayfront Park, the Rod & Reel Pier, etc....

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!

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Sea Shack - 2bd/2ba POOL Home

Welcome to Sea Shack, an inviting ground level vacation home with a pool just steps away from the beach! Visit Pine Ave’s locally-owned boutiques and restaurants just a five-minute walk away. This rental accommodates up to 6 guest. Fully equipped kitchen has plenty of storage space for all your cooking necessities. Friends and family can gather in the living area for movie night or a bored game. have a fun-filled day in your backyard oasis, swim in the gorgeous pool.

Green Jacaranda AMI Duplex A, 5 min walk to beach

Location! North end of Anna Maria Island . This charming two story duplex- each unit has two bedrooms , one bathroom. Rent one unit or both. Perfect for a group of extended family and friends. Steps to the Bean Point Beach . Includes beach chairs, umbrellas and all you need for a perfect day at the beach! Heated pool , private seating, grilling areas, bicycles and much more available.MAX Occupancy - 4 people including children of any age.

Blue Heron Cottage - Anna Maria Island

Great 1 bedroom, 1.5 bathroom cottage on the quiet north end of island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Fern 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.

The Boathouse

Would you like to feel like you are sleeping in a tree house with all the luxuries and comfort of a high end hotel? Then welcome to our brand new guest house, which accommodates a maximum of two guests and is a completely private tropical oasis. Standing on the edge of Lake LaVista, surrounded by tropical palms where you have use of the private and beautiful pool which we heat during the winter months.