Holiday rentals in Anna Maria

Heated Pool, Elevator, Waterfront, Fire Pit, Dock

Escape to The Blue Ark, a 3-story home inspired by Noah’s Ark. Families will love this peaceful retreat, blending luxury and comfort. Discover the island's only natural lagoon, boasting stunning views, manatee and occasional dolphin sightings! Unwind by the heated pool, fish from the dock, or take an easy 4-5 minute walk to the beach. End the day with a drink by the fire pit on the top deck, watching the sunset. The Blue Ark has an elevator, 3 bedrooms + extra sleep space, 8 beds and 4.5 baths.

Green Jacaranda AMI Duplex B, 5 min walk to beach

Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

Duplex Heated Pool Walk to Beach

Just a short 3-block stroll to the stunning Anna Maria Island Beach, Bayfront Park, and the charming shops and restaurants along Pine Ave, this exquisite property offers the ultimate island getaway. Experience luxury and comfort in one of two custom-designed villas by the renowned island architect, Gene Aubry. The duplex villas share a heated pool and a spacious backyard deck, but each has its own private entrance, driveway, and outdoor areas for you to enjoy. Luxurious but laid back comfort.

Carissa A | Beachside Duplex | Golf Cart | Pool

Welcome to Carissa Loft A, your completely private half of a beachside duplex on AMI! The duplex is designed back-to-back, meaning you have your own private indoor and outdoor spaces, entrance & pool-No shared amenities! Loft A includes: 3 beds, 2 baths, full kitchen, 2 separate living areas, balcony, heated/cooled cocktail pool, & garage w/golf cart! Ideal for up to 6 guests. Need more space? You can book both sides of the duplex for larger groups while still enjoying separate living areas.

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!

Manatee Sanctuary - in the heart of Anna Maria

Welcome to Manatee Sanctuary – a spacious 3 bed/ 2 bath canal-front retreat with a private heated pool and hot tub, located in the quiet and highly sought-after North End of the island. This serene and private oasis offers everything you need for a relaxed and memorable beach vacation. The home features an open-concept living and dining area, fully stocked kitchen, and an upstairs porch ideal for morning coffee or evening relaxation. The backyard opens onto a peaceful saltwater canal.

Luxury 2BR Oceanfront Condo + Rooftop Patio

Modern Condo with Stunning Ocean Views: - Cozy turf patio - Smart TVs and high-speed WiFi - Fully equipped kitchen - Two private parking spots for hassle-free stays - Just a 2-minute walk to the beach Unique Features: - Social Media worthy grass wall - Two comfortable beds: one king & one queen, ensuring a restful sleep - Queen-sized inflatable extra bed Prime Location: - Conveniently located next to the AMI trolley stop - Within walking distance to dining, a gym, and more!

Pergola Oasis | Walk to Beach + Outdoor Living

Welcome to Salty Palm, a newly remodeled coastal retreat in the heart of Holmes Beach. Just a short walk to the white sandy beaches of Anna Maria Island, this home features a private covered pergola with outdoor lounge seating and dining, creating the perfect space to relax day or night. Steps from shops and eateries, with nearby bike and golf cart rentals, plus access to community amenities including a boat ramp, kayak launch, fishing dock, and tennis & pickleball courts.

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.

Key Lime Cottage | Hot Tub | Steps to Beach

Key Lime Cottage is a charming 3BR/2BA coastal retreat just across the street from the Gulf beach and two houses from the iconic Rod & Reel Pier. This pet-friendly home features a private fenced yard, hot tub, bikes, and paddle boards, plus a fully stocked kitchen, Smart TVs, and fast Wi-Fi. Walk to Pine Avenue shops and restaurants, enjoy effortless beach access. Relax, unwind, and experience the best of Anna Maria Island—right outside your door.

L'Oasis East w/Dip Pool

Completely remodeled, this beautifully 2-bedroom duplex, crafted to enhance your living experience. Every detail has been thoughtfully designed to create a serene and inviting atmosphere. New images showcase this stunning transformation, come visit us to see the beauty in person! Additionally, West and East are now available for rent together, featuring convenient adjoining doors through the utility room.

Ocean72 | Heated Pool & Spa | 2BR Near Beach

Welcome to your island escape at Ocean72 in Holmes Beach! Just a short walk to sugar-white beaches, this coastal retreat features a private heated pool & spa, lush tropical landscaping, and seamless indoor-outdoor living. Enjoy a fully stocked kitchen, plush beds, and beach gear. Guests also have the option to add a private golf cart for easy island exploring and beach trips.