Family-friendly holiday rentals in Anna Maria

NEW Heated pool! Steps to the Beach! Islands West

🌴✨ Welcome to Villa #8 AMI Lemon Fish ✨🌴 Step into sunshine and serenity at this cheerful two-bedroom, two-bath villa located within the welcoming Islands West Resort. Just a two-minute walk to the sandy shores of Holmes Beach 🏖️, this bright and beachy retreat is perfect for families, couples, or friends ready to soak up the laid-back charm of Anna Maria Island. With a lush outdoor seating area, BBQ grill, shared pool, and an unbeatable location near dining and shopping, your ideal island es

Green Jacaranda /Bean Point Beach 5 min walk/pool

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

New! Gorgeous home on AMI. Heated pool!

Discover the perfect getaway at this charming 3bed/2.5 bath vacation rental on Anna Maria Island! Centrally located & just a short stroll to the beautiful beach and vibrant Pine Avenue, where shops and dining await. Enjoy the sunny days lounging by the heated pool or challenge your loved ones to a game of ping pong, foosball, or Connect Four. This delightful home is designed for families and friends, offering a cozy atmosphere for unforgettable memories. Book your slice of paradise today!

Heated Pool, Hot Tub, Game Room, Steps to Beach!

Welcome to Island Dreams, the ultimate peaceful escape just 4 min walk from Anna Maria Island's stunning beaches. This fully renovated three-bedroom, three-bath beach house features a Zen-inspired backyard oasis, a private cocktail pool, and a game room! Walk to shops, restaurants, and the trolley stop! Island Dreams offers the perfect blend of relaxation, location, and indoor and outdoor fun! NOTE: Holmes Beach has a 7-day rental minimum. Check in / Check out days are on Saturdays.

Heated pool/Spa~Water Slide and Grotto! 9 Beds!

Welcome to Harbor Haven, a stunning vacation rental nestled in the heart of Anna Maria Island. This 4-bedroom, 7-bathroom oasis is just a 5-minute stroll from the pristine Gulf beaches. Immerse yourself in the ultimate relaxation with our gorgeous freeform pool, complete with a hot tub, waterfall, water slide, and grotto for endless fun and tranquility. Whether you're lounging in the sun or enjoying a family barbecue, Harbor Haven offers the perfect backdrop for unforgettable memories.

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 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 .

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated PRIVATE pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

Pool & Sand Volleyball | 3 Kings | Near AMI & IMG

Escape to Two Palms, a spacious 4-bedroom, 3-bath retreat in Bradenton, Florida. Perfectly located just minutes from the sugar-sand beaches of Anna Maria Island. Designed with comfort and relaxation in mind, this home offers everything you need for a memorable getaway. Step inside to an open-concept living space filled with natural light and plenty of space to unwind. Outside, enjoy a private salt-water pool and a beach sand backyard featuring a sand volleyball court.

Bean Point Bliss by Duncan Real Estate

Welcome to Bean Point Bliss! This stunning 3-bedroom, 2-bathroom pool home has plenty of room for the whole family. Bean Point Bliss is an elegant Island home with living space all on one level. A total of 6 people will stay here very comfortably. The additional area on the ground-level (not under a/c) is featuring a ping pong table, TV, and a seating spot which opens up to the back yard pool oasis.

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.