Pet-friendly vacation rentals in Holmes Beach

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!

Enjoy easy living in this updated tropical home! Your private screened lanai is perfect for seamless indoor/outdoor relaxing, with a heated pool and covered dining/lounge area with a 58" outdoor TV! The interior of the home is bright and open with cheerful coastal decor and plenty of room to spread out. We provide everything you need with a well-stocked kitchen, gas grill, game room, beach gear, towels, EV Charger! In a quiet neighborhood with quick access to AMI beaches IMG, parks, and trails!

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

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.

Poolside Oasis on Anna Maria Island!

Remodeled cottage with a lush tropical backyard, which boasts a Private Heated pool with Waterfall and Swim-up Tiki Table, turf putting green ,Weber Grill, patio bar with 55” Outdoor Smart TV! Calypso is outfitted with a cozy Coastal decor, you feel that vacation vibe as soon as you walk in the door. The kitchen offers quartz countertops with Stainless Steel appliances. Both bedrooms have King size beds, living room has a queen sleep sofa. All furniture was brand new in December of 2024

Short Stroll to the Surf! ~ Make Memories on AMI

Nestled in a charming, quiet community of just 8 units, this beautifully updated beach condo offers the perfect blend of relaxation and convenience. The condo is just a short stroll (about 150 steps!) to the pristine white sand beach, where you can soak up the sun and enjoy the coastal views. Wonderful family getaway or couples escape. Private, covered 2 car parking. Laundry in unit. Beach wagon, chairs and gear available. A hidden gem close to everything you need for a relaxing island stay.

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

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.

Newly Remodeled Beachfront Studio - On the sand!

ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

Blanco and Sunset Villas on Anna Maria Island

Back Open Jan '25! Located just 200 steps from the beach you’ll have your feet in the sand in no time. A comfortable living area + fully equipped kitchen. Furnished with island décor and local art. Everything you need including a heated pool, large patio with a Tiki hut, tropical gardens, plus a private outdoor area with a shower for your comfort. Walk to everything – grocery, pharmacy, ice cream, breakfast, pizza, donuts, and the beach which is less than 2 minutes away.

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly just 5 min. walk to the beach. Private lagoon-style *heated* saltwater/low chlorine pool amid lush landscaping with gorgeous rock waterfall. New appliances, HVAC, 60-inch Sony HDTV, Italian leather reclining sofas, BBQ, beach gear, three king bedrooms, all linens provided. Classic Florida one-level home - no stairs. Managed directly by owners, so no crazy fees.

Ohana Hale North 1 Bedroom

Aloha and welcome to our Island Home - Your Ohana Hale Ohana is Hawaiian for family and that is who you are when you stay with us. This one bedroom suite is idea for a couples getaway or small family vacation. Our retreat is nestled on Anna Maria Island, Florida and is a short 7 minute walk to the white sand beaches and turquoise waters. This apartment has a 7 night minimum stay requirement but we have other great properties if you need a shorter stay, just contact us!

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.