Pet-friendly holiday rentals in Anna Maria

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.

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: -We typically have shorter stays available, just ask! -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

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.

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.

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.

Sweet & Simple guest suite Close to Everything.

Keep it sweet & simple at this peaceful and centrally-located private room close to downtown and the beaches. The room has it's own entryway from outside and boasts, TV, Wi-Fi, a full private bathrooms. The walk in closet space functions as a breakfast nook with mini refrigerator, microwave, and the necessary basic breakfast utensils. The room is also pet-friendly and close to major highways and transportation hubs. Come and call this space home for your stay in Saint Petersburg.

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

Ohana Hale North 1 Bedroom

SPECIAL - Stay 7 nights and pay for 6 nights from 6/30/25 to 12/18/25!!! If you need a lesser stay, please contact us as we have other properties! Aloha and welcome to our Island Home. 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.

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.

Cozy Studio - quick walk to #1 Siesta Key Beach!

Recently renovated and updated! Adorable studio just steps from Siesta Key Village, and a quick walk to the beach. Spend your day exploring the key, swimming in the ocean, and experiencing the local restaurants and shops. Enjoy coffee in the mornings on the patio, and use the available bikes to catch a beautiful sunset each night. **Please note: - No excessive noise or Parties/Events will be allowed** - No Smoking inside the unit** - Quiet hours from 10 PM to 7 AM**

Kayak w/ Dolphins - Private Entrance Studio

Paddle with dolphins in Palma Sola Bay from this private-entrance, 2-room studio with living room, bedroom w/ queen, bathroom, food prep area (no kitchen sink). Two TVs, WIFI. Dock access in back yard includes use of kayaks/canoe or docking your boat. Quiet on dead-end street. Owner lives in back of house facing canal (see photo). Your space is private with a tropical street entrance & access to the back yard. Non-shedding dog considered with prior approval.