Pet-friendly holiday rentals in Holmes Beach

+ Anna Maria Seaside Escape +

Discover the perfect beachside escape at our centrally located 2-bedroom haven on Anna Maria Island, just steps from the sand and some of the island's top amenities! We are required to show 7 night minimum bookings only, however please send us an inquiry for custom dates 1 Block to the Beach 2 Bed / 1 Bath 2 Kings Balcony with Patio Furniture Washer & Dryer on-site WIFI Elevated Beach House (Duplex) Beach Towels & Chairs Gas Grill - (shared) Parking for 2 Cars, Including 1 enclosed garage space

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

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!

Sea 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.

Steps to Beach |Heated Pool+Spa|Direct Pool access

Steps from beach access! Captain's Quarters is a 1 bed/1 bath with a sleeper sofa to sleep 4, a full kitchen & living area. This duplex style bungalow has shared backyard space including a heated saltwater pool, spa and gas grill. Close to the free trolley stop which is only one block away running north and south on AMI, shops and restaurants! Some short stays available. Captain's Quarters is one of 4 bungalows at The Gulf Drive Inn. Inquire to reserve more than one! Inquire for shorter stays

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.

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.

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

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!

Cabin 2 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, the free AMI trolley, and nightlife. You’ll love my place because of the location and the ambiance. It is nestled in the lush tropical landscape of Spinnakers Vacation Cottages. You will find Cabin 2 is a perfect spot for an island getaway. My place is good for couples, solo adventurers, families (with kids), and certain size breed and weight dogs. Spa maintains same temperature as pool.

LivingGood by Duncan Real Estate

Enjoy vacation bliss at this completely remodeled island pool home called LivinGood! The house features the perfect blend of modern luxury and beachside charm. Convenient ground level and located just two blocks from the beach, the spacious split floor plan offers 3 bedrooms and 2 bathrooms with a private primary ensuite for ultimate privacy and split system A/C for climate control. Up to 6 people can vacation here.