House holiday rentals in Holmes Beach

Carissa B | Beachside Retreat | Golf Cart | Pool

Welcome to Carissa Loft B, your completely private half of a beachside duplex on AMI! The duplex is designed back-to-back, meaning you have your own private indoor/outdoor spaces, entrance & pool-No shared amenities! Loft B includes: 1pm CHECK IN, 3 beds, 2 baths, full kitchen, 2 living spaces, balcony, heated/cooled cocktail pool & 6 person golf cart included w/stay! Ideal for up to 6 guests. Need more space? You can book both sides for larger groups while still enjoying separate living areas.

Beautiful Beach house! Heated pool and spa!

Discover your dream getaway at this beautifully decorated vacation rental in Anna Maria Island. This stunning 4-bedroom, 4.5-bathroom home offers luxury and comfort, featuring a spacious open-concept living area, modern kitchen, and elegant furnishings. Enjoy the private pool and hot tub, and the beach is just a 5-minute walk away. The highlight is the rooftop deck, where you can soak in breathtaking sunsets. Experience the perfect blend of style and convenience for your unforgettable vacation!

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.

Sandy Toes

This newly remodeled, upscale villa is on a quiet island street less than 300 steps from the powder white beach of Anna Maria Island. Over a dozen restaurants within a quarter of a mile short stroll and many shops close by to visit as well. The private villa includes a "treetop" front balcony which is a guest favorite to enjoy gulf breezes & relaxation. A fabulous, covered side porch overlooks extensive tropical plants and set up with comfortable chairs and your own private gas weber grill.

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.

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

Family Beach Retreat | Epic Game Room + Cabana Bar

Just 3 blocks from the beach and steps to the canals, this bright and breezy 3-bed, 3-bath coastal retreat is designed for easy, family-friendly living. Inside, you’ll find king beds, a fully stocked kitchen, and laid-back coastal style throughout. Outside, enjoy al fresco meals or sunset cocktails at the cabana bar, while the game room keeps the fun going rain or shine. With games, beach gear, and good vibes, Sunburst Cottage is the perfect setting for your next island escape.

Americana AMI Lighthouse 3BR w/pool + rooftop deck

Discover this unique lighthouse vacation rental w/private pool on Anna Maria Island. The Lighthouse has 3 bedrooms, 2.5 baths with an open plan living/kitchen/dining which is perfect for a family vacation or getaway with friends. Located in Holmes Beach, the home is only a short walk (approx. 6 min) to the beautiful Gulf beach. The house has been lovingly decorated with retro memorabilia creating a vintage americana aesthetic. Enjoy our budget-friendly pricing.

83rd St Villas East by Duncan Real Estate

Welcome to The 83rd St Villas East! 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 Café appliances, ample counter space, cook top and oven, extra-large fridge/freezer making meal prep a breeze.

Luana Breeze close to Ami beach. Pool & Spa

Vrc16-000137 Welcome to "Luana Breeze" located at 208 68th Street, Holmes Beach. Find ease and relaxation the moment you arrive, this property is about 100 steps to the Gulf of Mexico and one of the best beaches on the West Coast of Florida. This ground level beach house offers 4 bedrooms, 3 bathrooms (2 are ensuites) and all the coastal charm you expect from a luxury vacation rental home that is located on beautiful Anna Maria Island.

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.