Holiday houses in Holmes Beach

Luxury 3BD Beachfront Retreat with Heated Pool!

Sandy Bottoms Beach House is a luxury Gulf-front retreat where modern comfort meets Florida’s natural beauty. With three king bedrooms—each with its own en suite bath—this home is designed for families, couples, or groups seeking a premium beach getaway. Step through oversized sliding doors to a private patio with a heated pool, outdoor dining, and a direct trail to the sand. Spend mornings walking the shoreline, afternoons lounging by the pool, and evenings watching unforgettable Gulf sunsets f

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.

Hidden Haven / Private Pool & Hot Tub

Your dream bayside escape at this charming single-story haven, just a heartbeat away from the pristine shores of Anna Maria Island. Featuring 4 inviting bedrooms and 2 stylish baths, indulge in the luxury of a private pool nestled among vibrant tropical foliage. Sip your morning coffee or toast to sunset cocktails poolside, wander to the sparkling Gulf, discover the delightful shops and eateries in Holmes Beach. This oasis is perfect for sun-kissed relaxation and exciting island escapades!

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.

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

Ebb Tide by Duncan Real Estate

Come to this Island home and have a vacation of a lifetime! Totally remodeled, this 3-bedroom, 3-bath pool home is well appointed with designer finishes throughout. The living area has plenty of seating for the whole family. The kitchen is outfitted with gorgeous granite countertops and stainless-steel appliances. Start your day with your favorite morning treat at the breakfast bar. There is also a large Florida room with a dining table for six to gather around the family.

Blue Bungalow A

Island duplex - Side A only. Our home is great for both beach & AMI lovers who don't mind not having a pool. The unit is a 2 bedroom-2 full bath; and walkable to beach (3 blocks), Holmes Beach city center restaurants, bars and shops (3 blocks) and the free island trolley (1 block). Anna Maria Island is roughly 7 miles long and crazily enough divided into 3 cities: Bradenton Beach, Holmes Beach & Anna Maria; Holmes Beach is central.

Wonderful 3/2 close to beach! Heated pool!

Escape to this charming 3BR/2BA Holmes Beach retreat, just steps from the sugar-soft shoreline. Bright, beachy interiors create a relaxing vibe, while the private heated pool offers the perfect spot to unwind after a day in the sun. Enjoy easy access to the beach, local shops, and island eats. This inviting getaway blends comfort, convenience, and coastal charm for the ideal Anna Maria Island vacation.

CBC 2-19F: Gulf Front Paradise Awaits!

🌸Get away from the hustle and bustle of Clearwater Beach and opt for a tranquil experience on the peaceful shores of Sand Key Beach. Looking for a quiet, tranquil beach vacation away in a secluded beachfront paradise? Look no further than CBC 2-19F located at Sand Key Beach in Clearwater, FL! This fully updated 19th-floor condo has a spacious open floor plan with jaw-dropping water views!!!

Sea Glass North End • 2bed/2 bath Steps to Beach

Welcome to Sea Glass Cottage—your private retreat on the north end of Anna Maria Island. Just one block from Bean Point’s sugar-white sands, this refreshed coastal home features a private pool, upper deck, and stylish indoor–outdoor living. Enjoy a chef’s kitchen with Wolf and Sub-Zero appliances, an outdoor grill and smoker, and relaxed island charm perfect for families and friends.

Newly updated 2B/2B condo, walk to the beach!

Charming fully updated condo in a quiet beach community. Amazing location! Walk to beaches, shopping and restaurants! 2 bed, 2 bath condo in a small 8-unit boutique complex. Spacious unit fully remodeled with heated pool overlooking a quiet park. Enjoy the beach after a short stroll through the park and then 150 steps to the white sand! Has all the amenities that you will need!

Best Location! Heated Pool~Steps to Beach/Shops!

🌴 Villa #5 Seashell – Your dream beach escape! 🌊☀️ Just 2 mins from Holmes Beach, this 1BR/1BA villa at Islands West Resort is perfect for couples or small families. 🛏️ King bed + queen sleeper, 🏊‍♂️ shared heated pool, 🍔 BBQ, 🌺 tropical landscaping, 🐾 dog-friendly, steps from shops, dining & the free island trolley. 🚗 1 parking spot. Relax, explore & make memories! 🌅