Holmes Beach Vacation Homes for Sale

This rare ground-floor, direct Gulf-front residence at The Coconuts offers true toes-in-the-sand access and unobstructed sunset views the moment you walk through the front door. Step from your living room directly onto the sand — no stairs, no elevator — just instant beachfront living in one of the most coveted locations on Anna Maria Island.

Coastal elegance meets modern living in this beautifully updated Holmes Beach retreat located on the peaceful stretch of 57th Street—one of the narrowest parts of Anna Maria Island. This prime location offers the least crowded beach access on the island, just steps from the shoreline.

Never miss a sunset with the view from this beachfront GEM! A true 3 Bedroom, 2 Full Bathroom with 1,516 square feet, including an indoor Laundry Room. One of only 6 units of this size in the building. The Master Suite boasts a panoramic beach view, walk in closet and en-suit bath, while the 2 remaining bedrooms have large closets and comfortable natural lighting.

Welcome to this newly renovated duplex situated in the heart of Holmes Beach on beautiful Anna Maria Island! Each side of this property features 2 bedrooms and 2 bathrooms, offering a cozy and comfortable retreat just a short stroll from pristine beaches, shopping, and popular restaurants.

NEW METAL ROOF installed in 2025. Welcome to this lovely canal-front, turnkey furnished residence located in the exceptional Key Royale community, Anna Maria Island's premier neighborhood for boating and golf enthusiasts.

This easy living 3 bedroom, 2 bath home combines comfort and accessibility, offering a tranquil retreat in the heart of Holmes Beach with a beautifully updated interior and a lush, private backyard oasis.

Weekly rental! Exceptional Investment Steps from Holmes Beach. Welcome to Blue Oasis, a fully renovated ground-level retreat just steps from Holmes Beach and the turquoise waters of the Gulf of Mexico. This stunning 2-bedroom, 2-bath home combines modern luxury with island charm. Featuring a versatile den with a pocket door for added privacy, it’s perfect for a home office or guest space.

One-of-a-kind beachfront condominium at Tiffany Place. Rarely available in this boutique building of only 33 units is this fully renovated coastal retreat offering direct Gulf views from the primary suite and balcony, something few units can claim.

Beautifully updated investment duplex with 4 bedrooms, 2 full baths (2/1 on each side) 2 parking spaces for each unit. Units are presented turnkey with all furnishings and existing bookings for 2024. Metal roof built in 2015. Hurricane windows and doors installed in 2018. Both AC units replaced in 2018. 2022 Upgraded Electric service. New water heater 2023.

One or more photo(s) has been virtually staged. Pool Home on Anna Maria Island Just steps from the Gulf of Mexico, this 2-bedroom, 2-bath coastal cottage offers 1,200 sq ft of living space on a 9,000 sq ft lot. Enjoy your private pool surrounded by island breezes, or stroll to Holmes Beach, boutique shops, and dining.

CUSTOM QUALITY HOME REMODEL: Welcome to Turquoise Beach Bungalow—your perfect slice of island life. Completely reimagined inside and out in 2024–2025, this vibrant coastal retreat combines classic island charm with modern comfort and craftsmanship.

This turnkey, island-style retreat, built in 2013, is offering three bedrooms and two full baths, spanning approximately 1,797 square feet of living space. Though technically part of a condominium association (Marina Drive Condominium Association), this home feels and lives like a detached single-family residence, giving owners/renters the privacy and comfort of a standalone villa.