Holmes Beach Vacation Homes for Sale

The sand and water of the Gulf beach is just one home from this lovingly maintained, solid concrete residence, offering timeless coastal charm with peace of mind. Built and cherished by the same family since its construction, the home’s living space on the second floor has never experienced interior storm damage and features hurricane-rated rolldown shutters.

This elevated Holmes Beach retreat is all about location, just steps from the sugar-sand shoreline of Anna Maria Island and the turquoise waters of the Gulf. Thoughtfully designed for relaxed coastal living, this three-bedroom, two-bath home invites sunlight through a wall of sliding glass doors that open to the screened porch, framing tranquil views of swaying palms and hints of the Gulf beyond.

Nestled within the serene landscape lies this captivating sanctuary, offering a 4-bedroom, 2.5-bathroom retreat sitting gracefully on one of the larger lots on Anna Maria Island, boasting a spacious 14,500 sq ft, presenting an exceptional opportunity for those seeking a permanent residence or a second home.

Under contract-accepting backup offers. The epitome of coastal charm, this beautiful tropical oasis is a perfect slice of paradise! Featuring an open kitchen and family room area with gracious French doors leading to a lovely balcony that overlooks a Zen like backyard. Spend relaxing days savoring a beautiful paver patio with private saltwater, heated pool surrounded by lush, tropical foliage.

Fantastic Vacation Rental Loved By All Generations Welcome to the ultimate island vacation home. Located in a weekly rental zone, it is positioned to be an outstanding income producing property with strong vacation rental history and bookings secured into Summer 2026, making it an exceptional investment opportunity for any buyer.

SHORT TERM RENTALS One block from the beach! Welcome to Sand Palace on Anna Maria Island! This elevated 3 bedroom, 2.5-bath coastal home offers the perfect blend of relaxation and as a successful rental investment just one block from the sugary sands of the Gulf.

NEW METAL ROOF COMING SOON! Check out "La Isla Bonita"on Holmes Beach! A successful vacation rental property just 5 minutes (400 steps) to the gorgeous Anna Maria Island beaches! This concrete block construction has a total of 3515 total sq.ft. This contemporary QUALITY BUILT home in 2006 with an ELEVATOR has 4 bedrooms/4 baths ENSUITE. TURN-KEY FURNISHED. WEEKLY RENTALS.

Tucked into one of Holmes Beach’s most desirable neighborhoods, this beautifully updated 4BD/3BA ground level retreat offers the perfect blend of laid back coastal charm and modern comfort. With a proven track record as a successful vacation rental allowing weekly stays, it’s an ideal opportunity for investors or anyone dreaming of their own tropical getaway.

Welcome to a rare investment opportunity on Anna Maria Island. A coveted triplex in the heart of Holmes Beach. No need to cross busy streets, his gem is steps to the island’s world-famous Gulf beaches and minutes from the vibrant Bridge Street. One of the few multi-unit properties available on the island, this income-producing triplex offers exceptional flexibility and long-term potential.

Your Lucky Day~ buyer Financing Fell through & Back on the Market!! Mediterranean-inspired coastal luxury meets the laid-back charm of island living in this fully furnished, elevated Anna Maria Island Villa, just one block from the Gulf and a short stroll to Skinny’s and Manatee Beach.

Just steps from the sugar white sands of the Gulf, this elevated coastal retreat captures the essence of relaxed beachside living with the comfort of thoughtful design.

Property did NOT flood! Sold turnkey! Stunning 4 bedroom 4 bath luxury duplex pool home just 1 block from the beach! Newer heated salt water pool & backyard is a private oasis in paradise. Each unit features its own kitchen, dining area, living room & 2 bedrooms & 2 beautiful baths with private enclosed porches. Shared 1 car garage & inside laundry room with full-size washer & dryer.