Holmes Beach Vacation Homes for Sale

PRIME LOCATION | BRAND NEW RENOVATIONS | ELEVATED-LUXURY-LIVING | ELEVATOR | FENCED SALTWATER POOL | MOVE-IN READY | Located on a peaceful street and embraced by the natural beauty of a mangrove preserve, this elevated coastal residence delivers privacy, modern luxury, and a coveted Holmes Beach lifestyle.

Step onto the spacious screened front porch, now featuring Timber Tech by Azek Porch Collection decking, framed by original Pecky Cypress siding, and enjoy the timeless charm of this lovingly restored 1940s 2 bed / 2 bath craftsman beach cottage just steps from the Gulf. This home blends Old Florida character with today’s comfort.

This beautifully updated 3BD/2BA coastal home located on a large 10,709 lot captures the essence of laid back island living with a bright, open interior and a backyard designed for total relaxation. Inside, warm wood-style flooring runs throughout, setting a comfortable tone that pairs perfectly with the home’s coastal palette.

Welcome to this rarely available Gulf-front condo, a 2 bed/2 bath corner unit offering uninterrupted views of the Gulf from nearly every room. This condo was completely remodeled in 2025, with all-new A/C, water heater, kitchen, baths, flooring, and fixtures throughout. Impact sliders frame sweeping Gulf views and open to a private patio that melts into the sugar-white sand.

GREAT VACATION rental history with many repeat guests!!!! This charming home at the beach could be all yours. Nestled in the heart of Holmes Beach, where you can take a short stroll down Holmes Boulevard to city center where you will find adorable shops and restaurants where you can sit, sip, and dine and enjoy a real small town coastal experience.

This is your golden moment! Units 1, 2, 3 and 6 are all listed for sale and is zoned for nightly rentals. Beachfront boutique building is comprised of only six units. This top-floor two-bedroom, two-bath unit has breathtaking views of the sugary sandy beaches of Anna Maria Island and the Gulf. This is a rare opportunity as unique buildings like these are few and far between.

Soaring above the coastline on Anna Maria Island, this rarely available 5th floor condo at the Martinique delivers a front row seat to one of the most spectacular views on the Gulf Coast. Expansive windows in the living area and primary suite frame an endless horizon of blue, casting natural light across the updated interiors.

Enter into luxury coastal living with this beautifully remodeled two-bedroom, two-bath beachfront condominium at sought-after Gulf Sands on Anna Maria Island. Directly on the Gulf of Mexico, this rare Gulf-front unit offers sweeping, unobstructed views of the beach and sunsets from your private balcony.

Under contract-accepting backup offers. THIS ISLAND RETREAT ALSO IS A BOATERS DREAM, SEPARATE DEEDED BOAT SLIP . Do not miss out on this lovely coastal single family island home also has a separate deeded boat slip and water access right across the street from you. No bridges to go under either, just perfect for the avid boater.

Welcome to Catching Waves, a charming coastal retreat nestled in the Heart of Holmes Beach on beautiful Anna Maria Island, FL. This fully furnished, COMPLETELY RENOVATED, 2-Bedroom, 2-Bathroom Villa provides the perfect blend of comfort and privacy. Surrounded by gently swaying palm trees on a quiet street, they spared no expense in the remaking of this home, top to bottom.

WELCOME to APPLETINI, a charming BEACH HOUSE on ANNA MARIA ISLAND! ~This fun, Key West style pool home has 2 lovely bedrooms & 2 full baths. Enjoy highly desirable & easy ground level living. With its x-large sparkling heated pool, resort style waterfall feature and swim up Tiki umbrella bar, it is the perfect spot after a day at the beach.

Take a look at the new look of this 3BR/2BA elevated townhouse in North Beach Village HOA2. Just repainted to give it a lively, beachy look! Home was totally remodeled in 2016-2017 with new kitchen with granite counters, breakfast bar, beautiful new cabinets and pantry with light tile floors. Luxury vinyl plank flooring in the rest of the home.