Holmes Beach, FL Homes for Sale under $1,500,000

Imagine waking up to views of sugar sand beaches and the turquoise waters of the Gulf. Imagine no longer as you can enjoy this beachfront lifestyle from this 2 bedroom, 2 bath condo in the Beachfront Condominium complex, Tiffany Place. From the moment you enter the unit you will realize its many upgrades: the polished porcelain tile in the foyer and kitchen, the engineered hardwood flooring

Helen Ross A PARADISE INC REALTOR

Freshly painted and ideally positioned in one of Holmes Beach's most sought-after weekly rental zones, this exceptional duplex presents a rare opportunity to own an income-producing property on beautiful Anna Maria Island. Each side offers 2 bedrooms and 2 bathrooms with comfortable, well-designed living spaces ideal for vacation guests or personal use. Currently operating as a short-term rental,

Brooke Doucett MICHAEL SAUNDERS & COMPANY

Island living awaits at 210 84th Street, Holmes Beach, FL 34217. This 2-bedroom, 2-bathroom pool home offers the perfect opportunity to own a piece of Anna Maria Island, one of Florida's most desirable Gulf Coast destinations.Designed for enjoying the Florida lifestyle, the property features a private pool, comfortable indoor living spaces, and outdoor areas ideal for relaxing after a day at

Chisa Stephenson REAL BROKER, LLC

Welcome to "Captains Quarters" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $125k in rental revenue in 2025. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley

Amanda Cornett PINEYWOODS REALTY LLC

COASTAL INVESTMENT OPPORTUNITY! Elevated duplex. Weekly rentals. One block to the beach. Rare deeded boat slip. Turnkey, Fully Furnished, and Income-Producing from DAY ONE! Welcome to island living at its finest at 8106 Gulf Drive, Units A & B, in Holmes Beach on beautiful Anna Maria Island. This Property offers the ideal blend of personal retreat and exceptional income-producing opportunity,

Danielle Redner FLORIDA EXECUTIVE REALTY

Experience refined coastal living in Holmes Beach. This exceptional turnkey 3BR/2.5BA residence showcases impressive curb appeal with pristine landscaping that sets the tone from the moment you arrive.Inside, you’ll find an expansive, light-filled interior with an open-concept design that seamlessly blends comfort and sophistication, ideal for both elevated everyday living and upscale

Greg Bayer BEACH HOUSE REAL ESTATE LLC

Newly updated with fresh paint throughout, brand new stainless steel appliances, quartz countertops on kitchen and bathrooms and so much more!! Nestled near the north end of Anna Maria Island, 215 81st Street is a three-bedroom, two and a half bath home boasting over 2,000 square feet of living space—an Airbnb gem zoned for weekly rentals. Just two blocks from some of the island’s most pristine

Johnny Hopper PREFERRED SHORE LLC

Competitively Priced to sell, come see this beautifully maintained home for yourself! Welcome to your slice of Old Florida charm in the heart of Holmes Beach on Anna Maria Island. Just a 2-minute walk to the beach, this turnkey furnished home captures the easygoing coastal lifestyle that makes Holmes Beach so special. With its laid-back island feel, tropical setting and inviting spaces, this

Valerie Padur PREFERRED SHORE LLC

Wake up to Gulf breezes, stroll across the street to the sugar-white sands and turquoise waters of Anna Maria Island, and end each day watching spectacular sunsets from your private wraparound deck with partial Gulf views. This beautifully updated and fully furnished three-bedroom, two-bath home with two car garage offers the ultimate island lifestyle while allowing weekly rentals, creating an

Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

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. Thoughtfully renovated over seven months between 2023 and 2024 with the owners investing

Dean Hinterstoisser KELLER WILLIAMS ON THE WATER S

Pre-Construction. To be built. Why buy old when you can get new for the same price? Green Street Builders brings 35+ years of experience, and refreshing coastal elegance at an unbeatable $900/sqft price point. The plans speak for themselves. 4 defined sleeping areas per side (including an open air loft), high-functionality, and open concept design with vaulted ceilings. Quartz waterfall counters,

Jason Skowronski COMPASS FLORIDA LLC

Smart Buyers: This Price Improvement Is For You. 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

Shauna Ruby BLUESRQ REAL ESTATE INC

INCREDIBLE VALUE! 5 BEDROOM HOME ON ANNA MARIA ISLAND WITH PROVEN RENTAL HISTORY- THIS IS THE ONE!!! Imagine owning a place where every day feels like a vacation. Located on a peaceful corner lot in the heart of Holmes Beach, this spacious 5-bedroom pool home offers the perfect balance of relaxed island living and modern comfort—just steps from everything that makes this island so

Jay Travis RE/MAX ALLIANCE GROUP

This charming ground-level 3-bedroom, 2-bathroom home with a private pool offers an exceptional investment opportunity in a prime location just minutes from the pristine sandy beaches of Anna Maria Island.Currently heavily booked as a vacation rental, it delivers strong occupancy and consistent cash flow in one of the most desirable short-term rental markets along the Gulf Coast. The inviting

James Wilson SATO REAL ESTATE INC.

Welcome to "Pineapple Paradise" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $130k in rental revenue in 2025. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley

Amanda Cornett PINEYWOODS REALTY LLC

This property is best suited for buyers seeking short-term rental income, a multi-unit investment, or a flexible owner-occupant strategy in a prime Holmes Beach location on Anna Maria Island. This income-producing triplex is located just steps from the Gulf beaches with no busy streets to cross and offers three separate rental units, including a 3-bedroom, 1-bath residence upstairs, plus a

Brooke Doucett MICHAEL SAUNDERS & COMPANY

The fabulously updated kitchen and open floor plan, make this 3 bedroom/2 bath half duplex a picture perfect island escape. Ideally situated on a quiet corner lot in the heart of the island, it is a straight walk down the street to the sugar sand beach, making it a popular vacation rental too! The split bedroom plan is perfect for hosting, and the updated, private, heated pool and trellis invite

Erin Leathem ISLAND REAL ESTATE-ANNA MARIA

This home is a renovated 3-bedroom, 2-bathroom 1⁄2 duplex with a private backyard and pool. The primary suite has an en-suite bathroom. There is a covered upper deck and a lower covered outdoor living and dining area. It is in a weekly rental zone and has good rental history and 5-star reviews. It has a heated and chilled pool. This lovely property is convenient to the beach and in a very quiet

Moe Mossa SAVVY AVENUE, LLC

Your PERFECT BEACH HOUSE Awaits on Anna Maria Island! Just 2 blocks to the gorgeous Gulf and 1 block to the Bay, this beautifully updated & elevated 2-bedroom, 2-bath ++ coastal retreat delivers the ultimate in relaxed island living. Thoughtfully renovated, this cozy gem features wood flooring throughout, an airy open-concept layout, and a super spacious chef's kitchen complete with stainless

Sabrina Ullmann RE/MAX ALLIANCE GROUP

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. The split floor plan ensures

Jennifer Sekel BEACH HOUSE REAL ESTATE LLC

COASTAL INVESTMENT OPPORTUNITY! Elevated duplex. Weekly rentals. One block to the beach. Rare deeded boat slip. Turnkey, Fully Furnished, and Income-Producing from DAY ONE! Welcome to island living at its finest at 8106 Gulf Drive, Units A & B, in Holmes Beach on beautiful Anna Maria Island. This Property offers the ideal blend of personal retreat and exceptional income-producing opportunity,

Danielle Redner FLORIDA EXECUTIVE REALTY

Price improvement! Welcome to this modern, yet warm and cozy, 3-bedroom, 2-bathroom home on the north end of Holmes Beach on Anna Maria Island. From the moment you arrive, the estate makes a striking first impression with its notable presence and contemporary landscaping. Updated throughout in 2026, this move-in-ready residence offers almost 1,400 square feet of stylish, single-level living

Dylan Casarez INVESTCOR REALTY LLC

It’s a short walk to the beach to enjoy the beautiful water and sunsets and then back to your turnkey furnished vacation home with a pool that offers seating and a table for the cocktail hour. The courtyard also offers a covered, shady patio with a dining table to enjoy the cool breeze through the palm trees. Totally updated floor plan with a great flow! Close to shops and the free trolley. An

Kathy Caserta MIKE NORMAN REALTY INC.

OVER 150K INCOME OVER LAST 12 MONTHS!!! Embrace the pinnacle of island luxury with this impeccably designed, turnkey Holmes Beach duplex—operating as a successful Airbnb and ready for seamless ownership transition. Each side features two spacious bedrooms and one bath, complete with gleaming marble countertops, white shaker cabinetry, elegant, natural-flow tile backsplashes and breathtaking

Johnny Hopper PREFERRED SHORE LLC

Virtually Staged. This 3 bed/2 bath coastal charmer is just steps to the sugar sand beach, with a heated, salt water pool with full spa features! Create your own style in this cute cottage, where the hard work has already been done for you! New Luxury Vinyl Plank throughout, fresh paint, new doors, new bathrooms, new cabinetry and new appliances, means nothing left for you to do but add your

Erin Leathem ISLAND REAL ESTATE-ANNA MARIA

Welcome to your slice of island living in the heart of Holmes Beach. Perfectly positioned on a deep-water canal, this 2- bedroom, 2-bath ground-level home offers the ultimate Florida lifestyle for boaters and beach lovers. With a 60-foot dock equipped with water and electric, a 10,000 lb boat lift, you can launch your boat, kayak, or paddle board directly from your backyard. Southern exposure

Stephen Hachey FLAT FEE MLS REALTY

Interior photos coming soon! Location, location, location! Enjoy this elevated 2-bedroom 2 bath home located in central Holmes Beach on Anna Maria Island. You are three houses away from beach access and all of a 5 minute walk to watch sunsets and relax on the Gulf Beaches. This home has been renovated, and is turnkey furnished in a beachy décor to continue as a productive vacation rental or bring

Amanda Cornett PINEYWOODS REALTY LLC

Experience the ultimate beachfront retreat at the "ANNA MARIA ISLAND CLUB" where LOCATION IS EVERYTHING AND THE GULF VIEWS ARE STUNNING! This exceptional 2B/2B ISLAND PARADISE condo offers bi-weekly rentals and is just steps away from the pristine sandy beaches of Anna Maria Island. This fully remodeled unit is a true gem, with a unique design is offered TURN-KEY furnished and creates a welcoming

Cindy Quinn SATO REAL ESTATE INC.

Welcome to the highly sought-after Anna Maria Island Club, one of the island's premier Gulf-front communities where opportunities like this rarely become available. This beautifully maintained 2-bedroom, 2-bath condominium is being offered turnkey furnished, making it truly move-in or rental ready from day one. Currently operating as a successful active vacation rental, this property offers an

Jomarie Alicea PREFERRED SHORE LLC