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Holmes Beach Holiday Rentals

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    Travellers to Holmes Beach are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to On Island Time; a stunning, entirely new luxury rental home only 3 minutes' walk from the powdery white sand beaches and Gulf of Mexico. With its own private heated salt water pool with spa, 3 bedrooms and 2 bathrooms this is the epitome of luxury. Everything is brand new!!! 3 flat... View all property information
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    Holmes Beach, Anna Maria Island 34217
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      Hidden Cove is a slightly ironic name for these Holmes Beach vacation condominiums. They’re some of the most popular places to stay on Anna Maria Island! But how couldn’t they be when all that separates you from our sugar sand beaches are a few charming, sea oat lined steps. All the Hidden... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Accommodating up to six guests for a fun laid back beach vacation, Casa Sierra 205 B offers the perfect two bedroom, two bathroom getaway for you and your family. Centrally located on Anna Maria Island, Casa Sierra 205 B is near everything for an entertaining stay including gulf beaches, free... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    The While Away, located at 6203 Holmes Blvd. in Holmes Beach is a two bedroom, two bath, ground level duplex with a private heated pool. This very spacious duplex is located in a quiet, residential neighborhood just a short stroll to the beach, shopping or the library. It’s a perfect spot to... View all property information
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    Holmes Beach, Anna Maria Island 34218
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Paradise Found at this Anna Maria Island canal front pool home with private dock. Located just 3 blocks from the beach, this spacious and recently renovated home boasts two master suites and comfortably sleeps eight. Just steps to free island trolley and two blocks from shops and restaurants. Other... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Located on beautiful canal front property on Anna Maria Island’s exclusive Key Royale, 610 Hampshire Lane is the perfect spot for a Florida vacation. This lovely renovated home offers four bedrooms, three full bathrooms and a powder room all nestled between the ninth hole of the Key Royale golf... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    The casual and spacious Anna Maria Island vacation rental “North Beach Village 67” is a fabulous way to make your vacation amazing! Just two blocks from the Gulf of Mexico’s best beaches, this town house style vacation rental has 3 bedrooms, 2.5 bathrooms, and accommodates up to 6 guests with 1... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Welcome to Palm Isle 3210, a one bedroom and one bathroom villa in the heart of quiet, friendly Holmes Beach on Anna Maria Island. Honeymoons, couples escapes, and smaller family vacations are just waiting to happen.  (1) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 King, 1 Sleeper... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3.5 of 5 bubbles (3) Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Just one short block away from the pristine water of the Gulf of Mexico and Anna Maria Island's gleaming white sand beaches, this two-bedroom, one-bath vacation rental has been updated inside and out for your vacationing pleasure. A well-appointed kitchen and outdoor grill may entice you to create... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Garden Home, located at 419 Clark Drive in Holmes Beach is a spectacular, three bedrooms, and two-bath pool home. This beauty is hidden among tropical gardens, ensuring a private, tropical vacation getaway. Nothing was spared in the recent renovation to this home! Its 2600 square feet of... View all property information
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    Holmes Beach, Anna Maria Island 34218
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    Castnetter Beach Resort #5 is a delightful Anna Maria Island rental located directly across the street from the seven acre Manatee Public Beach and the Gulf of Mexico. This beautiful and totally renovated two bedroom two unit sleeps six with a queen size bed in the master suite, two twin size... View all property information
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    Holmes Beach, Anna Maria Island 34218
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    AquaBella is a delightful architecturally designed canal front home that offers 3 bedrooms and 2 full bathrooms. This U-shaped home was constructed to take full advantage of the many tranquil views of the deep water canal and lush tropical landscaping. As you sit with your morning tea or coffee... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    About this property
    The Hideaway, located at 5002 5th Avenue in Holmes Beach is a gulf front home which will take you back in time when living was easy. This wonderful home was built in the 1940’s and still has the same charm and ambience of days gone by. Magnolia wood walls and ceilings throughout the home give the... View all property information
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    Holmes Beach, Anna Maria Island 34218
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    Gorgeous town house style Anna Maria Island vacation rental “North Beach Village 40” will be the memorable vacation spot that makes you absolutely fall in love with the island life! This stylish three bedroom two and half bathroom home accommodates up to six guests with two queen beds and two... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    (3) Bedroom, (3) Bath (Sleeps 6) – “LaMedeira”- 305 64th St unit A in Holmes Beach. “LaMedeira” is a stylish Anna Maria Island vacation rental home sure to make your dream getaway luxurious and memorable! No details were overlooked in the design of the sleek and comfortable blue white and... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Welcome to Seaglass!! This home was completely remodelled from the ground up, so everything is new. The designer decor is sophisticated, yet fun and perfect for the island atmosphere.  The new kitchen with granite counters, and beautiful stainless steel appliances is equipped with indoor and... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Turtle Cove is a little home away from home in paradise! This updated oasis is a peaceful and sunny stroll from the Gulf of Mexico and our flour soft, sugar white beaches. The unit next door is also available for rent, making it perfectly suited to multifamily traveling, reunions, wedding... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to Blue Lagoon!  This complex has one of the best community pools on the island!  Large, tropical pool with a 10' waterfall right outside your back door. The lovely upgraded kitchen offer granite countertops, stainless appliances and ample counter space for prepare meals or just... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. This one bedroom one bath unit is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to shopping,... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    The Cove at Sandy Pointe #202, at 3601 East Bay Drive is a cheerful, two bedroom and two bath condo in a secluded complex close to shopping and conveniently located to the beach. Sandy Point features undercover parking and a large heated pool. Each unit has a large screened lanai. This well... View all property information
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    Holmes Beach, Anna Maria Island 34218
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    Sea Pirate Condo #7, located at 3301 Gulf Drive in the heart of Holmes Beach is just a stone's throw from the tropic teal waters of the Gulf of Mexico. Situated in a much desired area, close to shopping and restaurants, this smaller complex features a large, screened and heated pool, on site coin... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedroom/2 Bath Villa, with its own Backyard, PRIVATE Heated pool, and only 75 yards to the beach! Beautiful new granite countertops, stainless appliances, and tile throughout. King Master bedroom with TV, Queen Bedroom w/ TV, Full/Twin bunk in the third bedroom with TV, and a full size Sleeper... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Your perfect place to stay when visiting Anna Maria Island. This property has a heated pool and it's just a 1 minute walk to the white sand beach at the Gulf of Mexico. The house can accomodate up to 7 persons and has two parking lots directly in front of the house. You have a private heated... View all property information
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    Holmes Beach, Anna Maria Island FL 34217
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    Beautifully renovated tropical paradise for your holiday getaway.Private heated pool, free wireless internet, pet friendly (up to 25lbs) with fee, less than two blocks from the beach. Appletini is an all new beautifully renovated duplex only a short 5 minute walk to the beach. This property... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    “Beachy Villa Vista” is a fantastically comfortable luxury Anna Maria Island vacation rental home accommodating up to 10 guests in tropical paradise. This stylish 5 bedroom 4.5 bathroom home offers 1 King bed, 2 Queen beds, 2 Twin beds, 1 Twin bunk bed and 1 Queen sleeper sofa. “Beachy Villa... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Visit this marvelous private custom-built vacation rental home just a few steps from the white sandy beaches of Anna Maria Island and the Gulf of Mexico. 6 Bedrooms, 4.5 Bathrooms, accommodates up to 14 people. 2 King beds, 1 Queen bed, 4 Twin beds, 2 Queen sleeper sofas, one in a private bedroom... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    HEAT POOL, SPA, BIKES AND BEACH GEAR FOR YOUR USE This stunning brand new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    This two bedroom, two bath Direct gulf frontvacation condo gives room for four guest to enjoy the Gulf waves crash in the distance while a little bit closer you can spot the shimmering, heated community pool. Lounge chairs and umbrellas offer shade and sun, whatever you poolside preference might... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    When you arrive at Anna Maria Island vacation rental home “Mermaid Crossing” you are greeted with true island style and luxury. This three bedroom three bath room home spaciously accommodates up to six guests with one king bed, two queen beds and endless charm. Located in the central area of the... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedroom, 2.5 Bath (Sleeps 8) - “North Beach Village” - 6250 Holmes Boulevard unit 27 in Holmes Beach. For a relaxing and fun Anna Maria Island vacation for up to eight guests, reserve North Beach Village unit 27! This Holmes Beach vacation rental townhome is the perfect island style escape... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Fountain Head Condominiums sit only a few properties to the azure blue waters of the Gulf of Mexico. All you need do is get comfortably into the island frame of mind. (2) Bedroom, (2) Bath, accommodates (6) people: 1 Queen, 2 Twins, 1 Sleeper sofa. Recent renovations include new tile floors,... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Key Lime Cottage East, 3 bedroom 2 bath new duplex with private heated pool.  Sleeps up to 6. Key Lime Cottage East welcomes you to this recently re-done and updated island duplex. Just steps from the Gulf of Mexico and the pure white sandy beaches of Anna Maria Island. All new furniture and... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    The Cove at Sandy Pointe #208, at 3601 East Bay Drive is a cheerful, two bedroom and two bath condo in a secluded complex close to shopping and conveniently located to the beach. Sandy Pointe features undercover parking and a large heated pool. Each unit has a large screened lanai. This well... View all property information
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    Holmes Beach, Anna Maria Island 34218
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      Luxury is here in this brand new direct gulf front three bedroom and three full bath Anna Maria island luxury holiday rental. Relax your cares away in the master suite fit for royalty, dual headed shower with massage jets and a Jacuzzi tub. Each bedroom has it's own private bath.Outdoor living... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Refreshing and tropical are the perfect ways to describe this vacation rental home Mango Breeze at 141 50th Street! Spend a week here in Holmes Beach and get the taste of island life on your tongue. Spend a beach holiday on Anna Maria Island in 2,500 feet of style and luxury. There’s room for... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Cast Away #2, located at 4101 Gulf Drive in Holmes Beach is a delightful condo situated conveniently across from the Manatee Public Beach and the shimmering Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and... View all property information
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    Holmes Beach, Anna Maria Island 34218
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Air Conditioning
    • Grill
    • Parking
    • Hot Tub
    • Balcony
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Beachside is a custom built three bedroom, three bath home located at 113 31st Street in Holmes Beach. This spectacular home is west of Gulf Drive for easy beach access with no busy streets to cross. There is a wonderful heated, salt water pool and spa for your use. The pool area is tropical... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
    • Terrace
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located on gulf front property, “Sun Plaza West” is a beautiful beach side Holmes Beach vacation rental home perfect for 4 guests! Well equipped with everything you need for a beach vacation this 2 bedrooms and 2 bathrooms second floor condo style vacation rental has 1 king bed and 2 murphy twin... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Patio
    • Parking
    • Satellite TV
    • Air Conditioning
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    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Location, location, location, this cozy quaint beach house is centrally located on Anna Maria Island and is less than a 2 minute walk from Holmes Beach. The 1 bedroom and 1 bathroom studio unit is not only a very short walking distance to the beach, but is also a short walking distance to shopping... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Grill
    • Terrace
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Casa Sierra Resort is a private Mediterranean style four unit complex in Holmes Beach on beautiful Anna Maria Island. This small quiet complex is just a two minute walk to the beautiful white sand beach! This ground level unit offers an outdoor patio with the spacious common area providing a... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Grill
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    • Washer
    • Internet Access
    • Shared Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Cast Away located at 4101 Gulf Drive in Holmes Beach is a delightful condo situated conveniently across from the Manatee Public Beach and the shimmering Gulf of Mexico. These two bedroom and one bath units sleeps six each with a queen size bed, two twin beds and a sofa bed. A full size kitchen... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Shared Garden
    • Washer
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Palm Cay Condominium #5 located at 3000 Gulf Drive in Holmes Beach is a very spacious three bedroom, two bath town home located west of Gulf Drive for easy beach access. The complex features a very large heated pool and onsite laundry room. The complex is about one half block to the beach and is... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Internet Access
    • Washer
    • Shared Garden
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Alamanda Villas, located at 102 39th Street in Holmes Beach is a charming beachside complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area. Anna Maria's white sandy beaches and the emerald green water of the Gulf of Mexico are just... View all property information
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    Holmes Beach, Anna Maria Island 34218
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Welcome to Blue Lagoon!  This complex has one of the best community pools on the island!  Large, tropical pool with a 10' waterfall right outside your back door! The lovely upgraded kitchen offer granite countertops, stainless appliances and ample counter space for prepare meals or just... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Air Conditioning
    • Parking
    • Shared Garden
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Alamanda Villas, located at 102 39th Street in Holmes Beach is a charming beachside complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area. Anna Maria's white sandy beaches and the emerald green water of the Gulf of Mexico are just... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to Turtle Nest just a short walk to the Gulf of Mexico and the sugar sand beaches of Holmes Beach. This vacation rental duplex has everything to offer with two bedrooms, kitchen, 2 bathrooms ,TV's in each room and all the comforts of home.The cozy decor is tasteful, fun and perfect for... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Internet Access
    • Air Conditioning
    • Grill
    • Balcony
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    3 Bedroom, 2.5 Bath (sleeps 6) - "La Casa Leann" – 7318 Gulf Drive La Casa Costiera unit 9 in Holmes Beach. Fall in love with tropical paradise when you visit Anna Maria Island vacation rental condominium “La Casa Leann”. This 3 bedroom 2.5 bathroom condo style raised home accommodates up to... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217