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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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Anthony Beach Cottages Island Retreat1 / 26
    (5)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    510 Bayview1 / 20
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    510 Bayview - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. Island Elegance for the whole family!~ Distance to the Beach: 2 blocks Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Spectacular Beach House With GulfView Only Steps to a Pristine Beach1 / 13
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Spacious 3-level House with 2 large decks overlooking the beautiful Gulf of Mexico. House is fully furnished with a large flat screen TV and Bose Stereo System. Great Gulf views from living room and Master Bedroom. One Guest room also has a gulf view. Large garage is fully equipped with beach...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    Two bedroom two bath condo located upstairs in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 6 to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    The Anna Maria Island Beach Retreat is a completely remodeled two bedroom one bathroom condo, located four houses from Anna Maria Island’s exquisite white powder sand beaches. Included with your stay is one free breakfast for everyone in your party plus free daily beach chaise and umbrella rentals...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sunfish 104 Escape with your loved ones to some of the best beaches in Florida! Anna Maria Island's sunshine, soft sands, and charming sights all await you at this dog-friendly cottage, with a shared pool to keep you entertained at home. Wake up and start your morning right with a mug of warm...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The Anna Cabana Beach House is an adorable two bedroom, two bath home located at 3709 Gulf Drive in Holmes Beach. This quaint home has a large open deck with a great view of the beach. Watch the sunsets or enjoy the tropical landscaping on the large deck facing the Gulf. Numerous fruit trees and...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fully Remodeled Vacation Rental Anna Maria Island1 / 15
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Come relax and enjoy your beach vacation at The Dolphin Club! 2 bedrooms and 1 bathroom, the master bedroom has a queen bed and the other has 2 twin beds. There is also a sleeper couch in the living room which can sleep 2 people. Fully air conditioned. Includes covered parking and outdoor deck with...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The Anna Maria Island Beach Paradise 51 / 62
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! The Anna Maria Island Beach Paradise 5 condo is located directly in the middle of beautiful Anna Maria Island on Holmes Beach. This is a delightful location conveniently located across from the seven acre Manatee Public...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Garcia Home is a very comfortable and cozy two bedroom, two bath home at 3212 6th Avenue in Holmes Beach. It’s located in a quiet, residential neighborhood, close to the beach, restaurants and shopping. It has undercover parking and a washer and dryer. The Garcia Home sleeps six with a queen...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Lake by the Beach at 6806 Palm Drive offers the best of both worlds! This beautiful two bedroom, two bath home is situated on a spring fed lake yet it's only three blocks to the beach. New renovations include a brand new family room addition with easy access to the beautiful pool! A unique and...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Vista Grande 3 Penthouse Bask in the elegance of this three-bedroom Holmes Beach penthouse, a beachfront retreat with direct access to the sand, a wrap-around balcony with stunning Gulf views, and shared amenities that include a heated swimming pool, a patio, and a grilling area. Stunningly...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Come stay this beautiful 2 bed/2 bath condo at Water's Edge on Anna Maria Island. From the balcony you can see the Gulf of Mexico and beach. It is very nicely located as well of Gulf Dr in Holmes Beach not far from places to eat, activities and shops. The building is well maintained and you have...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Adam's Eden is less than two blocks to one of the island's best beaches. It’s located right in the middle of paradise at 2917 Gulf Drive in Holmes Beach. This private home is surrounded with lush tropical plantings and trees. It has three bedrooms and two baths. The living room, dining area and...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Welcome to the SS Salamander, South unit at 121 50th Street in Holmes Beach. This recently updated two bedroom and one bath unit is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's easily within...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    The Siboney located at 3700 Gulf Drive in Holmes Beach, is an exquisite, executive level home with a private heated pool set amidst tropical, native landscaping. Its 2000 square feet of luxury! The beach is approximately one half block away with no major roads to cross. You can enjoy views of the...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Anna Maria Beach Place #5, located at 201 35th Street in Holmes Beach is a charming beachside complex featuring six units surrounding a heated pool and tropical gardens. Immediately across a rarely traveled, dead end road are the white sandy beaches and the emerald green water of the Gulf of...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    About this property
    If you are looking to go away on a romantic vacation with a special person, this 1 bedroom, 2 bath unit is perfect! It has a king size bed, jacuzzi, and is literally right on beautiful Bradenton Beach. You can look outside your window and see the blue water of the Gulf of Mexico, while watching the...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The Beachside is a custom built three bedroom, two 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 and...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    MI Happy Place Island Resort - Sand Castle is a delightful Anna Maria Island locale situated directly across from the Manatee Public Beach. The MI Happy Place Island Resort (formerly Garden Villas) features new ownership and management with exciting amenities and upgrades that combine to make a...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Looking for a fantastic location? It doesn't get better than this ! Feel the stress slip away as you enter this island oasis. Centrally located on the island, this 2 bedroom, 2 bath condo sits right across from the sparkling gulf waters of Holmes Beach . Uniquely situated just south of Anna Maria...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Lakeside Beach House is a wonderful newly renovated three bedroom, two bath home with a private and brand new heated pool. Located at 6935 Holmes Blvd. in Holmes Beach, this lovely property is convenient to the beach and in a very quiet, Holmes Beach residential neighborhood. This home faces...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gulfsands Condo #201, located at 4200 Gulf Drive in Holmes Beach, is a beautifully furnished two bedroom, two bath condo directly on the beach. It’s in a popular Gulf front complex with a large heated pool, elevator and undercover parking. This complex is located adjacent to the Manatee Public...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Anna Maria Beach Place #3, located at 201 35th Street in Holmes Beach is in a charming beachside complex featuring six units surrounding a heated pool and tropical gardens. Immediately across a rarely traveled, dead end road are the white sandy beaches and the emerald green water of the Gulf of...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    A fun and relaxing vacation beckons at the Sea Turtle unit at MI Happy Place Island Resort! This unit features a classy Island Resort theme and colors, reflecting the warm glow of the beach. Start or end your day just relaxing with a drink on either of the two private decks. Like the MI Happy Place...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Beautiful open concept home. 3 king bedrooms with ensuites and a den with 2 single bunk beds makes this property perfect for multi-generational or multi-family vacations. This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Cabana Bungalow #4 located at 3711 4th Avenue in Holmes Beach is in a ground level five unit complex that’s fun and affordable. It adjoins three other of the Cabana Bungalow units and is next door to the Cabana Beach House. With the numerous room configurations this is a perfect complex for...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Welcome to the Sea Horse unit at MI Happy Place Island Resort! Fresh and fun, this recently updated unit features the clean, modern aesthetic of our other resort units blended seamlessly into the Old Florida quaint architecture. Roll out of bed and lounge on the sunny secluded deck as you get ready...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Coquina Sands, view beach from balcony, priv pool1 / 12
    (8)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    This is a gorgeous home, just 1/4 block from the beach which you can see from the balcony. Private elevator to all floors, relaxing living room with flat screen TV. Impressive Kitchen with granite counter tops, Stainless steel appliances, wood floors, bar sitting area, large dining room....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Coconuts Courtyard 119 Upstairs1 / 23
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Vacation in your own tropical sanctuary on Anna Maria Island. This 2 bedroom and 2 bathroom single family home is located on a quiet cul-de-sac and only steps away from the soft sand beaches of Anna Maria Island. Enjoy amazing sunsets at the famous picturesque Bean Point Beach only a short distance...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    The Absolutely Perfect Beach House, located at 3009 Avenue F in Holmes Beach is just that – absolutely perfect! This spectacular four bedroom, three and one half bath gulf front home with an extra media room. It has its own private beach and heated pool has just been built. This beautiful home is...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    The Sand Dollar unit at MI Happy Place Island Resort is a fantastic two bedroom, one bath unit that sleeps six. The updated Sand Dollar features comfortable beds, luxurious linens and an Island style relaxing decor throughout! With a queen, two twins, and a sleeper sofa with upgraded mattress, a...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Peace 'n Paradise, located at 5405 B Gulf Drive in Holmes Beach is a comfortable two bedroom, two bath duplex with a private heated pool and spa. Peace 'n Paradise will sleep six with a king size bed, two XL twins and a queen sleeper sofa in the living room with an upgraded mattress. It's exactly...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Relax and unwind in this gorgeous, newly renovated 2 bedroom, 2 bath home close to everything! Salt Air East villa, located only a short walk to the powdery white sandy beach of the Gulf of Mexico and ½ a mile from historic Pine Avenue on Anna Maria Island. Not in the mood for the beach? No...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coco Cabana located at 309 A 58th St in Holmes Beach is a beautiful three bedroom two bathroom home with a private heated pool. This ground-level home has everything you could want, just a few blocks to the beach, and close to shopping and dining. After a day at the beach come back and continue to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Bman Beach Cottage located at 2812 Avenue B in Holmes Beach is a cute 2 bedroom 2 bath private home. This ground level home has two screened lanais one overlooking the pool and Jacuzzi. The kitchen has been newly updated as well as one of the bathrooms. This property has long distance and WiFi...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    This 3 bed 2 bath island oasis will take you back to the days of old Florida charm but in a modern and well appointed setting. It is nestled away on a quiet street just a few minutes walk to the white sand beaches on the Gulf of Mexico. Located within walking distance to the award winning Beach...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Seabreeze Condo B, at 403 39th Street in Holmes Beach, is a very nicely furnished, well maintained, and comfortable two bedroom, two bath unit with a heated pool. This smaller complex is located just a few short steps to the beach and it's just a short stroll down a newly created path to, shopping...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Incredible 3 Bed 3 Bath bungalow, Minutes From The Beach With Backyard Oasis This beautiful 3 bedroom 3 bathroom Bungalow is only minutes from the white sands beach of Anna Maria Island. Only a minute walk to the nearest free trolley stop you can explore all the beauty of the island or just spend...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
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    Sprawling 3 bed 2.5 bath LUXURY Single Family Home with HEATED pool and ELEVATOR Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind! Crosswinds Cottage is just a short five minute walk to Anna Maria Island's world renowned white sandy...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    About this property
    Lovely 3 bedroom, 2 bath home with cozy furnishings. You and your guests can stretch out and relax in the living area, whip up delicious meals in the modern kitchen and enjoy the comfort of having your own private accommodations for an ideal getaway. Enjoy the additional amenities the accommodation...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Smoking allowed
    About this property
    This brand new 3 bedroom 3.5 bathroom + den . This home is 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 every luxury you could want, Flat screen...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for an island getaway without all the hassle? We’ve pretty much thought of everything, so you don’t have to. Whether you’re looking to relax or party it up — you found the right place. Located on Anna Maria island, best known for it’s pristine, wide stretching white beaches and relaxed...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Palm Cay Condominium #4 is located at 3000 Gulf Drive in Holmes Beach, on the west side of the street for easy beach access. You can walk to the beach is less than two minutes with no busy streets to cross. Palm Cay features a large heated pool and an on site coin operated laundry room for your...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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