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Holmes Beach Holiday Homes

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    Travellers to Holmes Beach are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    5 of 5 bubbles
    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Waters Edge Condo 210S is a gorgeous two bedroom, two bath direct Gulf front unit, located at 5806 Gulf Drive in Holmes Beach. This much sought after complex features an elevator, heated pool, tennis court and a beach that is unparalleled. The open balcony is directly on the beach and will...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 11Quick View
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    Welcome to the SS Salamander located at 121 50th Street in Holmes Beach. This recently updated duplex 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 walking distance to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    2 Bedrooms, Sleeps 6Quick View
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    2 Bedroom, 1 Bath (sleeps 4-6) - "Playa Casanas South" - 3222 Gulf Drive unit A in Holmes Beach. “Playa Casanas South” is a wonderful vacation rental home directly on the sparkling white quartz sands of the Gulf of Mexico. Sleeping up to six guests comfortably in two bedrooms and one bathroom...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick 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...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Recently updated, find the casual and relaxing Anna Maria Island paradise getaway you’ve dreamt of at North Beach Village 55. This three bedroom two and a half bathroom townhome Anna Maria Island vacation rental nicely accommodates up to six guests in island style comfort. Feel relaxation...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    3 Reviews
    5 Bedrooms, Sleeps 10Quick View
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    • Private Outdoor Pool (Heated)
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    • Ocean Views
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful 5 bedroom 4 bathroom vacation home in Holmes Beach, just steps from the beach with fantastic Gulf views. This home is the perfect beach getaway with everything you could want while enjoying Anna Maria Island. Just imagine waking up to the sound of the surf rolling in. Enjoy a cup of...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, Sleeps 4Quick View
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    About this property
    Direct gulf front one bedroom and one and a half bath condo in desirable Water's Edge complex which is the best place for a holiday rental. Enjoy the large heated pool and just steps to the Gulf of Mexico. Whether you stay a week or a month this is the perfect condo for a winter retreat,...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time sun is setting on your first day, most people are hooked. But when you pull up the east side of this elevated vacation home at 131 White Ave, it might be good old fashioned love at first sight....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    28 Reviews
    3 Bedrooms, Sleeps 4Quick View
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    • Balcony
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    About this property
    TripAdvisor EXCELLENCE AWARD | Exquisite direct beachfront condo with 2 ensuite bedrooms, den, and 2 baths | Stunning views | Sleeps 4 | Open kitchen | Granite counter tops | Large storeroom at beach level with beach furniture | Beach side screened lanai with stairway direct to beach | Ceiling fans...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    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...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 of 5 bubbles
    2 Reviews
    6 Bedrooms, Sleeps 12Quick View
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    About this property
    529 Key Royale - Private canal home 6 Bedroom / 5 Bath with private pool , maximum occupancy of 12 people. Outstanding large home perfect for a family! This beautiful Florida pool home is on a canal offering 6 bedrooms- 5 bathrooms . Luxury at its best! Sip your coffee in the morning on the...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    2 Bedrooms, Sleeps 4Quick View
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    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...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Shared Garden
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    Pet friendly
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    Smoking allowed
    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...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    Accommodates up to (4) people: 1 Queen, 2 Twins. Shared heated pool, free wireless, sorry no pets allowed, across the street from the beach. We’re not afraid to say that all you really need for a great holiday in Holmes Beach is somewhere to sleep and wash the sand off. From the first...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    When you’re looking for a vacation home on Anna Maria Island that blends comfort, luxury, and fun, you’re looking to spend your week in Holmes Beach at Gulf View Townhomes unit 4. There is room for up to six guests, spread out across 2 bedrooms and 2.5 bathrooms to enjoy the vibrant island views,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    The right company can be a retreat all in themselves. When you’re looking for an escape in Anna Maria Island with someone special, consider a week spent at PIV3215 in Holmes Beach.  (1) Bedroom, (1.5) Bathroom, accommodates up to (4) people: 1 King, 1 Sleeper sofa. You’ll have plenty of...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, Sleeps 2Quick View
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    • Private Garden
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    Pet friendly
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    About this property
    Carissa Coastal Beach Cottage has just been updated with everything you need for your stay, and has a Great Location, only 150+/- steps to the Sugary White Sand Beach! Carissa Cottage has "beachy" decor, nice size living room space with large sofa sleeper and two additional comfy chairs, Flat...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, Sleeps 4Quick View
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    It was Holly Golightly, as played by the immortal Audrey Hepburn, that once looked off into the distance and sighed, “Calms me down right away. The quietness and the proud look of it nothing very bad could happen to you there. If I could find a real-life place that'd make me feel like...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    2 Bedroom, 2.5 Bath (Sleeps 6) - “North Beach Village” - 6250 Holmes Boulevard unit 63 in Holmes Beach. You will love spending time with friends and family during your Anna Maria Island getaway when you spend a week at North Beach Village 63! This two bedroom, two and a half bathroom...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Peaceful Palms is more than a vacation rental, it is a slice of island life that you can call you own. Ease into your home away from home by pulling up swaying palm trees and charming, well maintained landscaping in the front yard. You’ll be getting into that Florida frame of mind as soon as you...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    2 Reviews
    5 Bedrooms, Sleeps 10Quick View
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    • Shared Outdoor Pool (Unheated)
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    About this property
    532 70th - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. Our Sandsational family home!~ Would you care to escape to Florida with style and sophistication? Indulge friends and family while pampering yourself vacationing at this elegant residence...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    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...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Nautilus Complex is directly on the Gulf of Mexico and has the best beaches on the West coast of Florida. Unit 105 is a ground level 2 bedroom 2 bathroom condo and it has everything you need to make that special vacation one to remember.  (2) Bedroom, (2) Bath, accommodates (4) people: 1...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    The Gulf-front Bradenton Beach Club condo is located at 1700 Gulf Drive, and features a spa, two heated pools, an elevator, and bayside gazebo. This spacious condo has panoramic beach views from your living room, balcony and master bedroom. Across the street on the bay is a boardwalk through a...
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    Holmes Beach, Anna Maria Island 32417
    Condo/Apartment - 3 Bedrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Direct gulf front two bedroom and two bath condo in desirable Water's Edge complex which is the best place for a holiday rental. Enjoy the large heated pool and just steps to the Gulf of Mexico. Whether you stay a week or a month this is the perfect condo for a winter retreat, vacation rental...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    The Blanco unit, located in Sunset Villas #2, at 3009 Avenue E in Holmes Beach is a totally renovated condo in a quiet area, and just a few steps from the Gulf of Mexico beaches! This beautiful two bedroom, one bathroom ground level unit is decorator furnished with a tropical flair and with...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Anna Maria Island's chic upscale development offers this ground level, vacation cottage at called Sunfish Cottage! Every detail has been taken care of with our guest's relaxation in mind. (2) Bedroom, (2) Bath, accommodating up to (4) people: 1 King, 1 Queen. You’ll have the comfort of high...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    About this property
    The Valhalla downstairs unit, located at 3216 Gulf Drive in Holmes is a wonderful two bedroom, one bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! The large...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Plum Cottage 322 is professionally decorated with a laidback island flavor, and offers everything you'll desire for a truly memorable vacation! This single story, candy colored rental is directly in the heart of Anna Maria Island. Get on beat with plenty of island flavor as you’ll be close to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    Lush tropical landscaped setting. Beautifully maintained two bedroom vacation rental on gorgeous Anna Maria Island. Secluded beaches, shopping, restaurants, golf, fishing and relaxation. Apartment includes full kitchen, 50' flat screen TV in living room, flat screen TV also in one of the two...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Smoking allowed
    About this property
    All of the Palm Isle Villages are a good choice for family vacations.  But PIV 3206 is particularly perfect for vacations with kids thanks to a charming set of bunk beds in the guest bedroom.  (2) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 Queen, Set of short bunk beds, 1 Sleeper...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Welcome to Sun Ray 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 the...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The decor inside of 5613 Gulf Drive is tasteful and with a nod to old Florida sensibilities. The gulf coast themed artwork echoes natural beauty found all around Anna Maria Island. Rich hardwood floors upstairs and ceramic floors downstairs spread out across two bedrooms, two bathrooms, and a...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Kid friendly
    Smoking allowed
    About this property
    Relax and unwind in the casually luxurious Anna Maria Island vacation rental home “Sapphire Beach House”. This four star rental has everything experienced vacationers look for in a home from the perfect location to well-appointed amenities. Just two blocks from the powder sand beaches of...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    “Hideaway” is a fantastic Anna Maria Island vacation rental in Holmes Beach offering space for up to six guests just a few blocks from the beach. During your stay you’ll find everything you need for a laid back island getaway. Inside this Holmes Beach rental you’ll enjoy updated decor with a...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
     2 Bedroom, 2 Bath (sleeps 6) - 202 78th Street - Holmes Beach A perfect beach is one where all you need is a bottle of sunscreen and a towel. All you need to relax is somewhere beautiful to get away from your stressors. (2) Bedrooms plus loft, (2) Bath, accommodates up to (6) people: 1...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Air Conditioning
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The cottages at Palm Isle Village are some of the finest and most favored vacation properties on Anna Maria Island. We are always very proud to recommend them to our vacationers and no one can say it isn’t a special place to spend quality time with friends and family. With so many indulgent,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    • Shared Garden
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    Smoking allowed
    About this property
    Sirena del Mar is a three bedroom, two bath home located at 201 30th Street in Holmes Beach. This home has been totally renovated and features a small pool. Its two very short blocks to the wonderful, white sandy beaches. Sirena del Mar has a wonderful open design with all new kitchen cabinets...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “La Mer” is a lovely destination for a fun and relaxing Anna Maria Island getaway. This stylish home comfortably sleeps up to six guests with fantastic amenities just a short stroll to gulf beaches. When you visit “La Mer” you’ll find everything you want from an island vacation including a...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Kid friendly
    Smoking allowed
    About this property
    Plum Cottage 324 is professionally decorated with a laidback island flavor, and offers everything you'll desire for a truly memorable vacation! This single story, candy colored rental is directly in the heart of Anna Maria Island. Get on beat with plenty of island flavor as you’ll be close to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The right company can be a retreat all in themselves. So when you’re looking for an escape in Anna Maria Island with someone special, consider a week spent at PIV3211 in Holmes Beach. There is room for only two people at this one bedroom, one and half bathroom vacation cottage with a king sized...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    • Terrace
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    611 Gladstone - Private home 4 Bedroom / 3 Bath with private pool , maximum occupancy of 6 people. This very spacious four bedroom and three bath home is located in the quiet yet very popular Key Royale community. Just a short stroll to the beach, shopping, restaurants or the library. It features...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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