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Holiday Rentals in Holmes Beach

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    Travellers to Holmes Beach are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 30
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Casa Sierra Resort is a private Mediterranean style four unit complex in the heart of Anna Maria Island with just a two minute walk to the beautiful white sand beach! Each unit offers an outdoor patio with the spacious common area providing a large heated pool, gazebo, lush tropical landscaping,... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 46
    4 Bedrooms, 4 Bathrooms, Sleeps 16 | 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... View all property information
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    Holmes Beach, Anna Maria Island 34218
    1 / 15
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Just steps from the beach!! This 2 bedroom Gulf side townhouse has been completely remodeled & exquisitely decorated!! We are just 120 steps (1 minute walk) from the beach with no streets to cross and within walking distance of many shops and restaurants. The unit sleeps 4 in 2 large upstairs... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 44
    5 of 5 bubbles (2) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Beautiful, Brand New, 5 bedroom/3.5 bath Waterfront home with Heated Pool, Hot Tub, Dock, and just over a block to the beach! Covered Patio by pool area and peeks of the Gulf and Bay from the top patios. Great location in a quiet neighborhood, a few steps to the Trolley Stop, and a short walk to... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 33
    5 of 5 bubbles (7) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Coastal living in a tropical setting! Gorgeous ground level 3 bedroom/3 bath home with designer touches at every glance. This light and airy, open-concept floor plan is generously appointed with flat screen TVs in all rooms and tile floors throughout every one of its almost 2000 square feet. You... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 40
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Beautiful, brand new, 5 bedroom/3.5 bath home with large privacy fenced lushly tropical landscaped yard, heated pool, hot tub, elevator, and ping pong table! There is large covered patio by the pool area with outside dining options and plenty of seating in the large great room area. The kitchen... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 34
    4.5 of 5 bubbles (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    There's no better way to enjoy Anna Maria Island than Sand Dollar! Centrally located in a mellow, residential neighborhood, Sand Dollar is a half block to the free Island trolley and a quick 6 minute walk to the beach 3 blocks away. Also in close proximity are many of the Island's best eateries.... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
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    1 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2 Bedroom/2 Bath updated condo in a great central Holmes Beach location, and just a few steps from the beautiful white sand beach! There is a Queen in the master with a TV and ensuite bath and Queen in the second bedroom with TV. Amenities also include Heated pool, Washer/Dryer, Cable TV, DVD, High... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Stunning canal front Anna Maria Island vacation rental home “3 Oars” is the perfect destination for your next luxury getaway! With everything you expect from a fun and relaxing vacation, “3 Oars” has it all! Spaciously accommodating up to eight guests with four bedrooms and four bathrooms no... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    4.5 of 5 bubbles (8) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    At first glimpse, Happy Heron will make you smile! Just one short block away from the pristine water of the Gulf of Mexico and Anna Maria Island's gleaming white sand beaches, this one-bedroom, one-bath vacation rental has been updated inside and out for your vacationing pleasure. When renting... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Seabreeze Villa is a fabulous home for your vacation on Anna Maria Island. This beautiful Mediterranean designed home is located in central Holmes Beach, and is within walking distance of shopping, restaurants, and the white sand beach! This spacious home is equipped with a fantastic kitchen,... 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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    About this property
    The perfect place for a fun filled memorable vacation destination is waiting for you at the vacation rental home “Summer Breeze”! This gorgeous five bedroom three and a half bathroom home accommodates up to 10 guests with two king bed, one queen bed, two twin beds and a queen sleeper sofa in the... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Cute and updated cottage with a beautifully landscaped private backyard, PRIVATE Heated pool, paver deck, fully stocked kitchen with Granite countertops and Stainless Steel appliances. The Living Room is outfitted with very comfortable furnishings to make you feel right at home! Your family will... View all property information
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    Holmes Beach, Anna Maria Island 33704
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    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... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Please note: Pets allowed under 25lbs. There is a non-refundable pet fee of $150 per pet for this property that will not be reflected in online pricing. Find the perfect Anna Maria Island vacation rental in Holmes Beach when you visit “Palm Paradise”. This canal front rental is just minutes from... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 22
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
    About this property
    A dream come true holiday oasis perfect for large families. (6) Bedrooms, (4.5) Bath, accommodates up to (16) people: 4 King, 1 Queen, 2 Twin, 2 Sleeper Sofa. Private heated pool with spa, outdoor kitchen, free wireless, pet friendly with fee, less than two blocks to the beach. New Luxury... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 40
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Very spacious 4 bedroom/3 bath home, just a short block to the beach (just over 100 yards), and a couple houses to the free Island trolley! Beautifully tropical landscaped back yard with a Heated Pool surrounded by a large paver deck and plenty of seating options. Huge open Living/Family Room area... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
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    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Beachside Palms 3, located at 4104 4th Avenue in Holmes Beach is a delightful island locale located directly across the street from the seven acre Manatee Public Beach and the Gulf of Mexico. This beautiful and totally renovated one bedroom unit with one bath sleeps four with a queen size bed and... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Fountainhead Condo #4, located at 3402 6th Avenue in Holmes Beach is just a few steps from the beautiful beaches and emerald green water of the Gulf. This eight unit complex has a heated pool and laundry room on site. This unit is beautifully furnished and well equipped for your enjoyment. The... View all property information
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    Holmes Beach, Anna Maria Island 34218
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    (4) Bedroom, (4) Bath (Sleeps 8) – “Beachy Blue”- 129 52nd St in Holmes Beach. “Beachy Blue” is a magnificent Anna Maria Island vacation home that will make your vacation feel truly luxurious! This spacious rental home offers accommodations for up to 8 guests including 4 roomy bedrooms with 1... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Cayman Cay Condo #109 located at 4307 Gulf Drive in Holmes Beach, is a very comfortably furnished and recently updated ground level unit in a smaller complex, just a few short steps to the beach. Cayman Cay offers a heated pool, and every amenity to make your stay here a comfortable one. After a... View all property information
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    Holmes Beach, Anna Maria Island 34218
    1 / 69
    8 Bedrooms, 4 Bathrooms, Sleeps 20 | Quick View
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    About this property
    Welcome to the Garden Villas at 301 - 307 42nd Street in Holmes Beach. This delightful island locale is situated conveniently across from the Manatee Public Beach and the Gulf of Mexico. Walk to the Cafe on the Beach, West Coast Surf Shop and the nearby Island Centre Shopping which serves all of... View all property information
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    Holmes Beach, Anna Maria Island 34218
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Holmes Beach, Anna Maria Island 34218
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Welcome to the laid back Anna Maria Island vacation rental you’ve been looking for! When you visit “Blue Palm” you’ll know you have found a great place to relax island style. You’ll be a short two blocks walk from the best gulf beaches Florida has to offer on this memory maker vacation.... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    “Vitamin Sea” offers fabulous amenities for up to eight guests with four bedrooms and 3 bathrooms all just a short walk to beaches, free trolley stops, shopping and DINING. This Anna Maria Island vacation rental is the perfect place to gather family and friends for a memorable holiday with no... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 18
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Anna Cabana Bungalow #1 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... View all property information
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    Holmes Beach, Anna Maria Island 34218
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    A Wright Place, located at 6803 Holmes Blvd., is a comfortable two bedroom, two bath duplex with poolside den which can easily serve as a third bedroom. It's exactly what you are looking for in a peaceful Anna Maria Island retreat. Located in a quiet, lakeside residential neighborhood, this unit... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 28
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
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    About this property
    Direct across street from our unit at Gulf Sands. Both units use the same pristine Beach... Over 700 ft of Beach less than 100 yards away. Recently decorated lovely Pool and Barbecue Area.Spacious pool area with shaded area Bedrooms are private as well as bathrooms. rooms do not open into LV.... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 17
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    Coral Cottage is a newly renovated 2 bedroom, 2 bathroom bungalow which includes its own private heated pool nestled in lush tropical landscaping. The white sand beaches are only a short 2-3 minute wEarle Master bedroom and a Queen bed in the second bedroom. There also is a Queen pull-out sleeper... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 39
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Unit 205A, Cove at Sandy Pointe, at 3601 East Bay Drive is a bright and airy 2 bedroom, 2 bath condo in a private and peaceful complex located a short walk to the beach (8 minutes) , shopping (5 minutes), and free public transit. It features cathedral ceilings, recently updated kitchen and baths... View all property information
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    Holmes Beach, Anna Maria Island 34218
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Experience a glamorous Anna Maria Island vacation rental home when you stay at 623 Ivanhoe Lane. Nestled in between the fifth hole of Key Royale Golf course and Bimini Bay 623 Ivanhoe Lane is in the most coveted area of Holmes Beach. This Luxury ground level, 3 bedroom, 3 bathroom Anna Maria... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Franks Beach House is a beautiful three bedroom, two bath direct Gulf front home located at 3212 Gulf Drive in Holmes Beach. It features a very large open deck facing the beach as well as a screened lanai for when you want a little shade. The expansive beach stretches for miles in either... View all property information
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    Holmes Beach, Anna Maria Island 34218
    1 / 27
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy a laid back tropical paradise vacation when you visit Anna Maria Island vacation rental “Catchin’ Rays”. Just a short block to Gulf of Mexico beaches, “Catchin’ Rays” is the perfect beach vacation destination for up to eight guests. This easy going home offers everything you and your... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    The Serenity is a custom built four bedroom, four bath pool home located at 2914 Avenue E in Holmes Beach. Just one house from the beach, the Serenity has sweeping views of the Gulf of Mexico from the master bedroom suite. Additional features include tile and natural wood floors throughout,... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    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 four with a... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    1 / 20
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Satellite TV
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This beautiful 3 bedroom 3 bathroom Bungalow is only a short walk from the white sands beach of Anna Maria Island. Around the corner from the nearest free trolley stop. You can explore all the beauty of the island or just spend the day relaxing in our own backyard oasis. This is one of the best... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The quintessential Florida beach side condo, you’ll love your Anna Maria Island vacation when you stay at West Winds 6828. This fun and tropical inspired coastal getaway accommodates up to four guests with two bedrooms and two full bathrooms. Nestled in the West Winds community on the Gulf of... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Air Conditioning
    • Washer
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    • DVD Player
    • Shared Garden
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Jukes Beach House is a charming, gulf front home located at 102 34th Street in Holmes Beach. This ground level home is conveniently located close to shopping and restaurants and on a pristine, wide expanse of beach. What could be better? This is a new and affordably priced gulf front home that... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    1 / 38
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • DVD Player
    • Satellite TV
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    • Washer
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Huge 4 bedroom/3.5 bath home, just a short block to the beach(just over 100 yards), and a couple houses to the free Island trolley! Beautiful back yard with Heated Pool. Large Master Suite upstairs with private deck Sleeps up to 8. 2830 sq. ft. 210 67th 4 Bedroom/3.5 Bath/House Rates from... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 40
    5 of 5 bubbles (2) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Patio
    • Hot Tub
    • Private Outdoor...
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Welcome to the ultimate in large family luxury vacation homes, with peeks of the Gulf of Mexico from the balconies! This 6 bedroom/4.5 bath beauty features a large, private, tropically landscaped backyard with heated pool and hot tub, gas grill, swim up tiki, and covered tiki bar area with flat... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 39
    3 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Terrace
    • Air Conditioning
    • Balcony
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    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Bollinger Duplex is a very comfortably furnished and spacious duplex located at 6909 Gulf Drive, in the preferred, quiet area of northern Holmes Beach. This property is located about one-half block to the beautiful Gulf of Mexico where you can walk for miles in either direction on the white,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    La Plage 2 is island luxury at its best, one of the largest 4 bedrooms and most luxurious beachfronts. An exquisite example of Mediterranean architecture nestled right on the sands of the Gulf of Mexico, this beachfront enclave will exceed all your expectations. Relax in the tropical splendor of... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Satellite TV
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Two bedroom, two bath condo in the quiet, four-unit complex of Seabreeze! Clean and Comfortable! Nicely appointed kitchen with Stainless Steel Applicances. Conveniently located for shopping, restaurants, and the beach, yet tucked back into a quiet area! Just a block to Skinny's for the Best Burger... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Terrace
    • Internet Access
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    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    North Beach Village 69 is the perfect Florida beach side vacation destination. Sleeping up to six guests this townhouse style Anna Maria Island vacation rental is in a great location. Not only is this home close to beaches, shopping and dining, but it offers great comfortable coastal style.... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 23
    4.5 of 5 bubbles (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Spinnakers Vacation Cottages, Captain's Quarters is surrounded by lush tropical landscaping, close to everything but with a feeling of being tucked away! This lovely vacation rental is located in Holmes Beach and is just 250 steps to the beach! Spinnakers is made up of four cottage-style... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 47
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Shared Garden
    • Internet Access
    • Parking
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    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The Pool Party, located at 314 61st Street in Holmes Beach, is a beautiful duplex featuring two bedrooms and two baths on each side with a pool area that is unsurpassed! This property features a heated pool with a spa surrounded by mature, native plantings as well as a shaded hammock and an... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    1 / 30
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The large heated pool and nestled right in the sands of the Gulf of Mexico beaches. Enjoy a sunset right on your direct gulf front enclosed lanai. This unit accepts a one month stay or longer. (2) Bedroom, (2) Bath, accommodates up to (4) people 2 Kings. There are so many island activities at... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217