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Casa Amiga by Beach Retreats Vacation Rentals 144 Crescent Dr. Anna Maria, FL 34216 City of Anna Maria | 4 Bedrooms | 4.5 Bathrooms | Sleeps 10 | Heated Pool + Jacuzzi | Rooftop Deck | Shared DockLuxury Island Living Near Bean Point Welcome to Casa Amiga, a beautifully designed 4-bedroom, 4.5-bath...
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Beachfront paradise awaits you at the TripleTail.Located in a prime location - just one block from Pine Avenue and the City Pier, the 4 bed/4 bath bayfront home offers everything you need for the perfect vacation.On the ground floor, you’ll find a beachfront king bedroom, along with a...
Distance to beach: 0.1 miles to Bayside Beach
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Newly renovated December 2024, with state of the art finishes! 5 King BR, 1 also has a Daybed + 2 King Sleeper Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep 14 total with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! 3 King Bedrooms...
Featured review
Fabulous location and spotlessly clean family villa with every conceivable convenience to hand. Fitted our purposes exactly and the addition of the kayaks, boat and bikes/golf cart if you wanted them was...
Distance to beach: 0.1 miles to 30 seconds to your left
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This newly redesigned elevated pet friendly 3 Bedroom, 2 Bathroom home is beautifully appointed throughout, with state of the art quartzite counter tops, stainless steel appliances and driftwood style hardwood floors and ceilings. Relax on the covered porch with direct views of the Gulf of Mexico and...
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Immerse yourself in all that Indian Shores has to offer at Mariner's Pointe, where there is something for everyone in the family to enjoy. This condo, located in a small, quiet building, features a spacious open floor plan with views of serene mangroves off the private balcony. The onsite dock provides...
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I have stayed in many condos and some have been nice while others were not so nice. This condo exceeded expectations on all accounts. Many extras were thought of and it was decorated beautifully. Everything...
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Come enjoy your own slice of paradise at Mariner's Pointe, a quiet pet friendly building on the Intracoastal surrounded by lush mangroves within a 3 minute walk to the beach. This condo features a spacious open floor plan surrounded by windows that spill of natural light during the day and serene...
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The unit we had at Mariners Point was perfect for our needs. It was quiet - off the beach but the walk was super short to get to the beach. The people we met-both owners and guests were friendly. The beach...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS!Welcome to your home-away-from-home! This 4-bedroom, 4 full bath, 2 half bath pet-friendly, canal-front retreat is made for making memories — whether you're here with family, friends, or your fishing crew. From sunrise to sunset, the views,...
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Please reach out for a quote or if you have any questions, we respond quickly. Welcome to Sol Y Mar! This bright, newly refreshed 3 Bedroom beach house oasis features the perfect mix of modern decor mixed with touches of mid-century inspired furnishings and original terrazzo floors. Guest will love the...
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Bring the whole family or your group to this bright and spacious 5-bedroom home in Largo, just minutes from Florida’s white sand beaches. With an open-concept kitchen, living, and dining area, a private backyard with BBQ, and easy access to shopping, restaurants, and entertainment, this home is...
Distance to beach: 50 feet to Indian Shores
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)My condominium is a direct ocean front three bedroom two bathroom with no obstructions and is located on the sixth floor. Easy convenient minivan rental is also available at tampa airport or Clearwater/Saint Petersburg. I also own two other similar condos such as these. Our Mini vans economical, seat...
Featured review
Excellent vacation condo rental. Owner was exceptional to work with and very easy booking. He kept in touch with us and offered help if we needed anything. We had no complaints, enjoyed our week! ...
Distance to beach: 100 feet to Out Front
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Our Sand Castle II 306 is a spacious 3 bedroom beach front condo with the largest balcony in the building overlooking the wide sand beach.Our gorgeous 3 bedroom Sand Castle II beachfront condo on Florida's Suncoast is available for those wanting one of the best accommodations in the Tampa / St....
Featured review
The apartment was perfect for our family . We spent a a very nice days . We will be back . Everything was in very good conditions .
Distance to beach: 50 feet to Indian Shores
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Brand new remodel corner balconies (contact me ) Minivans at Tampa, Saint Petersburg/ Clearwater airports, hot tub, heated pool restaurants accross the street gas grills private parking 250k remodel. Also we own three other direct ocean front condos located there along with Minivans Station at local...
Distance to beach: 50 feet to Indian Shores
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This condo completed a brand new remodel (you can contact me ) and is one of the newest out of all the sandcastles listed. I also have minivans stationed at the airports for your convenience. They are an extra charge. I am fully insured and can usually beat competition buy 50%. I also own two other direct...
Featured review
My wife, pet and I just finished a 30 day stay and couldn’t have been happier. Condo was very clean, spacious and well equipped. The owner works very hard to keep you happy and everything in working condition. We...
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Absolutely beautiful monthly rental in highly sought after Holmes Beach on Anna Maria Island. If you are interested in dates blocked on the calendar, please message me. This 100% updated home has everything from a large heated pool, outdoor shower, lush mature landscaping, completely furnished inside...
Featured review
WOW! I can not say enough about the wonderful stay we had. The house was beautiful and stocked with everything a family would need and the location is perfect. Short walk to beach and Pine St. restaurants...
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Immerse yourself in the beachy bliss of the Coral Beach Bungalow, a stunning 4-bedroom, 2-bath vacation home designed for those who crave the ultimate getaway filled with Sun, Sand, and Sunsets!!! Ideal for families or groups, this luxurious and spacious getaway promises relaxation and adventure in equal...
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We held a 4 day family reunion at this location - 5 adults and 4 children under the age of 5. The home is what you would expect if you borrowed it from a favorite aunt; the kitchen is fully appointed with...
Distance to beach: 50 feet to Indian Shores
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This condominium was newly remodeled (you can contact me ) and is one of the top condominiums located in Sand Castle III. It has its own private spiral staircase that leads down to the pool, hot tub, beach, and gas grills. I have minivans stationed at the airports for your convenience. They are an extra...
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I could not have been happier with our experience at this beautiful condo right on the beach. Everything in the condo is perfect and you have everything you need (even a couple beach chairs, towels and...
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We are offering free nights for select dates. This special is being offered for the date of 8/9/25 and 8/22/25. Just $350 down is required to reserve it. Flexible cancelation policy.Vacation Rental Amenities • Located directly on the beach • Large balcony with strait on view of beach...
Featured review
The views are absolutely incredible and enjoyed all day long. From the first step you take into the condo, from the pool + hot tub and from the master bedroom the views are always enjoyed. The sandy beach...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! Welcome to Beachy Keen, your dream getaway on beautiful Anna Maria Island! This bright and spacious 5-bedroom, 4-bathroom home comfortably sleeps up to 12 guests and offers everything you need for a relaxing and memorable beach vacation.Step inside...
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Seahorse Beach House by Beach Retreats Vacation Rentals 202 81st St, Holmes Beach, FL 34217 VRC17-000118 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub Pet Friendly This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighborsBook with confidence:...
Featured review
We enjoyed our stay. The access to the beach and other amenities was perfect for our family. The rental was very clean and well kept. Most everything you needed for the stay was available. The pool was...
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Escape to paradise at this stunning 4 bedroom, 2 bath home that has everything you need for the perfect vacation. Located just 10 minutes from the beautiful Indian Rocks Beach, you can spend your days relaxing on the beach or soaking up the sun in your own private pool and hot tub.Inside, the home...
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Kickback Cabana 411 79th Street Holmes Beach FL 34217 VRC19-000189 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Heated Pool & Hot Tub | Pet Friendly This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors No cancellation fees! Cancel 60+ days before arrival →...
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We really enjoyed this vacation rental home. Excellent location with close proximity to the beach and restaurants. Also, house located on a quiet street. Amenities were great including the pool and the...
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Welcome home! We have put lots of love to make this home the best version of what we would want in a vacation home. The home is completely updated and centrally located to allow you to enjoy multiple beaches during your vacation. It is only a 5 minute drive to Indian rocks beach, 13 min to Clearwater...
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Welcome to Mermaid Sunset! VRC16-000276 Private Heated Pool/ Spa 200 steps to Holmes Beach Beach Chairs & Wagon Available for use 1 Mile to Pine Ave. Fishing, Shopping, Restaurants, and more High speed Wi-Fi, Smart lock for Self Check-in Pool Heat included with rental Welcome to Mermaid...
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Welcome to Mermaid Sunrise! VRC16-000276 Private Heated Pool/ Spa 200 steps to Holmes Beach Beach Chairs & Wagon Available for use 1 Mile to Pine Ave. Fishing, Shopping, Restaurants, and more High speed Wi-Fi, Smart lock for Self Check-in Welcome to Mermaid Sunrise! This beachy three-bedroom...
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VRC 107 78th street Holmes Beach 34217To Book Directly please visit: /chasing-wavesIf you are looking for something other than a 7 night stay, please give our office a call and we will do our very best to accommodate you! Beach Retreats Reservations Team:“You are vacationing in...
Featured review
We had a great week in this unit and were pleased with many things it had. I would stay there again without hesitation. A FEW issues though with the unit. A fee of $69 for linens. We rented for 10 days...
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Chasing Waves by Beach Retreats Vacation Rentals 107 78th St, Holmes Beach, FL 34217 VRC21-000089 2 Bedrooms | 2 Bathrooms | Sleeps 6 This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighbors “You are vacationing in a residential area. Please be a good neighbor...
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Salt Air East by Beach Retreats Vacation Rentals 7106 Marina Ave Holmes Beach, FL 34217 ​​​​​​​VRC19-000278 2 Bedrooms | 2 Bathrooms | Sleeps 6 | Heated Pool Pet friendly This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighborsBook with confidence:...
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One of the highest rated vacation homes on Anna Maria Island with more than 160 five-star ratings from Airbnb/VRBO!Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated...
Featured review
We truly enjoyed our stay at Kathleen’s house. We had a 11 month and a 3 yr old and it was so nice to have so much baby and kid stuff supplied. We rented a Golf cart which was great to have for transporting...
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Emerald Bay Beach House 306A Clark Street, Holmes Beach, FL 34217 VRC17-000006 | 3 Bedrooms Plus Bonus Bunk Room | 3.5 Bathrooms | Sleeps 6 | Heated Pool & Spa Welcome to Emerald Bay Beach House, your ultimate escape on Anna Maria Island! Our dreamy amenities ensure that guests enjoy a perfect...
Featured review
This was our perfect getaway. The house is beautifully decorated inspired by the blue glistening water and white sandy beaches of Ana Maria Island. The kitchen was fully equipped with everything we needed...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....
Featured review
Wonderful house. Very clean and well stocked. The pool was clean and big. Very close to a very nice beach. Would stay here again.
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Turtle's Bay by Beach Retreats Vacation Rentals 306 Clark Dr Unit B, Holmes Beach, Anna Maria Island VRC17-000006 3 Bedrooms | 3.5 Bathrooms | Sleeps 6 | Heated Pool ​​​​​​​ Pet Friendly This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighborsDog...
Featured review
Visiting Anna Maria Island was amazing!! The weather was beautiful and the home was beautiful too!! I would definitely come back to visit this area.
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Recently renovated! Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the heart of Holmes Beach. Offering 5 bedrooms/3 bathrooms, Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk...
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Love, Love, Love this beach house. I had reserved it a year in advance and was concerned about coming here during a pandemic but as soon as I arrived I was so happy and relieved to be here. The first...
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Perfect for a family vacation or a couple's retreat, this newly listed and newly updated, furnished 2 bedroom/2 bath duplex is located on the north end of desirable Holmes Beach. This home offers all the comforts of home and is just steps to the beautiful white sandy beach. The kitchen is fully equipped...
Featured review
Overall, I was happy with this place. We stayed there two years ago. It is located a block from the gulf. The beach is nice and quiet. The house is very nice with two walk in showers.Area for improvement...
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Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach!Come enjoy a large family and friends gathering at this spacious luxury home just a few minutes stroll to the beach. One of the larger homes on the island, with 6 bedrooms and 4.5 bathrooms and 3400 sq. ft, this home has plenty of room for...
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Conch-Out Beach House 303 68th St, Holmes Beach, FL 34217 VRC19-000273 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool + Spa | Pet-Friendly This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors Completely Renovated February 2025! Welcome to Conch-Out Beach...
Featured review
This is a great house in a fantastic location. The close beach access is very convenient. There are 6 complimentary high quality beach chairs that came in very handy. There is even a handy beach wagon...
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306 67th Street Unit B Holmes Beach, FL 34217 VRC Caribbean Surf by Beach Retreats Vacation RentalsHolmes Beach, Anna Maria Island 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool | Pet-FriendlyYour Anna Maria Island Bungalow Retreat Welcome to Caribbean Surf, a bright and inviting...
Featured review
The home has recently been redone, very comfortable and accomodating with a nice sitting deck and new pool. We had a short walk to a beach access and the location allowed us to visit the north island area...
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This beautiful property offers a perfect blend of indoor and outdoor living, with welcoming accommodations for a maximum of 6 guests, all just a short walk to the pristine white sand beaches and centrally located on Anna Maria Island!The decor is a perfect blend of coastal elegance and comfort, featuring...
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Surf Side Beach House – Gulf Views Hosted by Beach Retreats Vacation Rentals 6605 Gulf Drive, Holmes Beach, FL 34217 VRC19-00290 4 Bedrooms | 4.5 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome...
Featured review
The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally...
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Beach Bliss by Beach Retreats Vacation Rentals 320 64th Street, Holmes Beach, FL 34217 3 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub | Walk to Beach | Pet-Friendly VRC17-000113 Fully Renovated February 2025 Welcome to Beach Bliss, a beautifully updated 3-bedroom, 3-bathroom...
Featured review
Outside patio was perfect! The pool and hot tub were great. Living room area was small but comfortable.
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The Blue Haven by Beach Retreats Vacation Rentals 322 64th Street Holmes Beach, Anna Maria Island VRC25-000096 2 Bedrooms | 2 Bathrooms | Sleeps 6 | Heated Pool This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighbors Please note: The pool technician will need to...
Featured review
The Blue Haven is a very beautiful apartment on Anna Maria Island. It is very close to the beach and very well equipped with everything you need. Modern furniture and very nice bathrooms, beds are excellent....
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Welcome to Sailfish Nest, a beautifully remodeled 2-bedroom, 2-bath duplex located in the heart of Holmes Beach—just a short stroll from the pristine white sands of Anna Maria Island.Step inside to discover a thoughtfully designed, open-concept living space with all-new furnishings. Relax in...
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Welcome to your island retreat in the heart of Holmes Beach, Florida. This pet-friendly property offers a light-filled, thoughtfully laid-out interior that blends coastal charm with everyday comfort, perfect for your vacation getaway.The main living space features an open-concept design with warm...
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Crosswind Cottage 312 A 61st Street, Holmes Beach, FL 34217 VRC19-000277 3 Bedrooms | 2.5 Bathrooms | Sleeps 10 | Heated Pool | Game Room | Elevator This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighborsWelcome to Crosswind Cottage, a spacious island retreat...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS MADE AFTER 10/10/25 WITH A CHECK-IN DATE AFTER 1/17/26! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional...
Featured review
This house was nice, clean and well stocked. The furniture was a bit worn but very comfortable. The yard is small but nicely landscaped and the pool was large enough for our family. The walk to the beach...
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A three-minute walk with easy access to the sugar sand beach on the famous Anna Maria Island. This newly remodeled, pet-friendly home creates fun Florida island vibes with two bedrooms perfect for a family or a small group getaway. Anna Maria HIdeaway lies within a stone's throw from the trolley...
Featured review
We enjoyed on our stay at this well-kept property on Anna Maria Island. It offered privacy with a good central location.
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In the heart of Holmes Beach on Anna Maria Island rests this charming recently renovated, pet-friendly home just steps to the beaches. Misty Beach is a charming coastal home with a flamingo-shaded exterior, quickly moving you onto island time. The interior creates a welcoming and calming environment....
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Starfish Cove by Beach Retreats Vacation Rentals ​​​​​​​302 60th Street Holmes Beach, FL 34217 VRC19-000274 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Heated Pool & Spa ​​​​​​​ Pet Friendly This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect...
Featured review
My husband and I had the best time at the home we rented on Anna Maria Island. It was spacious and we had far more room than we needed for just the two of us. When we arrived, everything was clean and easy...
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Starfish Isle by Beach Retreats Vacation Rentals 5803 Holmes Blvd Holmes Beach, FL 34217 VRC 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub Pet Friendly This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighborsAt 4 bedrooms and 3 full bathrooms,...
Featured review
The home was absolutely wonderful with everything we needed to make our weeklong vacation a success! Everything was clean and well kept. The beds were comfortable and the best part was the pool and pool...
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New Name - A Wave From It All, formerly known as Island Dream, is a recently updated custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 3 bedrooms/2 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the...
Featured review
This was my family's first vacation to Anna Maria island. The house was beautiful and in a great location, convenient to all the hot-spots! The lay-out of the house was great, master bed and queen beds...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....
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