5 BR | 2 BA | Sleeps 10 | Quick View
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About this property
One of the best values on Anna Maria Island -- and one of the highest rated with more than 150 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 ...
Property Type
Anna Maria Island House
We were attending a beach wedding and made a vacation out if it. I connected with the owner Kath immediately. She was generous, attentive, available and without a doubt the best host we have ever met. ...
2 BR | 1.5 BA | Sleeps 6 | Quick View
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About this property
Shady Palms is a cozy secluded beach cottage right on the beautiful Gulf of Mexico. Walk out the back door to a white, sugar-sand beach and the sparkling Gulf waters. Shady Palms is the most perfect spot you'll ever find on the beach - have the best of both worlds - the sun and the shade.Beach and ...
Property Type
Anna Maria Island House
This house is the best rental we have ever stayed in! The scenery out back is incredibly relaxing.. trees, Adirondack chairs, the OCEAN!! It is so private, and also the best equipped kitchen I’ve ever ...
3 BR | 2 BA | Sleeps 6 | Quick View
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Less than a minute's walk to the beach!Watch the sunset from the house!PARKING FOR ALL...Bring your boat or RV...Invite guests... There's room for everyone!Shell House is a two-story, 3-bed, 2-bath, multi-level fun-house on a large shady lot in a quiet residential neighborhood only two blocks ...
Property Type
Anna Maria Island House
I lived in Holmes Beach for many years. It was always my favorite place to be. When I needed to move I promised myself I would rent and come as often as I could. SunPlaza West has always been my go to ...
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About this property
Located on 5th Avenue in Holmes Beach this unit is out of the way on a dead end street. Seaduction offers a heated pool, and every amenity to make your stay here a comfortable one. After a day at the beach, you can relax by the pool or in the private, nicely landscaped picnic area. There are only 4 units ...
Property Type
Anna Maria Island Condo
We love our stays at Seaduction. It has become our 3rd home! Morgan and Dan have created a home for their guests not a rental. They are responsive and very helpful. It is well stocked, great location, ...
4 BR | 3.5 BA | Sleeps 8 | Quick View
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Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, laid back way of life on the north end of the island being only steps to the gorgeous bayside beach with city park or a 5 minute walk to the world renowned Bean Point! You are also ...
Property Type
Anna Maria Island House
Hosts are fabulous! very responsive and caring! House is amazing! our friends and family were blown away by how much attention to detail they put in to the furnishings and the home itself! A true paradise!
6 BR | 5.5 BA | Sleeps 14 | Quick View
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ASK US ABOUT MULTI WEEK DISCOUNTS!! Featuring 6 bedrooms 5.5 baths (sleeps 14) and a fantastic location - just a 1 minute walk to the white sands of the 65th St Beach Access!This vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining ...
Property Type
Anna Maria Island House
We just returned from a one-week stay at Oceanview and all expectations were happily exceeded. We were a family of 11 spanning several generations - all adults and adult children and one baby. The house ...
2 BR | 2 BA | Sleeps 5 | Quick View
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About this property
Only Dates Available for 2023. Book now before they are gone. CALL FOR UNBELIEVABLE SAVINGS. ONLY PHONE CALLS GET DISCOUNTS.August 5-19, 2023 Aug 19- Sept 2, 2023 Sept 2-16. 2023 Sept 16-30th, 2023 Oct 28-Nov 11 Nov 11-25, 2023 Non 25-Dec 2, 2023 Dec 2-16, 2023TWO WEEK MINIMUM STAY. No ...
Property Type
Anna Maria Island Condo
️ love this area one of my favorite places to stay AnnaMaria island.. love it .. can’t wait to go o back
4 BR | 4 BA | Sleeps 12 | Quick View
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Ideal Location - Family Vacation Accommodation 2 Individual Villas, 4 Bedroom 4 Baths Sleeping for 8-12 GuestsThe Alecassandra Vacation Villas is a small 4 bedroom vacation property that is family owned by Nick and Vicki Zec and named after our children Alec & Cassandra. When renting entire ...
Property Type
Anna Maria Island Villa
Unbelievable location with state of the art appliances throughout. Views of the ocean and the beach that were priceless.
3 BR | 2.5 BA | Sleeps 6 | Quick View
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About this property
This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the ...
Property Type
Anna Maria Island House
What an awesome place. Lots of rooms to stretch out. The 2 car garage and big drive way were nice for ease of parking and to securely store things. The large shared pool is wonderful and perfect temp. ...
3 BR | 3 BA | Sleeps 6 | Quick View
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Welcome to Gone Coastal 3! This quaint three bedroom, two bathrooms plus a half bath vacation home is located just a short walk from Anna Maria Island’s sugar white sands and crystal clear waters! Beach towels, six beach chairs, and a beach wagon are provided to ensure your days spent in the sun ...
Property Type
Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
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About this property
We have developed a comprehensive Safety / Cleaning / Sanitation Plan and work with an amazing team to ensure the home & pool are sparkling clean for all of our guests. Our home goes through rigorous cleaning per CDC guidelines using only EPA approved detergent and highest MERV 13 A/C filters changed ...
Property Type
Anna Maria Island House
We had a remarkable time at this house. The location, pool and house exceeded our expectations. We'll come back.
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About this property
My wood-frame beach cottage was built in 1936, and was originally part of 6-8 cottages and a lodge house. It is the only surviving cottage, many having been taken by hurricanes. (Forward of the cottage’s beach, a street and an entire city block of the old subdivision are submerged beneath the ...
Property Type
Anna Maria Island Cottage
So close to the water for someone with gait issues. We always enjoy our stay here. So close to restaurants and beach. Best of both worlds
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area! It also has an outside shower for showering off after your trips to the beach. Inside it has a split plan with a king sized bedroom and a second bedroom with ...
Property Type
Anna Maria Island House
This duplex includes stunning beachy interior decorating, great location (quiet neighborhood with an easy walk to a white sands beach) with a bonus heated pool with outdoor shower, which was ideal after ...
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area! It also has an outside shower for showering off after your trips to the beach.Inside it has a split plan with a king sized bedroom and a second bedroom ...
Property Type
Anna Maria Island House
4 BR | 2.5 BA | Sleeps 6 | Quick View
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About this property
Beautiful 4 bedroom, 2.5 bathroom home with direct access to Anna Maria Canal and private heated pool overlooking the water. Take a kayak ride right off your private dock area or cast a fishing pole and catch dinner. This home has lots of space and is ready for you to come enjoy all of what the island ...
Property Type
Anna Maria Island House
We met with the owner and he was very helpful in showing us around the property.The house was very clean and was everything we had expected. Brian and Marie
2 BR | 2 BA | Sleeps 6 | Quick View
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About this property
--Don't see the exact dates you are looking for? Check out the additional availabilty in my 1br 1 bath unit (40 steps away from this unit) /5597This updated 2 bedroom 2 bath condo is located at Bradenton Beach on Anna Maria Island, directly off Gulf Drive. Runaway Bay is a lovely vacation resort on ...
Property Type
Anna Maria Island Condo
This is the first time we stayed at Dans Florida Condos. The condos were right across the street from the private beach access, and I could not have asked for a cleaner unit. Pictures tell the whole story. ...
1 BR | 1 BA | Sleeps 4 | Quick View
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About this property
This non-smoking unit is over 900 sq ft with a screened in terrace complete with a quiet, peaceful view of the lagoon that flows through the center of the complex (see the pictures). Conveniently located close to Sarasota Airport (20 minutes) and the Tampa Airport (55 minutes). Also, close to major Florida ...
Property Type
Anna Maria Island Condo
The location is great, right across street from beach. Trolly stop nearby to ride around the beach and get off at other stops for free. Places to eat within walking distance. Nice pool and tennis courts. ...
5 BR | 3.5 BA | Sleeps 12 | Quick View
Distance to beach: 0.2 miles to bradenton beach
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About this property
You will fall in love with this peaceful retreat. This home comes with (2) 6 person golf cart. You will love zooming around the island on the golf carts, window shopping at all of the gorgeous real estate. This unit is within walking distance to the beach, you will love being able to walk back and forth ...
Property Type
Anna Maria Island House
We had an amazing stay at Taylor's house! We had two families, so we loved that there was an upstairs unit and a downstairs unit. The upstairs unit has a larger eating area and kitchen, so that was our ...
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About this property
Escape the Madness to the serenity of Anna Maria's north end. This single family, two bedroom, 2 bathroom, ground level house is located on the far north end of Anna Maria Island near Bean Point. The property is only 250 feet from the sugar sand beaches where you can walk for hours or sit and enjoy ...
Property Type
Anna Maria Island House
We loved our trip to Anna Maria and this perfect, very comfortable house. This 2 bedroom/2 bathroom was the perfect amount of space for us. Very clean, well-appointed, fluffy towels, manicured yard and ...
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About this property
It is almost always summer on Anna Maria! Availability is updated frequently, so please check our calendar often.We were very fortunate to have no flooding from Hurricane Idalia. September is blocked for some planned renovations. Projects may be complete before end of month, so if you are interested ...
Property Type
Anna Maria Island House
This was one of the most unique homes we have ever rented. Equipped with everything anyone would need on vacation. Great location, easy walk to the beach, and many restaurants nearby.All in all, we ...
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About this property
Breathtaking sunset views atop your own expansive and elevated deck await at this spacious single story home on gorgeous Anna Maria Island! This home features 4 large bedrooms, each with its own private en suite bathroom, a large kitchen, living room, additional sitting area plus two separate dining spaces. ...
Property Type
Anna Maria Island House
4 BR | 2 BA | Sleeps 8 | Quick View
Distance to beach: 1 miles to Anna Maria
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About this property
Bring your boat and enjoy! This cozy canal front 4 bedroom 2 bath home is in a nice, quiet and convenient location close to the bay and only a 5 minute bike ride to the beautiful white sands of Anna Maria Island Beach. Also within a 5 minute or less bike ride are Anna Maria City Pier, where you can grab ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 4 | Quick View
Distance to beach: 0.5 miles to Manatee Beach
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About this property
2 bed/2bath condo on second floor, fits up to four guests, close to the gulf beach. Turnkey furnished and spruced by the owner. Shops and restaurants are close by. Trolley stop for free rides on the island is around the corner. Come and enjoy!Just remodeled and equipped with more than everything ...
Property Type
Anna Maria Island Condo
This condo was the PERFECT place for our family of three to enjoy Anna Maria Island! It was clean, cozy, and had everything we needed! Carla was a wonderful host who was very accommodating and gracious ...
3 BR | 3 BA | Sleeps 8 | Quick View
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Escape to a tropical paradise at our stunning Anna Maria Island Villa! This magnificent property features a private pool with a breathtaking waterfall, as well as an elevator, lanai, and Tiki hut. Offering the ultimate island experience!The villa boasts 3 spacious bedrooms plus a wonderful tower room, ...
Property Type
Anna Maria Island Villa
Beautiful house and Celine is an excellent host. We stayed here a week for a family vacation and really enjoyed our time. House had everything we needed and more. Very clean and super close to the beach. ...
2 BR | 2 BA | Sleeps 6 | Quick View
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About this property
Enjoy Anna Maria Island from this fresh and casual 2 bedroom, 2 bath poolside condo in Runaway Bay!Just steps from the beach and the bay, Runaway Bay has it all – a heated, salt water pool (the largest on the island!), tennis, bocce ball and shuffleboard courts, a work out room, clubhouse and ...
Property Type
Anna Maria Island Condo
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About this property
A guest had this to say: "Songbird is a cute little purple house on a quiet side street on Anna Maria Island. I referred to the house as little, it is really quite spacious & comfortable. This is our 6th stay at Songbird & we are looking forward to our next stay. This trip we were on side ...
Property Type
Anna Maria Island Cottage
Second time staying here and actually lucked out with a cancellation. 2 week stay and couldn’t have been better timing weather wise. Short couple block walk to the pristine white sand beaches. Easy haul ...
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About this property
We are back! It is almost always Summer on Anna Maria Island! Availability is updated frequently, so please check our calendar often.We were very fortunate to have no flooding from Hurricane Idalia. Dolphin Cottage is rented until early 2024. March & April and most of Summer are available!Dolphin ...
Property Type
Anna Maria Island House
The location is easy to find, close to beaches, stores, etc. Quiet pretty much all the time, just off the main road so other areas are easily accessed.
3 BR | 3 BA | Sleeps 8 | Quick View
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Welcome to paradise- AMI VILLA! When you come to Anna Maria Island for vacation, make this charming Mediterranean beach 3 bedroom & 3 bath villa your home away from home! With much to offer, this home will have your family wanting to return to Anna Maria Island year after year.Features include: -3 ...
Property Type
Anna Maria Island Villa
We just spent the week at AMI Villa and Loved it! Beautiful house! Loved all the balconies! The fenced in yard and pool area was perfect. The kitchen is well stocked. The pool is perfect. The sun hits it ...
5 BR | 5 BA | Sleeps 14 | Quick View
Distance to beach: 0.1 miles to Bayside Beach
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About this property
Just updated 2020, with state of the art finishes! 5 BR + 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep up to 14 with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! Email owner about our other property that sleeps 6 for ...
Property Type
Anna Maria Island House
4 BR | 3 BA | Sleeps 10 | Quick View
Distance to beach: 0.0 miles to Gulf Beach & Tampa Bay Beach
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About this property
Newly renovated! Read our description carefully as we have upgraded and added many amenities!Minimum Stays Required Based on Dates - Inquire DirectlySIRENIA BEACH HOUSE ~ Pick your beach! Sirenia Beach House is located between 2 beaches on a quiet cul de sac with fabulous views of the waterfront. ...
Property Type
Anna Maria Island House
4 BR | 3 BA | Sleeps 12 | Quick View
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About this property
Sept 2023 now $286 per night plus fees and taxes. Minimum stay 3 nights for the above dates onlyOUTSIDE HIGHLIGHTS: Soft Sandy Backyard Beach Area Tons of New Outdoor Sun Loungers New Pool Terrace Resurfaced and Newly Tiled Heated Pool New Outdoor Conversation Set New Hot Tub Outdoor Shower Hammock Outdoor ...
Property Type
Anna Maria Island House
We loved our time at Sirena Cove. There were so many amenities and room for all of our adult children, their spouses and our grandchildren all under the age of four. The pool was great fun and we enjoyed ...
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Enjoy beautiful Anna Maria Island relaxing in a spacious ground floor condo unit with 2 bedrooms and 2 baths overlooking the heated community pool. This quiet slice of paradise has a large screened lanai off the living room with a pool view. Enjoy the amazing white sand beach and gorgeous sunsets within ...
Property Type
Anna Maria Island Apartment
4 BR | 4 BA | Sleeps 8 | Quick View
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About this property
Welcome to our beautiful Italian Mediterranean home in Holmes Beach, Anna Maria Fl! Recently renovated, this home sleeps 8 very comfortably! with 5 Beds and 2 New Air Mattresses; It has a private enclosed heated pool area with an outdoor bar, and a luxury outdoor Pottery Barn Extended Dining table, ...
Property Type
Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 0.1 miles to 30 seconds to your left
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About this property
This newly redesigned elevated 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 it's stunningly ...
Property Type
Anna Maria Island House
Key Amenities
About this property
This is a two bedroom house on Anna Maria island, and faces the bay side. The water is literally 20 ft from your back door. Looking from your private dock to the north is the Manatee bridge, the Skyway bridge and a view of St Pete. Looking to the south you see the Cortez bridge and beyond to Sarasota. ...
Property Type
Anna Maria Island House
Great location. Great view. Great everything! Can't wait to come back. Terry is great and we appreciate the work that went in to the clean up after Hurricane Ian so we could fall in love with this place. ...
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About this property
2 bedroom 2 bath 1000 square feet condo with a beachfront view of the Gulf of Mexico on the quiet, peaceful Anna Maria Island. Walking distance to many restaurants and bars. 30 minutes away from the Sarasota/Bradenton airport. Free trolley to go anywhere on the island.
Property Type
Anna Maria Island Apartment
