Anna Maria Island Rentals by Owner

(20 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

SPECIAL 6 NIGHT STAY SEPT 10-16 ONLY $595!!!!!ASK US ABOUT MULTI WEEK DISCOUNTS!!Featuring 6 bedrooms 5.5 baths (sleeps 12) and a fantastic location - just a 1 minute stroll to the white sands of the 65th St Beach Access! This lovely home offers a huge private heated pool with spa, rock water ...

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Property Type

Anna Maria Island House

"Awesome home"

My family of 11 stayed at this beautiful home for 7 days. We had five kids ranging from 5yr-12yr and I will say the pool was the biggest hit! The entire home was very spacious and even with our large group ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

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 ...

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Property Type

Anna Maria Island Villa

"Perfect"

I cannot say enough good things…. first of all about the booking process, Vicky made everything so easy and a big shout out to Wagner Realty!! awesome communication super smooth rental process!! you guys ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

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 ...

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

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 8 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

"Quiet Beach View Location"

This house is all about the location!! It's a Great location, 2 houses from the beach on a dead-end road. This home has 2 decks facing the beach for you to sit out and enjoy the beautiful sunsets! ...

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2 BR | 2 BA | Sleeps 6 | Quick View

8

$207

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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 ...

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Property Type

Anna Maria Island Condo

"Beautiful Beachy Condo Close to the Beach"

We really enjoyed our stay. I like the small remodeling touches you have made to the condo, as we have stayed in this unit when it was under different ownership. Love the pool area and especially the screened ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Less than a minute stroll to the beach!Watch the sunset from the house!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 from popular shopping & dining.Three bedrooms with two king beds and one queen ...

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Property Type

Anna Maria Island House

"My retirement vacation"

My wife and I stayed for a month to celebrate retirement. The location to the shops and restaurants was great. The biggest plus was the location to the beach. Fantastic. There was plenty of parking at the ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Stay at the home of a NY Times best-selling food writer! Pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated pool amid lush landscaping and beautiful rock waterfall. Chef-outfitted kitchen with new appliances, 60-inch Sony HDTV, Italian leather ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 4 | Quick View

5

Distance to beach: 75 feet to Anna Maria

$205

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

This ground level walk out two bedroom two bath condo has just been totally renovated and recently redecorated. The condo features a comfortal coastal style that has been decorated by the owner. The condo sits midway between the Bay of Sarasota and the Gulf of Mexico. Runaway Bay offers many amenities ...

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Property Type

Anna Maria Island Condo

"A lovely place for a perfect vacation!"

I booked this condo for my children and their spouses to stay over Christmas, and it was even better than the listing information portrays. The space is decorated beautifully, and has everything you would ...

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2 BR | 2 BA | Sleeps 5 | Quick View

3

$231

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

About this property

Ann's cottage is a cozy, original 1950’s, one story beach cottage in the Holmes Beach section of Anna Maria Island. It is a short walk- six houses to the beautiful sugar white sands and sparkling blue waters of the Gulf of Mexico. The homes sits in a quiet neighborhood, yet is only one street away ...

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Property Type

Anna Maria Island House

"Lovely Home and Location"

I was very pleased with our rental. I had an accident going down a step from the laundry room and have 3 cracked ribs as a result of the fall. The light into the room was across the room from where the ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

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 - with the best of both worlds - the sun and the shade.Beach and ...

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Property Type

Anna Maria Island House

"Comfort, convenience, and shade on the beautiful Gulf of Mexico!"

Shady Palms has all the comforts of home, spacious living areas and bedrooms. It’s clean inside and wonderfully shady outside! The kitchen is stocked with cooking/dining utensils, and plenty of towels ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

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 ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 4 | Quick View

16

$156

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

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 ...

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Property Type

Anna Maria Island Cottage

"Anniversary week"

We were married same month in year prior on this beach and just had to come back. We have this booked again next year. We just cannot get enough of this place, this year we actually got to relax and enjoy ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$429

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

An addendum to our cancellation policy: If the governor of Florida issues a Florida travel ban you will receive a refund. Additionally, every reservation is offered two different trip insurance policies. One:) cancel for thirty different reasons and receive a full refund (cost 7% of the gross rental amount). ...

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Property Type

Anna Maria Island Condo

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4 BR | 2 BA | Sleeps 8 | Quick View

7

$343

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

It is almost always Summer on Anna Maria Island! Summer reservations are mostly full, but there are a few open weeks left! Availability is updated frequently, so please check our calendar often.Peacock Place, our 'big house' on Anna Maria Island is a sprawling old-Florida style home with 4 bedrooms, ...

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Property Type

Anna Maria Island House

"Paradise discovered!"

Our group of 6 adults had an amazing time in this lovely Floridian home. So much space and a great layout for all to enjoy. Excellent kitchen layout for multiple cooks. Lots of spaces to relax in. Great ...

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2 BR | 2 BA | Sleeps 6 | Quick View

8

$267

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

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 ...

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Property Type

Anna Maria Island House

"Cottage by the Sea"

We visited Anna Maria in November with lifetime friends. The house was charming and comfortable. The kitchen was well-equipped and we cooked several dinners and ate outside under the beautiful palms and ...

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2 BR | 2 BA | Sleeps 4 | Quick View

3

Distance to beach: 0.5 miles to Manatee Beach

$132

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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 ...

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Property Type

Anna Maria Island Condo

"Amazing vacation"

Carla is an excellent hostess. It was my first time ever renting from someone and she answered my million questions and was very patient. Condo was wonderful and clean with everything you need in a great ...

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2 BR | 1 BA | Sleeps 4 | Quick View

7

$129

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

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 ...

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Property Type

Anna Maria Island Cottage

"Affordable AMI"

A cute clean house with a beautiful backyard garden! Nice and clean and close to the beach. Owner stayed in constant contact and we had zero problems. Would gladly stay here again!

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

TWO WEEK MINIMUM STAY. No exceptions.20 STEPS TO THE SAND GREAT VIEW Last minute deals don’t last long we price to rent. If you’re interested in the July dates call don’t email. . We are cheaper than any two bedroom two bath on the island we are price to stay booked. Thank you ...

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Property Type

Anna Maria Island Condo

"Wonderful Experience / Highly Recommended"

We spent 3 wonderful weeks at 114 Tiffany Place at Anna Maria Island, FL.... This is our favorite beach community in Florida and now 114 Tiffany Place is our favorite condo!!! The owner is great to work ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

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 ...

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Property Type

Anna Maria Island Villa

"Loved our stay at AMI 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 ...

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2 BR | 2 BA | Sleeps 4 | Quick View

4

$175

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Rentals by owner

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. ...

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Property Type

Anna Maria Island House

"wonderfully located gem!"

The location is AMAZING! We saw dolphins by the dock multiple times! The owner was equally as AMAZING. He was SO very kind, said he'd do something & did what he said. Absolutely LOVED our stay & can't ...

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Anna Maria Island Vacation Rentals