Anna Maria Island Rentals by Owner

(23 rentals)
booking message booking message

2 BR | 2 BA | Sleeps 6 | Quick View

16

$350

avg/night

View Details

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 ...

View all property information

Property Type

Anna Maria Island Condo

"Fantastic Condo!"

Morgan and Dan - we loved your beautiful condo. We wish we could have stayed even longer. You left no stone unturned. The condo is well appointed and nicely decorated. We had the best time and really ...

See all reviews

Show less

Key Amenities

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

About this property

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 slide and grotto waterfall. Covered outdoor entertaining ...

View all property information

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 ...

See all reviews

Show less

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 ...

View all property information

Property Type

Anna Maria Island House

"Location!"

The location was awesome, we were only one block from the beach! We kept our loaded wagon in the garage and were ready to go each morning. The house was roomy and bright; with 3 decks there was lots of ...

See all reviews

Show less

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 ...

View all property information

Property Type

Anna Maria Island House

"Excellent"

This was a perfect place for our family to stay. The memory of it is pure perfection. The host was phenomenal and the stay accommodations were very comfortable.

See all reviews

Show less

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 ...

View all property information

Property Type

Anna Maria Island House

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Less than a minute's walk 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 ...

View all property information

Property Type

Anna Maria Island House

"Great family vacation!"

We stayed at shell house @ , I was able to bring my daughter and son and their fiancé’s to stay with us, it was just as I remembered! What a great trip! The house is so cozy and the location is perfect! ...

See all reviews

Show less

Key Amenities

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

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 ...

View all property information

Property Type

Anna Maria Island House

Show less

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 ...

View all property information

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 ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

8

$289

avg/night

View Details

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 ...

View all property information

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 ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 5 | Quick View

4

$251

avg/night

View Details

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 ...

View all property information

Property Type

Anna Maria Island House

"Love it"

This cottage is amazing, has everything you need (even for kids). The location is great - the beach is 5 min walking, has nice restarants near by. We'd like to visit again.

See all reviews

Show less

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 ...

View all property information

Property Type

Anna Maria Island House

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

18

$228

avg/night

View Details

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 ...

View all property information

Property Type

Anna Maria Island Cottage

"30th Anniversary getaway"

Very Awesome little cottage with all the necessities and more. Spoke with Ms. Libby on the phone a couple times, and she was quick to respond to text messages. My Bride of 30yrs and I looked for something ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

3

Distance to beach: 0.5 miles to Manatee Beach

$198

avg/night

View Details

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 ...

View all property information

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 ...

See all reviews

Show less

4 BR | 2 BA | Sleeps 8 | Quick View

7

$385

avg/night

View Details

Key Amenities

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

About this property

Thankful that Anna Maria survived Hurricanes Ian and Nicole mostly unscathed. There are still some open weeks in January and March, and the weather has been amazing! Availability is updated frequently, so please check our calendar often.Peacock Place, our 'big house' on Anna Maria Island is a sprawling ...

View all property information

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 ...

See all reviews

Show less

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! Big 5 bedroom house, 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, ...

View all property information

Property Type

Anna Maria Island House

"Amazing stay!"

This was our second trip to this lovely home. This time we were traveling with my sister's 14-month-old granddaughter and it was so nice to have all the extra gear supplied for infants -- even a baby bath ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

3
Owner special: Last minute January openings! Book direct on our website, retain these weeks year after year. Cheers

$250

avg/night

View Details

Key Amenities

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

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 ...

View all property information

Property Type

Anna Maria Island Condo

"Excellent"

Beautiful , clean & comfy. Great place to stay for family, centrally located, nicely furnished. Really will highly recommend!

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

5

Distance to beach: 75 feet to Anna Maria

$373

avg/night

View Details

Key Amenities

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

About this property

This second floor 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 including ...

View all property information

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 ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

5

$194

avg/night

View Details

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. ...

View all property information

Property Type

Anna Maria Island House

"Manatee Cove"

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. ...

See all reviews

Show less

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 ...

View all property information

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 ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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 ...

View all property information

Property Type

Anna Maria Island Apartment

Show less

Key Amenities

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

About this property

TWO WEEK MINIMUM STAY. No exceptions. No Pets. Sorry20 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. ...

View all property information

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 ...

See all reviews

Show less

2 BR | 1 BA | Sleeps 4 | Quick View

8

$177

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 ...

View all property information

Property Type

Anna Maria Island Cottage

"Cute, Comfy, Clean, and Convenient Beach Cottage"

Excellent Stay!!! This was our 3rd time visiting Anna Maria Island and our 1st time staying at Songbird Staying at Songbird was the BEST and most comfortable stay of all our visits! Joel is the perfect ...

See all reviews

Show less

Key Amenities

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

About this property

Located on Key Royale private and secluded golf island retrieve on Anna Maria Sound. Quiet, off the beaten path , yet only one mile from the beach and rest of island amenities Expansive 2 bedroom 2 bath open design living room , dining and kitchen areas perfect for entertaining family and friends .Extensive ...

View all property information

Property Type

Anna Maria Island House

Show less

Map
Expand map Close map
Anna Maria Island Vacation Rentals