Anna Maria Island Vacation Rentals

(119 rentals)
Osprey Roost - Pet-friendly and very close to beach!

$199

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

It is always summer on Anna Maria Island!We have one of the most pristine, un-crowded beaches you will ever visit. Enjoy a champagne breakfast, Duffy's burgers for lunch, or cocktails at sunset! In addition, there are many other fabulous things to do here - Busch Gardens, Universal Studios and Disney ...

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Property Type

Anna Maria Island House

"Ideal home away from home"
Reviewed April 15, 2019

We can't stop talking about how much we miss "our" Osprey Roost. The car rarely leaves the driveway, as everything we need and want is within walking distance. The gulf is a very short walk, as are the ...

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Anna Maria Paradise - Private Pool & Canal front home

$217

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

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 ...

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Property Type

Anna Maria Island House

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End 0f Year Special $300/night Min 5 Nights

$300

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

PRIVATE HEATED SALTWATER POOL + PRIVATE ELEVATOR + STEPS TO GULF BEACH! SLEEPS 10 - FULLY EQUIPPED - ULTRA-CLEAN! WALKING DISTANCE TO SHOPS, RESTAURANTS, AND NIGHT SPOTS!This is a fully-equipped vacation rental:All bed and bath linen are provided. There are extra bath towels for each guest, and ...

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Property Type

Anna Maria Island Townhome

"Great home away from home!"
Reviewed October 6, 2018

My friends and I came to Anna Maria Island to get some much needed rest and relaxation, and this rental was the perfect place. The location is awesome, as it is walking distance from the beach. But who ...

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Casita Marina - 11103

2 BR | 2 BA | Sleeps 6 | Quick View

1

$164

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

This classic home located on the North End of Anna Maria Island is the perfect home for your tropical beach vacation. The beautiful Anna Maria beach is across the street about 100 steps away! The home is a legal duplex (11101+11102 Gulf Drive). This unit has two bedrooms and two bathrooms. The Kitchen ...

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Property Type

Anna Maria Island Condo

"This is a Charming Beach Cottage"
Reviewed February 28, 2019

This duplex has been completely renovated inside with a nice kitchen and bathrooms. It is a perfect location in the quiet northern end of AMI. It is within walking distance to restaurants and the beach ...

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Sea Salt

3 BR | 3 BA | Sleeps 6 | Quick View

$153

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Sea Salt is a beautiful recently updated home home nestled in the heart of Holmes Beach-just a short 5 minute walk to the world renowned beaches of Anna Maria Island. This 3 bedroom 2.5 bath home offers everything you need for an unforgettable vacation. Enjoy the private heated pool with sand area, covered ...

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Property Type

Anna Maria Island House

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Anna Maria Island Club Unit 22

$179

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

This amazing beach front 2 bedroom / 2 bathroom condo is perfect for an island vacation. This unit features a fully equipped kitchen, elevator, washer & dryer, cable TV / wifi, shaded assigned parking and a shared heated pool & spa. But, it doesn't stop there, this unit has stunning views of the ...

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Property Type

Anna Maria Island Apartment

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Turtle Cottage - Anna Maria Island

$220

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. This great getaway sleeps up to 4.The space:The cottage has an ...

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Property Type

Anna Maria Island Cottage

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Summer House Upstairs

2 BR | 2 BA | Sleeps 6 | Quick View

$197

per night

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Key Amenities

  • Air Conditioning
  • Pool

About this property

This beautiful villa has two bedrooms and two bathrooms, lots of storage space, laundry room, spacious kitchen and open and light living room. In the living room there is a sleepers sofa. The unit is bright and light, is fully furnished and gives its guests the feel of home. Kitchen is fully equipped. ...

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Property Type

Anna Maria Island Villa

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Good Time and Tan Lines

3 BR | 3 BA | Sleeps 6 | Quick View

$299

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Don't miss the opportunity to one of the first to stay in this Stunning 3 bedroom 3 bathroom with bonus den area that has been completely renovated from bottom to top. This property is a new hidden gem of Holmes Beach.   The open concept floor plan is warm and inviting making you feel at home ...

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Property Type

Anna Maria Island Townhome

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Bare Feet Retreat

3 BR | 3 BA | Sleeps 6 | Quick View

$299

per night

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Key Amenities

  • Full Kitchen

About this property

Stunning beach front resort with gated covered parking.

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Property Type

Anna Maria Island House

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Almost Beach Apartments

2 BR | 1 BA | Sleeps 5 | Quick View

1

$90

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

We are a small, clean, 'Old Florida' business located directly across the street from the Gulf of Mexico.Our units are comfortable and priced to allow the average person a chance to spend quality vacation time on our beautiful wide sandy beaches of the Gulf of Mexico! We are located on the free trolley ...

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Property Type

Anna Maria Island Apartment

"Family Vacation 2019"
Reviewed April 5, 2019

Everything was just as expected and we enjoyed everyday! The beach is right out your doorstep, well it is the best part. We'd love to stay again!

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Bay View Dream

4 BR | 3.5 BA | Sleeps 8 | Quick View

$242

per night

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Key Amenities

  • Air Conditioning

About this property

Ah, Bay View Dream! This lovely 4 bedroom, 3.5 bath home is located in the heart of Historic Anna Maria City. It sits right on an expansive waterway leading into Tampa Bay and has been lavishly decorated with all the creature comforts and more. Stunning water views from living room, dining room, kitchen ...

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Property Type

Anna Maria Island House

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AquaBella

3 BR | 2 BA | Sleeps 6 | Quick View

$207

per night

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Key Amenities

  • Air Conditioning

About this property

AquaBella is a delightful architecturally designed canal front home that offers 3 bedrooms and 2 full bathrooms. This U-shaped home was constructed to take full advantage of the many tranquil views of the deep water canal and lush tropical landscaping. As you sit with your morning tea or coffee all your ...

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Property Type

Anna Maria Island House

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ALECASSANDRA VACATION VILLAS, Your Family Reunion Accommodation

$257

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Ideal Location - Family Reunion Accommodation 1 Property - 2 - Buildings - 5 Individual Villas - Sleeping for 30The Alecassandra Vacation Villas is a small 10 bedroom vacation resort 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

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Katie's AMIable Condo

2 BR | 2 BA | Sleeps 4 | Quick View

1

$129

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Two bedroom, two bath condo for rent in the lovely Runaway Bay complex in Bradenton Beach, on beautiful Anna Maria Island, Florida! Live the relaxed lifestyle on Anna Maria. Enjoy morning walks and evening sunsets on the beach, just across the road. While away the afternoon by the big, beautiful pool ...

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Property Type

Anna Maria Island Condo

"Snowbird Retreat"
Reviewed December 6, 2018

We enjoyed this unit very much! It has all the amenities we need! It is a very quiet spot and has a nice view of the pond.

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Sandcastle 4

3 BR | 2 BA | Sleeps 6 | Quick View

$204

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

OVERVIEW Sandcastle is a beautiful beach front property offering all of the conveniences you would want in an island stay. You will find the furnishings & facilities very accommodating to make your vacation one to remember. This condo is a quaint 3 bedroom 2 bath beach front condo located in the ...

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Property Type

Anna Maria Island Apartment

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Coconut Breeze Estate

4 BR | 4 BA | Sleeps 12 | Quick View

$332

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Coconut Breeze is a custom home on the north end of Anna Maria in the quiet residential area in the sought after City Of Anna Maria. Offering 4 bedrooms / 4 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the luxurious heated pool, gourmet ...

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Property Type

Anna Maria Island House

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Fantastic Beach View - Convenience & Comfort at Beach House for Family Fun.

3 BR | 2.5 BA | Sleeps 8 | Quick View

3
Owner special: Fall rental openings with seasonal off-peak price, excludes Holiday weeks. Week rental $1500 total.

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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

"Review of an Excellent Rental"
Reviewed April 19, 2019

The house is in a great location and is well equipped. Beach is only a few minutes away. The free trolley, which serves the entire island, is about a 5 minute walk.Supermarket and drug stores are nearby. ...

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Villa Del Mar

4 BR | 4 BA | Sleeps 10 | Quick View

$504

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Cool and calming tiled floors, modern furnishings, and updated appliances give this vacation home an air of Tommy Bahama feel. We know how exhausting and stressful traveling can be so don’t feel an ounce of guilt if the second thing you do is plop down on the living room’s couch and switch ...

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Property Type

Anna Maria Island House

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Coconut Bayou Pool Home RELAX in the best section of Anna Maria

2 BR | 2 BA | Sleeps 8 | Quick View

Owner special: Book for November and get 20% OFF our book rate

Distance to beach: 0.3 miles to Gulf Front Sandy Beach

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

2 Bedroom 2 full Bathrooms sleeps 8 has large Patio and pool and spaSorry February is already booked but parts of January and March are availableThe split floor plan gives this property a unique advantage as it gives each couple unbeatable privacy. The master bed room has a comfy King bed with ...

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Property Type

Anna Maria Island House

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A Shore Thing

3 BR | 2 BA | Sleeps 8 | Quick View

$213

per night

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Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

This beach house is “A Shore Thing” for creating fantastic vacation memories. This newly furnished ground level home is decorated in coastal living motif and has no stairs to climb. The open floor plan is ideal for one or two families to have a fantastic vacation. The living room, Florida ...

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Property Type

Anna Maria Island House

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Jacaranda

3 BR | 2 BA | Sleeps 8 | Quick View

$199

per night

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Key Amenities

  • Air Conditioning
  • Pet Friendly
  • Private Pool

About this property

766 Jacaranda Road - Anna Maria- fl -34218 Unique 3 bedroom 2 baths with an upstairs bonus room close to the beautiful beaches if Bean Point and the Amazing Pine Ave.This beautiful 3 bedrooms 2 bathroom single family home is minutes from the white sands beach of Anna Maria Island. Only a short walk ...

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Property Type

Anna Maria Island House

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Peacock Place - Pet-friendly and very close to beach!

$242

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

It is always summer on Anna Maria Island!We have one of the most pristine, un-crowded beaches you will ever visit. Enjoy a champagne breakfast, Duffy's burgers for lunch, or cocktails at sunset! In addition, there are many other fabulous things to do here - Busch Gardens, Universal Studios and Disney ...

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Property Type

Anna Maria Island House

"Family visit"
Reviewed July 3, 2019

Peacock Place is a great place for family reunions. Plenty of space. Close to the beach. We loved it.

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North End of Anna Maria Duplex with heated pool!

2 BR | 1 BA | Sleeps 4 | Quick View

11

Distance to beach: 500 feet to Bean Point

$164

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

Two story duplex. Each unit is two bedrooms, one bathroom. Rent one or both.Shared heated pool, short walk to the beach and everything you need for your perfect Anna Maria Vacation.***Availability calendar does not distinguish between upstairs and downstairs units. Upstairs available: Downstairs ...

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Property Type

Anna Maria Island House

"Great place for a quiet vacation"
Reviewed June 20, 2019

This is a great place to vacation in Anna Maria, in a quiet well maintained neighborhood. We are looking forward to our next visit in 2020. This will be our eighth time staying at this property. Just ...

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Southern Comfort

3 BR | 3 BA | Sleeps 6 | Quick View

$153

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Southern Comfort is a private, single family home centrally located in Holmes Beach. This gorgeous 3 bedroom 2.5 bath vacation rental offers a private heated pool, front and rear balconies, gas BBQ grill, tropical landscaping, one car garage and much more! Just a brief 4 minute stroll to the pristine ...

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Property Type

Anna Maria Island House

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Manna-Tee Beach House

3 BR | 3 BA | Sleeps 8 | Quick View

$153

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Overview If you are ready to put your "heels in the sand", look no further. Manna-Tee Beach House is the perfect vacation spot for relaxation on Anna Maria Island. This beautiful 3 bedroom, 2.5 bath home located on Holmes Beach on Anna Maria Island has all the amenities for you. Top-of-the-line ...

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Property Type

Anna Maria Island House

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Relax at The Ulmer House...Right on the Beach...Gulf Views Everywhere!

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

As you drive up to The Ulmer House, the landscape is natural, graceful and compliments the house in an authentic way. It feels like a compound from the street looking through the mature trees that surround a very large property and shield it from the view of the public. There is a very private and spacious ...

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Property Type

Anna Maria Island House

"wonderful home in a beautiful location!"
Reviewed July 23, 2019

This home was beautiful and had everything we needed for a wonderful week at the beach. The shaded lot and views of the beach from the house were outstanding!

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Copacabana

3 BR | 2 BA | Sleeps 8 | Quick View

$213

per night

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Key Amenities

  • Air Conditioning

About this property

Copacabana is newly remodeled 3 bedroom, 2 bath private home that sits right on the canal in Anna Maria in a very quiet neighborhood. There is now a brand new kitchen for entertaining and new tile floors flow throughout and with a designer’s stylish touch, you will feel you have found your home ...

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Property Type

Anna Maria Island House

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Stunning Luxury Beachfront House W/Pool &Spa

$643

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

An outstanding luxury beach house furnished as our home to a very high standard. With a stunning beach coastal theme. It is located on the north end of Anna Maria island The house has 4 bedrooms and 4 bathrooms it was constructed in 2011 has been designed to accommodate a single family group. Please ...

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Property Type

Anna Maria Island House

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Walker Beach Cottage/Pet Friendly

$129

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Just what the Doctor ordered"
Reviewed October 7, 2019

This was the best vacation I have had in a few years. It was so easy to schedule - Libby the cottage manager was excellent and so accommodating. The cottage was charming, very clean, and well equipped ...

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Beach Vacation at Angelinos Sea Lodge on Anna Maria Island

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 100 feet to Beach onsite

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

Angelinos Sea Lodge offers four unique vacation rentals right on the beach of Florida Gulf Coast, Anna Maria Island, Holmes Beach. Hidden in a quiet residential street, these beachfront cottages are quaint, charming, and just a few steps to the white sand and blue sea. All beach cottages have direct ocean ...

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Property Type

Anna Maria Island Cottage

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Dans Florida Condos - 1 bedroom 1 bath (Private Beach Access) Runaway Bay

$129

per night

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Key Amenities

  • Air Conditioning
  • Full 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 ...

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Property Type

Anna Maria Island Condo

"Heated Pool!!!"
Reviewed May 13, 2019

Loved this unit and the excellent communication I had when booking with Dan's Florida Condos. The place had everything we needed, including beach towels & beach chairs. The heated salt water pool was awesome ...

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Summer Retreat

4 BR | 5 BA | Sleeps 12 | Quick View

$332

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Summer Retreat is an absolutely amazing, new custom luxury home nestled in the quiet residential area in the heart of Bradenton Beach. Offering 4 bedrooms/4.5 bathrooms. Each bedroom has a private bathroom. There is also a kids gaming room with Xbox and an arcade game. You will find that this home has ...

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Property Type

Anna Maria Island House

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Turtle's Bay

3 BR | 3 BA | Sleeps 6 | Quick View

1

$279

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

This brand new 3 bedroom 3.5 bathroom + den . This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, ...

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Property Type

Anna Maria Island House

"Beautiful Property"
Reviewed September 23, 2018

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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Sunset & Sand

4 BR | 3 BA | Sleeps 8 | Quick View

1

$299

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Brand New 4 Bedroom 3 Bathroom, Pool & SPA Garage & Bikes. Minutes from beach This brand new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard ...

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Property Type

Anna Maria Island House

"Great Thanksgiving Vacation!"
Reviewed November 26, 2018

We spent Thanksgiving week at Sunset and Sand and it delivered on all our expectations. The home is clean, beautifully decorated and functional. The kids absolutely loved the heated pool and Spa and Its ...

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Bahama Mama

3 BR | 2 BA | Sleeps 6 | Quick View

$184

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Overview This is it, paradise found. This fabulous Key West style elevated 3 bedroom 2 bath Anna Maria Island home has so many wonderful features it is hard to list them all here. It offers cathedral ceilings, open floor plan, private heated pool & spa, private decks from every room, screened covered ...

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Property Type

Anna Maria Island House

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Emerald Bay

3 BR | 3 BA | Sleeps 6 | Quick View

$279

per night

View Details

About this property

This brand new 3 bedroom 3.5 bathroom + den . This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, ...

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Property Type

Anna Maria Island House

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Sunset Landings 1

2 BR | 2.5 BA | Sleeps 4 | Quick View

$98

per night

View Details

Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

Watch the gorgeous Anna Maria Island sunsets from the comfort of your own balcony! This lovely 2 bedroom and 2.5 bathroom condo located on Bradenton Beach is just across the street from the pristine white sandy beaches of the Gulf of Mexico. With magnificent views of the Gulf waters, a fantastic location ...

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Property Type

Anna Maria Island Townhome

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Beach Bliss

3 BR | 3 BA | Sleeps 6 | Quick View

$225

per night

View Details

About this property

Incredible 3 Bed 3 Bath bungalow, Minutes From The Beach With Backyard OasisSpecial Rate does not include thanksgiving Christmas of New Years week This beautiful 3 bedroom 3 bathroom Bungalow is only minutes from the white sands beach of Anna Maria Island. Only a minute walk to the nearest free ...

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Property Type

Anna Maria Island House

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Casa Amiga

4 BR | 4 BA | Sleeps 10 | Quick View

$449

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

CASA AMIGOS is a brand new construction home that features 4 bedrooms and 4.5 bathrooms and a fantastic location-just a 10 minute stroll to the White sandy beaches of BEAN POINT on the coveted north end of Anna Maria. Less than 5 minutes walk to Pine Ave where you can grab your morning coffee, take the ...

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Property Type

Anna Maria Island House

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Paradise Found

6 BR | 6 BA | Sleeps 12 | Quick View

1

$349

per night

View Details

About this property

401 42 nd Street - Holmes Beach - FL - 34217 This brand new 6 bedroom 6.5 bathroom - SLEEPS 14 Comfortably. This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. ...

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Property Type

Anna Maria Island House

"Awesome vacation house."
Reviewed November 2, 2019

Great house for vacation. 6 bedrooms and bathrooms. Nice pool and hot tub. Already had friends interested.

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Sunset Beach

2 BR | 2 BA | Sleeps 4 | Quick View

$247

per night

View Details

Key Amenities

  • Air Conditioning
  • Pool

About this property

Lovely, beachfront 2 bedroom, 2 bath condo with a screened porch overlooking the beautiful sand beaches of the Gulf of Mexico!! Situated in a small complex with lush landscaping, private pool and covered parking.Sunset Beach 101 offers newly renovated bathrooms and kitchen with new tile throughout ...

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Property Type

Anna Maria Island Condo

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Seahorse Beach House

4 BR | 3 BA | Sleeps 8 | Quick View

$299

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

202 81 st Street - Holmes Beach - Fl 34217 This Beautiful new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the heated pool in your own backyard oasis. This house has every luxury you could ...

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Property Type

Anna Maria Island House

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Casa Del Mar

4 BR | 3 BA | Sleeps 8 | Quick View

1

$153

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

OVERVIEWCasa Del Mar is a beautiful Key West style home featuring four bedrooms and two and a half baths. This property is located on the north end of Holmes Beach close to shopping, restaurants and trolley stops. Best of all, this unit is within walking distance to the white sandy beaches. Amenities ...

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Property Type

Anna Maria Island House

"Casa Del Mar 74th Steeet"
Reviewed July 17, 2019

Loved this house for our stay. It was really nice, with comfy beds. The stairs cancelled out our calories! Loved this very nice house.One thing, it is time for new carpet. Also, door leading to upstairs, ...

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Flip Flops Forever

5 BR | 3 BA | Sleeps 10 | Quick View

1

$184

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

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 4 bedrooms/3 bathrooms. Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk (around 200 Steps) ...

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Property Type

Anna Maria Island House

"good location, across the street from the beach."
Reviewed March 25, 2019

Overall a wonderful experience. The beach is about a block from the house, close enough to not mind running back for bathroom or snacks. There are a few buckets and beach toys included, we left a few more. ...

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A Hart of the Gulf

3 BR | 2 BA | Sleeps 8 | Quick View

$81

per night

View Details

Key Amenities

  • Air Conditioning

About this property

Quaint 3 bedroom, 2 bath private home in a quiet area of Holmes Beach only a short walk from the beach. A Hart of the Gulf is ground level and spacious with all the comforts of home included. Close to the free trolley, shops and restaurants. Accommodates up to 8 guests Amenities include: Linens, central ...

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Property Type

Anna Maria Island House

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Real Gulf-Front Beach House - One Step to the Beach!

$300

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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

"Great home with a beautiful yard on the Gulf of Mexico"
Reviewed November 6, 2018

We stayed here for a week and had a great stay. This is an “Old Florida” home, not a super renovated McMansion. The House was full of charm and very clean and comfortable. There are several sitting ...

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Starfish Isle

4 BR | 3 BA | Sleeps 10 | Quick View

$249

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

At 4 bedrooms and 3 full bathrooms, this is one of the best rentals on Anna Maria Island. A few short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish Isle is a luxurious and welcome retreat in the perfect location ...

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Property Type

Anna Maria Island House

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Conch Out Beach House

4 BR | 3 BA | Sleeps 10 | Quick View

$329

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

At 4 bedrooms and 3 full bathrooms, this is one of the best rentals on Anna Maria Island. Straight down the road 1 block to the beach, and around the corner to restaurants, pubs & stores. Featuring a huge heated pool to relax in after your busy day, Conch Out Beach House is a luxurious and welcome ...

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Property Type

Anna Maria Island House

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The Salty Dog - North Shore

4 BR | 3 BA | Sleeps 8 | Quick View

$196

per night

View Details

Key Amenities

  • Air Conditioning

About this property

Welcome to The Salty Dog. This luxury Key West style home has it all. Expansive bay views, private heated pool, extra large master suite with a double shower and Jacuzzi tub, fresh and modern decor, two large balconies, indoor sitting area off the pool, and 2 car garage. The home is walking distance to ...

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Property Type

Anna Maria Island House

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Anna Maria Island Vacation Rentals

Anna Maria Island Weather

 | 

7423°  5211°
JANUARY
Ocean 6518°
7624°  5412°
FEBRUARY
Ocean 6518°
7926°  5714°
MARCH
Ocean 6820°
8328°  6116°
APRIL
Ocean 7423°
8831°  6719°
MAY
Ocean 7926°
9133°  7222°
JUNE
Ocean 8328°
9133°  7323°
JULY
Ocean 8529°
9233°  7423°
AUGUST
Ocean 8731°
9032°  7323°
SEPTEMBER
Ocean 8529°
8630°  6719°
OCTOBER
Ocean 8228°
8127°  6016°
NOVEMBER
Ocean 7624°
7624°  5412°
DECEMBER
Ocean 7021°

Choose a vacation rental on the little island that has it all

A mere 20 minutes from Bradenton, laid-back Anna Maria Island awaits. What feels like “old” Gulf Coast Florida with strict business regulations, little to no car traffic, and a peaceful way of life. That’s right, you won’t find any chain restaurants or high-rise, view-blocking buildings here. And oh, the beaches! A seven-mile strip of beautiful white-sand beaches line the barrier island of Anna Maria Island between the turquoise Gulf of Mexico and peninsular Florida. It won’t be difficult to unwind here.

Anna Maria Island has amazing beachfront with available accommodations for you. When staying in one of our Anna Maria Island vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Use the filters to narrow down your choices and choose the rental that calls to you, just like Anna Maria Island does.

Climate

You come to Florida for warmth and guaranteed clear skies. You’ll find all that and more in Anna Maria Island. The average year-round temperature in Anna Maria Island is a comfortable 75 degrees making it an ideal destination to visit during any month. You won’t see too much shifting of temps and precipitation here, though try to avoid hurricane season in the fall. Otherwise, you can’t go wrong whenever you visit.

Getting around

Hop around the island on the Anna Maria Trolley, as it runs north to south from the pier all the way to Coquina Beach. It stops every few blocks for riders to get on and off. Since parking is rare throughout the city, the trolley is a fan favorite. The best part? This scenic, air-conditioned ride is completely FREE!

Top activities and attractions

Your family won’t run low on things to do in Anna Maria Island. You’re visiting for the beaches, of course, and the best public one is known as Bean Point, located at the north end of the island. From here, you can walk around the entire island without leaving the sand. At the southern end of the area you’ll find Bradenton Beach which is another highly-rated, soft-sand place to spread your blanket and enjoy the sun. Of course a seaside city excels at water sports, too. Try your hand at parasailing, snorkeling, jet-ski, water ski, and many more activities on the turquoise blue waves.

Once you’re through with the surf, walk along the Anna Maria City Pier. Over 100 yrs old, the Pier offers up some great views of Tampa Bay and the Sunshine Skyway bridge at the northern end of the island. Visitors can see an array of birds and marine life, including dolphins and manatee. For more scenic and historic walking, check out Coquina Baywalk. This pleasant park is fun to explore. Winding boardwalks and trails along the water's edge, hidden in the mangroves.

The local museums and art galleries are popular attractions as well and great alternatives to outdoor activities. Spend an afternoon at the Anna Maria Island Historical Museum and Park. Visitors to the museum and park can learn about the island’s history, take part in a scavenger hunt, and tour the cottage that fell into the bay.

Shopping and dining

You’ll want to shop the day away on Pine Avenue, known as “the greenest little main street in America”. It’s lined with boutiques all the way up to the City Pier. Holmes Beach is also a populars shopping center ideal for grabbing that perfect souvenir.

Nestled alongside the storefronts are award-winning dining options. For those with a sweet tooth, The Donut Experiment serves up custom creations daily including a Fruity Pebbles inspired masterpiece. Yum! Fresh seafood abounds, like at the popular Waterfront Restaurant and upscale Blue Marlin Grill. For a taste of Europe, and German hops, visit Old Hamburg Schnitzelhaus serving up sausage, beer, and pretzels - each more delicious than the last.

Events

Although we discussed how the year-round flawless weather makes AMI an ideal choice no matter the month, time your trip to coincide with some popular area events to maximize fun. Heritage Day in February features the wares and skills of local artists and crafters, and attendees can take part in activities, enjoy lively music and participate in old-fashioned games for kids. Later in spring, the Bridge Street Merchants host the Blues, Brews & BBQ event to showcase the area’s top musical talents. Outdoor Market Sundays take place November through April with crafts and local produce for sale.

Anna Maria Island beach rentals on FloridaRentals.com

Booking Anna Maria Island rentals on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!