Anna Maria Island Vacation Rentals

(268 rentals)
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3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 0.1 miles to 30 seconds to your left

$601

avg/night

View Details

Key Amenities

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

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 ...

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Drive through the gated driveway with a manatee on it and you'll enter Manatee Retreat. This duplex is a private getaway on a canal! Unit A is separated by a fence so you have your own private retreat. This 2 bedroom/3 bathroom home has a mid-century modern vibe as you walk into a large living room ...

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

6 PERSON GOLF CART INCLUDED ON ALL RESERVATIONS! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle InsuranceEndless Summer is the latest addition to SeaBreeze Vacation's portfolio. Pristine, newly constructed home features 7 beds/6 ...

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

In the heart of Holmes Beach on Anna Maria Island rests this charming home just steps to the beaches. The home creates fun Florida island vibes with two bedrooms perfect for a family or a small group getaway. Anna Maria Hideaway lies within a stone's throw of the trolley stops for guests to hop on ...

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Property Type

Anna Maria Island House

"great location"

We enjoyed on our stay at this well-kept property on Anna Maria Island. It offered privacy with a good central location.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Dreaming of an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Step outside your door and find our beautiful beaches; many local eateries; FREE rides on the Island trolley; unique boutique shopping or you can stay on site ...

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Property Type

Anna Maria Island Condo

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$235

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Beach Bellini is a 3 bedroom/3 bathroom private home in Holmes Beach. Just an 8 minute walk to the beach, pull into the paver driveway with a one-car garage and enter this light and airy home with wood floors and wood plank ceilings. The fully-stocked kitchen has stainless steel appliances, granite counters, ...

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Property Type

Anna Maria Island House

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$197

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Perfectly located 2 bedroom/2 bathroom condo is directly across the street from the gulf beaches. Pelican Cove is located in a small, private complex on a very unique part of the Island. It is one of the few condos with views of both the Gulf and the Bay. Pelican Cove is just 40 yards from one of the ...

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Property Type

Anna Maria Island Condo

"Great Stay"

We were actually supposed to stay in # 3,but ended up in #2. The condo was really really clean and we'll stocked. The appliances are up to date,and everything works. Plenty of glasses,pots,pans,utensils ...

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2 BR | 2 BA | Sleeps 4 | Quick View

5

Distance to beach: 100 yards to Manatee Beach

$314

avg/night

View Details

Key Amenities

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

About this property

Welcome to our home away from home on the breathtaking Anna Maria Island in the charming town of Holmes Beach Florida. Anna Maria is a barrier island on the Gulf of Mexico with an old time feel.Its only 7 miles long by 3 miles wide.Our condo is on the beach roughly 200 yds from the Gulf.We ...

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Property Type

Anna Maria Island Condo

"Perfect place"

We have stayed here several times over the last years. It is always immaculate inside. The kitchen is well stocked. The beds are very comfortable. It’s become our home away from home. The ocean is ...

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$282

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Take one step into this home and you will think you are dreaming! It's the epitome of coastal living because it's absolutely breathtaking! Bring your boat! Look straight out the sliders in the kitchen and you'll see an amazing crystal blue pool with a sun deck, artificial turf with a putting ...

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Property Type

Anna Maria Island House

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8 BR | 8.5 BA | Sleeps 18 | Quick View

4.8 rating on other travel sites

$970

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to “On the Rocks”! This professionally designed nautical themed home hosts 8 bedrooms and 8.5 bathrooms, plenty of space for large families or friends. This property has an elevator and is also pet-friendly. Bring your boat and fishing gear because On the Rocks is a waterfront home ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 4 | Quick View

4.9 rating on other travel sites

$259

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

**The Anna Maria Island Club pool will be closed for maintenance from 8/26 - 9/16.**Aqua Blu is a 2 bedroom/2 bathroom gulf front condo that offers everything you will need for a carefree getaway including a heated community pool and spa. From the moment you walk in, you are welcomed by stunning ...

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Property Type

Anna Maria Island Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool

About this property

When it's time to run away— to escape to a tropical island oasis where the bright sun is shining and the gentle sea breezes are endless— then it's time to book a stay at Runaway Bay 117. This cozy coastal hideaway is tucked within one of the most exclusive Anna Maria Island communities ...

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Property Type

Anna Maria Island Condo

"Great location!"

We've been on Ana Maria Island before; it's a lovely area. This was a great location for us and the management was very prompt and considerate whenever we contacted them. Thank you so much!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Get ready to pack your bags because you'll be escaping to a tranquil oasis nestled within a lush tropical backyard, where a shimmering pool and soothing spa await your relaxation. Discover the serene charm of A Bean Point Paradise, a retreat boasting 5 bedrooms and 4.5 bathrooms with parking for ...

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Property Type

Anna Maria Island House

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4 BR | 4 BA | Sleeps 12 | Quick View

4.6 rating on other travel sites

$547

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 12 people with the add-on of the sleeper sofas. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool, and an EV Charger. Upon entry in ...

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Property Type

Anna Maria Island House

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3 BR | 2 BA | Sleeps 7 | Quick View

2
last minute deal
LAST MINUTE DEAL 7/9 - 8/20: Openings starting August 12th!!

$227

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to "Lazy Manatee" at Bradenton Beach Club, where even the manatees envy the level of relaxation we offer! This spiffy condo boasts three bedrooms and two full baths, giving you more space than a hermit crab's dream home. New decor, furniture and paint!At Bradenton Beach Club, ...

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Property Type

Anna Maria Island Condo

"Amazing condo"

This spacious condo appears to have been very recently completely renovated and extremely nicely updated. The large space was perfect for our group and we could have easily and comfortably added a couple ...

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DEAL

$1082

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Get ready to be swept off your feet by the charm and luxury of Winding Waves, your dream vacation spot right on the beautiful Anna Maria Island. This dazzling nine-bedroom, eight-and-a-half bathroom beachfront home is all about fun in the sun and upscale relaxation!Splash and Play Outdoors: Dive ...

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Property Type

Anna Maria Island House

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$179

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Runaway Bay condominium located on northern Bradenton Beach, is a comfortable 2 bedroom/2 bath second level condo located in a very popular complex. Runaway Bay is a bayfront complex, Unit 201, is only a few steps away from the beautiful beaches offering you all of the conveniences you would want in an ...

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Property Type

Anna Maria Island Condo

"Excellent beach vacation"

Such a pleasant stay, great location for walking to restaurants, shops, steps from the beach. We loved staying on the island it's been years since we've been and really appreciated all that it has to offer. ...

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$196

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Looking for a prime location to vacation? Seagrass Flats Unit 1 is a 2 bedroom/2 bathroom condo that is located less than 75 steps to the Gulf and has a shared heated pool. This unit has been completely renovated both inside and out. Bathrooms and kitchen feature quartz countertops, vinyl plank flooring ...

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Property Type

Anna Maria Island Condo

"Outstanding!"

We enjoyed our stay at Seagrass Flats. Our unit was very clean, well furnished, and worked great for our vacation with the in-laws. Beds were comfy and we appreciated the little extras, like beach towels ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Drive through the gated driveway with a manatee on it and you'll enter Manatee Retreat. This duplex is a private getaway on a canal! Unit B is separated by a fence so you have your own private retreat. This 2 bedroom/2 bathroom has a large living room with plenty of seating for you and your guests. ...

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Property Type

Anna Maria Island House

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2 BR | 2 BA | Sleeps 6 | Quick View

23
last minute deal
LAST MINUTE DEAL 7/9 - 8/20: Aug 17th - 31st open! 7 night min, flexible check in/ out dates!

$183

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. There are only 4 units in the complex so to pool is "semi private".This beautiful unit sleeps six with a king ...

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Property Type

Anna Maria Island Condo

"5 star experience"

My family enjoyed this vacation rental for a glorious week. The place was so comfy and inviting. They really thought of everything when it came to the overall experience. The property offers a nice peaceful ...

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DEAL

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Bring your family and guests to this 2-unit house! About 40 steps to the beach entrance of Anna Maria white, sandy beach, this home combined boasts 5 bedrooms, a sleeper sofa and 5 bathrooms. Bean Point Unit A boasts 3 bedrooms/3 bathrooms, while Unit B has 2 bedrooms/2 bathrooms. Both units feature well-equipped ...

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Property Type

Anna Maria Island House

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3 BR | 2.5 BA | Sleeps 8 | Quick View

1

$333

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Casa Bonita is bright, inviting, and the perfect place for a wonderful vacation with family and friends in a tropical paradise. This home is located in the heart of Bradenton Beach, only a few short steps away from beachfront access and Bridge Street. You can lounge in the sun and enjoy a swim in your ...

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Property Type

Anna Maria Island House

"Perfect"

The house was absolutely perfect! It was so nice and the cleanest house we have ever rented. We had everything we needed. We would definitely recommend.

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$196

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Looking for a prime location to vacation? Seagrass Flats Unit 2 is a 2 bedroom/2 bathroom condo that is located less than 75 steps to the Gulf and has a shared heated pool. This unit has been completely renovated both inside and out. Bathrooms and kitchen feature quartz countertops; vinyl plank flooring ...

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Property Type

Anna Maria Island Condo

"Would stay again"

I want to start by saying the accommodations were nice and the location is excellent. We would stay here again. The rest of my comments or for the rental company, owner and future renters. The check in ...

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$338

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Located just a few sandy steps from the turquoise Gulf of Mexico, Seaglass Cottage is the Anna Maria Island beach house you've been dreaming about. This quintessential beachfront bungalow has a footpath across the street that leads directly to the sugary white sand of Bean Point — one of the ...

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Property Type

Anna Maria Island Cottage

"Great place!"

Super cozy! Great place for a perfect vacation! Definitely will be one of my choices when we plan our next vacation!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Longing for an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Just steps outside your door you will find our beautiful beaches; many local eateries; FREE rides on the Island trolley; unique boutique shopping or you can stay ...

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Property Type

Anna Maria Island Condo

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$233

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool

About this property

Condo-cottage with Old Florida charm..... Welcome to paradise.....This updated cottage is within a small resort, just steps from a beautiful private gulf beach. Drive into the Tradewinds Resort, and you will find quaint, pastel colored cottages on both sides of you hidden behind lush tropical foliage. ...

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Property Type

Anna Maria Island Cottage

"Recommend for a quiet stay in a very homey environment. Very Satisfied."

We gave this 5 stars but my husband wanted to do 4 1/2. The reason he was disappointed that the dock and pier are set up for fishing, but the staff knew nothing about it. Also, seems like it would be smart ...

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$753

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Come stay at From Dusk 'Til Dune! This home is a recently built beach residence offering rooftop water views just one block away from the Gulf of Mexico beaches. This 5 bedroom, 5.5 bathroom, pet-friendly vacation haven is brimming with amenities. Its stunning backyard features a private pool, hot ...

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Property Type

Anna Maria Island House

"Serenity on the Water"

The condo was only surpassed by the view, which included a nightly explosion of sunset glory over the sound. If one wanted to be closer to the sun from the beach, the club directly on the gulf was only ...

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1 BR | 1 BA | Sleeps 3 | Quick View

1

$193

avg/night

View Details

Key Amenities

  • Air conditioning

About this property

Welcome to “Barefoot Mermaid 4” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop ...

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Property Type

Anna Maria Island Apartment

"Perfect location."

Perfect 1-bedroom apartment, only a steps away from the beach! Perfect location within walking distance to everything on Pine Street.

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$248

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Pelican Cove is a beautiful Gulf to Bay property with a prime location just steps to the beach, five-star restaurants, shops and more - it's the tropical vacation you've been dreaming of offering you all of the conveniences you would want in an island stay. This beautiful condo was completely ...

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Property Type

Anna Maria Island Condo

"Great Island Location"

Clean, cute updated condo. Photos represent the property correctly. Great view of the bay, right on the water. Only a short walk across the street to the beach. Easy walk (5 blocks) to great shopping ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Paradise Found is a recently remodeled and renovated 2 bedroom/2 bath duplex with its own private heated pool & spa. This property is centrally located on Holmes Beach and only a few minutes walk to the white sandy beaches. Upon entry, you have the living room with all new furnishings, where you can ...

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Crisp, clean, and completely remodeled— this 2 bedroom townhome is the perfect spot to make unforgettable Anna Maria Island memories. The warm sand and turquoise water of the Gulf of Mexico are right across the street. You'll be steps away from the beach and a quick stroll or bike ride from ...

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Property Type

Anna Maria Island Townhome

"Great for families!"

Great unit, excellent communication, comfortable beds! Kids utensils, pool/beach toys, pack n play, and toddler bed rail all there!

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2 BR | 2 BA | Sleeps 4 | Quick View

4.5 rating on other travel sites

$259

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

**The Anna Maria Island Club pool will be closed for maintenance from 8/26 - 9/16.**This amazing beachfront 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 ...

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Property Type

Anna Maria Island Condo

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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!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 ...

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Property Type

Anna Maria Island House

"Great Two Weeks in Holmes Beach"

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Vacations can be exciting and so overwhelming. Don’t worry, we’re here to help. Pack your bags and get ready to enjoy our beautiful island. This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Just steps outside your door you will ...

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Property Type

Anna Maria Island Condo

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2 BR | 1 BA | Sleeps 4 | Quick View

$220

avg/night

View Details

Key Amenities

  • Air conditioning

About this property

Welcome to “Barefoot Mermaid 1” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop ...

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Property Type

Anna Maria Island Apartment

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5 BR | 4 BA | Sleeps 8 | Quick View

$546

avg/night

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About this property

Mia BellaMia Bella has been completely restored and updated, creating one of the most unique and spacious residential properties on Anna Maria Island. The property is located on a deep water canal with over 80 feet of private patio running alongside mature mangroves. A new heated swimming pool is ...

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Property Type

Anna Maria Island House

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2 BR | 1 BA | Sleeps 6 | Quick View

4.7 rating on other travel sites

$167

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Relax, unwind, and make the best beach memories in this beachy home! This home has a fully-equipped kitchen that will make preparing meals easy. Spend time grilling on the private patio after a day of fun on the beach.You are just a seashell's throw from the white sands of the Gulf of Mexico, it ...

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Property Type

Anna Maria Island Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

4
last minute deal
LAST MINUTE DEAL 7/5 - 8/16: Fall openings!

$169

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool

About this property

Relax with the whole family at this peaceful place to stay.Endless Summer is two bedroom, two bath condo located on Anna Maria Island. Specifically, located in Runaway Bay on Bradenton Beach.We have beach wagon. umbrella, chairs and cooler for your use. This unit is ground level, no stairs!Endless ...

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Property Type

Anna Maria Island Condo

"Great Place, Perfect Location"

My husband and I recently stayed at this condo while visiting family and friends. This was the perfect condo and perfect location for us. Unfortunately, the pool was down for repairs of some sort but we ...

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DEAL

9 BR | 8.5 BA | Sleeps 8 | Quick View

2

$1067

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Compass Rose, a captivating residence offering deluxe amenities including a lazy-river-style pool with a hot tub, a game room, an elevator and a rooftop deck boasting amazing views of the Gulf of Mexico. This 9 bedroom, 8.5 bathroom, pet-friendly abode is an ideal beach retreat suitable for multiple families ...

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Property Type

Anna Maria Island House

"Great location"

Very clean and comfortable. Easy walk to everything you need and want to do. I would stay there again and highly recommend.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This cozy beach condo has been updated and features a lovely open floor plan, 2 bedrooms/2 bathrooms as well as a lanai ideal for enjoying quality time together after a fun day at the beach. The outdoor closet offers beach chairs, a beach cart, beach umbrellas and toys for the littles ones to enjoy. Everything ...

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Property Type

Anna Maria Island Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

2
owner special
Owner special: New reduced rates!!

$149

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This spacious 2 bedroom condo is close to the beach and in the heart of it all. This stunning condo offers everything you want in a beach retreat. The unit has ample space your family. The open concept living area is perfect for entertaining, with a kitchen featuring all new appliances. You can also open ...

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Property Type

Anna Maria Island Condo

"Great vacation rental!"

My husband and I rented this condo, Sand & Surf, from Owner, Morgan Henderson, and we were completely pleased with the accommodations. Morgan was wonderful about replying immediately to any questions we ...

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8 BR | 6.5 BA | Sleeps 18 | Quick View

1

$1590

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Paradise Beach lives up to its name! Nestled directly on the pristine soft white sands of Bradenton Beach, this remarkable property boasts 8 bedrooms, 6.5 bathrooms, and is pet-friendly. Complete with an elevator, it comfortably accommodates up to 18 guests. Bring your family and friends along to experience ...

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Property Type

Anna Maria Island House

"Margaritaville Themed Paradise with 2 King Beds & Incredible Lanai!"

Truly an amazing resort and we loved staying in Sunset Seacret! Our family enjoyed every minute! We looked hard to find a beautiful, safe, clean, beachy condo with 2 king beds, as we were vacationing with ...

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4 BR | 3.5 BA | Sleeps 8 | Quick View

1

$385

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Pet friendly
  • Private pool

About this property

Summer Breeze is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3.5 bathrooms. There is also a den where the kids can hang out with a TV and sleeper sofa. You will find that this home has everything you need for your perfect Anna Maria Island vacation! ...

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Property Type

Anna Maria Island House

"Nice house"

This house was nice, clean and well stocked. The furniture was a bit worn but very comfortable. The yard is small but nicely landscaped and the pool was large enough for our family. The walk to the beach ...

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4 BR | 3.5 BA | Sleeps 8 | Quick View

last minute deal
LAST MINUTE DEAL 7/11 - 8/22: Discounted August Dates Now Available!

Distance to beach: 0.1 miles to Bean Point

$753

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Views, views, views! Experience the peace and beauty of the North end of Anna Maria from this sprawling luxury home named for its spectacular porches and outdoor space.*Features include** Ultimate luxury vacation home with elevator^ * Private heated pool and backyard oasis * Poolside lounge, ...

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Property Type

Anna Maria Island House

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DEAL

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The View at the Bradenton Beach Club offers panoramic views of the Gulf of Mexico and beautiful beaches from the living room, primary suite or private screened balcony. The condo is part of the Bradenton Beach Club that provides the very best in vacation accommodations. Amenities at the BBC include two ...

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Property Type

Anna Maria Island Condo

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$451

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Bodacious Oasis! This exquisite property boasts 3 bedrooms plus a Den and 2.5 baths, comfortably accommodating up to 7 guests. Families will revel in the spacious open floor plan, offering ample space to relax amidst stylish island furnishings and entertainment amenities.The guest rooms ...

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Property Type

Anna Maria Island House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Kai Blue is located in Holmes Beach, just steps from the beautiful AMI beaches. This 4 bedroom/2.5 bathroom with an elevator also has a private backyard with a pool. Kai Blue gives you the dreamy coastal vibe and it's close to restaurants, Island stores and right next to the free trolley stop.Pull ...

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Property Type

Anna Maria Island House

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3 BR | 2 BA | Sleeps 6 | Quick View

4.7 rating on other travel sites

$213

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Bradenton Beach Club is a beautiful Gulf to Bay property that is 1/2 a block away from the sandy white beaches offering you all of the conveniences you would want in an island stay. This beautiful condo sleeps up to eight people with 3 bedrooms, 2 bathrooms, washer/dryer, elevator from the covered/lighted ...

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Property Type

Anna Maria Island Condo

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4 BR | 2.5 BA | Sleeps 8 | Quick View

2

$242

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Casa Del Mar is a beautiful Key West-style home featuring 4 bedrooms/2.5 bathrooms. 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 also include heated pool, ...

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Property Type

Anna Maria Island House

"74th Street"

This is a great place to stay! Easy walk to the beach. Super nice rental. Seabreeze was responsive to all questions and concerns.

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$201

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Sunset Azul is a 2 bedroom/1 bath gulf-side ground level villa on the southern end of Holmes Beach. This unit has just been completely updated (October 2019) with all new floors, paint and beautiful coastal furnishings. It's quiet, yet close to shopping, restaurants and trolley stops. Best of all, ...

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Property Type

Anna Maria Island Condo

"Beautiful place - Highly recommended!!"

This is a great condo!! Full kitchen, washer and dryer IN unit, comfortable bed and beautiful natural light throughout. Only a 2 minute walk to the Gulf beach, Walgreens and Public. 2 parking spots are ...

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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°

Enjoy the Perfect Anna Maria Island Getaway


Looking for a gorgeous and relaxing Anna Maria Island vacation rental without leaving the Florida coast? Anna Maria Island is the perfect vacation spot for you. Anna Maria Island is located on Florida’s western shore, just a few miles south of St. Petersburg.

This small, quaint island is separated from mainland Florida by the waters of Palma Sola Bay and Anna Maria Sound. However, the coast is connected to the island by way of U.S. Highways 64 and 684, making it easy to travel between the two. Despite its size, Anna Maria Island is packed with activities to enjoy and many gorgeous rental homes.

With FloridaRentals.com, you can live like a local while on your vacation by enjoying authentic architecture from the inside out within Anna Maria Island’s residential neighborhoods.

Hotel stays can be enjoyable, but there’s nothing quite like a high-quality rental home while on vacation. Not only will your trip feel more immersive within Anna Maria Island’s unique energy, but you will also be able to truly relax while on your trip.

There is no worrying about sharing a wall with strangers or lacking privacy. Additionally, you’ll be able to relax in a private backyard with some much-needed peace and quiet. Many Anna Maria rentals with FloridaRentals.com even feature unique amenities like pools, hot tubs, entertainment centers, walkable beach access, and much more.

Anna Maria Island Travel Tips


If you’re planning a trip to Anna Maria Island, you should keep a few key details in mind. The first is which airport you plan on flying into. Anna Maria Island is reachable by car from many of Florida’s largest cities, including St. Petersburg, Clearwater, Tampa, and Sarasota. However, depending on where you live, traveling to Anna Maria Island by plane might be easier.

There is no airport on the island, so you will have to fly into a nearby city and rent a car or take public transport from there. The closest commercial airport to Anna Maria Island is the Sarasota Bradenton International Airport, which is about 16 miles south of the island.

The St. Pete-Clearwater International Airport can also connect to Anna Maria Island via I-275 across Tampa Bay. This option is less convenient as this airport is about 45 miles north of the island. However, by flying into St. Pete–Clearwater, you could bundle multiple popular Florida destinations into one trip by taking the “long way.”

Another detail to keep in mind is the climate. Though many Florida cities experience warm weather throughout the year, the best time to enjoy the outdoors with warm yet pleasant temperatures on Anna Maria Island is mid-spring or fall. During these times of the year, average temperatures are between 80 and 85 degrees Fahrenheit, and chances of precipitation are low.


Best Eats on Anna Maria Island


There are many incredible restaurants and bars on Anna Maria Island, many featuring beachfront views. Rod and Reel Pier is a great example. Located on the northernmost tip of Anna Maria Island with a full menu of seafood and cocktails.

City Pier Grill and Bait, located on the end of Anna Maria Pier, is another great local spot for a meal with family, drinks with friends, or a romantic date. The delicious globally-inspired seafood dishes are complemented by the gorgeous view of Tampa Bay, which is especially breathtaking at sunset.

As you travel farther south down the island, there are many more eateries to explore during your visit to Anna Maria Island. Scott’s Deli is a great choice for fresh and delicious sandwiches if you’re looking to grab something quick to take for a picnic lunch on the beach.

Nearby are Duffy’s Tavern and Freckled Fin Irish Pub, two local bars that serve their own unique menus of American favorites and ice-cold drinks. If you’re looking for a more upscale after-dinner drinks experience, The Doctor’s Office is a hip cocktail bar in central Anna Maria with plenty of imaginative cocktails and light bites to enjoy. And yes, the building used to be a real doctor’s office!


Things to Do Near Anna Maria Island Vacation Rentals


Despite its small size, there is a huge variety of beaches to explore near Anna Maria Island rentals. Manatee Public Beach, located on the southwestern side of the island, is a popular destination for white sand, warm waters, and plenty of fun in the sun.

As you travel even farther south to the neighborhood of Bradenton Beach on Anna Maria Island, you’ll find spots like Coquina Beach, which wraps around the southern tip of the island. For prime beach access on the island’s northernmost tip, Bean Point Beach and Bayfront Park are two of the most popular. Many of the island’s beaches have a variety of amenities, such as playgrounds, volleyball nets, picnic tables, and concession stands.

The many Anna Maria Island piers are a special way to experience the beauty of the area from the water (without getting wet!). Some of these include Rod and Reel Pier, the Anna Maria City Pier, and Bridge Street Pier. Visitors can find local art and culture, gift shops, restaurants, and stunning views at any of the island’s piers.

Aside from taking a stroll along a pier, there are many other ways to experience the shimmering waters of Tampa Bay or the Gulf of Mexico. One popular activity for vacationers is to rent a boat or kayak from one of the many vendors along the island’s shores.

One of Anna Maria Island’s most popular rental shops is Beach Bums. At Beach Bums, you can rent kayaks and paddle boards for the whole family or even book a special kayak tour led by an experienced local. Need a break from the water? You can also rent bicycles or golf carts to explore Anna Maria Island by land!

Experience Bliss on Anna Maria Island


Adventure is waiting for you on Anna Maria Island. Make the most out of your adventure by vacationing at a luxurious private home, courtesy of FloridaRentals.com.


FAQ

How many vacation rentals are there in/around Anna Maria Island?

There are 268 Anna Maria Island vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Anna Maria Island?

There are vacation rentals available in Anna Maria Island for as low as $123 per night with an average price per night of $350.

Can I find a vacation rental in Anna Maria Island?

Yes, you can find vacation rentals in Anna Maria Island close to Holmes Beach, Coquina Beach, and Bradenton Beach. Don't forget to stop in to Bean Point or Manatee Public Beach.

Do any vacation rentals in Anna Maria Island have a pool?

Yes, there are 128 vacation rentals with a pool in Anna Maria Island on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Anna Maria Island vacation rentals on the ocean?

There are 20 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!