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Anna Maria Island Vacation Rentals

(272 rentals)
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
25 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • WiFi

About this property

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!Sailfish Gulf Suites is comprised of 4 separate suites. Suite 4 has garden views and is just a few steps to the beach.It features 1 bedroom with king size...

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$326
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, laid back way of life on the north end of the island being only steps to the gorgeous bayside beach with city park or a 5 minute walk to the world renowned Bean Point! You are also...

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Featured review

"The perfect getaway"

The entire stay was above all expectations. It was my wife's birthday. We invited friends from out of town to celebrate with us. The place was roomy and very comfortable. The kitchen is fantastic with the...

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$1,239
avg per night
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
25 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • WiFi

About this property

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!Sailfish Gulf Suites is comprised of 4 separate suites. Suite 3 has garden views and is just a few steps to the beach.It features 1 bedroom with king size...

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$326
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This stylish 3 bedroom, 2 and a half bath vacation home is located just a short walk from Anna Maria Island's sugar white beach. Gone Coastal 3 is amazingly updated and chic!*Features include** Super close to the beach * Heated private pool * Outdoor shower * Tiki Bar with games and...

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$599
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to Cheerful Oasis – Your Bay-to-Beach Escape!Discover the ultimate island retreat at Cheerful Oasis, a delightful 2-bedroom, 2-bathroom condo perfectly situated for your next getaway. Nestled just off the walking trail to the Marina, Bridge Street, and Bradenton Beach, this serene haven...

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$302
avg per night

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Anna Maria Island House
Sleeps 10, 4 bedrooms, 3.5 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Discover Your Perfect Beach Retreat at Bimini Breeze!Pack your bags (and some sunscreen) because you’re about to dive into an unforgettable getaway at Bimini Breeze! This stunning elevated home is just steps away from the pristine beaches of Anna Maria Island. With four bedrooms and three and...

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Featured review

"Exceptional stay!"

What a great home to visit on your Anna Maria Island vacation! Everything was exceptional and we made tons of great family memories together here. Highly recommend!

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$507
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
9 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Smuggler’s Cove Resort is a family friendly timeshare property that offers studio and one-bedroom units. PLEASE INQUIRE AS TO AVAILABILITY OF UNIT TYPE, AS WE ARE UNABLE TO DELINEATE ON WEBSITE, THANKS! Each studio unit sleeps two with a queen-size bed and has a full kitchen. One-bedroom units...

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Featured review

"Great place to stay"

We recently stayed in one of the bay side units for vacation. This place is the best of both worlds. We had a view of water from our balcony but the private beach for the ocean was right across the road....

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$204
avg per night
Anna Maria Island Condo
Sleeps 7, 3 bedrooms, 2 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to "Blue Skies" at Bradenton Beach Club!Discover your perfect getaway in this beautifully updated three-bedroom, two-bath condo, designed for families and friends looking to unwind in style. With coastal decor and modern furnishings, you’ll feel right at home from the moment...

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Featured review

"Beach Lovers Condo"

This condo has everything you need for the perfect vacation and then some. The location is what I thought was the best part of staying here. A short walk and before you know it, your on a beautiful white...

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$441
avg per night
Anna Maria Island Villa
Sleeps 8, 4 bedrooms, 4 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Are you dreaming of mornings by the pool and evenings watching sunsets on the sand? Are you travelling with little ones and need baby gear ready and waiting for you? Are you ready to trade your everyday routine for an unforgettable island escape?If this sounds like you, we’d love to welcome...

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Featured review

"Beautiful house and Celine is an excellent host"

Beautiful house and Celine is an excellent host. We stayed here a week for a family vacation and really enjoyed our time. House had everything we needed and more. Very clean and super close to the beach....

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$753
avg per night
Anna Maria Island Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Brand New Listing! Hello Sunshine...Take time and breathe again at this special and tranquil getaway. This 1 bedroom 1 bath corner unit is in a charming beachside complex with a lovely pool & gardens directly across & just 20 steps from the beautiful beaches of Anna Maria Island & the sparkling...

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$284
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This beautiful property offers a perfect blend of indoor and outdoor living, with welcoming accommodations for a maximum of 6 guests, all just a short walk to the pristine white sand beaches and centrally located on Anna Maria Island!The decor is a perfect blend of coastal elegance and comfort, featuring...

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$602
avg per night
Anna Maria Island Apartment
Sleeps 4, 1 bedroom, 1 bathroom
33 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This 1 BR, four-guest, condo strategically placed within short walks to the Beach (900ft, 275M), Marina (150ft, 46M), Historic Bridge Street (800ft, 245M), and Pier (1,056ft, 322M) will keep you CHEERFUL your entire stay! Coastal amenities: front screened lanai, heated pool, beach toy closet (including...

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$241
avg per night
Anna Maria Island House
Sleeps 14, 5 bedrooms, 5 bathrooms
2 reviews

Distance to beach: 0.1 miles to Bayside Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Newly renovated December 2024, with state of the art finishes! 5 King BR, 1 also has a Daybed + 2 King Sleeper Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep 14 total with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! 3 King Bedrooms...

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Featured review

"Family holiday"

Fabulous location and spotlessly clean family villa with every conceivable convenience to hand. Fitted our purposes exactly and the addition of the kayaks, boat and bikes/golf cart if you wanted them was...

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$863
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

What You'll Love About This Home:Location! 3 Blocks to the Beach! 4 Bedrooms / 4 Bathrooms 3 King Beds, Two Sets of Bunk Beds with Twin Bed over Full Bed Lagoon Style Heated Pool w/ sundeck & Spa In Pool Umbrellas Pool Deck Lounge Chairs Poolside Covered Lounge with Patio Furniture,...

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Anna Maria Island House
Sleeps 16, 6 bedrooms, 4 bathrooms
4 reviews

Distance to beach: 45 feet to Gulf of Mexico

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Enjoy breathtaking views of Egmont Key, Tampa Bay, and the Gulf of Mexico right from your doorstep! Walk straight ahead and you are on North Bay Boulevard Beach. Walk 4 more lots to the left and you are on Bean Point! Or walk 5 lots further left and you are on the Gulf of Mexico. Perfectly situated next...

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$952
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

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

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This newly redesigned elevated pet friendly 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...

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$867
avg per night
Anna Maria Island Townhome
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Bermuda Bay Unit 01 Gorgeous view of Beach 3 bd on Anna Maria IslandLocated in Bradenton Beach, this townhome is a dream. With 3 bedrooms including a king, queen, and bunk bed, guests will have plenty of space to unwind. Garage area has been converted into an entertainment area with ping pong and...

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$490
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Underwent complete INTERIOR REMODEL in Jan 2023!!! This Bean Point beauty is perfect for the family or group wanting to be ultra close & steps to one of the most beautiful sought after beaches in Florida! Aside from the fantastic location, this elevated 3 Bedroom 2 bath home has two amazing decks...

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$948
avg per night
New
Last Minute Deal
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Step into Sunset Shores, a sun-kissed three-bedroom, two-and-a-half-bath condo. Nestled on pristine Gulf sands, the condo is located in the Gulf front complex of La Casa Costiera where beach days meet upscale comfort, sunsets rival the last selfie of your trip, and every moment feels like a dream.Why...

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$478
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

- 7 min. walk to beach, beach chairs, umbrellas, towels, beach wagon provided- sleeps 4, 2 bedroom/2 bath, very private- On second floor with covered stairs. No elevator.- all linens provided, washer/dryer in unit- stores within short walk; Publix, Walgreens, CVS, Dollarama, Dunkin...

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Featured review

"Great condo!"

We enjoyed our stay! The condo was clean, spacious & inviting! The location was wonderful. We will definitely stay again. The owner was very quick to reply to my emails.

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$190
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the...

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$341
avg per night
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Relax in the modern 3BR 2.5Bath condo in the majestic beachfront neighborhood in Bradenton Beach, FL. Soak up the sun by the two community swimming pools, or walk down to the sandy beach and experience the beautiful Gulf Coast.The picturesque location will leave you speechless!The Space HURRICANE...

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$311
avg per night
Anna Maria Island Cottage
Sleeps 4, 2 bedrooms, 2 bathrooms
23 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Rentals by owner
  • WiFi

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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Featured review

"Absolute paradise!"

This year marks our 3rd time staying at Walkers cottage. (Would have been 4th time but the hurricanes took care of last year.) Absolute paradise! Literally 50 steps to the beach to set up your chair! Breath...

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$270
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 100 yards to Manatee Beach

Key Amenities

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

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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Featured review

"In the league with the best…"

We can testify that, although there are some great gulf front places on AMI, this is among them. The interior was terrific – from the premium countertops, tiled floor, and tastefully decorated interior,...

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$314
avg per night
New
Last Minute Deal
Anna Maria Island Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Mermaid Manor — a tranquil retreat on beautiful Anna Maria Island. This inviting duplex home is the ideal spot for couples, small families, or friends looking to enjoy the island’s sun-soaked charm and relaxed pace.Each level of the duplex are full floor units (lower and upper...

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$379
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Need a GREAT AMI GETAWAY? Just steps from the bayfront park in the City of Anna Maria is a charming island beach house called “La Cocolia” lovingly translated as the "little crab". This property is ready to host you and your family as you enjoy this newly renovated and decorated...

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Featured review

"Just right"

The property is centrally located on the island which makes it very convenient. It has everything you need, and was very clean. We would definitely rent it again.

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$460
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to The Cheerful Pelican – Your Perfect Beach-to-Bay Getaway!Discover the ultimate escape in this charming 2-bedroom, 2-bathroom retreat, perfectly nestled between the stunning Gulf beaches and tranquil bay waters. The Cheerful Pelican offers the best of both worlds with sunrise views...

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Featured review

"Perfect rental"

I came down with my 87 year old mom and sister. The unit was so clean and inviting. Had everything we needed for our stay. Love the porch facing the bay, and such a quick walk to the beach. My sister...

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$300
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Less than a minute's walk to the beach!Watch the sunset from the house!King sized bed in every bedroom.PARKING FOR ALL...Bring your boat or RV...Invite guests... There's room for everyone!Shell House is a two-story, 3-bedroom, 2-bath, multi-level fun-house on a extra large...

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Featured review

"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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$412
avg per night
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Escape to paradise in this beautiful 3-bedroom, 2-bathroom vacation rental home located just steps away from the white sandy beaches.The spacious living area is perfect for relaxing after a day at the beach, with comfortable seating and a large flat-screen TV. The kitchen is fully equipped with everything...

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Featured review

"Fabulous on beach condo"

This 3 bedroom, 2 bath condo in Holmes Beach was a fabulous place for our vacation of 6 retirees. From the spacious living area, open kitchen, sunny lanai, pool and good size bedrooms to being located...

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$466
avg per night
New
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Sailfish Nest, a beautifully remodeled 2-bedroom, 2-bath duplex located in the heart of Holmes Beach—just a short stroll from the pristine white sands of Anna Maria Island.Step inside to discover a thoughtfully designed, open-concept living space with all-new furnishings. Relax in...

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$472
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

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...

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Featured review

"Awesome!!!"

My family and I stayed at the cottage. House was perfect. It was nice that beach chairs and towels, etc. were available. We also enjoyed using the backyard and grill. The house is literally across the street...

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$355
avg per night
Anna Maria Island Villa
Sleeps 12, 4 bedrooms, 4 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Ideal Location - Family Vacation Accommodation 2 Individual Villas, 4 Bedroom 4 Baths Sleeping for 8-12 Guests Pricing is for one villaDuring January February & March you can only rent 1 villa. During June & July you must rent both villas. Pricing on our site here is for only 1 villa.The...

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Featured review

"Huge pool and awesome location"

We had a great time and our kids loved the pool! We rented bikes and used them everyday. We had a party of 12 and it was big enough for all. We would love to stay again!

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$337
avg per night
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
56 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Condo-cottage with Old Florida charm..... Fall discounts offered now through Dec 21: 20% off- Mon through Thurs Free night with 4 night stay, weekends included! I might be able to adjust the discounts so we can make it happen!!! Pet friendly- a welcome bag of treats, an AMI bandana, and a curated...

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Featured review

"Clean and Comfortable"

This adorable little cottage met our needs perfectly. Two adults on the king and two on the sofa bed, which was described as the most comfortable pullout couch they’d ever slept in. The kitchen was adequate...

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$246
avg per night
New
Special Offer
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Unwind in this bright and breezy 2-bedroom, 2-bath condo just steps from the beach. Enjoy a peekaboo ocean view from your private balcony and easy access to the sand, shops, and dining.Perfect for couples, families, or friends, the space features: * Two spacious bedrooms with plush beds (king and...

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Anna Maria Island House
Sleeps 10, 5 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

One of the highest rated vacation homes on Anna Maria Island with more than 160 five-star ratings from Airbnb/VRBO!Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated...

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Featured review

"Hidden paradise"

We were attending a beach wedding and made a vacation out if it. I connected with the owner Kath immediately. She was generous, attentive, available and without a doubt the best host we have ever met....

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$773
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 1.5 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

Shady Palms is a cozy secluded beach cottage right on the beautiful Gulf of Mexico. Walk out the back door to a white, sugar-sand beach and the sparkling Gulf waters. Shady Palms is the most perfect spot you'll ever find on the beach - have the best of both worlds - the sun and the shade.Beach...

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Featured review

"AMAZING!!!"

This house is the best rental we have ever stayed in! The scenery out back is incredibly relaxing.. trees, Adirondack chairs, the OCEAN!! It is so private, and also the best equipped kitchen I’ve ever...

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$517
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
13 reviews

Key Amenities

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

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the...

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Featured review

"Great Location and Spacious Condo"

We spent a wonderful month in this unit. You can see the beach from the front balcony as it's just across the street. It's very spacious with an open concept living room, kitchen and dining area. It...

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$387
avg per night
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
38 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • WiFi

About this property

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!Sailfish Gulf Suites is comprised of 4 separate suites. Suite 1 has direct views of the Gulf of Mexico and is just a few steps to the beach.It features 1...

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$370
avg per night
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
38 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • WiFi

About this property

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!Sailfish Gulf Suites is comprised of 4 separate suites. Suite 2 has direct views of the Gulf of Mexico and is just a few steps to the beach.It features 1...

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$370
avg per night
Anna Maria Island Condo
Sleeps 7, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

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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Featured review

"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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$326
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
24 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

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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Featured review

"Wunderschöne Wohnung"

Wir haben eine Woche in der Wohnung auf Anna Maria Island verbracht. Es war traumhaft schön. Die Wohnung ist sehr gut ausgestattet: vom Eiswürfelspender bis zur Waschmaschine, vom Strandwegen mit Stühlen...

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$298
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 4.5 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island!As you step through the front door, you enter a bright and...

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$934
avg per night
Anna Maria Island House
Sleeps 14, 5 bedrooms, 4 bathrooms
13 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

NEW MANAGEMENT...Welcome to Breathe Inn, your island escape where the sea breeze is plentiful and the relaxation comes naturally. This beautifully renovated 5-bedroom, 3.5-bath duplex with 2 kitchens invites you to exhale and settle into vacation mode. With two fully private units under one roof, it's...

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Featured review

"Breathe Inn"

Wonderful property and perfect for families with kids. The house was clean, well appointed with everything you could possibly need, and comfortable for everyone. The pool was always clean and well maintained....

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$761
avg per night
Anna Maria Island House
Sleeps 14, 6 bedrooms, 5.5 bathrooms
15 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

ASK US ABOUT MULTI WEEK DISCOUNTS!! Featuring 6 bedrooms 5.5 baths (sleeps 14) and a fantastic location - just a 1 minute walk to the white sands of the 65th St Beach Access!This vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining...

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Featured review

"Wonderful beach location"

Our party of 10 has stayed at this wonderful property multiple times and plan to come back. The house is in wonderful shape and has all amenities you could want including heated pool and hot tub with slide,...

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$1,269
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Featured review

"Excellent Stay"

Location was perfect! Condo had everything we needed, nicely decorated and clean. Morgan was wonderful to work with. Thanks Morgan!

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$206
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Gone Coastal, where every detail was carefully crafted for an unforgettable stay.*Features include** Private saltwater pool * 2 bedrooms and 2 full bathrooms * Queen sleeper sofa - sleeps 6 total * Stainless appliances * Keurig coffee maker and regular drip coffee maker *...

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Featured review

"Perfect beach location with beautiful interior"

This duplex includes stunning beachy interior decorating, great location (quiet neighborhood with an easy walk to a white sands beach) with a bonus heated pool with outdoor shower, which was ideal after...

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$396
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Buckeye Haven is situated in one of the most sought after communities on Anna Maria Island. Playa Encantada is a tropical beach front community with the white sandy beaches of Anna Maria Island! This popular destination is sure to please beach goers, as well as tennis and pickleball enthusiasts. The...

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$262
avg per night
Anna Maria Island Condo
Sleeps 8, 4 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Beachfront Holidays are the gift everyone loves! Celebrate the season steps from the beach at Island Suites Unit 1. The island charms you with music, holiday lights, festive eats, shops, and holiday cheer - providing the perfect atmosphere for an unforgettable holiday together. Relax on our large screened...

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$457
avg per night
Last Minute Deal
Anna Maria Island Condo
Sleeps 5, 2 bedrooms, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Palm Cay unit 10 is a two bedroom , one bath condo just 50 steps from the pristine Gulf waters of Homes Beach. There is a shared pool centered in a courtyard surrounded by lush , tropical vegetation. There is a double sofa bed in the living room. The kitchen is fully equipped , including a coffee...

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Featured review

"Enjoyed it very much."

The unit was lovely. Well equipped and very clean. The pool area is very nice and a 1 minute walk to a beautiful beach.

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$239
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
8 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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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$246
avg per night
Full map
Map

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°

FAQ

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

There are 272 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 $115 per night with an average price per night of $394.

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 193 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 22 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!