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Anna Maria Island Beachfront Rentals

(29 rentals)
New
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Reel Coastal PropertiesThe space Highlights • 2-minute walk to the Beach of Anna Maria Island • 5-minute walk to Pine Ave. • Private Pool • Outdoor Shower • Beach gear (chairs, umbrella, towel, kids toys)Blue Mermaid by Reel Coastal Properties 111 Sycamore Ave Anna ...

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$397
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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$328
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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$374
avg per night
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
24 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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$234
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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$563
avg per night

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Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
35 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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$265
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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$194
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
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
22 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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$234
avg per night
Anna Maria Island House
Sleeps 14, 5 bedrooms, 5 bathrooms
1 review

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 BR + 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep 14 with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! Email owner about our other property that sleeps ...

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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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$603
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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$238
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 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

"Cheerful Pelican was great!"

We stayed for 3 weeks, great location across from the beach, and walking distance to Bridge street. The layout of this condo has 2 patios, one in bedroom facing east watching sunrise, and the 2nd in living ...

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$212
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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$484
avg per night
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
34 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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$265
avg per night
Anna Maria Island House
Sleeps 16, 6 bedrooms, 4 bathrooms
3 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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$623
avg per night
New
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

The sparkling, blue waters of the Gulf of Mexico await you at 105 Tiffany Place. Located directly on Anna Maria Island's 7-mile long beach of pure white sand, our 2-bedroom condo is the ideal location for relaxing in the sand and soaking up the sun.Our home underwent a complete renovation during ...

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$320
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Absolutely beautiful monthly rental in highly sought after Holmes Beach on Anna Maria Island. If you are interested in dates blocked on the calendar, please message me. This 100% updated home has everything from a large heated pool, outdoor shower, lush mature landscaping, completely furnished inside ...

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Featured review

"Awesome House"

WOW! I can not say enough about the wonderful stay we had. The house was beautiful and stocked with everything a family would need and the location is perfect. Short walk to beach and Pine St. restaurants ...

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$324
avg per night
New
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Welcome to "A Wave From It All" – your perfect retreat on Holmes Beach, Anna Maria Island, FL. Nestled within a charming triplex, our end unit offers front-row views of the Gulf of Mexico, ensuring a truly unforgettable stay. With its unbeatable location, spacious accommodations, ...

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$243
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
6 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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$195
avg per night
Anna Maria Island Apartment
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

This 3 bedroom condo sits close to the Gulf Beaches at Gulf Place Condominium. Sit on the lanai and drink your coffee looking out onto the Gulf.

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$546
avg per night
Anna Maria Island House
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront

About this property

The Beach House is a charming beach bungalow nestled among numerous Australian pines and sea grapes. A unique setting directly on the Gulf of Mexico shaded among the trees. Walk out the back door on your private path to a white sugar-sand beach. Best of both worlds, you have the shade and sunny beach. The ...

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$545
avg per night
Anna Maria Island Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

About this property

2 bedroom 2 bath 1000 square feet condo with a beachfront view of the Gulf of Mexico on the quiet, peaceful Anna Maria Island. Walking distance to many restaurants and bars. 30 minutes away from the Sarasota/Bradenton airport. Free trolley to go anywhere on the island.

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Featured review

"Big Joe"

Awesome unit with great views and access to the beach as well as restaurants and grocery stores. I would definitely stay there again. Great time and relaxing vacation.

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$127
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 250 feet to About a 50 second walk

Key Amenities

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

About this property

This home was great before but now it's undergone a 2+ year no expense spared renovation making it exceptional in every way! Our newest 3 bedroom/3 full bathroom home is one of the most deluxe vacation rentals available on Anna Maria Island and located in most sought after part of island and only ...

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Featured review

"Excellent"

This house is in a great location close to the beach, the pier and bridge street. The kitchen is probably one of then best stocked I have ever scene. I highly recommend this house. Great indoor and outdoor ...

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$423
avg per night
Anna Maria Island Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

Click on calendar for available 2025 dates. Book now before they are gone! CALL FOR UNBELIEVABLE SAVINGS. ONLY PHONE CALLS GET DISCOUNTS. July 26- August 16th, 2025 is available now. Special rate is available.TWO WEEK MINIMUM STAY. No exceptions. No Pets. Sorry.20 STEPS TO THE SAND - GREAT ...

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Featured review

"Ok"

️ love this area one of my favorite places to stay AnnaMaria island.. love it .. can’t wait to go o back

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$245
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

NOTE - The pool will be closed for resurfacing starting in Mid July through the beginning of September.Welcome to Sun Plaza West 101! *Highlighted Amenities** Location! Gulf Front Resort Condo Community! * 2 Bedrooms / 2 Bathrooms * 1 King Bed & 2 Twin Beds (Or can make 1 King upon request) * ...

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$174
avg per night
New
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

30 day stays make this condo community wonderfully quiet and special. The view overlooks the big pool and the Bay. Bring your swimsuit, we are a short distance to AMI's famous white sand beaches, umbrella, beach canopy, cooler, beach towels, and chairs make for a perfect beach day and sunset and ...

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$209
avg per night
Anna Maria Island Apartment
Sleeps 4, 2 bedrooms, 1 bathroom
4 reviews

Distance to beach: 0.3 miles to Anna Maria Bay Front part

Key Amenities

  • Air conditioning
  • Beachfront
  • WiFi

About this property

Newly renovated with a modern European Interior designer for comfort, beauty and relaxation at its best.Million-dollar views with fantastic and serene sunsets and nature watching Best island location - north – and just at the end of Pine Avenue with walking distance to the City Pier, shops, ...

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Featured review

"Beautiful Property"

This property is located in a beautiful area! Very quiet and comfortable. Nice and clean…I highly recommend this property to anyone! You won’t regret it .

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$418
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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$232
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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$899
avg per night
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