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Luxury Vacation Rentals in Anna Maria Island

(57 rentals)
Anna Maria Island House
Sleeps 8, 5 bedrooms, 5 bathrooms
1 review

Key Amenities

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

About this property

Welcome to paradise! This beachfront blends modernity with relaxation to give your group a heavenly experience. Located in a prime location on the North End of Anna Maria Island, Cloud 9 has everything that your group needs for a perfect vacation. Each of the 4 bedrooms is professionally decorated and...

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Featured review

"Paradise!"

This home was perfect for our family vacation- great views, clean, well stocked, we will definitely be back! Thank you!

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$2,448
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5 bathrooms

Key Amenities

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

About this property

Luxury and the beach intersect at a point titled Serendipity Deux. This gorgeous 4 bedroom home offers all the allure of an extravagantly decorated space while giving you premium beach access and an ideal location. The Master Suite is located on the first level and comes outfitted with a king bed, tub...

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$2,500
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms
9 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

We have last minute openings available at 75% off! Act fast! Won't last! We have 5/1 to 5/5 available. 4 nights is just $222/night. Reduced from $1100/night! Also other periods Available at HUGE DISCOUNTS!! Other vacancies! Week of 6/26 $499/nt, 7/11-7/15 $250/nt. The week of 8/2 just $390/nt!...

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Featured review

"Beautiful Propery"

This property is perfect for a relaxing vacation. The owner has thought of everything to make your stay stress free and relaxing. It is close to the beach and restaurants. We loved our stay and are planning...

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$737
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Escape to Your Exclusive Tropical Retreat! Indulge in the privacy of your own backyard oasis, complete with a sprawling pool and a dedicated Beach Volleyball Court. Open the back gate and find yourself steps away from the pristine Gulf Beaches. This ground-floor haven offers unparalleled convenience,...

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$1,800
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Located in the heart of Holmes Beach on Anna Maria Island, this 4-bedroom, 5.5-bath coastal getaway is your dream vacation home — perfect for families, friends, or group trips.Short walk to the beach Private mini putt-putt + game room Heated pool + spa oasis Close to bars, dining, and...

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$918
avg per night

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Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Welcome to your Gulfside, bohemian escape! Serendipity Gulf’s minimalistic, peaceful approach to decor strips away all the unnecessary to leave you with a serene oasis out to the beach that lies just beyond the back door. The clean, white decor within the home leaves plenty of opportunity for your...

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$1,500
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 50 feet to across the street

Key Amenities

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

About this property

Key Lime Cottage – 880 N Shore Drive, Anna Maria Island3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet Friendly | Private Hot Tub | Fenced BackyardWelcome to Key Lime Cottage, a charming slice of island life nestled along the coveted North Shore Drive on Anna Maria Island. With room for up to...

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$745
avg per night
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