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Anna Maria Island Vacation Rentals with Private Pool

(207 rentals)
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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$1,065
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 6 bathrooms

Key Amenities

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

About this property

Welcome to Shangri-La, an idyllic vacation rental nestled on the exclusive tip of Anna Maria Island at Bean Point. This luxurious, fenced, and gated private property offers an escape from the everyday, inviting you to unwind and rejuvenate in a setting of unparalleled beauty and comfort. Available for...

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$4,000
avg per night
Anna Maria Island Bungalow
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The Blue Haven by Beach Retreats Vacation Rentals 322 64th Street Holmes Beach, Anna Maria Island VRC25-000096 2 Bedrooms | 2 Bathrooms | Sleeps 6 | Heated Pool This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighbors Please note: The pool technician will need to...

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Featured review

"Wonderful stay!"

This was our first time on Anna Maria and we loved it. Beautiful home. Fully equipped, everything seemed new and updated. Small pool but really nice set up with great outdoor furniture, grill. The beds...

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$338
avg per night
Anna Maria Island House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Salt Air East by Beach Retreats Vacation Rentals 7106 Marina Ave Holmes Beach, FL 34217 ​​​​​​​VRC19-000278 2 Bedrooms | 2 Bathrooms | Sleeps 6 | Heated Pool Pet friendly This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighborsBook with confidence:...

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$314
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Hammock Hideaway! .02 Miles to Pine Ave. Shopping, Restaurants, and more! .03 Miles to AMI Beaches 8 Hole Mini Golf Course Private Heated Pool, Jacuzzi, BBQ Grill, Sun Loungers Beach chairs, wagon, and a cooler available Family friendly with pack'n'play and highchair High-speed...

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$695
avg per night

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

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Have you been dreaming about the water here on Floridas Beautiful Gulf Coast? Well, come enjoy "Bay Dreamin" Walk To Bayfront Park located directly across the street! .03 Miles to Pine Ave. Fishing, Shopping, Restaurants, and more! Private Heated Pool/Spa, Putt-Putt Golf Fully Renovated...

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$752
avg per night
Anna Maria Island House
Sleeps 17, 7 bedrooms, 7.5 bathrooms

Key Amenities

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

About this property

Welcome to Ocean Star! .01 Miles to Amazing Gulf Coast Beaches Private Heated Pool/Spa with Outdoor Seating & BBQ Beach Equipment Available for Use Every Bedroom Has a Private Bathroom Fully stocked kitchen for all of your favorite home-cooked meals High-speed Wi-Fi, Smart lock for Self Check-in...

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$561
avg per night
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