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Stay for a Cause

Book any new vacation now through 11/22/24 and a portion of the reservation will be donated to the Center of Anna Maria, helping fund recovery and rebuilding across the island! 

Anna Maria Island Rentals With Pool

Make a splash on your next vacation!  Discover AMI Locals luxury Anna Maria Island rental properties with pools.  There's nothing better after a long day of fun in the sun at the beach than dipping your toes into a nice private backyard pool.  Many of our Anna Maria Island vacation rental properties feature private pools, spas, waterslides, beachfront pools, shared resort pools, you name it!  Soak up island time and Florida sunshine in style, book a luxury home with a must-have swimming pool!

Let our Reservation specialists help find your perfect Anna Maria Island rental with a pool today.  Call or email us with any questions!

  • 297 properties returned
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Here Comes The Sun

Condo
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6

Endless Summer

House
  • 5 Bedrooms
  • 6 Full, 1 Half Bathrooms
  • Sleeps 14
Exclusive Collection

Coming In Hot

House
  • 4 Bedrooms
  • 4 Full, 1 Half Bathrooms
  • Sleeps 8

Bay Breezes at Bayside Bungalow

Villa
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6

Rising Tide

House
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 10

Coconuts Gulf View #118

Condo
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Majestic Summer

House
  • 7 Bedrooms
  • 7 Full, 1 Half Bathrooms
  • Sleeps 14

Avalon

House
  • 4 Bedrooms
  • 3 Full, 1 Half Bathrooms
  • Sleeps 8

Sea Horse Beach House

House
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10

Garden Party

House
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6

Lay'By, Too

House
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Villa #6 Starfish

Villa
  • 1 Bedroom
  • 1 Bathrooms
  • Sleeps 4
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