Newest Rentals

Newest Rentals

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Newest Rentals

Mere steps away from the postcard perfect beaches, and legendary sunsets Anna Maria Island is famous …Read More

Rest Assured
  • Bedrooms: 3
  • Bath (f/h): 2/1
  • Sleeps: 6
  • Type: Near The Beach
  • Price: $393 – $1,400

Save 25% when you book now and stay 7 nights before May 31st 2019 …Read More

Coral Reef
  • Bedrooms: 4
  • Bath (f/h): 3/1
  • Sleeps: 8
  • Type: Pool Homes
  • Price: $400 – $839

Nestled along a canal on Anna Maria Island’s exclusive Key Royale, you’ll find Peaceful Palms. Sophisticated tropical luxury living awaits…Read More

Peaceful Palms
  • Bedrooms: 3
  • Bath (f/h): 2/5
  • Sleeps: 6
  • Type: Canal Homes
  • Price: $00 – $00

Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018!…Read More

AMI Boathouse
  • Bedrooms: 3
  • Bathrooms: 2
  • Sleeps: 8
  • Canal Homes
  • Price: $429 – $571

Still undergoing a gorgeous renovation, but will be available for arrivals by Oct. Read More

5 O’Clock Somewhere
  • Bedrooms: 4
  • Bathrooms: 2
  • Sleeps: 8
  • Near The Beach
  • Price: $2,800 – $4,200

Tucked behind an unassuming door in one of Anna Maria Island’s best resort style condo communities… Read More

Playa Paradise
  • Bedrooms: 2
  • Bath: (full/half): 2/1
  • Sleeps: 4
  • On The Beach
  • Price: $1,000 – $1,500

Relax in lush tropical island style in this Anna Maria Island condo! Read More

Island Serenity
  • Bedrooms: 3
  • Bathrooms: Bath (full/half): 2/5
  • Sleeps: 8
  • Type: Near The Beach
  • Price: $850 – $2200

Located in Holmes Beach, this vacation rental is centrally positioned  Read More

North Beach 55
  • Bedrooms: 3
  • Bathrooms: Bath (full/half): 2/1
  • Sleeps: 6
  • Type: Near The Beach
  • Price: $1005 – $1550

Welcome to the Seaside Inn, located on charming Anna Maria  Read More

Seaside Inn
  • Bedrooms: 3
  • Bathrooms: 3
  • Sleeps: 6
  • Type: Near The Beach
  • Price: $4200 – $6050

This elevated vacation rental offers all the modern conveniences  Read More

Sandy Feet Retreat
  • Bedrooms: 2
  • Bathrooms: 2
  • Sleeps: 4
  • Type:Pool Homes
  • Price: $1250 – $1750

Great 3 bedroom/2 bathroom completely updated property  Read More

Crab Shack
  • Bedrooms: 3
  • Bathrooms: 2
  • Sleeps: 6
  • Type:  Near The Beach
  • Price: $2250 – $2500

Gulf Dream is a large and luxurious coastal home, just a few minutes…  Read More

A Gulf Dream
  • Bedrooms: 3
  • Bath (full/half): 2/1
  • Sleeps: 6
  • Type:  Near The Beach
  • Price: $850 – $2,200

Just two blocks from the most pristine beaches of the north end of Anna Maria Island, you’ll find Dreamscape!…Read More

Dreamscape
  • Bedrooms: 2
  • Bathrooms: 2
  • Sleeps: 4
  • Near The Beach
  • Price: $1,400 – $1,900