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

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

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

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

Just one house away from Sarasota bay and a two-minute walk to the picture perfect…Read More

Sideways
  • Bedrooms: 2
  • Bathrooms: 2
  • Sleeps: 6
  • Pool Homes
  • Price: $179 – $1,800

Tucked away in a quiet neighborhood on the northern end of Holmes!…Read More

Seahorse Ranch
  • Bedrooms: 2
  • Bathrooms: 2
  • Sleeps: 4
  • Near The Beach
  • Price: $3,750 – $5,357

Book Now & Automatically Save 25% OFF Your Stay The Week Of July 4th!…Read More

Ocean Blue Retrea
  • Bedrooms: 4
  • Bathrooms: (full/half): 3/1
  • Sleeps: 8
  • Pool Homes
  • Price: $339– $4,000

With gorgeous decor and sleek retro modern style, with an Island twist, this…Read More

Fantasea
  • Bedrooms: 3
  • Bathrooms: 2
  • Sleeps: 4
  • Near The Beach
  • Price: $4,286– $7,500

This canal front home boasts 5 bedrooms and 5 bathrooms on two private levels; …Read More

Bayside Inn
  • Bedrooms: 5
  • Bathrooms: 5
  • Sleeps: 8
  • Canal Homes
  • Price: $4,500– $8,000

Book Now & Automatically Save 25% OFF Your Stay Now Through July 31st…Read More

100 Steps To The Beach
  • Bedrooms: 5
  • Bathrooms: 3
  • Sleeps: 8
  • Pool Homes
  • Price: $4,29– $4,200

Automatically Save 25% OFF when you stay between June 1st & June 28th! …Read More

Island Dream
  • Bedrooms: 3
  • Bathrooms: 2
  • Sleeps: 6
  • Pool Homes
  • Price: $321– $2,800