49 Rentals: Anna Maria Island & Holmes BeachPlatinum

All Pool Options

Get help finding your rental: 941.900.4552

Three Bedroom Luxury Condo - Upscale Interior - View of Gulf

  Save Rental
  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Anna Maria Island Vacation Luxury home Ocean Front Property

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Luxury Anna Maria Island Three Bedroom Home Private Pool

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Bay View Luxury Three bedroom Vacation Rental Plus Den

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Luxury Villa Anna Maria Island 100 Steps to the Beach

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 Bathrooms

Luxury 4 Bedroom - 2 Living Areas - Pool - North Anna Maria

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Anna Maria Vacation Home 7 Bedrooms 2 Kitchens! Top Rentals

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 7 Bedrooms
  • 5 Bathrooms

Canal front beauty on Anna Maria Rental with Pool

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 4 Bedrooms
  • 3 Bathrooms

Five Bedroom Rental on the North End of Anna Maria Island

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 11
  • 5 Bedrooms
  • 4 Bathrooms

Almost Beachfront - Luxury Anna Maria Island Vacation Home

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 7 Bedrooms
  • 5 Bathrooms

Anna Maria Island 4 Bedroom Luxury Vacation Rental Sleeps 8

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Anna Maria Luxury Four Bedroom Rental with Gulf Views

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 Bathrooms

Luxury Anna Maria 9 Bedroom Beach Vacation Rental with Pool

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 23
  • 9 Bedrooms
  • 6 Bathrooms

Stunning 3 Bedroom Anna Maria Villa Rental with Private Pool

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Luxury Anna Maria Eight Bedroom Beach Rental Home with Pool

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 8 Bedrooms
  • 6 Bathrooms

Anna Maria Island Luxury Home with Pool Two Blocks to Beach

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Three Bedroom Luxury Vacation Rental Anna Maria Island

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

One of the Best Beach Vacation Rentals On Anna Maria Island.

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Luxury Five Bedroom Luxury Anna Maria Island Rental Home

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 4 Bathrooms

One of the Best Anna Maria Island Vacation Rental Homes

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 5 Bathrooms

Anna Maria Steps from Beach at this 4 Bedroom Vacation Home

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 Bathrooms

Anna Maria Island Beachfront Home - Nine Bedroom Sleeps 28

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 28
  • 9 Bedrooms
  • 9 Bathrooms

Rent Anna Maria Beachfront 7 Bedroom Vacation Pool Home

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 7 Bedrooms
  • 6 Bathrooms

Luxury Anna Maria 7 Bedroom Rental Private Beach

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 7 Bedrooms
  • 7 Bathrooms

Stunning 10 Bedroom Estate on the Beach with Private Pool

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 20
  • 10 Bedrooms
  • 7 Bathrooms

Anna Maria 4 Bedroom 4 Bathroom Vacation Home Sleeps 12

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 Bathrooms

Luxury Four Bedroom Home on the Beach

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 Bathrooms

A Stunning an Anna Maria Island Vacation Home Sleeps 8

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

One of the Most Stunning Rentals on Anna Maria Island 5 Star

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Luxury Five Bedroom Anna Maria Vacation Home Sleeps 12

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 4 Bathrooms

Stunning 4 Bedroom Canal Front Home with Private Pool

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Luxury Anna Maria Six Bedroom Bayfront Vacation Rental Home

  Save Rental
  • Platinum
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 18
  • 6 Bedrooms
  • 5 Bathrooms

Luxury Anna Maria Vacation Home Short Walk to Beach Sleep 14

  Save Rental
  • Platinum
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 14
  • 5 Bedrooms
  • 5 Bathrooms

Anna Maria Luxury Five Bedroom Vacation Home Sleeps Twelve

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 4 Bathrooms

Four Bedroom Island Home Steps from Sugar White Sandy Beach

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Anna Maria 4 Bedroom Vacation Home Canal View and Pool

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 2 Bathrooms

Large & Luxurious Anna Maria Island 7 Bedroom Rental

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 17
  • 7 Bedrooms
  • 7 Bathrooms

Luxury Bradenton Beaches Top Rental Home Luxury All the Way!

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 23
  • 10 Bedrooms
  • 8 Bathrooms

Luxury Anna Maria Island Vacation Home with Private Pool

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Holmes Beach Anna Maria Island Luxury Pool Vacation Home

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 Bathrooms

Wow Luxury Anna Maria Beachfront Vacation Home Sleeps 18

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 8 Bedrooms
  • 6 Bathrooms

Anna Maria Vacation Home Rental Sleeps 12 Guests

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 6 Bathrooms

The Most Beautiful Beach Home on Anna Maria Island

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Anna Maria Island Home Sleeps Twelve Guests

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 6 Bathrooms

Anna Maria Island Vacation Home Sleeps 14 Spectacular Rental

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 6 Bedrooms
  • 6 Bathrooms

Bradenton Beach 7 Bedroom Vacation Home Sleeps 18

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 7 Bedrooms
  • 7 Bathrooms

The ultimate Anna Maria Vacation Residence

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Luxury Anna Maria Island Vacation Home

  Save Rental
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • Bathrooms

Anna Maria Island Vacation Home Sleeps 8 Guests

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms