81 Vacation Rentals Found: Platinum Anna Maria Island & Holmes Beach

All Pool Options

Get help finding your rental: (866) 922.0572

Holmes Beach Luxury Condo Rental Communal Pool & Gulf Views

  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Beachfront Luxury Three Bedroom Vacation Rental with Pool.

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

Three Bedroom Luxury Condo - Upscale Interior - View of Gulf

  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Vacation Rental on Anna Maria island with Pool and Boat Dock

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

Luxury Island Rental Home- Six Bedrooms Mediterranean Style

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 3 Bathrooms

Posh Anna Maria Vacation Condos on the Beach - 3 Bedrooms

  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Eight Bedroom - Sleep 16 North Holmes Beach One Min to Beach

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 8 Bedrooms
  • 5 Bathrooms

Anna Maria Gulf View Luxury Three Bedroom Beachfront Condo

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

Gulf Front on Beach Vacation Rental - Three Bedrooms

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

A Real Beach House on Anna Maria Island with Pool

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

No Roads to Cross Sleeps 10! Pool/Hot Tub Anna Maria Rental

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

Anna Maria Five Bedroom Rental - Rarely Look This Great!

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 5 Bedrooms
  • 4 Bathrooms

Anna Maria - Most Beautiful Vacation Stroll to the Beach

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

North End Anna Maria Vacation Rental with Pool Sleeps 8

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

Luxury Beach Condo with Two Bedrooms

  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Six Bedroom Luxury Vacation Rental Home - Sleeps 12

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

Posh Vacation Rental Home with Four Bedrooms and Private Pool

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

Six Bedroom 5 Bathroom Vacation Rentals - Available Weekly

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

Beautiful Beach Pool Home on Anna Maria Island. Sleeps 16

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

Largest Anna Maria Beach House Estate Sleeps 21

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 21
  • 9 Bedrooms
  • 6 Bathrooms

Direct Bay Front Luxury Vacation Rental with Boat Dock

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

Bay View Luxury Three bedroom Vacation Rental Plus Den

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

Three Bedroom Vacation Condo for Rent with Full Gulf View

  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Luxury Anna Maria Island Beach House Rental with Pool

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

Anna Maria Island Luxury Beach Vacation Rental Sleeps 12

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

Luxury Anna Maria Island Rental

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

Anna Maria Island Luxury 5 Bedroom Vacation Rental with Pool

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

Six Bedroom Family Vacation Rental, Sleeps 16 Guests

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

Luxury Anna Maria Estate in Cortez Main and Guest Home

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 6 Bedrooms
  • 5 Bathrooms

Fabulous Anna Maria Island Luxury Home Sleeps 16- Eight Bdrm

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

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

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

Anna Maria Island 4 Bedroom Vacation Rental Sleeps 12 Guests

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

Anna Maria Vacation Home 7 Bedrooms 2 Kitchens!

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

Anna Maria Island Home for Rent on Beach

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

Canal front beauty on Anna Maria Rental with pool

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

Beachfront private pool Anna Maria Rental sleeps 18

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

8 bedroom deluxe pool sleep 16 rental on Anna Maria

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

4 Bedroom Plus Den Private Pool and 3 Houses to Beach on AMI

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

Anna Maria Island Five Bedroom Vacation Rental Pool & Spa

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

Anna Maria Island Luxury Beach Front Pool Vacation Rental

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

Almost Beachfront Luxury Anna Maria Island Vacation Home

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 18
  • 7 Bedrooms
  • 5 Bathrooms

Anna Maria Island 4 Bedroom Luxury Vacation Rental Sleeps 8

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

Gulf Views from Holmes Beach 5 Bed Pool Rental on Anna Maria

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

Anna Maria 9 Bedroom Beach Vacation Rental with Pool

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

Five Bedroom Villa Luxury Interior & Large Private Pool

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Stunning 3 Bedroom Anna Maria Villa Rental with Private Pool

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

Six Bedroom Luxury Vacation Rental on Anna Maria Sleeps 14

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 6 Bedrooms
  • 3 Bathrooms

Luxury Anna Maria Eight Bedroom Beach Rental Home with Pool

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

One of Anna Maria Islands Most Luxurious Vacation Rental

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 15
  • 6 Bedrooms
  • 4 Bathrooms

Four Bedroom Anna Maria Vacation Rental- 3.5 Bathooms

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

Luxury 7 bedroom sleep 21 on Anna Maria Island

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 21
  • 7 Bedrooms
  • 7 Bathrooms

Anna Maria Island Luxury Home with Pool

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

Luxury Homes Beach 4 Bedroom Rental Walk to Beach with Pools

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

Luxury Anna Maria Island Five Bedroom Beach Home Sleeps 10

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

A Posh Three Bedroom Pool rental Home Bradenton Golf View

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

Anna Maria Island 5 Bedroom Luxury Vacation Home- Gulf Views

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

Three Bedroom Luxury Vacation Rental Anna Maria Island

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

Anna Maria Island 5 Bedroom Luxury Beachfront Vacation Home

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

One of the Best Vacation Rentals On Anna Maria Island.

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

Anna Maria Island Four Bedroom Luxury Pool Vacation Rental

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

6 Bedroom with Private Pool Rental on Anna Maria Island

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

Luxury Five Bedroom Luxury Anna Maria Island Vacation Home

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

One of the Best Anna Maria Island Vacation Rental Homes

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

Luxury Vacation Rental - Sleeps Maximum of 30 Guests

  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 30
  • 11 Bedrooms
  • 8 Bathrooms

Bayfront Luxury Anna Maria Island Vacation Home Top Rental!

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

Steps from the Beach at this Four Bedroom Vacation Home

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

Beachfront Nine Bedroom Sleeps 28 Anna Maria Rental W/Pool

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

Rent Beachfront 7 Bedroom 6 Bathroom Vacation House Pool

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

Beachfront Beauty 4 bedroom with pool Anna Maria rental

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

Four Bedroom Vacation Home Sleeps 8 Guests with Canal View

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

Luxury Four Bedroom Home on the Beach

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

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

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

Nine Bedroom Vacation Home Sleeps 22 Anna Maria island

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 22
  • 9 Bedrooms
  • 6 Bathrooms

Luxury Five Bedroom Vacation Home Sleeps 12 Guests

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

Luxury Anna Maria Vacation Rental Home with Five Bedrooms

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

Anna Maria Luxury Five Bedroom Vacation Home Sleeps Eight

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

Four Bedroom Vacation Home Canal View and Private Pool

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

Beautiful Cottage Luxury Will Sleep Eight

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 7
  • 3 Bedrooms
  • 2 Bathrooms

Luxury Anna Maria North End Beach Cottage with Private Pool

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

The Ultimate Anna Maria Luxury Vacation Home Stunning!

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

Bradenton Beaches Top Rental Home Luxury All the Way

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 26
  • 10 Bedrooms
  • 9 Bathrooms