0 941.500.4555 Request a Call

Anna Maria Island & Holmes Beach Vacation Rentals with Private Pools

Browse professionally managed Anna Maria Island and Holmes Beach vacation rentals with a recorded fenced, unfenced or indoor private pool. Showing 745–768 of 1,169 matching vacation rentals, page 32 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
Filters Private pool — remove this filter Clear all
Gold Holmes Beach Luxury Vacation Home 3 Bedrooms & Private Pool
Anna Maria Island & Holmes Beach

Holmes Beach Luxury Vacation Home 3 Bedrooms & Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $564 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Vacation Home 2 houses from Beach Access
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Home 2 houses from Beach Access

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,531 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria 6 bedroom Rental 1 Min to the Beach!
Anna Maria Island & Holmes Beach

Anna Maria 6 bedroom Rental 1 Min to the Beach!

6 Bedrooms · 4 Bathrooms · Sleeps 12
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Vacation Rental with Private Heated Pool - Holmes Beach Coastal Retreat
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Rental with Private Heated Pool - Holmes Beach Coastal Retreat

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,085 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Renovated Anna Maria Historical Cottage- New Private Pool
Anna Maria Island & Holmes Beach

Renovated Anna Maria Historical Cottage- New Private Pool

3 Bedrooms · 3 Bathrooms · Sleeps 7
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Vacation Pool Home Short Walk to Beach
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Pool Home Short Walk to Beach

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,102 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Three Bedroom Rental Anna Maria Island with Pool
Anna Maria Island & Holmes Beach

Luxury Three Bedroom Rental Anna Maria Island with Pool

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,138 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Anna Maria Island 7 Bedroom Vacation Rental Sleeps 18
Anna Maria Island & Holmes Beach

Luxury Anna Maria Island 7 Bedroom Vacation Rental Sleeps 18

7 Bedrooms · 7 Bathrooms · Sleeps 19
From $2,150 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Luxury Vacation Home One Minute Walk to Beach
Anna Maria Island & Holmes Beach

Anna Maria Luxury Vacation Home One Minute Walk to Beach

7 Bedrooms · 6 Bathrooms · Sleeps 16
From $2,110 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Rental 6 Bedroom Rental Walk to Beach
Anna Maria Island & Holmes Beach

Holmes Beach Rental 6 Bedroom Rental Walk to Beach

6 Bedrooms · 5 Bathrooms · Sleeps 12
From $1,689 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Stunning Three Bedroom Vacation Rental on Holmes Beach
Anna Maria Island & Holmes Beach

Stunning Three Bedroom Vacation Rental on Holmes Beach

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,295 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Magnificent Gulf Views New Interior Excellent Pool/Lounger Area
Anna Maria Island & Holmes Beach

Magnificent Gulf Views New Interior Excellent Pool/Lounger Area

6 Bedrooms · 4 Bathrooms · Sleeps 14
From $2,286 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton 3 Bedroom Vacation Rental Sleeps 8 Private Pool
Anna Maria Island & Holmes Beach

Bradenton 3 Bedroom Vacation Rental Sleeps 8 Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $895 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold A stunning Beach House on Anna Maria with Private Pool
Anna Maria Island & Holmes Beach

A stunning Beach House on Anna Maria with Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold 3/2 Bedroom Vacation Cottage with Pool Anna Maria Island
Anna Maria Island & Holmes Beach

3/2 Bedroom Vacation Cottage with Pool Anna Maria Island

3 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Private Pool 2 Bedroom 2 Bathroom Anna Maria Vacation Home
Anna Maria Island & Holmes Beach

Private Pool 2 Bedroom 2 Bathroom Anna Maria Vacation Home

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,095 / week
Call to confirm availability941.500.4555 Request a callback & quote
Gold Three Bedroom Home With Private Pool In Anna Maria
Anna Maria Island & Holmes Beach

Three Bedroom Home With Private Pool In Anna Maria

3 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Ground Level Pool Home Bradenton Best Rental
Anna Maria Island & Holmes Beach

Ground Level Pool Home Bradenton Best Rental

2 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Rental Home with Four Bedrooms
Anna Maria Island & Holmes Beach

Anna Maria Vacation Rental Home with Four Bedrooms

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,771 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Home with Private Pool Walk To Beach
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Home with Private Pool Walk To Beach

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $795 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lovely Sleeps 10 Family Home Private Pool 1 Block to Beach!!
Anna Maria Island & Holmes Beach

Lovely Sleeps 10 Family Home Private Pool 1 Block to Beach!!

3 Bedrooms · 2 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Vacation Pool Home 3 Bedrooms One Block to Beach
Anna Maria Island & Holmes Beach

Luxury Vacation Pool Home 3 Bedrooms One Block to Beach

3 Bedrooms · 3 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Two Bedroom Holmes Beach Vacation Cottage with Pool
Anna Maria Island & Holmes Beach

Two Bedroom Holmes Beach Vacation Cottage with Pool

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $615 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Walk to Beach Vacation Rentals Three Bedroom in Holmes Beach
Anna Maria Island & Holmes Beach

Walk to Beach Vacation Rentals Three Bedroom in Holmes Beach

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,326 / night
Call to confirm availability941.500.4555 Request a callback & quote

Privacy controls

Choose which cookies we use

Optional cookies are off unless you choose otherwise. You can return to these settings from the footer at any time.

Essential & requested features Required for security and for features you ask us to provide, including saved rentals and remembered search choices. Always active

Cookie PolicyPrivacy Policy

Talk with a Villa Specialist

When should we call you?

Share a few details and an Emerald Kite specialist will call you now or in five minutes.

If you provide a mobile number, you consent to receive messages about your vacation planning. Carrier rates may apply; you can opt out at any time.

Security check loads when this window opens.

Requests after 10 p.m. Eastern Time will be returned the next day.

Having trouble? Use the full Contact page.