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 505–528 of 1,169 matching vacation rentals, page 22 of 49. Closest capacity matches first.

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

Anna Maria Island Vacation Home

6 Bedrooms · 4 Bathrooms · Sleeps 18
From $1,992 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Luxury Vacation Rental Home Eight Guests
Anna Maria Island & Holmes Beach

Anna Maria Island Luxury Vacation Rental Home Eight Guests

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,453 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Walk to Beach Five Bedroom Vacation Home
Anna Maria Island & Holmes Beach

Anna Maria Walk to Beach Five Bedroom Vacation Home

5 Bedrooms · 6 Bathrooms · Sleeps 14
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Bradenton Beach Home: Pool, Spa, & Bay Views
Anna Maria Island & Holmes Beach

Luxury Bradenton Beach Home: Pool, Spa, & Bay Views

8 Bedrooms · 8 Bathrooms · Sleeps 18
From $1,900 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Luxury Vacation Rental Home Sleeps Six Guests
Anna Maria Island & Holmes Beach

Holmes Beach Luxury Vacation Rental Home Sleeps Six Guests

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $703 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Luxury Vacation Rental Home Four Bedrooms
Anna Maria Island & Holmes Beach

Anna Maria Island Luxury Vacation Rental Home Four Bedrooms

4 Bedrooms · 3 Bathrooms · Sleeps 12
From $770 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Four Bedroom Vacation Pool Home Sleeps 8
Anna Maria Island & Holmes Beach

Holmes Beach Four Bedroom Vacation Pool Home Sleeps 8

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $860 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Three Bedroom Pool Home
Anna Maria Island & Holmes Beach

Holmes Beach Three Bedroom Pool Home

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

Three Bedroom Pool Home in Holmes Beach Walk to Beach

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $885 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Luxury Vacation Pool Home Near Beach & Fun
Anna Maria Island & Holmes Beach

Holmes Beach Luxury Vacation Pool Home Near Beach & Fun

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,293 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Short Walk to Beach Pool Home in Holmes Beach Vacation
Anna Maria Island & Holmes Beach

Short Walk to Beach Pool Home in Holmes Beach Vacation

3 Bedrooms · 2 Bathrooms · Sleeps 10
From $1,438 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold 3 Bedroom Holmes Beach Vacation Home with Private Pool
Anna Maria Island & Holmes Beach

3 Bedroom Holmes Beach Vacation Home with Private Pool

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,230 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Anna Maria Vacation Home Sleeps Six Guests
Anna Maria Island & Holmes Beach

Luxury Anna Maria Vacation Home Sleeps Six Guests

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,195 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Rental Sleeps Six Guests Walk to Beach
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Rental Sleeps Six Guests Walk to Beach

3 Bedrooms · 3 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Rental Sleeps Ten Guests
Anna Maria Island & Holmes Beach

Anna Maria Vacation Rental Sleeps Ten Guests

3 Bedrooms · 3 Bathrooms · Sleeps 10
From $833 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Luxury Vacation Rental with a Pool
Anna Maria Island & Holmes Beach

Anna Maria Island Luxury Vacation Rental with a Pool

3 Bedrooms · 2 Bathrooms · Sleeps 7
From $1,195 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Vacation Home Sleeps Six Guests
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Home Sleeps Six Guests

3 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Luxury 4 Bedroom Vacation Home with Pool
Anna Maria Island & Holmes Beach

Holmes Beach Luxury 4 Bedroom Vacation Home with Pool

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,104 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Stunning Outdoor Oasis Area. Anna Maria Vacation Home
Anna Maria Island & Holmes Beach

Stunning Outdoor Oasis Area. Anna Maria Vacation Home

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,868 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Rental Sleeps Four Guests
Anna Maria Island & Holmes Beach

Anna Maria Vacation Rental Sleeps Four Guests

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $895 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Accommodation Walk to Beach
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Accommodation Walk to Beach

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $402 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Luxury Vacation Home Sleeps 8 Private Pool
Anna Maria Island & Holmes Beach

Anna Maria Luxury Vacation Home Sleeps 8 Private Pool

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,401 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Home Sleeps Six Guests
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Home Sleeps Six Guests

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $895 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Rental Pool Home Sleeps Six Guests
Anna Maria Island & Holmes Beach

Anna Maria Vacation Rental Pool Home Sleeps Six Guests

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,636 / 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.