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 481–504 of 1,169 matching vacation rentals, page 21 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
Filters Private pool — remove this filter Clear all
Gold Anna Maria Island Beach House Four bedrooms with Pool
Anna Maria Island & Holmes Beach

Anna Maria Island Beach House Four bedrooms with Pool

4 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury 5 Bedroom Anna Maria Vacation Pool Home
Anna Maria Island & Holmes Beach

Luxury 5 Bedroom Anna Maria Vacation Pool Home

5 Bedrooms · 3 Bathrooms · Sleeps 8
From $2,684 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beachfront Holmes Beach Vacation Home Sleeps 12 Guests
Anna Maria Island & Holmes Beach

Beachfront Holmes Beach Vacation Home Sleeps 12 Guests

6 Bedrooms · 4 Bathrooms · Sleeps 12
From $2,394 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Ground Floor Vacation Rental Home Sleeps 8
Anna Maria Island & Holmes Beach

Bradenton Ground Floor Vacation Rental Home Sleeps 8

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $695 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold ANNA MARIA 1 BLOCK TO BEACH
Anna Maria Island & Holmes Beach

ANNA MARIA 1 BLOCK TO BEACH

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $711 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Luxury Vacation Rental Home Sleeps Six Guests
Anna Maria Island & Holmes Beach

Anna Maria Luxury Vacation Rental Home Sleeps Six Guests

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

Three Bedroom Holmes Beach Vacation Home Sleeps 6 Guests

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,102 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Rental Anna Maria Island Luxury Home with Pool & Rooftop Deck
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Rental Anna Maria Island Luxury Home with Pool & Rooftop Deck

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,031 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beautiful Three Bedroom Vacation Pool Home in Anna Maria
Anna Maria Island & Holmes Beach

Beautiful Three Bedroom Vacation Pool Home in Anna Maria

3 Bedrooms · 3 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Beach Vacation Pool Home With Bay Views Sleeps 10
Anna Maria Island & Holmes Beach

Bradenton Beach Vacation Pool Home With Bay Views Sleeps 10

3 Bedrooms · 2 Bathrooms · Sleeps 10
From $1,195 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Three Bedroom Walk to Beach Vacation Home
Anna Maria Island & Holmes Beach

Anna Maria Three Bedroom Walk to Beach Vacation Home

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,181 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Stunning Holmes Beach Vacation Pool Home Sleeps 8 Guests
Anna Maria Island & Holmes Beach

Stunning Holmes Beach Vacation Pool Home Sleeps 8 Guests

4 Bedrooms · 4 Bathrooms
From $19,845 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Magnificent Holmes Beach Three Bedroom Pool Home
Anna Maria Island & Holmes Beach

Magnificent Holmes Beach Three Bedroom Pool Home

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $524 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Stunning 4 Bedroom Home on the Canal with Pool and Dock
Anna Maria Island & Holmes Beach

Stunning 4 Bedroom Home on the Canal with Pool and Dock

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,151 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria 3 Bedroom Cottage with Private Pool
Anna Maria Island & Holmes Beach

Anna Maria 3 Bedroom Cottage with Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $895 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beautiful Anna Maria Vacation Home with Private Beach Access
Anna Maria Island & Holmes Beach

Beautiful Anna Maria Vacation Home with Private Beach Access

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $1,947 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Beach Three Bedroom Vacation Pool Home
Anna Maria Island & Holmes Beach

Bradenton Beach Three Bedroom Vacation Pool Home

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $645 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Breathtaking Bradenton Beach Luxury Pool Home Walk To Beach
Anna Maria Island & Holmes Beach

Breathtaking Bradenton Beach Luxury Pool Home Walk To Beach

7 Bedrooms · 7 Bathrooms · Sleeps 14
From $1,950 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold 3 Bedroom Vacation Home in Holmes Beach with Private Pool
Anna Maria Island & Holmes Beach

3 Bedroom Vacation Home in Holmes Beach with Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $658 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Walk to Beach 2 Bedrooms Plus Loft Home Sleeps 8
Anna Maria Island & Holmes Beach

Anna Maria Walk to Beach 2 Bedrooms Plus Loft Home Sleeps 8

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

Anna Maria Island Vacation Home 3 Bedroom Sleeps Six Guests

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

Anna Maria Island Vacation Rental Sleeps Six Guests

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $911 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Rental Canal Front Beach House with Pool
Anna Maria Island & Holmes Beach

Anna Maria Vacation Rental Canal Front Beach House with Pool

3 Bedrooms · 3 Bathrooms · Sleeps 7
From $1,236 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Beach Luxury Vacation Rental Home Two Bedrooms
Anna Maria Island & Holmes Beach

Bradenton Beach Luxury Vacation Rental Home Two Bedrooms

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $795 / 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.