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 529–552 of 1,169 matching vacation rentals, page 23 of 49. Closest capacity matches first.

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

Holmes Beach Vacation Rental Pool Home Five Bedrooms

5 Bedrooms · 4 Bathrooms · Sleeps 10
From $1,539 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Home Sleeps Six Guests
Anna Maria Island & Holmes Beach

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 Charming Home on Holmes Beach with Pool -Short Walk to Beach
Anna Maria Island & Holmes Beach

Charming Home on Holmes Beach with Pool -Short Walk to Beach

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,093 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Magnificent Pool Home One of The Best
Anna Maria Island & Holmes Beach

Holmes Beach Magnificent Pool Home One of The Best

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,093 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Gulf Views From This Anna Maria Luxury 4 Bedroom Rental
Anna Maria Island & Holmes Beach

Gulf Views From This Anna Maria Luxury 4 Bedroom Rental

4 Bedrooms · 4 Bathrooms · Sleeps 10
From $1,443 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Vacation Home Sleeps 8 Guests With Private Pool
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Home Sleeps 8 Guests With Private Pool

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

Lakewood Vacation Pool Home Sleeps Six Guests

3 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold The Ultimate Anna Maria Island 4 Bedroom Home Steps to Sand
Anna Maria Island & Holmes Beach

The Ultimate Anna Maria Island 4 Bedroom Home Steps to Sand

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,140 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Gorgeous Island Vacation Home with Private Pool Sleeps 8
Anna Maria Island & Holmes Beach

Gorgeous Island Vacation Home with Private Pool Sleeps 8

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $850 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Rental Home Three Bedrooms Sleeps 6
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Rental Home Three Bedrooms Sleeps 6

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 Home Sleeps Eight Guests
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Rental Home Sleeps Eight Guests

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,079 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Anna Maria Island Vacation Rental - Florida Gulf Coast Bayfront Home
Anna Maria Island & Holmes Beach

Luxury Anna Maria Island Vacation Rental - Florida Gulf Coast Bayfront Home

5 Bedrooms · 5 Bathrooms · Sleeps 12
From $1,822 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Pet Friendly Anna Maria Vacation Pool Home Sleeps 8 Guests, two blocks from the beach!
Anna Maria Island & Holmes Beach

Pet Friendly Anna Maria Vacation Pool Home Sleeps 8 Guests, two blocks from the beach!

4 Bedrooms · 3 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming Duplex for Rent on Holmes Beach Sleeps Six Guests
Anna Maria Island & Holmes Beach

Charming Duplex for Rent on Holmes Beach Sleeps Six Guests

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $686 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Exclusive Vacation rental Anna Maria Island
Anna Maria Island & Holmes Beach

Exclusive Vacation rental Anna Maria Island

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,270 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beachside Retreat 4-Bedroom Home Rental - Your Perfect Island Getaway
Anna Maria Island & Holmes Beach

Beachside Retreat 4-Bedroom Home Rental - Your Perfect Island Getaway

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,400 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island 5 Bedroom Luxury Pool Vacation Home
Anna Maria Island & Holmes Beach

Anna Maria Island 5 Bedroom Luxury Pool Vacation Home

5 Bedrooms · 5 Bathrooms · Sleeps 8
From $2,610 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Fabulous Four Bedroom Home Sleeps 10
Anna Maria Island & Holmes Beach

Holmes Beach Fabulous Four Bedroom Home Sleeps 10

4 Bedrooms · 3 Bathrooms · Sleeps 10
From $1,691 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Rental Pool Home Steps to Beach
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Rental Pool Home Steps to Beach

4 Bedrooms · 6 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold One Min Walk to Beach homes Beach Five Bedroom Homes Beach
Anna Maria Island & Holmes Beach

One Min Walk to Beach homes Beach Five Bedroom Homes Beach

5 Bedrooms · 7 Bathrooms · Sleeps 12
From $610 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Palmetto Vacation Home Three Bedroom Water Views
Anna Maria Island & Holmes Beach

Palmetto Vacation Home Three Bedroom Water Views

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $720 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Rental Sleeps Six Guests
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Rental Sleeps Six Guests

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $795 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Vacation Rental Sleeps Five Guests
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Rental Sleeps Five Guests

2 Bedrooms · 2 Bathrooms · Sleeps 5
From $795 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Pool Home 3 Bedroom Sleeps Six Guests
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Pool Home 3 Bedroom Sleeps Six Guests

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,342 / 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.