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 1,033–1,056 of 1,169 matching vacation rentals, page 44 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
Filters Private pool — remove this filter Clear all
Silver Charming Vacation Rental on Anna Maria Island. Call Today
Anna Maria Island & Holmes Beach

Charming Vacation Rental on Anna Maria Island. Call Today

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $296 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Bradenton Beach Vacation Home Sleeps Six Guests
Anna Maria Island & Holmes Beach

Bradenton Beach Vacation Home Sleeps Six Guests

3 Bedrooms · 1 Bathroom · Sleeps 6
From $233 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Bradenton Vacation Rental Home Three Bedrooms Sleeps 6
Anna Maria Island & Holmes Beach

Bradenton Vacation Rental Home Three Bedrooms Sleeps 6

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $522 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Canal Front Vacation Home 3 Bedrooms With Pool & Hot Tub
Anna Maria Island & Holmes Beach

Canal Front Vacation Home 3 Bedrooms With Pool & Hot Tub

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $480 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Anna Maria Vacation Rentals Sleeps Four Guests
Anna Maria Island & Holmes Beach

Anna Maria Vacation Rentals Sleeps Four Guests

2 Bedrooms · 2 Bathrooms · Sleeps 4
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Silver Luxury 4 Bedroom Plus 2 Lofts Anna Maria Cottage Sleeps 14
Anna Maria Island & Holmes Beach

Luxury 4 Bedroom Plus 2 Lofts Anna Maria Cottage Sleeps 14

4 Bedrooms · 6 Bathrooms · Sleeps 14
From $699 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Bradenton 3 Bedroom Vacation Pool Home
Anna Maria Island & Holmes Beach

Bradenton 3 Bedroom Vacation Pool Home

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $7,591 / month
Call to confirm availability941.500.4555 Request a callback & quote
Silver Bradenton Luxury Four Bedroom Pool Home Sleeps 8 Guests
Anna Maria Island & Holmes Beach

Bradenton Luxury Four Bedroom Pool Home Sleeps 8 Guests

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $190 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Charming Vacation Rental on Bradenton. Call Today
Anna Maria Island & Holmes Beach

Charming Vacation Rental on Bradenton. Call Today

4 Bedrooms · 2 Bathrooms · Sleeps 8
From $532 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Bradenton 3 Bedroom Vacation Home Sleeps 6 Guests Caged Pool
Anna Maria Island & Holmes Beach

Bradenton 3 Bedroom Vacation Home Sleeps 6 Guests Caged Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $240 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Bradenton Vacation Rental Home Three Bedrooms
Anna Maria Island & Holmes Beach

Bradenton Vacation Rental Home Three Bedrooms

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $218 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Value Anna Maria Vacation Rentals 3 Bedrooms Sleeps 8 Pool
Anna Maria Island & Holmes Beach

Value Anna Maria Vacation Rentals 3 Bedrooms Sleeps 8 Pool

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $309 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Holmes Beach 3 Bedroom Pool Home Walk To Beach Sleeps 6
Anna Maria Island & Holmes Beach

Holmes Beach 3 Bedroom Pool Home Walk To Beach Sleeps 6

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $311 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Anna Maria Island Vacation Accommodation
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Accommodation

3 Bedrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Silver Private Pool Vacation Home Close to Beach & Dining
Anna Maria Island & Holmes Beach

Private Pool Vacation Home Close to Beach & Dining

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $302 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver This Vacation Cottage 3 Min Walk to Our World Class Beaches
Anna Maria Island & Holmes Beach

This Vacation Cottage 3 Min Walk to Our World Class Beaches

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $988 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Anna Maria Vacation Rental Home Three Bedrooms
Anna Maria Island & Holmes Beach

Anna Maria Vacation Rental Home Three Bedrooms

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $399 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Charming Cottage with Heated Pool, Close to Gulf Beaches
Anna Maria Island & Holmes Beach

Charming Cottage with Heated Pool, Close to Gulf Beaches

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

Anna Maria Island 2 Bedroom Private Pool Vacation Rental

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $279 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Holmes Beach Vacation Home with 2 Bedrooms Sleeps 6
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Home with 2 Bedrooms Sleeps 6

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $301 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Cozy Anna Maria Island Retreat with Private Pool
Anna Maria Island & Holmes Beach

Cozy Anna Maria Island Retreat with Private Pool

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $352 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Three Bedrooms Vacation Rental Sleeps 6 Short Walk to Beach
Anna Maria Island & Holmes Beach

Three Bedrooms Vacation Rental Sleeps 6 Short Walk to Beach

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $434 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Anna Maria Three Bedroom Vacation Rental Sleeps 8 Guests
Anna Maria Island & Holmes Beach

Anna Maria Three Bedroom Vacation Rental Sleeps 8 Guests

3 Bedrooms · 2 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Silver Three Bedroom Vacation Home Sleeps 6 Private Pool
Anna Maria Island & Holmes Beach

Three Bedroom Vacation Home Sleeps 6 Private Pool

3 Bedrooms · 1 Bathroom · Sleeps 6
From $15,952,495 / week
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.