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 937–960 of 1,169 matching vacation rentals, page 40 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
Filters Private pool — remove this filter Clear all
Gold Five Bedroom Anna Maria Home with Water Slide Pool & Views
Anna Maria Island & Holmes Beach

Five Bedroom Anna Maria Home with Water Slide Pool & Views

5 Bedrooms · 3 Bathrooms · Sleeps 10
From $2,336 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold North End Anna Maria Vacation Rental with Pool Sleeps 8
Anna Maria Island & Holmes Beach

North End Anna Maria Vacation Rental with Pool Sleeps 8

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,571 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Pool Home Blocks from the Beach in Anna Maria
Anna Maria Island & Holmes Beach

Luxury Pool Home Blocks from the Beach in Anna Maria

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,139 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Bayfront Luxury Home Sleeps 15 with Pool & Spa
Anna Maria Island & Holmes Beach

Anna Maria Bayfront Luxury Home Sleeps 15 with Pool & Spa

6 Bedrooms · 4 Bathrooms · Sleeps 15
From $2,186 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Waterfront Anna Maria Rental Home 3 Minute Walk to Beaches
Anna Maria Island & Holmes Beach

Waterfront Anna Maria Rental Home 3 Minute Walk to Beaches

6 Bedrooms · 4 Bathrooms · Sleeps 18
From $1,630 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Beach Rental Large Heated Pool Beach Across Street
Anna Maria Island & Holmes Beach

Bradenton Beach Rental Large Heated Pool Beach Across Street

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $1,420 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Vacation Rental on Anna Maria Island with 4 Bedrooms
Anna Maria Island & Holmes Beach

Vacation Rental on Anna Maria Island with 4 Bedrooms

4 Bedrooms · 4 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold One of the Best 5 Bedroom Homes on Anna Maria with Boat Dock
Anna Maria Island & Holmes Beach

One of the Best 5 Bedroom Homes on Anna Maria with Boat Dock

5 Bedrooms · 5 Bathrooms · Sleeps 6
From $2,386 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Villa a short stroll to beautiful white sandy beaches
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Villa a short stroll to beautiful white sandy beaches

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $1,595 / week
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Value Priced Pool Vacation Rental Home 3 Bedrooms
Anna Maria Island & Holmes Beach

Anna Maria Value Priced Pool Vacation Rental Home 3 Bedrooms

3 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Luxury Canal Front Pool Home Short Walk To Beach
Anna Maria Island & Holmes Beach

Anna Maria Luxury Canal Front Pool Home Short Walk To Beach

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

Holmes Beach Vacation Rental Home 3 Bedrooms Sleeps 6 Guests

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

Anna Maria Bean Point Vacation Home Sleeps 8 - Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Affordable Three Bedrooms 2 Bathrooms
Anna Maria Island & Holmes Beach

Affordable Three Bedrooms 2 Bathrooms

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

Holmes Beach Vacation Home With Private Pool

6 Bedrooms · 4 Bathrooms · Sleeps 12
From $350 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury 8-Bedroom Anna Maria Island Vacation Rental with Private Pool & Gulf Views Holmes Beach
Anna Maria Island & Holmes Beach

Luxury 8-Bedroom Anna Maria Island Vacation Rental with Private Pool & Gulf Views Holmes Beach

8 Bedrooms · 5 Bathrooms · Sleeps 16
From $2,904 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria 7 Bedroom Private Pool Vacation Beach Home
Anna Maria Island & Holmes Beach

Anna Maria 7 Bedroom Private Pool Vacation Beach Home

7 Bedrooms · 7 Bathrooms · Sleeps 18
From $1,995 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Three Bedroom Rental Home Great Interior Decor
Anna Maria Island & Holmes Beach

Anna Maria Three Bedroom Rental Home Great Interior Decor

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,195 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island 4 Bedroom Canal Front Rental Private Pool
Anna Maria Island & Holmes Beach

Anna Maria Island 4 Bedroom Canal Front Rental Private Pool

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,850 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Three Bedroom Holmes Beach Townhome Close To The Beach
Anna Maria Island & Holmes Beach

Three Bedroom Holmes Beach Townhome Close To The Beach

3 Bedrooms · 3 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria 3 Bedroom Vacation Rental with Pool Peeks of Gulf
Anna Maria Island & Holmes Beach

Anna Maria 3 Bedroom Vacation Rental with Pool Peeks of Gulf

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,300 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Luxury Vacation Home 5 houses to beach
Anna Maria Island & Holmes Beach

Anna Maria Luxury Vacation Home 5 houses to beach

5 Bedrooms · 4 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Vacation Home 6 Bedrooms Anna Maria Island Sleeps 12 Steps to Beach
Anna Maria Island & Holmes Beach

Luxury Vacation Home 6 Bedrooms Anna Maria Island Sleeps 12 Steps to Beach

6 Bedrooms · 3 Bathrooms · Sleeps 12
From $1,792 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Luxury Six Bedroom Home Walk To Beach
Anna Maria Island & Holmes Beach

Anna Maria Luxury Six Bedroom Home Walk To Beach

6 Bedrooms · 5 Bathrooms · Sleeps 14
Call for rates
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.