0 941.500.4555 Request a Call

Anna Maria Island & Holmes Beach Vacation Rentals

Showing 433–456 of 2,224 matching vacation rentals, page 19 of 93. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
Gold 4 Bedroom Getaway with Large Private Pool, Spa & Bay Views
Anna Maria Island & Holmes Beach

4 Bedroom Getaway with Large Private Pool, Spa & Bay Views

4 Bedrooms · 3 Bathrooms · Sleeps 10
From $1,183 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna MariaI sland Vacation Home Four Bedroom
Anna Maria Island & Holmes Beach

Anna MariaI sland Vacation Home Four Bedroom

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $655 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Luxury Vacation Villa West of Gulf Drive
Anna Maria Island & Holmes Beach

Anna Maria Island Luxury Vacation Villa West of Gulf Drive

5 Bedrooms · 3 Bathrooms · Sleeps 12
From $1,750 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lovely Pool Home Away From Home North End Anna Maria
Anna Maria Island & Holmes Beach

Lovely Pool Home Away From Home North End Anna Maria

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,588 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming 2 Bedroom Condo in Holmes Beach
Anna Maria Island & Holmes Beach

Charming 2 Bedroom Condo in Holmes Beach

2 Bedrooms · 1 Bathroom · Sleeps 4
From $972 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Three Bedroom Home Close to Pine Ave & Beach Point Beach
Anna Maria Island & Holmes Beach

Three Bedroom Home Close to Pine Ave & Beach Point Beach

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $1,405 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Vacation Home Three Bedroom Walk to Beach
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Home Three Bedroom Walk to Beach

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $1,076 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Home Four Bedroom Walk to Beach
Anna Maria Island & Holmes Beach

Anna Maria Vacation Home Four Bedroom Walk to Beach

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $2,688 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Discover Your Ideal Getaway at Our Cozy Bradenton Home
Anna Maria Island & Holmes Beach

Discover Your Ideal Getaway at Our Cozy Bradenton Home

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $430 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lakewood National Vacation Condo Three Bedroom
Anna Maria Island & Holmes Beach

Lakewood National Vacation Condo Three Bedroom

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $6,909 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Lovely 2 Bedroom Vacation Condo
Anna Maria Island & Holmes Beach

Bradenton Lovely 2 Bedroom Vacation Condo

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $213 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Bradenton Vacation Rental: Pool, Spa & Golf
Anna Maria Island & Holmes Beach

Luxury Bradenton Vacation Rental: Pool, Spa & Golf

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $11,018 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Lakewood Ranch Vacation Rental with Great Views
Anna Maria Island & Holmes Beach

Luxury Lakewood Ranch Vacation Rental with Great Views

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $4,122 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lakefront Vacation Condo in Lakewood Ranch with Luxury Amenities
Anna Maria Island & Holmes Beach

Lakefront Vacation Condo in Lakewood Ranch with Luxury Amenities

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $7,611 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lovely Vacation Rental 2 Bedrooms with Waterfront Views
Anna Maria Island & Holmes Beach

Lovely Vacation Rental 2 Bedrooms with Waterfront Views

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $190 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxurious Lakewood Ranch Pool Residence
Anna Maria Island & Holmes Beach

Luxurious Lakewood Ranch Pool Residence

3 Bedrooms · 2 Bathrooms · Sleeps 5
From $16,557 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Island Oasis with 3 Bedrooms & Great Amenities
Anna Maria Island & Holmes Beach

Island Oasis with 3 Bedrooms & Great Amenities

3 Bedrooms · 3 Bathrooms · Sleeps 7
From $638 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lovely 4 Bedroom Home in Palmetto with Pool
Anna Maria Island & Holmes Beach

Lovely 4 Bedroom Home in Palmetto with Pool

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $614 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beautiful Three Bedroom Home in Bradenton Sleeps Six Guests
Anna Maria Island & Holmes Beach

Beautiful Three Bedroom Home in Bradenton Sleeps Six Guests

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $714 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Vacation Pool Home Four Bedrooms Sleeps 11
Anna Maria Island & Holmes Beach

Bradenton Vacation Pool Home Four Bedrooms Sleeps 11

4 Bedrooms · 3 Bathrooms · Sleeps 11
From $658 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Bradenton 3 Bedroom Home Sleeps 6 With Private Pool
Anna Maria Island & Holmes Beach

Luxury Bradenton 3 Bedroom Home Sleeps 6 With Private Pool

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

Water Views Holmes Beach Vacation Pool Home Five Bedroom

5 Bedrooms · 3 Bathrooms · Sleeps 10
From $1,388 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beautiful Anna Maria Vacation Home with Pool & Hot Tub
Anna Maria Island & Holmes Beach

Beautiful Anna Maria Vacation Home with Pool & Hot Tub

5 Bedrooms · 4 Bathrooms · Sleeps 14
From $1,789 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Gorgeous Anna Maria Vacation Home with Private Pool & Spa
Anna Maria Island & Holmes Beach

Gorgeous Anna Maria Vacation Home with Private Pool & Spa

5 Bedrooms · 3 Bathrooms · Sleeps 10
From $1,802 / 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.