0 941.500.4555 Request a Call

2 Bedroom Anna Maria Island & Holmes Beach Vacation Rentals

Browse 2,058 professionally managed vacation rentals with at least 2 bedrooms in Anna Maria Island & Holmes Beach with Emerald Kite. Showing 1–24 of 2,058 matching vacation rentals, page 1 of 86. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
Filters 2+ bedrooms — remove this filter Clear all
Platinum Stylish Luxury Beachside Two Bedroom Anna Maria
Anna Maria Island & Holmes Beach

Stylish Luxury Beachside Two Bedroom Anna Maria

2 Bedrooms · 2 Bathrooms · Sleeps 8
From $1,776 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Bradenton Vacation Condo Two Bedrooms Walk to Beach
Anna Maria Island & Holmes Beach

Luxury Bradenton Vacation Condo Two Bedrooms Walk to Beach

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $905 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Waterfront Vacation Rental with Bay Views Private Dock & Beach Access
Anna Maria Island & Holmes Beach

Anna Maria Island Waterfront Vacation Rental with Bay Views Private Dock & Beach Access

2 Bedrooms · 2 Bathrooms · Sleeps 4
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Two bedroom Vacation Condo Views of the Gulf of Mexico
Anna Maria Island & Holmes Beach

Anna Maria Island Two bedroom Vacation Condo Views of the Gulf of Mexico

2 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Duplex With Private Pool And Game Room
Anna Maria Island & Holmes Beach

Holmes Beach Duplex With Private Pool And Game Room

2 Bedrooms · 1 Bathroom · Sleeps 6
From $556 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Condo With Gulf Views And Heated Pools
Anna Maria Island & Holmes Beach

Holmes Beach Condo With Gulf Views And Heated Pools

2 Bedrooms · 2 Bathrooms · Sleeps 4
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming Beach Getaway in Anna Maria Island
Anna Maria Island & Holmes Beach

Charming Beach Getaway in Anna Maria Island

2 Bedrooms · 1 Bathroom · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria 8 Min Stroll To the Beach Pool, Tennis Beach
Anna Maria Island & Holmes Beach

Anna Maria 8 Min Stroll To the Beach Pool, Tennis Beach

2 Bedrooms · 2 Bathrooms · Sleeps 4
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Rental with Private Pool – Island Villa
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Rental with Private Pool – Island Villa

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $677 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold A Rare Find Holmes Beach Rental Direct Beach Walk- Out
Anna Maria Island & Holmes Beach

A Rare Find Holmes Beach Rental Direct Beach Walk- Out

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $880 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beachside Two Bedroom Triplex Vacation Rental in Holmes Beach
Anna Maria Island & Holmes Beach

Beachside Two Bedroom Triplex Vacation Rental in Holmes Beach

2 Bedrooms · 1 Bathroom · Sleeps 4
From $479 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming 2 Bedroom Vacation Home with Private Pool
Anna Maria Island & Holmes Beach

Charming 2 Bedroom Vacation Home with Private Pool

2 Bedrooms · 2 Bathrooms · Sleeps 5
From $344 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming Water Side NEW POOL WOW Anna Maria Island
Anna Maria Island & Holmes Beach

Charming Water Side NEW POOL WOW Anna Maria Island

2 Bedrooms · 3 Bathrooms · Sleeps 4
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lake Front Two Bedroom Rental Condo in Lakewood Ranch
Anna Maria Island & Holmes Beach

Lake Front Two Bedroom Rental Condo in Lakewood Ranch

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $5,450 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lovely 2 Bedroom Vacation Rental with Waterfront Views
Anna Maria Island & Holmes Beach

Lovely 2 Bedroom Vacation Rental with Waterfront Views

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $190 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Just In! What A Lovely New 2 Bedroom Beach Condo in Holmes Beach
Anna Maria Island & Holmes Beach

Just In! What A Lovely New 2 Bedroom Beach Condo in Holmes Beach

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $538 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Gulf Front End Unit on Beach
Anna Maria Island & Holmes Beach

Holmes Beach Gulf Front End Unit on Beach

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $600 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Private Half Duplex Anna Maria Island
Anna Maria Island & Holmes Beach

Private Half Duplex Anna Maria Island

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $673 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Imagine Your Very own Private Pool Home
Anna Maria Island & Holmes Beach

Imagine Your Very own Private Pool Home

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $930 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bay Views Vacation Pools Home in Holmes Beach
Anna Maria Island & Holmes Beach

Bay Views Vacation Pools Home in Holmes Beach

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $14,172 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Gulf Views Bradenton Beach Vacation Condo
Anna Maria Island & Holmes Beach

Gulf Views Bradenton Beach Vacation Condo

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $439 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming Two Bedroom Vacation Duplex in Holmes Beach
Anna Maria Island & Holmes Beach

Charming Two Bedroom Vacation Duplex in Holmes Beach

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $506 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beautiful Eco-Friendly Vacation Home in Cortez, FL
Anna Maria Island & Holmes Beach

Beautiful Eco-Friendly Vacation Home in Cortez, FL

2 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Gulf & Bay Views Two Vacation Rental in Bradenton Beach
Anna Maria Island & Holmes Beach

Gulf & Bay Views Two Vacation Rental in Bradenton Beach

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,188 / 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.