AVAILABILITY CALENDAR
VIEW THE WHOLE YEAR AT A GLANCE
CLICK HERE to see all openings for your dates
USA TOLL FREE
UK FREE PHONE
DE FREE PHONE

Anna Maria Island 1 & 2 Bedroom Vacation Rentals

View Rentals Below

Anna Maria Vacations is the source for luxury Anna Maria Island vacation rentals. This quaint seaside town is slowly rising up the ranks as one of the best vacation islands in the world and the very best in Florida. We have many rental homes to choose from including beachfront and dog friendly. If you would prefer renting a beachfront condo, we have those too.

Anna Maria Island has some of the most beautiful beaches and some of the best rental properties on the Gulf Coast. On this page we have one bedroom rentals that are perfect for a romantic getaway. It also features two bedroom homes for rent which are great for a couples retreat or for a small family vacation.

If you need more space and are looking for a larger home for rent, we also have 3 bedroom, 4 bedroom, and 5 plus bedroom rentals.

These rental homes can sleep up to 5 guests.

Sailfish Beach Resort Unit 2
Sailfish Beach Resort Unit 2
Weekly $938 - $3000 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Beach Bliss
Beach Bliss
Weekly $875 - $3150 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Southern Breeze 5
Southern Breeze 5
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
More details >
Shell Haven
Shell Haven
Weekly $900 - $3325 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Sunset Beach
Sunset Beach
Weekly $868 - $3150 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Redfish Cottage
Redfish Cottage
Weekly $600 - $1695 *
BBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 1/1 Sleeps: 2 Location: Cortez
More details >
Southern Breeze 1
Southern Breeze 1
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
More details >
Hidden Cove 5
Hidden Cove 5
Weekly $1200 - $3850 *
PoolInternetDeck Chairs
Bed & Bath: 2/2.5 Sleeps: 4 Location: Holmes Beach
More details >
Island Hideaway
Island Hideaway
Weekly $800 - $2800 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Moondance
Moondance
Weekly $1295 - $3850 *
Linen ServiceInternetDeck Chairs
Bed & Bath: 2/1.5 Sleeps: 4 Location: Anna Maria
More details >
Beach Life At The Pointe
Beach Life At The Pointe
Weekly $1295 - $3500 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Anna Maria Island Club 20
Anna Maria Island Club 20
Weekly $924 - $4305 *
PoolSpaElevatorInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach
More details >
Sun Plaza West 115
Sun Plaza West 115
Weekly $1100 - $3150 *
PoolInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Capri Condo C
Capri Condo C
Weekly $1000 - $3850 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 6 Location: Bradenton Beach
More details >
Coconut Cottage Unit 4
Coconut Cottage Unit 4
Weekly $903 - $3150 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Coquina Beach Club 203
Coquina Beach Club 203
Weekly $1000 - $3850 *
PoolLinen ServiceInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach
More details >
Beach Isle
Beach Isle
Weekly $875 - $4200 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Southern Breeze 6
Southern Breeze 6
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
More details >
Gulf Shores 106
Gulf Shores 106
Weekly $959 - $3850 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Bay Bella Vista
Bay Bella Vista
Monthly $4200 - $5132 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/3 Sleeps: 4 Location: Holmes Beach
More details >
Peacock Way
Peacock Way
Weekly $800 - $2625 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Sun Plaza West Unit 110
Sun Plaza West Unit 110
Weekly $525 - $2100 *
PoolLinen ServiceElevatorInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
The Terraces 6
The Terraces 6
Weekly $700 - $2450 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Turtle Way
Turtle Way
Weekly $861 - $2800 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Magnolia Breeze
Magnolia Breeze
Weekly $1000 - $3500 *
BBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 2/2 Sleeps: 5 Location: Anna Maria
More details >
Turtle Cove
Turtle Cove
Weekly $861 - $2800 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
A Sandbox by the Sea
A Sandbox by the Sea
Weekly $1400 - $4725 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 2/2 Sleeps: 6 Location: Anna Maria
More details >
Whispering Waves West
Whispering Waves West
Weekly $900 - $2450 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Southern Breeze 2
Southern Breeze 2
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
More details >
Tuna Cottage
Tuna Cottage
Weekly $575 - $1695 *
BBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 1/1 Sleeps: 2 Location: Cortez
More details >
Coquina Breeze
Coquina Breeze
Weekly $1000 - $3150 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 2/2.5 Sleeps: 4 Location: Bradenton Beach
More details >
Coast House
Coast House
Weekly $903 - $3850 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Waters Edge Condo 110N
Waters Edge Condo 110N
Weekly $1400 - $1729 *
PoolElevatorInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Southern Breeze 4
Southern Breeze 4
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
More details >
Runaway Bay
Runaway Bay
Weekly $1050 - $2750 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach
More details >
Hidden Oasis
Hidden Oasis
Weekly $1100 - $3605 *
InternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Anna Maria
More details >
Sailfish Beach Resort Unit 4
Sailfish Beach Resort Unit 4
Weekly $847 - $2900 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Island Paradise 4
Island Paradise 4
Weekly $1400 - $3850 *
PoolLinen ServiceInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Tropical Sunset 4
Tropical Sunset 4
Weekly $770 - $2975 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Sailfish Beach Resort Unit 3
Sailfish Beach Resort Unit 3
Weekly $847 - $2900 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
High Tide
High Tide
Weekly $1000 - $2835 *
InternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Anna Maria
More details >
Palm Isle Bungalow
Palm Isle Bungalow
Weekly $800 - $2730 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Sailfish Beach Resort Unit 1
Sailfish Beach Resort Unit 1
Weekly $938 - $3000 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Anna Maria Island Club 24
Anna Maria Island Club 24
Weekly $1575 - $4950 *
PoolSpaLinen ServiceElevatorInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach
More details >
Gulf Sands 102
Gulf Sands 102
Weekly $959 - $3500 *
PoolLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Sunny Side Up
Sunny Side Up
Weekly $1000 - $3500 *
BBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 2/2 Sleeps: 6 Location: Anna Maria
More details >
Island Paradise 1
Island Paradise 1
Weekly $1925 - $4900 *
PoolLinen ServiceInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Sunset Terrace 104
Sunset Terrace 104
Weekly $1000 - $2975 *
PoolInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach
More details >
Whispering Waves East
Whispering Waves East
Weekly $798 - $2450 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Island Breeze
Island Breeze
Weekly $1400 - $4200 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 6 Location: Anna Maria
More details >
Low Tide
Low Tide
Weekly $1050 - $2688 *
InternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 4 Location: Anna Maria
More details >
Gulf Breeze Condo Unit D
Gulf Breeze Condo Unit D
Weekly $1000 - $2100 *
Linen ServiceElevatorInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Bradenton Beach
More details >
Island Escape
Island Escape
Weekly $812 - $3500 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
The Gulf Front
The Gulf Front
Weekly $1400 - $3850 *
PoolLinen ServiceElevatorInternetDeck Chairs
Bed & Bath: 2/2.5 Sleeps: 4 Location: Holmes Beach
More details >
Coconut Cottage Unit 3
Coconut Cottage Unit 3
Weekly $903 - $3150 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
More details >
Hidden Cove 4
Hidden Cove 4
Weekly $1200 - $3850 *
PoolLinen ServiceInternetDeck Chairs
Bed & Bath: 2/2.5 Sleeps: 4 Location: Holmes Beach
More details >
Salty Dog
Salty Dog
Weekly $854 - $3150 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 4 Location: Holmes Beach
More details >
Southern Breeze 3
Southern Breeze 3
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
More details >
*Rates shown are estimates. Excludes Taxes, Fees and Travel Insurance.
Loading...