Two Bedroom Vacation Rentals

The Cottage on Pine, one of our two bedroom luxury vacation rentals, with a stone blue exterior, white trim, and tan doors. This vacation rental is located on Pine Avenue, within walking distance of Anna Maria Island's boutique shops, top restaurants, and Gulf beaches. It also has a private pool.

Find your perfect two-bedroom vacation rental on Anna Maria Island! Enjoy prime locations, luxury amenities, and easy access to beaches, dining, and shopping. 

From pet-friendly retreats to homes just steps from the shore, we have the ideal spot for your getaway.

Need more space? 

Check out our 3-, 4-, and 5+ bedroom rentals.

Explore the collection of waterfront vacation rentals on Anna Maria Island and find your perfect beach getaway. Wake up to breathtaking views, unwind in style, and experience the best of island living.


Waterfront Rentals

Browse our pet-friendly vacation rentals on Anna Maria Island and discover the perfect beach home for you and your furry friend. Enjoy easy access to the island’s top beaches, dining, and attractions.


Pet friendly rentals

View our selection of vacation rentals with private pools on Anna Maria Island. Enjoy a refreshing dip any time of day, spacious outdoor living areas, and the perfect blend of relaxation and island charm.


Private Pool Rentals
Properties Available 9 properties available
Welcome to Catching Waves!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Catching Waves — where laid-back island living meets everyday adventure. Just a short stroll to the white-sand beaches of Holmes Beach, this ground-level h
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Catching Waves
Catching Waves
Holmes Beach Pet Friendly
$225.00 - $650.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
Welcome to Sunset Margarita!Bradenton, Florida (Just off Anna Maria Island, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.The SpaceSet within Margaritaville’s One Particular Harbour waterfront community, Sunset Margarita blends modern finishes with easy, resort-style living. This third-f
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Sunset Margarita
Sunset Margarita
Off Island Pet Friendly
$210.00 - $420.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (3)
Welcome to Island Girl East!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit: Island Girl East*Discover Island Girl East, a bright coastal retreat just five houses from the beach. Here, mornings begin with the sound of swaying palms, and afternoons drift between the pool and the sea.
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Island Girl East
Island Girl East
Holmes Beach
$205.00 - $490.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (1)
Welcome to Cozy Cabana West!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Where slow mornings and quiet evenings meet the rhythm of island life.Just a short stroll from Holmes Beach, this thoughtfully designed bungalow invites guests to rest, r
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Cozy Cabana West
Cozy Cabana West
Holmes Beach Pet Friendly
$275.00 - $700.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
Welcome to The Cottage on Pine!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceStep inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmos
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The Cottage on Pine
The Cottage on Pine
Anna Maria Pet Friendly
$250.00 - $731.80 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (10)
Welcome to Kokomo!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceDiscover Kokomo, where comfort meets calm in a thoughtfully updated beach cottage just a short walk from the Gulf of Mexico. Designed for rest and reconnection, this home
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Kokomo
Kokomo
Holmes Beach
$225.00 - $680.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Welcome to Cozy Cabana East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover Cozy Cabana East, where comfort, care, and connection come together in a thoughtfully designed, single-level home just a short walk from the beach. Blending
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Cozy Cabana East
Cozy Cabana East
Holmes Beach Pet Friendly
$255.00 - $680.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (9)
Welcome to Fins Up!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceYour serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenie
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Fins Up
Fins Up
Holmes Beach
$275.00 - $710.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (14)
Welcome to Island Girl West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit: Island Girl West*Step inside Island Girl West, where natural textures, sunlight, and soft coastal hues set the tone for your stay. The open layout invites easy flow between kitchen, dining, and living spaces
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Island Girl West
Island Girl West
Holmes Beach
$205.00 - $490.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (3)

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