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.

Discover the perfect 2-bedroom vacation rental on Anna Maria Island, Florida! Browse our extensive selection of Anna Maria Island vacation homes to find the ideal Florida beach house for your next romantic getaway, complete with stunning locations, luxury amenities, and close proximity to the island's best dining, shopping, and attractions.

Smaller in size but not in charm, our two bedroom Anna Maria Island homes keep you close to everything the island has to offer, while ensuring you have every amenity needed for a luxurious retreat. Whether you'd like to stay in a home within walking distance to the beach or enjoy a pet friendly getaway, you'll find everything you're looking for at Once Upon a Beach. Check out our concierge services to learn more!

Looking for a larger space? We also have 3 Bedroom, 4 Bedroom, and 5+ Bedroom vacation rentals available!

Vacation rentals by amenity

Pet friendly vacation rentals Private pool vacation rentals Waterfront vacation rentals

11 properties available

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.A cozy vacation home with a private heated pool, just a 4-minute walk to the beach, complete with everything you need for an unforgettable stay!HIGHLIGHTS: Living Space: 1

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Fins Up

Holmes Beach

$310^.00 - $710^.00 / per night

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*Island Girl West offers a luxurious and spacious retreat near Holmes Beach with room for up to 5 guests, featuring wraparound decks, a gourmet kitchen, a shared heated pool, and easy access

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Island Girl West

Holmes Beach

$225^.00 - $490^.00 / per night

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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and co

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Catching Waves

Holmes Beach

$260^.00 - $650^.00 / per night

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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—with temporary updated picture

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Cozy Cabana West

Holmes Beach

$297^.00 - $710^.00 / per night

Welcome to On Turtle Time!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and co

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On Turtle Time

Holmes Beach

$260^.00 - $650^.00 / per night

Welcome to Casa Posada!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience the charm of old Florida living with modern comforts at Casa Posada, a historic ground-floor cottage just steps from the Gulf-side beaches.1050 sq. ft. of Cozy Cottage Com

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Casa Posada

Anna Maria

$250^.00 - $500^.00 / per night

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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comf

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The Cottage on Pine

Anna Maria

$275^.00 - $720^.00 / per night

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.Relax and Unwind in a Stunning Coastal Retreat, Just Minutes from Anna Maria Island Beaches!HIGHLIGHTS: Spacious Layout: Third-floor condo with 2 bedrooms and 2 bathro

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Sunset Margarita

Off Island

$205^.00 - $410^.00 / per night

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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—with updated pictures as

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Cozy Cabana East

Holmes Beach

$280^.00 - $680^.00 / per night

Welcome to Decked Out!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience the ultimate island retreat at Decked Out, a luxurious 2-bedroom elevated home with high-end furnishings, a heated pool, and prime access to Anna Maria's bay and G

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Decked Out

Anna Maria

$310^.00 - $720^.00 / per night

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*Island Girl East offers a luxurious and spacious retreat near Holmes Beach with room for up to 5 guests, featuring decks, a gourmet kitchen, a shared heated pool, and easy access to Anna Mar

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Island Girl East

Holmes Beach

$225^.00 - $490^.00 / per night

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