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

Properties Available 7 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.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
Hot HOT 23
Catching Waves
Catching Waves
Holmes Beach Pet Friendly
$260.00 - $650.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
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
Hot HOT 12
Decked Out
Decked Out
Anna Maria
$310.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (14)
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
Hot HOT 38
Fins Up
Fins Up
Holmes Beach
$310.00 - $710.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (10)
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
Hot HOT 23
Cozy Cabana East
Cozy Cabana East
Holmes Beach Pet Friendly
$280.00 - $680.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
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
Hot HOT 14
Casa Posada
Casa Posada
Anna Maria Pet Friendly
$250.00 - $500.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 5 (3)
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
Hot HOT 24
On Turtle Time
On Turtle Time
Holmes Beach Pet Friendly
$260.00 - $650.00 / 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.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
Hot HOT 31
The Cottage on Pine
The Cottage on Pine
Anna Maria Pet Friendly
$275.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (4)

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