Bradenton Beach Vacation Rentals

Our homes in Bradenton Beach is where coastal energy meets refined island living. Positioned between the Gulf and the bay, this area offers a dynamic experience with stunning water views, walkable access to Bridge Street, and some of the island’s most iconic spots.

Each home is selected for its design, location, and experience, creating a stay that blends vibrant surroundings with the elevated, boutique feel of Once Upon A Beach.



Properties Available 5 properties available
Welcome to Mariner's Crossing!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceSet between the Gulf of Mexico and the Intracoastal Waterway, Mariner’s Crossing offers balance — connection and privacy, activity and calm. With
Hot HOT 43
Mariner's Crossing
Bradenton Beach
$800.00 - $3,300.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.9 (15)
Welcome to Family Tides!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units; Family Tides A & Family Tides B*Where gathering comes naturally and every generation finds its place in the sun.Just steps from the Gulf of Mexico in Bradenton Beach, this dual-home property offers
Hot HOT 48
Family Tides
Bradenton Beach
$450.00 - $1,860.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 16 guests
Rating 4.9 (10)
Welcome to Family Tides – Unit BOn Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides B (Top Unit)*Set above its sister unit in this beautiful duplex, this light-filled home offers space for connection and comfort, with access to shared outdoor amenities designed for
Your Vacation Story: Your Vacation Story:
Your Vacation Story:
Enjoy modern comfort and coastal charm in this bright, open retreat. Gather in the inviting living space, relax by the heated pool, or take in stunning views from the shared rooftop deck.
Family Tides - B
Bradenton Beach
$280.00 - $980.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4 (1)
Welcome to Ocean Sunrise!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation RentalsThe SpaceSet directly on the Bay in Bradenton Beach, Ocean Sunrise offers 4,793 square feet of bright, inviting living. The design balances elegance and ease—sun-filled rooms, expansive gathering spaces, and a backyard where the lin
Hot HOT 24
Ocean Sunrise
Bradenton Beach
$700.00 - $2,450.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 20 guests
Rating 5 (2)
Welcome to Family Tides – Unit A!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides A (Bottom Unit)*Located just steps from the Gulf of Mexico and walkable to Bridge Street, this ground-level unit invites you to unwind, connect, and enjoy a thoughtfully
Hot HOT 11
Family Tides - A
Bradenton Beach
$42.00 - $980.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests

Tell us what you're looking for and someone will contact you with available options.

I agree