You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

40 properties available

Welcome to Sea La Vie Beach House!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 SpaceWhere connection meets calm, Sea La Vie Beach House brings family, friends, and loved ones together in a space designed for comfort, laughter, and easy island liv

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

Sea La Vie Beach House

Anna Maria

$600^.00 - $1,925^.00 / per night

Welcome to La Buena Vida!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 SpaceMornings begin with sunlight dancing across the canal and coffee enjoyed on the screened porch. Days unfold between the pool, the dock, and the nearby beach—each mom

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

La Buena Vida

Anna Maria

$380^.00 - $979^.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*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.

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

Island Girl East

Holmes Beach

$205^.00 - $490^.00 / per night

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

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

Ocean Sunrise

Bradenton Beach

$700^.00 - $2,750^.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.The SpaceThoughtfully redesigned for simplicity and comfort, On Turtle Time blends the charm of an island cottage with the ease of modern living. Inside, natural light filt

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

On Turtle Time

Holmes Beach

$240^.00 - $650^.00 / per night

Welcome to Serenity Now!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 SpaceWhere calm meets connection, Serenity Now offers spacious living, modern comforts, and a private backyard oasis with a heated pool. Thoughtfully designed for ease and bal

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

Serenity Now

Holmes Beach

$380^.00 - $960^.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.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

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

Cozy Cabana West

Holmes Beach

$275^.00 - $700^.00 / per night

Welcome to Coconut Lagoon!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 into Coconut Lagoon, where generations of island charm meet easy, family-focused living. Nestled along the beloved Magnolia Avenue—lined with palms, bike

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

Coconut Lagoon

Anna Maria

$385^.00 - $935^.00 / per night

Welcome to Cortez Dock & Dine!On Florida’s Gulf Coast (Cortez, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A rare waterfront escape blending Old Florida charm with modern coastal living.Please note: Boat not included with rental. For more information about boat rental

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

Cortez Dock & Dine

Off Island

$240^.00 - $520^.00 / per night

4 bedrooms

3 baths

10 guests

Welcome to Three Little Birds!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 into Three Little Birds — a bright, joyful island home designed for gathering, connecting, and letting the days unfold naturally. With Gulf views, a privat

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

Three Little Birds

Anna Maria

$800^.00 - $2,145^.00 / per night

Welcome to Mango Bay!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Set on a quiet street near the sand, Mango Bay blends open interiors with plenty of outdoor living. Upstairs, the main living floor brings kitchen, dining, and lounge spaces together

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

Mango Bay

Holmes Beach

$370^.00 - $830^.00 / per night

Welcome to Tern Key!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 SpaceTern Key is a home that feels both artful and effortless — where every line, light, and texture come together in perfect harmony. The moment you step inside, the canal vi

Special

You Found Us for a Reason… Here’s a Little Something Extra ☀️

If you’re seeing this, it means you found us the fun way… through a scroll, a sunset, or a moment that made you pause and think, “I need to be there.” 🌴

We think that deserves something a little extra.

Book Direct. Get More.

When you book your stay directly with us, you’ll receive 5% off your reservation using code:

WRITEYOURSTORY

Because your vacation shouldn’t just be a booking… it should feel like the beginning of something.

Why Book Direct?

Best available rates, without platform fees
Personalized support from our local team
Access to exclusive offers you won’t find anywhere else
A more seamless, elevated guest experience from start to finish

Whether it’s your first time on Anna Maria Island or your favorite place to return to, we’re here to help you create something that feels effortless, memorable, and entirely your own.

Ready to start planning?

📞 Call or text: (941) 584-5844
📧 [email protected]

Tern Key

Anna Maria

$900^.00 - $2,035^.00 / per night

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