Large-Scale Family Estates Curated for Connection

Our Casa Mariposa vacation rental home is the definition of luxury. With a heated pool and spa in the foreground, surrounded by beautiful landscaping on a private patio, you can see the home in the background of the image, with it's expansive, screened-in porch. This home is just off of Pine Avenue and in walking distance to the beach.

True luxury is having your own space in a shared house. We designed these estates for the grandparents, the toddlers, and everyone in between. Enjoy a layout that offers deep connection without sacrificing privacy.

Our collection of 4-bedroom vacation rentals on Anna Maria Island blends coastal elegance with modern comfort. Perfect for families or groups, each home features spacious living areas, fully equipped kitchens, and beautifully designed bedrooms for a truly relaxing stay. Step outside to enjoy private pools, sun-soaked lounge areas, and breathtaking sunset views.

Just moments from the island’s sugar-white beaches, these premium rentals offer easy access to top dining, boutique shopping, and endless outdoor adventures. Looking for something different? Explore our 2-, 3-, and 5+ bedroom rentals for the perfect island getaway.

Browse our pet-friendly vacation rentals on Anna Maria Island and discover the perfect beach home for you and your furry friend. Enjoy prime locations and luxury amenities.


Pet friendly 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

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 12 properties available
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
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Mango Bay
Mango Bay
Holmes Beach
$330.00 - $830.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.7 (4)
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
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Sea La Vie Beach House
Sea La Vie Beach House
Anna Maria
$600.00 - $1,750.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (9)
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
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Serenity Now
Serenity Now
Holmes Beach Pet Friendly
$350.00 - $990.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (9)
Welcome to Casa Mariposa!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 Casa Mariposa — where the rhythm of island life slows, and beauty unfolds in every detail. Just one street north of Pine Avenue and four houses from the beach, thi
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Casa Mariposa
Casa Mariposa
Anna Maria
$520.00 - $1,500.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (13)
Welcome to Hangin’ on Hammock!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Please Note: The pool and spa are currently under construction and are scheduled for completion by May 2026. Construction is set to begin January 1, 2026. Because the po
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Hangin on Hammock
Hangin on Hammock
Anna Maria Pet Friendly
$380.00 - $890.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Island Girl East & West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units: Island Girl East & Island Girl West*The SpaceWith room for up to 10 guests, Island Girl East & West is thoughtfully designed for shared experiences and easy island living. Each side of t
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Island Girl - East & West
Island Girl - East & West
Holmes Beach Pet Friendly
$305.00 - $810.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (6)
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
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Tern Key
Tern Key
Anna Maria
$900.00 - $1,850.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (8)
Welcome to Bateman's!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 Bateman’s — where thoughtful design and waterfront living come together.Set along a quiet canal on Anna Maria Island’s north end, this modern coastal h
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Bateman's
Bateman's
Anna Maria
$600.00 - $1,900.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (14)
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
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Three Little Birds
Three Little Birds
Anna Maria
$800.00 - $1,950.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (2)
Welcome to She's Always Right!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 thoughtful design meets island energy, She’s Always Right blends modern artistry, resort-style comfort, and an unbeatable location just steps from t
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She's Always Right
She's Always Right
Holmes Beach Pet Friendly
$380.00 - $1,080.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (17)
Welcome to The Curated Palm!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 SpaceThe Curated Palm is a home that feels at once elevated and effortless — where thoughtful craftsmanship, inspired design, and island living align in perfect h
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The Curated Palm
The Curated Palm
Anna Maria
$750.00 - $2,100.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (5)
Welcome to AcquaLuxe!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 AcquaLuxe — a canal-front home designed for inspiration, connection, and ease.The SpaceNestled near Anna Maria Island’s beloved north-end beaches and Pine Avenue
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.AcquaLuxe
.AcquaLuxe
Anna Maria
$650.00 - $2,050.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (12)

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