Three Bedroom Vacation Rentals

Our Sol Mate vacation rental property, showing a heated pool and spa in the foreground, and surrounded by lush, tropical landscaping. The home is three stories and has two screened-in patios. This Once Upon a Beach luxury vacation rental comes with an outdoor bar with a TV, grill & ample seating. And it's within walking distance to Bean Point’s beaches and Pine Avenue’s shops and eateries.

Indulge in a luxurious three-bedroom vacation rental on Anna Maria Island, where upscale comfort meets coastal elegance. Perfect for families or small groups, these homes feature modern interiors, premium amenities, and beautifully designed outdoor spaces for the ultimate island retreat.

Located just steps from the island’s pristine beaches - you’ll enjoy effortless access to fine dining, boutique shopping, and activities like biking, kayaking, and fishing. Need more or less space? Explore our exclusive 2-, 4-, and 5+ bedroom rentals to fit your dream getaway.

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

Browse our pet-friendly vacation rentals on Anna Maria Island and discover the perfect beach home for you and your furry friend. Enjoy luxury amenities and easy access to dining and attractions.


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 14 properties available
Welcome to Sandy Pants!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 creativity meets coastal calm, Sandy Pants brings modern design and island ease together just steps from the Gulf. Every detail feels intentional — from the na
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Sandy Pants
Sandy Pants
Holmes Beach
$350.00 - $850.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (39)
Welcome to Point's Hideaway!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 home is next to a construction site. There is no set construction schedule, and activity may occur during your stay.The SpaceEvery corner of Point’s H
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Point's Hideaway
Point's Hideaway
Anna Maria Pet Friendly
$350.00 - $900.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.7 (8)
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
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Family Tides - B
Family Tides - B
Bradenton Beach
$280.00 - $920.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4 (1)
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
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On Turtle Time
On Turtle Time
Holmes Beach
$250.00 - $650.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
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
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Coconut Lagoon
Coconut Lagoon
Anna Maria Pet Friendly
$350.00 - $850.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (16)
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
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La Buena Vida
La Buena Vida
Anna Maria Pet Friendly
$380.00 - $890.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (5)
Welcome to AMI Peppertree Paradise!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 AMI Peppertree Paradise — a light-filled beach home where mornings begin with salt air and end beneath the glow of island skies.Just three houses from th
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AMI Peppertree Paradise
AMI Peppertree Paradise
Anna Maria
$360.00 - $850.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (5)
Welcome to Sunsets on Carissa!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.The SpaceEvery corner of this home is designed to bring people together. The open-concept layout connects the kitchen, dining, and living areas, so laughter and conversation flow as
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Sunsets on Carissa
Sunsets on Carissa
Holmes Beach
$300.00 - $770.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (13)
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
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Family Tides - A
Family Tides - A
Bradenton Beach
$280.00 - $920.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Island Time!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals & Property ManagementIsland Time Is A Spacious Coastal Retreat With A Private Lagoon-Style Pool, Tropical Outdoor Living, And A Short Walk To Holmes BeachHighlightsInterior Gourmet Kitchen – Fully equipped with modern appliance
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.Island Time
.Island Time
Holmes Beach Pet Friendly
$225.00 - $720.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (7)
Welcome to A Wave From It All!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 A Wave From It All — a single-level island home crafted for connection and carefree living. Tucked on the quiet north end of Anna Maria Island, this pet-frien
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A Wave From It All
A Wave From It All
Anna Maria Pet Friendly
$360.00 - $850.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (12)
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementThe SpaceYour island escape designed for families and friends to slow down, reconnect, and soak in the simple joys of island life. Nestled near Anna Maria’s most scenic shoreline and moments from Pine Avenue,
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Sol Mate
Sol Mate
Anna Maria Pet Friendly
$360.00 - $850.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (13)

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