Anna Maria Island Vacation Rentals with Private Pool

Our collection of Anna Maria Island vacation rentals with private pools offers the perfect blend of relaxation and elevated coastal living. Whether you're spending the day at the beach or enjoying a quiet afternoon poolside, these homes provide a seamless indoor-outdoor experience designed for comfort and ease.

From sun-soaked lounging to evening swims under the stars, each home is thoughtfully curated to deliver a private, resort-style stay in one of Florida’s most sought-after island destinations.

For details on heating, operation, and what to expect during cooler weather, please review our Pool Information guide.

Properties Available 32 properties available
Welcome to The Palm at Bean Point!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation RentalsWhere modern luxury meets laid-back island living, just moments from Bean Point.Tucked away in one of Anna Maria Island's most beloved neighborhoods, this beautifully renovated coastal retreat offers everything you need for a rela
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The Palm at Bean Point
The Palm at Bean Point
Anna Maria
$357.00 - $1,100.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
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.The SpaceStep inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmos
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The Cottage on Pine
The Cottage on Pine
Anna Maria Pet Friendly
$225.00 - $903.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (13)
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
$351.00 - $1,010.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (13)
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
$540.00 - $2,520.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (18)
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
$346.50 - $1,029.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (18)
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.Tucked along a quiet stretch on the north end of Anna Maria Island, this home blends easy island living with space to gather, unwind, and enjoy the water. Fresh paint, u
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Hangin on Hammock
Hangin on Hammock
Anna Maria Pet Friendly
$342.00 - $1,100.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (2)
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
$225.00 - $818.40 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (5)
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.Experience Catching Waves — where laid-back island living meets everyday adventure. Just a short stroll to the white-sand beaches of Holmes Beach, this ground-level h
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Catching Waves
Catching Waves
Holmes Beach Pet Friendly
$225.00 - $778.80 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)
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
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Mariner's Crossing
Mariner's Crossing
Bradenton Beach
$720.00 - $3,300.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.9 (15)
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
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Ocean Sunrise
Ocean Sunrise
Bradenton Beach
$630.00 - $2,450.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 20 guests
Rating 5 (2)
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
$720.00 - $2,478.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (2)
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.The SpaceYour serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenie
Hot HOT 22
Fins Up
Fins Up
Holmes Beach
$270.00 - $831.60 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (15)

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