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 Sunset at 714!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementThe SpaceWhere island sunsets, beach days, and family memories come together.Tucked away on the highly desirable north end of Anna Maria Island, Sunset at 714 places you just a short stroll from the sugar-whit
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Sunset at 714
Sunset at 714
Anna Maria
$369.00 - $1,900.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
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
$315.00 - $1,042.80 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (41)
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
$640.00 - $2,782.50 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (11)
Welcome to Hidden Palms!On Anna Maria Island in Holmes Beach, FloridaManaged by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency. Perfect for: Families, couples, and small groups looking for a comfortable island home with privacy, flexible gathering spaces, and convenient access to the beach.Highligh
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Hidden Palms
Hidden Palms
Holmes Beach
$270.00 - $871.20 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Sea La Vie!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 light dances across the water and modern design meets island ease, Sea La Vie invites you to experience the beauty of Anna Maria Island from a space that feels both lux
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Sea La Vie
Sea La Vie
Anna Maria
$413.10 - $1,942.50 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 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
$800.00 - $3,300.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.9 (15)
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 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
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Fins Up
Fins Up
Holmes Beach
$243.00 - $831.60 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (15)
Welcome to Vela Mar!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 SpaceVela Mar is where elevated coastal living meets modern luxury innovation. Designed with intention and inspired by the sophistication of Miami-style smart living, this fully i
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Vela Mar
Vela Mar
Holmes Beach Pet Friendly
$333.00 - $1,386.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
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
$750.00 - $2,450.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 20 guests
Rating 5 (2)
Welcome to Cozy Cabana East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover Cozy Cabana East, where comfort, care, and connection come together in a thoughtfully designed, single-level home just a short walk from the beach. Blending
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Cozy Cabana East
Cozy Cabana East
Holmes Beach Pet Friendly
$210.60 - $805.20 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (11)
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
$329.67 - $1,029.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (18)

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