Luxury Vacation Home Rentals on Anna Maria Island

Discover our Anna Maria Island vacation rentals with private pools, perfect for relaxing getaways with family, friends, or pets. From Anna Maria to Holmes Beach, Bradenton Beach, & right Off Island, our homes offer privacy, comfort, and easy access to the island’s best beaches, shops, and restaurants.

Our local team is here to ensure a seamless stay, offering personalized support and insider tips to make your vacation unforgettable. Whether you’re bringing your pup  or planning a family retreat, you’ll find the ideal home for your island escape.

Properties Available 41 properties available
Welcome to Kokomo!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 SpaceDiscover Kokomo, where comfort meets calm in a thoughtfully updated beach cottage just a short walk from the Gulf of Mexico. Designed for rest and reconnection, this home
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Kokomo
Kokomo
Holmes Beach
$205.70 - $805.20 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (12)
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
$195.00 - $780.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (11)
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
$315.90 - $1,010.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (14)
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
$299.70 - $1,039.50 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.7 (8)
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
$518.40 - $2,300.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (13)
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
$323.19 - $1,128.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (14)
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
$218.16 - $831.60 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (15)
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 - $1,900.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (4)
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
$331.98 - $1,100.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (8)
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
$338.58 - $1,214.40 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (21)
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
$338.58 - $1,029.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (15)
Welcome to Sunset Margarita!Bradenton, Florida (Just off Anna Maria Island, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.The SpaceSet within Margaritaville’s One Particular Harbour waterfront community, Sunset Margarita blends modern finishes with easy, resort-style living. This third-f
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Sunset Margarita
Sunset Margarita
Off Island Pet Friendly
$189.00 - $525.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (3)

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When is the best time to visit Anna Maria Island?

Anna Maria Island is beautiful any time of year, but different seasons are best for different activities. Spring and fall both have warm temperatures and fewer crowds, and are perfect for a more relaxed vacation spent enjoying the outdoors and checking out local attractions. Summer is the hottest and busiest time of year. If you’re looking for exciting summer energy, summer is your best bet. Winter in Anna Maria Island has cooler temperatures and the lowest prices.

Are dogs allowed on the beaches in Anna Maria Island?

Most of the beaches on Anna Maria Island do not allow dogs, so it’s important to check the regulations before bringing your pup. But even if you can’t bring your four-legged family member to one of the main beaches, there are plenty of alternatives, like Palma Sola Causeway Park & Bayfront Park. View Pet Friendly Rentals in Anna Maria Island.

What are the best beaches on Anna Maria Island?

Every beach on the island is fantastic! We love Bean Point, on the northern tip of the island, for its views, wildlife viewing, and spectacular shelling. Bradenton Beach is great for anyone looking for a mix of relaxation and activities, with easy access to biking trails and restaurants. And Holmes Beach is lovely for anyone who wants to swim in clear waters or relax in the sugar-soft sands the island is famous for. Rentals within walking distance to the beach

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