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.

Escape to a charming 3-bedroom vacation home on Anna Maria Island, where comfort meets coastal elegance. Perfect for families or small groups, these beautifully appointed homes offer modern amenities, open living spaces, and exceptional outdoor areas. Just steps away from the island's pristine beaches, you'll enjoy easy access to local dining, boutique shopping, and outdoor activities like biking, kayaking, and fishing. Relax in your own tropical oasis and create lasting memories on Anna Maria Island with Once Upon A Beach’s exceptional 3-bedroom vacation rentals.

We also offer 2 Bedroom4 Bedroom, and 5+ Bedroom vacation rentals, perfect for any size getaway!


Properties Available 14 properties available
Welcome to Anna Maria Aloha!On Anna Maria Island (Anna Maria, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and co
Hot HOT 27
Anna Maria Aloha
Anna Maria Pet Friendly
$240.00 - $680.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (9)
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.Discover the ultimate in luxury island living at Sea La Vie, a custom-built retreat located on the desirable north end of Anna Maria Island. With 2,933 sq. ft. of elegant living space
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Sea La Vie
Anna Maria
$540.00 - $1,950.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Welcome to Griffins Island Getaway!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Coastal Luxury with a Private Heated Pool, Game Room, and Short Walk to the Beach, EV ChargerHIGHLIGHTS: Spacious & Open Layout: Bright and airy living, dining, and
Hot HOT 46
Griffins Island Getaway
Holmes Beach Pet Friendly
$320.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementBright and Beautifully Updated 3-Bedroom Home with Heated Pool & Spa, Walking Distance to Bean Point Beaches and Pine AvenueHIGHLIGHTS: 1,500 Square Feet: Fresh, modern comfort designed for relaxation. Sle
Hot HOT 29
Sol Mate
Anna Maria Pet Friendly
$330.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (10)
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.La Buena Vida is a luxurious 3-bedroom waterfront home on Anna Maria Island, featuring a heated pool, spa, private dock, and easy access to bayside and Gulf beaches, plus shops and
Your Vacation Story: Your Vacation Story:
Your Vacation Story:
La Buena Vida offers the ultimate Anna Maria Island escape, just a short walk to bayside beaches, Bean Point, and Pine Avenue’s charming shops and dining. Whether you seek relaxation or adventure, this coastal retreat is your perfect getaway!
La Buena Vida
Anna Maria Pet Friendly
$380.00 - $880.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
Welcome to Blue Haven Beach House!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover island charm and modern comforts at Blue Haven Beach House, an elevated coastal retreat steps from the white sands of the Gulf beaches in Holmes Beach.HIGHLIGHT
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Blue Haven Beach House
Holmes Beach Pet Friendly
$300.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (11)
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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comfortabl
Hot HOT 31
Sandy Pants
Holmes Beach
$355.00 - $785.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (36)
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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—with updated pictures as of Februa
Hot HOT 51
Coconut Lagoon
Anna Maria Pet Friendly
$320.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comfo
Hot HOT 46
A Wave From It All
Anna Maria Pet Friendly
$335.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (9)
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.Enjoy a sun-soaked getaway at AMI Peppertree Paradise, where comfort, convenience, and island charm come together for the perfect Anna Maria Island vacation rental!1970 s
Hot HOT 30
AMI Peppertree Paradise
Anna Maria
$335.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (2)
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.A Stunning Beachside Escape with a Private Heated Pool, Game Room, and Gulf BreezesHIGHLIGHTS: Open Layout: Bright and airy kitchen, dining, and living area with a large TV, per
Hot HOT 52
Sunsets on Carissa
Holmes Beach
$350.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (9)
Welcome to Family Tides – Unit B!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides B*Family Tides – Unit B is a bright and spacious second-floor condo that offers 3 bedrooms, 2 bathrooms, and access to shared outdoor amenities, including a he
Your Vacation Story: Your Vacation Story:
Your Vacation Story:
Enjoy modern comfort and coastal charm in this bright, open retreat. Gather in the inviting living space, relax by the heated pool, or take in stunning views from the shared rooftop deck.
Family Tides - B
Bradenton Beach
$285.00 - $850.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4 (1)

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