Anna Maria Island, Florida
367 properties available
Welcome to Island Time – Your Coastal Retreat in Bradenton Beach!Wake up to the gentle sway of palms and end your days with sunset views over the bay. Nestled within the sought-after Bradenton Beach Club community, this spacious coastal townhome offers a private, peaceful escape just moments from the shoreline.Property Highlights:- Sleeps up to 8 g
Sunrise Garden #3
Welcome back to your favorite island getaway—now better than ever! This beautifully remodeled top unit in Anna Maria offers the same soothing ocean breeze and peaceful charm you love, with fresh new furnishings and thoughtful upgrades to elevate your stay.
Inside: fully equipped kitchen (no dishwasher), dining space, living area
Walk to the beach or laze by the backyard pool! Or jump on the free island trolley and see the sights.Welcome to your Holmes Beach getaway on Anna Maria Island. This well-located 1/2 duplex is set up for families, couples, and friends who want an easy, laid-back beach trip with everything close by.The spaceThis home features 2 bedrooms and 2 bathro
🏖️ Dolphin Resort – Poolside Fun & Beach Bliss on Holmes Beach 🌴💖 Why You'll Love Dolphin Resort Welcome to Dolphin Resort, your private island retreat where beach days roll into relaxing evenings around your own tropical tiki bar. Just four houses from the white sands of Holmes Beach, this 3-bedroom, 2.5-bath getaway pairs laid-back coastal liv
Safari Suite
Enjoy an incredible beach vacation at this safari-themed rental with designer decor throughout and a well-appointed Key West-style patio. Feel the warm sea breeze off the Gulf of Mexico and listen as the waves roll across the sugar soft sands at the neighboring beach, directly across the street.
Take a trip on the island's free trol
5608 GULF DR UNIT 111 SUN PLAZA WEST, HOLMES BEACH, FL 34217VRC19-000241Book with confidence: NO CANCELATION FEES Cancellation Policy (Effective for reservations made on or after August 13, 2025) $500 deposit due at time of booking; balance due 60 days prior to arrival Cancel 60+ days before arrival → Full refund (no fees). Cancel within 60 days
Tradewinds Cottage #14 - Bradenton Beach Rambo's Beach Retreat! Welcome to "Rambo's Beach Retreat" located in the popular community of Tradewinds on Beautiful Bradenton Beach, Florida. This completely renovated (2024) and professionally decorated beach cottage is perfect for those looking for a relaxing island retreat just steps away from the sugar
110 11th Street South - Bradenton Beach - FL 34217No cancellation fees!Cancel 60+ days before arrival → Full refundCancel within 60 days → No refundExtended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable$500 deposit due at booking; balance due 60 days priorThird-party travel insurance through Beach Retreats is non-refundable
── ✨ HIGHLIGHTS ✨──🏖️ Private Beach Access – Deeded entry just across the street🌊 Largest Heated Saltwater Pool on Anna Maria Island💻 500Mbps High-Speed Dedicated WiFi🧺 In-Unit Laundry📺 Smart TVs in Every Room🌴 Private Bayside Terrace with Peaceful Bay Views── ✨ AMENITIES ✨ ──🏓 Pickleball, Tennis, Bocce Ball & Shuffleboard Courts💪 Modern Fi
Welcome to The 19th Hole: Your Perfect Anna Maria Island Vacation RentalExperience the best of Anna Maria Island at The 19th Hole, a stunning Anna Maria beach house nestled just a short stroll from both the bay beaches and the Gulf of Mexico. Located near Pine Avenue, this family-friendly home is the ideal getaway for those looking to explore the c
Manatee Lookout is a charming 3 bedroom/3 bath home with a private heated pool located on the sought after north end of Anna Maria Island. This home has everything you need for the perfect vacation and is only a short walk to the white sandy beaches. Upon entry, you have the living room where you can relax and read to book or watch TV after a long
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