Three New Anna Maria Island Vacation Rentals
June 29, 2026
3 New Anna Maria Island Vacation Rentals
Anna Maria Island Accommodations just welcomed three new homes, scattered across Anna Maria City and Holmes Beach. Each one has that easy, nostalgic island feel Anna Maria Island Accommodations guests keep coming back for, beach cottages, slow mornings, and a short walk to the Gulf. Whether it’s a sunset stroll on Anna Maria City Beach or a quiet afternoon paddling a Holmes Beach canal, the appeal here has never been about flash, it’s about feeling like you found your spot. Every home below books fastest, and cheapest, straight through Anna Maria Island Accommodations.
Sunshine Daydream
Quick look: 3 BR / 2.5 BA · Holmes Beach, North Beach Village · Community pool
Tucked into Holmes Beach’s North Beach Village, Sunshine Daydream lives up to its name. Three bedrooms and two and a half baths, a community pool, a screened lanai, and a third-floor primary suite made for slow mornings with coffee in hand. Grab dinner at The Ugly Grouper or hop the free trolley to Holmes Beach Towne Center.
Book Sunshine Daydream direct →
Chardonnay Shores
Quick look: 3 BR / 2 BA · Anna Maria City · Steps to Pine Avenue
Right in the heart of Anna Maria City, Chardonnay Shores is a refreshed three-bedroom, two-bath retreat just a short stroll from Anna Maria City Beach and the shops and restaurants lining Pine Avenue. A classic island week, starting point included.
Book Chardonnay Shores direct →
Delphina
Quick look: 2 BR / 2 BA · Holmes Beach canal · Waterfront villa
Delphina sits on a quiet canal in Holmes Beach, a two-bedroom, two-bath waterfront villa built for slower mornings, easy kayak access, and a quick trip to either the bay side or the beach.
Book Direct, Always
All three homes are open for booking now, and everything costs less when you book direct with Anna Maria Island Accommodations, no third party fees, just the island rate and a team that’s been doing this for years. Pack your flip flops and start planning the rest of the trip.