Vacation rentals in Anna Maria Island, Florida
Old-Florida charm, no high-rises, walkable.
Neighborhoods in Anna Maria Island
Downtown
Walkable core — restaurants, hotels, nightlife.
Old Town
Historic streets, boutique shops, brick storefronts.
Waterfront
Water views, sunset walks, harbor or riverfront dining.
Arts District
Galleries, murals, indie coffee, late-night venues.
University District
College energy, cheap eats, walkable, lively.
Uptown
Quieter, residential, family-friendly side of town.
Browse by property type
- Cabins in Anna Maria Island
- Beach houses in Anna Maria Island
- Condos in Anna Maria Island
- Villas in Anna Maria Island
- Tiny homes in Anna Maria Island
- Lofts in Anna Maria Island
- Treehouses in Anna Maria Island
- A-frames in Anna Maria Island
- Yurts in Anna Maria Island
- Lakehouses in Anna Maria Island
- Ski chalets in Anna Maria Island
- Mansions in Anna Maria Island
Browse by amenity
- Anna Maria Island stays with hot tub
- Anna Maria Island stays with pool
- Anna Maria Island stays with ev charger
- Anna Maria Island stays with pet-friendly
- Anna Maria Island stays with gigabit wi-fi
- Anna Maria Island stays with dedicated workspace
- Anna Maria Island stays with fireplace
- Anna Maria Island stays with home gym
- Anna Maria Island stays with sauna
- Anna Maria Island stays with kid-friendly
- Anna Maria Island stays with bbq grill
- Anna Maria Island stays with ocean view
- Anna Maria Island stays with mountain view
- Anna Maria Island stays with lake access
- Anna Maria Island stays with ski-in / ski-out
Frequently asked questions
- Are vacation rentals in Anna Maria Island cheaper than hotels?
- Often yes — especially for groups of 3+ or stays of 3+ nights. Per-night rates also drop sharply with weekly and monthly discounts.
- What's the best neighborhood to stay in Anna Maria Island?
- It depends on your trip. We've split Anna Maria Island into neighborhood guides above so you can match vibe to itinerary.
- Do I pay booking fees on StayFlow?
- No. Every stay on StayFlow is direct with the host — you pay the host, not us.
- Can I bring my dog to Anna Maria Island?
- Yes — filter the city by Pet-friendly to see every stay that allows pets.