Play & Stay Vacation Rentals in Anna Maria Island, Holmes Beach & Bradenton Beach

Our Play & Stay experience combines premium Airbnb vacation rentals with unforgettable water adventures. Stay in beautiful local homes while enjoying exclusive access to boat rentals, jet ski rides, fishing charters, and dolphin tours — all designed to make your trip to Anna Maria Island stress-free and memorable.

Outdoor patio at night with wicker furniture, a fire pit, potted plants, a wooden fence with lights, tall palm trees, and a gravel pathway.

Backyard with a swimming pool, green lawn chairs, a picnic table, and outdoor seating area shaded by a large sail, surrounded by a wooden fence and trees.

Curated vacation rentals and Airbnb listings in Anna Maria Island, Holmes Beach & Bradenton Beach

Add-on boat rentals & jet ski rentals for the ultimate waterfront adventure

Book fishing charters, dolphin tours & sandbar trips right from your doorstep

Enjoy local expertise and concierge-style service for stress-free stays

Close to beaches, waterfront dining, and the Gulf Coast’s top attractions

Play & Stay – Vacation Rentals & Airbnb Stays on Anna Maria Island

Discover the perfect mix of comfort and adventure with Play & Stay vacation rentals and Airbnb homes in Anna Maria Island, Holmes Beach, and Bradenton Beach. Our curated properties put you steps from the sand and just minutes from the Gulf Coast’s top attractions. Pair your stay with our boat rentals, jet ski rentals, fishing charters, and dolphin tours for an unforgettable getaway. Whether it’s a family vacation, a romantic escape, or a group adventure, Play & Stay makes it easy to relax, explore, and enjoy more of Florida’s beautiful coastline.

Outdoor backyard setting with a swimming pool decorated with white floating balls. A long dining table covered with a white tablecloth and set with plates, glasses, and floral centerpieces. Several chairs around the table and umbrellas providing shade. In the background, there are trees, palm trees, and a white house with black shutters. It appears to be prepared for a gathering or celebration.

Entire home in Bradenton, Florida

10 Guest • 4 Bedrooms • 9 Beds • 3.5 Baths

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Partner With Little Philly Sea Adventures – Let’s Play & Stay Together!

Are you an Airbnb host in Anna Maria Island, Holmes Beach, or Bradenton Beach?
Team up with Little Philly Sea Adventures and give your guests the ultimate experience — vacation rentals + adventure on the water!