Play & Stay Vacation Rental Listings
Our Play & Stay listings are carefully selected vacation rentals that pair the comfort of a great place to stay with unforgettable water adventures from Little Philly Sea Adventures. Each home is located near Palma Sola and across Anna Maria Island, including Holmes Beach and Anna Maria, FL, offering easy access to beaches, marinas, and launch points for boat tours and jet ski experiences.
From cozy beach cottages perfect for couples to spacious family-friendly homes ideal for group getaways, our Play & Stay listings are designed for convenience and relaxation. Guests enjoy comfortable accommodations, prime locations, and the option to bundle their stay with on-the-water experiences like boat tours, jet ski adventures, and private outings.
Whether you’re planning a weekend escape or an extended Gulf Coast vacation, our Play & Stay listings make it easy to stay close to the action and spend more time enjoying the water. Book a home you’ll love, add unforgettable experiences, and enjoy a seamless vacation from check-in to your last day on the coast.
historic cottage, perfect for 2. Longboat Key, FL
2 bedrooms • 2 baths • Cottages
Discover the Beauty of Holmes Beach & Anna Maria Island by Boat or Jet Ski
Transparent pricing, easy check-in, and a smooth return process. Choose your experience below.
Pontoon Boat Rentals
Anna Maria Island, FL
Apacious, comfortable pontoons for sandbars, family days. Perfect for groups who want to relax and explore.
4 hours
$395.00
6 hours
$445.00
8 hours
$495.00
Jet Ski Rentals
Palma Sola, FL
High-energy fun with clear rules and quick check-in. Great for couples, friends, and adventurous families.
1 hours
$120.00
2 hours
$220.00
4 hours
$390.00
Boat Tours
Anna Maria Island, FL
Want to enjoy the water without driving? Book a captained tour for dolphins, sandbars, sunsets, and local island cruising.
2HR: Dolphin & Donuts Boat tour
$65.00 PP
4HR: island hopping tour
$500.00
2HR: Sunset Tour
$65.00 PP
Jet Ski Tours
Palma Sola, FL
A guided route with a real plan — scenic stops, local knowledge, and an experience you won’t get from a standard rental.













