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.

Modern patio with turquoise pool, lounge chairs, and indoor-outdoor living area; small inset room photos.

Manatee Manor in

Bradenton, FL

4 Bedrooms • 2 Baths

Small white house with a gabled roof and front windows beside a narrow lit side structure.

seasonal vacation rental on anna maria, FL

2 Bedroom • 2 Bath

White house porch with teal chairs, a light blue door, and potted plants under trees

Home in bradenton intercostal water front

2 Bedrooms • 2 Bath

Screened-in backyard pool and hot tub at sunset with blue water and lounge chairs

Sunshine RetreaT
Bradenton, FL

4 Bedrooms • 2 Baths • 10 Guest • Pets Ok

Sunlit balcony with white wicker seating, turquoise rug, and view of trees and water

Entire condo in
Bradenton, Fl

4 guests • 2 bedrooms• 2 beds• 2 baths

Palm trees and a hammock beside a sunny lakeside yard with grass and a patio.

Entire townhouse in Bradenton, Fl

8 guests • 3 bedrooms • 4 beds • 2 baths

Front porch of a white house with palm trees, a stone path, and potted plants.

historic cottage, perfect for 2. Longboat Key, FL

2 bedrooms • 2 baths • Cottages

Coastal house with white siding, palm trees, and a landscaped front yard beside a walkway

Entire home in Holmes Beach, Florida

6 guests • 3 bedrooms • 3 beds • 2.5 baths

Bright sunroom with white chairs, blue rug, and glass table overlooking a lake

Entire home in Anna Maria, Florida

6 guests • 2 bedrooms • 2 beds • 2 baths

Wooden dock with string lights, overlooking calm water, with turquoise chairs at sunset.

Entire home in Anna Maria, Florida

8 guests • 3 bedrooms • 4 beds • 2 baths

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 on clear water with a black canopy, viewed from low angle

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
Start at: $400.00
6 hours
Start at: $490.00
8 hours
Start at: $575.00
Person riding a green and white jet ski on calm blue water near a tree-lined shore

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
$135.00
2 hours
$230.00
4 hours
$400.00
Two people riding a blue-and-white jet ski on calm turquoise water under a pale sky

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.

2 hours
$350.00
3 hours
$450.00
Custom Hours
Call for details