Duncan Real Estate offers a premier selection of Anna Maria Island vacation rentals featuring private pools, ranging from intimate one-bedroom villas to spacious four-bedroom family estates. These properties provide a private oasis for travelers who want the convenience of a refreshing swim just steps from their door, combined with close proximity to the Gulf of Mexico beaches.
Why choose a rental with a private pool on Anna Maria Island?
Choosing a rental with a private pool provides a “home away from home” experience with added luxury and privacy.
Safety & Privacy: Ideal for families with children or couples seeking a secluded romantic getaway.
Convenience: Switch between the beach and a private swim in seconds.
Flexibility: Perfect for poolside BBQs, cooling off from the Florida sun, or a quiet evening soak.
Top Anna Maria Island Vacation Rentals with Private Pools

1 Step Closer
This rental is located in a secluded tropical setting, offering a quiet retreat that is still only a short walk from the beach.
Best For: Travelers seeking tranquility and privacy near the coast.
Key Features: Private pool with lounge seating, tastefully furnished interior, and lush landscaping.
The Beach House
The Beach House is a high-end beachfront property designed for luxury living.
Highlights: Mesmerizing pool area with an outdoor spa and panoramic views of the Gulf of Mexico.
Layout: 3 bedrooms, 2.5 bathrooms.


Our Great Escape
A spacious four-bedroom estate that serves as a private sanctuary for larger groups.
Highlights: Crystal-clear private pool surrounded by tropical foliage, well-equipped kitchen, and additional loft space.
Layout: 4 bedrooms, 4.5 bathrooms.
The Shady Mermaid
A beachfront “hidden gem” that offers immediate access to the sand and water.
Best For: Guests who want a seamless transition between the pool and the Gulf.
Key Features: Expansive pool area, BBQ setup, and ocean views from every angle.


Bodacious Oasis
Located one block from the beach, this home blends vintage charm with modern amenities.
Highlights: Original hardwood floors and a secluded pool area nestled in thick foliage.
Layout: 3 bedrooms, 2.5 bathrooms.
The Villas 2A
Situated in peaceful Bradenton Beach, this unit offers a sophisticated atmosphere for smaller groups.
Best For: Romantic getaways or solo travelers.
Layout: 1 bedroom, 1 bathroom.
Highlights: Heated private pool and direct beach access.


Manatee Manor
A spacious and functional choice for families.
Highlights: 2 bedrooms, 2 bathrooms, and a private pool deck surrounded by greenery.
Capacity: Sleeps up to 6 guests.
Plan Your Visit
Whether you’re seeking relaxation, adventure, or a little bit of both, Duncan Real Estate is here to make your dreams a reality. Contact us today to start planning your unforgettable vacation and discover the true essence of island living on Anna Maria Island!
How do I book a pool home on Anna Maria Island?
You can browse all available properties and book directly through the Duncan Real Estate website. Booking direct ensures you receive the best rate and personalized service from local experts.







