Indulge in the ultimate getaway by diving into our handpicked selection of top-rated Anna Maria Island vacation rentals with pools. These hidden gems offer not only a refreshing oasis to beat the Florida heat but also a gateway to Anna Maria Island beaches and an array of unique experiences that will leave you breathless. And for the dog lovers out there, there’s even a long list of Anna Maria Island pet-friendly rentals to explore.

Spend your days strolling along the pristine white sand beaches, where the Gulf of Mexico’s turquoise waters beckon you to take a dip. For the adventurous souls, paddleboarding through the mangrove tunnels of Robinson Preserve or embarking on a thrilling jet ski excursion around the island’s shimmering coastline is sure to ignite your sense of adventure. And if you prefer a leisurely pace, explore the charming streets of the island’s historic districts, lined with vibrant art galleries, boutique shops, and delectable seafood restaurants.

Bay Breeze: Vacation Home With Private Pool and Private Beach

Experience the ultimate beach vacation with Bay Breeze on Anna Maria Island. This luxurious, Key West-style home offers breathtaking views of the ocean, a private beach, and plenty of outdoor fun such as kayaks, a ping pong table, and a private pool. Inside, relax in the expansive living and dining rooms, or luxurious kitchen with wine refrigerator and Nespresso machine, and enjoy the music from the easily programmed iPad.

With four en suite bedrooms — each with king or twin beds and walk-in closets — every guest will feel pampered. Spend the day fishing, swimming, and playing along the shoreline, or simply lounging on the terrace with a spectacular view of the illuminated Sunshine Skyway Bridge and the lights of St. Petersburg.

Family-Friendly Vacation Rental Steps From the Beach

This luxurious vacation rental is the perfect destination for your next escape to Anna Maria Island. Enjoy the quiet, laid-back ambiance of the north end of the island just steps to the gorgeous bayside beach and a five-minute walk to the world-renowned Bean Point. There’s plenty of room for everyone with a heated saltwater pool, an outdoor media area, a grill, and lawn games for a fun-filled vacation.

The spacious open floor plan provides plenty of natural light and stunning views of the bay. The gourmet kitchen is fully stocked for all of your cooking needs, and guests will appreciate the cozy gas fireplace in the dining room. With two master suites, two additional bedrooms, and a half bath, everyone will have their own space. Plus, your stay includes access to bikes and a six-person golf cart, so you can explore the island like a local.

Bayside Vacation Home With Rooftop Terrace & Outdoor Pool

With its elevated luxurious coastal design, vaulted ceilings, accent walls, and exquisite flooring throughout, Marina Magic offers a unique and breathtaking experience. Relax and unwind in the heated pool and spa set in a beautifully landscaped garden, then enjoy the spectacular panoramic views of the bay from the rooftop deck as the sun sets. With its convenient location, you are just steps away from accessing the calm waters of Tampa Bay, biking to Bayfront Park Beach and Bean Point Beach, and enjoying delicious meals from the nearby waterfront restaurant.

Enjoy a gourmet kitchen with top-of-the-line appliances, a large and comfortable sectional sofa, and custom built-ins next to a gas fireplace. When night falls, relax in the hot tub under the stars with a glass of wine before retreating to the spacious master suite with its designated work space and stunning ensuite bathroom.

Luxe Island Escape: Huge Heated Pool & Spa With Swim-Up Bar

Come and escape to Luxe Island Escape for the perfect island getaway! This brand-new custom-built luxury vacation home is located in Anna Maria Island’s prestigious North End. With four bedrooms and four and a half bathrooms, this next-level tropical retreat can accommodate up to eight guests comfortably.

Indulge your senses in the huge heated pool and spa, swim-up bar, rooftop deck with sweeping water views, and so much more. Plus, it’s only steps away from the Rod and Reel Pier and a few blocks from beautiful Bean Point Beach, so you can soak up the sun any way you please. Luxe Island Escape is sure to be the perfect destination for your next family vacation. Book your stay today and experience the ultimate in island living.

Fine and Sandy: Beach-Chic Villa With Resort-Like Amenities

Fine and Sandy is the perfect place for travelers seeking a beach-chic paradise. Enjoy panoramic rooftop views, a private pool with a spa, comfortable and modern furnishings, and a putting green for a luxurious island escape. This seven-bedroom, seven-bathroom home offers something for everyone, from a gourmet kitchen with everything you need to a short walk away from the beach.

Find solace in the tranquil ambiance of all the rooms and the natural glow of sunlight through the floor-to-ceiling glass sliders. Fine and Sandy is just a short bike ride or leisurely walk to the historic Anna Maria Island City Pier for a day of indulging in beautiful scenery. Don’t forget to explore the cafes, upscale boutiques, and gourmet restaurants that are dotted along Pine Ave. Make Fine and Sandy your next island retreat for a memorable experience!

Dive Into Pure Bliss With These Anna Maria Island Rental Properties

Pack your swimsuit, grab your sunscreen, and get ready to embark on an unforgettable journey to this idyllic island, which has been ranked as one of the most affordable snowbird destinations in the U.S. With its stunning beaches, unique activities, and inviting rentals, Anna Maria Island guarantees a getaway filled with cherished memories and pure bliss.