Holiday rentals with a hot tub near Bean Point Beach

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

Maritime Memories by Duncan Real Estate

Welcome to the newly renovated and updated Maritime Memories! This north-end 3 bedroom plus den, 2 bath pool home is waiting for you to enjoy your next vacation on Anna Maria Island. Maritime Memories is an eclectic island home with plenty of room for a large family, two living areas plus den so the house comfortably sleeps 8 people. Relax by the pool and enjoy the privacy of a tropical landscaped yard. It is also a close walk to the beaches on the north-end of Anna Maria. HIGHLIGHTS

Swim. Soak. Play. | Beaches | 5mi 2 IMG | Dine

Welcome to Villa Delfino—where summer days are filled with sunshine, beach adventures, and island exploration. When evening arrives, the villa transforms into a relaxing oasis with ambient lighting, outdoor gathering spaces, and the perfect atmosphere for creating lasting memories. Experience white-glove hospitality with a responsive local team, hands-on management, and detailed pre-arrival inspections. We're available throughout your stay to ensure a seamless, stress-free vacation.

Beach House w/Private Pool & Spa

Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the beautiful beach is right by the house. This 3 bedroom 2 bathroom home is situated on a corner lot on a quiet street and is located just steps to the beaches of the Gulf of Mexico. Enjoy the private pool and spa, surrounded by tropical landscaping. Tons of beach gear included! It is located in a great area to explore by bike, ride to Pine Ave., Bayfront Park, the City Pier, etc....

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.

Ocean Air Oasis-New Centrally Located AMI Luxury

Immerse yourself in coastal luxury at this exceptional 3-bedroom, 2.5-bathroom custom home, where opulent high-end finishes and stunning pecky cypress floors adorn every nook. Revel in the impeccable features, including Sub-Zero and Wolf appliances, marble countertops, Shaw’s sinks, and exquisite custom woodworking, all bathed in abundant natural light. This delightful space offers panoramic views of the lavish backyard, complete with a heated pool and spa.

Private pool, only two blocks .3 miles from beach!

Just two blocks away from the beautiful white sands of Holmes Beach. Restaurants & night life even closer. Swimming pool and spa are inviting for both romantic getaways as well as families. You will have access to the entire beautiful two story townhouse. The property has a shared wall, but all space is private and quiet. The outdoors are separated and private as well. Plenty of parking, sun, & fun. New mattresses, new couch, and other furniture.

New Luxury 3/3 Condo in Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features wonderful unobstructed water views of Anna Maria Sound and Tampa Bay. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

Lux Getaway: Pool| Hot Tub| Bocce Ball nr AMI &IMG

Welcome to Bayside Bungalow – Your Gateway to Fun and Relaxation! Experience Bradenton, Florida, like never before at this stunning, brand-new 2,600 sq. ft. retreat. Perfectly designed for families and friends, this spacious 5-bedroom, 3-bathroom home comfortably accommodates up to 13 guests – including a versatile walk-through bedroom for added flexibility. Book Your Stay Today So You Can Relax In the Sunshine Tomorrow! 🥳

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Gulf Views | Heated Pool | Elevator, 1min to Beach

Gulf views, heated saltwater pool & spa, elevator, rooftop deck and beach access less than a 1-minute walk away! Shore to Please is an updated 5BR home on sought-after N Shore Drive. Relax under the palms by your private pool, play backyard mini golf, or enjoy incredible sunsets from the rooftop deck. Walk or bike to Pine Ave's shops and restaurants or hop on the free AMI trolley to explore the island!

Paradise Pointe by Beach Boutique Rentals

*Features include* * Canal front with private dock * 3 bedrooms, 2 full bathrooms plus den * Master bedroom with ensuite bath * Private saltwater pool and spa * Indoor and outdoor dining * Laundry room and office space * Basketball pool game * Sun loungers * Gas grill * Beach chairs, umbrella and cart * Walk to Bean Point