Holiday rentals with a hot tub in Anna Maria

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Beautiful Beach house! Heated pool and spa!

Discover your dream getaway at this beautifully decorated vacation rental in Anna Maria Island. This stunning 4-bedroom, 4.5-bathroom home offers luxury and comfort, featuring a spacious open-concept living area, modern kitchen, and elegant furnishings. Enjoy the private pool and hot tub, and the beach is just a 5-minute walk away. The highlight is the rooftop deck, where you can soak in breathtaking sunsets. Experience the perfect blend of style and convenience for your unforgettable vacation!

Sea 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.

Hammock in the Sun by Duncan Real Estate

Welcome to Hammock in the Sun!This North end home offers a prime location just steps from Pine Avenue. Indulge in delightful lunches at the nearby restaurants and explore the boutiques only a short stroll away.This two-story home features a large living room, dining area and plenty of outdoor seating. Take the stairs up to the first-floor main level with a spacious open floor plan that features the living and dining area with a screened in balcony located off the dining area with table and ...

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Hidden Haven / Private Pool & Hot Tub

Your dream bayside escape at this charming single-story haven, just a heartbeat away from the pristine shores of Anna Maria Island. Featuring 4 inviting bedrooms and 2 stylish baths, indulge in the luxury of a private pool nestled among vibrant tropical foliage. Sip your morning coffee or toast to sunset cocktails poolside, wander to the sparkling Gulf, discover the delightful shops and eateries in Holmes Beach. This oasis is perfect for sun-kissed relaxation and exciting island escapades!

Heated Pool, Hot Tub, Game Room, Steps to Beach!

Welcome to Island Dreams, the ultimate peaceful escape just 4 min walk from Anna Maria Island's stunning beaches. This fully renovated three-bedroom, three-bath beach house features a Zen-inspired backyard oasis, a private cocktail pool, and a game room! Walk to shops, restaurants, and the trolley stop! Island Dreams offers the perfect blend of relaxation, location, and indoor and outdoor fun! NOTE: Holmes Beach has a 7-day rental minimum. Check in / Check out days are on Saturdays.

Beachfront • Steps to Sand • Sunset View • Balcony

Just 14 steps from your second-floor beachfront condo, you’re on the powder-soft sands of Anna Maria Island. The bedroom has a plush queen bed, and the living room offers a queen sleeper sofa. Enjoy a full kitchen, cable TV, high-speed Wi-Fi, shared laundry downstairs, and one assigned parking space. Relax on your balcony with sweeping Gulf views and unforgettable sunsets. Perfect for couples or families, this is a true beachfront retreat with sand and sea at your doorstep.

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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....

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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.

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. 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.

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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.

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Waterfront Pool Home Steps to Beach

Escape to our waterfront oasis on Anna Maria Island! This bright, updated home features a private heated pool, hot tub, and dock. Perfect for families, it's just a 5-minute walk to the world-renowned Gulf beaches. Enjoy stunning sunrises, a dedicated workspace, and modern coastal decor. Explore the island with ease via the free trolley. Your perfect getaway awaits!