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Luxury Beachfront House in Anna Maria!

ANNA MARIA-LOCATED JUST STEPS AWAY FROM THE BEACH AND SHOPPING! This luxury house on the bay features sweeping views of the Bay, Passage Key, Beachfront, and Skyway Bridge. With 4 bedrooms and several entertainment areas this makes an amazing retreat for a family or group of friends that have luxury tastes while enjoying the relaxed atmosphere of Anna Maria. Features include a pool and spa with a putting green and rooftop deck! This is as luxurious as it gets with a short walk to downtown shops

Lido Luxe Estate: Rental with Pool + Rooftop Deck

Lido Luxe Estate by Lido Key Vacations Vacation Rental License #VR25-00081 Minimum stay duration of 7 days/nights Experience unmatched luxury at Lido Luxe Estate, Sarasota's finest island retreat located in the prestigious Lido Key! This beautifully appointed six-bedroom, six and a half bath home offers a perfect combination of elegance, privacy, and entertainment. Located just a short six-minute walk from pristine Gulf beaches and the high-end shops and restaurants of Lido Key’s renowned

Waterfront Home Private pool, elevator and dock

Luxury waterfront retreat w/pool, spa, boat ramp & dock! Elevator makes it perfect for multi‑generational family getaways. This brand-new home features airy open-concept living and 4 bedrooms (3 primary en-suites with King). Swim in the sparkling pool, soak in the spa, grill on the BBQ, and dine under the covered patio. Just minutes to Gulf beaches and local dining. Bring your boat and enjoy waterfront living from your own backyard oasis, where you can relax and watch manatees in the canal.

400ft to Beach, Ocean View, Pool, in the Village

Siesta Key Dream’s largest and most luxurious vacation rental, features four levels, totaling 6-bedrooms, 9-beds, & 6 full-bathrooms. Notable attributes include: a heated-pool, hot tub, 2-balconies, a roof-top sundeck, parking, a backyard and an elevator. With a premier location, beach access point #4 is 400 feet away, and the Siesta Key Village is one block away. In addition to a highly desired location, the unique property design allows beach and Gulf of Mexico views from multiple levels.

NEW Home w/Pool and Putting Green-Gone Gulfin'

Gone Gulfin’ by AMI Locals Welcome to Gone Gulfin’, a brand new, five-bedroom, four and a half bath luxury beach home just one block from the Gulf beaches. Perfect for families and friends seeking a modern island retreat, this stunning home features a private pool and spa, rooftop deck, and fun outdoor games like ping pong and putting green. Designed with relaxation and entertainment in mind, Gone Gulfin’ blends contemporary style and coastal elegance to deliver the ultimate Anna Maria

New Listing! Beachfront! 2 Masters w/Ocean Views!

The Diamond Star on Anna Maria Island, a beautifully remodeled beachfront home originally built by legendary pitcher Warren Spahn. Enjoy spectacular beachfront views, white sandy shores, and unforgettable sunsets. The house features two master suites, a living room, and a kitchen, all offering magnificent ocean views. Enjoy the private decks, direct beach access, beach gear including kayaks, paddleboards, and more. After a day in the sun, relax with a cocktail in the private pool.

Infinity Pool - 2 waterslides - Rooftop Gulf View

Vunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway.

Tripletail | Beachfront | Pool | Hot Tub

Private Beachfront Home - one block from Pine Avenue and the City Pier. Watch dolphins and manatees swim by from your back deck. Bike or rent a golf cart to explore the island and boutique shops and restaurants. Ground floor has a beachfront king bedroom with en-suite bathroom, second king bedroom and bathroom, open floor plan kitchen , dining and family room. Upstairs are two more King bedrooms and bathrooms as well as a sitting area. Heated pool and hot tub

The Shady Mermaid by Duncan Real Estate

Welcome to The Shady Mermaid! A luxury ground-level vacation home just a 3-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen has ample counter space, gas cook top and oven, extra-large fridge/freezer and wine cooler making meal prep a breeze.

Gone Coastal on Elm - Short Walk to beach/Pine Ave

Gone Coastal on Elm – Your Luxe AMI Escape Awaits Welcome to Gone Coastal on Elm, a newly built five-bedroom, seven-bathroom island retreat designed for effortless relaxation and unforgettable memories. Ideally located on Elm Avenue, you’ll be just a short stroll from the soft white-sand Gulf beaches and the charming shops and eateries along Pine Avenue—one of the most coveted spots on Anna Maria Island! Managed by Doreste Properties

7Bedroom Luxury Home W/Private Pool on Siesta Key!

Welcome to Las Palmas! This gorgeous new home on Siesta Key offers luxury around every turn. Stay with up to 16 guests in this 7-bedroom, 7.5-bathroom home, complete with a private pool and spa area, fenced in yard, large full kitchen, dining room, two living spaces with a game room, and much more!

Summer Strand: Resort Like Pool, manatee watching

New luxury vacation property offers the ultimate in resort-like living. Same owners of the successful 5* Amie House. AMI is known for its white sand beaches and crystal clear waters, this barrier island is the perfect destination for those looking to relax and unwind.