Luxury rentals in Anna Maria

Experience Luxury at Go with the Flow! Lazy River

Go with the Flow by Exclusive Vacations Vacation Rental License #VR24-000026 Welcome to Go with the Flow, an exceptional three-level luxury retreat offering five bedrooms and five and a half bathrooms, thoughtfully designed for an elevated Anna Maria Island getaway. Located just a short five-minute stroll to Anna Maria Beach, this newly built vacation home showcases a private pool with spa, a rooftop entertainment deck, and beautifully curated designer interiors. Whether gathering with family

Coastal Elegance! Pool, Putting Green, Movie

Periwinkle Place by Exclusive Vacations VR25-000004 Indulge in the ultimate luxury beach home at Periwinkle Place, part of our Exclusive Collection. This stunning estate in the heart of Anna Maria offers six spacious bedrooms and six and a half bathrooms. Just a five-minute walk from the pristine shoreline and steps from the shops and dining on Pine Avenue, Periwinkle Place combines coastal style with upscale amenities, including a pool with hot tub, private dock, golf cart, a private movie

Rooftop Views! Pool, Spa and Game Room!

Love Me Blue by Exclusive Vacations VR24-000043 Welcome to Love Me Blue, part of our Exclusive Collection. This luxury beach home offers four bedrooms, four and a half baths, located on the north end of Anna Maria Island! Just a three-minute walk to the serene Bean Point beach and one mile to the shops and restaurants of Pine Avenue, this stunning home combines resort-style amenities with elegant island living. Featuring a rooftop deck, private pool with a spa, and exclusive touches like a

Bleuphoria! Rooftop Views and Poolside Fun!

Bleuphoria by AMI Locals Welcome to Bleuphoria, a four-bedroom, four-bath luxury beach home on the peaceful North End of Anna Maria Island. Just three houses away from the sugar white sands of the Gulf and steps from Pine Avenue’s boutique shops and restaurants, this designer retreat delivers modern coastal elegance and resort-style amenities. With a private heated pool and spa, rooftop deck with panoramic Gulf views, and thoughtfully curated spaces indoors and out, Bleuphoria is your dream

Luxury home! Pool and Spa, Golf cart, and Bikes

Sweet Caroline by Exclusive Vacations VR23-000009 Welcome to Sweet Caroline, part of our Exclusive Collection. This luxury four bedroom, four and a half bath Anna Maria Island vacation home just one small block from the Gulf beaches. This coastal retreat blends refined design, resort-style amenities, and a relaxed island vibe. Guests can enjoy a private pool and spa, rooftop deck with bay views, and outdoor living and kitchen areas; all within walking distance of the Pine Avenue shops and

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

Island home with Pool and swim-up bar! Best

The Blue Crab by Anna Maria Vacations Home in Holmes Beach, Florida VRC-000057 Welcome to The Blue Crab, a stunning island retreat just three blocks from Holmes Beach! This luxurious four-bedroom, four and a half bath home boasts a tropically landscaped backyard featuring a private pool with a swim-up bar, fire pit, and hot tub. Surrounded by elegant, coastal farmhouse decor, the open layout offers plenty of space for family gatherings or friends’ getaways. Perfect for those seeking

Lap of Luxury by Duncan Real Estate

Welcome to Lap of Luxury!This home is new as of 2022 and has been meticulously built and designed to create a space for full relaxation. Lap of Luxury is only 150 steps from the white sand beaches of the Gulf of Mexico with beautiful views from every floor. It features 4 bedrooms and 5 and a half baths and is just a short stroll away from the historic shopping area along Pine Ave and the famous Bean Point beach area.Step through the zen inspired courtyard area to the main entrance.

Seaside Haven by Duncan Real Estate

Seaside Haven is an elegant Island property that promises an unforgettable experience. The 4 bedroom and 3 1/2 bath pool home is located on the Avenues in Holmes Beach and just a short flipflop walk to the Gulf powdery white beaches. This house features tasteful coastal-themed dcor that prioritizes guest comfort. Its gourmet kitchen and open floor plan provide ample space for family gatherings, complemented by a functional and relaxing outdoor living area by the pool.

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.

Elevator, Endless Summer by SeaBreeze Vacation

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER 4/27/23! All Drivers must be over the age of 21. Driver’s must provide valid US Driver’s License and US Vehicle Insurance. Endless Summer is the latest addition to SeaBreeze Vacation's portfolio. Pristine, newly constructed home features 7 beds/6 baths, an elevator, fantastic pool & spa, an EV Charger, and is just a 4-minute stroll from the shoreline

Private Ultra-Luxury 10 Bedroom | 14 Bath Mansion

Welcome to THE Estate Tampa Mansion! ✦10 master ensuites ✦14 Bathrooms ✦20,000 sf of space ✦saltwater pool | HUGE hot tub ✦professional gym | Ai personal trainer ✦chef's kitchen | commercial ice machine ✦lounge/bar areas ✦art gallery ✦billiard room ✦arcade | basketball | guitar hero | racing sims | air hockey | classic games ✦20-person dining table ✦This property is not suitable for children under 10 years of age.