Luxury rentals in Anna Maria

Pearl House at The Gemma

Just steps away from the quartz white sand of Clearwater Beach sits a brand new collection of homes, "The Gemma." With spacious layouts, modern amenities & upscale furnishings "The Gemma" vacation homes provide a haven for travelers seeking the ultimate beachfront experience. Whether you're savoring your morning coffee on a private balcony, basking by the pool and spa, or strolling along the powder-white sands of Clearwater Beach, "Pearl House" ensures that your vacation dreams become a reality.

Island home with Pool and swim-up bar! Best

The Blue Crab by AMI Locals Holmes Beach Vacation Rental VRC-000057 Welcome to The Blue Crab, a stunning island retreat just two 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 relaxation, recreation,

Tampa Luxe Waterfront Private Pool, Hot Tub & More

Welcome to the first and only Airbnb Luxe property in Tampa and St. Pete—where every detail is curated for your comfort. This professionally designed waterfront home with direct Tampa Bay access features a private pool, hot tub, dock, chef’s kitchen, fast Wi-Fi, electric scooters, Weber Grill, fishing & beach gear for your adventures & more. Perfect for families or groups seeking relaxation and adventure. Ask us about private chef services and curated local experiences to elevate your stay.

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.

Gulf Views/Walk to St. Armands & Beach-Resort Pool

Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation experience! Per City of Sarasota's Rental Ordinance - This home must be rented for a minimum of 7 nights, and it has a max occupancy of 12 adults, *but children under 6 years of age do not count toward the City's max occupancy count. Vunique Vacations restricts the total occupancy of the home to 16 persons, including adults and children under 6 years of age.

Chateau de la Siesta | Beachfront, Pool, Lanai Bar

Exclusive Amenities Include: • Private Beachfront & Sunset Views • Lagoon Pool, Heated Spa & Tiki Bar • Gulf-Front Firepit & Volleyball Court • Hammock Between Beachfront Palms • Gourmet Kitchen & Spacious Living Areas • 4 Gulf-View Bedroom Suites w/ Balconies • Tropical Landscaping • Starter Packs of Essentials for Kitchen and Bath • Beach Towels, Chairs, Cooler & Caddy Provided • Enhanced Cleaning by our CottageClean Team

Luxury 6BR Sarasota Retreat w/ Pool & Rooftop

Welcome to 2440 Floyd Street, a stunning, modern retreat in the heart of Sarasota. This spacious 6-bedroom, 4.5-bathroom home offers luxury, comfort, and privacy, making it the perfect getaway for families, groups, and corporate travelers. With a heated pool, private rooftop terrace, and a detached guest house, this home offers a true resort-style experience just minutes from Siesta Key Beach, Lido Key, and downtown Sarasota.

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

Gone Gulfin’ by AMI Locals Home in Anna Maria, FL 34216 Get ready for the ultimate beach vacation at Gone Gulfin'! This brand-new, five-bedroom, four-and-a-half-bathroom home is located just one block from the beautiful Gulf of Mexico beaches. The backyard is top-notch and features modern amenities to entertain family and friends including, a private pool, putting green, in-ground spa, and an unbeatable rooftop deck.

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!