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.

Siesta Beachfront Paradise: Infinity Pool & Spa!

Siesta Beachfront Paradise by Siesta Key Luxury Rental Properties Home in Sarasota Florida, 34242 Indulge in the ultimate beachfront luxury at Siesta Beachfront Paradise, a stunning new construction home that offers an unparalleled escape on the renowned Siesta Key. With 8 spacious bedrooms and 8 ensuite bathrooms, this exquisite property is perfect for large families or groups. Situated just steps from the world-famous Siesta Key Beach and 3-minute stroll to the charming Siesta Key Village.

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.

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 with a firepit.

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

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

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.