Luxury rentals in Anna Maria Island

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

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

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.

Luxury Private Pool/Spa, Rooftop, & Game Room!

🦩Exclusive Amenities Include: • Rooftop Terrace with Hot Tub, Dining, Fire Table, and Gulf Views • Private Heated Pool & Spa • 3 Minute Drive to Pine Avenue • 4 Bedrooms, 4.5 Baths • 3 King Beds, 1 Queen over Twins Bunk Bed • Multiple Balconies • Wolf / Subzero Kitchen Appliances, Regular & Keurig Coffee Maker, Dishwasher & Washer & Dryer • Beach Towels, Chairs, Cooler, & Caddy • Outdoor Lounge Area Includes a Putting Green, Ping Pong, 3-75"" TV’s, Gas Grill, Cornhole, & More • EV Charging

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.

Island home with Pool and swim-up bar!

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

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.

Tripletail | Beachfront | Pool & Spa | 4 King Beds

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.

Walk to Beach & Bridge St - Gulf-View Luxury

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. The result? Unmatched value for travelers who expect more from their getaway.

Palmetto Paradise~Heated Pool/Spa, Steps to Beach

🌴 Palmetto Paradise is a stunning multi-level luxury retreat featuring 4 ensuite bedrooms, open-concept living, and upscale finishes throughout. Enjoy a chef’s kitchen, 75” TV with fireplace, private balconies, elevator access, and a rooftop deck with Gulf views 🌊. Relax in your heated pool and spa, grill outdoors, and unwind in spacious comfort just moments from the beach. ✨🏖️

Luxury Estate | Pool, Spa & Golf Simulator

A stunning 4 bedroom 6.5 bathroom multi-level waterfront residence on Indian Rocks Beach delivering resort-caliber luxury from every level. Four en-suite bedrooms, a private dock, rooftop lounge, resort pool with spa, and a custom game room with a 30-foot bar, designed for guests who want more than a vacation home.