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

Hospitality · Family · Location · Pool · Beach · Outdoor spaces · Indoor spaces · Walkability · View · Hot tub · Kitchen · Nearby · Cleanliness · Getting around · Condition · Grill · Value · Comfort

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

Pool · Family · Decor · Getting around · Accuracy · Indoor spaces · Cleanliness · Location · Sleep quality

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.

Hospitality · Pool · Cleanliness · Location · Family · Amenities · Indoor spaces · Hot tub · Accuracy · Comfort · Outdoor spaces · Kitchen · Decor · Layout · Quiet · Backyard · Nearby · Condition · Beach · Sleep quality · Getting around · TV · Parks · View · Check-in · Bathroom · Grill · Wifi · Noise · Checkout · Value

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.

Pool · Hospitality · Outdoor spaces · Beach · Comfort · Family · Hot tub · Location · Decor · Cleanliness · Walkability · Kitchen · Grill · Layout · Nearby · Indoor spaces · Access · Accuracy · Bathroom · Quiet · Laundry · Getting around · Sleep quality · Amenities

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

Hospitality · Beach · Walkability · Getting around · Accuracy · Outdoor spaces · Location · Bathroom · Sleep quality · Value · Quiet · Comfort · Nearby · Indoor spaces · Cleanliness

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

Family · Location · Pool · Getting around · Comfort · Walkability · Accuracy · Beach · Hospitality · Hot tub · Kitchen · Biking · Cleanliness · Amenities

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.

Location · Hospitality · Beach · View · Walkability · Kitchen · Nearby · Cleanliness · Quiet · Comfort · Family · Condition · Amenities · Decor · Outdoor spaces · Bathroom · Wifi · Indoor spaces · Getting around · Pool · Sleep quality · Checkout · Value · Check-in

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

Beach · Hospitality · Location · Family · Cleanliness · Pool · View · Getting around · Walkability · Amenities · Hot tub · Nearby · Indoor spaces · Decor · Kitchen · TV · Outdoor spaces · Comfort · Bathroom · Condition · Sleep quality · Biking · Accuracy · Pets · Quiet · Parking · Backyard · Air conditioning · Check-in · Layout · Wifi · Laundry · Access · Checkout · Value

Casa Del Sol | Rooftop Deck, Pool + Ocean Views

The best beach vacations feel effortless. At Casa Del Sol, every detail is thoughtfully prepared so you can arrive, settle in, and simply enjoy island life. ✨ Luxury made easy. 🚲 Complimentary luxury bikes 🏝 Just 30 seconds to the beach 🏊 Private heated pool & outdoor lounge 🏓 Ping pong & backyard games 🧴 Premium full-size amenities 🏠 Beautiful new construction 📞 Local hosts available 24/7 A stay designed to feel easy, elevated, and unforgettable.

Hospitality · Location · Cleanliness · View · Family · Beach · Pool · Amenities · Comfort · Layout · Outdoor spaces · Indoor spaces · Accuracy · Kitchen · Nearby · Walkability · Sleep quality · Biking · Decor · Bathroom · Condition · Hot tub · Quiet · Laundry · Solo travel · Value

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.

Backyard · Beach · Decor · Pool · Walkability · Location · Kitchen · Nearby · Indoor spaces · Cleanliness · Amenities · Condition · Accuracy · Hospitality · Outdoor spaces · Hot tub · Bathroom · Quiet · Family

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.

Hospitality · Beach · Location · Indoor spaces · Walkability · Pool · View · Hot tub · Family · Amenities · Decor · Condition · Accuracy · Outdoor spaces · Sleep quality · Kitchen · Grill · Value · Comfort · Nearby

Moondance - Steps to the beach! Heated pool!

🌙 Moondance is a luxury 6BR/6.5BA beach-block retreat just two homes from the Gulf 🌊. Enjoy stunning Gulf views, a rooftop deck, resort-style pool & spa, and chic coastal interiors. Steps from the beach and close to Pine Avenue’s dining and shopping, this dog-friendly home is perfect for relaxing island getaways ☀️🏖️🍹

Hospitality · Beach · Family · Pool · Indoor spaces · Location · Outdoor spaces · View · Bathroom · Cleanliness · Kitchen · Walkability · Hot tub · Decor · Layout · Comfort · Backyard · Condition · Sleep quality · Checkout · Amenities