Luxury rentals in Anna Maria

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

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

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

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

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.

Hospitality · Cleanliness · Condition · Location · Amenities · Decor · Accuracy · Comfort · Indoor spaces · Pool · Beach · Outdoor spaces · Bathroom · Quiet · Nearby · Family

Luxury, Downtown, Rooftop Views, Top Beaches

A spacious modern 4-story luxury townhome in the heart of Sarasota. Within walking distance to Downtown’s top restaurants, shopping, weekend farmer's markets, nightlife, live music, and more! Perfect for a luxury retreat or the business traveler looking for an elevated experience. Contemporary decor throughout the open floor plan and a private rooftop with an outdoor kitchen and gorgeous views of the city.

Cleanliness · Accuracy · Hospitality · Indoor spaces · Walkability · View · Location · Grill · Comfort · Getting around · Condition · TV · Beach · Bathroom · Sleep quality · Kitchen · Access · Layout · Family

Beachfront Condo - Sunset Views at Madeira Towers

Your mornings start with coffee on a wrap-around balcony overlooking the Gulf. Your evenings end with sunsets that stretch for miles. Step outside, you're on the beach. This beachfront corner condo has three bedrooms, two baths, and everything you need: beach chairs, umbrella, wagon, and towels all provided. Heated pool and hot tub, parking for one car, high-speed Wi-Fi. Complete package.

Hospitality · View · Indoor spaces · Check-in · Decor · Nearby · Amenities · Location · Kitchen · Checkout

Dream State ~ Gulf Front/Across from Beach!

Welcome to Dream State, a luxury coastal retreat located directly across from the beach in Bradenton Beach. Featuring six bedrooms, a resort-style heated pool and spa, rooftop deck with panoramic Gulf and bay views, outdoor kitchen, putting green, and walkable access to Bridge Street, this exceptional home offers everything you need for an unforgettable Anna Maria Island getaway.

Hospitality · View · Location · Cleanliness · Beach · Family · Condition · Kitchen · Comfort · Indoor spaces · Pool · Hot tub · Amenities · Accuracy · Walkability · Sleep quality · Value · Decor · Outdoor spaces · Pets · Bathroom · Layout · Nearby · Biking · Check-in

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.

Hospitality · Pool · View · Location · Sleep quality · Walkability · Accuracy · Beach · Outdoor spaces · Hot tub · Kitchen · Access · Checkout · Comfort · Nearby · Indoor spaces · Check-in · Cleanliness · Family

Bridge and Bay Escape - Brand New Listing!

Welcome to "Bridge and Bay Escape" a newly built home on the north end of Anna Maria Island. This luxury 4-bedroom, 5-bathroom vacation home is located on North Bay boulevard, just a short walk to Pine Avenue and right across the street from the Bayfront park. Managed by Doreste Properties

Hospitality · Walkability · Beach · Location · Sleep quality · Comfort · View · Accuracy · Outdoor spaces · Kitchen · Cleanliness · Family · Decor · Pool · Condition · Nearby · Indoor spaces · Check-in