Luxury rentals in Holmes Beach

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

Luxury home with Golf Cart, Bikes, Pool and Spa!

The Black Pearl by Exclusive Vacations VRC23-000114 Experience luxury and coastal elegance at The Black Pearl, part of our Exclusive Collection. This stunning black and white designed beach home offers a private black-bottom infinity edge pool and panoramic Gulf views. Located within walking distance of the pristine beaches of Holmes Beach and just steps from the free island trolley, this four-bedroom, five-and-a-half-bathroom home offers the ultimate Florida vacation experience. Perfect for

New stunning Beach House 1 min to beautiful beach!

Discover a stunning 7-bedroom, 7.5-bath beach house on Bradenton Beach, just a one-minute stroll from the shore. This beautifully designed retreat features spacious living areas, elegant decor, and luxurious amenities throughout. Enjoy the inviting pool surrounded by lush landscaping, perfect for relaxation and gatherings. Each bedroom offers comfort and style. With its prime location and exquisite design, this beach house is the ideal setting for unforgettable vacations and cherished memories.

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.

House of Agape | Modern Luxury Escape w/ Pool

BNB Breeze Presents: House of Agape! A modern Sarasota retreat crafted for Pure Luxury. Designed with love, this golden oasis offers a private pool, sleek contemporary décor, a premium Jura coffee bar, and a fully equipped garage gym. Top amenities elevate this beautiful property even more: • Private Saltwater Heated Pool - heated at NO extra cost from Nov 21 - April 1st. • Modern Luxury Space • Professionally Designed and Furnished • Gym Set Up • Outdoor Dining Space • Beach Supplies

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.

Sunset Reflections | Saltwater Pool & Game Room

🦩Exclusive Amenities Include: • 0.1 Miles to the Gulf and 5-Minute Walk to Bean Point • Heated Saltwater Pool and Spa with Waterslide and Baja Shelf • Rooftop Patio with Hot Tub, Fire Table, Wet Bar, and Gulf Views • Game Patio with Putting Green, Ping Pong, Foosball, and Cornhole • Lanai Lounge with Shuffleboard and 3 TVs • Beach Towels, Chairs, Cooler, Bikes & Caddy Provided • Outdoor Pool Lounge Area Includes Gas Grill • Indoor Game Room • 2 Paddleboards

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.

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.

The Palace ~ Walk to Beach/Rooftop Views

The Palace is a 7BR/7.5BA luxury retreat just 3 minutes from Holmes Beach 🏖️. Enjoy a private pool & spa with swim-up bar, rooftop deck with Gulf views 🌅, arcade room, pool table, indoor bar, and beach gear included. Perfect for families and groups seeking resort-style comfort, upscale design, and an unbeatable Anna Maria Island location 👑🌴.