Luxury rentals in Holmes Beach

Showstopper Beach Home Pool Spa Waterfall Elevator

Welcome to the Kingdom on Hyde, the crowning jewel of Arlington Park homes & a vacation lover's dream. Featuring 4 bedrooms & 6 baths spread over nearly 4000 sq ft w/ 20ft soaring ceilings. This jewel box features a heated pool & spa with dramatic 8ft waterfall feature, Thermador Appliances, commercial grade elevator, custom imported tile & finishes & 2-story living amongst the Live Oaks. Perfectly situated a stone's throw from Arlington Park & a short drive to Siesta Beach & Downtown Sarasota!

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

Lido Luxe Estate: Rental with Pool + Rooftop Deck

Lido Luxe Estate by Lido Key Vacations Vacation Rental License #VR25-00081 Minimum stay duration of 7 days/nights Experience unmatched luxury at Lido Luxe Estate, Sarasota's finest island retreat located in the prestigious Lido Key! This beautifully appointed six-bedroom, six and a half bath home offers a perfect combination of elegance, privacy, and entertainment. Located just a short six-minute walk from pristine Gulf beaches and the high-end shops and restaurants of Lido Key’s renowned

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.

Infinity Pool - 2 waterslides - Rooftop Gulf View

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. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway.

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.

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.

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.

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