Luxury rentals in Siesta Key

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

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.

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

400ft to Beach, Ocean View, Pool, in the Village

Siesta Key Dream’s largest and most luxurious vacation rental, features four levels, totaling 6-bedrooms, 9-beds, & 6 full-bathrooms. Notable attributes include: a heated-pool, hot tub, 2-balconies, a roof-top sundeck, parking, a backyard and an elevator. With a premier location, beach access point #4 is 400 feet away, and the Siesta Key Village is one block away. In addition to a highly desired location, the unique property design allows beach and Gulf of Mexico views from multiple levels.

Modern Home + Heated Pool + Spa +Walkable Downtown

NEW elegant and modern pool home in the heart of downtown Sarasota. A short walk to downtown's award-winning restaurants, shopping, marina and nightlife. Minutes drive from the world-famous white sand beaches of Siesta and Lido keys. Next to the Legacy Trail and Payne Park for biking, hiking, cafe and skate park. This professionally designed home is a fully equipped, family-friendly 5-bedroom/3.5 bath with private pool, hot tub, outdoor kitchen, office and pool table. Cert# 26-VR-000092

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

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.

60ft. Water Slide - Golf Simulator - Mini Golf

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.

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

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

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.

West Coast Best Coast! Steps to the Beach!

🌴 West Coast Best Coast is a luxury 7BR/7.5BA estate just two homes from the Gulf 🌊. Enjoy a resort-style pool & spa, rooftop deck with panoramic views, putting green, and chic coastal interiors. With 6 king suites, a bunk room, beach gear, and a prime location near Bridge Street’s dining, shops, pier, and marina, this stunning home is perfect for unforgettable Anna Maria Island getaways ☀️🍹🏖️