Luxury rentals in Siesta Key

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!

Experience the Ultimate in Coastal Luxury

Exclusive Amenities Include: • Private Heated Plunge Pool, Baja Shelf and Whirlpool • Pool Views on 2nd & 3rd Story Balconies • Roof top patio • Less Than 1 mile to Crescent Village • Less Than a 2 Minute Walk to Crescent Beach & Point of Rocks • Just a Short Drive to Siesta Key Village & Siesta Key Beach • Ping Pong Table / Air Hockey Table • Outdoor Lounge Areas • 8 Bedrooms, 8.5 Full Baths with Luxury Towels & Bed Linens provided • Spacious Balconies With Seating Area • Full Gourmet Kitchen

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

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.

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.

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

Golden Glow - Stunning Views!

Golden Glow by AMI Locals TPL26-000025, DWE5105519 Golden Glow is a brand new luxury five-bedroom, five-bath waterfront retreat located in the heart of Bradenton Beach on Anna Maria Island. Designed for elevated coastal living, this stunning new construction home offers breathtaking bay views, a private dock, and a rooftop deck built for unforgettable sunsets. Just steps from the Gulf beaches and minutes from Bridge Street dining and shopping, Golden Glow delivers the perfect blend of

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.

Steps to Beach/Siesta Village-Resort Pool w/Slide

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.

Siesta Key Modern Villa Retreat with Heated Pool &

Immerse yourself in the elegance of modern living at this stunning contemporary home, designed with sophistication in mind. Perfect for families, couples, and business travelers, this property is your gateway to Sarasota's best - from the sun-kissed shores of Siesta Key Beach to the vibrant streets of downtown Sarasota. Embrace the luxury within and the adventures that lie just beyond. Discover more below!

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.