Property Description

Vunique Vacations – Distinct vacation homes for the discerning traveler seeking a truly unforgettable experience!

Welcome to The Overlook, a refined coastal retreat that blends thoughtful design, luxury amenities, and indoor-outdoor living in one of Siesta Key’s most coveted locations. With over 5,000 square feet of interior and exterior living space this modern estate offers Gulf-facing balconies, a rooftop terrace with fire pit, a resort-style pool, waterslide, oversized spa, Putt-Putt Golf, Ping Pong, Ring Toss, billiards, expansive outdoor entertaining areas, and spacious bedrooms — all just a short walk from the powdery sands of Siesta Key Beach and the vibrant Siesta Key Village. The Overlook offers both full and peaking Gulf views from most rooms and common spaces located on the 2nd living level as well as the rooftop terrace. The home is conveniently located to everything on Siesta Key. And, if you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft to the mainland Sarasota area (5 minutes) and downtown Sarasota (20-25 min) for access to the Sarasota’s Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, grocers, and more. And, day trips to Lido Key, Anna Maria Island, Venice Beach, Myakka State Park and so much more are all less than an hour away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away! So, whether you’re relaxing poolside, entertaining on the rooftop deck, or hosting friends and family, planning a day trip or getting out on the town, this estate promises a vacation experience like no other.

This Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all of your work or personal needs. TVs in all bedrooms. Window treatments throughout.

Accessibility:

In addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger. Baths 1–5 include walk-in showers for added ease and accessibility. Please see the Photos, 3D Tour, and Video for a closer look.

Floor Plan Description (by level):

Ground Level:

Guests are greeted with a private entry foyer with staircase and elevator access to all levels above, including the rooftop deck. There are also 2 garages for covered parking (EV charger equipped) in addition to driveway parking provided. The home’s beach gear is also stored here, including bikes, beach wagons and chairs, alongside a convenient fridge and freezer combination.

Outdoors, you’ll find a private resort-style pool with a sun shelf and ample chaise loungers for in-water and pool side seating. Just steps away, a Putt-Putt green, ping pong table, and ring toss provide active entertainment options. The covered pool patio offers an extensive array of seating featuring soft seating accommodating up to 14 people, a dining area that accommodates 14, and bar seating for up to 6. The outdoor kitchen includes a grill, beverage fridge with ice maker, and ample countertop space storage with drawers and cabinets. 3 TVs are placed throughout the covered pool patio for seamless viewing from all angles.

The First Level of Living (2nd Floor):

This level includes two private King bedrooms, Master bedroom 1 and bedroom 2. Master Bedroom 1, which features a king bed, walk-in closet, en suite bath with double sink vanity, a freestanding tub in shower, and access to its own private balcony with soft seating for two. Bedroom 2 features a king-size bed, walk-in closet, en suite bath with single sink vanity and walk-in shower.

At the heart of this level is the homes great room. The gourmet kitchen is fully equipped with a 48-inch range, double wall ovens, microwave drawer, dual dishwashers, toaster, coffee maker, and more. The kitchen is very well appointed with cookware, bakeware, dishware, cutlery, and specialty items like crockpots, blenders, and more. The kitchen is set up perfectly for you to host your family or to support private in-home catering services that our team can help you arrange through one of our preferred vendors for an additional cost. If you have any questions about these kitchens or their supplies, our reservationists would be happy to provide more details. A nearby pantry includes an additional full-sized refrigerator with ice maker, sink, trash pull-out, and utility cabinet. The living room offers an oversized custom modular sofa that comfortably seats 10, and an 80”+ TV. The adjacent dining space includes a table with seating for 8, and a large center island with bar seating for 6 and a nearby bar top with 4 more stools. Two balconies expand this space outdoors: a rear balcony which is furnished with a dining table for 14, and soft seating for 2 and a front balcony with additional soft seating for 2. A convenient half bath completes this level.

The Second Level of Living (3rd Floor):

This level was designed for both restful retreats and social fun. The Club Room includes a billiards table, built-in bar with beverage fridge and ice maker, lounge seating for 6, a built-in desk for remote work or reading, and soft seating on two balconies — including a swing style daybed, club chairs for shade lounging with peaking gulf views. A second laundry area with two stacked washers and dryers, folding space, rod, and utility sink adds practicality for large groups.

This level also houses four bedrooms, including the home’s Bunk Room. Bedrooms 3, 4, and 5 offer a king bed, en suite bath with a walk-in shower and vanity. Bedrooms 4 and 5 have private or shared balcony access with soft seating and sweeping views. Bedroom 6 is the Bunk Room and features a twin-over-twin bunk and a queen-over-queen bunk, plus an open closet system, a single sink vanity, and a bathtub/shower combo.

The Third Level of Living & Rooftop Deck (4th Floor):

The Overlook has a stunning rooftop deck, designed to elevate your vacation experience. This stylish space includes a covered lounge area with bar seating for 7, soft seating for 4, and a fire pit table surrounded by plush chairs. A built-in bar area below the outdoor TV includes a beverage fridge with ice maker, trash storage, and cabinetry. Railing-style umbrellas provide shade, while thoughtful design ensures everyone has a seat with a view. Whether sipping sunset cocktails, enjoying a game of cornhole, or watching the game under the stars, this rooftop retreat is the ultimate place to gather and unwind.

*Don't forget to check out our Photos, Videos, Matterport 3D Tour for this property*

And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!