Sarasota, Florida


Properties Available 336 properties available
Nestled at the northern tip of Longboat Key, this hideaway comes primed for laid-back Florida luxury. Indulge in carefree coastal living with direct dock access and a kayak included for exploring Longboat Pass or heading into Anna Maria Sound. Watch the sunset from home! 270-degree views of the beach, north to Anna Maria Island, the lagoon, and the
Beach to Bay View (580458)
Longboat Key, FL
House
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Siesta Tropical Villa By Siesta Key Luxury Rental Properties601 Avenida De Mayo Sarasota, FL 34242 Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key!Welcome to Siesta Tropical Villa! This stunning four-bedroom and three-bathroom vacation home comes with a private dock and a mesmerizing backyard, m
Siesta Tropical Villa (522788)
Siesta Key, FL
United States - FL - Siesta Key
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 14 guests
Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!Sea Spray by Siesta Key Luxury Rental Properties538 Canal RdSiesta Key, FloridaWelcome to Sea Spray, a beach and boaters paradise with a private dock across the street and just a block from the famous Siesta Key beach! This eight-bedroom and six-and
Sea Spray (522734)
Siesta Key, FL
United States - FL - Siesta Key Pet Friendly
Bedrooms 8 bedrooms
Bathrooms 6 baths
Guests 22 guests
Welcome to Casa Bella Vita, a stunning modern vacation home located on the southern end of Siesta Key, offering a luxurious and comfortable retreat for your stay. Just a short walk away from Point of Rocks, this home provides the perfect combination of convenience, relaxation, and beachside fun.As you step inside Casa Bella Vita, you'll immediately
Casa Bella Vita | Luxury Home w/ Heated Pool, Ping Pong Table, & Walking Distance to Crescent Beach! (281478)
Siesta Key, FL
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Blue Paradise by Siesta Key Luxury Rental Properties5234 Avenida NavarraSiesta Key, FloridaSiesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key!Welcome to Blue Paradise - a perfect vacation home with six-bedrooms and six-and-a-half bathrooms located just half a block away from the stunning Siesta Key
Blue Paradise (522715)
Siesta Key, FL
United States - FL - Siesta Key
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests
The Hideaway by Siesta Key Luxury Rental Properties320 Calle MiramarSiesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!Welcome to The Hideaway, a luxurious private gated home with four spacious bedrooms and four and a half baths. This home's stunning custom design and top-notch a
The Hideaway (SKLRP) (522745)
Siesta Key, FL
United States - FL - Siesta Key
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 10 guests
This beautiful, second-floor condo in the heart of Longboat Key offers a serene and luxurious retreat in a prime location. During your stay, you'll have access to the community waterfront pool where you can take a refreshing swim, lounge by the water, or enjoy the beach which includes the pavilion and restrooms. A laundry room is also available for
Another Day In Paradise (575626)
Longboat Key, FL
House
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Step into the exclusive embrace of Luxe Lagoon, where Siesta Key's charm intertwines with a sophisticated retreat. This haven of indulgence, designed for the connoisseur of luxury, unfolds with 7 bedrooms and 7.5 bathrooms, inviting up to 20 guests to experience an unparalleled fusion of elegance and comfort.As you venture into the backyard, a shim
Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly 🏝️☀️🐶 (588284)
Siesta Key, FL
House Pet Friendly
Bedrooms 7 bedrooms
Bathrooms 8 baths
Guests 22 guests
Welcome to Casa De Siesta, your ultimate island retreat nestled in the heart of Siesta Key Village. This stunning property offers a flexible rental option, allowing you to book the whole home as Casa De Siesta or choose to rent Villa Fiesta or Villa Margarita separately. Whether you're seeking a spacious getaway for a large group or a more intimate
Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach! (281482)
Siesta Key, FL
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Welcome to The Palms Cottage, a charming retreat nestled in the prestigious neighborhood of Palm Island on Siesta Key!As you step inside the home, you'll find a well-equipped kitchen complete with a regular and Keurig coffee maker, dishwasher, and all the necessary kitchen essentials. Prepare your favorite meals with ease and convenience, or brew a
The Palms Cottage | Pet Friendly Home w/ Private Pool & Spa, Walking Distance to Siesta Key Beach! (281557)
Siesta Key, FL
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Get lost in the intoxicating relaxation of Siesta Key, in this luxurious private home with a pool. This tropical retreat is a single-family residence located at the end of a secluded dead-end street in the opulent neighborhoods of northern Siesta Key. Surrounded by water on three sides, the view of the Inter-Coastal Waterway is visible from the co
Siesta Key Designer Home: *Pool, Gardens, Luxury* (303087)
Siesta Key, FL
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Enjoy beautiful views of the inter-coastal canal from this spacious, modern home just steps from Siesta Key Village. Located on a quiet cul-de-sac, this lovely private home features new mid-century dcor, a large paver deck with a private pool, and fantastic surrounding water views from the glass-enclosed great room and backyard. Four spacious bedro
Mod Livin' on The Key (244350)
Sarasota, FL
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests

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