Vacation in Paradise Search Sarasota's Most Beautiful Rental Properties

Lido Key and Longboat Key Vacation Rentals

Welcome to Florida Vacation Connection, where you will find your perfect Sarasota area vacation. Our selection of exceptional, privately-owned Lido Key and Longboat Key vacation rentals are ideally located adjacent to world famous Sarasota, Florida. Whether you prefer to stay on a beautiful white sandy beach; or the waters of Sarasota Bay beckon you - we have over 100 beautiful Lido Key and Longboat Key rentals to choose from. Don't pay top dollar for a small hotel room - make yourself at home and enjoy the unique quality that a vacation rental home or condo has to offer!

Longboat Key Properties

Lido Key Properties

A line of chairs and umbrellas on the beach

Beachfront Properties

Chairs lined up on a deck overlooking a pool and the bay off in the distance

St. Armands Properties

About Sarasota, Florida

Longboat Key and Lido Key are two of Sarasota's most beautiful barrier islands

When you stay in one of our Lido Key or Longboat Key vacation rentals you will find the world's most beautiful white powder sand beaches and be within close proximity to all that the area has to offer. Sarasota is considered the jewel of Florida's Cultural Coast - wWith a vast array of arts and cultural attractions. We are well known for eclectic art galleries, beautiful museums, Broadway-worthy live theater and a world class opera, ballet and symphony orchestra.

Both St. Armand's Circle and Sarasota's thriving downtown offer five star dining, boutique shopping, live music clubs and rejuvenating spas. Whatever your dream vacation - from the beaches, to the golf courses, to the arts - Sarasota has it all. Of course, if you'd prefer to do nothing but relax on the beach all day, there is no better place than at our Lido Key or Longboat Key rentals!

Book Your Perfect Vacation

Look at That | A Guide to Sarasota Area Museums

The outside of one of the most popular museums in Sarasota.

When you think of what to do on a Florida vacation, you probably picture spending your days on the beach, soaking in the sunshine. However, there’s so much more to do and see when visiting...read more

Plan the Ultimate Florida Summer Vacation

A couple walking on the beach on their Florida summer vacation near Sarasota.

Thanks to remote work, getting away for more than a week is easier than ever. This summer, pack your bags and laptop and escape to Florida, specifically the Sarasota area. Lido Key and Longboat Key...read more

Tiki Bar Hopping by Boat Near Sarasota, Florida

Sarasota, Florida, is a paradise for boaters and beach lovers alike, offering crystal-clear waters, stunning sunsets, and a laid-back tropical vibe. One of the best ways to experience the area’s waterfront lifestyle is by hopping...read more

Our Longboat Key, Lido Key, and St. Armands properties come in a range of sizes, from 1, 2, and 3-bedroom condos to 2 to 5-bedroom homes. Our variety means we can accommodate everyone from the vacationing couple to the reunioning group of ten. Every property provides WiFi, a fully-equipped kitchen, and bed and bath linens. All offer community pools and outdoor entertaining spaces, and many have their own private pools. What else can you expect? A good portion of our properties include washing machines and dryers, fitness centers, tennis courts, hot tubs, grilling areas, shuffleboard, barbecue grills, and docks. As for situating your car, many of our homes offer driveways, garages, or otherwise assigned parking.

Guest comfort, enjoyment, privacy, and safety are our top priorities, which is why every property is strictly vetted to ensure it meets our quality standards.