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Longboat Key Vacation Rentals & Apartments - 372 Rentals Available

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372 Vacation rentals

1 / 17

Longboat Key House

  • 6
  • 20
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary



from $1,100.00 / night


1 / 22

Longboat Key Condo

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“This was a family holiday including 2 grandchildren, who loved every minute of the holiday and did not want to leave. Lovely 3 bedrooms condo in garden grounds, which lead to the beach, family swimming pool and adult pool and spa. 8 tennis courts....”
- Review left on 01/26/2017


Very Good (2 reviews)


from $215.00 / night

About Longboat Key

With endless white sand beaches and unobstructed views of the Gulf of Mexico, it’s no surprise that Longboat Key is a vacation hotspot. Book the perfect seaside Longboat Key condos for you and your family, and get ready for a vacation you won’t forget.

Introduction to Longboat Key

Located just off the Gulf Coast of Florida, Longboat Key is a barrier island that includes just four square miles of land and about 12 square miles of water. With such an expansive waterfront, Longboat Key is a true beach community. Many residents live here only in the winter, which means there are numerous vacation homes available throughout the warmer months.

Longboat Key Climate

Like many Gulf Coast communities, Longboat Key welcomes hot, humid summers and warm winters. The highs in July and August average about 90 degrees, while December and January days typically top out around 60 degrees. Longboat Key welcomes over 250 sunny days, and though the area receives an above average amount of rain, it’s extremely rare to spot snow along the coast.

How to Get Around Longboat Key

West Florida is a car lover’s paradise, with Gulf of Mexico Drive as the single main road that extends along the length of the key. Most Longboat Key condos are just a short drive away from both the main drag and the waterfront, so be sure to rent a car if you’re flying into Sarasota Bradenton International Airport.

Hit the Beaches

Longboat Key Beach faces the Gulf of Mexico and boasts clear, calm water and soft, white sand. You won’t find buzzing boardwalks or massive crowds here, but you will find plenty of space to swim and sunbathe. There are several public beach access points along the key, but arrive early to take advantage of limited parking.
At the northern edge of the key, Beer Can Island offers a secluded spot to swim, fish, and gather with friends. Since this beach is only accessible by boat, plan to rent a boat or charter a boat trip.

Explore the Gulf

One of the most popular ways to explore offshore is renting a boat. Outfitters like Cannons Marina and CB’s Saltwater Outfitters rent boats by the half day, full day, or week. Depending on what you want to do and the size of your group, you can rent a three-person motorboat for fishing, a six-person speedboat for cruising along the coast, or a 14-person pontoon that’s perfect for spending the day at sea. Be sure your group’s driver has a driver’s license and some boating experience under his or her belt.

Go Golfing

If you're a landlubber, rest assured there's plenty to do back on shore. Harbourside Course offers three different courses and 27 holes of golf. Play in the midst of flora like palmettos and palms, and enjoy the sparkling gulf views and refreshing breeze.

With easy beach access, activities on and offshore, and numerous Longboat Key condos for rent, this spot makes the perfect beach vacation.


Longboat Key Travel Tips

If you are looking for a vacation destination that includes white sandy beaches and a great mix of activities for the whole family to enjoy, make plans now to visit Longboat Key, FL. With the Gulf of Mexico on one side and Sarasota Bay on the other, there are miles of beach to be explored. The neighboring attractions in Sarasota, Bradenton, and Anna Maria Island offer more opportunity to explore the area while enjoying the Caribbean-like beaches of Longboat Key. Plan your family vacation today with and enjoy your visit from any of the many Longboat Key rentals on the island. 

Longboat Key Attractions

While it is no secret that the main attraction of Longboat Key is the easy access to many popular beaches, you can find many family centered adventures within nearby parks. Longboat Key offers plenty of opportunities to enjoy first class shopping and dining. Continental cuisine, fresh seafood, coffeehouses, and more are all available. Enjoy shopping at Longboat Key's Avenue of Flowers shopping area, the specialty boutiques at The Centre Shops or explore the galleries and shops at St. Armand Circle. If you are a collector of beautiful antiques you will want to be sure and visit the Soma District, located a short drive from Longboat Key.
The entire island is only 11 miles long but includes easy access to some of the most beautiful beaches in the state. While it may be hard to decide on a favorite beach during your first visit, you can find Longboat Key vacation rentals to choose from that provide you with the ideal starting point for access to one or several of the following beaches.
  • Greer Island
  • Cortez Beach
  • Holmes Beach
  • Manatee County Beach
  • Ann Marie Beach
  • Coquina Beach
  • Lido Key
Enjoy local dining and attractions such as these:

South Lido Park

South Lido Park a beautiful park covers 100 acres and offers attractive views of the Gulf of Mexico and the city of Sarasota. The whole family will enjoy kayaking, picnics, cookouts, nature trails, and many more seasonal outdoor activities. 

Blind Pass Beach

Blind Pass Beach may be one of the best kept secrets in the Longboat Key area. Located approximately 12 miles from Longboat Key this beach is a bit isolated, but offers the seclusion you might expect to find on a Caribbean vacation! Plan a day to enjoy the water, free parking, playground equipment to keep the younger family members busy and much more. You and your family can wander along the nature trail that includes dunes, rent a canoe or kayak to launch from the beach, or try your luck at fishing.
Other attractions you and your family may enjoy while relaxing in Longboat Key include Quick Point Nature Preserve and Islandside Golf Club. Additionally, you and your family are sure to enjoy are the Chartered Fish Tours and Ringling Bros. Barnum & Bailey Circus. The circus winter headquarters are in Bradenton which is a short drive from Longboat Key. Kids and adults alike will enjoy a tour of the museum and an opportunity to tour the grounds and enjoy regularly scheduled shows and exhibits.

Longboat Key Events

As a small town, Longboat key doesn't have a lot of events aside from their annual Holiday Night of Lights which features Christmas carol sing-alongs and a parade, but neighboring cities such as Bradenton provide ample entertainment and opportunities. Every Sunday you can enjoy Jazz Brunch on the Beach in Anna Maria. On New Year's Eve, a big celebration happens on Main Street in Bradenton.
Plan your family vacation travel today with and see for yourself why so many families like yours return to Longboat Key every year!
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