check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar

Longboat Key Offers Luxury Condo Rentals

Longboat Key, Florida is known for its luxurious surroundings to relax in, beautiful beaches that provide a variety of water sports, and abundant wildlife that offers a glimpse of Mother Nature's unique creations. This quiet barrier island offers a variety of Florida condo rentals for any budget or need to enjoy a thoroughly relaxing vacation. Many of these condos offer views of the ocean, swimming pool access, full kitchens and Wi-Fi. Read on to discover some of the best things to do on Longboat Key.

Watersports

Longboat Key is known for its fishing, both backwater and offshore. Lighted docks are perfect for night-time fishing. The area has a number of mangroves that are home to redfish, speckled trout and other types of fish. Tarpon and Cobia are abundant on the beach. Numerous fishing and sailing charter companies are available on Longboat Key.

Those vacationers that are looking for adventure will not be disappointed with the selection of water sports available on Longboat Key. Boogie boarding, paddle boarding, windsurfing and parasailing offer fun ways for visitors to enjoy the warm waters of the Gulf of Mexico. Dolphin watching and cruising expeditions are available, as well.

Tennis

Tennis fans will be delighted with the tennis offerings in Longboat Key. The Resort at Longboat Key Club is considered to be one of the best tennis resorts in the United States. This award-winning facility can seat up to 3,500 fans in its stadium and has 20 premium Har-Tru courts. Cedars Tennis Resort, also on Longboat Key, has 10 well-maintained Har-Tru courts. In addition, this tennis resort offers a stocked pro-shop and expert staff on site to answer any questions that you might have.

Shopping

Shoppers will enjoy the variety of upscale markets and boutiques available in Longboat Key. St. Armand's Circle, which is just a short drive away from Longboat Key, is very popular with shoppers from all over the world. St. Armand’s features a large selection of upscale shops, jewelers, boutiques, and sidewalk cafes. Nearby downtown Sarasota offers many opportunities for retail therapy.

Dining

If you are yearning for upscale ambiance and cuisine, Longboat Key has a number of restaurants offering just that. There are also cafes, diners, and ethnic restaurants for visitors seeking something more casual. Enjoy chic cafes and bistros at the nearby Plaza at St. Armand's Circle. Harry's Continental Kitchens is a unique dining concept that offers both fine dining and gourmet take out on the other.

Spa and Relaxation

Longboat Key’s luxury resorts have spas and high-tech fitness centers. These facilities offer a number of spa and body treatments. Salons and day spas on Longboat Key are cutting-edge, luxurious faculties. Most offer a range of nail, skin and hair treatments. Nearby Lido Key also has a number of world-class luxury resort spas that offer luxurious spa treatments.

Weather

Longboat Key’s weather is warm and sunny throughout the year. The average temperatures stay around 73 degrees Fahrenheit. Although, the area may experience thunderstorms from time to time, they are usually short-lived.

How to Get There

The nearest major airport is Sarasota-Bradenton International Airport (SRQ). This airport is approximately 30 minutes from Longboat Key. Numerous car rental agencies, private car and limousine services are available in Sarasota and Longboat Key. There are also public transportation and trolley routes available to serve visitors to Longboat Key.

Longboat Key is a tropical paradise offering great shopping and dining, perfect weather, and wonderful accommodations. High-end restaurants and classy boutiques make Longboat Key the ideal vacation destination for travelers who enjoy luxury.

Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Longboat Key: Condos, Houses & More (1,223)

  • 1 - 50 of 1,223
Additional fees apply. Taxes may be added.
    • 2 BR
    • 1 BA
    • Sleeps 4
    14
      • 3 BR
      • 2 BA
      • 1 HF BA
      • Sleeps 6
      11
        NEW!
        • 2 BR
        • 2 BA
        • Sleeps 8
        2 Reviews
          • 1 BR
          • 1 BA
          • Sleeps 4
          20
            • 4 BR
            • 3 BA
            • 1 HF BA
            • Sleeps 8
            11
              • 3 BR
              • 2 BA
              • Sleeps 6
              29
                • 3 BR
                • 3 BA
                • Sleeps 6
                7
                  • 4 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 10
                  8
                    • 2 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 4
                    17
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      6
                        • 3 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 10
                        29
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          10
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            23
                              • 2 BR
                              • 2 BA
                              • Sleeps 5
                              10
                                • 1 BR
                                • 1 BA
                                • Sleeps 6
                                14
                                  • 3 BR
                                  • 3 BA
                                  • 1 HF BA
                                  • Sleeps 10
                                  19
                                    • 6 BR
                                    • 5 BA
                                    • Sleeps 20
                                    10
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 4
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6
                                        1 Review
                                          • 4 BR
                                          • Sleeps 12
                                          21
                                            View details for price
                                            • 4 BR
                                            • 3 BA
                                            • 1 HF BA
                                            • Sleeps 8
                                            12
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              13
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 4
                                                25
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  9
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    1 Review
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      13
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        97
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          28
                                                            • 3 BR
                                                            • 3 BA
                                                            • 1 HF BA
                                                            • Sleeps 6
                                                            12
                                                              • 5 BR
                                                              • 4 BA
                                                              • 2 HF BA
                                                              • Sleeps 10
                                                              12
                                                                • 2 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                1 Review
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  4
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    7
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      3
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 5
                                                                        17
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          6
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            8
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              9
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 4
                                                                                10
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 6
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    24
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      19
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 5
                                                                                        2 Reviews
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          9
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 6
                                                                                              • 2 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 5
                                                                                              14
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                3
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  11
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 5
                                                                                                    6
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      1 Review
                                                                                                      • 1 - 50 of 1,223
                                                                                                       

                                                                                                      Recent Longboat Key Reviews

                                                                                                      Great Place, Great View, Great Location, Quiet

                                                                                                      5 of 5
                                                                                                      Stayed a week and loved it, beach is beautiful, condo is perfect for family of 4, plenty of space, view is great. This was our first trip to Longboat Key and truly one of the best vacations I have had, been all over Florida. Quiet, not crowded, felt like private beach with only families. Drive north or south if you like to be around a lot of people, but if you are looking to escape the world, this is the place. Kids had a blast and adults got to relax. Owner easy to work with and it is updated nicely.
                                                                                                      • Submitted: Sep 26, 2016
                                                                                                      • Stayed: Jun 2016

                                                                                                      VILLA ZILLI-OUR BEST OCEANFRONT VACATIONS

                                                                                                      5 of 5
                                                                                                      We have vacationed at Jim's Villa Zilli oceanfront property 6 times in the past few years. Our stays at the Villa have been our most memorable Florida vacations to date. The oceanfront property is located directly on one of the most beautiful strips of beach on Longboat Key. Uniquely located Villa allows privacy along with access to the heated pool and BBQ grills with tables located within a few feet of Villa. Beautifully landscaped private oceanfront grounds with multiple patios. Beautiful evening sunsets. I have never felt so much at "home" as I do inside this professionally decorated home. Large kitchen, dining table for the whole family, a most comfortable living room with large screen TV over fireplace. The 2 bedrooms 2 full bathrooms offer total privacy for our family. The "classic deco" Florida color bathroom tiles are my wife's favorite. Home has always been clean upon our arrivals. Many great restaurants within a 5-10 minute. drive. Jim is a fantastic host. AAAAAAA++++++++++
                                                                                                      • Submitted: Sep 12, 2016
                                                                                                      • Stayed: Dec 2015

                                                                                                      What a Wonderful WEEK!

                                                                                                      5 of 5
                                                                                                      Thank you so much for sharing your "slice of Paradise" with us for 10 days! We have stayed at many other houses and condos in the past 8 years and this by far was the nicest house that we have "borrowed"! The pictures on the website were wonderful but really doesn't do it justice until you see it in person! The view was spectacular, the house was gorgeous and the furniture was so much nicer than any I have ever seen! The House was so clean and so well maintained. My Husband and I so enjoyed the Master Retreat, what a beautiful view from the Master Bedroom and Bath! The layout was perfect as we had different guests during our stay, we loved the split plan that gave everyone privacy. All were stunned at how beautiful this house was! The house was so clean and so well appointed with everything that we needed. We also enjoyed using the dock so that we could leave our boat the entire week! The pool and deck were wonderful and we loved the table and chairs under the protected area that gave us shade. I would recommend this house to anyone that would like a home that is well above others in the area! Can't wait to see you next year with the family as well as a "Girls Trip" in the Spring! Thanks so much!
                                                                                                      • Submitted: Sep 11, 2016
                                                                                                      • Stayed: Sep 2016