About the property
- House2069 sq. ft.
- Half Baths0
- Minimum Stay7 nights
Luxurious waterfront with dock, heated pool, 2 BR plus Den/BR. Walk to beach
*****ONLY ONE RENTAL PER MONTH, SO BOOK FAST TO SECURE YOUR SPOT****PLEASE PROVIDE DETAILED DESCRIPTION OF TRAVELERS WHEN REQUESTING A BOOKING****
The Pineapple Cottage is a special oasis of tranquility and comfort. Surrounded by the palm trees that symbolize Florida, it is a private home nestled on a canal that leads directly into Sarasota Bay. Our home is situated in the desirable neighborhood of Country Club Shores --- just a short ride from the world class shopping and dining at St. Armand's Circle and walking distance to the beautiful beaches of Longboat Key.
This elegant house has been thoughtfully renovated and decorated with a charm and sophistication that will give you a feeling of relaxation as if you were in your own home. The furniture has a Tommy Bahama vibe and all the linens, tableware and kitchen utensils are of the highest quality. Here are just a few of the amenities this house offers:
• Exquisitely decorated Master Bedroom with king bed, en suite bath with large walk in shower and french doors to the lanai
• Guest bedroom with king bed and large walk in closet/dressing room
• Den/third bedroom with queen size pull out sofa, garden view and pocket doors
• Gourmet eat-in kitchen with new stainless steel appliances and granite counters and mosaic back splash
• Large Lanai under air with sliders that open to patio and screened pool for relaxing and dining "al fresco"; enjoy the outdoors without any bugs or humidity
• Game table with chess, backgammon and even a roulette wheel
• 50" smart TV in Family Room and 42" smart TV in MBR - both wall mounted
• Verizon triple play --- with high speed internet and movie channels
• Free phone service
• Screened heated pool
• Patio overlooking canal for sunning
• Private dock --- bring your boat or rent one
• Weber gas BBQ
• Separate laundry room
While clearly you may be tempted to spend your days at The Pineapple Cottage, lounging on the lanai, enjoying the canal views or soaking in our heated pool, there is no shortage of engaging activities in the immediate area.
The Gulf of Mexico's beautiful white sand beaches are a short walk from the property and you will find that the Cottage has an ample supply of beach chairs and towels. There are also many amazing scenic beaches just a short car ride away including Lido Key, Siesta Key, Coquina and Venice beaches for Swimming, Boating, Fishing, Kayaking, Sunbathing, Watching Sea Birds and Marine Animals, Sunrises and Sunsets.
You can also find an amazing selection of Restaurants, Bars, Golf, Tennis, Arts Center, Movie Centers, Shopping, Kayak Tours, Segway Tours and Massage; all within a five to fifteen minute drive. Just over the bridge to the north is Anna Maria Island with its charming towns of Bradenton Beach, Holmes Beach and Anna Maria, where you'll find more Shops, Bars and Restaurants, Fishing Piers and Antique Shops. A 15 minute scenic drive south through LBK takes you past elegant homes, golf courses, small shopping centers, parks and nature trails. St. Armand's Circle, known for its upscale shops, fine dining and casual restaurants and cafes is known throughout Florida as having the best restaurants and shops in Florida. Venture a little further down the road and you are in Downtown Sarasota, for more Shopping and Restaurants, Art Galleries, Theaters, Opera House, The Famous Ringling Museum and The Marie Selby Botanical Gardens. For those who wish to explore further, to the south are the islands of Siesta Key and Casey Key, then Venice Beach. To the north St. Petersburg is about 45 Minutes, Tampa an hour, and Orlando about 2 hours. The area is ideally located for a Florida vacation or a winter get-away.
There is much to do... Or, do nothing at all, but while away the hours on a lounge chair with a good book at your peaceful retreat in the quiet neighborhood of Longboat Key where every day is definitely a vacation day.... filled with blue skies, sun, white beaches and the gulf coast breezes.
- Response rate:
- Response time:
- within one hour
- Calendar last updated:
- May 20, 2018
About Lynn Jacobs
We are a small family of three who live in Roslyn, New York. I discovered Longboat Key and its surrounding islands about thirty years ago when traveling to Florida on business. I never forgot the incredibly beautiful sunsets and Gulf beaches and the peace and tranquility I found on LBK, and, when I got married, I couldn't wait to share my "discovery" with my husband. We have since traveled the world together, but we always return to LBK. When we grew tired of "ho-hum" moldy and out dated vacation rentals, we started our search for the perfect vacation home and were fortunate to find "our" Pineapple Cottage.
Lynn Jacobs purchased this House in 2015
Why Lynn Jacobs chose Longboat Key
As they say, Location, Location, Location...We consider Country Club Shores, where our home is located, to be one of the best neighborhoods in LBK (and possibly Sarasota). We enjoy boating, kayaking and fishing so having the canal and access to the bay in our backyard is ideal. The beach is a quick stroll across the street. We often bring our dog, Lucky, when we visit and it is great fun to meet our many dog loving neighbors as we walk and admire the beautiful homes and manicured gardens throughout CCS. The location is ideal for a quick run to Publix or St. Armand's for a bite or getting off island to visit the "city". We love searching for off beat things to do and have discovered hot springs and even gondola rides. The "icing on the cake" is the cultural side of Sarasota including the Ringling Museum, shows and independent film festivals and events at Selby botanical gardens.
What makes this House unique
Being a home owner has enabled me to bring my personal attention to detail and style to The Pineapple Cottage. I have a passion for decorating and creating beautiful spaces. We love the layout of our home and that there are so many special areas for relaxation and entertaining. Even when friends are staying with us, we all seem to find our favorite spot in the house and it never feels crowded. Since we both still work, we also have plenty of work areas too; my husband favors the den. My favorite spot is on the lanai where I can close the french doors for privacy and gaze at the numerous egrets, herons and other sea birds fishing in the canal. Our son favors the heated pool, fishing from the dock and watching TV in the living room. No matter how often we visit, the wonderful swaying palm trees that surround our home are always a welcoming sight. In our absence, we have an amazing husband and wife team that keeps the Cottage spotless and attends to any concerns. We enjoy pleasing our guests and sharing our special oasis with them.
Pool / Spa
Local Services & Businesses
Sports & Adventure Activities
Check-in: 3:00 PM
Check-out: 10:00 AM
Canceled bookings will not receive a refund
They say, “you get what you pay for”, for once I felt we got so much more!
Seldom do you find such an exceptional property on the vacation rental market. I stayed with my wife, sister and mother and found everything to be “Top-Notch”. Tucked within the private neighborhood of Coutry Club Shores at the south end of Longboat key this house has it all. I highly recommend a morning stroll past the million dollar homes, or for those more ambitious then take the traffic regulated pedestrian crossing over Gulf of Mexico Drive to the beach.
During our stay we had kayaks delivered to the house and launched them from our dock for daily excursions on the water. One evening we were lucky enough to be joined by three dolphins as we entered the bay!
This private home was spotless for our arrival and the owners seem to have spared no expense with both fixtures and fittings, and their own time with house notes and local suggestions, to create the highest quality vacation experience for their guests.
Much appreciated, thank you again for a truly wonderful stay.
We gave my 92 year old mother the master bedroom and she could not have been happier, in her words, she “felt like a queen “
A Perfect Home away from Home
The Pineapple Cottage is a great home on Longboat Key, close to St. Armands, the Publix Grocery Store, multiple restaurants and of course the best kept secret of all the beach. With 2 bedrooms, 2 bathrooms and a study that can be used as a bedroom the home is extremely well appointed and the owner obviously cares about maintaining the property in a first class manner. The small pool is enclosed by a Lanai and perhaps best of all there is a large living area separate from the main house with sliding patio doors to the outside.
Like all homes there were some minor issues that needed attention but the owner, Lynn jumped on them immediately and they were all addressed to our complete satisfaction. The home is located on a canal in a community of beautiful homes. Minutes away and just across the road there is access to the miles long beach. There is no public parking so access to the beach is limited to those with homes/condos either on the beach or across from it. As a result there were never many people to interrupt your walk (especially in January!). Our 3 month stay was very relaxing and we would highly recommend this property to those looking for the privacy of a quality home on LBK.
Thank you for your thoughtful review of our Pineapple Cottage! It was my pleasure to have you and your wife as our guests and make your stay as comfortable and relaxing as possible. Our goal is make sure our guests feel like they are in their own home from the moment they arrive without the hassles of home ownership. Over the past three months, I actually came to think of you as more of a friend than a guest and I sincerely hope that you will stay in touch and come visit us again! Best, Lynn and Don
A very pleasant surprise!
This is our second year staying at this amazing home. We are so glad to see that Long Boat Key and our Pineapple Cottage were spared from the storms that hit Florida last year.
If you read my previous review what looked like perfection to us in 2016 has been since improved upon in 2017. A brand new bathroom right off the master bedroom suite wowed us to the point where we actually called the people that rented the house to us to find out where they had sourced the materials for our own home. My wife was so impressed with the hand painted sink, fixtures, mosaic tiling and beautiful custom vanity that she is ordering them for our own home. I am truly impressed with the way the vanity kept all of her things hidden (something I didn’t think was possible).
We had a few more surprises worth sharing. After renting several boats to take my son and his friend fishing around Long Boat Key we discovered that the new dock and bulkhead on the ocean canal behind this property is teaming with sea life. They both caught more fish in one afternoon than all the boats we had rented in Florida the last two years. We also had the beautiful experience of watching a sea manatee take shelter next to our dock for several days. It was incredible!
Exploring the Pineapple Cottage and Long Boat Key the last two years has been a great experience. My family has never repeated a vacation spot before. It is nice that we finally found a place which we all look forward to seeing every year. I would highly recommend this location to anyone except in the month of December. We already have dibs.
We are so glad that you chose to once again spend your valuable vacation time at our home. We certainly hope you return next year! The Pineapple Cottage is truly a labor of love and we so enjoy sharing our special oasis with our guests. We have been most fortunate to be able to improve our precious Pineapple Cottage with a beautiful new dock and sea wall plus a fabulous new master bath. I am sure we will have more surprises in store for you next year....we sincerely hope to see you again at our Pineapple Cottage. Best, Lynn and Don
Every year we plan our vacation in December. Usually someplace warm and relaxing with an ocean nearby. I find myself not looking forward to these excursions for many reasons. The thought of spending a lot of money to stay at another beat up hotel room, sleep in another uncomfortable bed at a major resort is not all that exciting to me. When we do go on vacation my wife usually ends up planning enough outside excursions to keep us from thinking about the mediocre room which would make most folks look forward to returning home to their own beds. We are both 50 years old and nothing has surprised us in decades. If we left a hotel or resort review in the past it was usually as a warning to others. This December I got an amazing present that we haven't felt on a vacation in years.
The Pineapple Cottage. It felt more like our home only nicer. Picture your dear friends the interior decorators have invited you to house sit, they leave you a long list of recommended places for you to eat, things to do and even people to clean the place. The hardest part of our trip was going home.
This place is a breath of fresh air. The beds, sheets, pillows and covers feel brand new, the theme of the cottage from the furniture, to the brass lighting fixtures inside and out, mosaic tiling, granite kitchen counter tops and even the painted mural that adorns the pool area where all a very nice reminders that this was the vacation from home that we were looking for.
We hardly used the beautiful kitchen during our stay except for the coffee maker and the refrigerator. We did use a handy list of restaurants suggested by the cottage management. They really spent their time recommending places and people from cleaning ladies, fishing boats charters, golf courses and beaches that would make our stay a better experience. Straying off go this list proved to be second best.
I would highly recommend the Pineapple Cottage to anyone who is tired of vacation disappointments, except of course in the month of December, because thats our time to enjoy it.
Wow --- thank you so much for your enthusiastic review! At the Pineapple Cottage we have tried to capture a home away from home feel where our guests will immediately relax and enjoy their staycation and all the area has to offer. Your words conveying your appreciation for the relaxing ambiance and decor of the Cottage are most appreciated! We certainly hope you return!
It was a pleasure being able to stay at the Pineapple Cottage during our recent stay over the summer during the ,months of June, July and August. The accommodations were above and beyond what we were hoping for. We would stay there again without hesitation.
Thanks, Dan Wonsch
Rates & Availability
Additional information about rental rates
Stated monthly rate and deposit may vary depending on length of stay, number of guests and other factors. Weekly and holiday rates are higher and a custom quote will be provided. Small dogs under 35 pounds are considered on a case by case basis. Additional damage deposit may be required.