See all properties
Entire home

UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY

Photo gallery for UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY

Exterior
Welcome to The Pineapple Cottage!
The Pineapple Cottage is surrounded by swaying palm trees.
Exterior
Welcome to The Pineapple Cottage -- your home away from home!

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 62075 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Double Murphy Bed and 1 Double Futon

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Dining area

About this property

UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY

THIS PROPERTY HAS BEEN INSPECTED BY AND REGISTERED WITH THE TOWN OF LONGBOAT KEY RRR# 00134.2023

*****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 murphy bed and pull out sofa, garden view and pocket doors. Den also has two desks and printer for your business needs
• 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
• 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.

Our prices include all fees. No hidden fees.

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

heated pool with sunny deck !
Family-Friendly Anna Maria Island 3BR • Walk to Beach & Dining • Private Pool
  • Pool
  • Kitchen
  • Washer
  • Dryer
9.8 out of 10, Exceptional, (115 reviews)
Family-Friendly Anna Maria Island 3BR • Walk to Beach & Dining • Private Pool

House Rules

Check in after 3:00 PM
Minimum age to rent: 40
Check out before 10:00 AM
default

Children

Children allowed: ages 13-17
Minimum age for children is 7 years old.
default

Events

No events allowed
default

Pets

Pets allowed: less than 20 lbs per pet (limit 2 pets total)
35 lbs. and under; multiple pets considered
default

Smoking

Smoking is not permitted
Guests must return a fully signed rental agreement within one day of receipt. Failure to return rental agreement, will result in cancellation.
Guests must provide owner with names, ages and addresses of all individuals staying ; add'l overnight guests are not allowed w/o owner's consent.
Please note that certain guest fees may not be applicable to longer term bookings. Also, cancellation may be negotiable for longer rentals.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

We should mention

A car is required for transportation to and from this property

About the neighborhood

Longboat Key

Located in Longboat Key, this vacation home is near theme parks and on the waterfront. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Lido Beach and Longboat Key Beaches. Mote Marine Laboratory & Aquarium and Marie Selby Botanical Gardens are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching.
View more Vacation Homes in Longboat KeyOpens in a new window
Map
Longboat Key, FL

What's nearby

  • Longboat Key Public Tennis Center - 2 min drive - 3.1 km
  • Longboat Key Beaches - 3 min drive - 3.8 km
  • Harborside Golf Course at Longboat Key Club - 3 min drive - 3.4 km
  • Islandside Golf Course at Longboat Key Club - 3 min drive - 3.4 km
  • Mote Marine Laboratory & Aquarium - 4 min drive - 4.4 km

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 18 min drive

Restaurants

  • ‪Columbia Restaurant - ‬6 min drive
  • ‪Dry Dock Waterfront Grill - ‬3 min drive
  • ‪The Old Salty Dog - ‬5 min drive
  • ‪New Pass Grill & Bait Shop - ‬4 min drive
  • ‪Drift Kitchen & Bar - Lido Beach Resort - ‬8 min drive

Frequently asked questions

Does UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY?

As of Mar 30, 2026, prices found for a 1-night stay for 2 adults at UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY on May 27, 2026 start from $354, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 20 lbs per pet.

How much is parking?

Onsite parking is available at the property.

What time is check-in at UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY?

Check-in begins at 3:00 PM.

What time is check-out at UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY?

Check-out is at 10:00 AM.

Where is UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY located?

Situated on the waterfront, this vacation home is 1.8 mi (2.9 km) from Quick Point Nature Reserve and 2.7 mi (4.4 km) from Lido Beach. Harborside Golf Course at Longboat Key Club and Islandside Golf Course at Longboat Key Club are also within 3 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 18 out of 18 reviews
Rating 8 - Good. 0 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Luxio R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect all around

This rental was perfect in every way. Would do it again in a heartbeat and host is 10 stars.
Stayed 27 nights in Aug 2021
Verified

10/10 Excellent

celeste s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Heaven!

What a beautiful property and sparkling clean. We were fortunate to spend time at the Pineapple Cottage this Fall and enjoy the beautifully appointed home, pool, canal, patio, bikes, and short strolls to the beach. Thank you Lynn for sharing your gem with us!
Stayed 21 nights in Oct 2020
Verified

10/10 Excellent

Henry Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Lovely Property

A comfortable, beautiful property. Very nicely decorated with quality furniture. The Lanai has a great view and is really comfortable. The pool is delicious with views of the canal. Everything worked well: a/c, appliances, pool heater, TV’s, etc. Super comfortable beds. Nice bathrooms. Generously appointed with paper products, toileteries, towels, etc. The location is ideal. A 10 minute walk to the beach. 7 minutes by car to St Armands. There are several good restaurants close by. Publix and CVS a 3 minute drive away. There are several bicycles available for use in excellent condition. It was a pleasure coordinating with Lynn. I highly recommend this property.
Stayed 39 nights in May 2023
Verified

10/10 Excellent

Stew V.

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.
Verified

10/10 Excellent

Ryan D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

June/July Longboat Key Trip

Our stay at Pineapple Cottage exceeded our expectations. Lynn and Don have gone above and beyond to make this property truly special. No detail was left out from the pool toys to the bikes and fishing poles and everything in between. The house is very clean and well appointed with every convenience right at our fingertips. The beds and bed linens were very comfortable and there was plenty of space for our family of 3. Our 10yr old enjoyed the pool and fishing right off the dock where there is plenty of local wildlife like mullet and manatees to watch. We nightly rode the bikes provided by Lynn to watch the sunset across the street at the beach access point which is easy to get to. St Armands Circle was also a quick bike ride away. Lynn was available and responsive to any questions that we had during our stay. We've been booking with VRBO for over 10yrs and grew up in Tampa and this property is one of our favorites. We were so grateful for the extra precautions that Lynn and her staff took to keep us safe and informed during the coronavirus pandemic. We were easily able to stay isolated in the cottage with grocery deliveries and the location is ideal for not being around crowds of people. We practically had the beach to ourselves for the majority of our stay as Longboat is one of the quieter barrier island on the Gulf Coast. There was a mask mandate for LBK during our stay so when we did need to go out everyone seemed to be taking the guidelines seriously. We will absolutely return to this spot.
Stayed 35 nights in Jun 2020
Verified

10/10 Excellent

Barbara E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great neighborhood

Pineapple House is very convenient to AMI and Sarasota and beaches. Quiet area. Convenient to grocery store and restaurants. Lynn was very attentive to any issues that arose. Enjoyed our stay.
Stayed 28 nights in Apr 2022
Verified

10/10 Excellent

Jackie s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful!

We thoroughly enjoyed our visit to Pineapple Cottage! Everything we could possibly need was there…from beach towels, comfy beds, bikes, beach gear, pool, grill, to thanksgiving cooking needs. Thanks for sharing your piece of Heaven with us!
Stayed 28 nights in Nov 2021
Verified

10/10 Excellent

Francisco J M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Enjoyable Relaxing Comfortable Home, in Lovely Longboat Key

Extremely well care for house with all the comforts of Home, everything working perfectly.
Stayed 12 nights in Aug 2019
Verified

10/10 Excellent

john f.

Time at Pineapple

Lovely property, well cared for, well equipped, everything we had hoped for.
Verified

10/10 Excellent

john f.

Time at Pineapple

Lovely property, well cared for, well equipped, everything we had hoped for.
Stayed 8 nights in Apr 2019
Verified

10/10 Excellent

Michael C.

Pineapple Cottage

We had a wonderful visit to Longboat Key. The home was beautiful and location was perfect. The property owner, Lynn Jacobs, provided a comprehensive list of recommendations for sights worth visiting and eating establishments. We dined at several of Lynn’s favorite restaurants and her taste is spot on. Highly recommend this property if you are looking to vacation in the Sarasota area.
Stayed 8 nights in Apr 2019
Verified

10/10 Excellent

Stacy R.

Beautiful home, fantastic location!

We enjoyed our stay very much! Short walk to the beach, close to stores, restaurants and shopping. Everything we needed was there and we loved having the pool. We can’t wait to come back!
Stayed 7 nights in Jul 2018
Verified

10/10 Excellent

Carie S.

I couldn't of asked for a better vacation home in Longboat Key!!

The Pineapple Cottage is beautifully furnished with a great floor plan for a family. The kitchen, living room and bedrooms were perfect sizes and very comfortable! All were neat and clean! The lanai and the pool area gave us all the extra room we needed to feel like we ALL had our own spaces. Along with a short walk to the private beach, local shopping and restaurants, beautiful sunsets and fishing off their pier, my family had the vacation we dreamed of! We will definitely come back to the Pineapple Cottage in the future. Thanks Lynn and Don for your great hospitality! Steve and Carrie
Stayed 8 nights in Jun 2018
Verified

10/10 Excellent

Greg M.

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 “
Stayed 7 nights in Apr 2018
Verified

10/10 Excellent

Ted V.

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.
Verified

10/10 Excellent

Ted V.

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.
Archival

10/10 Excellent

Ted V.

Pleasantly Surprised

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.
Archival

10/10 Excellent

Daniel W.

Pineapple Cottage

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

About the host

Hosted by lynn jacobs

Host profile image
We are a small family of three. 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.

Why they chose this property

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 property 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 team that keeps the Cottage spotless and attends to any concerns. We enjoy pleasing our guests and sharing our special oasis with them.

Languages:

English
Tell us how we can improve our siteShare feedback

Hotels

Vacation Rentals