Entire home
UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY
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Reviews
10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6192.8 sq m
Popular amenities
Explore the area

Longboat Key, FL
- Place, Longboat Key Beaches3 min drive
- Place, Harborside Golf Course at Longboat Key Club3 min drive
- Place, Mote Marine Laboratory & Aquarium4 min drive
- Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)21 min drive
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.
*****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.
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- Pool
- Spa pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (38 reviews)
House Rules
Check in after 3:00 PM
Minimum age to rent: 40
Check out before 10:00 AM
Children
Children allowed: ages 13–17
Minimum age for children is 7 years old.
Events
No events allowed
Pets
Pets allowed: less than 9 kg per pet (limit 2 pets total)
35 lbs. and under; multiple pets considered
Smoking
Smoking is not permitted
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
We should mention
A car is required for transport to and from this property
About the area
Longboat Key
Located in Longboat Key, this holiday 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 Siesta Key Beach. Mote Marine Laboratory & Aquarium and Marie Selby Botanical Gardens are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

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
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
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
2 Sept 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 27 nights in Aug 2021
Verified
10/10 Excellent
celeste s.
16 Nov 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Heaven!
celeste s.
Stayed 21 nights in Oct 2020
Verified
10/10 Excellent
Henry Y.
15 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
A Lovely Property
Henry Y.
Stayed 39 nights in May 2023
Verified
10/10 Excellent
Stew V.
10 Apr 2018
A Perfect Home away from Home
Stew V.
Verified
10/10 Excellent
Ryan D.
14 July 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
June/July Longboat Key Trip
Ryan D.
Stayed 35 nights in Jun 2020
Verified
10/10 Excellent
Barbara E.
7 May 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great neighborhood
Barbara E.
Stayed 28 nights in Apr 2022
Verified
10/10 Excellent
Jackie s.
12 Dec 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful!
Jackie s.
Stayed 28 nights in Nov 2021
Verified
10/10 Excellent
Francisco J M.
8 Sept 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Enjoyable Relaxing Comfortable Home, in Lovely Longboat Key
Francisco J M.
Stayed 12 nights in Aug 2019
Verified
10/10 Excellent
john f.
9 May 2019
Time at Pineapple
john f.
Verified
10/10 Excellent
john f.
9 May 2019
Time at Pineapple
john f.
Stayed 8 nights in Apr 2019
Verified
10/10 Excellent
Michael C.
24 Apr 2019
Pineapple Cottage
Michael C.
Stayed 8 nights in Apr 2019
Verified
10/10 Excellent
Stacy R.
13 Aug 2018
Beautiful home, fantastic location!
Stacy R.
Stayed 7 nights in Jul 2018
Verified
10/10 Excellent
Carie S.
29 June 2018
I couldn't of asked for a better vacation home in Longboat Key!!
Carie S.
Stayed 8 nights in Jun 2018
Verified
10/10 Excellent
Greg M.
7 May 2018
They say, “you get what you pay for”, for once I felt we got so much more!
Greg M.
Stayed 7 nights in Apr 2018
Verified
10/10 Excellent
Ted V.
15 Feb 2018
A very pleasant surprise!
Ted V.
Verified
10/10 Excellent
Ted V.
15 Feb 2018
A very pleasant surprise!
Ted V.
Archival
10/10 Excellent
Ted V.
7 Jan 2017
Pleasantly Surprised
Ted V.
Archival
10/10 Excellent
Daniel W.
26 Sept 2016
Pineapple Cottage
Daniel W.
About the host
Hosted by lynn jacobs
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
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