USA Gulf Coast Florida Sarasota Listing #49152

Penny Lane Cottage - Sarasota, FL

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24 reviews
Max. occupancy: 4 1 Queen Bed, 2 Twin Bed 2 bedrooms 1 bathroom 2 dog max 
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Charming Historic Home with Modern Updates on North Siesta Key

A lovely 1940s cottage in an ideal location just over the North Bridge to Siesta Key, this is the perfect spot to relax and experience all the benefits of the Sarasota area. Kick back in a quiet and peaceful setting dressed in beautiful landscaping complete with enchanting frangipani and banyan trees. The living room has classic hardwood floors, comfortable furniture, and a workspace. The adjacent sunroom, with a flatscreen TV, a corner couch, and bench seating, is the perfect place to watch a movie, read a book, or grab that afternoon nap. There are great restaurants in every direction but if you prefer to cook you will love the updated kitchen and outdoor grill. Shopping is easy with Trader Joe's, Morton’s, and Publix very close by.

The bedrooms are nicely furnished and very comfortable! The high-speed internet makes it quick and easy for remote workers and students to complete their projects on time. With a bright and welcoming interior and a terrific location close to Shell Beach, this home has everything you've been hoping to find plus that extra throwback charm. The shed has beach chairs, games, four bikes, and a cooler for your use. There is even an outdoor shower. Vacation your way!

What's nearby:
The home is close to Siesta Key Beach and Village but also very convenient to the great offerings of downtown Sarasota and St. Armands. Shell Beach and Galvin Park are both just a short walk away, so you'll have plenty of space to stretch your legs with the family dogs. You'll also have a number of terrific restaurants less than four miles away anytime you need a break from the kitchen.

Things to know:
High-speed internet and free WiFi!
Dog-friendly for a small, nightly fee! Dogs are welcome but must be registered upon making the reservation.

County permit number: 990010133056
City/town permit number: 23-000256
City/town permit number: VR22-00094
State/province permit number: DWE6805264

You must be 21 years or older to rent this property.




Washer/dryer : Private

Heating & cooling

Central AC


Partial AC

House rules


Kitchen & dining









Wireless router


Step-free access

Wide clearance

On-site activities

Adult bikes


Gas grill : Private


Beach chairs

Beach towels

Safety & accessibility

Limited mobility access

Accessible bath/shower

24 reviews

DIANE R. Dec 2022
The cottage is in a nice area with a nice tv.
Lauren C. Oct 2022
Great little house to stay in! If you’re looking for a quiet place to stay with your dog, this is the perfect house.
François L. Aug 2022
Sarasota est vraiment magique, le plus bel endroit de Floride? Sans doute, avec Siesta Beach et Anna Maria Island. Le cottage était impeccable. Merci
Penny Lane V. Jun 2022
The cottage provided a perfect environment for a few days of R&R! It is located on a charming block with mature trees and lovely homes.
It is immediately welcoming from the moment you enter! Beautifully appointed with quality furnishings that are comfortable and functional. The beds are absolutely heavenly! Bikes provide transportation to explore the area- a quick 10 min ride to The Village to shop or dine or to the beach to relax and enjoy the crystal white sands and turquoise Gulf waters. If you ride over the North Bridge you'll find Grocery stores and charming neighborhood boutiques and eateries. Cant wait to return to Penny Lane Cottage, it provides all one would want for a stay on Siesta Key!
Joanne G. Jun 2022
Penny Lane Cottage is stunningly charming. The location of this quaint little home is idyllic and perfect for walking and biking under the canopy of tropical leafy trees. Take a short walk to Shell Beach for an almost private escape to crystal clear waves lapping at your feet and then wash away the sand in the outside shower back at the cottage. The front yard is pet friendly and has just enough space tucked behind the white picket fence. I can’t wait to return to this wonderful home.
Lorraine L. May 2022
Penny Lane was the perfect cottage for a relaxing vacation. The location was quiet and close to everything we wanted. We enjoyed our stay and look forward to returning in the future.
Mary A. May 2022
We loved our stay and will definitely return. Not only was the house to our liking but the neighbors and the whole neighborhood was so quaint and welcoming. It was beautiful, private and yet close to everything you need.
Candela V. May 2022
Our stay at Penny Lane Cottage was wonderful! The location is perfect, very close to siesta beach, downtown sarasota, and a little downtown area near siesta key. The house is in great condition, all furniture looks brand new and has all necessary appliances. Also, it was very clean! The bikes and beach chairs were in great condition and very convenient since beach parking is usually full on the weekends. Biking to the beach took us less than 20 minutes. This is a perfect cottage for a couple or a family of 4! Would definitely stay here again.
Paul M. Mar 2022
This cottage is in a perfect location. Rode a bike to walk the Siesta key beach. Super quick drive to downtown and Southside village. Then returning to this relaxing cottage was such a treat. Everything is very comfortable - the landscaping is great. There were even bananas in the banana tree.
Claire d. Jul 2021
We had a great stay at Penny Lane! The cottage is nicely furnished, and very clean. We especially appreciated plentiful towels, a barbecue grill, and a very well equipped. kitchen. Kudos also to the very responsive management team.
Kris and sandra . Jul 2021
This is such a wonderful home away from home! I really hope to be able to make it back soon. I loved all the charm and little extras that were just right.
Alexa . Jun 2021
What a perfect little house! We needed a little getaway to disconnect and relax... and this was the perfect place to bring our fur baby along with us. We had a wonderful time and our beagle felt right at home. Our only regret is that we didn`t stay here longer! We will definitely be back soon! Thank you!
Maria . Jun 2021
This mini-vacation was a surprise Father`s Day present to my husband from our children and grandkids. They know we love Siesta Key and have been here a few times but never came this way. This little cottage was perfect. Beautifully renovated and very clean. The fact that is named after a Beatle`s song made it that much more special since my husband is a huge Beatle`s fan.
Gaby and gabriel . Jun 2021
This house is an absolute gem! This was my first time in Siesta Key and I will definitely be back. A weekend getaway was not enough and I`ll be booking for a week next time! Thank you for sharing this home with us. Best location, clean, and everything we needed.
Sheena M. Jun 2021
Photos don’t do this gorgeous, charming cottage justice. It had everything we could have needed or wanted, we loved every single thing about our stay here and can’t wait to go back!
Michelle M. May 2021
Loved the location and neighborhood most of all. The house is adorable and clean, bathroom was very cool and the outside shower was a bonus. It’s very quiet neighborhood not good for big family , loud gatherings or loud anything. It’s a great place for reading and writers and to get away from people.
Nichelle . May 2021
Love this little house! The area is so quiet and peaceful. I`ve come to Siesta Key many times but never stayed in the North End. So much better! Less crowded and quiet. We had a wonderful times and Calvin our dog loved it as well, although he spent most of his time indoors in the A.C. It was exactly what I needed to decompress before entering my crazy demanding job. Thank you for sharing your wonderful little house!
Pam S. May 2021
The cottage was very clean and location was good. Also, it was beautifully decorated.
Bradley S. May 2021
A short walk to Shell Beach for sunsets, or a nice bike to the Sarasota beaches. And plenty of private outdoor space to relax and enjoy the beautiful trees and plants at home. This house and location was a treasure.
Bess R. Apr 2021
Penny Lane proved to be the perfect place for my family. It is charming, bright and full of sunshine. It is beautifully appointed with lovely, new, comfortable furniture and appliances; everything is top notch. The kitchen has everything you need for making meals and a brand new grill out on the brick patio.

The owners have thought of everything; there are board games, bicycles, outdoor games (gracious yard to play) and fishing rods to use. There was a cooler there for us to use and many other thoughtful touches.

The location is great; it's a quick drive to the beach, restaurants, downtown Siesta and Sarasota and grocery stores. Very nearby is a Publix, Trader Joes and Morton's for anything you need.

The home was very clean upon our arrival and the management team was very responsive to any of our needs or questions. We found the home to be just as it was advertised/photographed.

We felt very at home there and can't wait to book again.

Brittany S. Mar 2021
This cottage is incredibly charming and eloquent. The property was spotless upon arrive. It had everything we needed for a comfortable stay, and almost everything seemed brand new. It is located in a nice, quiet area, but is just a short drive to all Siesta Key has to offer. It’s close to Publix as well. We were very impressed with this property, and the property managers. We would love to go back again in the future.
Lendy C. Feb 2021
What a gorgeous, quiet, and beautiful home. Had a wonderful time here!!!