Dog-Friendly Siesta Key Bungalow, Wifi, Adorable Cottage Close to Siesta Key Beach w/Private Yard

Winding Way Siesta Key
$108.75 - $242.86 / night   in Siesta Key  
2 Bedrooms 2 Bathrooms Sleeps 4

Totally renovated adorable Siesta Key bungalow nestled on a shaded street just minutes from Siesta Key beach and the village of Siesta Key with a variety of shops, restaurants and nightlife. Drive into the circular driveway and park your car under the covered parking to be away from the 10 minute typical afternoon showers which freshen the air and quickly lead back to a wonderfully sunny summer day here at the beach. The yard is green and canopied, the street is quiet and sleepy and the beautiful cottage is nestled in between the trees. A perfect home for cicadas and the breeze gently rustling the tropical palms. Dog friendly location.

Enjoy a restful night sleep on the comfy king sized bed in a quiet petite community of homes. Read the paper on the porch overlooking the tropical yard, or watch the news on the TV in the bedroom. Make a fresh cup of coffee in the totally renovated kitchen and bring it to a second screened in porch where you can listen to birds singing as you overlook the greenery in a quiet ravine. Check out the local news on the Vios equipped TV, surf the net on the WiFi or just read on the comfy couch. Since there are two separate TV's, no need to decide who's favorite program to watch.

Meal prep is a delight on the brand new gas cooktop and double range oven in the fully-equipped kitchen. Dishwasher is ready for your vacation meal cleanup. The paneled new refrigerator will hold all of the drinks you might need for a day on the beach.

The guest room has a new queen bed. With two full bathrooms, the house makes for a quiet get-away for two couples or a small family with two older children.

The open floor plan makes for easy conversation and the filtered light from every room makes the house feel welcoming and friendly.

Two full baths and plenty of towels are available for your use. The main bath contains a tub/shower combination and the master, a shower.

Extra rooms with seating makes it easy for each person to have their own quiet private time, or gather together in the spacious living room with ample seating and TV. Each room has a pretty view of tranquility and greenery. Two are screened and outside. One is inside and fully air-conditioned. Plenty of space to choose.

One well-behaved dog is welcome, who will feel right at home in the house and in the yard.

New washer and dryer in the house make for light packing and more relaxing time. No need to go off site.

Covered parking for one car, and a graveled circular driveway gives room for additional parking. Beach chairs and towels are available in the house for your lounging by one of the best beaches in the world.

Enjoy privacy and convenience at once. Just 1.2 miles down Midnight Pass Rd and you are at the entrance of Siesta Key Beach. It's a 5 minute car ride or a 7 minute bike ride or take the 23 minute walk to the beach instead. Or call the Free-Ride Guy for a trip to either the beach or into the village. Side roads easily lead you to Siesta Key village where you can enjoy a myriad of restaurants and shops, listen to music, grab a drink or indulge in ice cream or pick up a few souvenirs or groceries as you stroll through town. Take a quick detour to visit the beach and the powder sands on your way home to your quiet bungalow for a relaxing evening in the spacious living room.

For a 3-D model view of the property, please paste the following link in your browser:

Booking season 2018: Jan/Feb/Mar full months only. Contact us for a quote.

Book today to enjoy your summer at the beach close to everything - yet tucked just far enough away on Siesta Key for restful quiet evenings at home.

5205 Winding Way Siesta Key, FL 34242

To purchase a vacation home like this one, Sue Ann Levin with Key Realty

Property Type: Home Beds: 3 Accomodates: 4 Check In: : 3pm Bedrooms: 2 Check Out: : 10am Bathrooms: 2.0 Pet Friendly: Yes
Air Conditioning Bathtub Cable Clothes Dryer Coffee Maker Covered Patio Dishwasher Family Friendly Fireplace Full Kitchen Hair Dryer Internet Internet Access Iron and Board Kitchen Laundry Microwave Open Patio Patio Pets Considered Refrigerator Satellite or Cable Screened Patio TV WIFI Walk to beach Washing Machine walk to Siesta Beach Lodging
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Contact Manager

Phone (941) 218-0847
  • Cleaning Fee:  $200
  • Security Deposit:  $500 - A Security Deposit will not be charged or refunded if a Limited Damage Waiver is available and selected.
  • Rental Deposit:  35%
Feb 19 - Mar 31
2018 February - March
$1,700.00 /Week   $6,000.00 /Month   Minimum Nights: 7  
Apr 1 - Apr 20
2018 April
$1,575.00 /Week   Minimum Nights: 7   Checkin:  Sunday   Checkout:  Sunday  
Apr 21 - Jun 15
2018 Late Spring (4-41 to 6-16)
$3,045.00 /Month   Minimum Nights: 28  
* Online bookings not allowed. Please email the booking agent.
Jun 16 - Aug 10
2018 Summer (6-16 to 8-10)
$3,150.00 /Month   Minimum Nights: 28  
* Online bookings not allowed. Please email the booking agent.
Aug 11 - Aug 31
2018 Late Summer (08-11 to 08-31)
$148.80 /Daily   $1,008.00 /Week   $3,840.00 /Month   Minimum Nights: 6  
Sep 1 - Sep 30
2018 September
$156.00 /Daily   $1,080.00 /Week   $4,200.00 /Month   Minimum Nights: 6  
Oct 1 - Oct 31
2018 October
$174.00 /Daily   $4,200.00 /Month   Minimum Nights: 6  
Nov 1 - Nov 16
2018 November
$900.00 /Week   $3,000.00 /Month   Minimum Nights: 7  
Nov 17 - Nov 24
2018 Thanksgiving
$188.57 /Daily   $1,080.00 /Week   $5,280.00 /Month   Minimum Nights: 6  
Nov 25 - Nov 30
2018 November
$900.00 /Week   $3,000.00 /Month   Minimum Nights: 7  
Dec 1 - Dec 31
2018 December
$218.00 /Daily   $4,301.00 /Month   Minimum Nights: 6  
Jan 1 - Jan 30
2018 January
$1,550.00 /Week   Minimum Nights: 7  
Jan 31 - Feb 18
2018 February - March
$1,700.00 /Week   $6,000.00 /Month   Minimum Nights: 7  
* Please Note: Taxes, fees, and deposits will affect the trip cost.
Reviews - 5 stars based on 6 reviews
Winding Way Siesta Key
5.0/5 stars
Great time, thank you!
Reviewed on Jan 11, 2018 by Tanjanna, Columbus, IN   Report
Winding Way Siesta Key
5.0/5 stars
I spent 7 days here and enjoyed it immensely! The home is spacious and comfortable and offers all the amenities of home. It is very close to the beach and the village, as well as being not too far from the highway if you want to motor on further up (or down) the road. I would definitely recommend this to anyone who is looking for a home-like setting with room to spread out and will definitely look for availability here the next time I come back to Siesta Key!
Reviewed on Jul 5, 2017 by A FlipKey verified reviewer,   Report
Winding Way Siesta Key
5.0/5 stars
Home and landscape are lovely. Backyard is serene & beautiful with old palm trees, a canal & fountain. Overall a great place to lay back & relax on vacation.
Reviewed on Apr 28, 2017 by Steve, Cincinnati, Ohio   Report
Winding Way Siesta Key
5.0/5 stars
Loved the Siesta Key area, but especially loved the house. It was very spacious with everything recently updated. It was in a very quiet area which is very nice! Would definitely stay here again !
Reviewed on Feb 20, 2017 by Judy, Mendota, IL   Report
Winding Way Siesta Key
5.0/5 stars
The house is great. It has been kept very clean. Everything you may ever need is here. The kitchen is amazing, king size bed is very comfortable. The area around the house is quaet and peaceful. The beach access just 5 min drive and Siesta Key village is very close too. We are very happy here and enjoy our stay a lot. Thank you very much.
Reviewed on Sep 6, 2016 by Svetlana, Toronto   Report
Winding Way Siesta Key
5.0/5 stars
wow !!! this location was amazing,the house was very clean and modern...lots of room....close to the beach...lots of shade in the back the enclosed screened in patio....would rent this home again....priced right
Reviewed on Jul 19, 2016 by Theresa, harrodsburg ky   Report

Dear Theresa, So glad you had a great time. We'd be very happy to have you back! Loretta

Manager Response Jul 19, 2016

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