Vacation Rental Listing 3 bed 3 bath in Siesta Key, FL. Beautiful Siesta Key Beach Home
beautiful siesta key beach home 
5238 Winding Way 
3 bedrooms
 / 1620 sq ft
 / 3 bathrooms
 / sleeps 6
$2250 to 4000
$10000 to 16000
Contact / Inquiry
Coastal Beach Florida Vacations
2055 Siesta Dr #15400
Sarasota, FL 34277-1400
Availability & Rates
Minimum Stay
Season Name
30 days
7 days
7 days
7 days
Low 2024
Reservation, deposits, fees, and terms
Accommodation tax
Security/Damage deposit
Cleaning fee
Processing fee
Occupancy restrictions
No smoking (in unit)
No smoking (on property)
Location and map
5238 Winding Way, Siesta Key, FL 34242
Subdivision name
Twin Oak Pond
Nearest airport
Sarasota/Bradenton International Airport (SRQ)
Location information
Located on Midnight Pass in the Twin Oaks Pond neighborhood.

Enjoy this beautifully 3-bedroom and 3-bathroom remodeled pool home on Siesta key, named the #1 Beach in the country! Brand new heated salt water pool has been completed! We are LESS THAN 1 minute to the powdered sugar sands and turquoise waters. The location is perfect and EVERYTHING in this home is Brand New! All flooring, linens, dishes, appliances, furniture...everything...just out of the box. Stay with us and enjoy the unique high-end finishes you are looking for in a luxurious vacation rental. This ideal location allows you to lounge by the pool, great fire pit by the pool, outdoor dining on lower and upper deck. Soak in all that Siesta Key has to offer. Not only can you conveniently walk, bike or drive to the public beach to your heart's content, but when it is dinner, you have many great options.

This two-story home features vaulted ceilings and open concept floorplan with extra-large windows providing ample in-direct lighting from every room. Bedroom windows have remote controlled window coverings available to your desired likeness with a touch of a button. The great room opens up to the no expense spared kitchen featuring brand new white, soft-closing cabinets finished with quartz countertops. The kitchen contains stainless-steel appliances paired with a retractable exhaust hood and recessed lighting; that combined with a reverse osmosis water filtration systemis sure to please the most discriminating guest. Kitchen counters extend into the breakfast bar with panoramic views of the lush Florida native landscape. The main level offers open living, dining for six, and kitchen area with a big flat screen tv. After a day at the beach, relax and enjoy the refreshing pool and the spacious outdoor deck ideal for sunsets and backdrop of Glebe Park. There is a brand-new outdoor Teak dining table for four and Weber grill for evening BBQs.

Down the hall from the living room, is a guest bedroom featuring a queen bed and a large window and access to the rear deck. The second guest room features twin beds and a large south-facing window bringing in the outdoors. The second bathroom is designed with a walk-in shower, custom-cut shower glass, an infinity drain, brushed gold hardware, and shiplap walls. On this level, you will find a beautiful super-spacious master bedroom featuring a new canopy king poster bed and luxury linens! The master offers a vaulted ceiling and windows with a walk-in closet is big enough for any fashionista. The master bathroom is a true oasis. Double vanity sinks with fluted cabinets and brushed gold hardware, a coastal chic chandelier, and vaulted ceilings just to start. A stunning stand-alone tub with a tropical view showcases the mural tiled wall. Just behind, a separate walk-in oversized shower with crackle glazed tile and custom-cut shower glass wall & door.

On the first level, enjoy the lush tropical landscaping and newly screened lanai on the side of the house with outdoor seating. Under the rear deck is a similarly sized paver patio, open-air patio table with 6 chairs, and overlooks the private backyard which is extensive in size features a brand-new heated pool and fully fenced yard. You will also find the first floor has ample space for parking, includes a storage unit and multiple entertainment spaces with bikes, beach cart, boogie boards, beach chairs, umbrella and corn hole all you will need for a day at the beach!

If you are looking for an awesome upscale Siesta Key experience, Congratulations! You have found it!

Year built
Property details
Borders preserve / public land
Bedroom additional
Master bedroom split
Master bedroom upstairs
Master bedroom walk-in closet
Master bedroom balcony
Master bathroom
Full master bath
Separate shower and tub
Dining room
Formal dining area
Breakfast bar/nook
Full kitchen
Full fridge
Ice maker
Coffee maker
Kitchen island
Inside laundry
Other rooms
Game/rec room
Screened room/lanai
Internal amenities
Bed linens
Bath linens
Beach towels
Beach chairs
External amenities
Gas grill
Internal features
Vaulted ceilings
External features
Private yard / courtyard
Furnishing features
Fully furnished
King beds
Queen beds
Twin beds
Approximate square feet
Full Bathrooms
Property type
Dwelling type
Single Family
Dwelling style
Unit style
On two levels
Fence construction
Other / see remarks
Private pool
Other / see remarks
2 car garage
Driveway parking
Electric heat
Central air
Water activities
Jet skiing
Water skiing
Policies and disclosures

Vacation costs include rent, processing fee, departure clean fee, applicable taxes and damage deposit.   In addition, where applicable, the following may apply:  HOA or condo application fee, community or golf transfer fee, pool heat fee, electric overage fee, pet fee (per pet), additional cable fee plus taxes as applicable.

Owner may apply the damage deposit to satisfy any obligation of Guest(s) to Owner, Broker, or any third party including, without limitation, electric, telephone, additional cable, cleaning charges, missing or broken access devices, wire transfer or bank charges, taxes, and damages of any nature. Any remaining Damage Deposit balances will be refunded to Guest(s) after all final bills have been received by Owner (refunds may take approximately 60 days to allow for receipt of final bills). Any damages caused by Guest(s) or their guests may be deducted from the Damage Deposit but will not operate to limit Guest(s) liability for amounts exceeding the amount of the Damage Deposit. There may be a damage deposit waiver fee added to the rental agreement should it be offered for the property.

Guest(s) may, upon providing Broker with written notice by email, may cancel this Agreement (Cancellation). If Tenant(s) cancel this Agreement prior to the arrival date, Guest(s) shall be obligated to pay all rents, fees, and other payments paid, or to become due, pursuant to this agreement (other than the Damage Deposit) as liquidated damages for such Cancellation.  Guest(s) will be eligible for a refund minus a $200 cancellation fee provided that Broker, using efforts it deems reasonable in its sole discretion, places a replacement Guest(s) for the same rental period at the same rental rate (shorter periods and/or lower rent will result in a pro rata reduction of the refund). Owner and Broker shall not be responsible for any costs Guest(s) may incur for travel or other arrangements in the event of cancellation by Owner or Guest(s). Broker recommends that Guest(s) obtain travel interruption insurance but makes no representations regarding the scope of coverage under any such insurance policy.


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