Beautiful Siesta Key Beach Home 
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5238 Winding Way Siesta Key, FL 34242  
Located on Midnight Pass in the Twin Oaks Pond neighborhood.
2,500 to 4,000 / wk
10,000 to 16,000 / mo
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Single Family
Beach, City
Sleeps 6
3 Bedrooms
3 Bathrooms 3 full / 0 partial
1620 Square Feet
Private pool, Other / see remarks
WiFi
Coastal Beach Florida Vacations
2055 Siesta Dr #15400
Sarasota, FL 34277-1400
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Description
 

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
1987
Property details
Borders preserve / public land
Bedroom additional description
Primary bedroom split, Primary bedroom upstairs, Primary bedroom walk-in closet, Primary bedroom balcony
Dining room description
Formal dining area, Breakfast bar/nook
Kitchen description
Full kitchen, Oven, Range, Full fridge, Freezer, Ice maker, Dishwasher, Microwave, Coffee maker, Kitchen island
Laundry description
Washer, Dryer, Inside laundry
Other rooms description
Game/rec room, Screened room/lanai
Internal amenities
Bed linens, Bath linens, Beach towels, Beach chairs, WiFi
External amenities
Gas grill
Internal features
Remodeled, Vaulted ceilings
External features
Private yard / courtyard
Furnishing features
Fully furnished
Location
 
Address
5238 Winding Way, Siesta Key, FL 34242
Subdivision name
Twin Oak Pond
County/parish
Sarasota
Nearest airport
Sarasota/Bradenton International Airport (SRQ)
Location information
Located on Midnight Pass in the Twin Oaks Pond neighborhood.
Availability & Rates
 
 
Season Name
Min Days
Daily Rate
Weekly Rate
Monthly Rate
High
30
N/A
$4,000
$16,000
Low
7
N/A
$2,975
$10,000
Mid
7
N/A
$3,500
$14,000
Low 2024
7
N/A
$2,500
$10,000
Reservation, Deposits, Fees, & Terms
 
Accommodation tax
13%
Security/Damage deposit
$1500
Cleaning fee
$300
Processing fee
$250
Occupancy restrictions
No smoking (in unit), No smoking (on property)
Size
 
King beds
1
Queen beds
1
Twin beds
2
Sleeps
6
Bedrooms
3
Bathrooms
3
Approximate square feet
1620
Full Bathrooms
3
Details
 
Property type
Beach, City
Dwelling type
Single Family
Dwelling style
Detached
Unit style
On two levels
Fence construction
Other / see remarks
Pool description
Private pool, Other / see remarks
Parking
2 car garage, Driveway parking
Heating description
Electric heat
Cooling description
Central air
Activities
 
Water activities
Boating, Sailing, Canoeing, Kayaking, Jet skiing, Water skiing, Fishing, Beaches
Policies and Disclosures
 
Policies

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.

 

All listing information is provided by the managing or reservation agent, is deemed reliable but is not guaranteed, and should be independently verified. This listing is rented for short-term visits and not as a residence, and is not a place of public accommodation. Information is © Copyright 1997-2025 HERO PM and individual providers of data, who are bound to a membership agreement. HERO PM and all their websites are interactive computer services. Unauthorized reproduction strictly prohibited.