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Mainsail – 1245 Big Oak
- 4 bedrooms and 3.1 bathrooms in Siesta Key, FL

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The health and safety of our guests, our homeowners, and our employees are our number one priority. In response to this pandemic, our team has adopted flexible policies for ALL GUESTS, including new reservations and existing reservations, that are arriving before August 31st, 2020. We understand that some may be uncomfortable traveling and our team will work with you to adjust plans.

Our guests can stay in private homes which offer safe environments with luxury amenities and activities to entertain both kids and parents. In addition, we have committed to additional safety standards, cleaning standards, social distancing practices, and more.

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Expert Cleaning

Our Professional Housekeeping Services are disinfecting our homes with CDC and WHO approved commercial cleaning products. All of our linens are laundered at a commercial laundry facility using an OZONE system for 100% Sanitation.

limited contact upon entry

Limited Contact

All of our homes have electronic lock systems that allow our guests to check in and check out directly at their home. Our private homes are just that – PRIVATE – So your family can stay close to home without being home.


Here For You

We are available 24/7 for guests. Our Property Managers are one call, text, or e-mail away with no call centers, auto-attendants, or call menus.

At A Glance ↑↓

  • Waterfront Home with Dock and Boating Access
  • Spectacular Waterfront Views from Multiple Levels
  • Heated Resort Pool with Sun Shelf,10-Person Spa, Covered Pool Patio with Bar, and More
  • Game Room off the Pool with Gaming Consoles and Seating
  • 6 Minute Bike Ride to South Siesta Key Village Shops, Nightlife, Restaurants, and More
  • Walk or Bike to Siesta Key Beach
  • 3 Bedrooms + Bonus Room - Sleeps 10 Persons - 1 King, 2 Queen, Twin over Full Bunk w/ Trundle
  • TV and Arcade Game Room off Pool area
  • Part of our Professional Linen Program
  • Parking for up to 5 Cars, Free WiFi, and HDTV Included
  • Property Manager Program - Let us help you Vacation the Right Way
  • Beach Chairs, Beach Towels, and Bikes Included - Inquire for More Details
  • Preferred Vendor Discounts - Rental: Beach Chairs, Bikes, Kayaks, Paddle Boards, Boats Tours
  • Free Shuttle Services (tip only), 4-12 persons
  • No Dogs or Animals Allowed

Description ↑↓

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!

This Private Home located on a dead end street is located within walking or biking distance to the South Siesta Key Village and it is directly on the Intracoastal Waterway (ICW). BRING YOUR BOAT AND DOCK IT BEHIND THE HOME! It is hard to find a home with this type of waterfront boating and fishing access, with better views, and more privacy all wrapped into one gorgeous package! The views of the ICW Waterway from ALL levels of this home are simply staggering. You'll be able to watch marine and bird life of all kinds, and some boaters as well! The pictures do not do it justice. You'll be able to watch sunrise from almost any room in the home, or just walk out onto the balcony, or down to the covered patio or pool area and take in the Florida sun there! When you want to head out and explore, you can do so on foot or on a bike. Siesta Key Beach and South Siesta Key Village - grocery store, restaurants, shops, nightlife and more are both a nice walk or comfortable bike ride away. You can also hop on the free Siesta Key Trolley to get to the Beach, South Siesta Village, or the Main Siesta Key Village area as well. You can also drop a kayak or paddleboard in right next to the dock at the small beach area next to the seawall and mangroves, and you can explore that way. It is perfect for a family, multiple families, and groups.

Everyone will love the Private Heated Pool and Spa that features an oversized sun shelf, upgraded pool lighting and fountain package, and an oversized pool patio that is perfect for lounge chairs and sun tanning. The Oversized 10-person Spa wil always keep everyone smiling and enjoying the water views. The covered patio features a large TV with lounge seating, a bar top area with serving station and seating, and an outdoor kitchen and Grill for the perfect family BBQ in the most picturesque Florida setting. There are multiple refrigerators, mini-refrigerators, wine refrigerators, and ice machines throughout the home. This is a very special property! Depending on vehicle sizes, there are 2 parking spaces in the Garage and there are up to 3 spaces in the Driveway.

This 3 bedroom with Bonus Room, 3.5 bathroom home, offers over 3500 square feet of living and vacationing space. There is Outdoor Dining areas on the main level balcony and in the covered pool patio bar area. On the interior of the home there is a dining for 9 people. The Living, Dining, and Kitchen spaces are wide open with plenty of space to get everyone together. The home offers ample privacy for all of our guests as 3 of the bedrooms have En Suite Bathrooms. The home offers 1 King Bedroom, 2 Queen Bedroom, and 1 Bunk Room that features a Twin over Full Bunk Bed with a pull out Twin Trundle Bed. The Bunk Room's main bathroom is on the main living level of the home.

This home is also a short drive to Downtown Sarasota and the Ringling Museum. It's only a little bit further, about an hour or two, to St Pete, Tampa, and Orlando as well as those areas have to offer for a quick day trip as well. Free WIFI. If you have any questions concerning our home, rates, amenities, or anything else, please send us an inquiry and one of our professional reservationists and property managers would be happy to help answer your questions. You are a couple of clicks away from paradise, and we look forward to seeing you soon and showing you why a Siesta Key Luxury Rental Properties vacation is the best type of vacation!

This home is also part of our Property Manager Program, so one of our dedicated Property Managers will assist you during the entire reservation and vacation process. We are here to help you vacation the right way and ensure you have everything you need, including any recommendations or advice to help improve your vacation!

This property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest.

Want to stay with us longer than 2 weeks? Great! We just ask that you coordinate a day and time with us so we can have an additional clean done during your stay. There is an additional cleaning fee required for this and we would be happy to provide you with a quote. If you want to have your linens and towels replaced during this clean, we can do that too, just let us know. We are passionate about maintaining our homes and keeping them clean so we appreciate your cooperation on this. We will require an additional clean for every 2 weeks that you are in our home.

Beach Towels and Beach Chairs are included. Don't forget to check out our Preferred Vendors for rentals, activities, tours, and more. Through our preferred vendors list, we offer Rental equipment: golf carts, mopeds, mini cars, umbrellas, bikes (daily/weekly), kayaks, paddleboards, fishing charters, adventure tours, sunset cruises, eco-tours and more. Our preferred vendors recommend some Services, Tours, and Equipment be reserved in advance due to limited space and high demand. After you've made your vacation rental reservation, feel free to inquire with your Property Manager on how you can secure your spot for these services, tours, and amenities. Or, if you would like to wait, you can check out these services when you arrive. Most of our preferred vendors offer our guests discounted services and priority status. Discounts vary between vendors, and our list of preferred vendors is being updated daily. Inquire today for more information and for instructions on how to add these packages to your stay.

Amenities ↑↓

Beach Access :
Siesta Key Beach
Beach Distance :
6 Minute Bike Ride
View :
Pet Friendly :
Internet Access :
TV Cable/Satellite :
Bed Size 1st/Master :
King - En Suite Bath
Bed Size 2nd Rm :
Queen - Ensuite Bath
Bed Size 3rd Rm :
Queen - Ensuite Bath
Bed Size 4th Rm :
Twin/Full Bunk
Square Footage, Est. :
3500 sq. ft. +
Parking :
2-Garage; 3 Driveway
Floor No. :
1-3 Floors
Balcony :
Yes - Multiple
Lanai :
Elevator :
Patio :
Yes - Oversized
BBQ Grill :
Full Kitchen :
Washer/Dryer :
Refrigerator :
Stove/Oven Elec/Gas :
Micro/Dishwash/Disp. :
Microwave :
Coffee Maker :
Ceiling Fans :
Water Front/Access :
Waterfront - Dock
Pool View :
Bathroom :
3 Full ; 1 Half bath

Contact ↑↓

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Reviews ↑↓


Siesta Key Luxury Rental Properties
5111 Ocean Blvd. Suite B, C & D
Siesta Key, Florida USA 34242
Hours of Operation: 9am - 5pm
#SiestaKeyLuxury #iHeartSiestaKey

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