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Point Break – 336 De Mayo
- 8 bedrooms and 8.1 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 ↑↓

  • New Luxury Home in the Heart of Siesta Key Village w/ Elevator to ALL floors
  • Heated Resort Pool with Sun Shelf, Jacuzzi/Spa and More
  • Roof Top Deck with City and Gulf Views
  • Spectacular Siesta Key Village Views from Multiple Levels
  • Steps to Siesta Key Village Shops, Nightlife, Restaurants, and More
  • Short Walk or Bike Ride to Siesta Key Beach
  • 8 Bedrooms, 8.5 Baths with 4 True En Suite baths and 2 private baths just outside the bedrooms
  • 6 King Beds, 2 Full over Full Bunk Beds, 2 Queen Sleeper Sofa Beds
  • Arcade Room with Multiple Gaming Systems - En Suite Bath - Could be 9th Bedroom
  • Part of our Professional Linen Program
  • Elevator Available to All Floors
  • Parking: 1-2 Car Garage + 2-4 Cars MAX Driveway - No Parking between street and sidewalk
  • Free WiFi, and HDTV Included
  • Property Manager Program - Let us help you Vacation the Right Way
  • Beach Chairs and Beach Towels 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
  • Dog Friendly for Additional Fee

Description ↑↓

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

Located in Siesta Key Village, it's hard to find a home with a better location! It is steps to the grocery store, restaurants, shops, nightlife and more, and only a quick walk or bike ride to any one of the nearby beach access points. Just walk up, or take the elevator up to the 4th Floor, and then head up the spiral staircase to your Private Roof Top Deck where you can have a birds eye view of Siesta Key Village as well as Gulf Views!!! It is perfect for a family, multiple families, and groups. Everyone will love the Private Resort Style Heated Pool that features an oversized Sun Shelf for lounging, an oversized Jacuzzi Spa for those cool nights, and an enormous covered patio area with plenty of seating and a TV. Oh ya, and its right around the corner from the #1 Rated Beach in the USA by Trip Advisor.

This is ONE OF THE BEST Rentals on Siesta Key. Everyone will love being outside and using this pool in the warm Florida Sun, you'll love this Gorgeous new home here in Siesta Key Beach. This giant 8 bedroom 8.5 bathroom home, with an Elevator to all Floors, offers over 4600 square feet of living and vacationing space and multiple balconies on all levels and a Roof Top Deck. There is an Outdoor Dining area just off the Living Room area seating 8, and on the in the Interior Dining Room there is seating for 18-20 at a dining table that seats 10, and 2 bar top areas seating 8-10 total. It offers ample privacy for all of our guests as it has 6 King Bedrooms each with their own Bathrooms (4 en suite). There are 2 additional Bunk Bedrooms that feature a Full over Full Size Bunk Bed (each bunk bed sleeps 4). These 2 Bunk Rooms have a shared Jack N Jill Bathroom with a walk-in shower. There is also a Queen sleeper sofa bed in the Arcade Room on the 4th floor with a Balcony and Roof Top Deck Access. Oh ya, I said Arcade Room and Adults and Kids will love it with multiple gaming systems, a large TV, seating, and a en suite full bathroom; this will be a fun room for all. There is also a Queen Sleeper Sofa in the Living Room. The home will sleep up to 24 people in beds, so bring the whole family. Of the 8 Bedrooms; 2 of them are located on the 2nd Floor, 5 are located on the 3rd Floor, and the final bedroom is on the 4th Floor with the Arcade Room (9th bedroom). 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!

The pool and outdoor entertaining space is perfect for a BBQ, family fun, games, watching TV, or an alternative to the Gulf of Mexico. The Lounge Ledge will also be a big hit and it's the perfect place to sunbathe, and everyone will love the Sun Shelf and the oversized Spa, I promise you that! They'll also love the Pool Room/Game Room that is located just off the Pool Area behind the Garage. French doors opens up to the pool area to create an extended covered patio area that combines the spaces perfectly. This Pool Room has a refrigerator for pool beverages, deep freezer for ice and food storage, Ping Pong Table, and Foosball. This home is a short walk to Siesta Key Beach and within walking distance to Downtown Siesta Key Village Area as well.

Parking includes a 1-2 Car Garage, and maximum 4 cars in the driveway; NO Parking in the County Right-of-Way between the street and the sidewalk- strictly enforced by Sarasota County.
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.

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 n 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.

If you have any questions concerning our home, rates, amenities, policies, 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.

Amenities ↑↓

Beach Access :
Yes - Short Walk
Beach Distance :
Short Bike or Walk
View :
Gulf and City View
Pet Friendly :
Internet Access :
Yes - WiFi
TV Cable/Satellite :
Bed Size 1st/Master :
King - En Suite
Bed Size 2nd Rm :
King - En Suite
Bed Size 3rd Rm :
King - En Suite
Bed Size 4th Rm :
King - En Suite
Bed Size 5th Rm :
King - Private Bath
Bed Size 6th Rm :
King - Private Bath
Bed Size 7th Rm :
Full/Full Bunks
Bed Size 8th Rm :
Full/Full Bunks
Beds Pull-out :
Queen Sleeper
Square Footage, Est. :
Parking :
Garage and Driveway
Floor No. :
3 Levels - Elevator
Balcony :
Lanai :
Elevator :
Yes - To ALL Floors
Patio :
BBQ Grill :
Full Kitchen :
Washer/Dryer :
Refrigerator :
Stove/Oven Elec/Gas :
Micro/Dishwash/Disp. :
Microwave :
Coffee Maker :
Ceiling Fans :
Water Front/Access :
Pool View :
Bathroom :
8.5 Baths

Contact ↑↓

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Reviews ↑↓

Excellent location half a block from Village. Brand new house. Rooftop sunsets!

By: Trip Date: 11/25/2019

We rented this four-story home with an elevator for a family reunion. The property manager was very accessible even when we had a problem with said elevator. It was close to everything (the grocery store is practically across the street and each room has its own bath. Twelve of us stayed there very comfortably and we had empty bedrooms. My husband and I chose the fourth floor for privacy although the bedroom was much smaller than the master on the third floor but we were glad to have the whole level to ourselves. The ping pong table in the garage, the cornhole toss and whole family (all generations) video games were used nightly. We highly recommend this property.

(VRBO guest)


By: Trip Date: 05/26/2020

Amazing beautiful clean home… very big and was accommodating to my family!!!

(VRBO guest)


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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