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AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool

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Experience the classic elegance of our lobby, featuring a polished granite island, wooden cabinetry, and a large ornate mirror.
Property video
Prepare meals in this well-lit kitchen with a large island and ample counter space.
Enjoy a spacious open-plan living area with a large kitchen, comfortable seating, and a view of the outdoors.
Relax on the balcony with a view of the surrounding landscape, featuring striped sofas and a metal table.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms7 bathroomsSleeps 106300 sq ft

Popular amenities

  • Parking available
  • Beach view
  • Hot tub
  • Dryer
  • Pet-friendly
  • Washer

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool

Indulge in unbeatable waterfront living in this breathtaking Siesta Key vacation rental, nestled on the serene waters of a luxury peninsula. Marvel at beautiful sunsets from your very own private pool area or from the charming terraces that adorn the third and fourth levels of this enchanting Siesta Key vacation rental. Spanning an expansive 6,300 square feet, this vacation home rental in Siesta Key offers a lavish retreat where even large families can relish in absolute privacy.

Entertain in style within the sprawling outdoor spaces, complete with a delightful grill area for hosting a family cookout and a refreshing pool and luxurious hot tub for ultimate relaxation. Discover cozy and inviting outdoor patios on each of the three levels, featuring a fire pit on the first and a fireplace on the second floor, perfect for unwinding under the beautiful Siesta Key sky.

This Siesta Key rental spoils you with amenities, including a street-legal golf cart powered by lithium batteries, accommodating up to six passengers, provided by The Toy Barn. Explore the island’s treasures effortlessly for just $75/day, exclusively available to guests of this exquisite Siesta Key vacation home rental. Immerse yourself in leisure within the game room boasting pool and skeeball tables, or ascend to the rooftop crow's nest for unbeatable panoramic views of Siesta Key. Unwind in the full bar/movie room, ensuring endless entertainment options.

Nestled on the North end of The Key, this Siesta Key rental offers a strategic location, minimizing your encounters with traffic. Embark on leisurely rides to The Village or the world-renowned Siesta Beach. Venture on over the North bridge to discover key destinations such as Southside Village, Selby Gardens, UTC, and downtown, all within easy reach by car. The possibilities are endless in this idyllic paradise, waiting to welcome you. Your next trip to paradise is closer than you imagine– book your well-deserved escape to Siesta Key today!

www.vacationDP .(c o m)

“The Lookout” can accommodate up to 13 guests with a bedding configuration as follows:
• Bedroom # 1, 1st Floor: King Bed (1) - Sleeps: 2
• Bedroom # 2, 2nd Floor: King Bed (1) - Sleeps: 2
• Bedroom # 3, 2nd Floor: King Bed (1) - Sleeps: 2
• Bedroom # 4, 3rd Floor: Bunk/Trundle Bed (2), Floor Mattresses (2) - Sleeps: 5
• Bedroom #5, 3rd Floor: King Bed (1) - Sleeps 2

POOL HEATER RULES:
Pool heat temp is set at 83º and runs each day from 7 AM until 7 PM from November 15-April 15. Outside of these dates, the Florida weather will naturally heat the pool. This pool is heated by a heat pump and is only capable of heating to around 15-20 degrees warmer than the ambient temperature. (If the high for the day is 55, the pool may only be able to reach 75).
The spa has a timer of 4 hours, once turned on and can be run at any time and will heat to 100º

NOTE: The boat dock is not allowed to be used for docking personal or rented boats unless you get approval from management!

VR Certificate: VR22-00113

AREA INFORMATION:

Experience the serenity of our world class beaches where you can swim, sunbathe, surf, paddle board, and fish. Take a morning walk down to the soft white sand of Siesta Key Beach or to little Shell Beach to find sand dollars and an assortment of other sea shells. Head to the South side of Siesta key to check out Turtle Beach; a more secluded beach with less people and great surf fishing on the south end.

Visit one of the centerpieces of Siesta Key, the AMI City Pier where there is great fishing and plenty of restaurants to choose from. Take a stroll down the Coquina Baywalk and Leffis Key to find a small nature walk with peaceful walking trails.

Take the provided bicycles all around the island and search for the 6 beaches that AMI has to offer (can you find them all?); Coquina Beach, Manatee Beach, Bradenton Beach, Holmes Beach, Cortez Beach and Anna Maria Beach (with Bean Point being part of that).

Our favorite Anna Maria Island Restaurants:
•Beach House Waterfront (Excellent Seafood)
•Ugly Grouper (Bar/Pub Style Food)
•Waterfront Restaurant (High End Seafood and Steak, Great ambiance)
•Hurricane Hanks (Bar/Burgers)

Our favorite Bradenton/Sarasota restaurants:
•KOJO (My personal favorite - High end Asian Fusion)
•Selva Grill (Amazing ceviches and high end courses-Try the KOJO sushi roll and Wagyu Skirt Steak!)
•Owen’s Fish Camp (Unique atmosphere, great seafood)
•Baker and Wife (American, great food)
•SKOB - Siesta Key Oyster Barn (Great happy house and oysters)
•Hyde Park Prime Steakhouse (High end steakhouse)

Our favorite Tampa/St Pete restaurants:
•Rococo Steakhouse (High end steakhouse)
•Texas De Brazil (All-you-can-eat Brazilian Steakhouse)
•Bern’s Steakhouse (If you can get a table-amazingly unique eating experience - WORLD FAMOUS)
•Ulele (Local Cuisine, Brew Pub, Michelin Star rated)
•Ocean Prime (High end Seafood)

Our favorite Casey Key/Venice restaurants:
•Pop’s Sunset Grill (Ma & Pa style bar and grill)
•Casasariano Italian Eatery (Italian)
•The Breakfast Cottage (Breakfast/Brunch)

Property manager

Destination Paradise - SRQ

Add dates for prices

Property amenities

Beach

  • On the beach

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 6.5 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels
  • Stereo
  • Video games
  • Video library

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Garden
  • Terrace

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 3 pets total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city center
  • Near the ocean
  • Next to a golf course
  • On a lake
  • On a river
  • On the waterfront

Things to do

  • Arcade/game room
  • Bicycles
  • Billiards/pool table
  • Boat
  • Golf
  • Heated pool
  • Kayak
  • Water sports equipment

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Bicycles
  • Garden
  • Unit size: 6,300 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
3 total (up to 50 lbs per pet)

Children and extra beds

Children are welcome

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

5

About the area

Map
Siesta Key, FL

What's nearby

  • Sarasota Memorial Hospital - 5 min drive - 4.5 km
  • Siesta Key Beach - 7 min drive - 4.4 km
  • Marina Jack - 9 min drive - 7.2 km
  • St. Armands Circle - 14 min drive - 11.9 km
  • Lido Beach - 17 min drive - 13.9 km

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 25 min drive

Restaurants

  • ‪Walt's Fish Market Wholesale - ‬5 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Red Barn Bar - ‬5 min drive
  • ‪CinéBistro - ‬5 min drive
  • ‪Sonny's BBQ - ‬5 min drive

Frequently asked questions

Does AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool pet-friendly?

Yes, this property allows dogs (limit 3 total) with a maximum weight of up to 50 lbs per pet.

What time is check-in at AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool?

Check-in begins at 4:00 PM.

What time is check-out at AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool?

Check-out is at 10:00 AM.

Where is AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool located?

Located in Bay Island, this beachfront vacation home is in the city center, 0.9 mi (1.5 km) from Shell Beach, and 2.8 mi (4.4 km) from Siesta Key Beach. Irma Beach and Siesta Key Farmers Market are also within 3 mi (5 km).

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AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 21 out of 22 reviews
Rating 8 - Good. 1 out of 22 reviews
Rating 6 - Okay. 0 out of 22 reviews
Rating 4 - Poor. 0 out of 22 reviews
Rating 2 - Terrible. 0 out of 22 reviews

10/10

Cleanliness

Reviews

10/10

Very nice property’s
Stayed 10 nights in Nov 2023

10/10

From the moment we arrived, we were in paradise. The property inside and outside were absolutely perfect. The communication with the property managers was easy and fast. The house is in an incredible location and was fun for all ages. I highly recommend this house and hope to be back again soon! I was definitely not ready to leave paradise.
Stayed 7 nights in Mar 2025

10/10

Beautiful home, spacious and perfect location!!!
Stayed 4 nights in Mar 2023

10/10

Amazing property with plenty of space for large families.
Stayed 7 nights in Jun 2024

10/10

The house was great. Better than the pics and the pics are great.
Stayed 7 nights in May 2024

10/10

Property was everything it was advertised to be. We loved our stay. Travis was extremely responsive to everything we asked for. Highly recommend this property
Stayed 6 nights in Mar 2023

10/10

Beautiful house and a beautiful setting. Travis, the house manager, was always available for questions and needs. Would definitely book again.
Stayed 6 nights in Jul 2022

10/10

This property is a great size for large families! There is a space for everybody, and the house is clearly maintained very well. The location is very convenient to the beach, Publix, and location restaurants. The property manager responded to questions super quickly and was really helpful. We would highly recommend to others and would stay again!
Stayed 5 nights in May 2022

10/10

This is a beautiful house, in a quiet luxury neighborhood. Each family member had their own wing and we felt like royalty. The property manager was super accommodating and quickly solved any issues that arised.
Stayed 3 nights in Sep 2022

10/10

Everything was exceptional, the house was beautiful. Everything was taken care of immediately and very friendly and helpful. Not a single complaint. Hated to leave! Absolutely amazing
Stayed 5 nights in May 2024

10/10

Nice quiet location. Back area was great for hanging out. Nice shower head with good pressure. Hot water was almost instant. We did not cook so not sure how well kitchen appointed but looked good at a glance. Would definitely rent again.
Stayed 5 nights in Aug 2022

10/10

This spacious, impeccably clean house is wonderful for large groups. The amenities — swimming pool, hot tub, paddle boards, pool table, etc — and several common areas make it an ideal place to relax, gather, and cook without having to leave. But it’s also conveniently located near grocery stores and a short drive to downtown Sarasota and St. Armand’s Circle. Most importantly, Travis was extremely responsive and helpful in answering our many questions.
Stayed 6 nights in Dec 2022

10/10

This is a great place to stay and I can't recommend it highly enough. Spotlessly clean, in a very quiet and peaceful location. We especially enjoyed the rooftop terrace at night overlooking the water and the reflection of lights. The pool was so relaxing with loungers on the sun shelf. This home is fully equipped with everything. We opted for the golf cart option which made our stay even more enjoyable. The host was great with communication, super quick with responses. If you are looking for a quiet getaway with some amazing views this is a great place to stay! The next time we vacation on Siesta Key we will definitely stay here again.
Stayed 2 nights in Aug 2022

10/10

This home is beautiful and immaculately maintained. Travis was a dream to work with and his team was super responsive and very professional. We LOVED the house! The house was big enough to accommodate spouses and children. The house is very comfortable and set up perfectly. And the golf cart and bicycles were icing on the cake! The location can't be beat...it's one of the nicest spots in all of Sarasota. It is 100% worth it. We will definitely be back!
Stayed 7 nights in Nov 2022

10/10

Having grown up in Siesta Key I know the area very well. My family and I came down to 891 Freeling and the accommodations were above and beyond. The home is spectacular with more than enough room for large family and friends and the rooms are gorgeous with more than enough room in all of them. Sitting on a very spacious pool and hot tub with more than enough outside sitting room it is the ultimate retreat. On top of this you have a dock with kayaks and paddle boards to get excessive and enjoy everything the ocean had to offer! Travis and his team were very easy to reach with snag questions and this has been one of the best family experiences we have had. This is the SPOT!
Stayed 5 nights in May 2022

10/10

The photos do not do this property justice, it is even more beautiful in person. The views of the bay are incredible, the house is immaculate and well appointed with everything you might need. Including baby gear like a pack n play and high chair. The neighborhood is quiet and comfortable. The location is a short drive to the beach and super close to the bridge that connects you to the main part of Sarasota. Communication with the property manager/owner was excellent from beginning to end. We always had quick responses to our messages and phone calls and found the entire process seamless. We will definitely come back to this property again! We loved it.
Stayed 7 nights in Jul 2023

10/10

We had an absolute wonderful time at 'The Lookout' As a family we have stayed in some really nice houses all over Florida on vacation. I think the way my 15 year old son summed up our stay here was very appropriate: "Best house we have ever stayed in......'
Stayed 15 nights in Jul 2023

8/10

The stay was great except for a few maintenance issues. First floor master water too hot in shower and had to shower in another room. Lights out in refrigerator and a bedroom. Beautiful home and fits our family well. This is our second year renting. Also, no garage door opener
Stayed 7 nights in Apr 2023

10/10

Will return for sure!
Stayed 6 nights in Nov 2022

10/10

This house and location were perfect. The kitchen was fully stocked and very spacious. We enjoyed sitting on the porches and watching movies on a rainy day in the media/bar room. Travis was easy to communicate with and made check in and out very simple.
Stayed 7 nights in Nov 2022

10/10

We had an excellent week at this beautiful home. There was plenty of space for multiple families in this clean and beautifully furnished home. It had everything we needed for a comfortable stay, plus a golf cart, kayaks, life jackets, and beach chairs and toys. It was a quick golf cart ride to the beach and village. We loved the pool and spa plus the gorgeous water views. The owner was very responsive and easy to work with. We can’t wait to stay there again on our next trip to Siesta Key.
Stayed 1 night in May 2022

10/10

This spacious home was very cozy and had many peaceful and serene views of the water with several places indoors and outdoors to gather as a group or to sit quietly and reflect. We spent quiet mornings watching the sun rise up on the third floor crows nest, and had pleasant evenings watching the sun go down. This lovely home is minutes from the white, sandy, world famous beaches of Siesta Key and the Siesta Key Village, which has many different dining and shopping offerings. The home is also located miles from downtown Sarasota, if you are up for seeing the local arts and shops. We enjoyed kayaking, paddle boarding, and fishing every day on the water as well as lounging by the poolside. The pool table, skee ball table, and movie room were great for indoor recreation. The rooms are all wonderfully appointed with everything you need to relax in comfort in this home away from home. The kitchen has so many fabulous amenities and provided a comfortable space for family dinners and entertaining friends and guests alike. Our family enjoyed this retreat and left feeling relaxed and refreshed after our stay.
Stayed 5 nights in Mar 2022