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891 - The Lookout

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

Bedrooms: 5

Bathrooms: 6 full, 1 ½-bath

Sleeps: 10

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Overview ↑↓

Premier local manager, Destination Paradise welcomes you to “The Lookout”… a beautiful, grand vacation home on a magnificent waterfront area of the bay with an awesome outdoor lounge and heated pool area! This 4 level home sleeps up to 13. It is located on the ultra-premium North end of the island in a super private neighborhood and is just minutes from world famous Siesta Key Beach and Siesta Key Village.

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!

“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

***PLEASE NOTE***

POOL HEATER RULES:
Pool heat temp is set at 83º and runs each day from 7 AM until 7 PM from October 15-April 15. Outside of these dates, the Florida weather should naturally heat the pool. Pool temps are not guaranteed. This pool is heated by a heat pump and is only capable of heating to around 20-25 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 3 hours, once turned on and can be run at any time and will heat to 100º

PET POLICY: This home has a $25/pet/day fee. Aggressive breeds (ie. pitbulls, etc) may not be allowed and will need to be approved by management prior to your stay. If you bring your pet without claiming them on the reservation or by trying to avoid paying the pet fee, a minimum fine of $500/pet will be collected. By making this reservation, you agree to this policy.

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

Room Details ↑↓

Downstairs Master Bedroom

Downstairs master bedroom with pool/patio access as well as huge , bathroom with spa tub, oversize s

Bed Info: 1 King

Private Bath

2nd Floor Bedroom #1

King size bed with private bath and balcony.

Bed Info: 1 King

Private Bath

2nd Floor Bedroom #2

King size bed with private bath and balcony.

Bed Info: 1 King

Private Bath

Kids Bunk Room

Great bunk room for kids or single adults with an additional pull out trundle bed , Vizio tv , fire

Bed Info: 1 Bunk Bed - (1 Twin)

Private Bath

Upstairs Master Bedroom

Private master bedroom connected to balcony and large bathroom with spa tub, shower, bidet and toile

Bed Info: 1 King

Private Bath

Bonus Room

Pull out couch located off of the upstairs master , bedroom Vizio smart tv

Bed Info: 1 Sleeper Sofa

Amenities ↑↓

Entertainment

Television, Video Games, Pool Table, Stereo, Toys, Books , Game Room, Video Library, Smart TV, DVD Player, Satellite/Cable, Games

Essential Amenities

Wireless Internet, Toilet Paper, Towels Provided, Linens provided, Basic Soaps, Clothes Washer, Clothes Dryer, Hair Dryer, Iron & Board, Air Conditioning: Central Air, Heating

General

Fireplace, Garage, Internet, Living Room, Parking, Paper Towels, Pack n’ Play

Kitchen and dining

Kitchen, Toaster, Blender, Dishwasher, Microwave, Ice Maker, Coffee Maker, Grill, Dining table, Oven, Kitchen island, Stove, Refrigerator, Dishes & Utensils

Location Type

Oceanfront, Beach, Beachfront, Beach View, Downtown, Golf Course, Lake, Lakefront, Lake View, Near Ocean, Ocean View, River, Town, Village, Waterfront, Water View

Office

Desk and Chair

Outdoor Features

Golf on Property, Beach Chairs, Outdoor Furniture, Fire Pit, Balcony, Beach Towels, Kayak/Canoe, Deck/Patio, Lawn/Garden, Porch/Veranda, Bicycles, Water Sports Gear, Boat Slip

Pool and spa facilities

Outdoor Pool, Private Pool, Spa/Hot Tub, Heated Pool, Communal Pool

Safety

Smoke Alarm, Carbon Monoxide Alarm, Fire Extinguisher

System

Pet Friendly

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Area Info ↑↓

Get To Know The Area!: 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)

Reviews ↑↓

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Perfect Vacation Home

Vacation Date: June 1, 2025

"Beautiful spacious home! My kids loved the pool table and Arcade games. 9 of us fit comfortably and all rooms had comfortable beds w/bathrooms. Super clean and well appointed. 10/10 recommend this home for your next vacation.

Reviewed By: AP

Last minute, save!

Vacation Date: April 6, 2025

"This was literally a last-minute rental for us and it turned out to be wonderful. Beautiful home, fantastic location, and awesome weather led to a great week. Thank you.

Reviewed By: Rich

A Wonderful Stay (even if there was a tropical storm)

Vacation Date: August 2, 2024

"The house is wonderful. Pool and property are great. Everything was super clean and comfortable. We had to ride out the storm for a couple of days and we were plenty comfortable. Many wonderful family memories made during this trip.

Reviewed By: Bryan & Stacy

Perfection

Vacation Date: June 21, 2024

"Home was immaculate! Had everything we needed to accommodate our stay. My kids loved all the space, fishing off the docks and watching movies in the super cool tv room. Highly recommend this home. Absolutely stunning and tons of space to enjoy.

Reviewed By: AP

Perfection

Vacation Date: June 21, 2024

Reviewed By: AP

Fantastic Home

Vacation Date: May 4, 2024

"The pictures do not do it justice. The house it awesome with all the amenities. Having the pool right on the water was great. Family used the Kayaks and water boards on the intercostal. We saw dolphins, Manatees, Stingrays and eagles. We fished off the dock. The house itself was amazing.

Reviewed By: MOG

UHHHMAZING!

Vacation Date: January 31, 2024

"This place was absolutely beautiful! Very spacious & tastefully decorated. Great outdoor area to gather. Owner was very responsive. Would definitely stay here again!

Reviewed By: Shannon

Great family getaway…

Vacation Date: February 15, 2024

"We had a wonderful stay at Destination Paradise! The house and property were beautiful and spacious and even better than in photos. We loved it!

Reviewed By: Brynn

Amazing house!!

Vacation Date: March 15, 2024

"This place is absolutely amazing!! great views and close to the beaches, very clean, great host, quiet neighborhood and a very nice kitchen!!

Reviewed By: David

Awesome place!

Vacation Date: December 23, 2022

"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.

Reviewed By: Brett H.

Beautiful Location

Vacation Date: September 7, 2022

"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.

Reviewed By: Timothy M.

Incredible property for families

Vacation Date: May 9, 2022

"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!

Reviewed By: Audra G.

Amazing property!!

Vacation Date: May 1, 2022

"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.

Reviewed By: Ashley T.

Absolutely top notch

Vacation Date: May 9, 2022

"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!

Reviewed By: Frank F.

Private and Peaceful

Vacation Date: August 15, 2022

"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.

Reviewed By: Melissa A.

ABSOLUTELY BEAUTIFUL PROPERTY

Vacation Date: March 19, 2023

"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.

Reviewed By: Megan S.

AMAZING!!!

Vacation Date: November 16, 2022

"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!

Reviewed By: Alex M.