Located in Bay Island within a mile (2 km) of Shell Beach, this vacation home is within 2 miles (3 km) of Irma Beach. The vacation home includes a private pool, a kitchen, and a fireplace.
Sarasota Memorial Hospital - 5 min drive - 2.8 miles
Siesta Key Beach - 7 min drive - 2.8 miles
Marina Jack - 9 min drive - 4.5 miles
St. Armands Circle - 14 min drive - 7.4 miles
Lido Beach - 17 min drive - 8.7 miles
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
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)
The vacation home is air-conditioned and features a kitchen, 6.5 bathrooms, and a balcony, and there's space to spread out with 5 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a private pool, a washing machine, and a fireplace.
Property manager
Destination Paradise - SRQ
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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
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
This property welcomes pets
Dogs only
3 total (50 lbs is the maximum weight per pet)
Service animals exempt from fees
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
Check-in: 4:00 PM
Check-out: 10:00 AM
Minimum check-in age: 25
We should mention
Details about charges, deposits, or other important information:
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Property is also known as
5
Frequently asked questions
What is there to do close to this vacation home?
This vacation home is situated in Bay Island within a short 18-minute walk of Shell Beach. You'll also find Siesta Key Beach and Crescent Beach within a short drive.
Will I be able to park at this vacation home?
Yes, there is a garage.
Is this vacation home next to a casino?
No, this vacation home is not connected to a casino.
Is there an indoor pool at this vacation home?
No, this vacation home doesn't have an indoor pool; however, there is a hot tub.
Is AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool a good place to stay for couples?
At this beachfront vacation home, there are many amenities for couples, including a private pool and a fireplace in each accommodation with some featuring ocean views.
Does AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool have a hot tub?
Yes, this vacation home has a spa tub.
Does this vacation home provide breakfast?
No, this vacation home doesn't offer breakfast.
Does this vacation home allow pets to stay for free?
Although dogs can't stay for free, they are welcome at this vacation home.
Are there connecting rooms at this vacation home?
No, there aren't connecting rooms at this vacation home.
What is the closest airport to this vacation home?
The closest major airport to this vacation home is Sarasota-Bradenton Intl. Airport (SRQ), which is 8.4 mi away (25 minutes by car).
Are there rooms with balconies at AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool?
Yes, every accommodation at AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool comes with a balcony with some featuring ocean views.
AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 21 out of 22 reviews
10 - Excellent
21
Rating 8 - Good. 1 out of 22 reviews
8 - Good
1
Rating 6 - Okay. 0 out of 22 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 22 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 22 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Kim K.
Mar 9, 2025
Liked: Cleanliness
Exceed all expectations.
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.
Kim K.
Stayed 7 nights in Mar 2025
10/10 Excellent
Shelton G.
Jun 24, 2024
Liked: Cleanliness
Summer Vacation
Amazing property with plenty of space for large families.
Shelton G.
Stayed 7 nights in Jun 2024
10/10 Excellent
Mary Z.
Jun 2, 2024
Liked: Cleanliness
Amazing
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
Mary Z.
Stayed 5 nights in May 2024
10/10 Excellent
Michael O.
May 14, 2024
Liked: Cleanliness
Awesome!!
The house was great. Better than the pics and the pics are great.
Michael O.
Stayed 7 nights in May 2024
10/10 Excellent
Joanne F.
Nov 30, 2023
Liked: Cleanliness
Great Thanksgiving Stay
Very nice property’s
Joanne F.
Stayed 10 nights in Nov 2023
10/10 Excellent
timothy h.
Aug 23, 2023
Liked: Cleanliness
Simply Fantastic!
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......'
timothy h.
Stayed 15 nights in Jul 2023
10/10 Excellent
Patricia J.
Jul 31, 2023
Liked: Cleanliness
Spectacular Home!
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.
Patricia J.
Stayed 7 nights in Jul 2023
8/10 Good
Dennis M.
Apr 11, 2023
Liked: Cleanliness
Easter week
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
Dennis M.
Stayed 7 nights in Apr 2023
10/10 Excellent
Megan S.
Apr 5, 2023
Liked: Cleanliness
Absolutely Beautiful Property
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
Megan S.
Stayed 6 nights in Mar 2023
10/10 Excellent
Rita G.
Mar 14, 2023
Liked: Cleanliness
Beautiful oasis
Beautiful home, spacious and perfect location!!!
Rita G.
Stayed 4 nights in Mar 2023
10/10 Excellent
Brett H.
Jan 3, 2023
Liked: Cleanliness
Awesome place!
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.
Brett H.
Stayed 6 nights in Dec 2022
10/10 Excellent
Chad B.
Dec 23, 2022
Liked: Cleanliness
Great spot. Meet all our expectations.
Will return for sure!
Chad B.
Stayed 6 nights in Nov 2022
10/10 Excellent
Alex M.
Dec 7, 2022
Liked: Cleanliness
AMAZING!!!
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!
Alex M.
Stayed 7 nights in Nov 2022
10/10 Excellent
Heather A., Warrenton VA
Nov 25, 2022
Liked: Cleanliness
Better than pictures
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.
Heather A.
Stayed 7 nights in Nov 2022
10/10 Excellent
Timothy M.
Nov 10, 2022
Liked: Cleanliness
Beautiful Location
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.
Timothy M.
Stayed 3 nights in Sep 2022
10/10 Excellent
Melissa A., Sarasota, FL
Sep 2, 2022
Liked: Cleanliness
Private and Peaceful
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.
Melissa A.
Stayed 2 nights in Aug 2022
10/10 Excellent
Keith S.
Aug 29, 2022
Liked: Cleanliness
Siesta Key
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.
Keith S.
Stayed 5 nights in Aug 2022
10/10 Excellent
Molly H., United States
Jul 25, 2022
Liked: Cleanliness
Beautiful house!
Beautiful house and a beautiful setting. Travis, the house manager, was always available for questions and needs.
Would definitely book again.
Molly H.
Stayed 6 nights in Jul 2022
10/10 Excellent
Audra G.
Jun 1, 2022
Liked: Cleanliness
Incredible property for families
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!
Audra G.
Stayed 5 nights in May 2022
10/10 Excellent
Frank F.
May 25, 2022
Liked: Cleanliness
Absolutely top notch
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!
Frank F.
Stayed 5 nights in May 2022
10/10 Excellent
Ashley T.
May 19, 2022
Liked: Cleanliness
Amazing property!!
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.
Ashley T.
Stayed 1 night in May 2022
10/10 Excellent
Candace B.
Mar 18, 2022
Liked: Cleanliness
Fabulous Home!!
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.