Entire home

The Lookout - 891 “Siesta Key’

Photo gallery for The Lookout - 891 “Siesta Key’

A swimming pool with lounge chairs, a dock with boats, and a view of the water and buildings.
A swimming pool with lounge chairs, a staircase, and a balcony with outdoor furniture.
A pool area with lounge chairs, a covered deck, and a two-story building with balconies.
A two-story house with a balcony, a wooden dock leading to the water, and palm trees.
A waterfront property with a dock, houses, and a large building with a white facade.

Reviews

10 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • On the beach
    A rare beachfront property in the area - enjoy direct access to the sand and sea.
5 bedrooms6+ bathroomsSleeps 10

Popular amenities

  • On beach
  • Private pool
  • Hot tub on site
  • Garage parking available
  • Dog-friendly
  • Kitchen

Explore the area

View in a map
Siesta Key, FL
  • Place, Shell Beach
    ‪20 min walk‬
  • Place, St. Armands Circle
    ‪17 min drive‬
  • Place, Lido Beach
    ‪18 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪22 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

2nd Floor Bedroom #1

1 King Bed

2nd Floor Bedroom #2

1 King Bed

Bonus Room

1 Double Sofa Bed

Downstairs Master Bedroom

1 King Bed

Kids Bunk Room

1 Single Bed and 1 Single Bunk Bed

Upstairs Master Bedroom

1 King Bed

6 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Bathroom 6

Bathroom 7

Spaces

Deck or patio
Kitchen
Balcony
Garden

About this property

The Lookout - 891 “Siesta Key’

This waterfront palace sits on sailboat water on a peninsula of pure luxury, where you can enjoy sunsets from your own private pool area or a terrace on one of three levels. With 6,300 sq ft of space to entertain, you can enjoy privacy even with large families. Have a cookout at the outdoor grill while enjoying the pool and hot tub. Each of the 3 levels include an outdoor patio that is cozy and inviting with a fire pit on the 1st and fireplace on the 2nd floors. This rental comes with a 6 person lithium powered, street legal golf cart, curtesy of The Toy Barn. It is available for a discounted rate of $250 per week. (This cart normally rents for $650-$1,000 depending on the time of year) Also notable is a game room with pool and skee-ball tables, roof top crows nest, and full bar/movie room - it doesn't get better than this. Located at the North end of the key, this provides for fighting the least amount of traffic - take a golf cart ride to The Village or world famous Siesta Beach; drive/bike over the North bridge to key places like Southside Village, Selby Gardens, UTC and downtown…the opportunities are endless. Your paradise is closer than you think, we look forward to having you as a guest!

www.nextdestinationparadise.com

VR Certificate: VR22-00113

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit 3 pets total)
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 2694152vb
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
On-site 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

About the area

Siesta Key

Located in Bay Island, a neighbourhood in Siesta Key, this holiday home is next to a golf course and on the beach. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Mote Marine Laboratory & Aquarium and Coconuts Family Entertainment Center are also worth visiting.
View more Holiday homes in Siesta KeyOpens in a new window
Map
Siesta Key, FL

What's nearby

  • Shell Beach - 20 min walk - 1.7 km
  • St. Armands Circle - 17 min drive - 12.2 km
  • Lido Beach - 18 min drive - 13.2 km
  • Mote Marine Laboratory & Aquarium - 20 min drive - 14.9 km
  • Mall at University Town Center - 26 min drive - 20.2 km

Getting around

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

Restaurants

  • ‪Walt's Fish Market - ‬5 min drive
  • ‪CinéBistro - ‬5 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Connors - ‬4 min drive
  • ‪Einstein Bros. Bagels - ‬5 min drive

Frequently asked questions

Does The Lookout - 891 “Siesta Key’ have a pool?

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

Is The Lookout - 891 “Siesta Key’ pet-friendly?

Yes, this property allows dogs (limit 3 total) with a maximum weight of up to 23 kg per pet.

How much is parking at The Lookout - 891 “Siesta Key’?

On-site parking is available at the property.

What time is check-in at The Lookout - 891 “Siesta Key’?

Check-in begins at 4:00 PM.

What time is check-out at The Lookout - 891 “Siesta Key’?

Checkout is at 10:00 AM.

Where is The Lookout - 891 “Siesta Key’ located?

Located in Bay Island, this beachfront holiday home is in the city centre, 0.9 mi (1.5 km) from Shell Beach and 2.8 mi (4.4 km) from Siesta Key Beach. Irma Beach and Coconuts Family Entertainment Center are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 27 out of 29 reviews
Rating 8 - Good. 2 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

kellie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great experience in this home. Great amenities available. The house was very clean and well kept up. The neighborhood was very nice and safe. Management was great at communicating when we had a question or was unsure of somthing.5 star rating!
Stayed 7 nights in Feb 2026
Response from VrboOwner on 16 Mar, 2026
Thank you for the wonderful review Kellie. We are so happy you enjoyed your experience and hope to see you again soon!
Verified

10/10 Excellent

Robin M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay for my wife’s special birthday. Whole family joined us. Spacious and very clean. Children loved the pool. Dolphins came right up to the dock. Amazing. Having four grandkids between 2 and 10 the top bunk bed was not suitable for the 10 year old, a bit flimsy. Twin beds would have been better. Host was very responsive and helpful.
Stayed 7 nights in Apr 2026
Response from VrboOwner on 28 Apr, 2026
Thank you for your kind words, Robin. It was our pleasure to have you and your family here!
Verified

10/10 Excellent

Joanne F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Thanksgiving Stay

Very nice property’s
Stayed 10 nights in Nov 2023
Response from VrboOwner on 30 Nov, 2023
Thank you for making The Lookout the destination for your family for Thanksgiving!
Verified

10/10 Excellent

lisa b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is an excellent location to stay, if you enjoy boating around the Sarasota area- plenty of water at low tide, extremely large dock with power and water, it couldn’t be more accommodating! The home is lovely, comfortable and spacious, central to all the area amenities. The owner immediately attends to any needs, in order to make your stay a great one! We spent a month, coming and going with our 40 foot boat every day, and it worked out perfectly. We will certainly be back, it was a great time. In a great place!
Stayed 33 nights in Oct 2025
Verified

10/10 Excellent

Rita G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful oasis

Beautiful home, spacious and perfect location!!!
Stayed 4 nights in Mar 2023
Response from VrboOwner on 22 Jun, 2023
Rita, you were one of the best guests that we’ve ever had! You are welcome here anytime!
Verified

10/10 Excellent

Shelton G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Summer Vacation

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

10/10 Excellent

Megan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Stayed 6 nights in Mar 2023
Response from VrboOwner on 22 Jun, 2023
Megan, you were an amazing renter and we loved having you! Thanks!
Verified

10/10 Excellent

Michael O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome!!

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

10/10 Excellent

Molly H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house!

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
Response from VrboOwner on 22 Jun, 2023
Thank you for staying with us!
Verified

10/10 Excellent

Audra G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 5 nights in May 2022
Response from VrboOwner on 22 Jun, 2023
Audra, we enjoyed having you and your family as guests!
Verified

10/10 Excellent

Amy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ultimate Home and location

Wonderful home, area, great even when it storms so much inside to entertain! Elevator for parents who can’t do stairs! My only regret is I did not rent a small boat. I will do that next time! Beautiful architecture and decor.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

timothy h.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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......'
Stayed 15 nights in Jul 2023
Verified

10/10 Excellent

Timothy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 3 nights in Sep 2022
Response from VrboOwner on 22 Jun, 2023
Thanks Timothy! We look forward to seeing you again.
Verified

10/10 Excellent

Kim K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 7 nights in Mar 2025
Response from VrboOwner on 20 Mar, 2025
Thank you so much for your wonderful response, Kim! We are thrilled to hear that you had such an amazing experience and truly appreciate your recommendation. We would love to welcome you back anytime. Looking forward to your next visit!
Verified

10/10 Excellent

Heather A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 7 nights in Nov 2022
Response from VrboOwner on 22 Jun, 2023
Thanks Heather! We love that your family got that time together.
Verified

10/10 Excellent

Keith S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 5 nights in Aug 2022
Response from VrboOwner on 22 Jun, 2023
Keith, we loved having you as a guest and appreciate your kind words. We look forward to accommodating your next day with us. Thanks again!
Verified

10/10 Excellent

Mary Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Stayed 5 nights in May 2024
Verified

10/10 Excellent

Brett H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 6 nights in Dec 2022
Response from VrboOwner on 22 Jun, 2023
Brett, we loved having your family stay and look forward to next time! Thanks!
Verified

10/10 Excellent

Melissa A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 2 nights in Aug 2022
Response from VrboOwner on 22 Jun, 2023
Thanks for staying with us Melissa! We loved having you as our guest!
Verified

10/10 Excellent

Alex M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 7 nights in Nov 2022
Response from VrboOwner on 22 Jun, 2023
Thanks Alex! We loved having your family as guests. Family time is important to you and that clearly showed through!
Verified

8/10 Good

Alec M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were there when it was unusually cold, so only used the spa once. We had issues with the spa heater, but it was addressed within 24 hrs.Three bathrooms needed to have lightbulbs changed, which was done in a timely manner.Hot water in the kitchen and bathrooms took a very long time to reach the faucets and on one occasion hot water ran out after a bath and a shower (there were 5 of us).The location was terrific, just over the north bridge onto the key, so we avoided a lot of traffic. It’s a great house for a larger group (or the five of us to have private rooms and baths). Upstairs rooms were not as clean as the main floor.Dolphins put on quite a show, as did the cormorants and pelicans. Can’t say enough about the location!In better weather, several outdoor seating/dining areas are available. We really enjoyed the fire pit, tho noted the upholstery could stand an update. Recommendations: do fairly regular property reviews to stay ahead of maintenance. Provide more towels and washcloths, assuming most people use more than 1 washcloth/week.
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Frank F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 5 nights in May 2022
Response from VrboOwner on 22 Jun, 2023
Frank, Thank you for your review! We are so glad that you had a great time at The Lookout! We look forward to seeing you again!
Verified

8/10 Good

Dennis M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Stayed 7 nights in Apr 2023
Response from VrboOwner on 22 Jun, 2023
Dennis, the shower was an easy fix. Obviously light bulbs go out and are able to be replaced, and the garage door openers were located in the top drawer where they belong. All of these items would have been solved with a 3 minute phone call. We can’t guarantee a light bulb won’t go out, but we promise we will be on top of that for any guest that wants to call us to report such issues!
Verified

10/10 Excellent

Patricia J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 7 nights in Jul 2023
Response from VrboOwner on 11 Aug, 2023
Thanks Patricia! We loved having you as guests and would love to host you in the future as well!
Verified

10/10 Excellent

Chad B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great spot. Meet all our expectations.

Will return for sure!
Stayed 6 nights in Nov 2022
Response from VrboOwner on 22 Jun, 2023
Thanks Chad. We look forward to having you back!

About the host

Hosted by Destination Paradise - SRQ

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