House in Sarasota, FL
10 guests · 5 bedrooms · 6 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
KEEP READING BELOW! THIS IS NOT JUST A BASIC DESCRIPTION OF THE HOME AND CONTAINS VERY USEFUL INFORMATION THAT YOU WON’T WANT TO MISS!!
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!
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
***PLEASE NOTE***
COFFEE MAKER: Combo Coffee maker (both drip and K-cups)
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 $35/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. DOGS ONLY. CATS ARE NOT ALLOWED.
The boat dock is not allowed to be used for docking personal or rented boats unless you get approval from management! Using without approval is subject to a minimum $2,500 fine.
A SIGNED DESTINATION PARADISE RENTAL AGREEMENT AND ID WILL BE REQUIRED FOR ALL RESERVATIONS.
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)
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!
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
***PLEASE NOTE***
COFFEE MAKER: Combo Coffee maker (both drip and K-cups)
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 $35/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. DOGS ONLY. CATS ARE NOT ALLOWED.
The boat dock is not allowed to be used for docking personal or rented boats unless you get approval from management! Using without approval is subject to a minimum $2,500 fine.
A SIGNED DESTINATION PARADISE RENTAL AGREEMENT AND ID WILL BE REQUIRED FOR ALL RESERVATIONS.
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)
Amenities at The Lookout - 891 “Siesta Key’
Non-smoking
Pets allowed
Family friendly
Map of Sarasota, FL
Ratings and reviews
10 / 10Outstanding·Apr 2026
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.
10 / 10Outstanding·Mar 2026
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!
8 / 10Excellent·Feb 2026
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.
10 / 10Outstanding·Dec 2025
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!
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Top rated by guests
9.9Outstanding
(29 Ratings)
"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..."
Robin M.Don't miss out! Price and availability may change
