AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool | House in Siesta Key

10.0 (23 Reviews) |   Pet Friendly   5 Bedrooms  6 Bathrooms  10 Guests  Stay&Play
Siesta Key House | AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool

5 Bedroom House in Siesta Key

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!
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“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
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 collect. By making this reservation, you agree to this policy.
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)

AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool is located in Siesta Key. AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool provides accommodation, featuring Ocean View, Fireplace/Heating, Guest Services, among other amenities. This House features Ocean View, Fireplace/Heating, Guest Services, to make your stay a comfortable one.

AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool has 5 Bedrooms , 6 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Siesta Key has interesting places to visit. If you want to learn more about the House in Siesta Key, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • Pool
  • TV
  • View
  • Private Pool
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Guest Services
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Hot Tub
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy 3 total (up to 50 lbs per pet) pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy Smoking is not permitted
Other Policy 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 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 onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Siesta Key, 34242, USA

What Our Guests say 500 + Reviews

Mar 9, 2025 10:22:32 AM
Summary: 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. Kim K.
Jun 24, 2024 09:31:06 PM
Summary: Amazing property with plenty of space for large families.
Shelton G. Shelton G.
Jun 2, 2024 07:20:47 AM
Summary: 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. Mary Z.
May 15, 2024 12:16:28 AM
Summary: The house was great. Better than the pics and the pics are great.
Michael O. Michael O.
Nov 30, 2023 11:12:38 PM
Summary: Very nice property’s
Joanne F. Joanne F.
Aug 23, 2023 10:45:26 PM
Summary: 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. timothy h.
Aug 9, 2023 11:57:45 AM
Summary: 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. Patricia J.
Apr 26, 2023 11:00:45 AM
Summary: 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. Dennis M.
Apr 20, 2023 11:00:57 AM
Summary: 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. Megan S.
Mar 16, 2023 04:31:43 AM
Summary: Beautiful home, spacious and perfect location!!!
Rita G. Rita G.

FAQ's

Is this Siesta Key house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Siesta Key house have a swimming pool?

Yes, this Siesta Key house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Siesta Key house?

Best-rates for the Siesta Key house starts from $1,411 per night with includes Ocean View, Fireplace/Heating, Guest Services, Hot Tub, Internet, Kitchen, Parking, Pool, View, Sports/Activities, Bedding/Linens, Barbecue/Outdoor Cooking, Laundry, Pet Friendly, TV, Balcony/Terrace, Entertainment, Child Friendly, Air Conditioner, Private Pool, Oceanfront, Security/Safety, Wellness Facilities StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Siesta Key house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Siesta Key house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Siesta Key house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Siesta Key house?

Based on the information reported by the owner or manager, the Siesta Key house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Siesta Key house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Siesta Key house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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