Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook

Siesta Key, Florida
$2181 avg/night Minimum Stay 2 Nights
Bed 8

Bed

Bath 9

Bath

Home Private Vacation Home

Property Type

Sleep 18

Max Sleeps

Night 2 nights

Min Stay

Ocean Overlook by Siesta Key Luxury Rental Properties

Ocean Overlook by Siesta Key Luxury Rental Properties is an exceptional eight bedroom, eight bathroom coastal retreat with two additional half baths, thoughtfully designed for large families and large group getaways seeking luxury coastal living. Located just a three-minute walk to Siesta Key Beach, this four-story Siesta Key luxury rental offers sweeping Gulf views, large balconies, and a private outdoor oasis. Guests are also ashort nine-minute walk to Siesta Key Village, where dining, boutiques, and island nightlife await. With an elevator to all levels, multiple living spaces, and parking for up to five vehicles, Ocean Overlook delivers effortless comfort in one of Sarasota’s most desirable beach locations.

Highlights
• 3-minute walk to Siesta Key Beach
• 8 Bedrooms / 8 Full Bathrooms / 2 Half Bathrooms
• 6 King beds, 1 Queen bed, 1 Full over Full bunk bed
• Private pool with in-ground spa
• Balconies with Gulf views
• Game room with foosball and gaming systems
• Elevator for guest use
• Outdoor dining, BBQ grill, and entertainment space
• Beach chairs, wagon, and cooler provided
• Dog Friendly with host approval and additional fee
• Parking for up to 5 vehicles
• 9-minute walk to Siesta Key Village

This Siesta Key vacation home with pool is centered around an inviting backyard retreat designed for relaxation and entertainment. The private pool features tranquil water elements, lush landscaping, and a connected spa, creating a peaceful setting for afternoons in the sun or evenings under the stars. Nearby, the outdoor kitchen and BBQ area includes a grill, island with built in refrigerator, and multiple dining tables, making it easy to gather for casual meals or celebratory dinners. A shaded outdoor dining bar with seating and a TV adds another layer of comfort, while the outdoor shower and provided beach gear make transitioning from the Gulf to the pool seamless.

The main living level showcases a bright, open concept design with expansive windows framing Gulf views. A spacious living area with comfortable seating and a large TV flows into a fully equipped gourmet kitchen featuring high end appliances, generous counter space, and bar top seating ideal for group cooking and conversation. The formal dining table comfortably accommodates large meals together. Step onto the balcony to enjoy ocean breezes and dine outdoors with stunning views of the Gulf. On the third floor, the game room offers an additional gathering space complete with a wet bar, bar seating, a living area, and a TV. Entertainment continues with a foosball table, PlayStation, and vintage Nintendo console, plus balcony access.

Ocean Overlook offers a collection of thoughtfully designed bedrooms, many functioning as private primary style suites. King bedrooms feature plush bedding, ample closet space, and elegant ensuite bathrooms with walk-in showers, double vanities, and select soaking tubs. Several suites include private balconies, offering quiet spaces to unwind with Gulf views. The Queen bedroom and bunk bedroom each include charming ensuite bathrooms with shower and tub combinations, ideal for families traveling together. Two half baths and conveniently located laundry facilities enhance comfort throughout the home.

Room Details
• Primary Bedroom (3rd Floor): King bed, balcony, ensuite bathroom with double vanity and walk-in shower
• Second Bedroom (3rd Floor): King bed, ensuite bathroom with double vanity, walk-in shower, and soaking tub
• Third Bedroom (3rd Floor): King bed, ensuite bathroom with walk-in shower
• Fourth Bedroom (2nd Floor): King bed, ensuite bathroom with walk-in shower
• Fifth Bedroom (2nd Floor): King bed, balcony, ensuite bathroom with double vanity and walk-in shower
• Sixth Bedroom (2nd Floor): King bed, balcony, ensuite bathroom with walk-in shower
• Seventh Bedroom (2nd Floor): Queen bed, ensuite bathroom with shower and tub combo
• Eighth Bedroom (2nd Floor): Full-over-Full bunk bed, ensuite bathroom with shower and tub combo

Ocean Overlook is ideally positioned along Beach Road, placing guests just minutes from Siesta Key Beach and within a short nine minute walk to Siesta Key Village, home to popular restaurants, beach bars, and boutique shopping. This Siesta Key vacation rental includes an in-home washer and dryer, elevator access to all levels, and parking for up to five vehicles, making extended stays and large group travel effortless.

From sunrise coffee overlooking the Gulf to evenings spent poolside with family and friends, Ocean Overlook by Siesta Key Luxury Rental Properties offers an elevated beach getaway designed for unforgettable moments. With walkable beach access, luxurious indoor and outdoor spaces, and proximity to Siesta Key Village, this home delivers the perfect balance of relaxation and island adventure. Book your stay at Ocean Overlook today and experience the best of Siesta Key luxury living!

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With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details.

5 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

Please see our Siesta Key Luxury Rental Properties Rental Policies for full details.

This home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.

Please Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • BEACH

    On The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    8 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 4681 Sq Ft (435 Sq M)
  • KITCHEN

    Cookware/dishes/utensils Dishwasher Ice Maker Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Fenced Yard
  • POOL/SPA

    Heated Pool Hot Tub Private Pool
  • BATHROOMS

    9 Bathrooms Hair Dryer Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Kayaking Nearby Marina Nearby Parasailing Nearby Power Boating Nearby Sailing Nearby Swimming Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Arcade/game Room Foosball Table Games Video Games Smart TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near A Hospital Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Elevator Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 18

Map Map

School District Rates & Availability

Review Review

  • Laura M.

    Submitted Feb 1, 2026

    Stayed Jan 29, 2026

    Beautiful home! Amazing location! Super quick to answer our questions and respond to any concerns.

  • Jen P.

    Submitted Jan 27, 2026

    Stayed Jan 22, 2026

    Host was very welcoming. Just had to send a text asking for the entrance code. Other than that, they were very responsive. House was ready for us!

  • Robyn

    Submitted Sep 22, 2025

    Stayed Sep 19, 2025

    The property was exactly as advertised, and communication with the host was always efficient and timely. The space was very accommodating for our large family, and the location couldn’t have been more perfect. We didn’t want for anything during our stay—it had everything we needed. Highly recommend! As we will be planning a future stay.

  • William M.

    Submitted Aug 19, 2025

    Stayed Aug 13, 2025

    Four floors, great vistas and a fantastic pool.Not to mention, all that you need to take out to the beach is is there for you, with plenty of towels, chairs and a pull cart to get to the beach(which all looked brand new).Everything was very high end in and around the whole house.Everywhere to eat and drink were all walkable.

  • Maria Arlen D.

    Submitted Aug 18, 2025

    Stayed Aug 2, 2025

    Our family had a wonderful time. The house is beautiful with a great view of the water. Very spacious. Plenty of bathrooms. But we would have appreciated if the bathrooms had handicapped accessibility features like handle bars. The elevator was great; but it broke 3 times. Thankfully, nobody got stuck in the elevator and the maintenance guy came very quickly each time. He was very pleasant and professional. We also would have appreciated potholders and additional hand towels in the kitchen. Since we had a baby with us, we were very particular about clean floors. We couldn’t find a mop to clean. We ended up buying a swiffer and left it there. Lastly, we loved the pool; but didn’t enjoy it very much because there were tons of mosquitoes. We bought some citronella; but not enough to drive away the mosquitoes. (The mosquitoes might have come from the swimming pool next door which was green and cloudy). All in all, we enjoyed our stay. It was so nice to be in one house where we gathered together when we wanted to, but kept our private spaces when we wanted some quiet time. Thank you for sharing your home with us.

  • Justin O.

    Submitted Jun 27, 2025

    Stayed Jun 19, 2025

    Tremendous property!! Beautiful views of the Gulf. Easily walkable to the beach. Large, spacious house. Great for big families!!!

  • Bryan O.

    Submitted May 27, 2025

    Stayed May 22, 2025

    The home was in great shape with a beautiful pool and view. The rooms and beds were all very nice and the porcess from start to finish was easy

  • Art M.

    Submitted Aug 27, 2024

    Stayed Aug 11, 2024

    We had a terrific vacation.the location is ideal and the space is plentiful. All technology was functioning and easy to use. Beach is close and only a short walk as is restaurants and shops. This home could easily house 2 families with 2-3 kids each.

  • silvia r.

    Submitted Aug 13, 2023

    Stayed Aug 11, 2023

    The TV in the pool did not worked and de AC in the 4th floor was so slow. the rest, perfect and amazing views.

  • Angie S.

    Submitted Jul 15, 2023

    Stayed Jul 9, 2023

    The house was very comfortable- nothing too fancy but very clean and perfect for our multi family vacation. The pool was fantastic- plenty of space in the sun and the shade. The location was great- 5 to 10 minute walk into town. Tons of restaurants and shops. Things seem to close down around 10pm and the streets are pretty quiet after that. The house is located right on the street so we were a little worried about traffic noise at night but it was very quiet. Every bedroom having its own bathroom was so nice. There are 2 washing machines and 2 dryers which came in very handy. The beach access is super close but the walk from the beach access point to the beach is very long. 2 beach wagons are provided but they don’t work very well because the sand isn’t compacted. The extra refrigerator on the ground level was very nice. We had a great vacation!

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Total

Includes taxes and fees
$2,181+
View details