Siesta Key, FL

Ocean Overlook

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18 guests
8 bedrooms
10 bathrooms
4681 sqft

Ocean Overlook by Siesta Key Luxury Rental Properties

  • Ocean view
  • Hot tub
  • Game Room
18 guests
8 bedrooms
10 bathrooms
4681 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • Easy cancellation


About this property

Ocean Overlook by Siesta Key Luxury Rental Properties Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! Your dream beach vacation awaits at Ocean Overlook! This four-story home (with an elevator to all levels) is just one house from the sparkling Gulf of Mexico beach! With eight bedrooms and eight full baths, two half baths, and an amazing backyard filled with entertainment, this is the perfect beach home for large groups. Whether it’s soaking up the beach views, enjoying the home’s amenities, or exploring nearby shops and restaurants – this is the place to be! Highlights • One house from the beach • Private pool with in-ground spa • Balconies with Gulf views • Game room • Outdoor entertainment space The main living floor features wide open Gulf views, a fully equipped luxury kitchen with high-end appliances and bar top seating, a formal dining room table, and a seating area with a Smart TV. The balcony is where you’ll want to be! It exudes breathtaking beach views and two outdoor dining tables for ultimate al fresco dining. The club room on the third floor has a wet bar and bar top seating, a living area, a TV, a Foosball Table, Gaming Systems (Nintendo and PS4), and balcony access with views of the Gulf. Ocean Overlook offers six spacious bedrooms, each suitable as a primary suite, featuring plush King beds, ample closet space, and luxurious ensuite bathrooms. Some even boast private balconies for a serene retreat. The Queen and Bunk bedrooms feature adorable ensuite bathrooms with shower and tub combos. Additionally, two half baths and laundry facilities ensure convenience and comfort throughout your stay. Room Details -Primary Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with double vanity and walk-in shower -Second Bedroom, 3rd floor: King bed and ensuite bathroom with double vanity and walk-in shower and soaking tub -Third Bedroom, 3rd floor: King bed and ensuite bathroom with walk-in shower -Fourth Bedroom, 2nd floor: King bed and ensuite bathroom with walk-in shower -Fifth Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with double vanity and walk-in shower -Sixth Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with walk-in shower -Seventh Bedroom, 2nd floor: Queen bed and ensuite bathroom with shower and tub combo -Eighth Bedroom, 2nd floor: Full over Full bunk and ensuite bathroom with shower and tub combo Craft timeless memories in the backyard oasis, with a pool equipped with lush landscaping, tranquil water features, and a spa. On the opposite end, an impressive outdoor BBQ setup with a grill and island, complete with a built-in fridge, awaits culinary delights. Adjacent are two dining tables for al fresco feasts, alongside provided beach chairs and an outdoor shower. At Ocean Overlook, we ensure every moment is spent in luxury and comfort. - 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.

Ocean Overlook by Siesta Key Luxury Rental Properties Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! Your dream beach vacation awaits at Ocean Overlook! This four-story home (with an elevator to all levels) is just one house from the sparkling Gulf of Mexico beach! With eight bedrooms and eight full baths, two half baths, and an amazing backyard filled with entertainment, this is the perfect beach home for large groups. Whether it’s soaking up the beach views, enjoying the home’s amenities, or exploring nearby shops and restaurants – this is the place to be! Highlights • One house from the beach • Private pool with in-ground spa • Balconies with Gulf views • Game room • Outdoor entertainment space The main living floor features wide open Gulf views, a fully equipped luxury kitchen with high-end appliances and bar top seating, a formal dining room table, and a seating area with a Smart TV. The balcony is where you’ll want to be! It exudes breathtaking beach views and two outdoor dining tables for ultimate al fresco dining. The club room on the third floor has a wet bar and bar top seating, a living area, a TV, a Foosball Table, Gaming Systems (Nintendo and PS4), and balcony access with views of the Gulf. Ocean Overlook offers six spacious bedrooms, each suitable as a primary suite, featuring plush King beds, ample closet space, and luxurious ensuite bathrooms. Some even boast private balconies for a serene retreat. The Queen and Bunk bedrooms feature adorable ensuite bathrooms with shower and tub combos. Additionally, two half baths and laundry facilities ensure convenience and comfort throughout your stay. Room Details -Primary Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with double vanity and walk-in shower -Second Bedroom, 3rd floor: King bed and ensuite bathroom with double vanity and walk-in shower and soaking tub -Third Bedroom, 3rd floor: King bed and ensuite bathroom with walk-in shower -Fourth Bedroom, 2nd floor: King bed and ensuite bathroom with walk-in shower -Fifth Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with double vanity and walk-in shower -Sixth Bedroom, 2nd floor: King bed, balcony, and ensuite bathroom with walk-in shower -Seventh Bedroom, 2nd floor: Queen bed and ensuite bathroom with shower and tub combo -Eighth Bedroom, 2nd floor: Full over Full bunk and ensuite bathroom with shower and tub combo Craft timeless memories in the backyard oasis, with a pool equipped with lush landscaping, tranquil water features, and a spa. On the opposite end, an impressive outdoor BBQ setup with a grill and island, complete with a built-in fridge, awaits culinary delights. Adjacent are two dining tables for al fresco feasts, alongside provided beach chairs and an outdoor shower. At Ocean Overlook, we ensure every moment is spent in luxury and comfort. - 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.

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Apr 19, 2026$982.62Available2
Apr 20, 2026$978.50Available2
Apr 21, 2026$978.50Available2
Apr 22, 2026$978.50Not Available2
Apr 23, 2026$978.50Not Available2
Apr 24, 2026$1,361.66Not Available2
Apr 25, 2026$1,306.04Not Available2
Apr 26, 2026$1,119.61Available2
Apr 27, 2026$1,066.05Available2
Apr 28, 2026$1,038.24Available2
Apr 29, 2026$1,033.09Available2
Apr 30, 2026$1,066.05Available2
May 1, 2026$1,616.07Not Available2
May 2, 2026$1,573.84Not Available2
May 3, 2026$1,623.28Not Available3
May 4, 2026$1,189.65Not Available3
May 5, 2026$1,179.35Not Available3
May 6, 2026$1,194.80Not Available3
May 7, 2026$1,498.65Not Available3
May 8, 2026$1,859.15Not Available3
May 9, 2026$1,854Not Available3
May 10, 2026$1,940.52Available3
May 11, 2026$1,180.38Available3
May 12, 2026$1,177.29Available3
May 13, 2026$1,197.89Available3
May 14, 2026$1,256.60Available3
May 15, 2026$1,448.18Not Available3
May 16, 2026$1,456.42Not Available3
May 17, 2026$1,245.27Not Available3
May 18, 2026$1,216.43Not Available3
May 19, 2026$1,401.83Available3
May 20, 2026$1,438.91Available3
May 21, 2026$3,254.80Available3
May 22, 2026$3,986.10Available3
May 23, 2026$3,986.10Available3
May 24, 2026$3,979.92Available3
May 25, 2026$1,342.09Not Available3
May 26, 2026$1,351.36Not Available3
May 27, 2026$1,268.96Not Available3
May 28, 2026$1,362.69Not Available4
May 29, 2026$1,402.86Not Available4
May 30, 2026$1,436.85Not Available4
May 31, 2026$1,345.18Not Available4
Jun 1, 2026$1,880.78Not Available3
Jun 2, 2026$2,391.66Available3
Jun 3, 2026$2,396.81Available3
Jun 4, 2026$2,416.38Available4
Jun 5, 2026$2,425.65Available4
Jun 6, 2026$3,226.99Not Available4
Jun 7, 2026$2,031.16Not Available4
Jun 8, 2026$1,985.84Not Available3
Jun 9, 2026$1,964.21Not Available3
Jun 10, 2026$2,010.56Not Available3
Jun 11, 2026$2,107.38Not Available4
Jun 12, 2026$2,209.35Not Available4
Jun 13, 2026$2,566.76Not Available4
Jun 14, 2026$2,419.47Not Available4
Jun 15, 2026$2,342.22Not Available3
Jun 16, 2026$2,400.93Not Available3
Jun 17, 2026$2,429.77Not Available3
Jun 18, 2026$2,483.33Not Available4
Jun 19, 2026$2,596.63Not Available4
Jun 20, 2026$2,481.27Not Available4
Jun 21, 2026$2,344.28Not Available4
Jun 22, 2026$2,275.27Not Available3
Jun 23, 2026$2,302.05Not Available3
Jun 24, 2026$2,282.48Not Available3
Jun 25, 2026$2,431.83Not Available4
Jun 26, 2026$2,525.56Not Available4
Jun 27, 2026$2,326.77Available5
Jun 28, 2026$2,267.03Available5
Jun 29, 2026$2,241.28Available5
Jun 30, 2026$2,257.76Available5
Jul 1, 2026$2,248.49Available5
Jul 2, 2026$2,984.94Available5
Jul 3, 2026$2,984.94Available5
Jul 4, 2026$3,127.08Not Available4
Jul 5, 2026$2,308.23Not Available4
Jul 6, 2026$2,032.19Not Available3
Jul 7, 2026$1,954.94Not Available3
Jul 8, 2026$1,943.61Not Available3
Jul 9, 2026$2,030.13Not Available4
Jul 10, 2026$2,074.42Not Available4
Jul 11, 2026$2,063.09Available4
Jul 12, 2026$2,062.06Not Available4
Jul 13, 2026$2,062.06Not Available3
Jul 14, 2026$2,062.06Not Available3
Jul 15, 2026$2,062.06Not Available3
Jul 16, 2026$2,062.06Not Available4
Jul 17, 2026$2,062.06Not Available4
Jul 18, 2026$1,838.55Not Available4

Top notch amenities

GUEST FAVORITES

Ocean view
Beach access
Rooftop
Pool outdoor
Hot tub
Game Room
Patio
Balcony
Elevator

Where you'll sleep



Explore Siesta Key, FL

Located just one house from the Gulf on Siesta Key, this home offers immediate access to world-famous white-sand beaches and stunning sunset views. Enjoy nearby Siesta Key Village with its boutiques, restaurants, and nightlife, plus easy access to waterfront dining, boating, and downtown Sarasota’s arts and cultural attractions.

Things to know

Here are some things which you should know before booking Ocean Overlook

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
18 guests maximum
Pets not allowed
No smoking - fees will apply
Events not permitted
Commercial photography requires approval

Cancellation policy

This property follows Prime Vacations - Siesta Key’s standard cancellation policy.