Siesta Key, FL

Ocean Overlook

8 bedrooms 9 beds 10 baths 18 guests

About the 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 4, 2026$2,796.45Not Available2
Apr 5, 2026$2,337.07Not Available2
Apr 6, 2026$2,641.95Not Available2
Apr 7, 2026$2,852.07Not Available2
Apr 8, 2026$2,796.45Not Available2
Apr 9, 2026$2,456.55Not Available2
Apr 10, 2026$3,961.38Not Available2
Apr 11, 2026$2,291.75Not Available2
Apr 12, 2026$1,291.62Not Available2
Apr 13, 2026$1,200.98Not Available2
Apr 14, 2026$1,173.17Not Available2
Apr 15, 2026$1,263.81Not Available2
Apr 16, 2026$1,459.51Not Available2
Apr 17, 2026$2,901.51Not Available3
Apr 18, 2026$2,842.80Available3
Apr 19, 2026$1,726.28Available3
Apr 20, 2026$2,195.96Available3
Apr 21, 2026$2,179.48Available3
Apr 22, 2026$2,864.43Not Available3
Apr 23, 2026$2,989.06Not Available3
Apr 24, 2026$2,866.49Not Available3
Apr 25, 2026$2,600.75Not Available3
Apr 26, 2026$1,811.77Available3
Apr 27, 2026$1,646.97Available3
Apr 28, 2026$1,587.23Available3
Apr 29, 2026$1,633.58Available3
Apr 30, 2026$1,768.51Available3
May 1, 2026$1,919.92Not Available3
May 2, 2026$1,925.07Not Available3
May 3, 2026$1,735.55Not Available4
May 4, 2026$1,344.15Not Available3
May 5, 2026$1,317.37Not Available3
May 6, 2026$1,400.80Not Available3
May 7, 2026$1,592.38Not Available4
May 8, 2026$1,980.69Not Available4
May 9, 2026$1,972.45Not Available4
May 10, 2026$2,091.93Available4
May 11, 2026$1,316.34Available3
May 12, 2026$1,316.34Available3
May 13, 2026$1,369.90Available3
May 14, 2026$1,499.68Available4
May 15, 2026$1,614.01Not Available4
May 16, 2026$1,628.43Not Available4
May 17, 2026$1,279.26Not Available4
May 18, 2026$1,179.35Not Available3
May 19, 2026$1,153.60Available3
May 20, 2026$1,204.07Available3
May 21, 2026$2,796.45Available4
May 22, 2026$3,421.66Available4
May 23, 2026$3,416.51Available4
May 24, 2026$3,413.42Available4
May 25, 2026$1,423.46Not Available3
May 26, 2026$1,430.67Not Available3
May 27, 2026$1,188.62Not Available3
May 28, 2026$1,298.83Not Available4
May 29, 2026$1,389.47Not Available4
May 30, 2026$1,421.40Not Available4
May 31, 2026$1,284.41Not Available4
Jun 1, 2026$1,749.97Not Available3
Jun 2, 2026$2,486.42Available3
Jun 3, 2026$2,486.42Available3
Jun 4, 2026$2,486.42Available4
Jun 5, 2026$2,486.42Available4
Jun 6, 2026$3,420.63Not Available7
Jun 7, 2026$1,933.31Not Available7
Jun 8, 2026$1,783.96Not Available7
Jun 9, 2026$1,742.76Not Available7
Jun 10, 2026$1,816.92Not Available7
Jun 11, 2026$1,994.08Not Available7
Jun 12, 2026$2,148.58Not Available7
Jun 13, 2026$2,504.96Not Available7
Jun 14, 2026$2,255.70Not Available7
Jun 15, 2026$2,079.57Not Available7
Jun 16, 2026$2,125.92Not Available7
Jun 17, 2026$2,131.07Not Available7
Jun 18, 2026$2,344.28Not Available7
Jun 19, 2026$2,544.10Not Available7
Jun 20, 2026$2,460.67Not Available7
Jun 21, 2026$2,223.77Not Available7
Jun 22, 2026$2,050.73Not Available7
Jun 23, 2026$2,078.54Not Available7
Jun 24, 2026$2,091.93Not Available7
Jun 25, 2026$2,297.93Not Available7
Jun 26, 2026$2,510.11Not Available7
Jun 27, 2026$2,279.39Available7
Jun 28, 2026$2,149.61Available7
Jun 29, 2026$1,943.61Available7
Jun 30, 2026$1,897.26Available7
Jul 1, 2026$1,666.54Available7
Jul 2, 2026$2,984.94Available7
Jul 3, 2026$2,984.94Available7

Where you'll sleep

Amenities

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

Where you'll be

Siesta Key, FL, 34242, US

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

Cancellation policy

Cancel within 24 hours for a full refund.
Fair-Refund policy applies after the cancellation deadline.

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 18 guests.