Siesta Key, FL

Ocean Overlook

8 bedrooms 0 beds 10 baths 18 guests New

About the property

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 a short 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! - 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 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 a short 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! - 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

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
May 19, 2026$978.50Not Available2
May 20, 2026$978.50Available2
May 21, 2026$978.50Not Available2
May 22, 2026$1,485.26Not Available2
May 23, 2026$1,575.90Not Available2
May 24, 2026$978.50Available2
May 25, 2026$978.50Not Available2
May 26, 2026$978.50Not Available2
May 27, 2026$978.50Not Available2
May 28, 2026$1,027.94Not Available2
May 29, 2026$1,523.37Not Available2
May 30, 2026$1,521.31Not Available2
May 31, 2026$1,009.40Not Available2
Jun 1, 2026$1,411.10Not Available2
Jun 2, 2026$2,213.47Available3
Jun 3, 2026$2,224.80Available3
Jun 4, 2026$2,289.69Available3
Jun 5, 2026$2,515.26Available3
Jun 6, 2026$3,170.34Not Available3
Jun 7, 2026$1,903.44Not Available3
Jun 8, 2026$1,849.88Not Available3
Jun 9, 2026$1,722.16Not Available3
Jun 10, 2026$1,740.70Not Available3
Jun 11, 2026$1,987.90Not Available3
Jun 12, 2026$2,693.45Not Available3
Jun 13, 2026$3,081.76Not Available3
Jun 14, 2026$2,229.95Not Available3
Jun 15, 2026$2,167.12Not Available3
Jun 16, 2026$1,996.14Not Available3
Jun 17, 2026$2,062.06Not Available3
Jun 18, 2026$2,667.70Not Available3
Jun 19, 2026$3,276.43Not Available3
Jun 20, 2026$3,140.47Not Available3
Jun 21, 2026$2,534.83Not Available3
Jun 22, 2026$2,513.20Not Available3
Jun 23, 2026$2,339.13Not Available3
Jun 24, 2026$2,365.91Not Available3
Jun 25, 2026$2,651.22Not Available3
Jun 26, 2026$3,188.88Not Available3
Jun 27, 2026$2,685.21Available5
Jun 28, 2026$2,418.44Not Available5
Jun 29, 2026$2,381.36Not Available5
Jun 30, 2026$2,230.98Not Available5
Jul 1, 2026$2,179.48Not Available5
Jul 2, 2026$2,878.85Not Available5
Jul 3, 2026$2,944.77Not Available5
Jul 4, 2026$3,092.06Not Available3
Jul 5, 2026$2,372.09Not Available3
Jul 6, 2026$2,137.25Not Available3
Jul 7, 2026$1,929.19Not Available3
Jul 8, 2026$1,930.22Not Available3
Jul 9, 2026$2,145.49Not Available3
Jul 10, 2026$2,619.29Not Available3
Jul 11, 2026$2,597.66Not Available3
Jul 12, 2026$2,120.77Not Available3
Jul 13, 2026$2,057.94Not Available3
Jul 14, 2026$2,041.46Not Available3
Jul 15, 2026$2,043.52Not Available3
Jul 16, 2026$2,136.22Not Available3
Jul 17, 2026$2,618.26Not Available3
Jul 18, 2026$2,378.27Not Available3
Jul 19, 2026$1,896.23Not Available3
Jul 20, 2026$1,859.15Not Available3
Jul 21, 2026$1,728.34Not Available3
Jul 22, 2026$1,748.94Not Available3
Jul 23, 2026$1,968.33Not Available3
Jul 24, 2026$2,371.06Not Available3
Jul 25, 2026$2,325.74Not Available3
Jul 26, 2026$1,872.54Not Available3
Jul 27, 2026$1,811.77Not Available3
Jul 28, 2026$1,649.03Not Available3
Jul 29, 2026$1,642.85Not Available3
Jul 30, 2026$1,797.35Not Available3
Jul 31, 2026$2,167.12Not Available3
Aug 1, 2026$2,229.95Not Available3
Aug 2, 2026$2,229.95Not Available3
Aug 3, 2026$2,229.95Not Available3
Aug 4, 2026$2,229.95Not Available3
Aug 5, 2026$2,229.95Not Available3
Aug 6, 2026$2,229.95Not Available3
Aug 7, 2026$2,229.95Not Available3
Aug 8, 2026$1,961.12Not Available3
Aug 9, 2026$1,551.18Not Available3
Aug 10, 2026$1,139.18Available3
Aug 11, 2026$1,303.98Not Available3
Aug 12, 2026$1,400.80Not Available3
Aug 13, 2026$1,464.66Not Available3
Aug 14, 2026$1,742.76Not Available3
Aug 15, 2026$1,688.17Not Available3
Aug 16, 2026$1,524.40Not Available3
Aug 17, 2026$1,237.03Available3

Where you'll sleep

Amenities

Beachfront
Ocean view
Beach access
Pool outdoor
Hot tub
Game Room
BBQ Area
Patio

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Where you'll be

Siesta Key, FL, 34242, US

From the Tampa Airport: Take I-275 South, Take the US-19 S Exit 5, Take a slight right onto US Highway 41, Stay straight on US-301 S, Turn Right onto Siesta Drive (FL-758), Stay Straight on Higel Ave, Take first right onto Ocean Blvd, Turns into Beach Rd, and We are on the Right. From South: Take I-75 North to exit 205 (Clark Road), Turn left on Clark Road/FL-72, Keep right at the fork to stay on FL-72, Turn Right onto FL-758 (Midnight Pass), Stay Straight to go on Beach Road, we are on the Left.

Things to know

Cancellation policy

Property rules

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

Safety & security

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