Siesta Key, FL

Ocean Overlook

8 bedrooms8 beds9 baths18 guestsNew

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!

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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.

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.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 17, 2026$1,766.45Not Available2
Jul 18, 2026$1,561.48Not Available2
Jul 19, 2026$978.50Not Available2
Jul 20, 2026$978.50Not Available2
Jul 21, 2026$978.50Not Available2
Jul 22, 2026$978.50Not Available2
Jul 23, 2026$978.50Not Available2
Jul 24, 2026$1,900.35Not Available2
Jul 25, 2026$1,747.91Not Available2
Jul 26, 2026$1,196.86Not Available2
Jul 27, 2026$1,155.66Not Available2
Jul 28, 2026$1,085.62Not Available2
Jul 29, 2026$1,079.44Not Available2
Jul 30, 2026$1,185.53Not Available2
Jul 31, 2026$1,856.06Not Available3
Aug 1, 2026$1,875.63Not Available3
Aug 2, 2026$1,657.27Not Available3
Aug 3, 2026$1,630.49Not Available3
Aug 4, 2026$1,584.14Not Available3
Aug 5, 2026$1,587.23Not Available3
Aug 6, 2026$1,637.70Not Available3
Aug 7, 2026$1,813.83Not Available3
Aug 8, 2026$1,737.61Not Available3
Aug 9, 2026$1,415.22Not Available3
Aug 10, 2026$1,192.74Available3
Aug 11, 2026$1,192.74Not Available3
Aug 12, 2026$1,240.12Not Available3
Aug 13, 2026$1,292.65Not Available3
Aug 14, 2026$1,538.82Not Available3
Aug 15, 2026$1,446.12Not Available3
Aug 16, 2026$1,397.71Not Available3
Aug 17, 2026$1,117.55Available3
Aug 18, 2026$1,043.39Available3
Aug 19, 2026$1,290.59Available3
Aug 20, 2026$1,347.24Not Available3
Aug 21, 2026$1,453.33Not Available3
Aug 22, 2026$1,481.14Not Available3
Aug 23, 2026$1,383.29Not Available3
Aug 24, 2026$1,502.77Available3
Aug 25, 2026$1,300.89Available3
Aug 26, 2026$1,316.34Available3
Aug 27, 2026$1,457.45Available3
Aug 28, 2026$2,083.69Available3
Aug 29, 2026$2,073.39Available3
Aug 30, 2026$2,002.32Available3
Aug 31, 2026$1,083.56Available3
Sep 1, 2026$1,324.58Available3
Sep 2, 2026$1,326.64Available3
Sep 3, 2026$1,211.28Available3
Sep 4, 2026$1,518.22Not Available3
Sep 5, 2026$1,559.42Not Available3
Sep 6, 2026$1,339Not Available3
Sep 7, 2026$1,226.73Not Available3
Sep 8, 2026$978.50Available2
Sep 9, 2026$978.50Available2
Sep 10, 2026$1,186.56Not Available3
Sep 11, 2026$1,381.23Not Available3
Sep 12, 2026$1,232.91Not Available3
Sep 13, 2026$1,024.85Not Available3
Sep 14, 2026$978.50Not Available3
Sep 15, 2026$978.50Available2
Sep 16, 2026$978.50Available2
Sep 17, 2026$1,124.76Not Available3
Sep 18, 2026$1,275.14Not Available3
Sep 19, 2026$1,416.25Not Available3
Sep 20, 2026$1,171.11Not Available3
Sep 21, 2026$1,070.17Not Available3
Sep 22, 2026$999.10Not Available3
Sep 23, 2026$1,030Not Available3
Sep 24, 2026$1,212.31Not Available3
Sep 25, 2026$1,395.65Not Available3
Sep 26, 2026$1,391.53Not Available3
Sep 27, 2026$1,212.31Available3
Sep 28, 2026$1,036.18Available3
Sep 29, 2026$978.50Available3
Sep 30, 2026$988.80Available3
Oct 1, 2026$1,617.10Available3
Oct 2, 2026$1,703.62Available3
Oct 3, 2026$1,600.62Not Available3
Oct 4, 2026$1,600.62Not Available3
Oct 5, 2026$1,600.62Not Available3
Oct 6, 2026$1,127.85Not Available3
Oct 7, 2026$1,186.56Not Available3
Oct 8, 2026$1,524.40Not Available3
Oct 9, 2026$1,828.25Not Available3
Oct 10, 2026$1,828.25Not Available3
Oct 11, 2026$1,678.90Not Available3
Oct 12, 2026$1,469.81Not Available3
Oct 13, 2026$1,393.59Not Available3
Oct 14, 2026$1,070.17Available3
Oct 15, 2026$1,501.74Not Available3

Amenities

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

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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.

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

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.