Siesta Key, FL
Ocean Overlook
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) | Availability | Min Stay (nights) |
|---|---|---|---|
| Apr 4, 2026 | $2,796.45 | Not Available | 2 |
| Apr 5, 2026 | $2,337.07 | Not Available | 2 |
| Apr 6, 2026 | $2,641.95 | Not Available | 2 |
| Apr 7, 2026 | $2,852.07 | Not Available | 2 |
| Apr 8, 2026 | $2,796.45 | Not Available | 2 |
| Apr 9, 2026 | $2,456.55 | Not Available | 2 |
| Apr 10, 2026 | $3,961.38 | Not Available | 2 |
| Apr 11, 2026 | $2,291.75 | Not Available | 2 |
| Apr 12, 2026 | $1,291.62 | Not Available | 2 |
| Apr 13, 2026 | $1,200.98 | Not Available | 2 |
| Apr 14, 2026 | $1,173.17 | Not Available | 2 |
| Apr 15, 2026 | $1,263.81 | Not Available | 2 |
| Apr 16, 2026 | $1,459.51 | Not Available | 2 |
| Apr 17, 2026 | $2,901.51 | Not Available | 3 |
| Apr 18, 2026 | $2,842.80 | Available | 3 |
| Apr 19, 2026 | $1,726.28 | Available | 3 |
| Apr 20, 2026 | $2,195.96 | Available | 3 |
| Apr 21, 2026 | $2,179.48 | Available | 3 |
| Apr 22, 2026 | $2,864.43 | Not Available | 3 |
| Apr 23, 2026 | $2,989.06 | Not Available | 3 |
| Apr 24, 2026 | $2,866.49 | Not Available | 3 |
| Apr 25, 2026 | $2,600.75 | Not Available | 3 |
| Apr 26, 2026 | $1,811.77 | Available | 3 |
| Apr 27, 2026 | $1,646.97 | Available | 3 |
| Apr 28, 2026 | $1,587.23 | Available | 3 |
| Apr 29, 2026 | $1,633.58 | Available | 3 |
| Apr 30, 2026 | $1,768.51 | Available | 3 |
| May 1, 2026 | $1,919.92 | Not Available | 3 |
| May 2, 2026 | $1,925.07 | Not Available | 3 |
| May 3, 2026 | $1,735.55 | Not Available | 4 |
| May 4, 2026 | $1,344.15 | Not Available | 3 |
| May 5, 2026 | $1,317.37 | Not Available | 3 |
| May 6, 2026 | $1,400.80 | Not Available | 3 |
| May 7, 2026 | $1,592.38 | Not Available | 4 |
| May 8, 2026 | $1,980.69 | Not Available | 4 |
| May 9, 2026 | $1,972.45 | Not Available | 4 |
| May 10, 2026 | $2,091.93 | Available | 4 |
| May 11, 2026 | $1,316.34 | Available | 3 |
| May 12, 2026 | $1,316.34 | Available | 3 |
| May 13, 2026 | $1,369.90 | Available | 3 |
| May 14, 2026 | $1,499.68 | Available | 4 |
| May 15, 2026 | $1,614.01 | Not Available | 4 |
| May 16, 2026 | $1,628.43 | Not Available | 4 |
| May 17, 2026 | $1,279.26 | Not Available | 4 |
| May 18, 2026 | $1,179.35 | Not Available | 3 |
| May 19, 2026 | $1,153.60 | Available | 3 |
| May 20, 2026 | $1,204.07 | Available | 3 |
| May 21, 2026 | $2,796.45 | Available | 4 |
| May 22, 2026 | $3,421.66 | Available | 4 |
| May 23, 2026 | $3,416.51 | Available | 4 |
| May 24, 2026 | $3,413.42 | Available | 4 |
| May 25, 2026 | $1,423.46 | Not Available | 3 |
| May 26, 2026 | $1,430.67 | Not Available | 3 |
| May 27, 2026 | $1,188.62 | Not Available | 3 |
| May 28, 2026 | $1,298.83 | Not Available | 4 |
| May 29, 2026 | $1,389.47 | Not Available | 4 |
| May 30, 2026 | $1,421.40 | Not Available | 4 |
| May 31, 2026 | $1,284.41 | Not Available | 4 |
| Jun 1, 2026 | $1,749.97 | Not Available | 3 |
| Jun 2, 2026 | $2,486.42 | Available | 3 |
| Jun 3, 2026 | $2,486.42 | Available | 3 |
| Jun 4, 2026 | $2,486.42 | Available | 4 |
| Jun 5, 2026 | $2,486.42 | Available | 4 |
| Jun 6, 2026 | $3,420.63 | Not Available | 7 |
| Jun 7, 2026 | $1,933.31 | Not Available | 7 |
| Jun 8, 2026 | $1,783.96 | Not Available | 7 |
| Jun 9, 2026 | $1,742.76 | Not Available | 7 |
| Jun 10, 2026 | $1,816.92 | Not Available | 7 |
| Jun 11, 2026 | $1,994.08 | Not Available | 7 |
| Jun 12, 2026 | $2,148.58 | Not Available | 7 |
| Jun 13, 2026 | $2,504.96 | Not Available | 7 |
| Jun 14, 2026 | $2,255.70 | Not Available | 7 |
| Jun 15, 2026 | $2,079.57 | Not Available | 7 |
| Jun 16, 2026 | $2,125.92 | Not Available | 7 |
| Jun 17, 2026 | $2,131.07 | Not Available | 7 |
| Jun 18, 2026 | $2,344.28 | Not Available | 7 |
| Jun 19, 2026 | $2,544.10 | Not Available | 7 |
| Jun 20, 2026 | $2,460.67 | Not Available | 7 |
| Jun 21, 2026 | $2,223.77 | Not Available | 7 |
| Jun 22, 2026 | $2,050.73 | Not Available | 7 |
| Jun 23, 2026 | $2,078.54 | Not Available | 7 |
| Jun 24, 2026 | $2,091.93 | Not Available | 7 |
| Jun 25, 2026 | $2,297.93 | Not Available | 7 |
| Jun 26, 2026 | $2,510.11 | Not Available | 7 |
| Jun 27, 2026 | $2,279.39 | Available | 7 |
| Jun 28, 2026 | $2,149.61 | Available | 7 |
| Jun 29, 2026 | $1,943.61 | Available | 7 |
| Jun 30, 2026 | $1,897.26 | Available | 7 |
| Jul 1, 2026 | $1,666.54 | Available | 7 |
| Jul 2, 2026 | $2,984.94 | Available | 7 |
| Jul 3, 2026 | $2,984.94 | Available | 7 |
Where you'll sleep
Amenities
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.
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
Refundable Bookings
Cancellation deadlines:
- For stays under 15 nights, you may cancel or reschedule up to 14 days before check-in for a full refund. For stays 15 nights or longer, the cancellation window is 60 days.
- For some homes, a 30-day deadline applies — this will be clearly shown before you book.
- Cancellations must be submitted before 4 PM EST on the deadline day to qualify.
Fair-Refund Policy
If you cancel after the deadline:
- Prime Vacations - Siesta Key will relist your dates and automatically refund you for any nights that rebook.
- The refund per night will be the lower of the original price or the rebooking rate. Nights that do not rebook are non-refundable.
Half-Now, Half-Later Bookings
- The first half of your payment is non-refundable.
- The second half may be refunded according to the standard cancellation policy above.
Non-Refundable Bookings
If you selected a Non-Refundable rate at checkout, the booking cannot be changed or canceled, and no refund will be issued.
Date Changes & Rebooking
Once a stay is canceled, you can't rebook the same dates yourself. If you need help choosing new dates, our Concierge team is happy to assist.
Transfers to Another Guest
You may transfer your booking to someone else at no charge. Just contact the Concierge with the new guest's name and email. The new guest must accept the transfer for it to take effect.
Policy Match Guarantee
If a better price is available for the same property on Airbnb or the owner's site, contact the Concierge — Prime Vacations - Siesta Key will match it.
By completing your booking, you acknowledge and agree to Prime Vacations - Siesta Key's cancellation policy.