Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook
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.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Siesta Key
Located on the beach, this holiday home is in Siesta Key Village, a neighbourhood in Siesta Key. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Travelling with kids? Consider Mote Marine Laboratory & Aquarium, or check out an event or a game at Ed Smith Stadium. Looking to get your feet wet? Jet skiing, kayaking and parasailing adventures can be found near the property.
Siesta Key Beach Playground - 20 min walk - 1.7 km
St. Boniface Episcopal Church Labyrinth - 2 min drive - 2.0 km
Crescent Beach - 7 min drive - 5.5 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 34 min drive
Restaurants
Siesta Beach Pavilion - 15 min walk
Siesta Key Snack Bar - 15 min walk
Circle K - 9 min walk
Gilligan's Island Bar & Grill - 4 min walk
Sun Garden Cafe - 8 min walk
Frequently asked questions
Does Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook?
As of 19 May, 2026, prices found for a 1-night stay for 2 adults at Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook on 25 Aug, 2026 start from S$1,884, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook?
On-site parking is available at the property.
What time is check-in at Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook?
Check-in begins at 4:00 PM.
What time is check-out at Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook?
Checkout is at 10:00 AM.
Where is Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook located?
Nestled on the beach, this Siesta Key Village holiday home is within 1 mi (2 km) of Siesta Key Farmers Market and Siesta Key Beach. Irma Beach and Siesta Key Beach Playground are also within 2 miles (3 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
House was great — perfect location walkable to town and beach. Nice pool and outdoor area, plenty of room and lots of space for big groups.
Doug M.
Stayed 3 nights in Feb 2026
Response from VrboOwner on 3 Mar, 2026
We’re so glad you enjoyed your stay at Ocean Overlook, Doug! The walkable location to town and the beach really does make it easy to settle into island time. It’s great to hear the pool and outdoor space worked so well for your group there’s nothing better than having room to gather and room to spread out. All of us at Siesta Key Luxury Rental Properties would love to host you again for another elevated coastal getaway
Beautiful home! Amazing location! Super quick to answer our questions and respond to any concerns.
Laura M.
Stayed 3 nights in Jan 2026
Response from VrboOwner on 4 Feb, 2026
Thank you for the kind words, Laura! We’re so happy you loved the Ocean Overlook home and the location. It was a pleasure hosting you, and we’re glad our team could be there whenever you needed us. We’d love to welcome you back to Siesta Key Luxury Rental Properties for another laid-back luxury escape.
Host was very welcoming. Just had to send a text asking for the entrance code. Other than that, they were very responsive. House was ready for us!
Jen P.
Stayed 4 nights in Jan 2026
Response from VrboOwner on 28 Jan, 2026
Thank you for choosing us for your recent stay!
Every review and every star you give us makes a huge difference to our success.
We hope to host you again in the future!
The property was exactly as advertised, and communication with the host was always efficient and timely. The space was very accommodating for our large family, and the location couldn’t have been more perfect. We didn’t want for anything during our stay—it had everything we needed. Highly recommend! As we will be planning a future stay.
Robyn
Stayed 2 nights in Sep 2025
Response from VrboOwner on 26 Sept, 2025
Thank you for the glowing review, Robyn! We’re so glad the home was a perfect fit for your family and that you had everything you needed for a comfortable stay. Happy to hear communication was smooth, too. We’d love to welcome you back for another getaway with Siesta Key Luxury Rental Properties!!
Four floors, great vistas and a fantastic pool.Not to mention, all that you need to take out to the beach is is there for you, with plenty of towels, chairs and a pull cart to get to the beach(which all looked brand new).Everything was very high end in and around the whole house.Everywhere to eat and drink were all walkable.
William M.
Stayed 5 nights in Aug 2025
Response from VrboOwner on 22 Aug, 2025
Thank you so much for your wonderful review of our property, William! We are thrilled to hear that you enjoyed your stay and found the amenities, views, and location of our home to be exceptional. We are grateful for your kind words and review. It was our pleasure to provide you with a comfortable and enjoyable experience, and we look forward to welcoming you back in the future!
Had a group of friends stay together and it was perfect. 1 min walk from the beach, gorgeous views from the balcony and everything we could have hoped for from a comfort standpoint.
Genesis K.
Stayed 1 night in Nov 2022
Response from VrboOwner on 17 Nov, 2022
Thank you for allowing us to host you, Genesis. We are glad you and your friends enjoyed the home and the balcony views. You were all wonderful guests, and we hope to host you again soon!
We had a terrific vacation.the location is ideal and the space is plentiful. All technology was functioning and easy to use. Beach is close and only a short walk as is restaurants and shops.
This home could easily house 2 families with 2-3 kids each.
Art M.
Stayed 6 nights in Aug 2024
Response from VrboOwner on 17 Sept, 2024
Thank you for your fantastic review! We’re delighted to hear that you had a terrific vacation and found the location ideal with plenty of space. It’s great to know that the technology was easy to use and that the proximity to the beach, restaurants, and shops added to your convenience. We’re glad the home met your needs and could comfortably accommodate multiple families. We look forward to welcoming you back for another great stay!
The TV in the pool did not worked and de AC in the 4th floor was so slow. the rest, perfect and amazing views.
silvia r.
Stayed 2 nights in Aug 2023
Response from VrboOwner on 18 Oct, 2023
Thank you for taking the time to share your experience, Silvia. We are glad you enjoyed the home and convenient location. We appreciate your feedback about the AC and TV and are glad to report that these are back in working order. You were terrific guests, and we hope to welcome you back soon!
Great location to walk to beach and village. Really nice pool set up, beautiful bedrooms and living spaces. Just a couple of negatives but overall we loved this property. Andrew (property manager) kept in touch and was very responsive. We did ask if we could keep our luggage there after 10 am checkout but owners weren’t open to that.
Lori M.
Stayed 5 nights in Oct 2021
Response from VrboOwner on 8 Nov, 2021
Dear Lori,
Thank you for reviewing your recent stay at our 'Ocean Overlook' property! We are so glad that you found this home to be beautifully appointed and it a premier location, close to both the beach and Siesta Key Village. We are also thrilled to hear that Andrew and our property management team were responsive to any questions you had during your stay.
As we explained to you, we had another guest checking into the home that same day at 4pm. With this being a large, 8-bedroom home and over 5,000 sq. feet we could not allow you and your belongings to stay on the property after the communicated check-out time (10am) which was available to you at the time of booking, in our pre-arrival emails as well as our departure emails. We did however, offer to transport your luggage to our office located in Siesta Key Village for safe keeping until you were ready to depart from the island. We hope that you understand this reasonable explanation as to why we could not accommodate any late check-out.
Sincerely,
Siesta Key Luxury Rental Properties
The house was very comfortable- nothing too fancy but very clean and perfect for our multi family vacation. The pool was fantastic- plenty of space in the sun and the shade. The location was great- 5 to 10 minute walk into town. Tons of restaurants and shops. Things seem to close down around 10pm and the streets are pretty quiet after that. The house is located right on the street so we were a little worried about traffic noise at night but it was very quiet. Every bedroom having its own bathroom was so nice. There are 2 washing machines and 2 dryers which came in very handy. The beach access is super close but the walk from the beach access point to the beach is very long. 2 beach wagons are provided but they don’t work very well because the sand isn’t compacted. The extra refrigerator on the ground level was very nice. We had a great vacation!
Angie S.
Stayed 5 nights in Jul 2023
Response from VrboOwner on 5 Oct, 2023
Thank you for taking the time to share your wonderful experience with us, Angie. We are glad you enjoyed your stay and hope to welcome you back soon!
Our family had a wonderful time. The house is beautiful with a great view of the water. Very spacious. Plenty of bathrooms. But we would have appreciated if the bathrooms had handicapped accessibility features like handle bars. The elevator was great; but it broke 3 times. Thankfully, nobody got stuck in the elevator and the maintenance guy came very quickly each time. He was very pleasant and professional. We also would have appreciated potholders and additional hand towels in the kitchen. Since we had a baby with us, we were very particular about clean floors. We couldn’t find a mop to clean. We ended up buying a swiffer and left it there. Lastly, we loved the pool; but didn’t enjoy it very much because there were tons of mosquitoes. We bought some citronella; but not enough to drive away the mosquitoes. (The mosquitoes might have come from the swimming pool next door which was green and cloudy). All in all, we enjoyed our stay. It was so nice to be in one house where we gathered together when we wanted to, but kept our private spaces when we wanted some quiet time. Thank you for sharing your home with us.
Maria Arlen D.
Stayed 7 nights in Aug 2025
Response from VrboOwner on 22 Aug, 2025
Thank you for your detailed review of your stay at our property, Maria. We appreciate the constructive feedback and are glad to hear that your family had an overall enjoyable experience. Please accept our apologies for the issues with the mosquitoes, with us living on an island in Florida, it is something we deal with during the hot summers throughout Florida. Your comments are valuable, and we are grateful for the opportunity to learn and enhance the property for our guests. We hope you will consider staying with us again in the future!
Jhana,
Thanks for the 5-star review, we're so glad you had an enjoyable stay with us! Please come back and see us again soon!
Sincerely,
Siesta Key Luxury Rental Properties
The entire property was amazing! From the 8 ensuites, the 2 living areas, the chefs kitchen, the beautiful pool and spa area, and the view of the ocean from the top balcony. This rental is everything you would need for a family reunion.
Christina F.
Stayed 3 nights in Jan 2022
Response from VrboOwner on 9 Feb, 2023
Christina, thank you for taking the time to share your experience with us. We are thrilled to hear you enjoyed the home, living area, kitchen, pool, and spa. We hope to host you again sometime in the future!
We are an owner operated rental company on Siesta Key. We manage a 58+ unit resort and single family homes. All of our properties are within walking distance to the beach and the village. We have a high focus on customer service and our primary focus is ensuring our guests have a spectacular stay with us in paradise.
Why they chose this property
All of the shops, dining, entertainment is at your fingertips when you stay with us here. You are also close to a number of beach access points. Walking distance to everything, and the property itself is amazing and it offers numerous amenities that you’ll love!
What makes this property unique
Location. Location. Location. The ease of use is incredible. Walk Everywhere and Enjoy paradise with ease. You’ll love everything about this amazing rental property!
Languages:
English
Premier Host
They consistently provide great experiences for their guests