House - Rating 4.9 (33)

Ocean Overlook


Bedroom 8 bedrooms
Bathroom 8 baths
Half Bathroom 2 half baths
Guests 18 guests
Pets Allowed Pets Allowed

  • Address: 316 Beach Rd
  • Location: Siesta Key
  • Type: House
  • View: Ocean View

Location Location

Description Description
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.

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This property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, 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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Swipe Swipe for Availability

Bedding Bedding
Bedroom 1
1 King

Attached Bathroom

Bedroom 2
1 King

Attached Bathroom

Bedroom 3
1 King

Attached Bathroom

Bedroom 4
1 Queen

Attached Bathroom

Bedroom 5
1 Twin over Full Bunk Bed

Attached Bathroom

Bedroom 6
1 King

Attached Bathroom

Bedroom 7
1 King

Attached Bathroom

Bedroom 8
1 King

Attached Bathroom


Amenities 74 Amenities
  • Gas Grill
  • Grill
  • Gulf of Mexico Views
  • Heated Pool (seasonally)
  • No Smoking
  • Security Camera
  • Streaming Service
  • Walking Distance to Siesta Key Village
  • Washer and Dryer
  • Water Views
  • Water/Ice Dispenser on Fridge
  • Waterfront
Essentials
  • Air Conditioning
  • Beach Chairs Provided
  • Beach Towels Included
  • Bed Linens
  • Dryer
  • Hair Dryer
  • Heating
  • Hot Water
  • Iron and Ironing Board
  • Long Term Stays Allowed
  • Private Entrance
  • Towels
  • Washer
Exterior
  • Balcony with Beach View
  • BBQ Grill
  • Hot Tub
  • Hot Tub or Spa
  • Outdoor Dining Area
  • Outdoor Seating
  • Outdoor Shower
  • Pool
  • Private Pool
  • Spa
  • Sun Loungers
Fun and Entertainment
  • Foosball
  • Smart TV
  • Video Game Console
Highlight
  • Virtual Tour
Home Safety
  • Carbon Monoxide Detector
  • Fire Extinguisher
  • Keyless Lock
  • Smoke Detector
Interior
  • Clothes Hangers
  • Desk
  • Elevator
  • Full Kitchen
  • Wet Bar
Kitchen
  • Baking Sheet
  • BBQ Utensils
  • Blender
  • Coffee Maker
  • Dining table
  • Dishes and Utensils
  • Dishwasher
  • Hot Water Kettle
  • Ice Maker
  • Kitchen Island
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Wine Glasses
Location
  • 2-minute walk to the beach
  • Across the Street from the Beach
  • Beach Front
  • Beach View
  • Beach Views
  • Ocean View
  • Residential Street
  • Water View
Parking
  • Five (5) Parking Spaces

Reviews Rating 4.9 (33) Reviews
Rating 4
The pictures were exactly as described. I loved how spacious the house was for our 15 guests, everyone had their own bedroom and bathroom for privacy. We loved the top desk on the 4th floor, enjoy coffee in morning, able to see the ocean and relaxing at night with a glass of wine. We loved the main Block of shopping and restaurants were a 5-10 minute walk around the corner. The beach access was 2 houses down, easy walk with a wagon, beach chairs and cooler. The recommendations I
Would suggest is giving guests more supplies such as Toilet paper, paper towel, dish soap, coffee filters and pods. More bathroom towels and washcloths, shampoo, conditioner and body wash and provide basic spices, salt and pepper and hot pads for hot dishes out of the oven in addition for more pots and pans and cooking utensils. I would recommend a beach umbrella to take to the beach for individuals who love the beach but can’t be in the sun all day. Overall happy with our vacation.
Jennifer - Posted: 11/6/2025
Hi, Jennifer, thank you for staying with us at Ocean Overlook. We’re so glad the home was exactly as pictured and spacious enough for your group of fifteen, with plenty of privacy for everyone. The fourth floor deck is such a special spot for morning coffee and evening wine, and the easy walk to the beach, shops, and restaurants makes this location hard to beat. We appreciate your thoughtful suggestions, we start guests out with a starter pack, and after that they provide for themselves. Feedback like this helps us improve the guest experience and we’ll be reviewing these recommendations with our team. We’re happy to hear you still enjoyed your vacation and hope to welcome you back with Siesta Key Luxury Rental Properties!!
Prime Vacations staff
Rating 5
The rental was absolutely perfect—clean, comfortable, and with stunning views overlooking Siesta Key Beach. Just a two-minute walk to the village and all the great eateries, it couldn’t be more convenient. The owners were incredibly responsive and kind, making the entire stay seamless. Highly recommended for a relaxing beach getaway
Jayan - Posted: 10/26/2025
Hi, Jayan, we’re thrilled to hear you had such a perfect stay at Ocean Overlook! The views, the easy walk to Siesta Village, and that laid back beach vibe really make it special. Thank you for the kind words about our responsive team. All of us at Siesta Key Luxury Rental Properties hope to welcome you back for another relaxing getaway soon!!
Prime Vacations staff
Rating 5
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 - Posted: 9/22/2025
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!!
Prime Vacations staff
Rating 5
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 - Posted: 8/19/2025
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!
Prime Vacations staff
Rating 5
James - Posted: 8/15/2025
Rating 5
Great Family Beach Property
Tremendous property!! Beautiful views of the Gulf. Easily walkable to the beach. Large, spacious house. Great for big families!!!
Justin - Posted: 6/26/2025
Rating 5
Beautiful home and location
The home was in great shape with a beautiful pool and view. The rooms and beds were all very nice and the porcess from start to finish was easy
Bryan - Posted: 5/27/2025
Thank you so much for sharing your experience!! We hope to see you again in the future!
Prime Vacations staff
Rating 5
There was plenty of space, close to the beach. Pool was great and heated. Highly recommend.
Crispin - Posted: 4/25/2025
Thank you for the positive review! We're thrilled to hear that you enjoyed your stay and found the amenities, such as the spacious accommodations and the heated pool, to be excellent. Your recommendation is greatly appreciated, and we look forward to welcoming you back in the future.
Prime Vacations staff
Rating 5
Great place. We did a work retreat and it met all of our needs. Plenty of space to cook. View of the ocean is great. I would recommend! We slept 9 people comfortably.
Zach - Posted: 2/8/2025
Thank you for your kind review. We're delighted to hear that the property was able to accommodate your work retreat and meet your needs. The ocean view is indeed a lovely feature, and we're glad you and your group were able to sleep comfortably. We appreciate your recommendation and look forward to hosting you again in the future.
Prime Vacations staff
Rating 5
Patrick G. - Posted: 2/7/2025
Rating 5
Lovely Rental
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 - Posted: 8/27/2024
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!
Prime Vacations staff
Rating 5
Is a amazing house, in the most beautiful beach
Elizabeth - Posted: 6/2/2024
Thank you for your lovely review, Elizabeth! We're so happy you loved the house and its location on the beautiful beach. It was a pleasure having you, and we can't wait to welcome you back for more fun and relaxation! 😊
Prime Vacations staff
Rating 5
This is a great beach home very so to the beautiful beach of Siesta Key. Restaurants & bars are so close within walking distance. We enjoyed our stay. This house is very nice.
Reyanne - Posted: 5/13/2024
Thank you for your positive feedback, Reyanne! We're delighted you enjoyed the convenience of nearby restaurants and bars during your stay. We strive to maintain a welcoming environment and are pleased you found the house to your liking. We hope to host you again soon!
Prime Vacations staff
Rating 5
Walkable to Siesta Key village and the beach! What more can you ask for a location. Also has one of the best family and group friendly pools I’ve stayed at! Would go again just for the pool.
Matt - Posted: 9/18/2023
Thank you for allowing us to host you, Matt. We are glad you enjoyed your stay and hope to welcome you back soon!
Prime Vacations staff
Rating 5
Perfect for friends and family
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. - Posted: 7/15/2023
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!
Prime Vacations staff
Rating 5
absolutely wonderful accommodations
Carlos Fausto - Posted: 7/8/2023
Thank you for allowing us to host you, Carlos. We are glad you enjoyed your stay and hope to welcome you back again soon!
Prime Vacations staff
Rating 5
Perfect place, would definitely rent again!
Renee - Posted: 5/14/2023
Thank you for allowing us to host you, Renee. We are glad you enjoyed your stay and hope to welcome you back again soon!
Prime Vacations staff
Rating 5
We absolutely loved the home! It was perfect for multiple families - enough bedrooms, bathrooms, and communal space for everyone. One thing to watch with small kids is the stairs - there are many and they're hard (tile) with sharp edges (a fall would be rough!). Luckily the kids were huge fans of the elevator. The pool & hot tub area was well designed and so much fun - we ended up here every afternoon. The only downsides was with how bare the supplies were. Not even oil or salt & pepper were provided, and only one tiny bottle of dish soap. For the pricepoint it was a bit disappointing.
Stephanie - Posted: 1/29/2023
Stephanie, thank you for taking the time to share your experience with us. We are thrilled to hear you and your family were comfortable and enjoyed your stay. We also appreciate your feedback and will be sure to pass everything on to our team and owners. We hope to host you again sometime in the future!
Prime Vacations staff
Rating 5
Better than the photos! This place was perfect and we’ll be back again. Thank you!
April - Posted: 12/11/2022
April, we are thrilled to hear you enjoyed your stay. You were wonderful guests, and we can't wait to host you again!
Prime Vacations staff
Rating 5
Perfect space for 11 adults and 5 children for a week in the sun. Room to celebrate all together as well as have quiet time in smaller groups. Everyone really enjoyed the heated pool with the outdoor TV to keep the sports fans among us up to date. Wouldn’t change a thing and cannot wait to return.
Mary - Posted: 11/27/2022
Mary, we are glad you and your family enjoyed the home, heated pool, and outdoor TV. You were wonderful guests, and we can't wait to host you all again sometime soon!
Prime Vacations staff
Rating 5
Beautiful Stay
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. - Posted: 11/15/2022
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!
Prime Vacations staff
Rating 5
bday getaway with friends
This property was exactly as advertised! Everything was clean and worked well. Excellent location as well.
Walt B. - Posted: 10/26/2022
Walt, thank you for taking the time to share your experience with us. We are happy to hear you enjoyed your stay, and we hope to host you again soon!
Prime Vacations staff
Rating 5
The house was great. Everyone in my party loved it. It was just like the pics, and we appreciate the prompt response when we had questions. I plan on definitely coming back with my extended family or with a group of couples.
Lisa - Posted: 8/7/2022
Thank you for allowing us to host you, Lisa! We are happy to hear that you enjoyed the home. We look forward to welcoming you back again soon!
Prime Vacations staff
Rating 5
Beautiful house close to the beach, we will definitely be returning
Christopher - Posted: 3/6/2022
Rating 5
This property was perfect for our winter vacation with our family! We had four generations so the elevator came in really handy for the 1 year old all the way up to the 98 year old. We loved the pool, the proximity to the beach and to the village, and there were plenty of bedrooms and bathrooms, with enough space for all 15 of us.
Mike - Posted: 3/1/2022
Rating 5
Perfectly big and beautiful
The home was lovely.
Jhana P. - Posted: 2/27/2022
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
Prime Vacations staff
Rating 5
Wonderful Property
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. - Posted: 1/6/2022
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!
Prime Vacations staff
Rating 5
Great place, right on the beach, short walk to town, all the amenities.
Timothy - Posted: 12/14/2021
Dear Timothy,

Thanks so much for reviewing your recent stay with us! We are so glad to hear you had such a wonderful time at our 'Ocean Overlook' property! We are also happy to hear that this home's unbeatable location made for easy access to both the beach as well as Siesta Key Village. We hope that you come back to visit us again soon, you are welcome anytime!

Sincerely,
Siesta Key Luxury Rental Properties
Prime Vacations staff
Rating 5
Great location, beautiful place
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. - Posted: 11/5/2021
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
Prime Vacations staff
Rating 5
This was truly the best rental we have ever had. Adam was so responsive and truly made our vacation. The house was in perfect condition and had everything we needed for the entire week. The pool was perfect and the house is so spacious. You cannot beat the view! You won’t want to leave the house!! Don’t think twice when booking!
Trish - Posted: 10/26/2021
Dear Trish,

Thank you for reviewing your recent stay with us! We are so glad that you had a wonderful stay at one of our newest properties, 'Ocean Overlook.' The location of and view from this home truly cannot be beat! The pool is also a very fun spot with both sun and shade and a private hot tub, so we are thrilled that your group enjoyed both the interior and exterior spaces of this home! It was our pleasure to host you and hope you'll return to stay with us again very soon!

Sincerely,
Siesta Key Luxury Rental Properties
Prime Vacations staff
Rating 5
This house does not disappoint. Great living space. Great views and the perfect location. Worth every penny.
The Duval’s
Brian - Posted: 10/12/2021
Dear Brian,

Thank you for reviewing your recent stay with us at one of our newest properties, 'Ocean Overlook.' We are thrilled that this home exceeded your expectations and that a relaxing and fun vacation was had by all! We hope to see you back in Siesta Key again very soon!

Kind regards,
Siesta Key Luxury Rental Properties
Prime Vacations staff
Rating 5
Excellent host and the place was beautiful.
Karsten - Posted: 9/28/2021
Dear Karsten,

Thank you for reviewing your stay with us on beautiful Siesta Key! We are so glad you enjoyed one of our newest properties 'Ocean Overlook'! It was our pleasure to host you and your group, please come back and see us again soon!

Kind regards,
Siesta Key Luxury Rental Properties
Prime Vacations staff
Rating 5
This house is stunning and the location could not be beat. Short walk to the beach and Siesta Key Village. We also enjoyed the pool and hot tub on the couple rainy days we had. All the bedrooms and bathrooms were very well appointed. A great time was had by all! Thank you Adam for sharing your home with us.
Susan - Posted: 9/18/2021
Susan,

Thank you so much for reviewing your recent stay with us at one of our newest properties, 'Ocean Overlook!' We are thrilled that you enjoyed this home's location, amenities and spacious layout. Thank you for choosing to rent with us, it was our absolute pleasure to host you and your group! Come back and see us again soon, you're welcome anytime!

Kind regards,
Siesta Key Luxury Rental Properties
Prime Vacations staff
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