Ocean Overlook

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  • Sleeps: 18
  • Bedrooms: 8
  • Full Bathrooms: 8
  • Half Bathrooms: 2
  • Pets: 2

Description

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.

Room Details

Room Beds
Elevator
Wet Bar
Game Room
Outdoor Patio
Dining Room
Living Room
Bedroom 1
  • King
Bedroom 8
  • King
Bedroom 7
  • King
Bedroom 6
  • King
Bedroom 5
  • Full over Full Bunk Bed
Bedroom 4
  • Queen
Bedroom 3
  • King
Bedroom 2
  • King

Amenities

Fun and Entertainment
• Foosball
• Game Room
• Games
• Smart TV
• TV
• Video Game Console
Essentials
• Air Conditioning
• Beach Chairs Provided
• Beach Towels Included
• Bed Linens
• Clothes Hangers
• Dryer
• Free WiFi
• Hair Dryer
• Heating
• Hospital Close By
• Hot Water
• Iron and Ironing Board
• Long Term Stays Allowed
• Pets Allowed
• Private Entrance
• Shampoo
• Towels
• Washer
• Wifi
Kitchen
• Baking Sheet
• BBQ Utensils
• Blender
• Coffee Maker
• Dining Table
• Dishes and Utensils
• Dishwasher
• Hot Water Kettle
• Ice Maker
• Keurig Coffee Maker
• Kitchen Island
• Microwave
• Oven
• Pots and Pans
• Refrigerator
• Stove
• Toaster
• Wine Fridge
• Wine Glasses
Location
• 2-minute walk to the beach
• Across the Street from the Beach
• Beach Front
• Beach View
• Near Ocean
• Ocean View
• Residential Street
• Siesta Key
• Walking Distance to Siesta Key Village
• Water Front
• Water View
Exterior
• Backyard
• Balcony
• Balcony with Beach View
• BBQ Area
• Covered Deck
• Fenced Yard
• Gas BBQ Grill
• Heated Pool
• Hot Tub or Spa
• Outdoor Dining Area
• Outdoor Seating
• Outdoor Shower
• Outdoor TV
• Private Pool
• Sun Loungers
Parking
• Five (5) Parking Spaces
Home Safety
• Carbon Monoxide Detector
• Contactless Check-In
• Fire Extinguisher
• Keyless Lock
• Outdoor Lighting
• Security Camera Present
• Smoke Detector
Interior
• Ceiling Fans
• Clothing Storage
• Desk
• Elevator
• Full Kitchen
• Living Room
• Second Fridge
• Wet Bar
Things To Do
• Bird Watching Nearby
• Boating Nearby
• Fishing Nearby
• Golf Nearby
• Health Beauty Spa Nearby
• Jet Skiing Nearby
• Kayaking Nearby
• Laundromat Close By
• Marina Nearby
• Museums
• Parasailing Nearby
• Sailing Nearby
• Shopping Nearby
• Swimming Nearby
• Water Sports Nearby
• Wildlife Viewing Nearby

Rates

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Availability

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Reviews

Title Guest Rating Staff Comments Date
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 5 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 02/26/2026
Great communication. Melissa 5 Thank you for the kind words, Melissa! We’re so glad you enjoyed your stay at Ocean Overlook and felt well taken care of throughout. Clear, thoughtful communication is part of the experience for us. We’d love to host you again for another effortless Siesta Key escape! 02/08/2026
Beautiful home! Amazing location! Super quick to answer our questions and respond to any concerns. Laura 5 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. 02/01/2026
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 5 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! 01/27/2026
The property was beautiful with stunning views of the Gulf and easy access to pristine beaches. There was plenty of room for our group and everyone really enjoyed our time there. The property was easily walkable and made for a great experience. Jonathan 5 Hi, Jonathan, thank you for the wonderful review! We’re so happy you enjoyed your stay at Siesta Key Luxury Rental Properties at Ocean Overlook. Those Gulf views, easy beach access, and walkable location really do make this home something special. We’re thrilled the space was a great fit for your group and that everyone had such a memorable experience. Thank you for choosing Siesta Key Luxury Rental Properties, and we’d love to welcome you back for another luxury Siesta Key escape in the future!! 01/19/2026
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 4 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!! 11/06/2025
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 5 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!! 10/26/2025
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 5 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!! 09/22/2025
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 5 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! 08/19/2025
James 5 08/16/2025
Tremendous property!! Beautiful views of the Gulf. Easily walkable to the beach. Large, spacious house. Great for big families!!! Justin 5 06/27/2025
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 5 Thank you so much for sharing your experience!! We hope to see you again in the future! 05/27/2025
There was plenty of space, close to the beach. Pool was great and heated. Highly recommend. Crispin 5 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. 04/25/2025
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 5 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. 02/08/2025
Patrick G. 5 02/08/2025
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 5 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! 08/27/2024
Is a amazing house, in the most beautiful beach Elizabeth 5 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! 😊 06/02/2024
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 5 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! 05/13/2024
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 5 Thank you for allowing us to host you, Matt. We are glad you enjoyed your stay and hope to welcome you back soon! 09/18/2023
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. 5 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! 07/15/2023
absolutely wonderful accommodations Carlos Fausto 5 Thank you for allowing us to host you, Carlos. We are glad you enjoyed your stay and hope to welcome you back again soon! 07/08/2023
Perfect place, would definitely rent again! Renee 5 Thank you for allowing us to host you, Renee. We are glad you enjoyed your stay and hope to welcome you back again soon! 05/14/2023
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 5 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! 01/29/2023
Better than the photos! This place was perfect and we’ll be back again. Thank you! April 5 April, we are thrilled to hear you enjoyed your stay. You were wonderful guests, and we can't wait to host you again! 12/11/2022
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 5 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! 11/27/2022
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. 5 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! 11/15/2022
This property was exactly as advertised! Everything was clean and worked well. Excellent location as well. Walt B. 5 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! 10/26/2022
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 5 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! 08/07/2022
Beautiful house close to the beach, we will definitely be returning Christopher 5 03/06/2022
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 5 03/01/2022
The home was lovely. Jhana P. 5 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 02/27/2022
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. 5 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! 01/06/2022
Great place, right on the beach, short walk to town, all the amenities. Timothy 5 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
12/14/2021
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. 5 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 11/05/2021
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 5 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
10/26/2021
This house does not disappoint. Great living space. Great views and the perfect location. Worth every penny.
The Duval’s
Brian 5 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
10/12/2021
Excellent host and the place was beautiful. Karsten 5 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
09/28/2021
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 5 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
09/18/2021