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Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook

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A heated pool - Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook (Siesta Key)
Fridge, microwave, oven, stovetop - Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook (Siesta Key)
Dining - Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook (Siesta Key)
Outdoor dining - Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook (Siesta Key)
Smart TV, video games, table football - Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook (Siesta Key)
Sarasota's Ocean Overlook is a dream vacation haven. With eight bedrooms, an amazing backyard featuring a sparkling pool and spa, this home offers ample space for large groups to unwind. Enjoy Gulf views from the balcony or take advantage of outdoor entertainment spaces.

Reviews

9.8 out of 10
Exceptional

Entire home

8 bedrooms9 bathroomsSleeps 18435 sq m

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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!

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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.

Property amenities

Beach

  • On the beach

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 8 bedrooms
  • Bedsheets provided

Bathroom

  • 9 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Games
  • Smart TV
  • Video games

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Lift
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre
  • Near the marina
  • Near the sea
  • On the waterfront

Things to do

  • Arcade/game room
  • Foosball table
  • Heated pool
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Unit size: 4,681 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

32
Ocean Overlook Eight Bedroom House Sleeps 18

About the area

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 Stardust Event Center. Looking to get your feet wet? Jet skiing, kayaking and parasailing adventures can be found near the property. Visit our Siesta Key travel guide
View more Holiday homes in Siesta Key
Map
Siesta Key, FL

What's nearby

  • Siesta Key Beach
    Siesta Key Beach
    2 min walk - 0.2 km
  • North America, United States, Florida, Miami-Dade County, Miami Beach, Ocean Drive
    Irma Beach
    2 min drive - 1.8 km
  • SiestaKey_StBonifaceEpiscopalChurchLabyrinth_6295832-2
    St. Boniface Episcopal Church Labyrinth
    2 min drive - 2.0 km
  • Siesta Key Farmers Market
    6 min walk - 0.6 km
  • Siesta Key Beach Playground
    20 min walk - 1.7 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.

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).

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Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 16 out of 18 reviews
Rating 8 - Good. 2 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

9.8

Cleanliness

9.8

Location

Reviews

Verified

10/10 Excellent

Robyn

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Bryan O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Stayed 4 nights in May 2025
Verified

10/10 Excellent

Art M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 6 nights in Aug 2024
Verified

8/10 Good

silvia r.

Liked: Cleanliness, check-in, communication, location

Great location and beach house

The TV in the pool did not worked and de AC in the 4th floor was so slow. the rest, perfect and amazing views.
Stayed 2 nights in Aug 2023
Verified

10/10 Excellent

Justin O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Beach Property

Tremendous property!! Beautiful views of the Gulf. Easily walkable to the beach. Large, spacious house. Great for big families!!!
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

William M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Aug 2025
Verified

10/10 Excellent

Genesis K.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

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.
Stayed 1 night in Nov 2022
Verified

10/10 Excellent

Walt B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

bday getaway with friends

This property was exactly as advertised! Everything was clean and worked well. Excellent location as well.
Stayed 5 nights in Oct 2022
Verified

10/10 Excellent

Lori M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 5 nights in Oct 2021
Verified

10/10 Excellent

Angie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 5 nights in Jul 2023
Verified

8/10 Good

Maria Arlen D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Jhana P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfectly big and beautiful

The home was lovely.
Stayed 2 nights in Feb 2022
Verified

10/10 Excellent

Christina F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 3 nights in Jan 2022
Verified

10/10 Excellent

James T.

Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Patrick G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Jan 2025