Condo

🦩 Charming 2BR Condo Pool View ~ Siesta Key Bay Oaks🦩

Photo gallery for 🦩 Charming 2BR Condo Pool View ~ Siesta Key Bay Oaks🦩

A living room with a sofa, coffee table, and a TV.
A kitchen with a built-in stove, oven, and coffee maker. There is a dining area with a table and chairs in the background.
A bedroom with a bed, a dresser, a vanity with a mirror, and a window with curtains.
A swimming pool with a stone border, surrounded by buildings with balconies and palm trees.
A park with a picnic table and benches, a walking path, and a body of water with a dock in the background.

Reviews

9.2 out of 10
Wonderful

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Cue up the fun
    One of the few properties with an on-site pool table.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Siesta Key Beach

Popular amenities

  • Balcony
  • Swimming pool
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View in a map
Sarasota, FL
  • Place, Siesta Key Beach
    ‪5 min walk‬
  • Place, Safe Harbor Siesta Key
    ‪14 min walk‬
  • Place, Crescent Beach
    ‪14 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪28 min drive‬

Rooms & beds

2 bedrooms (sleeps 8)

Common Space

1 Double Sofa Bed

Guest

1 Queen Bed and 1 Single Bunk Bed

Master

1 King Bed

2 bathrooms

Guest

Bathtub or shower · Toilet

Master

Bathtub or shower · Toilet

Spaces

Porch or lanai
Kitchen
Balcony
Dining area

Add dates for prices

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Bay view living area in Siesta Key vacation rental near the beach.
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  • Pool
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  • Kitchen
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9.8 out of 10, Exceptional, (27 reviews)
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About the area

Siesta Key

Located in Siesta Key, this condo is near the beach. 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. Looking to enjoy an event or a game while in town? See what's going on at Robarts Sports ARENA, or consider a night out at Sarasota Fairgrounds & Robarts Arena. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and cycling nearby.
Map
Sarasota, FL

What's nearby

  • Siesta Key Beach - 5 min walk - 0.4 km
  • Safe Harbor Siesta Key - 14 min walk - 1.2 km
  • Crescent Beach - 14 min walk - 1.2 km
  • St. Boniface Episcopal Church Labyrinth - 20 min walk - 1.7 km
  • Siesta Key Beach Playground - 4 min drive - 2.4 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 31 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Siesta Beach Pavilion - ‬3 min drive
  • ‪Captain Curt's Crab & Oyster Bar - ‬13 min walk
  • ‪Hooters - ‬4 min drive
  • ‪Daiquiri Deck South Siesta Key - ‬13 min walk

Frequently asked questions

Does 🦩 Charming 2BR Condo Pool View ~ Siesta Key Bay Oaks🦩 have a pool?

Yes, this property has a pool.

How much does it cost to stay at 🦩 Charming 2BR Condo Pool View ~ Siesta Key Bay Oaks🦩?

As of 1 Nov 2026, prices found for a 1-night stay for 2 adults at 🦩 Charming 2BR Condo Pool View ~ Siesta Key Bay Oaks🦩 on 28 Nov 2026 start from £1,233, 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 🦩 Charming 2BR Condo Pool View ~ Siesta Key Bay Oaks🦩 pet-friendly?

No, pets are not allowed at this property.

How much is parking at 🦩 Charming 2BR Condo Pool View ~ Siesta Key Bay Oaks🦩?

On-site parking is available at the property.

What time is check-in at 🦩 Charming 2BR Condo Pool View ~ Siesta Key Bay Oaks🦩?

Check-in begins at 4:00 PM.

What time is check-out at 🦩 Charming 2BR Condo Pool View ~ Siesta Key Bay Oaks🦩?

Checkout is at 10:00 AM.

Where is 🦩 Charming 2BR Condo Pool View ~ Siesta Key Bay Oaks🦩 located?

Situated by the sea, this condo building is within a 5-minute walk of Gulf Intracoastal Waterway and Siesta Key Beach. Crescent Beach and Safe Harbor Siesta Key are also within 1 mile (2 km).

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 24 out of 35 reviews
Rating 8 - Good. 6 out of 35 reviews
Rating 6 - Okay. 5 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 0 out of 35 reviews

8.6/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.2/10

Communication

9.6/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very beautiful,clean property, excellent condition and location
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay! Pool was a hit with the kids! Plenty of essentials: beach towels, dishes, cookware, beach toys etc. We had a great stay!
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Great pool and nice quiet condo area. We loved the screened in balcony. Wonderful time!
Stayed 7 nights in Apr 2023
Verified review

10/10 Excellent

Liked: Check-in, location, listing accuracy
Disliked: Communication

Has it all!

The condo was well appointed and convenient to the beach, village and mainland.
Stayed 8 nights in Dec 2024
Response from VrboOwner on 10 Jan 2025
We would love to have you back :-)
Verified review

10/10 Excellent

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

Amazing Vacation

We spent 7 wonderful days at Oak Bay on Siesta Key. the place very clean and cozy. the beach nearby, the divine pool and very quiet. I recommend that you spend your vacations there it is a magnificent place
Stayed 7 nights in Jul 2021
Response from VrboOwner on 10 Dec 2024
You are a part of the flock now! Let us know how we can help make more vacation memories happen in the future 850-4-pinkie. Always happy to help :-)
Verified review

10/10 Excellent

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

Great Property

Condo was immaculate and a perfect fit for my family of five!!
Stayed 7 nights in Jul 2022
Response from VrboOwner on 10 Dec 2024
You are a part of the flock now! Let us know how we can help make more vacation memories happen in the future 850-4-pinkie. Always happy to help :-)
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice location, walkable to beach and restaurants or free shuttle available. The condo is fixed up cute with newer appliances. There was no hand soap when we checked in, only a bottle of hand sanitizer in one bathroom. Kitchen cabinets and drawers had crumbs and some food splatter from previous guests. Otherwise everything else was clean and satisfactory. Lanai closet was stocked well with anything you would need for the beach
Stayed 4 nights in Apr 2026
Verified review

6/10 Okay

Liked: Cleanliness, check-in
No beach ascess. Not enough pool chairs
Stayed 28 nights in Feb 2026
Response from VrboOwner on 15 Mar 2026
Yes this condo is not advertised with private beach access but the public beach access is right down the street at Crescent Beach. There is also a free trolley that will also take you to any of the 16 public beach access points. We had 4 chairs in the unit for your use and these can be used at the pool or anywhere needed. Your check-in info indicated they were in the closet on the balcony. Hope to see you again soon! Pinkie:)))
Verified review

10/10 Excellent

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

Very nice condo close to everything on Siesta Key!

We loved staying at this nice condo on Siesta Key! Excellent location with a short drive or bicycle ride to Siesta Key Village shops & restaurants. This condo has everything you'll need for a nice vacation. Communication with the owners/managers was excellent too.
Stayed 9 nights in Dec 2019
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
This location was very good and the condo was well kept. The beach equipment was extensive which we really appreciated!!I would have given it 5 stars however, I found the kitchen amenities to be lacking. The bakeware and sheet pan were rusted, and in need of replacement. The listing advertised a Keurig, which was not there, and the overall organization of the drawers and cabinets is very lacking. I actually had to go to Walmart and buy a usable sheet pan and baking pan to make basic canned cinnamon rolls and biscuits. Other than that it was a fantastic place and I would just recommend to the owners to update the kitchen, utensils, and items for usage.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

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

Lovely

The property was clean and had everything we needed
Stayed 7 nights in Jul 2023
Response from VrboOwner on 10 Dec 2024
You are a part of the flock now! Let us know how we can help make more vacation memories happen in the future 850-4-pinkie. Always happy to help :-)
Verified review

10/10 Excellent

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

Bay Oaks

Great location. We thought we would have beach access across the street, but had to go to Siesta Beach about a mile drive away. Pool was great, as was the intracoastal dock area. The beds were very comfortable. We would probably stay there again.
Stayed 28 nights in Feb 2023
Verified review

10/10 Excellent

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

Wonderful property

Condo is exactly as pictured. We really enjoyed sitting out on lanai enjoying the early morning and evenings. Convenient trolley stop in front of condos. Condo was well equipped and had closet with beach chairs, coolers and fishing gear. Fantastic family vacation
Stayed 7 nights in Jun 2022
Verified review

10/10 Excellent

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

Great Condo.

The condo was exactly what was booked. Great amount of space and cutlery as there were 8 of us. Fantastic amount of beach equipment plus a wagon to tow it. Short distance to really anywhere on Siesta. Overall very happy with this experience and will Be booking again!
Stayed 7 nights in Jul 2023
Response from VrboOwner on 10 Dec 2024
You are a part of the flock now! Let us know how we can help make more vacation memories happen in the future 850-4-pinkie. Always happy to help :-)
Verified review

6/10 Okay

Liked: Check-in, communication, location, listing accuracy

Great location, average place to stay

We booked this property based on location, size and reviews. I’ll start with the good. Great location. Close to beach access. Right off the main thoroughfare through Siesta Key. The property has a large amount of beach equipment (chairs, coolers) and toys for the kids. Having a washer and dryer was really nice since we
Stayed 8 nights in Jun 2024
Verified review

10/10 Excellent

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

Family vacation

Was fine pool is really nice pier is nice,carpet could use some attention. Was plenty of room for us. Need some new frying pans with lids.
Stayed 17 nights in Apr 2023
Verified review

10/10 Excellent

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

Bah oak gem!

The unit provided all that we needed and then some! We’ve vacationed on siesta key for 15 years and this was our second time at bay oak. Great property with a great pool and plenty of other amenities. This specific unit had plenty of beach equipment and was well stocked. My only criticism is that the bathrooms could use a bit of TLC. Thanks very much for allowing us to stay and we’ll likely be back!
Stayed 11 nights in May 2025
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Its ok

Condo grounds are lovely,enjoyed the fishing pier. Unit could have been cleaner,but had all that we needed there
Stayed 34 nights in Jan 2024
Verified review

10/10 Excellent

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

Seista

Easy check ..in .on 4th floor ..elevator was down entire week ......had to use the one on other side of blg...
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

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

May 2024

Really enjoyed the condo and pool. We never got hot water at the kitchen sink and when we pullef out the sofa sleeper was disappointed that tge sheets were very dirty seeming as though someone had eaten in bed very crumby. Didn't keep us from enjoying our time, just an FYI
Stayed 7 nights in May 2024
Response from VrboOwner on 10 Dec 2024
You are a part of the flock now! Let us know how we can help make more vacation memories happen in the future 850-4-pinkie. Always happy to help :-)
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy

Bay Oak

The condo itself was beautiful, clean and well decorated. I understand 2 major storms ravaged the area last fall, but the grounds and vegetation were not in great shape. We looked at other condo properties that were close that's were in terrific shape. Disappointed their wasn't a gas grill to BBQ. Location was minimum 10 walk to the beach, thought we could cut across the street, but understand all private property on the beach side of the road. Overall good experience, pool was nice too. Many young people for March break, and nobody on site in the office to deal with the kids making noise and vulgar language.
Stayed 14 nights in Apr 2025
Verified review

6/10 Okay

Disliked: Cleanliness, communication, listing accuracy

Wanted to love it!!

The location was close to Siesta key public beach area which was nice. The layout of the condo worked well for our family of five. After checking in your are asked to report any problems with the condo, so I did. What would have made it better... if the screen door wasn't broken, the filthy air filter had been changed, like I asked, instead of being told they would take care of it next week, after we had left, the 3 tubs and 2 hanging bags of overdue damp rid water had been refreshed so the musty smell would have been a little easier on the nose, the kitchen blender wasn't broken, and the elevator did not have a delinquent sign posted on the it for 2 out the 7 days, we were on the 4th floor. I could not find a manger onsite the entire week. So disappointed. We will not stay at this location again.
Stayed 7 nights in Jun 2025
Response from VrboOwner on 16 Jul 2025
Hello! Thank you for coming and for this feedback. I have looked back through our correspondence and see nothing from you. At any rate I do apologize for any issues during your stay. Please come back to see us as we have taken care of these things! Pinkie:)))
Verified review

10/10 Excellent

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

family vacation

We stayed for 12 nights in early June. Overall the stay was pleasant. Just a couple of issues but resolved quickly. Pro's: the public transportation on the beach was easy and a welcome amenity. 3-4 different ways to get around and drivers work on tips. (would personally recommend the FrogHop) Beach was beautiful and an easy walk out to the water. The pool was wonderful and the beach/pool extras from the condo were appreciated (wagon, umbrella, noodles etc)The bunk beds were a plus for the grandkids. Beds were basically comfortable, Con: Even though the beach was directly across the street there was no access and the listing saying it was 10–15-minute walk was slightly inaccurate and would have been a very hot walk. But we had our own vehicle and access to the public transportation. The building was definitely older, and the elevator was slow, but grounds were neat. I would recommend staying on the 2-4 floors. Some of the first-floor condos were directly near the garbage and in the heat, there was a definite odor. It was too hot to sit on the lanei, no breeze as the unit faced the pool, which was located interiorly. Other than the beach access the listing is accurate. Be sure to check out turtle Beach as well. I would rent again, good for families.
Stayed 12 nights in Jun 2025
Verified review

8/10 Good

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

Overall ok

Overall, it was a good stay. Furniture and decorations are in good taste and appeared to be good quality with some wear and tear (the pull out sofa is a little saggy). Dishwasher is large and quiet, and washer and dryer worked well. The apartment is bigger than I expected and our family of 7 didn't feel crowded in it. Plenty of beach towels, toys, and cooking species. It did feel like a home away from home. However, one toilet had a broken handle when we arrived and was never fixed during the week of stay (we flashed the toilet by manually flipping the water tank). The AC/Furnace thermostat was on and off several times during the stay and didn't get fixed. The room temperature was fine, my family were not picky, and I am just worried to be billed for fixing things that we didn't break. Also, there is a 10-minute walk to the public access to the public beach (unless you take the free bus). It is different from what Google maps tells you. Google doesn't know that most accesses to the public beach is gated and guarded by private properties. Property manager answered to my questions promptly and nicely, but didn't fix any of my complaints.
Stayed 7 nights in Dec 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay. The apartment was very clean, well organized, and had everything we needed. Check-in was quick and easy, and we did not experience any problems during our stay. The location was great, and everything was exactly as described. If I have the opportunity, I would definitely come back next year. I highly recommend this property.
Stayed 4 nights in Jul 2026
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