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Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by The Bay & Key Collection

Photo gallery for Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by The Bay & Key Collection

Exterior
Outdoor dining
Terrace/patio
Interior
Living area

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms3 bathroomsSleeps 6

Popular amenities

  • Private pool
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View in a map
Siesta Key, FL
  • Place, Siesta Key Farmers Market
    ‪6 min walk‬
  • Place, Siesta Key Beach
    ‪9 min walk‬
  • Place, Irma Beach
    ‪1 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪27 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Kitchen
Garden
Dining area

About this property

Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by The Bay & Key Collection

**The property is a monthly rental, but please check with us for availability, as we can accommodate shorter stays if the rest of the month is not booked**
This lovely, fully updated CANAL front pool home is a 3-bedroom, 3-bathroom property that sleeps six. Located on a quiet cul-de-sac just one block from the Siesta Key Village and the best beach in the country! Access to the private pool is just off the living area and the primary bedroom.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 868625vb
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, a first aid kit and a deadlock

About the area

Siesta Key

Located on the waterfront, 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. Looking to enjoy an event or a game while in town? See what's happening at Stardust Event Center or Ed Smith Stadium.
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Map
Siesta Key, FL

What's nearby

  • Siesta Key Farmers Market - 6 min walk - 0.6 km
  • Siesta Key Beach - 9 min walk - 0.8 km
  • Irma Beach - 1 min drive - 1.1 km
  • Siesta Key Beach Playground - 3 min drive - 2.4 km
  • Crescent Beach - 6 min drive - 5.8 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 32 min drive

Restaurants

  • ‪Siesta Beach Pavilion - ‬4 min drive
  • ‪Siesta Key Snack Bar - ‬4 min drive
  • ‪Circle K - ‬4 min walk
  • ‪Gilligan's Island Bar & Grill - ‬9 min walk
  • ‪Sun Garden Cafe - ‬6 min walk

Frequently asked questions

Does Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by The Bay & Key Collection have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by The Bay & Key Collection pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by The Bay & Key Collection?

On-site parking is available at the property.

What time is check-in at Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by The Bay & Key Collection?

Check-in begins at 4:00 PM.

What time is check-out at Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by The Bay & Key Collection?

Checkout is at 10:00 AM.

Where is Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by The Bay & Key Collection located?

Located in Siesta Key Village, this holiday home is within a 15-minute walk 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 55 out of 65 reviews
Rating 8 - Good. 8 out of 65 reviews
Rating 6 - Okay. 2 out of 65 reviews
Rating 4 - Poor. 0 out of 65 reviews
Rating 2 - Terrible. 0 out of 65 reviews

9.6/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Daniel C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved this house and location! It was so clean when we arrived and we even had a little goodie basket to welcome us. So nice! We can’t wait to spent many more vacations in this home.
Stayed 12 nights in Aug 2025
Verified

10/10 Excellent

Carrie R.

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

Always a great stay!

This was our third stay and every time it’s fantastic! Great location, beautiful home and all the amenities we need for the week.
Stayed 8 nights in Aug 2023
Verified

10/10 Excellent

Suzanne P.

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

paradise

the house was spotless upon arrival! the neighborhood was so quiet and peaceful. the owner was great at responding to questions that I had. Id defiantly stay again!
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Mary R.

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

Perfect spot!

Within walking distance to beach, shops and restaurants. Everything is very clean and updated.
Stayed 7 nights in Oct 2023
Verified

10/10 Excellent

John T.

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

Wonderful time

The house was very clean and east access to village and beach.
Stayed 56 nights in Dec 2023
Verified

10/10 Excellent

Taryn S.

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

Great location

Home was very clean and perfectly located. The shed offered many toys and beach accessories and the home was well stocked with everything we needed. We would definitely return!
Stayed 7 nights in Sep 2022
Verified

10/10 Excellent

Chris S.

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

Awesome

Can't wait to go back
Stayed 8 nights in Sep 2022
Verified

10/10 Excellent

Valerie R.

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

Family vacation

We love staying at thia location because it is cloae to the village so everything is walkable. This hone is well equipped with everything you need to have a wonderful stay. Our kids had plenty of space to spread out and the rest of our family stayed a few streets over so we could walk back and forth. We would love to stay here again!
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Andrew and Jennifer L.

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

Spring Break 2023

We had the best time! The house is so nice. Easy walks to many places: shops, restaurants, grocery, beaches, yet also a really quiet, peaceful neighborhood. Loved having our own pool as well. Would most definitely stay here again.
Stayed 5 nights in Mar 2023
Verified

8/10 Good

Cindy L.

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

Beach Getaway With Good Friends

Enjoyed Siesta Key and all it had to offer. A wonderful time was had by all. ❤️
Stayed 7 nights in Mar 2023
From a partner site

8/10 Good

Carrie R.

Beautiful home with nice amenities

This was our 5th stay at Sunnyside Up. The updates after the hurricane are beautiful. We enjoy the pool but were surprised by all the weeds this year around the pool. There was a new lock on the front door that worked every other use. However overall our stay was great. We typically reserve the next year while staying but due to the increased price we are considering other options.
Verified

10/10 Excellent

Stephen S.

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

Enjoyed the stay

The property met our needs very well. A couple of small items. The bath towels could use an upgrade. An upgrade of the TP and larger kitchen trash bags are also recommended.
Stayed 7 nights in Dec 2019
Verified

10/10 Excellent

jeff l.

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

Second time and third trip planning

Awesone place with kids , incredible location, house has lots of needed items from everyone leaving things behind for others to use. Fishing in canal out back a hoyse is spotless with separate bath and master bedroom for Grandpa--me. Highly Rec.
Stayed 9 nights in Apr 2023
Verified

10/10 Excellent

Willard A.

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

Great place for families

The location and home are fantastic. Check in and out was easy. Enclosed pool was enjoyed by everyone. Would have been nice to have had one kayak to use on canals as we had to rent and fool with pickup and drop off. The house really only handles easily five people or six if one of the persons is say under 5. The one sofa is useless. We just put cushions on floor for our sixed. Definitely recommend for families.
Stayed 7 nights in Apr 2023
Response from VrboOwner on 3 Aug, 2023
Hi, I'm glad you enjoyed your stay. I will look into having a kayak available. The 3rd bedroom is great for a child and there is a blow up mattress available. The couch in the extra room is a full size pull out bed. The other bedrooms have a king bed and a queen bed.
Verified

8/10 Good

Carol H.

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

Dissatisfied

Everything was fine except the pool should have been heated.
Stayed 7 nights in Oct 2021
Response from VrboOwner on 3 Aug, 2023
Hi, The pool is heated. I'm sorry you weren't aware. The property manager could have turned it on for you or my pool guy Jason. Stephanie
Verified

10/10 Excellent

Miranda F.

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

Favorite house at Siesta Key, will stay again!

My family (myself, husband, 2 kids ages 8 and 12) stayed at this house. We’ve been coming to Siesta Key every summer for 4 years and this house is our favorite so far! Very clean inside and out! We loved the location...we walked to the village every evening for shopping and dinner. We did not walk to the beach, we drove to beach access 7 daily. I loved that the pool and patio area is screened in but there is also a connecting patio area without a screen which is great for enjoying the sun. The neighborhood was quiet and calm during our stay. The only complaint from my family was that only 1 bedroom out of the 3 had a tv. We will definitely be back to this house when we return to Siesta Key!
Stayed 8 nights in Jul 2021
Response from VrboOwner on 3 Aug, 2023
Hi Thank you ! I'm so glad you enjoyed your stay. I'm putting a new tv in the master this week. Come back and visit. Stephanie
Verified

8/10 Good

Penny W.

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

Our Stay

The property was great! The layout, the pool and the outside area. I was surprised there was blue painters tape covering a crack on the toilet seat in the King bed room and nothing was said about the disposal not working in the kitchen. The other thing was the fact that we made the reservations through VRBO but was contact many times by a rental group asking about when we were checking in and out. They were polite but it was just weird. We would stay again, we are pretty low key and wasn't going to compline about the toilet or the disposal. We love VRBO and have used it many times and will again!
Stayed 7 nights in Jun 2021
Response from VrboOwner on 3 Aug, 2023
Hi, Penny, We are so sorry! I had ordered a new toilet seat and it had not arrived before your visit and has since been taken care of. I was told by my management team that the garbage disposal was working. We will verify that and address it immediately. We would love to have you back. As you can see throughout or history, we have had very positive reviews and issues such as these should never occur. I have a management group running the property to help with check in and any maintenance issues. We will be sure that such circumstances are avoided in the future. Thanks for the feedback.
Verified

8/10 Good

Maggie C.

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

Great location

The house was very nice. Each bedroom had a separate bath. The shower in the front was not working. We didn’t want workers there repairing on our vacation so made due and let owners know after. We were told we should have called property managers as it is not broken just difficult to turn on. If that is the case they should either replace or post specific instructions. The place was great but this is why I gave 4 stars.
Stayed 7 nights in Apr 2022
Response from VrboOwner on 3 Aug, 2023
Hi, It was a pleasure hosting you. I appreciate your feedback. The controls are a little unusual. I plan on putting instructions for future guests. Thank you! Stephanie
Verified

10/10 Excellent

Jim B.

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

Siesta Key Bliss

We greatly enjoyed our stay at this property, which was our 7th stay in Siesta Key. The house is on a very quiet residential street, and on one of the Siesta Key canals. The house was very clean and well maintained. Nice, comfortable furniture and beds. The outdoor eating, sitting and pool areas were great places to hang out and enjoy meals. All of the essentials were at the house and available for use. Appreciated the fact that the house had bikes and beach toys and items available for use. The artwork on the walls and other personal effects made the house feel quite homey. We greatly appreciated the fact that the house is on one level, which made it easy to watch the kids while they used the pool, which is screened in, an added benefit. The house’s proximity to the Village was a definite plus. We hope to be back again in the future.
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Penny W.

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

Great place

We have stayed at this property in the past and it is always a great time. We were surprised on Thursday with an 8 am ring of the doorbell as there was a crew there to install an irrigation system in the front yard. It was a large crew with several vehicles that took up the road and driveway. Luckily we all were able to shower before the water was shut off and we had already planned on a ride share that day so we didn't have to get the car out of the driveway. They were polite and didn't give any trouble other than starting early and taking up space. We would have liked to know that they were coming. That was the only hitch. We would stay again.
Stayed 7 nights in May 2023
Response from VrboOwner on 3 Aug, 2023
Hi, I apologize for the inconvenience. We had been trying to get this done for more than two months. We weren’t sure of the exact time and day they were coming. Hope you had a great stay and will come back to see us.
Verified

6/10 Okay

Jennie R.

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

Cold pool, needs better cleaning

The check in process was easy, the house was in a great location. When we were there it was a little cool and we were hoping to use the pool daily, however it was much too cold to get in. I did reach out to the rental service, they increased it slightly but still was no where near warm enough. I even offered to pay an additional fee for a higher temp, but this was declined. So the pool I paid for was never used. I have never had this issue when renting a home with a pool. The keurig machine water reservoir was full of mold, which we cleaned the first morning. I did not take a photo of this. Within the first few days the toilets all had a dark moldy ring at the water level (it was only 2 people using 2 bathrooms, but they looked filthy). I was not pleased with the overall experience and would not rent this house again. For the price I expected more. (I do have photos of the toilets)
Stayed 7 nights in Nov 2021
Response from VrboOwner on 3 Aug, 2023
In the hundreds of guests that we have been pleased to host, you can count the negative responses on one hand. This was a challenging renter and we did our best to accommodate her wishes but it was still not enough. Had we been given a notification or sent pictures, we would have corrected the issues. The pool temperature was set to 84 to 86 degrees. With temperatures in the 50's it is very hard to keep the pool warm. We did our best to accommodate Jennie. We have an excellent cleaning crew and we conduct our own inspections prior to the guests arrival. We want our guests to have a wonderful stay at Sunnyside Up Cottage. Stephanie
Verified

6/10 Okay

Verified traveller

Liked: Cleanliness, check-in, communication, location

Nice location - could def use some upgrades

We recently stayed with two couples and a 1 yr old. The house has a sunken living room that made us all trip several times. Baby included. There’s no markings around the sunken floor to make you aware. The pool/patio area is very run down. The patio furniture is terrible. The box is filled with moldy/musty toys & such. There’s two gravity chairs but they were so old and seats completely ripped we couldn’t sit on them. There’s also only one lounger -that was plastic & uncomfortable - and the patio table & 4 chairs had the powder coating peeling off every time we sat in them & onto us. For us we wanted to be outside the most - the outdoor area just lacked everything. It was not comfortable at all. The pics made it look so much better. There’s also no pool alarms on the sliding doors and no child/baby gate by pool so our daughter couldn’t be out with us. (She’s walking now). We didn’t trust it. We thought this was a vacation home rule that needed to be followed everywhere. Location was close to the village. We walked most nights to dinner & for coffee in the mornings. The house could def use some upgrades. We felt the pics are from years prior. For the price, location, etc it just was lacking to us. Plus lacking some important safety features.
Stayed 7 nights in Aug 2022
Response from VrboOwner on 3 Aug, 2023
Dear Lindsay, Thank you for choosing to stay with us during your visit to Siesta Key, Ascendia Property Management and the property owner take great pride in ensuring that every guest has an amazing experience. We are very concerned (and a bit confused) about your review as we never heard from you during your stay. Your review is the first to mention the pool area was anything less than pristine. I have ordered a new dining table and chairs as well as 2 new loungers. We appreciate your feedback and wish you the best.!
Verified

10/10 Excellent

Lyudmila B.

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

Wonderful property! Great location!

Beautiful peaceful location! My family loved the area. Spacious house had everything we needed. Pool was amazing! Good time had by all! Thank you! Mila
Stayed 9 nights in Oct 2022
Verified

10/10 Excellent

Michael C.

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

Great House

We stayed right after Hurricane Ian. Owner was very responsive as was the property manager. House is great and location was spectacular. Private yet very convenient.
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

Antonios K.

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

Great place for family!

The house was very nicely updated. Plenty of room and a great location. Walking distance to anything you’d want to do in siesta key. Siesta key beach was also one of the nicest beaches our family has visited. We would return and would love to stay at the house again!!! Thanks
Stayed 7 nights in Aug 2022

About the host

Hosted by Stephanie Roberts

Host profile image
We moved to Siesta Key a few years ago. Our summer home is in Indianapolis. We absolutely love it here and we know you will too. Nick, our son, is a sophomore at Purdue University where he is studying Mechanical Engineering. Stephanie is an avid painter ( you will see many of her pieces in the house) and often goes to the beach and sets up her plein air easel and creates some wonderful things. Tim loves to golf and fish and Sarasota fits that bill to a T.

Why they chose this property

Sunnyside Up Is the name we gave the home as a reference to Its happy yellow color and the beautiful sunshine that you will enjoy there. The location is just perfect as it is a block to the wonderful restaurants and shops in the Village and a short bike ride to the beach. Avenida De Paradisio (or Avenue of Paradise) is a very apt name for this quite street with great neighbors and lovely tropical Fauna. The pool Is surrounded by palm trees and birds of paradise inside the pool enclosure and it the perfect place to relax with a book and the kids will simply not want to get out of the pool.

What makes this property unique

Canal and Pool home
Private Pool fully enclosed
Two Master Bedrooms plus a guest room and pull out sofa sleeper
Beautiful yard and plantings
Great deck area with comfortable furnishings
Located right on one of the nice Siesta Key canals

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