Condo

Penthouse with Sundeck, Private Access to Beach & 500ft to the Village

Photo gallery for Penthouse with Sundeck, Private Access to Beach & 500ft to the Village

An aerial view of a beach with clear turquoise waters and a sandy shore.
A modern bedroom with a large bed, bedside tables, a TV, and a view of the city.
A spacious living room with a large sofa set, a fireplace, and a television.
Rooftop sundeck with partial ocean views and sun loungers
A modern kitchen with blue cabinets, a central island, and a breakfast bar.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • The great outdoors

    Guests love the outdoor space here.
  • Games

    A rare find - enjoy a variety of games available on-site.
  • Centrally-located

    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks

    Near Siesta Key Beach
3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Balcony
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Washing machine
  • Onsite parking available

Explore the area

View map
Siesta Key, FL
  • Place, Siesta Key Beach
    ‪3 min walk‬
  • Place, Siesta Key Farmers Market
    ‪5 min walk‬
  • Place, Siesta Key Beach Playground
    ‪2 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪28 min drive‬

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Single Bunk Beds, 1 Single Bed and 1 Queen Futon

Common Spaces

1 Single Bed

2 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Dining area

About this property

Penthouse with Sundeck, Private Access to Beach & 500ft to the Village

Famous for its quartz sand and crystal-clear waters, Siesta Key’s beaches are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. This Gulf of Mexico barrier island is less than a 30-minute drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams—and with walkability to both the Beach and the Village, we’re confident this stay will help create unforgettable memories.

Siesta Key Dreams’ flagship vacation rental offers PRIVATE beach access via a gated, private path, a lush and modern 3 bed, 2 bath layout, and a rooftop sundeck!

Ideal for family and friend gatherings, the home accommodates up to 10 guests (8 adults and 2 children). The large, spacious floor plan flows from a welcoming living room to a dining area that seats 8, plus a modernized kitchen with stainless steel appliances. Just off the living room is a private, enclosed balcony with comfortable seating—perfect for shaded outdoor relaxing—with partial ocean views. The Main Bedroom also features partial ocean views, a luxurious king-size bed, and direct access to the enclosed balcony. The second bedroom has a king bed and looks out toward Beach Blvd. The third bedroom is designed with families in mind, offering a bunkbed with three twin-size mattresses (one pulls out from under the frame) and a queen-sized futon. There’s also a roll-away twin-sized mattress/bed for the common area.

Head up to the rooftop for a shared (with one other unit) sundeck and outdoor space with partial ocean and beach views—some of the best in Siesta Key Dreams’ portfolio. Siesta Key Dreams provides sun loungers and an outdoor couch, perfect for tanning and enjoying the Florida sun. Guests also receive beach essentials, including beach towels, umbrella, chairs, blanket, cooler, and a cart. When you’re ready for the water, pack up the cart, walk 20 steps, use the PRIVATE access point (key provided), and you’re on the 99% white quartz sand.

Need a break from the sun? Relax on the enclosed balcony, or head downstairs to the fully shaded front patio—great for people watching along Beach Road.

Stay connected with free high-speed WiFi, HD televisions equipped with live sports & extension channel options via DirecTV Stream, and electric appliances to keep your trip easy and comfortable.

Siesta Key Dreams always displays our exact address in our listings so you can see just how close you are to the beach and village. Unplug and explore—Siesta Village is less than a 3-minute walk from the Penthouse, with everything from cafes to fine dining, local shopping, and entertainment.

Beyond the stunning white quartz sand, Siesta Key beaches offer picnic areas, concession stands, and volleyball courts. Shallow, crystal waters plus year-round lifeguard protection make for a safe, relaxing escape, and being mere minutes from the ocean means you won’t miss those breathtaking sunsets. Just a 3-minute walk from the Penthouse brings you back to Siesta Village, where you’ll find dining and entertainment ranging from gourmet donuts, coffee, and seafood to award-winning steakhouses.

Parking can be tough to find, which is why this rental includes TWO private, reserved spaces at no additional cost (two vehicle max). The free Siesta Key Breeze Trolley also runs on the main roads outside your rental, operating 8 AM–10 PM, seven days a week.

Siesta Key Dreams strives to deliver “Unreasonable Hospitality”—service at the highest caliber, well above expectations. After you secure your vacation rental, our team will share clear expectations to help you prepare. If anything comes up upon arrival, a Guest Experience Manager who lives within the Siesta Keys area is available at a moment’s notice. We take pride in providing professional, personalized service to help make your stay truly unforgettable.

Included in your reservation are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & Keurig pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. For beach days, we provide beach towels, beach chairs, umbrella, blanket, cooler, and a cart for easy transport. Traveling with children? Complimentary cribs, highchairs, toys, silverware, and baby-monitors are available per request!

Shortly after booking, you’ll receive a link to book local services and experiences from vendors throughout the island.

When available, guests may request flexible booking options such as early check-in or late check-out. Siesta Key Dreams also offers baggage drop-off prior to check-in. You’ll be able to indicate your preferences in the link you’ll receive before check-in.

Guests will receive an electronic Rental Agreement with key terms and conditions, including our no-smoking policy. Guest verification is required just after booking and before check-in; you’ll receive the information after booking, and the process takes only a couple of minutes. This helps us maintain a safe environment for guests, neighbors, and employees.

Need more room? Siesta Key Dreams can rent you the entire building, which adds the second 3-bedroom condo.
Check Out: 10AM
Check In: 3PM
Quiet Hours: 10PM- 7AM
No smoking
Large Gatherings: Only guests associated with the reservation are allowed in the building and unit
Pets: No pets
Additional Details: See Vacation Rental Agreement for all details
Parking: 2 vehicle maximum

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House Rules

Check in after 3:00 PM

Minimum age to rent: 18

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

No pets allowed

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Smoking

Smoking is not permitted

Check Out: 10AM Check In: 3PM Quiet Hours: 10PM- 7AM No smoking

Important information

You need to know

Property # 3884972vb
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

About the area

Siesta Key

Located on the beach, this condo 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 and St. Boniface Episcopal Church Labyrinth. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and hiking nearby.
Map
Siesta Key, FL

What's nearby

  • Siesta Key Beach - 3 min walk - 0.3 km
  • Siesta Key Farmers Market - 5 min walk - 0.4 km
  • St. Boniface Episcopal Church Labyrinth - 2 min drive - 2.0 km
  • Siesta Key Beach Playground - 2 min drive - 1.7 km
  • Turtle Beach - 10 min drive - 8.9 km

Getting around

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

Restaurants

  • ‪Circle K - ‬8 min walk
  • ‪Gilligan's Island Bar & Grill - ‬3 min walk
  • ‪Siesta Beach Pavilion - ‬16 min walk
  • ‪Siesta Key Oyster Bar - ‬4 min walk
  • ‪Daiquiri Deck Siesta Key Village - ‬3 min walk

Frequently asked questions

Is Penthouse with Sundeck, Private Access to Beach & 500ft to the Village pet-friendly?

No, pets are not allowed at this property.

How much is parking at Penthouse with Sundeck, Private Access to Beach & 500ft to the Village?

On-site parking is available at the property.

What time is check-in at Penthouse with Sundeck, Private Access to Beach & 500ft to the Village?

Check-in begins at 3:00 PM.

What time is check-out at Penthouse with Sundeck, Private Access to Beach & 500ft to the Village?

Checkout is at 10:00 AM.

Where is Penthouse with Sundeck, Private Access to Beach & 500ft to the Village located?

Located in Siesta Key Village, this beachfront condo building is in the city centre and 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).

Reviews

10

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. 17 out of 18 reviews
Rating 8 - Good. 1 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

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing location!
Stayed 3 nights in Mar 2026
Response from VrboOwner on 9 Mar 2026
Thank you, and you all are welcome back anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and communication with Kyle.
Stayed 3 nights in May 2026
Response from VrboOwner on 19 May 2026
Thank you, such a cool picture from the private path to the beach!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The condo was in great shape. Family really enjoyed the thoughtfulness of the host providing a selection of coffees and snacks. The convenient location to Siesta Key Village was very nice. Beach was gorgeous.
Stayed 5 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location for shopping, bar hopping and distance to beach.
Stayed 4 nights in Sep 2025
Response from VrboOwner on 22 Sept 2025
Tamara, I am sooo pleased everything went well. I do enjoy the location as well :) I hope we see you again!!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was quick to reply and very accommodating. Location is perfect for walkability to town and of course to the beach.
Stayed 3 nights in Jan 2026
Response from VrboOwner on 16 Jan 2026
Awesome, I am so happy everything went well and I hope we see you again 😎
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was perfect for our girls weekend. It was very modern and had all modern conveniences. We love the sun deck up on the top, a nice feature for evening drinks and conversation. Highly recommend.
Stayed 3 nights in Mar 2026
Response from VrboOwner on 30 Mar 2026
Leslye, Thank you for this kind review. I am really happy everything went well and I hope we see you again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location - balances being close to beach and village all being walkable View of the ocean between houses a nice plus that we didn’t think we would like so much. Sitting on the porch being able to see the ocean was great for mornings or just taking break from everything / everyone
Stayed 4 nights in Feb 2026
Response from VrboOwner on 20 Feb 2026
Adeeb, thank you! I am pleased everything went well and appreciate the detailed review. I hope we host you again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great, contemporary property! Loved the sun deck and lanai. Host was very responsive.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 9 Dec 2025
Matt, I appreciate this review! I am pleased everything went well, and we hope to see you again!!!
Verified review

10/10 Excellent

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

Family vaca

Great location, easy access to beach and resteraunts. Comfortable and clean.
Stayed 3 nights in May 2025
Response from VrboOwner on 1 June 2025
Angie, thank you for this review, I am happy everything went well and I hope we see you all again 😁!
Verified review

10/10 Excellent

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

Great stay!

Great stay with my 2 adult children and 2 teens. Easy walk to the beach with sufficient equipment provided. So close to the village which made it great for easy shopping, eating etc!
Stayed 4 nights in Mar 2025
Response from VrboOwner on 2 Apr 2025
Beth, thank you for this review, I am glad everything went well and I hope we see you all again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic property. Easy walk to beach with private walkway to beach. Everything in siesta key village is walkable. Unit is upgraded and has everything needed to for a great stay. I will be coming back for another stay.
Stayed 3 nights in Sep 2025
Response from VrboOwner on 7 Sept 2025
Ryan, thank you! I hope we see you again 😎
Verified review

10/10 Excellent

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

Weekend Getaway

We loved everything about our stay here! Close to the beach and village! Excellent amenities and will stay here again! 10/10
Stayed 2 nights in Sep 2024
Response from VrboOwner on 18 Sept 2024
Lisa, thank you for this kind review. I am pleased that you all had a great time. I hope we can host you all again :)
Verified review

10/10 Excellent

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

Amazing Stay!!

We had such a great time in this unit. Easy access to the beach close to restaurants and bars. The unit was super nice with all the supplies we needed to cook. I definitely recommend staying in this unit. We will definitely be coming back.
Stayed 3 nights in Jul 2024
Response from VrboOwner on 6 Sept 2024
Thanks for the review, the location is a great aspect of this vacation rental :)
Verified review

10/10 Excellent

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

Our stay u SK

Penthouse was beautiful! Owner was very quick to respond and helpful!
Stayed 2 nights in Jul 2024
Response from VrboOwner on 3 Aug 2024
Dan, thanks so much for this review. You all are welcome back anytime!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
All good.
Stayed 9 nights in Mar 2026
Response from VrboOwner on 27 Mar 2026
Hello Clint, Our goal is 5 star service. I wish you would have notified us during your stay that you were not receiving that service level.
Verified review

10/10 Excellent

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

Great Beach Vacay

The property is beautiful and so close to the beach. Had everything we needed or wanted - full kitchen, washer and dryer, extra blankets, tons of towels, clean, and plenty of seating. Comfortable beds! Very close to great restaurants and shops. Check-in process was super easy. Owner/manager communicated with us regularly! Would recommend 100%!
Stayed 4 nights in Jul 2024
Response from VrboOwner on 7 July 2024
Zelda, thank you for the kind review. I hope you find us again!
Verified review

10/10 Excellent

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

Arrival bumpy but Manager made up for it

We had a few minor issues when we arrived. The hot water was not hot enough and the bathrooms were minimally dirty. Kyle immediately jumped on it. Maintenance came out immediately. Kyle went above and beyond by bringing us some additional bowls and measuring items (we cook more than most while on vacation). Overall, a truly great experience. Will very likely rebook for next year.
Stayed 6 nights in Jul 2024
Response from VrboOwner on 4 Sept 2024
Hi Lance, thanks for this review. I hope you all book again 😁
Verified review

10/10 Excellent

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

Best location beautiful luxury unit.

Location was amazing. Very Short walk to less hectic area of Siesta Beach. Very short walk to all the restaurants and shops of Siesta Village. Beautiful updated unit with high end kitchen, bathrooms and family room. Great patio and rooftop views. Quiet. Property Manger Kyle was amazing. Warned us about a potential issue with one of the bathrooms prior to the visit. Mid trip the issue resurfaced and he was on top of it despite the arduous task of finding someone to fix it months after a hurricane. Not only did he fix and address the problem but also reduced the rental fee due to the inconvenience to us. Would definitely stay here again. Great unit. Great location. Great owners and property management.
Stayed 5 nights in Mar 2025
Response from VrboOwner on 14 Mar 2025
Raj, thank you for this review. I am pleased everything went well! You all were great guests, I hope to see you all again 😁!

About the host

Hosted by Kyle Gaffney

Host profile image

Hello future guests!

I am pleased to share a portfolio of premium vacation rental properties in Iowa & Siesta Key, Florida. I've worked in the customer service sector for two decades and focus on providing excellence through people, product, and process. My vacation rental properties are specifically selected, to ensure that my guests have premium experiences at truly unique locations! I work remotely in Southern California and I handle all the electronic and phone communication with our guests. To provide localized support I have a great team, which includes a local Guest Experience Manager, operations, and cleaners. In addition, I spent time in all the properties and have stayed at the majority of them :)

A positive guest experience is a passion and I believe that our guests deserve to have great experiences that I hope will last a lifetime!

Why they chose this property

This Vacation Rental is in an area that is one of the most unique in all of Siesta Key. The access to the ocean is about a minute walk from this Vacation Rental, and the Siesta Key Village is only a couple minute walk. The neighborhood allows our guests to have a stress-free experience. The biggest decision our guests have to make is if they want to go to the beach or the restaurant :)

What makes this property unique

Location, location, location :) In addition to a truly unique location within Siesta Key, we provide a lot of extras and amenities that other vacation rentals charge for. When you stay with us, you receive a complimentary beverage, a beach-load-out, bathroom and care essentials, and high-end streaming service. Also, unique to Siesta Key Dreams, we have a Guest Experience Manager local to Siesta Key. Our goal is to provide "unreasonable hospitality," and we are here to do whatever it takes to ensure our guests have memories they can keep forever!

Languages:

English

Premier Host

They consistently provide great experiences for their guests

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