Penthouse with Sundeck, Private Access to Beach & 500ft to the Village
Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.
The Siesta Key Dream’s flagship vacation rental features PRIVATE access to the beach via a gated private path, a lush and modern 3 bed, 2 bath layout, and a rooftop sundeck!
This rental is perfect for family and friend gatherings and can accommodate up to 10 guests(8 adults and 2 children). This large, spacious floor plan connects a welcoming living room, a dining room that seats 8, and a modernized kitchen featuring stainless steel appliances. In your living room, you’ll find a private, enclosed balcony with comfortable seating that is perfect for shaded, outdoor entertainment and includes partial ocean views. Your Main Bedroom has partial ocean views, contains a luxurious king size bed and has direct access to the enclosed balcony. The second bedroom has a king bed and looks out towards Beach Blvd. In the third bedroom, you’ll find a bunkbed that has three-twin size mattresses(one pulls out from under the frame) and a queen sized futon, perfect for families with children! We also have a roll-away-twin-sized mattress/bed for the common area.
Outside on the roof-top, you’ll have a shared (with one other unit) sundeck and outdoor space that provides partial ocean and beach views – the best in Siesta Key Dream’s portfolio. Siesta Keys Dreams provides lounge chairs and tables, perfect for tanning and hanging out in the Florida sun. Our guests receive a beach-load-out, which includes beach towels, umbrella, chairs, blanket, cooler and a cart. If you’re looking to soak up the sun and clear waters, pack-up the cart, walk 20-steps, use the PRIVATE access point (key provided) and you are now in the 99% white quartz sand.
Want to get out of the sun, the enclosed balcony is a great choice or head downstairs to the front of the building, and hang-out on the front patio, fully shaded and great for people watching on Beach Road.
Siesta Key Dreams is happy to provide free, high-speed internet & Wi-Fi, HD Televisions equipped with live sports & extension channel options via free streaming services, and electric appliances so you will not miss a beat.
Siesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach and village. Unplug and explore your surroundings, such as the Siesta Village which is less than a 5-minute walk away down Beach road! From cafes to fine dining, local shopping and entertainment, you will certainly find what you need.
In addition to the stunning, white quartz sand, the beaches of Siesta Keys offer picnic areas, concession stands, and volleyball courts. The shallow, crystal water and year-round lifeguard protection makes each beach a safe and relaxing escape. Having your property mere minutes away from the ocean means that you will certainly witness breathtaking sunsets. A 3-minute walk from the beach reveals Siesta Village, which offers a wide-range of dining and entertainment options from gourmet donuts, coffee, and seafood to award-winning steakhouses.
We recognize that parking can be difficult at times to locate, which is why this rental comes with TWO private, reserved spaces at no additional cost to you. Alternatively, we offer an exclusive upgrade which includes a golf cart rental for easy travel and access to all the top tourist spots around town. The Siesta Key Breeze Trolley also operates on the main roads outside your rental, which is free for all riders and operates 8 AM - 10 PM, seven days a week!
Siesta Key Dreams wishes to provide you with `Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives within the Siesta Keys area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable.
Included within your reservation and rental cost are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & a Keurig-pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrella, blanket, cooler and a cart to transport your items easily! Traveling with your children? We offer complementary cribs, highchairs, toys, silverware, and baby-monitors available per request!
Shortly after you secure your vacation rental, you will receive a link where you can book local services experiences provided by vendors throughout the island. Siesta Key Dreams provides golf-carts to rent and mid-stay services such as cleanings, and linen changes.
When available, guests can request flexible booking with early check-in or late check out options. Siesta Key Dreams also offers baggage drop-off prior to your check-in time. You will be able to indicate your preferences in the link you will receive prior to check-in.
Guests will receive a Rental Agreement via email that provides common details about our terms and conditions, such as our no-smoking policy. Before you check-in, and just after booking, we require guest verification. You will receive information after booking and the process only takes a couple minutes. This allows us to provide a safe location for our guests, neighbors, and employees.
Looking for a larger space? Siesta Key Dreams can rent you the entire building which adds the second 3-bedroom condo.
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Check Out: 10AM
Check In: 3pm
Quiet Hours: 10pm - 7AM
No smoking
Large Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams
Important information
You need to know
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
This property uses eco-friendly cleaning products
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 near 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 hiking and cycling nearby.
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
Irma Beach - 2 min drive - 1.8 km
St. Boniface Episcopal Church Labyrinth - 2 min drive - 2.0 km
Siesta Key Beach Playground - 2 min drive - 1.7 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 32 min drive
Restaurants
Siesta Beach Pavilion - 16 min walk
Siesta Key Snack Bar - 16 min walk
Circle K - 8 min walk
Gilligan's Island Bar & Grill - 3 min walk
Sun Garden Cafe - 7 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 does it cost to stay at Penthouse with Sundeck, Private Access to Beach & 500ft to the Village?
As of 8 May, 2026, prices found for a 1-night stay for 2 adults at Penthouse with Sundeck, Private Access to Beach & 500ft to the Village on 2 Aug, 2026 start from S$756, 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.
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?
This family-friendly Siesta Key condo building is located by the ocean, within 1 mi (2 km) of Siesta Key Farmers Market and Siesta Key Beach. St. Boniface Episcopal Church Labyrinth and Irma Beach 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.
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.
Leslye P.
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!
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!
Beth P.
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!
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.
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.
Luis P.
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 :)
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%!
Zelda M.
Stayed 4 nights in Jul 2024
Response from VrboOwner on 7 Jul, 2024
Zelda, thank you for the kind review. I hope you find us again!
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.
Raj S.
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 😁!
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.
Lance O.
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 😁
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
Adeeb S.
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!
About the host
Hosted by Kyle Gaffney
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