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
Our prices include all fees. No hidden fees.
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Sundeck with Ocean View, Private Access to Beach & 500ft to the Village
Siesta Key Village
Sundeck with Ocean View, Private Access to Beach & 500ft to the Village
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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
About the neighborhood
Siesta Key
Located on the beach, this condo is in Siesta Key Village, a neighborhood 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. Traveling 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.
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
Crescent Beach - 7 min drive - 5.5 km
Getting around
Sarasota-Bradenton Intl. Airport (SRQ) - 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 does it cost to stay at Penthouse with Sundeck, Private Access to Beach & 500ft to the Village?
As of Sep 24, 2026, prices found for a 1-night stay for 2 adults at Penthouse with Sundeck, Private Access to Beach & 500ft to the Village on Dec 6, 2026 start from $505, 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?
Onsite 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?
Check-out 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 center 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 mi (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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.
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 Mar 30, 2026
Leslye,
Thank you for this kind review. I am really happy everything went well and I hope we see you 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
Stayed 4 nights in Feb 2026
Response from VrboOwner on Feb 20, 2026
Adeeb, thank you! I am pleased everything went well and appreciate the detailed review. I hope we host 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!
Stayed 4 nights in Mar 2025
Response from VrboOwner on Apr 2, 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.
Stayed 3 nights in Jul 2024
Response from VrboOwner on Sep 6, 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%!
Stayed 4 nights in Jul 2024
Response from VrboOwner on Jul 7, 2024
Zelda, thank you for the kind review. I hope you find us 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.
Stayed 6 nights in Jul 2024
Response from VrboOwner on Sep 4, 2024
Hi Lance, thanks for this review. I hope you all book 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.
Stayed 5 nights in Mar 2025
Response from VrboOwner on Mar 14, 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
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