Gertrude's Siesta | Oceanview Penthouse | 1 min walk to Beach Path + Huge Terrace
Now available New Years (had cancellation)...Penthouse Aqualina Ocean view luxury penthouse. Breathtaking views from private 400sqft terrace! 20 steps from grounds to Americas best beach. Impeccably and fully renovated in 2023. 4-minute golf cart or free trolley ride to shopping dining and entertainment in Siesta Key Village. Travelers agree, this is the top ocean-view rental on Siesta Key! Book an escape today! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta
What Guests Love ∙ Breathtaking Ocean and Siesta Key Beach Views - from every room except the laundry and bath ∙ Beachside - located only 20 steps from grounds to Siesta Key's award-winning beaches ∙ The Terrace - 400sqft private terrace open airy, high above everything below ∙ Sunsets - walk 1-min to beach or watch the world's best sunsets from the terrace ∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch ∙ The Fun - 3-min free trolley ride to Village and live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts ∙ Activities - bikes, paddleboards, scooter and golf cart rentals nearby ∙ Island Trolleys - stops right out front, free of charge to all Siesta Key points ∙ Memories - walk to all the island's top attractions and guaranteed fun for all
The Beach Our beach has a quieter beach in front and to the right plus a lively popular crowd 50 yards south. It is a top spot on Siesta Key for sunsets and on Sundays the world-famous Siesta Key Drum Circle happens 100 yards down the beach. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.
The Home Large 1BR home 1000 square feet and fully remodeled in 2023. Beautiful décor and thoughtful amenities throughout. Its level is unmatched on Siesta Key. Set on the Southern edge of Siesta Village. Just 30 steps to top beaches, and 3-minute golf cart or trolly ride (15-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.
Bedroom Details This ocean view property it's on the 4th floor with an elevator. There is one large king bedroom, and a queen sleeper in the living room. Some say the views in the living room make it the best sleeping area in the apartment. You can sleep up to 4 family style.
Beach Gear Provided We provide beach towels, chairs, and umbrellas. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide "snorkeling gear" but this and anything you need can be rented or purchased nearby.
Household Items Provided We provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.
What to Bring It's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.
Post Booking Support We understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time.
Terms Payments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.
Travel Insurance If you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.
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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 and a deadlock
About the area
Siesta Key
Located in Siesta Key, this apartment is near theme parks and 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. Travelling with kids? Consider Mote Marine Laboratory & Aquarium, or check out an event or a game at Stardust Event Center. Discover the area's water adventures with kayaking and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
St. Boniface Episcopal Church Labyrinth - 12 min walk - 1.0 km
Siesta Key Farmers Market - 17 min walk - 1.5 km
Crescent Beach - 4 min drive - 4.1 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 31 min drive
Restaurants
Siesta Beach Pavilion - 6 min walk
Siesta Key Snack Bar - 6 min walk
Circle K - 19 min walk
Gilligan's Island Bar & Grill - 15 min walk
Sun Garden Cafe - 18 min walk
Frequently asked questions
Is Gertrude's Siesta | Oceanview Penthouse | 1 min walk to Beach Path + Huge Terrace pet-friendly?
No, only service animals are welcome at the property.
How much does it cost to stay at Gertrude's Siesta | Oceanview Penthouse | 1 min walk to Beach Path + Huge Terrace?
As of 19 Apr 2026, prices found for a 1-night stay for 2 adults at Gertrude's Siesta | Oceanview Penthouse | 1 min walk to Beach Path + Huge Terrace on 2 June 2026 start from AU$599, 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 Gertrude's Siesta | Oceanview Penthouse | 1 min walk to Beach Path + Huge Terrace?
On-site parking is available at the property.
What time is check-in at Gertrude's Siesta | Oceanview Penthouse | 1 min walk to Beach Path + Huge Terrace?
Check-in begins at 3:00 PM.
What time is check-out at Gertrude's Siesta | Oceanview Penthouse | 1 min walk to Beach Path + Huge Terrace?
Checkout is at 10:00 AM.
Where is Gertrude's Siesta | Oceanview Penthouse | 1 min walk to Beach Path + Huge Terrace located?
This family-friendly Siesta Key apartment building is located by the sea, within 1 mi (2 km) of Siesta Key Beach Playground and Siesta Key Beach. St. Boniface Episcopal Church Labyrinth and Siesta Key Farmers Market are also within 1 mile (2 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
A beautiful one bedroom condo! We already miss our lovely view of the ocean. Fantastic view and perfect location to beach and village. Gertrude rentals are so easy to work with!
William H.
From a partner site
10/10 Excellent
Jim A.
10 Jan 2024
Great Stay and Location
We had a great week and the condo was perfect. It was very clean, had everything we needed and the location was great. The beach right across the street was huge and was far enough away from the public parking that it was not crowded. The trolley stop right outside of the building was also very convenient.
Jim A.
From a partner site
10/10 Excellent
Anita S.
9 Aug 2025
Outstanding Vacation Rental
Gertrude Rentals was the most outstanding company for our vacation rental! Immediate responses to any questions and kind staff. The condominium was perfect and had everything we needed. It was so clean and gorgeous and we got an excellent rate. We didn't want to leave Siesta Key. I have never experienced such wonderful customer service. We have traveled a lot and this company was the best! All information was clear and precise regarding check-in, door codes, WiFi, and even the TVs! Thank you Gertrude Rentals!
Anita S.
From a partner site
10/10 Excellent
Jimmy S.
3 Feb 2025
Great
Best rental I have ever stayed in. View from the deck was awesome
Gertrude could not have been any better or nicer!
There is nothing not to like.
Jimmy S.
From a partner site
10/10 Excellent
Laurel S.
27 Feb 2025
Stunning
The penthouse has scenic views of the beach, with spectacular evening sunsets! The space is beautifully decorated and has everything you need for your stay; from kitchen wear and linens to beach gear. The Gertrude group is highly responsive, they make the rental and checkout process easy and they are dedicated to providing a relaxing vacation experience.
We were thrilled with the beautiful space and stunning views!
Laurel S.
From a partner site
10/10 Excellent
Bob G.
30 July 2024
Beautiful, comfortable and clean. Wonderful!
The only problem with our stay was that it was too short! The unit was beautiful, comfortable, clean and had everything we needed. The location was great! Right across from the beautiful public beach, not far from the village. Fun vibe without being overly crowded. Public transportation or bike/cart rental makes it easy to get around. Would definitely book this place again.
Bob G.
From a partner site
10/10 Excellent
Eliza F.
25 Oct 2024
AMAZING stay!
There are too many good things to say about this rental i stayed in with Gertrude. I visited shortly after the hurricanes and they were so accommodating. When one of our places had damage Daniel worked quickly to find an alternative for us to stay in. The location was perfect, the unit had everything we could need and it was clean. Siesta key is still beautiful as ever, as places have opened back up and are seeking traveler business! I will definitely rent with Gertrude Rentals in the future!
Eliza F.
From a partner site
10/10 Excellent
Michael G.
2 Apr 2024
Great stay in the Penthouse
Great accommodations. Directly across the road from Siesta Beach! The condo came with everything we needed. It also came with beach chairs, umbrella and a beach cart to take everything to the beach for the day. The balcony was fantastic. Large with table and chairs and 2 chaise lounges. You felt like you were on the beach. A truly enjoyable experience. I highly recommend Gertrude Rentals.
Michael G.
From a partner site
10/10 Excellent
Leigh V.
21 Aug 2024
Great
The location of this beautifully decorated property is perfect for access to the beach, pickle ball courts, and walking distance to the village for live music and great food! The unobstructed view of the beach is nice to wake to every morning—right off of a large private deck! There was also a trolley stop outside the building to ride into the village if that is your choice of transportation. The king size bed was very comfortable and the personal fans at the bedside were a nice touch. Clean, quiet and very nicely furnished condo. We will definitely rent here again!
Newly redone and decorated,tastefully furnished. Had trouble working tv and help arrived immediatel
Great property. Perfect for two adults unfortunately wife’s brother joined us for one night. A little crowded for three only comment were that needed reading lights on bedside table. Probably a $25 item or less
gordon n.
Stayed 4 nights in Jan 2024
Response from VrboOwner on 26 Jan 2024
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Rogelio R.
1 Dec 2023
Wow! Just what we needed!
It was expensive, the owner gave us a small discount, but so worth it. I can't wait to go back. So close to the beach, but I wish I spent more time in the unit enjoying the view and a beautiful furnishings. We took the trolley to the village. It picked up right out front. It was only about a two minute ride to the restaurants. Well worth it! Just what we needed!
Rogelio R.
From a partner site
10/10 Excellent
Nancy W.
9 Dec 2023
Wonderful trip
From my first conversation with Dan, I was extremely impressed. Dan helped find me the perfect rental for our visit to Siesta Key,
The condo, true to the beautiful photographs was amazing. It was clean, updated, and decorated beautifully. Dan was available before and throughout our vacation to answer questions and offer suggestions as we needed. He was just a phone call away!
Renting with Gertrude was an easy process that I would highly recommend! I plan to return and wouldn't go anywhere else but to Dan for my rental needs'
Thank you for everything! You are rockstars!
Nancy W.
Stayed 5 nights in Dec 2023
Response from VrboOwner on 15 Dec 2023
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you!
From a partner site
10/10 Excellent
erin m.
9 Apr 2024
Penthouse Paradise
We spent spring break in this fabulous rental, alongside our teenage daughter. The location was PERFECT! The beach was right outside your door. We appreciated the beach cart, chairs, umbrella and ample beach towels that were provided. The balcony and view were spectacular. Everything about this place was amazing-the decor, cleanliness, kitchen amenities, location, view-just to name a few! It was also so close to the village, and the trolley stopped right at the corner! As a first time visitor to Siesta Key, I am so glad that we found this place and we had the most memorable Spring Break. Dan was amazing to work with and was quick to respond to any questions. I highly recommend this rental!
erin m.
From a partner site
10/10 Excellent
Lance S.
22 Feb 2024
Terrific location, great penthouse
We recently spent a (very) long weekend at the Aqualina. The location is excellent, across the street from beach access #11, so very easy to go for walks in the morning, or grab chairs and supplies for a day of lounging. The apartment is about 1 mile from the village center so its a very reasonable walk into town, but with the trolley stop at the corner of the building, you can just walk out and hop the next trolley or call FrogHop and they will come grab you (for free!) right away.
The apartment itself is very nice. The 65" TV supports AirPlay 2, so easy to stream from your Apple devices. The kitchen is well stocked with ample tools and appliances to cook if you are so inclined. The view toward the beach is a full, wall to wall set of sliding glass doors and since you are on the top floor, you get the view 24x7. You can seal off the doors with a slider to provide shade if you are visiting when it is crazy hot. The deck has two lounge chairs and a table with four chairs - great for entertaining with a view.
The bed seems new and was comfortable. The unit comes with a HE washer and dryer combo. The bathroom is recently remodeled, and while relatively small (one sink), shower stall, no tub - it was clean, functional and did the job.
While there is a sleeper sofa, for any long term rental, it is really best suited for two people given the main bedroom and bathroom arrangement. Its on the top (fourth) floor so lots of stairs but there is an elevator just outside the unit. (we never heard any elevator noise or traffic).
A quality penthouse apartment in a solid location. Highly recommended.