NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach
Onyx Penthouse - Siesta Key Vacation Rental Resort-like penthouse only 500ft to private beach access and Siesta Keys whitest sand! Amenities include - fully appointed pool area, alfresco dining and lounging, in-house elevator, open sun and covered private balconies, and 4-hole putting green. This is a top floor unit with 14ft ceilings and wraparound ocean view balcony (partial view)! Perfect for families or couples wanting to experience Siesta Key's top attractions without sacrificing space and comfort. Book a vacation now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta *NEW LISTING!! Please read the other Gertrude Rentals reviews. We are very proud of them!
What Guests Love ∙ Private Balconies – covered and open sun options off bedrooms, living, dining ∙ The Beaches – 1-min walk to Siesta Key's whitest sand and calmest water ∙ Pool – heated with sun-shelves, chaises, dining, and grill (1-unit shares) ∙ Views – private westerly wraparound balcony with partial ocean and sunset views ∙ Relaxing – Open floor plan, larger rooms, and balconies off every bedroom ∙ The Putting Green – 4-holes, no green fees, course record: 06 (1-unit shares) ∙ Sunsets –walk 1-min to worlds best sunsets or just enjoy from balconies or pool ∙ Free Trolley – 1-min walk to free trolley destined for island's top shopping, dining ∙ Restaurants – walk bike or ride trolley to 30 dining options within 1-2 miles ∙ Point of Rocks Reef – walk snorkel or paddle searching shells, dolphins, manatees ∙ Memories and Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream
The Beach Our beach access is only a 500ft walk on a quiet lane and has the whitest sand and calmest water on the island. You can walk south 1-mile to explore Point of Rocks Reef or just swim or wade to any nearby sandbar. The water is shallow and clear with white quartz-sand tide-pools perfect for sleeping drinking or playing. You'll go from the water and sand, back your unit for lunch or dinner without putting on your shoes.
The Location You aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities this property will deliver what they are searching for. At the house you'll enjoy a semiprivate pool (1-unit shares), poolside grilling and dining, 1600 ft.² of private balconies, and multiple alfresco lounging areas perfect for your bonding and relaxing enjoyment. Outside the house it's a 1-min walk left to the best beach on the island and 1-min walk right to the free trolley stop to all the top attractions on the island including two marinas, 30 bars and restaurants, shopping, live music, and countless eco-adventures.
Bedroom Details This is a large 3BR, you can sleep up to 8 family style, and every bedroom opens to a private balcony. The master suite has a king bed with bath en-suite. Bedrooms #2 and #3 have king beds and share a convenient guest bathroom. The living area features a full sized Murphy bed and two twin Tempur-pedic rollaway's are available with advance notice.
Beach Gear Provided We provide beach towels, chairs, carts, 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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Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
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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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Siesta Key
Located in Siesta Key, this condo 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 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 ecotours nearby.
Siesta Key, FL
What's nearby
Siesta Key Beach - 1 min walk - 0.2 km
St. Boniface Episcopal Church Labyrinth - 14 min walk - 1.2 km
Siesta Key Beach Playground - 15 min walk - 1.3 km
Siesta Key Marina - 2 min drive - 1.7 km
Crescent Beach - 2 min drive - 2.1 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 33 min drive
Restaurants
Siesta Beach Pavilion - 17 min walk
Siesta Key Snack Bar - 18 min walk
Captain Curt's Crab & Oyster Bar - 2 min drive
Dunkin' - 4 min drive
The Sniki Tiki - 2 min drive
Frequently asked questions
Does NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach?
As of 10 April 2026, prices found for a 1-night stay for 2 adults at NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach on 30 June 2026 start from NZ$1,437, 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.
Is NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach pet-friendly?
Yes, pets are allowed at this property.
How much is parking at NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach?
On-site parking is available at the property.
What time is check-in at NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach?
Check-in begins at 3:00 PM.
What time is check-out at NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach?
Checkout is at 10:00 AM.
Where is NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach located?
This family-friendly Siesta Key condo building is located by the sea, within 1 mi (2 km) of St. Boniface Episcopal Church Labyrinth, Siesta Key Beach and Crescent Beach. Siesta Key Beach Playground and Siesta Key Marina are also within 1 mile (2 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Enjoyed the stay with my husband - just the relaxing getaway we needed!
Jennifer L.
Stayed 5 nights in Oct 2025
Response from VrboOwner on 23 November 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Adam H.
13 November 2025
Wonderful Stay
Our group reserved both the upper and lower floors and had a wonderful stay. Quick walk to the beach and in a quiet location.
Beautiful house, beautifully finished. Everything we could need for the weekend! Thank you so much for making it easy for us.
Steve c.
Stayed 3 nights in Jan 2026
Response from VrboOwner on 23 February 2026
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Nova H.
30 September 2025
Perfect place for my group.
Perfect place for my group. Convenient access to the beach with a very short walk. Beautiful home would love to stay here again.
Nova H.
From a partner site
10/10 Excellent
Nova H.
30 September 2025
Beautiful home and wonderful family to work with! Highly recommend this gorgeous condo!!
Beautiful home and wonderful family to work with! Highly recommend this gorgeous condo!!
Nova H.
From a partner site
10/10 Excellent
Nova H.
30 September 2025
Was a fabulous stay!
The place was so well kept with plenty of supplies in the kitchen including some of the extras that make life easier so you can enjoy vacation like coffee, salt & pepper, paper towel & laundry soap. All the beach supplies you could want too. And, the pool and putting green were such a hit with our boys!!! Thanks for everything! Was a fabulous stay!
Our stay was exactly as described. The unit is gorgeous, clean, steps from the beach, with lots of wonderful amenities. The outdoor shower was an unexpected and very welcome surprise when returning home from the beach before taking a dip in the pool! There were a few hiccups with checking in and supplies at the unit, but this was handled quickly and didn’t take away from our trip. Would definitely recommend this property!
Alyssa S.
Stayed 7 nights in Apr 2025
Response from VrboOwner on 3 May 2025
Alyssa and her family were wonderful guests. The communication was prompt, gracious and appreciative. They took great care of our condo and treated it as if it was their own. Our entire experience with them was positive and I would gladly host them again and again and again!
From a partner site
10/10 Excellent
Nova H.
30 September 2025
Best condo I've ever been to.
My first reaction was WOW! So beautiful and open and clean. There were snacks for us and they had soap, shampoo, lotion and more. TVs in every room. TVs on the deck TV outside by the pool. Great wagons and chairs for the beach. Great lawn furniture for by the pool. It was private. Kitchen was awesome. We had a great time! Scott responded within minutes every time I had a question. Met some of the family. So friendly. We are booked for next year! Best condo I've ever been to.
We had the most wonderful Thanksgiving stay at Scott's property in Siesta Key! The location is perfect – just a short walk to the beach and village! This brand new property provides everything you need for a day at the shore, including beach chairs and a wagon. The pool in the backyard was our personal oasis, complete with a TV and grill – perfect for relaxing after a day in the sun.
The house itself was stunning. The wrap-around balconies provided beautiful views, and the full kitchen had everything we needed for cooking. The king beds were incredibly comfortable, and we loved having TVs in every room. Scott was an amazing host, so attentive and quick to respond to any questions we had, making our stay even more enjoyable.
We will definitely be returning!
Lexi S.
Stayed 4 nights in Nov 2024
Response from VrboOwner on 4 December 2024
Lexi and her family were absolutely wonderful! They left the property in pristine condition, treating it with the utmost care and respect. Communication was smooth, and it was clear they truly enjoyed their stay. We'd happily welcome them back again, again, and again and highly recommend them to other hosts. Thank you for being such thoughtful and responsible renters!