The Oceanview Penthouse 603 Oceanview Penthouse, 12-steps to Siesta Key's best beach access! Stunning views with floor-to-ceiling “movable' glass walls in master bedroom and living area. Just 3-min by trolley or bike (10-min walk) to Siesta Village. Remodeled in 2023. Free bikes and paddle boards. Communal lounging, alfresco dining, ping-pong, and Tiki bar below. Perfect for families and couples looking to relax, explore and repeat. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta
What Guests Love ∙ Ocean Views – southwest views of Gulf and sunsets through floor-to-ceiling windows ∙ Gulf Breezes – wall of windows folds for unobstructed ocean breezes day or night ∙ It's a Penthouse –no neighbors above or next to you and best views at property ∙ Beaches – 12-steps to access of Americas top beach, white sand and calm clear water ∙ Relaxing – safe easy access to outside attractions and lots of plus-space on site ∙ Sunsets –walk 30-seconds to best sunsets or just enjoy from your living room ∙ Island Trolley –picks up out front, free of charge to all attractions and welcome's drinks ∙ Activities – free bikes and paddleboards provided, scooter and golf cart rentals nearby ∙ Extra Spaces –ping pong room, alfresco dining-lounging, DIY tiki bar in the back ∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch ∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts ∙ The Memories – walk to all Siesta Key's top attractions and guaranteed fun for all
The Beach Our beach access is across the street, 12-steps, and is quieter and more private. Although one of the most desirable on the Siesta Key and has no parking available so isn't easy to access from rentals outside the neighborhood. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. A livelier beach scene with food, drinks and even a weekend drum circle is accessible a 5-to-10-minute walk south on the beach.
The Home Ocean view property contains just 3 units and was remodeled in 2022. The penthouse unit has the best views, sun and breezes. It also doesn't share a wall or ceiling with another unit. Floor to ceiling glass walls in master bedroom and living area create wide-open southwestern exposures. Glass wall is bifold design and fully opens for maximum ocean or sunset views and refreshing breezes day and night. Common areas include the ping-pong room, tiki bar, alfresco dining, and usually cornhole. Set on the Southern edge of Siesta Village and surrounded by tropical plants. Just 10-second walk to top beaches, and 3-minute golf cart or trolly ride (10-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 penthouse unit is 3BR and is two staircases from the ground. There is one large king bedroom, an ocean view queen bedroom, and a bunkroom with twin-over-full and twin-over-twin-bunks. Tempur-pedic rollaway beds are available with advance notice, and although the master bedroom is quite big, setting up by the window in the living room makes it the best sleeping area in the house. You can sleep up to 9 family style. Need more space? Ask about an additional unit nearby.
Beach Gear Provided We provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. 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.
History – There's no public parking in this area so, even though this is a gorgeous beach, it ends up being a little more private than most. When I was a kid growing up on Siesta Key, this beach access was called “Palm Island” and named after the island of the same name right at the end of the street. The island has a small bridge going to it and is literally a “heart shaped” island within the island of Siesta Key. When I was younger this was our lovers lane and, for me, it's still the spot to fall in love or rekindle an old flame.
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.
Our prices include all fees. No hidden fees.
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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
Onsite parties or group events are strictly prohibited
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 and a deadbolt lock
About the neighborhood
Siesta Key
Located in Siesta Key, this apartment is in the city center 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. 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 ecotours and cycling nearby.
Siesta Key Beach Playground - 12 min walk - 1.1 km
Siesta Beach - 12 min walk - 1.1 km
Siesta Key Farmers Market - 12 min walk - 1.1 km
St. Boniface Episcopal Church Labyrinth - 18 min walk - 1.5 km
Getting around
Sarasota-Bradenton Intl. Airport (SRQ) - 32 min drive
Restaurants
Siesta Beach Pavilion - 8 min walk
Circle K - 15 min walk
Siesta Key Snack Bar - 8 min walk
Gilligan's Island Bar & Grill - 11 min walk
Sun Garden Cafe - 14 min walk
Frequently asked questions
Is Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village! pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village!?
As of Jun 11, 2026, prices found for a 1-night stay for 2 adults at Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village! on Jun 14, 2026 start from $570, 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 Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village!?
Check-in begins at 3:00 PM.
What time is check-out at Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village!?
Check-out is at 10:00 AM.
Where is Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village! located?
This family-friendly Siesta Key apartment building is located by the sea, within 1 mi (2 km) of Siesta Beach and Siesta Key Beach. Crescent Beach is 2.2 mi (3.5 km) away.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Host was very welcoming and communicative and the place was perfectly comfortable, stocked, and functional. Amazing view!
Caleb S.
Stayed 3 nights in Dec 2025
Response from VrboOwner on Jan 16, 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
The property is located for easy access to the beach and close to the beach town either walking or by trolley. The place looks tired and the stairwell is awful.. stained carpets, bugs etc. However the living area is clean and comfortable. The air conditioning works well in the master bedroom, but struggles everywhere else during the day. Having 2 bathrooms is challenging if you are sleeping 10 people. They provide beach chairs, umbrellas etc, but some were broken so don’t count on them. The outside area was dingy and the ping pong room is not air conditioned and shared with 2 other units. Overall, the location is great, but the environment needs a makeover. We paid a lot, although it was memorial weekend and expected to be higher. The communication between the host was quick and helpful, but everything considered I would not stay here again.
rachel z.
Stayed 3 nights in May 2026
Response from VrboOwner on May 26, 2026
We sincerely appreciate this guest’s feedback and are sorry certain aspects of their stay did not meet expectations. Guest comments are important to us, as they help us continue improving both the property and the overall experience we provide.
We completely understand the concern regarding pricing during Memorial Day weekend. Holiday periods on Siesta Key are among the busiest times of the year, which significantly impacts rates. Guests who visit the week before or after often find prices substantially lower.
We also appreciate the comments regarding the carpet in the common stairwell. Due to the property’s location directly across from the beach and the relaxed, barefoot-style atmosphere many guests enjoy, the area experiences heavy foot traffic and sand exposure. While this naturally causes wear over time, we agree that the carpeting has become worn and is already scheduled for replacement.
Regarding the beach equipment, we are sorry if the guest felt it did not meet expectations. We do make an effort to provide a large selection of beach items for guests' use, and our team routinely removes and replaces anything that becomes damaged or worn.
The front bedrooms feature floor-to-ceiling glass with western exposure, offering beautiful natural light and stunning sunset views that many guests love. Thermal curtains are provided to help keep rooms comfortable; however, when left open during the afternoon and evening, those rooms can naturally become warmer due to the amount of direct sunlight they receive.
We truly value the guests’ stay and appreciate them taking the time to share their experience.
From a partner site
10/10 Excellent
Pete C.
Mar 2, 2026
GREAT STAY -- AWESOME HOST
Our stay was absolutely perfect. Our Dan not only keeps the property in great shape, but also keeps the beach equipment in great working order too. Makes for a very STRESS FREE stay...I forgot an additional roll away bed, and he had one dropped off before we got back from dinner the first day. He has a lot locations in Siesta Key. If you see he's the host, do not have any hesitation to book it.... he's prompt, thorough, and his entire operations runs like clockwork ....
Pete C.
From a partner site
10/10 Excellent
Brad C.
Aug 8, 2025
Great stay, great loction
Great stay, great location. The access to chairs, bikes, umbrellas, etc. was simply outstanding as travelers that didn't drive into town. Communication was great and the house was very clean. Thank you!
Brad C.
From a partner site
10/10 Excellent
Luis C.
Nov 21, 2024
Great place
Great place to stay they had everything we needed. It was very clean beds were great and the best part is it's right across the street from the beach
Luis C.
From a partner site
10/10 Excellent
Michael J.
Apr 21, 2025
Across the street from the beach!
Really enjoyed staying at this property. It was clean and well equipped including a full assortment of beach gear and beach toys. We would absolutely stay here again.
Beautiful apartment, one block across from a beautiful beach, clean and completely remodeled with all you need to have a wonderful vacation. We really enjoyed our stay there.
Ever M.
Stayed 3 nights in Jul 2022
Response from VrboOwner on Dec 18, 2022
Thank you. We hope you visit again soon. You're a repeat guest now and can call me at (888) 5-SIESTA if you need anything at all! Always happy to help.
Perfect location, great views, easy walk to the beach, and close to lots of great food. Perfect vacation for the laid back beach goer.
Melissa F.
Stayed 4 nights in May 2023
Response from VrboOwner on May 21, 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Roomy, clean, good location and comfy beds and linens
Would definitely come back,
Daniel was very accessible and accommodating.
Gary L.
Stayed 5 nights in Mar 2023
Response from VrboOwner on Apr 16, 2023
So glad you had a good time. We hope you come again soon! Just reach out to me "Daniel" at Gertrude Rentals the next time you need anything at all. Repeat guests never pay full price.
Loved the view and location. Short walk to all restaurants and shops. Very clean and owner very responsive.
Melissa A.
Stayed 4 nights in Feb 2023
Response from VrboOwner on Mar 16, 2023
I really appreciate your feedback! Let me know when you need another dose of Siesta Key. Love to have you back :) You're a repeat guest now and can call me at (888) 5-SIESTA if you need anything at all! Always happy to help. Thank you so much for choosing Gertrude Rentals!
From a partner site
10/10 Excellent
Stacia G.
Feb 13, 2024
wonderful vacay at the Penthouse!
Loved our short visit at the Penthouse! it was decorated beautifully and super close to all things Siesta whether it be the beach access or Siesta Key Village. Will consider staying here again!
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Great view ! Great stay ! Vey convenient location …..
Ann D.
Stayed 4 nights in Feb 2024
Response from VrboOwner on Mar 9, 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
The property was great! It was so nice to have all the beach toys available for our group. I would recommend this rental.
Ashley B.
Stayed 5 nights in May 2024
Response from VrboOwner on May 24, 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
maria B.
May 2, 2024
Perfect in every way!
Everything from location to accommodations were perfect! I always stay at a Gertrude rental when coming to siesta key because I know I can count on a personable experience with Dan being hospitable in every way!
Great location, walking distance to Siesta Village and also the beach. Very clean and great communication!
Highly recommend!
DOUGLAS F.
Stayed 3 nights in Feb 2024
Response from VrboOwner on Mar 4, 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
Such a great location for our girls trip. We were able to walk to the village for everything we needed. The house is well stocked and right across from the beach. Would definitely stay again!
kelly f.
Stayed 3 nights in May 2023
Response from VrboOwner on May 13, 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Very impressed, clean, and had everything we needed for our stay!
Wendy D.
Stayed 3 nights in Sep 2023
Response from VrboOwner on Oct 20, 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me at (888) 5-SIESTA. - Daniel Jones
Beautifully renovated home close to the village with restaurants and shopping. Also close to the beach access point to enjoy the sun and water and white sand. Perfect spot, house was clean and cozy. Loved the shared back area.
Meaghan J.
Stayed 2 nights in Jan 2023
Response from VrboOwner on Apr 17, 2023
So glad you had a good time. We hope you come again soon! Just reach out to me "Daniel" at Gertrude Rentals the next time you need anything at all. Repeat guests never pay full price.
From a partner site
10/10 Excellent
Michelle B.
Mar 19, 2024
Fabulous location
Fabulous location, walk across street to beach access. Walk to town for breakfast and dinner!! Very clean 3 BR, lots of amenities like free bikes and kayak, SUP, etc.
We will definitely be back!!!
Michelle B.
From a partner site
10/10 Excellent
Scott H.
May 16, 2024
603PH
This is a really good location. Close to the beach and a short walk to the village. Overall a nice place to stay. We will be back.