Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village

Top rated by guests
Ocean view Siesta Key vacation rental in the village across from beach access.
Eat-in kitchen with all major and minor appliances, and lots of counter space.
Eat-in kitchen with all major and minor appliances, and lots of counter space.
Spacious game room with ping pong table.
Sunny tropical view of Siesta Key Beach Access #10.
review stars
10Outstanding
(62 Ratings)
"Host was very welcoming and communicative and the place was perfectly comfortable, stocked, and functional. Amazing view!"
Caleb S.
Don't miss out! Price and availability may change
10 / 10
Outstanding(62 Ratings)

Apartment in Siesta Beach

10 guests · 3 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this apartment rental

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.

Amenities at Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village

Non-smoking
Pets allowed
Family friendly

Map of Siesta Beach


Ratings and reviews

10 / 10
Outstanding(62 Ratings)
10 / 10Outstanding·Dec 2025
Host was very welcoming and communicative and the place was perfectly comfortable, stocked, and functional. Amazing view!
10 / 10Outstanding·Aug 2025
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!
10 / 10Outstanding·Apr 2025
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.
10 / 10Outstanding·Mar 2025
This property provided everything we could have hoped for during our stay. Essentially right on the beach, designated parking (no public parking around there which translates to a quieter beach section), and everything we needed to set up and spend the day in the sand. The property itself was great with epic retractable glass doors facing the beach. Due to the prime location, there was some noise from passing cars during the night so a white noise machine or similar might be helpful if anyone is sensitive to that. We received regular, fulsome communications and were responded to immediately if we had any questions or concerns. Huge thanks to Dan and the Gertrude team for a wonderful vacation.

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FAQs

Is parking included with this apartment?

Parking is not specified as an available amenity at Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village. For more information, we encourage you to contact the property about where to park.

Is there a pool at this apartment?

We didn’t find pool listed as an amenity for this apartment. It may be worth double checking if a pool is important for your stay.

Is Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village pet friendly?

Yes! This apartment is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.