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

10.0 (56 Reviews) |   Pet Friendly   3 Bedrooms  2 Bathrooms  10 Guests  Stay&Play
Siesta Key Apartment | Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village!

3 Bedroom Apartment in Siesta Key

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 is 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.

Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village! is located in Siesta Key. Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village! provides accommodation, featuring Air Conditioner, Parking, View, among other amenities. This Apartment features Air Conditioner, Parking, View, to make your stay a comfortable one.

Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village! has 3 Bedrooms , 2 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Apartment because of the excellent services rendered by the owner or manager of this Apartment, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Apartment has a friendly neighborhood, and the Siesta Key has interesting places to visit. If you want to learn more about the Apartment in Siesta Key, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • TV
  • View
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Guest Services
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 3:00 pm contactless check-in available minimum check-in age: 21
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Pets allowed service animals are welcome, and are exempt from fees
Smoking Policy Smoking is not permitted
Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation
 
Siesta Key, 34242, USA

What Our Guests say 500 + Reviews

Apr 21, 2025 09:25:50 AM
Summary: 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.
Michael J. Michael J.
Mar 9, 2025 01:04:25 AM
Summary: 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.
Min S. Min S.
Dec 31, 2024 02:59:56 AM
Summary: The location was great. The bikes, kayaks and beach chairs were great. The carpet up the steps was not clean it needs to be replaced. The space was good. Thanks
Keri W. Keri W.
Dec 27, 2024 09:25:08 PM
Summary: Nice VRBO that our family enjoyed over the Christmas holiday. The facility was neat, clean and overall all that was promised on the website. When we return to Siesta Key this will be the first on our list to return to! Our only suggestion is the carpet on the stairways needs help. It probably suffered during the repairs from the two hurricanes earlier this year.
Charles M. Charles M.
Nov 21, 2024 01:00:56 PM
Summary: 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. Luis C.
Jun 26, 2024 11:22:32 PM
Summary: We had a wonderful time in the clean, bright, well-stocked penthouse condo right across from an uncrowded beach access (but still super easily walkable to the public beach)! Dan was so responsive - emailing me back near immediately, and also reassuring me that we *truly* didn't need to do anything to the condo prior to check-out. He even responded to a quick power outage on the key, and checked in when the system noted one of us was forgetting the door unlock code! Having all the towels, beach chairs, umbrellas and WAGONS right there and ready for us was wonderful. It was an experience we won't forget, and really appreciate!
Skye H. Skye H.
May 23, 2024 05:43:07 AM
Summary: 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. Ashley B.
May 16, 2024 11:07:54 AM
Summary: 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.
Scott H. Scott H.
May 7, 2024 11:11:40 AM
Summary: We had a great time in the beautiful penthouse at Siesta Key. Daniel responded quickly to any questions. The beds were comfortable. The kitchen had all that we needed. The beach umbrellas, chairs, and wagons were so helpful and the items like the paddleboards and kayaks added to the fun! The walk to the beach was 5 minutes. We were right on the Trolley line so a ride into town was easy to catch. Thanks for the great accommodations!
Patty S. Patty S.
May 2, 2024 11:09:46 AM
Summary: 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!
maria B. maria B.

FAQ's

Is this Siesta Key apartment pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Siesta Key apartment have a swimming pool?

No, this Siesta Key apartment does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Siesta Key apartment?

Best-rates for the Siesta Key apartment starts from $1,067 per night with includes Air Conditioner, Parking, View, Ocean View, Balcony/Terrace, Bedding/Linens, Guest Services, Child Friendly, Pet Friendly, Wellness Facilities, Entertainment, Internet, TV, Security/Safety, Fireplace/Heating, Barbecue/Outdoor Cooking, Kitchen, Oceanfront, Sports/Activities, Laundry StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Siesta Key apartment a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this apartment Good or guests have recommended them suitable for families. As reported by the owner or manager, the apartment has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Siesta Key apartment wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Siesta Key apartment has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Siesta Key apartment?

Based on the information reported by the owner or manager, the Siesta Key apartment indicates 1 day stay policy at this apartment. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Siesta Key apartment?

Based on the information reported by the owner or manager, details for the cancellation policy for the Siesta Key apartment are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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