Apartment

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

Family-friendly apartment in Siesta Key with a water park

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

Relax on the balcony with comfortable chairs and enjoy views of the Gulf and tropical landscape.
Spacious balcony overlooking the Gulf and tropical surroundings. A serene spot to sip coffee, watch the sunrise, or enjoy the island vibe.
Enjoy the lively Siesta Key Village scene with restaurants, tiki bars, and entertainment just a short walk away.
Relax in a cozy living area with modern furnishings and windows framing Gulf views.
Open living room with coastal décor, comfortable seating, and floor-to-ceiling windows.

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Parking available
  • Air conditioning
  • Dryer
  • Washer
  • Outdoor space

Explore the area

View map
  • Place, Siesta Key Beach
  • Place, Crescent Beach
  • Place, Lido Beach
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Single Bunk Beds

Common Space

2 Double Sofa Beds

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Office
Balcony
Separate dining area
Dining area

About this property

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

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.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

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 in the city centre 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 Jim Neville Marine Preserve, or check out an event or a game at Stardust Event Center. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Siesta Key, FL

What's nearby

  • Siesta Key Beach - 2 min walk - 0.2 km
  • Siesta Key Marina - 4 min drive - 4.1 km
  • Shell Beach - 4 min drive - 3.8 km
  • Crescent Beach - 5 min drive - 4.1 km
  • Lido Beach - 21 min drive - 18.4 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 32 min drive

Restaurants

  • ‪Siesta Beach Pavilion - ‬8 min walk
  • ‪Siesta Key Snack Bar - ‬8 min walk
  • ‪Circle K - ‬15 min walk
  • ‪Gilligan's Island Bar & Grill - ‬11 min walk
  • ‪Siesta Key Oyster Bar - ‬12 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.

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!?

Checkout 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 Key Beach Playground and Siesta Key Beach. Siesta Key Farmers Market and St. Boniface Episcopal Church Labyrinth are also within 1 mile (2 km).

Reviews

10

Exceptional

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy
Rating 10 - Excellent. 53 out of 56 reviews
Rating 8 - Good. 3 out of 56 reviews
Rating 6 - Okay. 0 out of 56 reviews
Rating 4 - Poor. 0 out of 56 reviews
Rating 2 - Terrible. 0 out of 56 reviews

Reviews

10/10 Excellent

Ever M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

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.
Stayed 3 nights in Jul 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Stacia G.

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!

10/10 Excellent

Ashley B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacay

The property was great! It was so nice to have all the beach toys available for our group. I would recommend this rental.
Stayed 5 nights in May 2024

10/10 Excellent

Melissa A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved everything about this place!

Loved the view and location. Short walk to all restaurants and shops. Very clean and owner very responsive.
Stayed 4 nights in Feb 2023

10/10 Excellent

Julie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent location for the beach

Lovely condo. Short walk to the beach.
Stayed 3 nights in Apr 2023

10/10 Excellent

kelly f., Where do you live?

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location!

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!
Stayed 3 nights in May 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Michelle B., Summit, NJ

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!!!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Peter C.

Another Awesome Vacation

This was 2nd year staying at this location. For one reason - location and the over the top accommodations of the property. The host has everything you need for an easy going vacations - beach chairs, wagon, towels, laundry.. and the location can not be beat - ACROSS FROM THE BEACH ACCESS

10/10 Excellent

Natalie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Business Strategy Off Site

Great location, clean and spacious!!
Stayed 2 nights in Jan 2023

10/10 Excellent

Jose O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Siesta Key Dream

A truly beautiful gem adjacent to the Gulf Coast. My family loved it and we are looking at returning to the same location. Staff was professional and attentive to questions and concerns. Military Friendly !!
Stayed 3 nights in Jun 2023

10/10 Excellent

Mark B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great

Great
Stayed 3 nights in Jan 2023

10/10 Excellent

Josh C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing house

This house has a fantastic location across the street from the beach and only a mile from town. We walked to and from dinner every-night and used the complimentary bikes everyday to explore the island- get coffee at Mojo's, daiquiris and Daiquiri deck and Oysters at the Siesta Key Oyster bar. The house itself was clean and very well appointed with beach chairs, wagons, umbrellas etc.
Stayed 4 nights in Jan 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Patty S.

Great Stay in the Penthouse!

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!
Stayed 5 nights in Apr 2024

10/10 Excellent

Katy C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location & Layout for 2 families!

This property was perfect for 2 families with teenagers on Spring Break. The layout of the penthouse was perfect and accommodated all of us comfortably. Bonus laundry just off the master bathroom was a welcome surprise. Plenty of beach chairs, wagons & bikes for all of us plus others staying in the other units. There is a trolley stop right in front of the property. It is literally 3 minute walk onto the beach and 10 minute stroll into town. Dan was responsive. Highly recommend booking here.
Stayed 5 nights in Mar 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Diana D.

A little piece of paradise.

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The location was fantastic and stocked with beach lawn chairs, paddle boards, bicycles, and wagons. Other fun activities included ping pong and corn hole. It was also nice to have a grill available. Daniel sent thorough communication and was very kind when I spoke to him. Our vacation here was delightful!I would recommend having sand toys for little ones.
Stayed 4 nights in Dec 2022

10/10 Excellent

Dana W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls Weekend 2023

We had a wonderful stay! The beach was right across the street, the trolley stop was right outside or it was a short walk to town. The living space, bathrooms and bedrooms were very comfortable. We loved watching the storms and the ocean from the accordion doors in the living room. The light switches and fans were a bit difficult to use in the beginning but worked well after we learned. We didn’t understand where to park parallel to the building but the maintenance man was nice to show us. You must take 2 flights of stairs to get to the unit. Exhausting but well worth it!
Stayed 3 nights in Sep 2023

8/10 Good

Verified traveller

Liked: Check-in, communication, location, listing accuracy

First trip to Siesta Key

I am giving this location a 4 out of 5. The unit itself is nice. Nice flooring, nice master bath, nice counter tops. Most of the family said the beds were comfortable. Plenty of towels. Plates & utensils were all clean. 2 locations outside the unit to rinse off sand. Lots of chairs, umbrellas, & wagons to use at the beach. Beach access is just across the street. I thought the unit was sufficiently clean but I am very very particular. Here was why I didn’t give it a 5 - & quite honestly I’m shocked it got so many 5/5 reviews - the entrance to the unit is really bad. The 2 flights of stairs leading up to the unit has old gross carpeting. I felt like this made the actual unit feel dirty. Separately, i do not think the listing states that there are multiple units that share some common spaces. This wasn’t a problem for us but it should be mentioned. Everyone who was staying in the building seemed respectful of the fact that others were there & noise was never a problem… & everyone put all beach items away neatly after using. Beach access is steps away from the main door, The Village is a 10 min walk & the trolley stop is also right outside the door. All in all it’s a good spot. The unit is a little small for the number of people that it sleeps. I think a cpl updates & the place will be spectacular! Oh & I thought the host was fabulous with communication. My 2 biggest complaints - the stairs & the unit needs a vacuum to help keep floors cleaned up. Otherwise, I’d give it a 5!
Stayed 6 nights in Jul 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Brad C.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Michael J.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Min S.

Beach life

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.

8/10 Good

Keri W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Holiday Rental

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
Stayed 4 nights in Dec 2024

10/10 Excellent

Charles M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Christmas getaway!

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.
Stayed 3 nights in Dec 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Luis C.

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

10/10 Excellent

Skye H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

So much fun on Siesta Key!

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!
Stayed 3 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Scott H.

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.

About the host

Hosted by Gertrude Rentals 888-5SIESTA

Host profile image
Dan Jones, "owner" Gertrude Rentals
Phone: (888) 5-SIESTA
Email: gertrude.rentals@gmail.com
Website: gertruderentals.com

Languages:

English, French

Premier Host

They consistently provide great experiences for their guests