NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach

Siesta Key, Florida
$583 avg/night
Bed 3

Bed

Bath 2

Bath

Home Condo

Property Type

Sleep 10

Max Sleeps

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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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1500 Sq Ft (139 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi, With Speed Of 250+ Mbps (good For 3–5 People Or Up To 10 Devices)
  • OUTDOORS

    Balcony Barbecue Grill
  • POOL/SPA

    Heated Pool Shared/communal Pool
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • LANGS SPOKEN

    English French
  • THINGS TO DO

    Fitness Facilities Nearby Jet Skiing Nearby Kayaking Nearby Parasailing Nearby Power Boating Nearby Scuba Diving Nearby Snorkeling Nearby Surfing/body Boarding Nearby Theme Parks Nearby Water Park Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    Near A Hospital Near A Zoo Near Outlet Shopping Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Elevator If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Wheelchair Accessible

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Steve c.

    Submitted Feb 6, 2026

    Stayed Jan 29, 2026

    Beautiful house, beautifully finished. Everything we could need for the weekend! Thank you so much for making it easy for us.

  • Adam H.

    Submitted Nov 13, 2025

    Stayed Nov 5, 2025

    Our group reserved both the upper and lower floors and had a wonderful stay. Quick walk to the beach and in a quiet location.

  • Jennifer L.

    Submitted Oct 20, 2025

    Stayed Oct 15, 2025

    Enjoyed the stay with my husband - just the relaxing getaway we needed!

  • Nova H.

    Submitted Sep 30, 2025

    Stayed Sep 25, 2025

    Beautiful home and wonderful family to work with! Highly recommend this gorgeous condo!!

  • Nova H.

    Submitted Sep 30, 2025

    Stayed Sep 25, 2025

    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.

    Submitted Sep 30, 2025

    Stayed Sep 25, 2025

    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!

  • Nova H.

    Submitted Sep 30, 2025

    Stayed Sep 25, 2025

    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.

  • Alyssa S.

    Submitted May 3, 2025

    Stayed Apr 21, 2025

    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!

  • Lexi S.

    Submitted Dec 3, 2024

    Stayed Nov 28, 2024

    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!

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Total

Includes taxes and fees
$583+
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