Title: NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire condo # NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach Condo with a water park, steps from Siesta Key Beach ## Photo gallery for NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach ![Beach nearby - NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach (Siesta Key)](https://images.trvl-media.com/lodging/121000000/120550000/120540300/120540250/d0a120b0.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Smart TV - NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach (Siesta Key)](https://images.trvl-media.com/lodging/121000000/120550000/120540300/120540250/e6f11c78.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach (Siesta Key)](https://images.trvl-media.com/lodging/121000000/120550000/120540300/120540250/c394e5e7.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV - NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach (Siesta Key)](https://images.trvl-media.com/lodging/121000000/120550000/120540300/120540250/cfecd57f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining - NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach (Siesta Key)](https://images.trvl-media.com/lodging/121000000/120550000/120540300/120540250/3eab03d2.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Close to Siesta Key Beach and Crescent Beach, NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach provides amenities like a water park. Guests can connect to free in-room WiFi. ## Reviews 9.8 Exceptional ### Entire condo 3 bedrooms2 bathrooms1500 sq ft ## Popular amenities - Pool - Kitchen - Washer - Dryer - Pet friendly - Free WiFi ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire condo to yourself and will only share it with other guests in your party. ### NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach 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. ## Property amenities ### Beach - Beach nearby ### Pool/Spa - Communal pool - Heated pool ### Internet - Available in the condo: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Kitchen island - Microwave - Oven - Refrigerator - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 3 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Bathtub or shower - Hair dryer - Shower - Towels provided ### Living spaces - Dining table - Living room - Separate dining area ### Entertainment - Smart TV with cable/satellite channels ### Outdoor areas - Balcony - Barbecue grill ### Laundry - Washing machine ### Comfort - Air conditioning - Heating ### Pets - Pet friendly ### Suitability/Accessibility - If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking. - Elevator - Wheelchair accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - Near a hospital - Near a zoo - Near an outlet shopping mall - Near the bay - Near the marina - Near the sea ### Things to do - Heated pool - Water park - Birdwatching nearby - Cycling nearby - Ecotours nearby - Fishing nearby - Golfing nearby - Jet skiing nearby - Kayaking nearby - Motor boating nearby - Parasailing nearby - Sailing nearby - Scuba diving nearby - Snorkeling nearby - Surfing/bodyboarding nearby - Swimming nearby - Theme park nearby - Wildlife walks nearby - Windsurfing nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - Fire extinguisher - Deadbolt lock ### General - Unit size: 1,500 square feet ## Similar properties ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119700000/119696500/119696475/d82b4a31.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village Siesta Key Village - Pool - Hot tub - Kitchen - Washer 10 Exceptional 16 reviews CA $948 CA $1,766 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-01&endDate=2026-03-02&selected=119696475&PinnedHotelID=119696475&HadPinnedHotel=true®ionId=-1&adults=2) ![Pool](https://images.trvl-media.com/lodging/115000000/114930000/114927800/114927725/0db989f0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Treasure Island 2BR Condo w W/D & Pool Access Sunshine Beach - Ocean view - Pool - Kitchen - Washer CA $552 CA $918 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-18&endDate=2026-02-19&selected=114927725&PinnedHotelID=114927725&HadPinnedHotel=true®ionId=-1&adults=2) ![Marina](https://images.trvl-media.com/lodging/58000000/57950000/57945400/57945371/dea52002.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 🏖️ Madeira Bay Resort I #1708 – Clean, Comfortable & Steps from the Sand Madeira Beach - Pool - Hot tub - Kitchen - Washer 9.0 Wonderful 19 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-12&endDate=2026-02-13&selected=57945371&PinnedHotelID=57945371&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/117000000/116470000/116465900/116465884/abf22ecf.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### NEW LISTING! 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You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as 995794 ## About the area Located in Siesta Key, this condo is near theme parks 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. Mote Marine Laboratory & Aquarium and Coconuts Family Entertainment Center are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching. [Visit our Siesta Key travel guide](https://www.expedia.ca/Siesta-Key.dx6881) [View more Condo rentals in Siesta Key](https://www.expedia.ca/Siesta-Key-Condos.d6881-aaCondos.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C27.26197%2C-82.54243&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=5gIKcnDvJw8aLRvWwVQc2apu2r0=) Siesta Key, FL ### What's nearby - ![Southwest Florida featuring general coastal views and a beach as well as a large group of people](https://images.trvl-media.com/place/6066003/ad6a01c6-1eea-49fa-a977-77719bf71f3d.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Siesta Key Beach 1 min walk \- 0.2 km - ![SiestaKey_StBonifaceEpiscopalChurchLabyrinth_6295832-2](https://images.trvl-media.com/place/6295832/0234e27f-680b-4700-9ba6-49f2b268f067.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) St. Boniface Episcopal Church Labyrinth 14 min walk \- 1.2 km - ![SiestaKey_SiestaKeyMarina_6295966-4](https://images.trvl-media.com/place/6295966/f3cc8ba3-b51d-4cff-b4c4-894d1c04236e.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Siesta Key Marina 2 min drive \- 1.7 km - ![USA, Florida, Crescent Beach, Siesta Key, Sarasota, Seascape, Orange Sunset](https://images.trvl-media.com/place/553248621532652551/4a53536a-a503-47c2-8adc-e2d5c2b47074.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Crescent Beach 2 min drive \- 2.1 km - Siesta Key Beach Playground 15 min walk \- 1.3 km ### Getting around - Sarasota-Bradenton Intl. Airport (SRQ) 33 min drive ### Restaurants - Siesta Beach Pavilion 17 min walk - Siesta Key Snack Bar 18 min walk - Captain Curt's Crab & Oyster Bar 2 min drive - Dunkin' 4 min drive - Daiquiri Deck South Siesta Key 2 min drive ## Frequently asked questions ### Does NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach have a pool? ### Is NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach pet-friendly? ### How much is parking? ### What time is check-in at NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach? ### What time is check-out at NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach? ### Where is NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 7 8 - Good 1 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 9.4 Location ## Reviews ### 10/10 Excellent #### Alyssa S. May 3, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Exactly as described 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! ##### Alyssa S. Stayed 7 nights in Apr 2025 ### 10/10 Excellent #### Lexi S. Dec 3, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 10/10 stay at Scott's place in Siesta Key!!! 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! ##### Lexi S. Stayed 4 nights in Nov 2024 ### 8/10 Good #### Jennifer L. Oct 20, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Enjoyed the stay with my husband - just the relaxing getaway we needed! ##### Jennifer L. Stayed 5 nights in Oct 2025 This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Nova H. Sep 30, 2025 #### Perfect place for my group. 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. This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Nova H. Sep 30, 2025 #### Beautiful home and wonderful family to work with! Highly recommend this gorgeous condo!! Beautiful home and wonderful family to work with! Highly recommend this gorgeous condo!! ##### Nova H. This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Nova H. Sep 30, 2025 #### Was a fabulous stay! 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. This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Nova H. Sep 30, 2025 #### Best condo I've ever been to. 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. ##### Nova H. ## Expedia's Latest Trends ### Hotels > [Hammock Beach Golf Resort & Spa](https://www.expedia.ca/Daytona-Beach-Hotels-Hammock-Beach-Golf-Resort-Spa.h994170.Hotel-Information) > > [Holiday Inn Resort Panama City Beach by IHG](https://www.expedia.ca/Panama-City-Hotels-Holiday-Inn-Resort-Panama-City-Beach.h18867.Hotel-Information) > > [Capt Hiram's Resort](https://www.expedia.ca/Vero-Beach-Hotels-Capt-Hirams-Resort.h7719643.Hotel-Information) > > [The Resort at Longboat Key Club](https://www.expedia.ca/Sarasota-Hotels-The-Resort-At-Longboat-Key-Club.h27542.Hotel-Information) > > [Windsor Island Luxury | Home in Windsor Island Resort, Private Pool, Arcade](https://www.expedia.ca/Davenport-Hotels-Windsor-Island-Luxury-Home-In-Windsor-Island-Resort.h60809096.Hotel-Information) > > [The Shores Resort & Spa](https://www.expedia.ca/Daytona-Beach-Hotels-The-Shores-Resort-Spa.h15752.Hotel-Information) > > [PGA National Resort ](https://www.expedia.ca/Palm-Beach-Gardens-Hotels-PGA-National-Resort-And-Spa.h10355.Hotel-Information) > > [DiamondHead Beach Resort](https://www.expedia.ca/Fort-Myers-Hotels-DiamondHead-Beach-Resort.h200632.Hotel-Information) > > [Bahama House](https://www.expedia.ca/Daytona-Beach-Hotels-Bahama-House.h893658.Hotel-Information) > > [White Elephant Palm Beach](https://www.expedia.ca/Palm-Beach-West-Palm-Beach-Hotels-White-Elephant-Palm-Beach.h42412055.Hotel-Information) > > [Hotel Effie Sandestin, Autograph Collection](https://www.expedia.ca/Fort-Walton-Beach-Destin-Hotels-Hotel-Effie-Sandestin-LIF.h39215603.Hotel-Information) > > [Pink Shell Beach Resort and Marina](https://www.expedia.ca/Fort-Myers-Hotels-Pink-Shell-Beach-Resort-And-Marina.h15603.Hotel-Information) > > [Holiday Inn Express Hotel & Suites Fort Pierce West by IHG](https://www.expedia.ca/Vero-Beach-Hotels-Holiday-Inn-Express-Hotel-Suites-Fort-Pierce-West.h538557.Hotel-Information) > > [Zota Beach Resort](https://www.expedia.ca/Sarasota-Hotels-Zota-Beach-Resort.h15703469.Hotel-Information) > > [Compass Hotel by Margaritaville Anna Maria Sound](https://www.expedia.ca/Sarasota-Hotels-Compass-Hotel-By-Margaritaville.h41961327.Hotel-Information) > > [South Seas Resort](https://www.expedia.ca/Fort-Myers-Hotels-South-Seas-Island-Resort.h40732.Hotel-Information) > > [Margaritaville Beach House Key West](https://www.expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) > > [The Resort on Cocoa Beach](https://www.expedia.ca/Cocoa-Beach-Hotels-The-Resort-On-Cocoa-Beach.h329971.Hotel-Information) > > [Mission Resort and Club](https://www.expedia.ca/Leesburg-Hotels-Mission-Inn-Resort-Club.h2057662.Hotel-Information) > > [Cedar Cove Resort and Cottages](https://www.expedia.ca/Sarasota-Hotels-Cedar-Cove-Resort-And-Cottages.h8099611.Hotel-Information) > > [The Ben West Palm, Autograph Collection](https://www.expedia.ca/West-Palm-Beach-Hotels-The-Ben-West-Palm.h38983694.Hotel-Information) > > [Casa Del Mar Longboat Key](https://www.expedia.ca/Sarasota-Hotels-Casa-Del-Mar-Longboat-Key.h15602940.Hotel-Information) > > [Tropic Sun Towers](https://www.expedia.ca/Daytona-Beach-Hotels-Tropic-Sun-Towers-By-Capital-Vacations.h1169627.Hotel-Information) > > [Hyatt Regency Coconut Point Resort & Spa](https://www.expedia.ca/Naples-Hotels-Hyatt-Regency-Coconut-Point-Resort-Spa.h792025.Hotel-Information) > > [Hilton Grand Vacations Club in Sandestin Golf & Beach Resort](https://www.expedia.ca/Miramar-Beach-Hotels-Embarc-Sandestin.h1054729.Hotel-Information) > > [Edgewater Beach & Golf Resort by Resort Collection](https://www.expedia.ca/Panama-City-Hotels-Edgewater-Beach-And-Golf-Resort-By-Resort-Collection.h803238.Hotel-Information) > > [Amrit Ocean Resort and Residences - Singer Island](https://www.expedia.ca/Palm-Beach-West-Palm-Beach-Hotels-Amrit-Ocean-Wellness-Resort.h36247449.Hotel-Information) > > [Hilton Vacation Club Daytona Beach Regency](https://www.expedia.ca/Daytona-Beach-Hotels-Hilton-Vacation-Club-Daytona-Beach-Regency.h40772.Hotel-Information) > > [Hilton Garden Inn Cocoa Beach Oceanfront](https://www.expedia.ca/Cocoa-Beach-Hotels-DoubleTree-By-Hilton-Cocoa-Beach-Oceanfront.h4398.Hotel-Information)