Title: Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=113531136&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire condo # Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! ## Photo gallery for Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! ![Beach nearby - Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! (Siesta Key)](https://images.trvl-media.com/lodging/114000000/113540000/113531200/113531136/f8c59c89.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Marina - Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! (Siesta Key)](https://images.trvl-media.com/lodging/114000000/113540000/113531200/113531136/6f90ab6f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, offices - Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! (Siesta Key)](https://images.trvl-media.com/lodging/114000000/113540000/113531200/113531136/7daff38b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! (Siesta Key)](https://images.trvl-media.com/lodging/114000000/113540000/113531200/113531136/ebe75d7b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining - Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! (Siesta Key)](https://images.trvl-media.com/lodging/114000000/113540000/113531200/113531136/8f43bd55.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Crescent Beach and Siesta Key Beach are located near Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!, which provides golfing on site, a garden, and laundry facilities. Active travelers can enjoy kayaking at this condo. For some rest and relaxation, visit the hot tub. Free in-room WiFi, with speed of 100+ Mbps (good for 1–2 people or up to 6 devices), and a gym are available to all guests. ### Entire condo 4 bedrooms4 bathrooms2100 sq ft ## Popular amenities - Ocean view - Pool - Hot tub - Kitchen - Washer - Dryer ## 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. ### Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! Bayside Units Two top floor bayside units (4BR total) with 40-foot balcony, tennis/pickleball courts, elevator, private beach and complimentary beach chaises, two heated pools, bay-front lounging area, hot tub, causeway on inter-coastal, boat moors, fitness center, fishing pier, and beautifully manicured grounds stretching from Beach to Bay. Enjoy resort amenities in the heart of Siesta Key. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta What Guests Love ∙ Resort Amenities – heated pools, jacuzzi, gym, pickle, tennis, and boat moors ∙ The Balcony – royal palm views from balcony connecting bedrooms and living area ∙ Two Units – separate units means you can be together but still have your own space ∙ The Grounds – fishing causeway, private bay and beach access, lined by royal palms ∙ Private Beach – 4-min walk to private beach and Siesta Key's widest whitest sands ∙ Restaurants – 2-min walk to free trolley to all Siesta's shopping dining and entertainment ∙ Sunsets –walk 4-min to best sunsets in America or just enjoy from your balcony ∙ Activities – scooter, golf cart, bike and kayak rentals nearby ∙ 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 – perfect fit for all with resort amenities and trolley to all top attractions The Beach Our beach is a private Siesta Key beach with the widest whitest sands, free chaise lounges, and umbrella rentals. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. The Location With so many amenities, and all of it free of charge, a 3-night stay here will feel like a two-week getaway. If you get the most from a vacation when you don't have search or worry about anything, this unit is not a plus for you it's a must! Although you could easily take a free trolley 1-mile any direction to dozens of shops and restaurants, you can also satisfy every vacation desire without ever putting on your shoes or leaving this resort. You can swim in pools or in the Gulf, fish the inter-coastal, exercise in the gym, sleep in the sun, explore Siesta Key's best beach, make Sandcastles, and even sightsee all in a safe environment and right on your property. The beach here has the whitest sand on the island, but some of the best moments are watching boats and dolphins pass from the private balcony or nearby bay-front pool. Bedroom Details This is two 3rd-floor 2BR units (4BR total, sleeps 12) with an elevator. One 2BR unit has a king bedroom, a bedroom with two queens, and a sofa in the living room. The next 2BR unit has a king bedroom, a queen bedroom and a sofa in the living room. If you need more space, I can get an additional unit nearby. Beach Gear Provided We provide beach towels, and the resort provides free chaise loungers and umbrella rentals. If you have any issues just reach out and we will do whatever we can. 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. Important Resort Limits 1) Expect a special experience where each visitor's peaceful enjoyment is respected. The minimum age for visitors not accompanied by a parent or guardian is 25 years. Stay up as late as you want, but the “quiet neighbor times” begin 10 PM. After 10 PM relocate the party to nearby Siesta Village or the Crescent Beach area. 2) Just one parking space per unit (two total this listing). However, cars are not necessary and an additional "emergency parking space" is available 1 mile away. If any of these limits are not a fit for you, please let me know, I have other properties available. Household Items Provided We provide bedding, kitchen items, private laundry, 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 - Hot tub ### 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 - 4 bedrooms - Bedsheets provided ### Bathroom - 4 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 - Garden ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Office ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Elevator - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - In a village - Near a hospital - Near a zoo - Near the bay - Near the marina - Near the ocean - On the waterfront ### Things to do - Golf - Gym - Heated pool - Kayak - Tennis - 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 - Garden - Property located in a resort - Unit size: 2,100 square feet ## Similar properties ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/115000000/114940000/114930700/114930646/214af074.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 'the City Oasis' Near IMG & Anna Maria Island! 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The Village Breeze – 4BR/2BA, Pool, Walk to Beach & Siesta Key Village (2 Units) Siesta Key Village - Pool - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26&selected=119492634&PinnedHotelID=119492634&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88430000/88429000/88428954/76853f63.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 4 Bedroom Pool Home Siesta Key Siesta Key - Pool - Kitchen - Washer - Dryer 10 Exceptional 22 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26&selected=88428954&PinnedHotelID=88428954&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/117000000/116780000/116774000/116773993/69964ce2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### NEW LISTING! The Village Breeze (2 units) 4BR/4Bath Pool, Beach - Siesta Village Living! 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Private Dock and Beach Views! - Sea Spray Siesta Key - Hot tub - Kitchen - Washer - Dryer 9.6 Exceptional 77 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26&selected=22209956&PinnedHotelID=22209956&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/32000000/31740000/31732200/31732197/f1b4bbb9.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Lovely Pet Friendly Condo a Block from Siesta Key Village, Two Pools & Tiki Bar Siesta Key Village - Kitchen - Washer - Dryer - Pet friendly 9.8 Exceptional 17 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26&selected=31732197&PinnedHotelID=31732197&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26&selected=113531136&PinnedHotelID=113531136&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=113531136,114930646,119923818,78505267,31948461) ## Policies ### Check-in Check-in time starts at 3:00 PM Minimum check-in age: 25 ### Check-out Check-out before 10:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions Information provided by the property may be translated using automated translation tools ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Events No events allowed ### 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 Onsite parties or group events are strictly prohibited Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher and a deadbolt lock 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 ### Property is also known as 889412 ## About the area Located in Siesta Key, this condo is near theme parks and on the waterfront. 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. Looking to enjoy an event or a game while in town? See what's happening at Ed Smith Stadium or Sarasota Kennel Club. 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%7C27.26302%2C-82.54023&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=DRldlD5NilxXgad3RzKe-JLvdQY=) 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 6 min walk \- 0.6 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 \- 1.8 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) 31 min drive ### Restaurants - Siesta Beach Pavilion 18 min walk - McDonald's 3 min drive - Siesta Key Snack Bar 18 min walk - Captain Curt's Crab & Oyster Bar 18 min walk - Dunkin' 4 min drive ## Frequently asked questions ### Does Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! have a pool? ### Is Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! pet-friendly? ### How much is parking? ### What time is check-in at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!? ### What time is check-out at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!? ### Where is Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! 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