A family-friendly stay in Siesta Key awaits you at this condo. Within a 20-minute stroll, you'll find popular places like Siesta Key Beach and Crescent Beach. .Condo features a washing machine, free WiFi and 4 bathrooms. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A balcony, a living room and a dining area are also available. .Enjoy the water park, gym and Hot tub. Added amenities include laundry facilities, a garden and barbecues.
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.
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
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
No pets 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
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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a deadbolt lock in all accommodation.
Property is also known as
889412
Frequently asked questions
Are there any beaches close to Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
Yep, Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! is a short 6-minute walk from Siesta Key Beach.
Fun beach activities include jet skiing, snorkelling and scuba diving. You can also find motor boats.
Does Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! have a pool?
Take your pick from a heated pool, a pool and a communal pool.
Does Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! have a waterslide?
No, but it has a waterpark and lazy river.
What makes Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! a romantic place to stay?
1 hot tub and private balconies help set the scene for a sizzling getaway at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!.
Is Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! family-friendly?
You bet! With amenities such as a water park and laundry facilities, as well as highchairs and travel cots, it's no surprise that Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! is a winner with our family travellers.
Is there a private hot tub at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
Yep, there is a hot tub.
Is there a free airport shuttle available at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
No, Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! does not offer an airport shuttle service.
What time are check-in & check-out at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
Check-in begins at 3:00 PM. Check-out time is 10:00 AM.
Are pets allowed at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
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.
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10/10
Cleanliness
Reviews
10/10 Excellent
Joy E.
13 Mar 2026
Liked: Cleanliness
Loved Siesta Key and can’t wait to go back. Daniel was an awesome host. He’s very helpful and responds to questions very quickly. We had an issue with our A/C unit and it was resolved quickly without any disruption to our day. Definitely recommend!