The Bayside Unit Second floor bayside Siesta Key vacation rental 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!
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 ∙ The Grounds – fishing causeway, private bay and Siesta Key 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 ∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest cost
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 a 2nd-floor unit with an elevator. This two-bedroom unit has a king bedroom, a queen bedroom with additional full sized trundle, and a sleep sofa in the living room. You can sleep up to 6. 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. 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 This vacation rental comes with 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 Siesta Key is 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.
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 cannotpurchased 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.
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.
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Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
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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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Frequently asked questions
Does Gertrude's Siesta | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Gertrude's Siesta | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
As of 7 April 2026, prices found for a 1-night stay for 2 adults at Gertrude's Siesta | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! on 31 May 2026 start from NZ$681, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Gertrude's Siesta | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Gertrude's Siesta | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
On-site parking is available at the property.
What time is check-in at Gertrude's Siesta | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
Check-in begins at 3:00 PM.
What time is check-out at Gertrude's Siesta | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
Checkout is at 10:00 AM.
Where is Gertrude's Siesta | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! located?
Situated on the waterfront, this condo building is within 1 mile (2 km) of St. Boniface Episcopal Church Labyrinth, Siesta Key Beach and Crescent Beach. Siesta Key Beach Playground and Siesta Key Marina are also within 1 mile (2 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The location was great! A short walk to beach. We enjoyed the heated pool and hottub over looking the bay. The condo was very clean and well furnished. We will book this place again for our next stay.
Clean! Everything was clean and very updated. Close to the beach. It was perfect for our family vacation.
Lindsay H.
Stayed 3 nights in Feb 2026
Response from VrboOwner on 16 March 2026
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Shannon T.
8 February 2026
Great Family Vacation
This is the perfect location for a relaxing family vacation. 2 pools with one overlooking the ocean and a Hot Tub where you can view all the boats passing by. Tennis/Pickle ball Courts, private beach area with provided beach chairs and a serene walk to the ocean with Palm Trees lining the brick road. We really enjoyed everything about the property, location and amenities.
Shannon T.
From a partner site
10/10 Excellent
Shannon T.
8 February 2026
Clean and great location
We could walk to the pool, hot tub, and beach all within a 5 minutes of our condo. The furniture seemed brand new and the condo was spotless. We will definitely visit this condo again in the future!
Helpful host! We enjoyed the property from the inlet to the ocean! Clean and comfortable. Loved the private beach area and chairs. It was nice to come back to the hot tub in the evening. Thanks for a great stay!
Diane H.
Stayed 4 nights in Dec 2025
Response from VrboOwner on 10 January 2026
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones
Everything was as listed. Small issue with wifi connection but quickly remedied by Daniel.
Michael L.
Stayed 2 nights in Mar 2026
From a partner site
8/10 Good
laurie g.
4 February 2026
Beautiful condo
Our condo was as expected - beautiful 2 bed 2 bath. A few things quirky. Shower pull and plug in bathroom sink did not work 100% but manageable. No strainer for noodles so used salad spinner. Would have been nice to have a few basic spices - just salt and pepper. Toilet paper extremely thin... these are little things. Overall a wonderful unit and no real issues. Enjoy!