The Bayside Unit Top floor bayside unit 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 ∙ 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 a 3rd-floor (top) unit with an elevator. This two-bedroom unit has a king bedroom, a bedroom with two fulls, and a 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 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.
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.
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
About the area
Siesta Key
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. Travelling with kids? Consider Mote Marine Laboratory & Aquarium, or check out an event or a game at Ed Smith Stadium. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours.
Siesta Key, FL
What's nearby
Siesta Key Beach - 6 min walk - 0.6 km
St. Boniface Episcopal Church Labyrinth - 14 min walk - 1.2 km
Siesta Key Beach Playground - 15 min walk - 1.3 km
Siesta Key Marina - 2 min drive - 1.8 km
Crescent Beach - 2 min drive - 2.1 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 31 min drive
Restaurants
Siesta Beach Pavilion - 18 min walk
Siesta Key Snack Bar - 18 min walk
McDonald's - 3 min drive
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?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
As of 22 April 2026, prices found for a 1-night stay for 2 adults at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! on 11 July 2026 start from NZ$617, 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 | Bayside 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 | Bayside 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 | Bayside 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 | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
Checkout is at 10:00 AM.
Where is Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! located?
This family-friendly Siesta Key condo building is located on the waterfront, within 1 mi (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.
Great location & very clean! The beds were comfortable!
Karen C.
Stayed 3 nights in Nov 2025
Response from VrboOwner on 5 December 2025
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
Beautiful condo. Very clean. Daniel, the host, was very responsive and helpful. We had a great time!!
Verified traveller
Stayed 4 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
We enjoyed our stay very much in this unit. It was clean, comfortable, and well equipped, and communication with the owner (Daniel) was excellent. We visited during the last week of January, when ocean swimming is often too cold, so being close to the swimming pool and hot tub was important to us. This unit was conveniently located near both and was also just a short walk to the ocean.The Palm Bay Club has a wonderful private beach, along with tennis and pickleball courts, and complimentary beach chair rentals. Overall, this is a very nice unit and a great place to stay.
Hiroko D.
Stayed 6 nights in Jan 2026
Response from VrboOwner on 15 February 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
The host was communicative and available for any questions and even reached out to make sure everything was up to snuff. The property is a pretty tranquil setting with perfect location with a serene pool. The unit itself is well appointed and plenty of room.
Tracy B.
Stayed 3 nights in Nov 2025
Response from VrboOwner on 5 December 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Nova H.
24 November 2024
Great
We really enjoyed our stay! Will definitely stay here again!
Nova H.
From a partner site
10/10 Excellent
Nicholas B.
3 August 2025
Great
Fantastic rental! Wonderful location!! We'd definitely stay again! Only suggestion is add some hot pads in kitchen (and we didn't ask for them so it's possible we just couldn't find them….) Loved our stay!!!
We enjoyed our stay and exploring the area. Weather was fantastic.
Mary S.
Stayed 4 nights in Mar 2025
Response from VrboOwner on 22 April 2025
Thank you for staying with us! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
julie c.
1 December 2024
Great
Lovely comfortable stay close to the beach about a 5-7 minute walk.
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
Excellent location. Comfortable and well appointed unit. Gorgeous beach. Nice pools and tennis courts and other amenities. Great communication with owner. Very enjoyable for our family.
Steve M.
Stayed 3 nights in Dec 2024
Response from VrboOwner on 12 January 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
Very nice condo. We were close to the intercoastal end of the property, where a pool and hot tub overlook the water. An easy walk over to the beach, with private access. Such a nice property!
Todd T.
Stayed 4 nights in Feb 2025
Response from VrboOwner on 16 February 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Nova H.
22 November 2024
Perfect Getaway
We were very pleased with condo and the property. The place was clean and everything is new. It's a 2 minute walk to the bayside pool and hot tub or a 5 minute walk to the beach! We will definitely stay here again.
Nova H.
From a partner site
10/10 Excellent
barbara d.
12 April 2025
Great time!
We had a wonderful time in Siesta Key at Palm Bay Club that we rented through Gertrude rentals. The process of renting was easy and responses were quick! Thank you Gertrude rentals!
barbara d.
From a partner site
10/10 Excellent
Kelly R.
30 May 2025
Very clean, great location
My family felt very safe and comfortable in this condo. The kitchen was fully supplied making it easy to prepare meals. The condo was very clean. I loved the location with a short walk to the beach. I found the staff at the Palm Bay Club to be very nice. Gertrude's rentals were very quick to respond and helpful.
Location was perfect. Pools, beach & amenities were great. Condo was clean and filled with most everything we needed. Need more hooks throughout, to hang towels and bathing suits and an ottoman in the living room.
Kim T.
Stayed 6 nights in Mar 2025
Response from VrboOwner on 25 October 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
It was the worst place I have ever stayed since I visited my son's dorm in college. The bed was so soft we, we sank to the floor vanities were all broken from 1965. Formica cracked, exposed wires in utility room. Drawer in the kitchen that would only fully open if you open the oven all the way I'm 68 years old, and I've sted in many different places. This by far was the worst ever. We called management the very moment we arrived. We called VRBO, we offered to leave for a 50% refund. living in what looked like a frat house dorm room. to add insult to injury, the site invites you to add photos, but it does not work. I will continue to try to upload photos
Tina A.
Stayed 13 nights in Feb 2026
From a partner site
10/10 Excellent
Nova H.
22 November 2024
Beautiful property!
Beautiful property! Clean and safe! Only a 2 minute walk to the pool and hot tub that overlooks the bay. A beautiful 5 minute walk down a paved path lined with royal palms to the beach. The condo is so clean and the furniture is brand new! Great get away for our couples trip!
Nova H.
From a partner site
10/10 Excellent
Nova H.
21 November 2024
Favorite Siesta resort so far!
Stayed two places this week. Both were great, but this one was the best. Everything in the unit was brand new, the resort is gorgeous, and I loved the Bayside pool! Really didn't really need to leave the resort except for groceries and there was a free trolley right out front. Definitely five stars!
Everything was great. Zero problems and professional.
Jason D.
Stayed 3 nights in Nov 2024
Response from VrboOwner on 16 December 2024
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
jill h.
11 January 2025
Perfect family getaway
This place was a gem! The location was perfect! Simple, 5 minute walk to the beautiful beach and located steps away from the bay, with hot tub and pool. Our unit was clean, kitchen was well furnished and the beds were comfortable. The shuttles out front provided a quick and easy way to get to the Village (great restaurants, shops and bars). Owners were very responsive and professional. Thank you! We will be back!
jill h.
From a partner site
10/10 Excellent
Adam W.
16 January 2025
Great
This was the second time staying in one of Gertrude's properties and as before my experience was great. Everything was clean and presentable. Pool was heated to a very comfortable temperature. Felt secure in the gated complex. Communication was phenomenal and always accommodating for whatever your needs maybe. Always our go to host from when we come to Siesta Key.
Adam W.
From a partner site
10/10 Excellent
Hannan Abdel-Jalil H.
7 July 2025
Great Stay
This condo was perfect for me and my family. Just the right size with comfortable beds. I'm a very picky person and was extremely happy to find that the house was incredibly clean, very organized and decorated adorably. The unit provided us with all of the necessities needed during our stay, so we didn't have to eat out every morning or lunch. Publix grocery was close by and allowed us to stock up on some food. The unit was in a great location that took minutes to walk to the beach and the bay. The owner of the unit was very responsive and answered any questions we may had. Our only issue we had was connecting to the WiFi. It was working, just couldn't find the network on a few of our phones, however we all had great phone connections, so it wasn't even an issue at all. If our family decides to revisit Siesta Keys, we will definitely return to this condo. Great memories made.
Hannan Abdel-Jalil H.
From a partner site
10/10 Excellent
Nicki M.
25 February 2026
⭐️⭐️⭐️⭐️⭐️
We had a wonderful stay at Palm Bay bayside. Our unit was beautifully decorated, clean and had everything we could possibly need. Security was outstanding.Short walk to the pool which also had a bathroom.We saw dolphins, pelicans and many boats. We also walked to the beautiful beach. Transportation was so easy. Can't wait to go back.
Thank you for staying with us! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones