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, 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.
Este condominio se encuentra cerca de parques temáticos, a orillas del agua, en Siesta Key. Aquellos que deseen ir de compras pueden visitar St. Armands Circle y Centro comercial The Mall at University Town Center, mientras que quienes quieran apreciar la belleza natural del área pueden ir a Playa pública Siesta Key y Playa Crescent. Puedes salir una noche a Sarasota Fairgrounds & Robarts Arena o, si viajas con niños, puedes ir a Mote Science Education Aquarium. Las actividades como paseos en moto de agua y kayak ofrecen una gran oportunidad de disfrutar del agua y, si buscas un poco de adrenalina, puedes hacer ecotours y ciclismo en los alrededores.
¿Cuánto cuesta el estacionamiento en Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
Hay estacionamiento disponible en la propiedad.
¿A qué hora es el check-in en Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
Hora de inicio de check-in: 15:00.
¿A qué hora es el check-out en Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
Check-out: 10:00.
¿Dónde se encuentra Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?
Este condominio para familias de Siesta Key se encuentra a orillas del agua, a 10 minutos a pie de Gulf Intracoastal Waterway y Playa pública Siesta Key. Playa Crescent y Laberinto de la iglesia episcopal de St. Boniface también se encuentran a 2 km.
Opiniones
Opiniones de Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!
8,0
Muy bueno
Todas las opiniones que se muestran provienen de experiencias de huéspedes reales. Solo las personas que han reservado una estadía con nosotros pueden enviar su opinión. Verificamos las opiniones con base en nuestras pautas y las publicamos todas, tanto positivas como negativas.Más informaciónSe abre en una nueva ventana
10
Limpieza
8,0
Ubicación
Evaluación: 10 - Excelente. 1 de 3 opiniones
10 - Excelente
1
Evaluación: 8 - Bueno. 1 de 3 opiniones
8 - Bueno
1
Evaluación: 6 - Aceptable. 1 de 3 opiniones
6 - Aceptable
1
Evaluación: 4 - Mediocre. 0 de 3 opiniones
4 - Mediocre
0
Evaluación: 2 - Terrible. 0 de 3 opiniones
2 - Terrible
0
Opiniones
Opinión verificada
10/10 Excelente
Joy E.
13 mar. 2026
Le gustó: Limpieza, check-in, comunicación, ubicación, veracidad del anuncio
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!
Se hospedó 5 noches en marzo de 2026
Opinión verificada
6/10 Aceptable
Andrea C.
7 ago. 2026
Le gustó: Limpieza, check-in, ubicación
No le gustó: Veracidad del anuncio
We were unaware until after we booked that we were in. 2 separate condos instead of a 4 bedroom 2 bath condo. Felt like bait and switch.
Se hospedó 4 noches en julio de 2026
Opinión verificada
8/10 Buena
Kara B.
10 jun. 2026
Le gustó: Limpieza, check-in, comunicación, veracidad del anuncio
We rented both units, but did not realize upon renting that they are actually located 4 units apart. Not a big deal but figured it is good for groups to know. The property was nice, but you really need a golf cart to go back and forth to the beach. It is a farther walk especially if you have elderly folks with you. The pool and pickleball courts were nice, but the rules state you are only allowed for "one hour" per unit on the courts. The management was responsive, and overall we enjoyed our stay.