Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!
Gertrude's Village House Top location on the island with 3 patios and private gate into world famous Siesta Key Village! Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Enjoy private patios off the bedrooms and living area. Gertrude's is sure to provide a combination of fun ease and relaxation you can't get in other vacations so book a special getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta
What Guests Love ∙ Beaches – 1-min walk to award-winning beaches ∙ The Village – 10 steps to private gate into world famous Siesta Village ∙ Relaxing – three private patios off bedrooms and living area ∙ Sunsets – 1-min walk to best sunsets in America & 300-degree Gulf views ∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch ∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts ∙ Activities - kayak, bike, paddleboard, scooter, golf cart rentals nearby ∙ Island Trolleys - you're already where you want to be, but they're fun:) ∙ The Memories - one of a kind Siesta Key experience, favorite of initiated visitors
The Beach Our beach is the widest, has panoramic views of the gulf to the North-West-and-South, and is the top spot in North America for sunsets. You can swim or wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin sand-dollars and “occasionally” manatee and giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. You can go from the water to lunch or dinner and back to the sand without putting on your shoes.
The Home You work hard, you deserve this. Three patios are 100% private and surrounded by tropical plants with shade umbrellas, chaise loungers and dining tables. Perfect for enjoying a quiet cup of coffee, good book, cocktail(s), or an al-fresco meal. It's a few a steps off the patio to a private gate into the heart of the Village and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.
Bedroom Details This 3BR house is ground floor. Bedrooms include a king BR with French doors to a private patio, a queen suite with door to a private patio and bath, one bunk bed BR containing 2 twin over full beds, and a sofa in the living room. Need more space? We can get you a tempur-pedic rollaway bed or an additional unit nearby.
Beach Gear Provided We provide beach towels, chairs, carts, umbrellas, and usually have a few bikes and a paddleboard. If you don't have what you need, just reach out and we can usually get it for you. 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.
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.
History “Life is a string of pearls where you never know how many you have left.” - GVLJ. Gertrude Rentals was named for my grandmother “Gertrude” who traveled the world until age 91 but always insisted Siesta Key was the place she loved best. When I was young, she would take me to the beach and swim out so far, I couldn't see her yellow flowered bathing cap even while standing on a chair! Today, you can laze float and wade in the same white quartz sand and calm crystal-clear gulf water she once did.
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.
Our prices include all fees. No hidden fees.
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If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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 near the beach, this holiday home is in Siesta Key Village, a walkable area in Siesta Key with great shopping. 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 and St. Boniface Episcopal Church Labyrinth. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and mountain biking nearby.
St. Boniface Episcopal Church Labyrinth - 3 min drive - 2.4 km
Siesta Key Beach Playground - 3 min drive - 2.1 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 32 min drive
Restaurants
Siesta Beach Pavilion - 3 min drive
Circle K - 7 min walk
Siesta Key Snack Bar - 3 min drive
Gilligan's Island Bar & Grill - 3 min walk
Sun Garden Cafe - 6 min walk
Frequently asked questions
Is Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village! pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!?
As of 7 Jun 2026, prices found for a 1-night stay for 2 adults at Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village! on 8 Jun 2026 start from £386, 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.
How much is parking at Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!?
On-site parking is available at the property.
What time is check-in at Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!?
Check-in begins at 3:00 PM.
What time is check-out at Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!?
Checkout is at 10:00 AM.
Where is Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village! located?
This family-friendly Siesta Key holiday home is located by the sea, just steps away from Siesta Key Farmers Market and Siesta Key Beach. Crescent Beach is 2.9 mi (4.6 km) away.
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Such a cute beach house. You can’t beat the location ! We had such a great time and would book again
Kelly C.
Stayed 3 nights in Apr 2026
From a partner site
10/10 Excellent
Boxwood I.
28 Mar 2026
Village House
We loved our stay at the Village House!! You can not beat the location!! Out the back door you are in the village! Out the front door, look left, there's the beach!!! No need to rent a car. Everything was perfect for us! We will definitely stay here again!
Nice place, good location, property matched the description.
Todd W.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 1 Feb 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
Deanna
11 Feb 2026
⭐️⭐️⭐️⭐️⭐️
Absolutely recommend staying with Gertrude properties!!! Clean, close to everything. Planning our next stay and will only book with Gertrude properties♥️
Excellent location. 5 min walk to the beach in one direction, 5 min walk to the restaurants and shops in the other.2 assigned parking spots right in front of the unit. The home is older, but it is clean, has comfortable beds and location is top! Has chairs and bikes available as well. Although centrally located, and we stayed during peak season, it was surprisingly quiet. Host is very friendly, helpful and responsive. We had a great stay. I would recommend to a friend and family.
Greg D.
Stayed 2 nights in Mar 2026
From a partner site
8/10 Good
richard b.
17 Mar 2026
⭐️⭐️⭐️⭐️ Great location!
We came to siesta key with 5 kids. This house has the best location. Beach and all shopping/dining right next door. I was nervous the house would be noisy to restaurants/bars/foot traffic however that's not the case at all. It's one street over on a quiet street. It is very nice that beach buggy/chairs/bikes included. I gave 4 stars only because it's not a brand new house although everything was very clean. The layout is long, so the one bedroom has a further walk to the hallway bathroom than the others.
richard b.
Verified
10/10 Excellent
Jacquelene
7 Dec 2025
Liked: Amenities, communication
We enjoyed our stay,located behind restaurants shopping in Siesta Village and 5 minute walk to beach. The gate in the back yard entering restaurant parking on Ocean Blvd. was very convenient.
Thank you
Jacquelene
Stayed 2 nights in Dec 2025
From a partner site
10/10 Excellent
11 Oct 2025
Siesta Key Vollage
So close and convenient to shopping, dining choices and the beach!
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
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
Verified
10/10 Excellent
Bradley
16 May 2023
Liked: Cleanliness, amenities, property conditions & facilities, communication
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
The property is located in a great area convenient to the beach, restaurants, shopping and more.
Cliff L.
Stayed 5 nights in Jun 2023
Response from VrboOwner on 16 Jul 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Great property and a super great location! Short walk to Siesta Village and the beach. Property provides beach chairs, umbrellas and towels, as well as a cart to transport everything to the beach. Loved this property!
Robin B.
Stayed 3 nights in Jun 2025
Response from VrboOwner on 19 Jul 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
Great place in the heart of siesta key! Definitely recommend and would stay again.
Teresa K.
Stayed 3 nights in Apr 2023
Response from VrboOwner on 2 May 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
From a partner site
10/10 Excellent
Jeffrey C.
13 Feb 2025
Great Place to Stay
Awesome location, right downtown, very close to beach.
Very clean and comfortable and the cleaning crew was top notch!! Very friendly and even found a phone charger and made sure we didn't leave without it.
If you in Siesta Key can't go wrong here!
Close to restaurants, grocery store, bars and shops.
James F.
Stayed 7 nights in Dec 2022
Response from VrboOwner on 18 Dec 2022
Thank you James! We hope you visit again soon. You're a repeat guest now and can call me at (888) 5-SIESTA if you need anything at all! Always happy to help.
My family loved the house and perfect location! Easy walk to the beautiful beach and Siesta Village!
Amanda C.
Stayed 3 nights in Mar 2023
Response from VrboOwner on 14 Apr 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you.
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
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
We had a great stay at Gertrude’s. Nice-sized bedrooms and just enough common space to set up a tree and celebrate Christmas morning. Our 28-63 year old group enjoyed the close proximity of restaurants and shopping.
Janelle W.
Stayed 8 nights in Dec 2024
Response from VrboOwner on 12 Jan 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
Debra B.
5 Apr 2024
Siesta Key Rental
Very clean, nice size bedrooms, great location. Close to the beach, stores and restaurants. We really enjoyed our stay.
Debra B.
Stayed 3 nights in Mar 2024
Response from VrboOwner on 7 Apr 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
Verified
10/10 Excellent
Mary
30 Jun 2023
Liked: Cleanliness, amenities, property conditions & facilities, communication
Host was very detailed with instructions and upon arrival, was able to check-in smoothly. Property was clean and close to downtown & beach. Had a great stay!