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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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
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.
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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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
Siesta Key Snack Bar - 3 min drive
Circle K - 7 min walk
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 2 Apr 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 15 May 2026 start from £529, 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. St. Boniface Episcopal Church Labyrinth and Irma Beach are also within 2 miles (3 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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!
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.
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
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
This is a nice place to stay while visiting Siesta Key, with an unbeatable location. You can access the restaurants and shops in Siesta Key Village through a backyard gate, and the beach is just a short, easy walk down the street. We loved being able to walk down and watch the beautiful sunsets each evening.The house is well laid out with three bedrooms, plenty of space, and a comfortable family room where we could all watch TV together. There is nice patio seating in both the front and back, along with lounge chairs. It was also very convenient to have beach towels, beach chairs, and a wagon provided. The owners communicated well and were accommodating throughout our stay.A couple of things to note: the home shows some wear and is not as nice as the pictures suggest, and you can hear music from the nearby bars at night, especially in the back bedroom. That said, overall our family enjoyed our stay and would recommend it for anyone wanting to be close to the village and beach.
Verified traveller
Stayed 5 nights in Dec 2025
Response from VrboOwner on 7 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
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
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
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!
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!
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!
From a partner site
10/10 Excellent
Kary G.
27 Jun 2025
Great Location
We just returned from a 4 night stay at the cottage which was excellent! 2 minute walk to the beach and 2 minute walk to the village which has a great little market and lots of local shopping. We parked and never left. Dan responds so fast, we had no issues. Dog friendly, clean, and lots of great neighborhood restaurants nearby.
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!
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
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.
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
Right in heart of village, very convenient location to beach, too. Efficient space with plenty of beds for a group.
Jon D.
Stayed 3 nights in Mar 2025
Response from VrboOwner on 22 Apr 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
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
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.
We loved our stay at Gertrude's Village House. The location is fantastic. Just a short walk to the beach and to the village where there is easy access to restaurants and shopping. The house was a perfect size for our family and the sunsets on the beach were amazing. Highly recommend Gertrude's Village House.
Jennifer L.
Stayed 4 nights in Feb 2025
Response from VrboOwner on 10 Mar 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!