Entire home

Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!

Family-friendly holiday home in Siesta Key with a water park

Photo gallery for Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!

Beach nearby
Terrace/patio
Smart TV, offices
Interior
Bar (on property)
At Gertrude's Village House, immerse yourself in a Siesta Key experience like no other. Three private patios offer the perfect setting for alfresco dining, sun lounging, and relaxing with a cocktail. With direct access to the village and its world-famous dining and entertainment options just steps away from award-winning beaches with calm azure waters.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Parking available
  • Pet-friendly
  • Dryer
  • Washer
  • Air conditioning
  • Outdoor space

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

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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.

Property amenities

Beach

  • Beach nearby

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • In-room accessibility
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city centre
  • Near a hospital
  • Near a zoo
  • Near the marina
  • Near the sea

Things to do

  • Water park
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Theme park nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

Similar properties

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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 is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

758690

About the area

Map
Siesta Key, FL

What's nearby

  • Siesta Key Beach - 2 min walk - 0.2 km
  • Shell Beach - 4 min drive - 3.1 km
  • Crescent Beach - 6 min drive - 5.1 km
  • St. Armands Circle - 18 min drive - 15.6 km
  • Lido Beach - 20 min drive - 17.7 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 32 min drive

Restaurants

  • ‪Circle K - ‬7 min walk
  • ‪Gilligan's Island Bar & Grill - ‬3 min walk
  • ‪Siesta Key Oyster Bar - ‬3 min walk
  • ‪Sun Garden Cafe - ‬6 min walk
  • ‪The Big Tiki Lounge - ‬3 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.

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. Irma Beach and Siesta Key Beach Playground are also within 2 miles (3 km).

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Reviews

Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village! Reviews

9.8

Exceptional

9.8

Cleanliness

10

Location

9.8

Property conditions & facilities
Rating 10 - Excellent. 141 out of 159 reviews
Rating 8 - Good. 14 out of 159 reviews
Rating 6 - Okay. 2 out of 159 reviews
Rating 4 - Poor. 1 out of 159 reviews
Rating 2 - Terrible. 1 out of 159 reviews

Reviews

10/10 Excellent

Brandi K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

Fantastic location & great host!
Stayed 6 nights in Apr 2025

10/10 Excellent

Robin B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun in the Sun

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!
Stayed 3 nights in Jun 2025

10/10 Excellent

Bradley

Liked: Cleanliness, amenities, property conditions & facilities, communication
Perfect location to the beach and dinning options

10/10 Excellent

Elizabeth M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dog friendly beach getaway

close to restaurants, bars, shopping, and beach!
Stayed 4 nights in Jul 2023

10/10 Excellent

Cliff L., Columbus, Georgia

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location!

The property is located in a great area convenient to the beach, restaurants, shopping and more.
Stayed 5 nights in Jun 2023

10/10 Excellent

Gail M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous

This property is everything it says it is and MORE!! Truly just steps away from the village and the beach. Lots of room wonderful patio area, etc... and there are not enough words to say about the property manager. I would rent this place or any place they have again. They even accommodate me on arriving a night early. You guys are the best!!!
Stayed 5 nights in Mar 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Debra B.

Siesta Key Rental

Very clean, nice size bedrooms, great location. Close to the beach, stores and restaurants. We really enjoyed our stay.
Stayed 3 nights in Mar 2024

10/10 Excellent

Amanda C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic location!

My family loved the house and perfect location! Easy walk to the beautiful beach and Siesta Village!
Stayed 3 nights in Mar 2023

10/10 Excellent

Mary

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!
Stayed 2 nights in Jun 2023

10/10 Excellent

Ellie N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved this place!

The location was amazing! It is so close to everything! The process of checking in and out was super easy! Would definitely come back!
Stayed 4 nights in Mar 2023

10/10 Excellent

Todd H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Siesta Getaway

Location was fantastic. Unit was clean and sufficient for our stay. I would stay again and recommend this property!!
Stayed 7 nights in Nov 2022

10/10 Excellent

Wendy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time

The place was easy walk to beach and restaurants…even for my 84 year old father. We had a wonderful visit!
Stayed 4 nights in Feb 2023

10/10 Excellent

Stacey M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous place!

What a beautiful place and amazing location in the north Siesta key village! Everything was within walking distance! Wonderful host with lots of amenities and extras!! I would definitely stay there again!
Stayed 3 nights in Jul 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Sabrina S.

5 stars!

Ideal location and really appreciated not having to clean before check out

10/10 Excellent

Cindy E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

2024 Stay

Great Location, easy instructions provided by owner and everything was as on the listing. Great experience with this property.
Stayed 2 nights in Jan 2024

10/10 Excellent

Mark W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A comfortable house in a fantastic location

Would highly recommend this house for a family looking to make the most of the beach and village of Siesta Key. Very thoughtful and comfortable home with some unique benefits. We especially loved the two parking spaces and the private entrance to the main drag of the village. So convenient to the beach and the best of Siesta Key.
Stayed 5 nights in Feb 2024

10/10 Excellent

Celia D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A fabulous Siesta Key vacation

My two grown sons and three-year -old granddaughter loved our stay at this amazing beach house just a short walk from the beach and the Village. It was spotless, comfy, and had everything we needed, and our host Dan was very responsive. We’d love to book this house again
Stayed 6 nights in Nov 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Choice

Gertrude Village House was absolutely perfect place and location!! It has everything you need and is located close to the beach and Siesta Village!! We will definitely come back and Dan was super responsive to texts and very helpful!!!
Stayed 5 nights in Jun 2023

10/10 Excellent

Nancy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and outdoor space!

We throughly enjoyed our stay - the beach and the village were closer than we even anticipated! The outdoor patio space was just perfect for our desire to be outside. Our only suggestion (and it really didn’t matter to us) is that I think the listing does state that there is a tub/shower in both baths, but one bath is just a large shower. Great place!
Stayed 4 nights in Nov 2023

10/10 Excellent

joe d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Experience

The property and location were beautiful and Dan Jones was quickly accessible and wanted to make our stay memorable. Thanks for a great vacation. I would recommend it.
Stayed 2 nights in Apr 2023

10/10 Excellent

Diane s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun time with family

The 7 of us loved our stay at Siesta Key. The house was in the perfect location, just 2 minutes walking to the large beautiful public beach and a couple of minutes to the center of town. Dan was very helpful and immediately available when we had a small plumbing issue. We'd love to return next year.
Stayed 3 nights in Jan 2024

10/10 Excellent

Carly T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet yet close to everything

Even though we were only one block behind the bustling main drive with lots of traffic, the home was exceptionally quiet and peaceful. It was very clean with enough space for the family to have space. Very short walk to the beach with a wagon and umbrellas and chairs (though we brought our own). The only negative was the water pressure in the shared bathroom, but the master bath shower was good. Loved that there was also an outside shower to help avoid tracking in sand.
Stayed 4 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

8/10 Good

Mary N.

Family fun

If very good was a choice that's what I would choose. The only reason I give this a good rating is because it was a little snug for 8 adults 4 that were over 60 which we thought when we booked. We Loved the outside patios. The location was great two blocks to beach or village. We had all the beach equipment we needed and an outside shower and even a gas grill . Any questions or problems were handled fast. Our vacation was enjoyable and relaxing. Can't wait to try another property
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Nikki D.

Can't wait to stay again!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Perfect home in a perfect little piece of heaven!! Two larger bedrooms are at opposite ends of the home so perfect layout for many traveling scenarios. The wine was just the cherry on top (and very quickly consumed)! Thank you for sharing your lovely rental home with me! I will 100% book here again!

10/10 Excellent

kristi d., United States

Liked: Check-in, communication, location, listing accuracy

Perfect location, beautiful beach

You really can't beat the location of this property. Group of 5 girlfriend's stayed here for 4 nights and we had everything we needed for an excellent stay. A short walk to the beach and just steps to the adorable little village where you'll find restaurants, shopping and a grocery store. The unit had everything we needed. It was well appointed with beach chairs, big fluffy beach towels and a wagon to haul everything to the beach. Communication with the owner was wonderful. The only issue we had was with cleanliness of the unit; the owner was appreciative of the feedback and promised to attend to it right away.
Stayed 4 nights in Oct 2022