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

Siesta Key, Florida
$424 avg/night
Minimum Stay 2 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 2 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly Service Animals Exempt From Fees
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi, With Speed Of 50+ Mbps
  • OUTDOORS

    Barbecue Grill Patio
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • WORKSPACES

    Desk Desk Chair Office
  • LANGS SPOKEN

    English French
  • THINGS TO DO

    Birdwatching Nearby Ecotours Nearby Kayaking Nearby Marina Nearby Parasailing Nearby Sailing Nearby Scuba Diving Nearby Swimming Nearby Water Park Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village In The City Center Near A Hospital Near A Zoo Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Wheelchair Accessible

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • William

    Submitted May 16, 2026

    Stayed May 11, 2026

    Excellent location for our visit. Close to the beach and restaurants.

  • Jacquelene

    Submitted Dec 7, 2025

    Stayed Dec 4, 2025

    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

  • Mary

    Submitted Jun 30, 2023

    Stayed Jun 23, 2023

    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!

  • Bradley

    Submitted May 16, 2023

    Stayed Dec 31, 1969

    Perfect location to the beach and dinning options

  • Deanna

    Submitted May 24, 2022

    Stayed May 14, 2022

    The property was close to the village and the beach. It was clean and well kept.

  • Sheri

    Submitted May 22, 2022

    Stayed May 19, 2022

    Beautiful location. Close walking to beach, resteraunts and shops.

  • free

    Submitted Feb 20, 2022

    Stayed Feb 10, 2022

    A perfect location. No need for a car at all

  • Submitted Aug 19, 2021

    Stayed Aug 9, 2021

    Thank you very much Dan for letting us stay at your house. Our stay was wonderful, the house is more beautiful in person than in the pictures it did not lack anything, everything you needed to have a good vacation has it. The siesta location is perfect, less than 5 minutes to the beach. Our children and friends had a great time. We will definitely return another time. We recommend it 100 percent.

  • Penelope M.

    Submitted Apr 28, 2026

    Stayed Apr 24, 2026

    Quick walk to the beach and the village, would definitely recommend this property! Plenty of beach chairs, towels, and everything we could need!

  • Kelly C.

    Submitted Apr 10, 2026

    Stayed Apr 7, 2026

    Such a cute beach house. You can’t beat the location ! We had such a great time and would book again

  • Jen G.

    Submitted Apr 7, 2026

    Stayed Apr 1, 2026

    We came at probably the most expensive rental rate time of the year over Easter. This location as others have mentioned is excellent. However it was SO loud. I imagine it’s because it was a very popular spring break time of the year, but they were loud house parties around us as well as the bars. Downtown is right out the back gate with more than enough restaurants, ice cream, shopping, etc. The beach is super close, and big but not too big. The listing pics are definitely not reality. The bedroom with the king bed does not have a bathroom, that is not clear in the listing. The kitchen has very basic supplies and was missing a cutting board; maybe one was there at some point. The AC is great!! Only one of the two beach umbrellas was functional, otherwise beach supplies are fine. Bikes were rusty and not usable; b/c of the salty air no doubt, but they need attention. Also, there were prior renter’s water bottles. Chapstick, and other things left under the beds. Host is super responsive and helpful, very kind as well. Check in/out was extremely smooth and simple! I would possibly stay there again but not at that rate.

  • Boxwood I.

    Submitted Mar 28, 2026

    Stayed Mar 23, 2026

    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!

  • richard b.

    Submitted Mar 17, 2026

    Stayed Mar 4, 2026

    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.

  • Greg D.

    Submitted Mar 12, 2026

    Stayed Mar 9, 2026

    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.

  • Deanna

    Submitted Feb 11, 2026

    Stayed Feb 7, 2026

    Absolutely recommend staying with Gertrude properties!!! Clean, close to everything. Planning our next stay and will only book with Gertrude properties♥️

  • Submitted Jan 10, 2026

    Stayed Dec 25, 2025

    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.

  • Todd W.

    Submitted Jan 3, 2026

    Stayed Dec 30, 2025

    Nice place, good location, property matched the description.

  • Submitted Oct 11, 2025

    Stayed Oct 6, 2025

    So close and convenient to shopping, dining choices and the beach!

  • Kary G.

    Submitted Jun 27, 2025

    Stayed Jun 22, 2025

    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.

  • Robin B.

    Submitted Jun 17, 2025

    Stayed Jun 12, 2025

    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!

  • Lisa R.

    Submitted Apr 27, 2025

    Stayed Apr 21, 2025

    We had such a great stay. The house is in the perfect location to the beach and town . Everything is just a short walk away. It was a plus that the house came w beach chairs and all the accessories needed for the beach . We will definitely be back! Also the owner, Dan was super responsive and helpful to any questions we had.

  • Brandi K.

    Submitted Apr 13, 2025

    Stayed Apr 5, 2025

    Fantastic location & great host!

  • Gail M.

    Submitted Mar 31, 2025

    Stayed Mar 26, 2025

    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!!!

  • Jon D.

    Submitted Mar 17, 2025

    Stayed Mar 14, 2025

    Right in heart of village, very convenient location to beach, too. Efficient space with plenty of beds for a group.

  • Joan S.

    Submitted Feb 21, 2025

    Stayed Feb 17, 2025

    We loved this place. It is an airy cottage type of home with enough space to gather a group of six for happy hour comfortably. We took advantage of the outdoor seating in both the front and the back of the home during our stay. The home has a great beach cottage vibe to it. The location is perfect as it is just steps from the village and all it has to offer . Daniel was a great host and available immediately when I called with a question.

  • Jennifer L.

    Submitted Feb 18, 2025

    Stayed Feb 13, 2025

    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.

  • Jeffrey C.

    Submitted Feb 13, 2025

    Stayed Feb 9, 2025

    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!

  • Submitted Feb 11, 2025

    Stayed Feb 6, 2025

    Accomodation was clean and nice. Perfect location between beach access and commetcoal area. Had a couple door lock problems and staff were right on addressing. People were very easy to deal with.

  • Elizabeth D.

    Submitted Feb 4, 2025

    Stayed Jan 18, 2025

    Location is the outstanding attribute for my family. Showed really good condition considering the storm damage suffered by so many. Kitchen is a bit undersupplied, but the main lack was attended to within 10 minutes. You folks are so, so helpful and prompt in response to any issues. We re-upped for same unit for 2026. Can't imagine life there with more than the three (will concede one or two more) of us unless most aren't there except to sleep! The three huge round platters in the utensil cupboard seem extraneous! The two black coated frying pans should be replaced. My sons wished there had been an exhaust fan in the hall bath. We were comfortable enough, and the hvac was easy to operate. We must love you because you have served us well for three rentals and we can't wait for next January! Betty

  • Steven M.

    Submitted Jan 20, 2025

    Stayed Jan 11, 2025

    Great property in a perfect location close to the beach and close to Siesta Key Village. Everything is within walking distance. Gertrude Rentals was very easy to work with and very responsive to questions prior to and throughout our stay. We will definitely be coming back.

  • Janelle W.

    Submitted Dec 29, 2024

    Stayed Dec 20, 2024

    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.

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Total

Includes taxes and fees
$473+
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