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

Top rated by guests
Siesta Key 3BR vacation rental  near the beach with private patios.
Open living area with mid-century modern decor.
Open living and dining area with TV, kitchen and patios on two sides.
Kitchen with all major and minor appliances.
Sunny breakfast bar for three and dining area with modern paintings.
review stars
9.7Outstanding
(168 Ratings)
"Excellent location for our visit. Close to the beach and restaurants."
William
Don't miss out! Price and availability may change
9.7 / 10
Outstanding(168 Ratings)

House in Siesta Beach

10 guests · 3 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this house rental

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.

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

Non-smoking
Pets allowed
Family friendly

Map of Siesta Beach


Ratings and reviews

9.7 / 10
Outstanding(168 Ratings)
10 / 10Outstanding·May 2026
Excellent location for our visit. Close to the beach and restaurants.
10 / 10Outstanding·Apr 2026
Quick walk to the beach and the village, would definitely recommend this property! Plenty of beach chairs, towels, and everything we could need!
10 / 10Outstanding·Apr 2026
Such a cute beach house. You can’t beat the location ! We had such a great time and would book again
8 / 10Excellent·Apr 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.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Gertrude's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.