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

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King Master with Private Patio and gate into Village, Siesta Key Village 3BR
Siesta Key beach 500ft walk to access, Siesta Key Village 3BR
Sunny Alfresco Dining patio, Siesta Key Village 3BR
Shaded Living Area, Siesta Key Village 3BR
King Master with Private Patio, Siesta Key Village 3BR

Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Parking available
  • Beach view
  • Air conditioning
  • Pet-friendly
  • Dryer
  • Washer

Explore the area

Map
Siesta Key, FL
  • Siesta Key Beach
    ‪2 min walk‬
  • Crescent Beach
    ‪11 min drive‬
  • Lido Beach
    ‪36 min drive‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪32 min drive‬

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Bunk Beds

Common Space

1 Single Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Office
Separate dining area
Dining area

About this property

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.

Property manager

Gertrude Rentals 888-5SIESTA
Premier Host

Languages

English, French

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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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

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 Coconuts Family Entertainment Center. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Siesta Key, FL

What's nearby

  • Siesta Key Beach - 2 min walk - 0.2 km
  • Point of Rocks - 8 min drive - 5.6 km
  • Shell Beach - 8 min drive - 3.1 km
  • Crescent Beach - 11 min drive - 4.6 km
  • Lido Beach - 36 min drive - 16.9 km

Getting around

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

Restaurants

  • ‪Gilligan's Island Bar & Grill - ‬3 min walk
  • ‪Siesta Key Oyster Bar - ‬3 min walk
  • ‪Siesta Key Beach Pavilion - ‬3 min drive
  • ‪Starbucks - ‬10 min drive
  • ‪The Old Salty Dog - ‬8 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).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 136 out of 154 reviews
Rating 8 - Good. 14 out of 154 reviews
Rating 6 - Okay. 2 out of 154 reviews
Rating 4 - Poor. 1 out of 154 reviews
Rating 2 - Terrible. 1 out of 154 reviews

9.8/10

Cleanliness

9.8/10

Amenities

9.8/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

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

10/10 Excellent

Jon D.

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

As advertised

Right in heart of village, very convenient location to beach, too. Efficient space with plenty of beds for a group.
Stayed 3 nights in Mar 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Joan S.

Beach Cottage Vibes

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.

10/10 Excellent

Jennifer L.

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

Fabulous Location for a Beach Vacation

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.
Stayed 4 nights in Feb 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jeffrey C.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Great stay at Siesta Key

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.
This review comes from a trusted partner site and has not been verified.

8/10 Good

Elizabeth D.

Location, location, location

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

10/10 Excellent

Steven M.

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

Florida Getaway

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.
Stayed 5 nights in Jan 2025

10/10 Excellent

Janelle W.

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

A great space in a fun location

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.
Stayed 8 nights in Dec 2024

10/10 Excellent

Yvette D.

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

Amazing vacation! Great house!

The location is everything! We were very pleased with how clean the house is, and all the beach toys available to bring to the beach. Very comfortable property!!
Stayed 5 nights in Aug 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Hannah M.

Our favorite SK spot

Gertrude Rentals are the only place we will stay during our yearly Siesta Key visits! They offer the best locations in SK and are so helpful and accommodating throughout the entire stay. We can't wait to come back year!

8/10 Good

Tammy H.

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

Family Vacation

We had a great stay! The place was close to the beach and the village . We had everything we needed- chairs and a wagon which is nice when you come from a distance . Dan and Anna were great when we had a minor problem with the hot water which was fixed in a timely manner. Thank you so much .
Stayed 5 nights in Aug 2024

10/10 Excellent

Matthew M.

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

Great location

Clean, fun, plenty of extras.
Stayed 3 nights in Aug 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Julia P.

Fantastic location

House was clean and perfect location a quick walk to the beach and in the middle of downtown for restaurants/shops. The owners responded quickly anytime I emailed and they take care of everything! No long checklist for checking out either! Highly recommend!

10/10 Excellent

Deborah B.

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

Great Location

We especially enjoyed the location.
Stayed 5 nights in Jun 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

8/10 Good

John H.

Liked: Cleanliness, check-in, communication, location

Vacation

Great place! Pleased with my stay!
Stayed 6 nights in May 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

David S.

Siesta Key Vacation

Gertrude's Village House was the ideal spot for our recent vacation to Siesta Key. The location is unbeatable - just steps from the beach and directly connected to Siesta Key Village through a private gate. We loved leaving the car behind and strolling to the beach for swims and sunset walks. The village itself is charming, with plenty of shops, restaurants, and entertainment options all within easy walking distance. The house itself was beautifully decorated and had everything we needed for a comfortable stay. We especially enjoyed the private patios, which offered a tranquil space to relax and unwind after a day at the beach. The multiple patios provided both sun and shade, making them perfect for any time of day. Highlights: Unbeatable location - steps from the beach and Siesta Key Village Private patios with comfortable seating and beautiful landscaping Easy walking distance to shops, restaurants, and entertainment Nicely decorated and well-equipped house Overall, we had a fantastic experience at Gertrude's Village House and would highly recommend it to anyone looking for a relaxing and enjoyable vacation on Siesta Key. Additional Tips: The beach chairs and towels provided by Gertrude Rentals were a big plus! Be sure to check out the amazing sunsets from Siesta Key Beach. I hope this review helps you decide if Gertrude's Village House is the perfect place for your Siesta Key vacation!
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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

joyce P.

Great

Location was the best and we found the house very comfortable and inviting. Would stay again!!

8/10 Good

Catie W.

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

Great Location

Our stay was nice and the place is in a great location. Restaurants, coffee, groceries are all in your backyard and a very short walk. The beach is about a 2 minute walk down the street. I will say that the place itself is cute, but it is small. We had 8 people staying and I cannot imagine fitting any other bodies in the house, there isn't anywhere to place luggage so it's a tight squeeze. If you are out all day at the beach, then no worries, but if you are stuck inside with rain like we were, it's crowded. Check in was super easy and the owner provides a really nice guide book when you check in. Overall, a cute place with a great location and I'd stay again, but probably not with 8 people. Thank you!
Stayed 4 nights in Mar 2024
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

Alexis M.

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

Spring break family of 6

Clean, comfy beds, quiet even though right in siesta village, great location for shops, restaurants, and beach.
Stayed 4 nights in Mar 2024

10/10 Excellent

Tonia S., Lakeville

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

Wonderful

We were pleasantly surprised to see what an amazing location this is! Everything is within walking distance and the beaches are so beautiful. The unit was clean and comfortable- everything was as stated. The beach chairs/wagon/umbrella set up was perfect!! We slept great after full days soaking up the sun on the beach and then eating/shopping and exploring. We will be back!
Stayed 3 nights in Feb 2024

About the host

Hosted by Gertrude Rentals 888-5SIESTA

Host profile image
Dan Jones, "owner" Gertrude Rentals
Phone: (888) 5-SIESTA
Email: gertrude.rentals@gmail.com
Website: gertruderentals.com

Languages:

English, French

Premier Host

They consistently provide great experiences for their guests