Entire home

Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

Choose dates to view prices

Photo gallery for Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

4 bedrooms, desk, iron/ironing board, travel crib
Smart TV, books, offices
Exterior
Beach nearby
Interior

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms5 bathroomsSleeps 13

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Siesta Key, FL
  • Place, Siesta Key Beach
    ‪2 min walk‬
  • Place, Siesta Key Farmers Market
    ‪3 min walk‬
  • Place, Irma Beach
    ‪2 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪28 min drive‬

Room options

About the neighborhood

Siesta Key

Located in Siesta Key Village, this vacation home is adjacent to Siesta Key Beach and within a 5-minute walk of Siesta Key Farmers Market. The vacation home includes a kitchen, a balcony, and a sofa bed.

What's nearby

  • Siesta Key Beach - 2 min walk - 0.1 miles
  • Siesta Key Farmers Market - 3 min walk - 0.2 miles
  • Irma Beach - 2 min drive - 1.1 miles
  • St. Boniface Episcopal Church Labyrinth - 3 min drive - 1.5 miles
  • Siesta Key Beach Playground - 3 min drive - 1.3 miles

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 33 min drive

Restaurants

  • ‪Siesta Beach Pavilion - ‬3 min drive
  • ‪Siesta Key Snack Bar - ‬3 min drive
  • ‪Circle K - ‬5 min walk
  • ‪Gilligan's Island Bar & Grill - ‬5 min walk
  • ‪Sun Garden Cafe - ‬4 min walk

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 | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

Las Ventanas
Resort-like setting with semi-private pool, rooftop deck, in-house elevator, and 5 terraces in heart of Siesta Village! Just 1-minute walk to Siesta's best Beach and the shopping dining and entertainment of the village! Spacious, bright, airy, and surrounded by palms. Experience Siesta Key's top attractions without sacrificing space and comfort. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta

What Guests Love
∙ Terraces and Rooftop –beautiful views from five balconies and rooftop terrace
∙ Semi-private Pool – heated pool and sun shelves shared with just one other unit
∙ The Beaches – 1-minute to Siesta Key's top beaches with white sand and calm clear water
∙ Restaurants – 1-minute walk to the shopping dining and entertainment of the Siesta Village
∙ Gulf Breezes –Ventanas means “Windows” and 3000 ft.² of windows catch sea breezes day and night
∙ Relaxing – 5 baths and a balcony off every bedroom
∙ Sunsets –walk 1-minute to best sunsets or just enjoy from your rooftop deck
∙ Activities – a few free bikes and paddleboards provided, but scooter and golf cart rentals nearby
∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch
∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts
∙ The Memories – walk to all Siesta Key's top attractions and guaranteed fun for all

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 Location
You aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities, this property will deliver what they need. It's just steps to the top attractions on the island including 4 beach accesses, and 20 bars and restaurants. Walk right 450ft to the best beaches in America or left 450ft to the world-famous shopping dining and entertainment of the Siesta Key Village. This area has - ice-cream, tide pools, daiquiris, dolphins, fresh oysters, white-quartz-sand, big breakfast, sunsets, amazing seafood, white lagoons, craft beer, sand dollars, live music, shopping, and gourmet donuts. Back at the house, you'll enjoy a semi private pool (shared with just one other unit), as well as private features including - four private gathering areas for your bonding enjoyment including a poolside swim-out room with wet bar, and a rooftop sundeck with ocean views and wet bar. When you'd prefer to relax, you'll find lots of bright and airy out the way rooms and terraces for quiet decompressing.

Bedroom Details
This is a huge 4BR, you can sleep up to 13 family style. The master suite (large) has two queen beds with bath en-suite, a twin bed in the alcove and a large terrace. Bedroom #2 has a king bed and terrace. Bedroom #3 has a queen bed with bath en-suite and a terrace. Bedroom #4 is a swimout apt with a queen bed, living room, TV, full bath en suite, and private lanai poolside.

Beach Gear Provided
We provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. 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.

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.
The vacation home is air-conditioned and features a kitchen, 5 bathrooms, and a balcony. There's space to spread out with 4 bedrooms and a dining area. Guests can enjoy a Smart TV and stay connected with free WiFi. The bathroom offers a jetted tub and hair dryers. Other standard amenities include a washing machine, a sofa bed, and a coffee maker.

Similar properties

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Jetted bathtub
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill

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.
  • Elevator
  • Wheelchair accessibility
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city center
  • Near a hospital
  • Near a zoo
  • Near an outlet shopping mall
  • Near the marina
  • Near the sea

Things to do

  • Bicycles
  • Heated pool
  • Kayak
  • Optional golf privileges
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Ice skating nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling 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

General

  • Bicycles

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in 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
Information provided by the property may be translated using automated translation tools

Pets

  • This property welcomes pets
  • Service animals exempt from fees

Children and extra beds

Children allowed: ages 0-17

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
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
  • Check-in: 3:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 21

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock.

Property is also known as

758693

Frequently asked questions

What can I see around this vacation home?

This vacation home is situated in Siesta Key Village, just steps from Siesta Key Beach and Siesta Key Farmers Market. You'll also find Crescent Beach and Siesta Key Marina within a short drive.

Is parking available on site at this vacation home?

Yes, there is a garage.

Is this vacation home next to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

Is Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! a good place to stay for couples?

Couples will appreciate amenities at this vacation home, including a jetted bathtub and a kitchen in each accommodation with some featuring ocean views.

Does Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! have a hot tub?

No, but this vacation home offers jetted bathtubs in all accommodations.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

Although pets can't stay for free, they are welcome at this vacation home.

Does this vacation home have connecting rooms?

No, there aren't connecting rooms at this vacation home.

How far is the airport from this vacation home?

The closest major airport to this vacation home is Sarasota-Bradenton Intl. Airport (SRQ), which is 10.3 mi away (33 minutes by car).

Are there rooms with balconies that I can book at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?

Yes, every accommodation at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! comes with a balcony with some featuring ocean views.

Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 43 out of 48 reviews
Rating 8 - Good. 5 out of 48 reviews
Rating 6 - Okay. 0 out of 48 reviews
Rating 4 - Poor. 0 out of 48 reviews
Rating 2 - Terrible. 0 out of 48 reviews

9.8/10

Cleanliness

Reviews

8/10 Good

William C.

Liked: Cleanliness
good host good amenities
Stayed 13 nights in Feb 2026

10/10 Excellent

Eric M.

Liked: Cleanliness
Great place to stay! The family and I had an awesome week!
Stayed 7 nights in Jan 2026

8/10 Good

Susan M.

Liked: Cleanliness
The house was in a great spot. Easy to walk to beach, shopping and restaurants.
Stayed 4 nights in Nov 2025

10/10 Excellent

Miguelina V., Miami, FL

Liked: Cleanliness
Amazing location!! Had a beautiful time with friends and family.
Stayed 3 nights in Oct 2025

10/10 Excellent

Kimberly C.

Liked: Cleanliness
Gertrude’s Siesta was a perfect gathering place for our crew of adults on an R&R getaway! We loved both the common space and that fact that the bedrooms were located on separate floors affording some privacy. Great property!
Stayed 3 nights in Oct 2025

10/10 Excellent

Jeanine C.

Liked: Cleanliness

Perfect family location for a Siesta Key Wedding

Our five-night stay at Gertrude's Siesta provided the perfect balance of convenience and relaxation as we celebrated our daughter's wedding on SK Beach. The property offered ample space for our nine family members, who ranged in age from 26-86. The elevator provided safe and easy access to the four floors, particularly when moving luggage and items for the reception. Communication and coordination with the owner and local manager was outstanding, particularly when additional household items were needed, e.g., bath towels, dish towels, hot pads, kitchen faucet required replacement, and floors needed to be cleaned. All requests were handled quickly and satisfactorily! We enjoyed the close proximity to the beach and local shops and restaurants. We appreciated the beach extras in the garage, especially the wagons! We thoroughly enjoyed our stay and look forward to staying again.
Third floor double queen and twin bedroom with balcony and large bathroom
Third floor bathroom with walk in shower and soaking tub
Stayed 5 nights in Jul 2025

10/10 Excellent

Cassandra P.

Liked: Cleanliness
We stayed a week with a family of 11.We absolutely loved it something for everyone. Close to anything you need within walking distance. Easy in and easy out. Would stay again. Lots of memories.Owner very responsive to anything you might need.
Stayed 6 nights in Jun 2025

10/10 Excellent

Aaron C., Scituate, Massachusetts

Liked: Cleanliness

Great house, perfect location

House is equidistant from the beach and the major retail area in Siesta Key - about a block and a half each way. Perfect spot for our two families with four teenage boys. The kids could walk to the beach or go out to dinner on their own and we got some much appreciated adult time. The house itself was beautiful and clean. Tons of chairs and towels for the beach and wagons to haul them in. Four bicycles, a couple paddleboards - really all you need for a great beach vacation. Plenty of room in the house for 8 of us. The pool and outdoor space were ample and everything was in nice shape. Hosts were friendly and responsive.Thumbs up overall - would definitely stay here again.
Stayed 4 nights in Apr 2025

10/10 Excellent

Melissa R.

Liked: Cleanliness

Wonderful stay

We had the best family vacation! This location is perfectly situated between the beach and restaurants/bars. We had a great stay!
Stayed 3 nights in Sep 2024

10/10 Excellent

josh r.

Liked: Cleanliness

Great place!!

We loved our stay here. Host had plenty of beach toys for our family. Great location to beach and town. Would stay here again!
Stayed 3 nights in Aug 2024

8/10 Good

Juan J. L.

Liked: Cleanliness

Siesta vacation

Great location however small pool that is shared with another property with no privacy is a huge con of this proper, also need more attention to cleanliness of pool. If you dont need a pool location is great between beach and Siesta village.
Stayed 3 nights in Aug 2024

10/10 Excellent

Olivia F.

Liked: Cleanliness

One of a kind!

What can’t I say about this place! This place was absolutely amazing. We had 14 ladies sleeping comfortably, with also plenty of space to shower and get ready. We were amazed at the number of areas and balconies to spend time and relax on! It is walking distance to so many places (coffee, restaurants, bars, beach, grocery store & shopping)! It was a quick 25 minute drive from Sarasota airport, after that no car would be needed. The area was very clean and safe to walk around as well! Dan was also amazing, very easy to communicate with. We didn’t have to worry about stripping the beds/linens, washing towels or cleaning up (not many places you can rent do that). It made our last day so much more enjoyable to relax and hangout at the pool and beach! We are already taking about coming back. Thanks again!
Stayed 4 nights in May 2024

8/10 Good

sharon g.

Liked: Cleanliness

Girls trip

50+ age, ladies celebrating upcoming wedding for bride to be. Plenty of room for 9 women. Its a duplex, neighbors were very nice. Parking spot if rent car. VRBO contact very responsive. Perfect location for walk to town and beach.
Stayed 5 nights in Apr 2024

10/10 Excellent

Brenda B.

Liked: Cleanliness

Amazing

11 ladies for a Girls weekend. Everyone loved this place it was close to EVERYTHING! We all had beds to sleep in. Dan and is staff were so helpful. And nothing better than checking out and not have to worry about a thing. Thanks Dan
Stayed 3 nights in Apr 2024

10/10 Excellent

Kay P.

Liked: Cleanliness

Spring Break

We had an awesome time and the accommodations were as advertised
Stayed 6 nights in Mar 2024

10/10 Excellent

Andrea Q.

Liked: Cleanliness

Family Vacation

The property was wonderful. The house is large and accomodates many people. The beach and Village were nice and close. I would highly recommend this property for a large group and would utilize again if available.
Stayed 5 nights in Feb 2024

10/10 Excellent

Renice S.

Liked: Cleanliness

Loved our stay!

Beautiful property with walking distance to all you need.
Stayed 3 nights in Feb 2024

10/10 Excellent

Mark S.

Liked: Cleanliness

Fabulous location and property

Clean, easy to use, management was responsive to our 1 request for additional blankets. Would use again.
Stayed 3 nights in Feb 2024

10/10 Excellent

Chris M.

Liked: Cleanliness

Nice spot, nice place

Great comms from the host and the house was lovely overall. We would stay again. There were a few things that we might have expected to be provided (e.g. shampoo) that were not but that was probably an oversight on our part in the listing. Cleanliness could be improved a tiny bit in the bathrooms and the quality of the soaps (given the impressive nature of the place) was a bit disappointing. But it's a beautiful spot, host communication was superb, the bikes etc. in the garages are great and everything worked very nicely.
Stayed 4 nights in Jan 2024

8/10 Good

Tawnya W.

Liked: Cleanliness

Lots of Space!

This home is beautiful with a great location! We went with 12 in our group ranging from 1 year old to 73, enough space for all for sure but everything is on a different level of the home so you use alot of stairs. There is an elevator but was not working the entire week we stayed so that was a problem with a toddler and grandparents. The beach is beautiful & a short walk! Located within walking distance to many different restaurants and shopping as well. The beds my family of 5 used were OK. The host was responsive & easy to get in touch with.
Stayed 7 nights in Dec 2023

10/10 Excellent

Rebecca B.

Liked: Cleanliness

Great family beach vacation

So many great attributes of this beach rental - Perfect location between Sunset Beach and the village - Lots of room for big groups - Great host with helpful communications - Check-in and house access were super easy - Everything you need for the beach Highly recommend! We would love to stay again
Stayed 4 nights in Dec 2023

10/10 Excellent

Carol F.

Liked: Cleanliness

Very helpful

Dan really helped us by letting us check into the property a little early in order to accommodate our grandchildren with special needs. We are so grateful! Lovely property in a great location.
Stayed 3 nights in Oct 2023

10/10 Excellent

Lauri H.

Liked: Cleanliness

Awesome Location

Had a bachelorette event consisting of 12 girls. The house was perfect for sleeping arrangements and everyone able to be in one location in the living room. Elevator was working upon check-in, called “Dan”, within 5 minutes he had the technician there to fix it. Such great customer service. Exceptional communication. The location was perfect! Walked to town (great little town). Walked to the beach. Everything you would need for beach trip was there. Everyone loved it!!! Would definitely go back and would book through Gertrude Rentals with Dan!
Stayed 3 nights in Sep 2023

10/10 Excellent

Deanna O.

Liked: Cleanliness

Beautiful house

Great location
Stayed 3 nights in Jul 2023

10/10 Excellent

Nicole P.

Liked: Cleanliness

Summer fun

Great trip and great home!
Stayed 4 nights in Jun 2023