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

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Outdoor dining
Just 500ft to Siesta Key beach, Siesta Key Village 4BR
Private sundeck with wet bar, wide-open Westerly exposure, and a glimpse of the ocean - Siesta Key Village 4BR
Pool
Gertrude - One name, numerous possibilities!

Reviews

10 out of 10
Exceptional
4 bedrooms3+ bathroomsSleeps 13

Popular amenities

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

Explore the area

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

Rooms & beds

4 bedrooms (sleeps 13)

Bedroom 1

1 King Bed

Bedroom 2

2 Queen Beds

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Common Space

1 Single Bed and 1 Double Sofa Bed

3 bathrooms, 2 half bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Toilet · Shower only

Half Bathroom 4

Toilet

Half Bathroom 5

Toilet

Spaces

Deck or patio
Kitchen
Office
Balcony
Dining area

About this property

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 is 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.

Property manager

Gertrude Rentals 888-5SIESTA
Premier Host

Languages

English, French

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

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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 in Siesta Key Village, a neighbourhood in Siesta Key, this holiday home is near theme parks and near the beach. 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. Mote Marine Laboratory & Aquarium and Coconuts Family Entertainment Center are also worth visiting. 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
  • Shell Beach - 8 min drive - 3.1 km
  • Crescent Beach - 14 min drive - 4.9 km
  • St. Armands Circle - 17 min drive - 14.1 km
  • Lido Beach - 34 min drive - 16.9 km

Getting around

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

Restaurants

  • ‪Gilligan's Island Bar & Grill - ‬5 min walk
  • ‪Siesta Key Oyster Bar - ‬5 min walk
  • ‪Siesta Key Beach Pavilion - ‬3 min drive
  • ‪The Old Salty Dog - ‬6 min walk
  • ‪Daiquiri Deck Siesta Key - ‬5 min walk

Frequently asked questions

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

Yes, this property has a pool. Pool types include heated pools.

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

Yes, pets are allowed at this property.

What time is check-in at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?

Check-in begins at 3:00 PM.

What time is check-out at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?

Checkout is at 10:00 AM.

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

Located in Siesta Key Village, this holiday home is within 1 mi (2 km) of Siesta Key Farmers Market and Siesta Key Beach. Irma Beach and Siesta Key Beach Playground are also within 2 miles (3 km).

Reviews

10

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. 36 out of 37 reviews
Rating 8 - Good. 1 out of 37 reviews
Rating 6 - Okay. 0 out of 37 reviews
Rating 4 - Poor. 0 out of 37 reviews
Rating 2 - Terrible. 0 out of 37 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

10/10 Excellent

Daniel R.

Our spring break rental

Really happy with place it was above and beyond with all it has to offer and team always ready to help with any of your necessities, they handled everything from start to finish this is really is a great place to stay and we definitely will be returning with Dan the man
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Linda W.

Perfect spot

We loved this house and it was at a perfect spot. Once we got there we never had to drive, everything was in walking distance.
Stayed 4 nights in Dec 2024

10/10 Excellent

Sheila K.

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

Wonderful place to stay in many a combinations and things to do

Wonderful place to stay
Stayed 3 nights in Jan 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Gretchen C.

Great place great location

We really loved this home to stay in for five nights. It was a two minute walk to the beach, two minute walk to the village. It was very spacious and clean. Unfortunately We did not have great weather to utilize all the multiple decks and the pool area. There is a great rooftop deck where we were able to see a beautiful sunset. We would definitely stay here again!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Amy S.

Our stay at this stunning gulf-view rental was absolutely perfect! The house offered breathtaking views of the sunset right from the spacious deck, making every evening feel magical. The interior was beautifully decorated, clean, and equipped with everything we needed for a comfortable stay. The location couldn't have been better — just a short walk to the beach, local restaurants, and lively bars. It was so convenient to enjoy a day on the sand and then head out for dinner and drinks without needing to drive. The host was incredibly responsive and thoughtful, ensuring we had everything we needed for an unforgettable getaway. If you're looking for a peaceful retreat with unbeatable views and easy access to local hotspots, this place is a gem. We can't wait to come back!

10/10 Excellent

Nick S.

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

Great Beach getaway

Great location! Walking distance the beach and restaurant's / bars in Siesta Key.
Stayed 4 nights in Oct 2023

10/10 Excellent

Thomas C.

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

Amazing location and property!

Amazing property and location!! We loved it! The parents and recent grads had a blast. Thank you!!
Stayed 4 nights in Jul 2024

10/10 Excellent

Erin B.

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

Fantastic location, home, and property manager

Location and amenities of the home were fantastic. Easy check-in and check- out made the vacation great from start to end.
Stayed 5 nights in Mar 2023

10/10 Excellent

K.L. R.

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

Great Place for a Mini Vacation from Tampa

Thank you for the excellent stay. We really enjoyed your property and would love to come back at some point!
Stayed 4 nights in Apr 2023

10/10 Excellent

Erin M.

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

Beach vacay

Had a great stay. The house was awesome loved being so close to the beach! Perfect rooftop view for the sunset too
Stayed 4 nights in Aug 2023

10/10 Excellent

Amy S.

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

Beautiful home in great location

We very much enjoyed our stay and management was immediately responsive to our communications.
Stayed 5 nights in Apr 2023

10/10 Excellent

Verified traveller

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

Quiet and Convenient

Great location within short walking distance to beach and local restaurants.
Stayed 3 nights in Jun 2023

10/10 Excellent

Andrew C.

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

Great stay

Had a fantastic time! Beautiful location steps from Gulf and restaurants. Daniel was excellent host and communicated throughout check in and check out process.
Stayed 4 nights in Dec 2022

10/10 Excellent

Grant S.

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

PRIME Location!!

The stay was perfect! Great accessories for the beach, walking distance to the restaurants and bars. Beach was a short walk as well! We loved the stay and would recommend it to anyone. The elevator was a cool touch as well it made it easy to fill a cooler and bring luggage to different floors. Really great communication and even let us drop our bags off a bit early which was awesome!!
Stayed 3 nights in Sep 2024

10/10 Excellent

Verified traveller

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

Amazing in every way!

Easy to check in and communicate. Perfect location, pool, and rooms. We will be back! Appreciate everything!
Stayed 4 nights in Jun 2024

10/10 Excellent

Pedro L.

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

Great Location and Clean house

We enjoyed our stay here very much. House was close to restaurants and the beach so we really didn’t have to drive around much. It was also nice to have a wagon to take our stuff to the beach as well as bikes to explore the area. I thought the pool was small but lots of other compensating factors.
Stayed 4 nights in May 2024

10/10 Excellent

Lisa A.

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

Siesta key birthday weekend

Great house, great location. Had everything we needed. Owner very responsive and easy to work with. Looking forward to staying in the house again.
Stayed 3 nights in Oct 2023

10/10 Excellent

Verified traveller

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

Very close to the beach!

My family and I stayed in this beautiful vacation home for memorial weekend and we were beyond satisfied with everything the home offered as well as the attentiveness of the host. My family and I loved how close the beach was and how the house is located right next to Siesta Key Village. We are already planning our next vacation to this lovely home.
Stayed 2 nights in May 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

p C.

great stay

Our entire interaction with Dan and the Gertrude team was great. The property was just as pictured, well maintained and extremely well stocked. Bikes, beach chairs, even coolers were provided. Definitely recommend Gertrude's and plan to come back soon.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Tara O.

Birthday Celebration

4 couples stayed in this beautiful home for a birthday celebration! Fantastic location, well appointed house, comfortable beds. Dan is an amazing host and responds quickly to random questions!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Karen S.

Loved our stay Siesta Key

We were a group of nine women enjoying fun in the sun. Our accommodations were perfect. Communication with Dan was superior. The heated pool was enjoyable. I would not hesitate to stay again. 5 stars 😊

10/10 Excellent

Carol A.

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

FANTASTIC

We loved the property! Perfect amount of space for 2 families with kids! So clean and perfect location. Easy walk for kids to beach and restaurants! We will be back!
Stayed 3 nights in Jul 2023

10/10 Excellent

Katie P.

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

Great vacation home

I highly recommend this property. The place was perfect for our family. The beach is 2 blocks away. Everything was great and I will definitely be back. Dan was great with communication. Everything ran very smoothly.
Stayed 4 nights in Jun 2023

10/10 Excellent

Debbie A.

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

Vaca

We had a great time. The villa had many extras bikes, ping pong , great kitchen
Stayed 3 nights in Jul 2023

10/10 Excellent

Elaine K.

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

Girls get away

Property was as stated, plenty of room, nice decor, close to everything, lovely pool, the beach accessories were a great touch! Wed
Stayed 4 nights in Apr 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