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Gertrude's Siesta | Ocean-Views, Pool, 150-minute to Beach, Covered Patio, Private Elevator!

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Large kitchen and living area flows into ocean-view balcony, Siesta Key 3BR
Pool (shared), Siesta Key 3BR
Gertrude - One name, numerous possibilities!
Siesta Key beach 2-min walk, Siesta Key 3BR
Covered lounging with TV (private), Siesta Key 3BR

Reviews

9.8 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 10

Popular amenities

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

Explore the area

Map
Siesta Key, FL
  • Siesta Key Beach
    ‪2 min walk‬
  • Point of Rocks
    ‪6 min drive‬
  • Crescent Beach
    ‪9 min drive‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪34 min drive‬

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Common Space

2 Single Beds and 1 Double Sofa Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Half Bathroom 3

Toilet

Spaces

Kitchen
Office
Balcony
Separate dining area
Dining area

About this property

Gertrude's Siesta | Ocean-Views, Pool, 150-minute to Beach, Covered Patio, Private Elevator!

Hoppy's Ocean View
Beautiful ocean-view home in top location with pool! Just 1-minute walk to Siesta Key beach! 4-minute golf cart or free trolley ride to shopping dining and entertainment in Siesta Key Village. Balcony, alfresco dining and lounging, shared pool, and an in-house elevator. Perfect for families or couples who relax, explore and repeat. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta


What Guests Love
∙ Ocean Views – southwesterly ocean views from the balcony
∙ Beaches – 1-min walk to award winning beaches
∙ Relaxing – private balcony and patio with dining and lounging
∙ Pool – beautiful heated pool with tropical plants just 25 steps away
∙ Sunsets –walk 1-min to best sunsets or just enjoy from the balcony
∙ 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 – bikes, paddleboards, scooter and golf cart rentals nearby
∙ Island Trolleys –just 1-min walk to pick up, free of charge to all Siesta Key points
∙ The Memories – walk to all siesta key is top attractions and guaranteed fun for all

The Beach
Our beach has a quieter beach in front and to the right plus a lively popular crowd 50 yards south. It is a top spot on Siesta Key for sunsets and on Sundays the world-famous Siesta Key Drum Circle happens 100 yards down the beach. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.

The Home
Large 3BR home fully remodeled in 2023. Beautiful décor and thoughtful amenities throughout. Out-door grilling and dining, indoor and outdoor lounging, perfect for bigger groups, surrounded by palms. Set on the Southern edge of Siesta Village. Just 1-minute walk to top beaches, and 3-minute golf cart or trolly ride (15-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.

Bedroom Details
This ocean view property is three stories, living space on the second and third floor, and it boasts an in-house elevator to all floors. There is one large king bedroom, two queen bedrooms, a queen sleeper in the living room, a trundle under one of the queen beds and two Tempur-pedic rollaway beds. You can sleep up to 11 family style. 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, and umbrellas. 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, 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. Travelling with kids? Consider Mote Marine Laboratory & Aquarium, or check out an event or a game at Stardust Event Center. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Siesta Key, Florida

What's nearby

  • Siesta Key Beach - 2 min walk - 0.2 km
  • Siesta Key Marina - 5 min drive - 3.5 km
  • Point of Rocks - 6 min drive - 4.4 km
  • Crescent Beach - 9 min drive - 3.4 km
  • Lido Beach - 36 min drive - 18.7 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 34 min drive

Restaurants

  • ‪Gilligan's Island Bar & Grill - ‬13 min walk
  • ‪Siesta Key Oyster Bar - ‬14 min walk
  • ‪Siesta Key Beach Pavilion - ‬7 min walk
  • ‪Phillippi Creek Village Restaurant & Oyster Bar - ‬7 min drive
  • ‪Starbucks - ‬8 min drive

Frequently asked questions

Does Gertrude's Siesta | Ocean-Views, Pool, 150-minute to Beach, Covered Patio, Private Elevator! have a pool?

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

Is Gertrude's Siesta | Ocean-Views, Pool, 150-minute to Beach, Covered Patio, Private Elevator! pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Gertrude's Siesta | Ocean-Views, Pool, 150-minute to Beach, Covered Patio, Private Elevator!?

Check-in begins at 3:00 PM.

What time is check-out at Gertrude's Siesta | Ocean-Views, Pool, 150-minute to Beach, Covered Patio, Private Elevator!?

Checkout is at 10:00 AM.

Where is Gertrude's Siesta | Ocean-Views, Pool, 150-minute to Beach, Covered Patio, Private Elevator! located?

This family-friendly Siesta Key holiday home is located by the sea, within 1 mi (2 km) of Siesta Key Beach Playground and Siesta Key Beach. Siesta Key Farmers Market and St. Boniface Episcopal Church Labyrinth are also within 1 mile (2 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. 58 out of 62 reviews
Rating 8 - Good. 3 out of 62 reviews
Rating 6 - Okay. 0 out of 62 reviews
Rating 4 - Poor. 0 out of 62 reviews
Rating 2 - Terrible. 1 out of 62 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Kelli S.

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

Nice property

We had a great time visiting family in siesta. The unit was clean and very nice. Close to beach and town.
Stayed 4 nights in Mar 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Karl H.

Gem in Siesta Keys

Had a great stay at Gertrude rentals. Literally one block from the beach! Walk to town. Lots to do. Could not be happier. The house was immaculate and plenty of space for all of us. Thank you for making our stay wonderful.

10/10 Excellent

Alison S.

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

Perfect beach get away

The description of the property was perfect. Once you park, no need to use your car again. Plenty of beach gear to use, free trolly system, and it really was about 150 steps to the beach. We had a perfect time.
Stayed 3 nights in Mar 2025

10/10 Excellent

Tammy M.

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

Excellent Location

Location can’t be beat. Close to the beach and to town. Beautiful view as well! Definitely would stay again!
Stayed 6 nights in Jan 2025
This review comes from a trusted partner site and has not been verified.

8/10 Good

Tyler Y.

Nice relaxing stay

Overall a great stay with excellent customer service. A few minor things needed repair, but still recommend. We will for sure consider Gertrude for our next trip!

10/10 Excellent

Sonia D.

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

Great property!

Clean, well stocked, and close to town!
Stayed 5 nights in Sep 2024

10/10 Excellent

Jeff R.

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

Family Vacation

We booked this location so that we would be close to the beach. 150 steps gets you to the edge leading to the beach. We had someone with us that had difficulty walking so it was not as close as we had hoped. The beach and location is beautiful though, so if you can walk the extra steps will worth the walk. The beach did have a beach wheelchair available so we utilized that. The condo had a lot of beach chairs and toys available.
Stayed 7 nights in Feb 2025

10/10 Excellent

Cassie M.

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

Flexible Spaces

Great location, easy beach access, cute details!
Stayed 6 nights in Jun 2024

10/10 Excellent

William H.

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

Great location

Had a great time with the family within easy walking distance of an incredible beach. Plenty of room for a family of five.
Stayed 3 nights in Jul 2023

10/10 Excellent

George S.

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

Siesta get away

Place was great. Close to ocean and walking distance to town. Clean, spacious and plenty of amenities.
Stayed 4 nights in Feb 2024

10/10 Excellent

paul o.

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

Vacation getaway

Great location very clean and has everything you need
Stayed 3 nights in Apr 2023

10/10 Excellent

Bob S., Palm Beach Gardens, FL

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

Great rental! Would definitely stay again.

Clean, close to the beach and easy communication with the rental company.
Stayed 4 nights in Jul 2022

10/10 Excellent

Ashley T.

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

Great location

Dan couldn't have made everything easier for us. The house is great for families and the beach is stunning!
Stayed 4 nights in Feb 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Thomas M.

Siesta Key Long Weekend

We rented Gertrude 3BR home for 5 nights. I have to say, the house rental was completely spectacular. Very clean and well appointed with amenities. The best part was all the beach gear and wagons to be able to set up at the short walk to the beach. The shared pool with the home next door was great also. I would highly recommend Gertrude rentals and highly recommend Siesta Key as a destination.

10/10 Excellent

Laura S.

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

Siesta dream getaway

The property and the views are absolutely amazing! The pictures do not do it justice. The owner was absolutely amazing and extremely accommodating. 100%, would stay here again.
Stayed 5 nights in Mar 2024

10/10 Excellent

Debra B.

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

Best time!

We had a great time! Weather was fabulous as was our place! Host was great and very responsive. Short walk to the most beautiful beach ever! Will definitely be coming back!!
Stayed 5 nights in Apr 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Paula P.

Great

This place was amazing! It worked out wonderfully for our family! Everything you could possibly imagine was provided. We did not have to pack any sand/beach stuff. The house was sooo comfortable and clean. I would give this a 10 star review! Super easy access to the beach!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Alicia G.

Hoppy Beach AWESOME!!!

Amazing Time!!! So close to the beach! Beach gear / wagons / towels a plenty. Diana was a great resource! Condo was Perfect! Everything we coulda asked for & more!!!!! We'll be back!!!
Stayed 6 nights in Jun 2024

10/10 Excellent

Brian C.

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

Great location

My family agrees this was the best vacation rentals we stayed in. We had everything we needed for our stay at the house. Everything we needed for the beach. Such a short walk to the beach. It was great to have the elevator for my parents who are elderly and it was nice to use when taking loads of stuff up and down the stairs.
Stayed 5 nights in May 2024

10/10 Excellent

Taylor M.

Liked: Cleanliness, check-in, communication, location

Recent stay

We had 9 girls stay and it was a weekend for the books. Location is amazing, Dan has everything you need for the beach. Took a walk into the village every morning for coffee. The rooms were clean and had everything we needed. Definitely will recommend to anyone!
Stayed 3 nights in May 2023

10/10 Excellent

Yissel F.

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

Stay

Beautiful place! The beach is a dream!
Stayed 7 nights in Jul 2022

10/10 Excellent

Autumn S., Indianapolis, IN

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

Spring Break

We hosted Spring Break for our daughter and several of her friends. We loved this location. We were in the middle of everything—the walk to the village was so easy, we were only steps to the beach, and the place was clean and spacious. We will definitely be back!
Stayed 6 nights in Mar 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Leigh V.

Great

This beautiful beach home had it all for 6 of us—beach chairs, umbrellas, bikes, cooler, swimming pool, beach towels, and even an elevator! Very clean, beautifully decorated, comfortable beds, and a kitchen that was well stocked with dishes and cookware to cook, and eat in if you want but it's located close enough to walk to the village for live music and great food and drinks! Located in a quiet neighborhood across the street from the beach! This place is going to rent out quickly—don't miss a chance to enjoy it for yourself!

10/10 Excellent

Jandie S.

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

Awesome! So family friendly!

This property was so perfect for our beach vacation! They had everything and more we needed for the beach. It was so easy to check and and checkout. We will definitely stay here again if we are back in Siesta Key!
Stayed 4 nights in Jul 2023

10/10 Excellent

Rita S.

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

Best vacay ever

My friends and I enjoyed this trip so much! Dan was amazing to work with and very responsive. The house was great and had everything we needed.
Stayed 3 nights in Jun 2023

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