Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets!

Photo gallery for Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets!

A hotel with a covered outdoor area, palm trees, and a sign reading "Coconut Cove."
A courtyard with palm trees, lounge chairs, and a covered walkway.
A beach with clear skies, a few people in the water, and a grassy area with a beach umbrella.
A bar area with a thatched roof, a sign for 'LANDSHARK Lager', and a television screen displaying a sports event.
A vacation rental sign with contact information and a QR code.

Reviews

10 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • On-site fitness centre
    A rare find - enjoy convenient access to fitness facilities during your stay.
  • Discover nearby landmarks
    Walk to Siesta Key Beach

Popular amenities

  • Balcony
  • Barbecue grill
  • On-site fitness centre
  • Air-conditioning
  • Pet-friendly
  • Refrigerator

Explore the area

View in a map
Siesta Key, FL
  • Place, Crescent Beach
    ‪3 min walk‬
  • Place, Safe Harbor Siesta Key
    ‪9 min walk‬
  • Place, Siesta Key Beach
    ‪17 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪30 min drive‬

Rooms & beds

8 bedrooms (sleeps 24)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

Bedroom 5

1 King Bed

Bedroom 6

1 Queen Bed

Bedroom 7

2 Single Beds

Bedroom 8

2 Single Beds

Common Space

1 Double Sofa Bed

5 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Spaces

Porch or lanai
Kitchen
Balcony
Dining area

Add dates for prices

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About the area

Siesta Key

Located in Siesta Key, this apartment 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 Science Education Aquarium and St. Boniface Episcopal Church Labyrinth are also worth visiting. Discover the area's water adventures with scuba diving and snorkelling nearby, or enjoy the great outdoors with cycling and ecotours.
View more Apartments in Siesta KeyOpens in a new window
Map
Siesta Key, FL

What's nearby

  • Crescent Beach - 3 min walk - 0.3 km
  • Safe Harbor Siesta Key - 9 min walk - 0.8 km
  • Siesta Key Beach - 17 min walk - 1.5 km
  • Turtle Beach - 4 min drive - 3.8 km
  • Lido Beach - 26 min drive - 17.8 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Panera Bread - ‬4 min drive
  • ‪Five Guys - ‬4 min drive
  • ‪Culver's - ‬5 min drive
  • ‪Captain Curt's Crab & Oyster Bar - ‬11 min walk

Frequently asked questions

Is Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets! pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets!?

On-site parking is available at the property.

What time is check-in at Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets!?

Check-in begins at 3:00 PM.

What time is check-out at Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets!?

Checkout is at 10:00 AM.

Where is Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets! located?

Situated by the sea, this apartment building is within 1 mi (2 km) of Crescent Beach and Siesta Key Beach. Point of Rocks and Safe Harbor Siesta Key are also within 15 minutes.

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. 17 out of 18 reviews
Rating 8 - Good. 1 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Family thanksgiving

We had a great stay here!
Stayed 4 nights in Nov 2024
Response from VrboOwner on 20 Dec 2024
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We rented out the entire house for a destination wedding. We could comfortably sleep about 30 people, which is just what we needed. We hosted all of our wedding guests and we held the wedding ceremony in the front garden of the house. It was perfect. The downstairs open patio was an ideal place to serve buffet-style meals and for everyone to hang out in the evening hours. Every night we walked the very short path to the beach and witnessed the most beautiful sunsets. The house has everything you would need to enjoy a beach day (wagons, snorkel gear, paddleboards, umbrellas and chairs). Beach towels are provided too! We loved the secluded location of the house. It's right on a part of the beach that doesn't get too crowded. The friendly Gertrude Rentals team was available to help out with any questions or needs we had during our stay.
Stayed 4 nights in Aug 2026
From a partner site

10/10 Excellent

Location and convience!

We thoroughly enjoyed our stay at Crescent Beach Siesta! We loved being so close to the beach (amazing sand and clear water!) and the cute beachy neighborhood. The units were perfect for our family - spacious, clean, and comfortable. We will be back and highly recommend!
Verified review

10/10 Excellent

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

The ideal family reunion spot

We had folks fly in from all over the country and this amazing property had room for everyone, several great communal hang spots, and everything we needed to have a hassle-free stay just steps from a gorgeous beach. We hope to be back!
Stayed 4 nights in Aug 2023
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Verified review

10/10 Excellent

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

Best vacation

We had the best time here for a 3 night stay. Perfect location for the beach! The units were clean and was stocked well. The amenities were great. Highly recommend this place to all my family and friends!
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay was amazing! We had a group of 19, and we loved having multiple units for some privacy and fantastic common areas to gather and relax. Our teenagers really enjoyed using the paddle boards and snorkeling gear. Everything was clean and comfortable. It was absolutely the most perfect place for our team to stay for a long weekend. Dan was so responsive and helpful. The best VRBO experience!
Stayed 3 nights in Nov 2025
Response from VrboOwner on 22 Dec 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones
Verified review

10/10 Excellent

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

Awesome

Awesome rental. Management was very nice and helpful. Most definitely will rent again.
Stayed 7 nights in Jul 2023
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Verified review

8/10 Good

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

Great Place for Friends Trip

The property was in a great location and had plenty of room for 22 of us. About a 3-4 minute walk from the beach as the beach access is right across the street from the main entrance. If you're looking for somewhere elegant or luxurious this probably isn't the place for you, but nonetheless it was a good property to spend a long weekend going to the beach.
Stayed 3 nights in Sep 2021
Response from VrboOwner on 7 Sept 2023
Thank you Luke.
Verified review

10/10 Excellent

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

Wonderful location

We had a wonderful experience at Old Man and The Sea!! Our family and friends rented the entire property for a senior trip for our boys. The property was clean and the location was phenomenal!! Communication for questions and comments was answered in a timely manner and Dan and Matt were very helpful! We would rent this property again.
Stayed 7 nights in Jul 2021
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Verified review

10/10 Excellent

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

Great spot for large group

Rented the whole Inn for a large group. Lots of beds. The outdoor dining space was great for gathering. Ample cooking space within the units and small appliances needed to cook and serve were available which was nice. Everything was clean upon arrive. Great access to the beach and beach chairs were very nice to have.
Stayed 5 nights in Dec 2021
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Verified review

10/10 Excellent

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

Classic Florida

This place is very cool and convenient to the beach. There are no ocean views but it’s an easy walk across the street. The house has everything you need. Owner was very helpful and answered our questions immediately.
Stayed 4 nights in Oct 2021
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Verified review

10/10 Excellent

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

Family reunion

The old man and the sea was great for a family reunion. We had 25 family members who came through across the week - 5 different families and we fit nicely in the Inn. The beach was very close and is beautiful. Checking in was easy except we didn’t receive the combinations to the rooms until the day we arrived. It would have been better to have emphasized that fact early on. All in all it was a wonderful reunion thanks to the place we stayed
Stayed 6 nights in Jun 2021
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
From a partner site

10/10 Excellent

Great for family gathering

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We rented the entire property (4 upstairs units and 1 on the ground floor) for a 90th birthday family gathering. It was perfect for our party which consisted of ten adults and one child. The outside area is terrific and the beach access, as advertised, is some 50 yards from the property. Swaths of the beach are private but there was a shaded area to the south as you enter that we were able to use and the Inn comes with beach chairs, umbrellas, etc. it really proved to be the perfect place for our purposes.
Stayed 3 nights in Mar 2022
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
From a partner site

10/10 Excellent

Great place forlarge groups

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My family rented out the entire property for several days. It fit us perfectly and with having the separate units, gave us a space to retreat and have a separate space for each family. I love my nieces and nephews, but there are a lot of them so some "private" space is nice, The eating area was great and we brought some extra tables and chairs for our large group. It is nice to be able to eat all together. And the grills provided were excellent for large groups. Will definitely keep this property on our family's radar for future stays. Thank you!
From a partner site

10/10 Excellent

Wonderful Trip

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great stay. Fantastic location.Two quick suggestions: 1. My Mom stayed in the Poor Boy & due to its proximity to the laundry room, her room had quite a few mosquitoes in it. They seem to swarm in the laundry room. 2. All the provided umbrellas have a pointed bottom at the base & what is really needed are the augur or corkscrew-type bottoms to better secure the umbrella bases.Thank you.
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Verified review

10/10 Excellent

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

Perfect Family Reunion spot!

Perfect fit for our group!! We rented all 5 units to accommodate group of 22. Having the entire place allowed us to take full advantage and enjoy all the areas for breakfast to late night gatherings. The owner & management team were incredibly responsive to requests. Tons of toys to use on-site and at the beach... we used the kayaks, the lawn games, the bicycles etc. There are plenty of chairs and umbrellas and towels. You really can show up and relax! We catered group dinners & cooked a full on BBQ on the two large propane grills. A person in our party was able to visit the location ahead of our visit so we knew exactly what the place looked like and it matches the pictures. Rooms are comfortable and had everything we needed. We'll stay here again or visit another of the owner's property for our next family reunion.
Stayed 3 nights in Jul 2022
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
From a partner site

10/10 Excellent

A perfect big group vacation/birthday celebration place to stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had the best time at this rental. We rented the whole place for my husbands 50th. The outdoor conversation areas were even better in person. It exceeded my expectations the units all having their own little living space made it so nice. People could wake up at their own pace come too with out anyone knowing or caring. The place was well stocked with all the beach supplies needed! The beach was beautiful. The sunsets out of this world!!! 22 people 18 were couples. We had beds to spare but I think we maxed out on couples. More singles could have stayed no problem. We didn't even use all the sofa beds. The lights outside made it magical at night for us to all hang out. We all can't wait to come back and we will! My only think I would mention were the beds could be upgraded. That said it wasn't something that would keep me from coming back
Stayed 4 nights in Dec 2021
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
From a partner site

10/10 Excellent

Had a great time.

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We came down with 22 High School seniors along with 8 parents. We had plenty of room for everyone along with room for entertainment. The location was excellent, close to shopping and the beach for the kids. I would recommend this to anyone going to the Sarasota area.
Response from VrboOwner on 7 Sept 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
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