Entire apartment

Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Low Price

Apartment with a water park, steps from Crescent Beach

Photo gallery for Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Low Price

Beach nearby
Dining
Outdoor dining
Property grounds
Fridge, microwave, oven, stovetop
Escape to Coral Cabanas, where tropical charm meets secluded simplicity. Just eight steps from the best beach on Siesta Key, indulge in hammocks and alfresco lounging on the westerly sundeck. With snorkeling gear and locks for your paddle-board or kayak nearby at Point of Rocks Reef.

Reviews

9.6 out of 10
Exceptional

Entire apartment

2 bedrooms1 bathroomSleeps 8

Popular amenities

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

Add dates for prices

About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Low Price

The Coral Cabanas Poor-Boy
Just 8-steps to path of world's best beach! 4-minute walk to bars, entertainment, shopping, dining and live music! Communal lounging, private patio, alfresco dining, snorkeling, sunsets, and hammocks. This is a budget, two bedroom priced like our one bedroom units. Read the description below to see if it's a fit for you! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta

What Guests Love
∙ Beaches – 12-step walk to award winning beaches, calm shallow and clear
∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deck
∙ The Price – this is a budget 2BR priced like our 1BR units
∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deck
∙ Private Patio – this is the only unit on the property with a private patio
∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear provided
∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 miles
∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min away
∙ Sunsets –walk 30-seconds to best sunsets and whatever comes next
∙ 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 – access Siesta Key's top attractions and beaches guaranteed fun for all

Property Truths
This is a budget 2BR accommodation priced like our 1BR units. It has everything our prime units have except sound insulation in the ceiling which, although usually not an issue, might result in noise from above. If you want to experience Siesta Key, less than one minute walk from the best beach on the island but are on a budget and are not sensitive to noise from the ceiling above then the poor boy should be the perfect place for you.

The Beach
Skip the crowds and commercial feel. Coral Cabanas offers Key West-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.

The Location
No car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax? Sunbathe on the balcony, nap in a hammock, or enjoy Siesta's top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.

Reef Snorkeling
Siesta Key is already paradise—now add one of the Gulf Coast's best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.

Bedroom Details
This property is two stories and this unit is one flight up with no one above it or below it. There is a king bedroom, a queen bedroom and a sleeper sofa. You can sleep up to 7 family style. Need more space? We can get you an additional unit nearby.

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 amenities

Beach

  • Beach nearby

Ski

  • Snowboarding nearby

Internet

  • Available in the apartment: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city centre
  • Near a hospital
  • Near a zoo
  • Near an outlet shopping centre
  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Golf
  • Gym
  • Optional golf privileges
  • Paddleboard
  • Water park
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Theme park nearby
  • Wildlife walks 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)

General

  • Energy-saving switches in guestrooms

Similar properties

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in and check-out are 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

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

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
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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

Property is also known as

758687

About the area

Map
Siesta Key, FL

What's nearby

  • Crescent Beach - 3 min walk - 0.3 km
  • Siesta Key Marina - 8 min walk - 0.7 km
  • Siesta Key Beach - 15 min walk - 1.3 km
  • Turtle Beach - 4 min drive - 3.8 km
  • Lido Beach - 22 min drive - 18.2 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Hooters - ‬4 min drive
  • ‪Captain Curt's Crab & Oyster Bar - ‬11 min walk
  • ‪Lenny’z Pizza - ‬8 min walk
  • ‪Gecko’s - ‬3 min drive

Frequently asked questions

Is Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Low Price pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Low Price?

Check-in begins at 3:00 PM.

What time is check-out at Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Low Price?

Checkout is at 10:00 AM.

Where is Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Low Price located?

Located in the heart of Siesta Key, this apartment building is within 1 mi (2 km) of Crescent Beach and Siesta Key Beach. Point of Rocks and Siesta Key Marina are also within 15 minutes.

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Reviews

Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Low Price Reviews

9.6

Exceptional

9.0

Cleanliness

10

Location
Rating 10 - Excellent. 58 out of 69 reviews
Rating 8 - Good. 7 out of 69 reviews
Rating 6 - Okay. 3 out of 69 reviews
Rating 4 - Poor. 1 out of 69 reviews
Rating 2 - Terrible. 0 out of 69 reviews

Reviews

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

10/10 Excellent

Parminder B.

Amazing time

We had great time place was amazing quite clean. Definitely would come again. Had question when we got there Dan was amazing called me right way. Best way to celebrate my daughter's sweet sixteen 💖

10/10 Excellent

Joyce L.

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

Beautiful - great location

Beautiful area to visit. Convenient location for some beach time
Stayed 4 nights in Feb 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Mary H.

Great beach trip

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: Love the location.

10/10 Excellent

Susel R.

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

Excellent

It was fantastic.
Stayed 4 nights in Jun 2022

10/10 Excellent

Cathy Paulette W.

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

BEACHES!!!!!

What a beautiful place to vacation. The property was everything and more than expected. So close to the beach and town. Would fully recommend this property to anyone, nothing to fancy buy just what we needed for four 18 year olds and a grandma. Went to several beaches and really enjoyed the dog beach in Vinice.
Stayed 4 nights in Jan 2022

10/10 Excellent

Toni M.

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

FANTASTIC PROPERTY

This property is exactly as described. Great proximity to the beach. Property exactly as described. Great response from property manager. Would stay again and again!
Stayed 3 nights in Sep 2021
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Jill K.

Gorgeous!

We loved Siesta Key Poor Boy! Very quiet and nice neighborhood so close to beach access. The owner Daniel and Gertrude Rentals was so easy to work with and plan on going back next week to try another of the units in Old Man and The Sea. Looking forward to many years of visiting this property!

6/10 Okay

Freda Y.

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Vacation2021

there was only one bathroom which was hardly enough for a house that sleeps 8 people. The property manager was always friendly and helpful which I really appreciated. It's a nice and quiet area but still close to the beach.
Stayed 8 nights in Dec 2021
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Michelle S.

Great value for the price

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: Property was clean and everything was as described. Owner is very responsive and helpful. Property is located within walking distance of many stores and restaurants.

8/10 Good

Andrew B.

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Super Cool Location But a Little Lacking.

90 second walk to the ocean. 5 minute walk to restaurants and bars. The place was a bit dingy and, if you’re on the first floor, you’ll definitely hear the people above you. Great common area with a grill and a couple tables.
Stayed 2 nights in Mar 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Chris W.

Great location!

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: Location for this rental was great! Right across from the beach and within walking distance of restaurants, bars, and grocery. There is a bike rental place nearby and it was just a short bike ride to the other beaches and got to explore the rest of the island. Great place to escape and unwind!

10/10 Excellent

Amanda E.

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

perfect location

Our stay at the Poorboy was great. It's cozy and simple, but we were comfortable and had everything we needed. If you want to be close to the beautiful soft white sand beach, this is it! We were able to cook in house if we wanted, but were close enough to great seafood and restaurants. The community is quiet and friendly. We are from a small quiet town in Nebraska, though the atmosphere was night and day from that, we could walk wherever we needed to go and felt safe. We had a question when we got there and Daniel answered on the first ring. Would definitely stay again!
Stayed 3 nights in Jan 2020
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Ryan H.

Great Location!!

Great location to the beach. We have 3 children and it was nice to be able to walk to the beach and come back and take a nap and then go back to the beach! All the beach stuff was right there. We just grabbed chairs an umbrella and some sand toys and headed to the beach! There is a common area which was great to eat, relax and be outside in the nice weather. My husband used the propane grill every day! The location & space was perfect for our family. The Hook Family
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kim G.

Poor Boy on Siesta Key

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: The description of this property is spot-on; you know exactly what you’re getting and where you will be. It is not a glamorous place, but it sleeps a lot of people and feels homey. The kitchen has everything you need, even coffee filters and extra laundry detergent. Daniel was super quick to reply and great communication-I would definitely recommend this place for a budget vacation in a very desirable location. The location cannot be beat-it’s close to everything and the beach is just steps away.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

julie w.

Poor Boy

We have stayed at the Poor Boy a few times. We will always come back! The rooms are clean, all the things needed for a beach trip is provided. The customer service and good communication is a bonus.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Rachelle B.

Great

We had a wonderful time. The appartement was just what we needed. It was close to the beach and we took advantage of using the accessible beach chairs. After our stay, my niece left her sandals and the staff was kind enough to ship them to my house. What a service! We will gladly recommend to our friends and look forward to returning there.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Erica A.

Amazing Stay

We LOVED our stay at Siesta Keys! The room was exactly as described and in a perfect location. This spot was very family friendly and less crowded than other locations. The access to the beach was amazing and the free transportation stop was a short walk away.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Christine B.

Amazing location

The Poor Boy was in a perfect location right next to the public beach access. It was a quick walk to the downtown area. The kitchen had all the amenities needed and then some. There was plenty of space and a nice outdoor sitting area! Would definitely stay here again!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jon B.

Very close and reasonable stay

Host was very prompt with responses. As close as you can get without being right on the beach. Walk way to the water right outside your door. As owner described ceiling to master is right under kitchen/ living room of upper. Can be noisy pending occupants above this Po boy unit. Just bring a set of ear plugs in case and you should be just fine. Wasn't that big of deal and calmed down after 10 pm. Close walking distance to some fantastic restaurants and shopping spots. Would definitely come back in the future.

10/10 Excellent

Shaun A.

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

Superb stay!

The room was just as described. Very comfortable, you can feel at home here. My wife and I, along with my 82 y/o mother, and two of our grandsons, 9 & 12 had a great stay. Rooms were clean and beds were comfortable. Beach access is across the street, then just a short walk to the beach. We brought along groceries to cook while there. There was a grill outside, hammocks, and nice outdoor setup. I hope to go back for another visit.
Stayed 3 nights in Jul 2023

10/10 Excellent

Suzanne T.

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

Wedding stay

We had a wonderful time with our kids at your property. The area was so nice to entertain the other family members that came as well. It made it an easy choice whose place to hang out at! :) It was so close to beach also! Would stay again! Thank you!
Stayed 8 nights in Sep 2022

10/10 Excellent

julie w.

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

Perfect for us!!

This is the second time we stayed at the Poor Boy. We love it. We met friends in Siesta Key and we all met at the Poor Boy. The outside area is so welcoming with the outside grill and Tiki bar. There is plenty of areas to be outside after a long day at the beach. We walked down and had coffee every morning at the beach.The Poor Boy has everything you need! We will be back!!
Stayed 7 nights in Jun 2023

8/10 Good

Elliott E.

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

Poor Boy

It gets the job done and has plenty of parking.
Stayed 5 nights in Mar 2023

10/10 Excellent

Kylie H.

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

Great location

Dan was incredible to work with and was great at communicating in a timely manner! Everything you could possibly need for your stay is available to use both in your lodging area and the community areas as well. The location was perfect! Steps away from the silky smooth sandy path to the beach and a short walk to restaurants, shops, etc. The outdoor community garden area was beautiful and perfect for relaxing or eating a meal! All five of us enjoyed our stay, there was plenty of room for us to sleep and hangout! Would definitely recommend any of the lodging options, Dan made the check in seamless. You won’t regret staying here!
Stayed 3 nights in Jan 2023

10/10 Excellent

Doug L.

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

Relaxing Stay

The place is just as advertised. It is an older unit but well kept, giving it an old Florida feeling that you loose with new places. I would recommend putting a copy of the old man and the sea on the coffee table. The location could not have been better. It is just across the street from public access 13 to the beach. The unit is well equipped for a comfortable stay. Having the laundry outside the door was actually a positive and not a hinderance. The common areas expanded the useable space with a great cooking grill. The patio gave the place a nice outdoor seating area as well.
Stayed 6 nights in Dec 2022