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

Siesta Key, Florida
$366 avg/night Minimum Stay 2 Nights
Bed 2

Bed

Bath 1

Bath

Home Apartment

Property Type

Sleep 6

Max Sleeps

Night 2 nights

Min Stay

The Coral Cabanas Poor-Boy
Just 8-steps to path of Siesta Key Beach, the world's best beach! 4-minute walk to bars, entertainment, shopping, dining and live music in the South Village! 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, see if it's a fit for you, and book a Siesta Key vacation rental getaway today!

What Guests Love
∙ Beaches – 12-step walk to Siesta Key's 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, this listing is direct at the guaranteed lowest cost
∙ 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 Siesta Key's best sunsets and whatever comes next
∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch
∙ The Fun - 4-min walk to the South Village and 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 Siesta Key vacation rental 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 Siesta Key-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, snorkel equipment, and umbrellas. There are also a few paddle boards available on a first come first serve basis and any other gear can be found 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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Energy-saving Switches
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi, With Speed Of 100+ Mbps (good For 1–2 People Or Up To 6 Devices)
  • OUTDOORS

    Barbecue Grill Patio
  • BATHROOMS

    1 Bathroom Bathtub Or Shower Hair Dryer Towels Provided
  • WORKSPACES

    Desk Desk Chair Office
  • LANGS SPOKEN

    English French
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Fitness Center Golf Privileges Golfing On Site Marina Nearby Paddleboard On Site Parasailing Nearby Scuba Diving Nearby Surfing/body Boarding Nearby Swimming Nearby Theme Parks Nearby Water Park Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village In The City Center Near A Hospital Near A Zoo Near Outlet Shopping Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Joe-La D.

    Submitted Aug 23, 2025

    Stayed Aug 18, 2025

    I really liked the spot it was super close to the beach. It was a very simple little place but that's all you need for a beach vacation. laundry was free. Lots of stuff to borrow and use. My ONLY complaint is the mattresses. Very firm and unforgiving. My back ached by the end of the stay. If they changed that out—I'd spend lots of weekends here. Note: it is on the south end of Siesta so you have to drive to the village shops and such but for a relaxing quiet spot—it's perfect.

  • julie w.

    Submitted Jul 21, 2025

    Stayed Jul 13, 2025

    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.

  • Parminder B.

    Submitted Jul 17, 2025

    Stayed Jul 8, 2025

    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 ?

  • Rachelle B.

    Submitted Jun 25, 2025

    Stayed Jun 20, 2025

    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.

  • Erica A.

    Submitted Jun 16, 2025

    Stayed Jun 9, 2025

    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.

  • Christine B.

    Submitted Apr 1, 2025

    Stayed Mar 28, 2025

    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!

  • Jon B.

    Submitted Mar 29, 2025

    Stayed Mar 24, 2025

    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.

  • billymac70us

    Submitted Jan 10, 2025

    Stayed Jan 2, 2025

    We really enjoyed our time at the The Poor Boy at point of rocks. The location was great, just at the southern end of crescent beach and walking distance to great restaurants. There was plenty of beach gear to use and picnic area was very quant. Dan, couldn't have been more helpful, he had recommendations on where to eat and some fun places to go. He was also extremely responsive to our request. We had a minor issue with the door lock and he had someone out right away to fix it. Only issue is the beds were a little too firm.

  • Larry and Daniel....

    Submitted Dec 27, 2024

    Stayed Dec 24, 2024

    Efficient and friendly staff. Nice place! Loved the walk to the beach.

  • Shaun A.

    Submitted Jul 18, 2023

    Stayed Jul 9, 2023

    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.

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Total

Includes taxes and fees
$366+
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