Pirate-themed waterfront estate with heated private pool, new boat dock, and two six-seat golf carts — 5BR/4BA sleeping 10.
The Gilded Compass mixes swashbuckling interiors with modern comfort, plus kayaks and paddleboards for the whole crew. Pets welcome on this Intracoastal adventure home.
🛺 Golf cart, Allows pets, Internet, Heated Pool, Oceanfront, Near Ocean, Ocean View, Water View, Waterfront, Bay View, Pool View, Beach, Shared beach access, Air Conditioning, Kitchen, Free Parking, Smart TV
Our promise
Lower prices when you book direct — no OTA markups.
Direct line to our local team at (727) 308-6726.
Not just a transaction — we host like neighbors.
Things to know
House rules
Check-in after 4:00 PM · Checkout before 10:00 AM · Pets allowed · No parties or events
Safety & property
Smoke detector · Carbon monoxide detector · Exterior security cameras · Heated pool · Waterfront dock
Cancellation
Flexible cancel window shown at checkout in the booking widget. Questions? Call (727) 308-6726.
The Pirate House is “freaking insane!”! We had such a good time at Tom’s place. We had a group of 10 dudes on a bachelor party and we throughly enjoyed ourselves and the fun setting of the house. Tom was super responsive with anything and highly recommend chartering through him! We charters a booze cruise for our group and Capt George picked us up promptly right out the back door. Highly recommend for anyone with a big crew looking to party like Pirates!
★★★★★Airbnb - 2026-09-16
From the very first day we finalized our booking, Tom was communicating with me and providing information. The amount of detailed information he provides before and during the stay were above and beyond any rental experience I have had. The home was amazing and getting to meet Tom and his wife was very enjoyable. They love what they do and are incredible hosts! The home has everything you need to make your stay relaxing and the decorations have you finding new and interesting touches throughout your stay. We also enjoyed being able to use the golf carts to grab lunch and go to the beach. Can’t wait to return to IRB and will definitely be contacting Tom to assist in finding us the next home for our stay!
★★★★★Airbnb - 2026-09-06
This was the perfect place for our annual friends trip. We had everything we needed to cook and plenty of space inside and out. The pool and outdoor area are perfect and we even docked a boat out back. We’ll definitely be back.
★★★★★Airbnb - 2026-09-05
The BEST freaking airbnb i’ve ever stayed at in my LIFE! The theming, the decor, the host Tom- everything was absolutely 10/10 incredible. I can’t recommend this home enough. Tom, thank you for giving us all such a special and memorable trip. Tom is super awesome and friendly- very responsive, very informative. BEST AIRBNB WEEKEND EVER! Yo Ho, Ya Mateys!! ⚓🏴☠️
★★★★★Airbnb - 2026-08-16
We had a fabulous time at the Gilded Compass. My kids were enthralled with the house from the moment we walked in. It was so easy to kayak and paddle board right off the dock. Tom was great! At one point my son said he wanted to fish and within an hour we had fishing poles!!! We will be back!
★★★★★Airbnb - 2026-08-15
Excellent stay! The house is incredible; the pirate theme makes it an amazing stay! We never left the property; it felt like a private resort.
★★★★★Airbnb - 2026-08-07
The house was charming and our daughters had so much fun dressing up as pirates with the gear provided. The house was clean, very well furnished and Tom was a great host and super helpful and available at all times. We did have some flooding with crazy rain storms in the dining area but it seems Tom is addressing that to avoid it in the future. I do advise that you bring a couple kitchen items if you plan to cook a lot as there wasn’t more than a single large pot and the stove/oven combo could use an upgrade as it is a pretty beat up electric that takes a long time to heat up. Tom probably would a be provided anything needed for kitchen we just didn’t want to bother him with it. Great stay, great host overall.
★★★★★Airbnb - 2026-07-24
We had an amazing stay. The place was exactly as described and perfect for families. Tom was so responsive and definitely one of our best rentals ever. We loved the whole area.
★★★★★Airbnb - 2026-07-19
We have such a wonderful stay at Ton’s pirate house!! It was so perfect with the kids! The scavenger hunt was so fun too! We had a great time fishing and enjoying the pool! Would absolutely recommend and stay again!
★★★★★Airbnb - 2026-07-14
Our family of 9 enjoyed the space! It is laid out perfectly for multiple people to stay. The decor and the amenities were beyond expectations. So many little surprises to make the experience. Tom provided lots of helpful information for restaurants and experiences to make our trip memorable. We will definitely be back. Thank you Tom for the wonderful memories.
★★★★★Airbnb - 2026-06-26
Prefect big house for family of 9. Pool was a big hit with all.
★★★★★Airbnb - 2026-06-15
We had a perfect vacation made possible by our stay! The house is super cool - with every possible pirate themed detail thought through so well! Most importantly it was comfortable, clean and had everything we needed. The kids loved the pool, the pirate themed dress up and decor, and the adorable touch of a treasure hunt when we arrived. It’s a beautiful location right on the water- we saw dolphins swimming around while standing on the dock! Our whole group loved the house and the great location close to the beach and restaurants. Tom was a super responsive host as well- thank you so much! We had a blast and would love to return again!
★★★★★Airbnb - 2026-06-11
The house was amazing! The location is perfect with close access to the beach and great access to the canals and the ocean for boating as well. Great and friendly hosts!
★★★★★Airbnb - 2026-06-11
The most amazing vacation! Tom was beyond fantastic and so fast to respond! The house was amazing! My family had a blast and we can’t wait to return! Tom’s friend, Captain George picked us up right at the dock and took us on a beautiful boat ride! We swam, fished, ate, drank and laughed all week! Thank you for providing us a place to make wonderful memories that we will always cherish!
★★★★★Airbnb - 2026-05-25
We had a great time with our family of ten. There were a few hiccups with leaks inside from a rainstorm but Tom was unaware and quickly responded. The Pirate decor was outstanding, you really felt like you were on vacation. It was nice to have golfcarts available as it was about .7 miles to the beach. The artwork inside was Amazing! The pool was great and we really enjoyed the dock, and use of the kayaks. We really appreciated having Beach towels supplied as well as other necessities in kitchen and baths, as well as pool area. We had so much fun trying on the pirate costumes and taking many family photos in them. The kids loved it.
★★★★★Airbnb - 2026-05-18
I hosted my mermaid themed bachelorette here and had the absolute best time! The house was perfectly themed with all the amenities. Tom was so kind to offer a boat charter off the dock which was just so easy to coordinate. Our captain even showed up dressed as a pirate. We loved the paddle boards and hanging out in the pool. Beds were super cozy and the differently themed rooms were just so fun. Cherry on top was the photographer Tom provided to capture us girls in our mermaid tails. Memories to last a lifetime and I’m just so grateful. Stellar host! Oh and it was super easy to take the golf carts to the beach across the street. I can’t recommend this place enough. It’s like your own personal Disney land. I hope we can come back and stay again. Great for families, friends, and anyone ready to get into the pirate spirit. Just simply magical. Thank you Tom for making my bachelorette and unforgettable adventure! 🧜♀️🙏🏽💍🫶🏽
★★★★★Airbnb - 2026-05-12
Excellent stay and the host was awesome. Having a fiance that works in interior design I really appreciated how well the space was done. Theres endless details and surprises at the house that will really make the stay feel "piratey." Great backyard with pretty much any amenity you need to have a fantastic time. Thanks for the great stay.
★★★★★Vrbo - 2026-05-04
Great location wonderful house so nicely decorated just perfect for our day for a wedding weekend with the big group!
★★★★★Airbnb - 2026-04-26
Staying at the Guilded Compass was perfect from start to finish. Each detail has been clearly thought of to make the stay as comfortable and fun as possible. The backyard is great for hanging out and enjoying the bay, the house is a short golf cart ride to the beach and location is ideal. The next time we vacation near Clearwater, we will surely try and stay at this house again. Overall I couldn’t recommend staying here enough!
★★★★★Airbnb - 2026-04-23
Tom was the ultimate host. We travel a lot; I scour air bnbs to be sure I’m finding the perfect place- this place was a gem. My family traveled with 4 adults, my 2 children, and my parents (my dad is handicapped- struggles significantly to get around). Tom communicated with me for weeks prior to our trip- answering all questions, making sure we had everything we needed for my father’s comfort. I have never met a more attentive host. Not only was this place accessible for my dad, the pirate theme was unlike anything I’ve ever seen. No detail was missed. The beds were amazing, black out curtains to easily sleep in, the two golf carts made it easy to get to the beach, the pool was heavenly, the view was beautiful. The kids had a blast with new treasures around every corner. The dress up was a hit! We chartered Toms boat one afternoon and he went out of his way to get my dad on. I could write a book on how amazing he and this place was, but do yourself a favor and find out for yourself ❤️
★★★★★Airbnb - 2026-03-30
Beautiful home, wonderful outdoor space. Everything was exactly as described. The most organized home I’ve ever stayed in with lots of instructions, suggestions, a welcome book, notes on the beds. Young kids would absolutely love the pirate theme!
★★★★★Airbnb - 2026-03-23
Excellent stay and would highly recommend. Great space with tons of seating options. very creative with the Pirate theme where they went all in. Heated pool was great on a cool day and the twin golf carts helped our group of 8. Thanks for a great trip.
★★★★★Airbnb - 2026-03-09
I rented this house for my annual girls weekend with 9 of my friends. The house is so much fun and the views are gorgeous! It’s such a fun place with so many hidden details. We used the golf carts everyday and it made it so convenient to get to the beach and the restaurants. Tom was a great host and always just a text away with any question we had. We didn’t want to leave!
★★★★★Airbnb - 2026-03-05
We had an amazing stay at this property and couldn’t have asked for a better experience. The house was exactly as advertised—if anything, it exceeded our expectations. The décor was authentic, fun, and created a great atmosphere for all ages in our group. We especially loved spending time outside enjoying the pool, grilling meals, and eating right on the water. Having access to the kayaks and paddleboards was a huge bonus and gave us plenty to do throughout the stay. There was never a dull moment. Another big plus was that every bedroom had its own bathroom, which made things very convenient for our group. The location was also fantastic. It’s tucked into a quiet neighborhood but still very close to everything you might want—great restaurants, bars, a convenience store, parks, and the beach. One of our favorite things was exploring the area by golf cart. It made getting around easy and added to the fun of the trip. Tom was also an excellent host. Absolutely recommend staying here.
★★★★★Airbnb - 2026-03-01
We had the absolute best stay at the Pirate House! From the moment we arrived, everything exceeded our expectations. The house was fully stocked with anything you could possibly need and it truly felt effortless settling in. One of the highlights was seeing dolphins multiple days right from the property. It never got old and made the whole experience feel magical. We also loved kayaking and spent so much time enjoying the heated pool. There was always something fun to do, but it was still incredibly relaxing. The kids were obsessed with the pirate costumes. They dressed up as a full pirate crew multiple times and took the best pictures out on the deck. It made the whole stay even more special and memorable for them. Tom was fantastic, very responsive, proactive with communication, and genuinely helpful throughout our stay. Everything felt smooth and stress free. I honestly couldn’t have asked for a better experience. We would absolutely stay here again and highly recommend it
★★★★★Airbnb - 2026-02-10
The pirate house was amazing!!! Our group of 10 had the best time. No idea where they found all of this cool pirate stuff. The backyard, 2 golf carts and being so close to the beach. What a great stay. Tom and Dena you are the best!!highly recommend Off the Charts. !!!!
★★★★★Airbnb - 2026-02-06
The house was great. The kids had a blast swimming in the pool, even in the cold they had a lot to do in the house. Golf carts were a bonus and we could split up when we wanted. I highly recommend.
★★★★★Airbnb - 2026-02-03
Booked this house for family who came to town to visit. Everything was excellent! The house is off the charts! Golf carts are awesome! Everyone raved about the decor and pirate theme. Tom & Dena were extremely responsive and easy to work with. Thanks again!