Experience the epitome of luxury at AJ Vacations on Lido Key, where a private elevator, rooftop deck and multiple balconies offer breathtaking views of the beach and Gulf of Mexico. With 5 spacious bedrooms, each with its own en-suite bath, this vacation home comfortably accommodates up to 16 guests. Enjoy Smart TVs and free Wi-Fi throughout your stay.
Reviews
1010 out of 10
Exceptional
Entire home
5 bedrooms5 bathroomsSleeps 16623 sq m
Popular amenities
Kitchen
Washing machine
Dryer
Free Wi-Fi
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block.
Let's get straight to the point: THERE IS NO FINER RENTAL HOME on Lido Key! From the exquisite residence to its extensive list of amenities, prime location, and exceptional customer service, your quest for the perfect vacation rental ends here! Nestled in the heart of St. Armand's on Lido Key, mere steps away from the world-renowned Lido Key Beach and the vibrant entertainment district of St. Armand's Circle, you'll have instant access to a plethora of shops, restaurants, dessert parlors, bars, and more. Plus, it's just a short 2-mile jaunt to Downtown Sarasota, offering even more entertainment options.
If your ideal vacation involves taking in stunning views of the beach, the Gulf of Mexico, Sarasota Bay, St. Armand's Circle, and Downtown Sarasota, you're in for a treat. Multiple balconies and a rooftop deck adorn this spectacular home, providing ample opportunities to soak in the breathtaking surroundings. With approximately 5,150 square feet of interior living space and over 3,000 square feet of covered patios, balconies, a rooftop deck, hot tub, and entertainment space, your senses are in for a remarkable journey.
Stepping inside, you'll be immediately greeted by an elevator providing access to all floors, soaring vaulted ceilings, a sense of spaciousness that will delight, and the undeniable craftsmanship that defines this home. With 5 bedrooms, each boasting its own private en suite bath (for a total of 5.5 baths), this home comfortably accommodates up to 16 guests. The excitement continues on the ground level, where you'll discover a club room with ample seating, a TV, and an arcade/game room featuring a pool table, Skee-Ball, shuffleboard, hoops arcade basketball, ping pong, and a selection of games. This luxury vacation rental is equipped with Smart TVs and free Wi-Fi throughout, ensuring that entertainment and connectivity are always at your fingertips.
And speaking of paradise, let's dive into what each level of this magnificent abode has to offer:
**Ground Level:**
Get ready to make a splash! The Pool has arrived, featuring the biggest slide on Lido Key, the largest grotto hot tub, the biggest pool, and a large fountain splash pad for kids—all right on the beach! Plus, enjoy a sand pit for kids, fun activities, and putting greens. Dive in and experience the ultimate beachside fun for the whole family!
The ground level is your gateway to outdoor parking for up to 6 vehicles in the driveway. This level also showcases a convertible game room that effortlessly transitions from indoor comfort to outdoor living through the home's covered structure. The main entryway boasts a welcoming foyer, complete with an elevator and stair access to the primary living level above.
**(2nd Floor) The First Level of Living:**
As you ascend to the second floor, the grandeur of this home truly unfolds. The main great room takes center stage, featuring a magnificent kitchen that can comfortably host up to 10 delighted guests. Adjacent to the kitchen, a bar with seating for 6 and a charming round table for 4 set the scene for unforgettable dining experiences.
But the excitement doesn't stop there. The living room, furnished with a Smart TV and an abundance of inviting seating, invites you to unwind and revel in entertainment, all while basking in the captivating ocean view. Beyond the living room, step onto the oversized balcony—an extension of the great room and kitchen. It's a sprawling outdoor oasis, lavishly adorned with seating for your comfort and room for an additional 8 guests for al fresco dining. Here, the view is nothing short of enchanting, a picturesque panorama of powdery sands and the boundless, breathtaking ocean. It's a slice of paradise awaiting your presence, where every moment becomes an invitation to savor.
On this floor, the adventure continues with two vibrant bedrooms:
- Bedroom Ensuite 1 allows you to step onto the balcony, grab a seat for four, and immerse yourself in the invigorating morning Gulf view. This room also boasts a spacious walk-in closet and a luxurious en-suite bathroom.
- Bedroom 2 adds a playful twist with bunk beds for six, a cozy seating nook that teases you with glimpses of the Gulf, a capacious walk-in closet, and its own en-suite bath.
**(3rd Floor) The Second Level of Living:**
As you ascend to the third floor, prepare to be enchanted by a world of luxury and sweeping vistas. Here, you'll find the Master Suite, Bedroom 3, a sanctuary like no other. This magnificent suite opens up to a wrap-around balcony, treating you to breathtaking 180+ degree water views. It's furnished with a King Bed for regal comfort, and for those seeking a touch of indulgence, there's a Twin Day Bed for additional guests.
But that's not all. A cleverly designed nook/kitchenette adds a dash of convenience
, featuring an Espresso Machine, small fridge, and a wet bar for your refreshment needs.
As you explore further, Bedroom 4 unveils itself, boasting a King Bed and expansive Gulf views that stretch as far as the eye can see. A Walk-in Closet and a luxurious en-suite bathroom complete this haven of comfort and style.
Meanwhile, Bedroom 5 adds a playful twist with bunk beds—featuring a queen bottom bunk and a twin top bunk—for cozy nights of slumber. This bedroom also boasts an en-suite bath and offers picturesque views of the city below.
This level is a haven of opulence, where each room tells a unique story of comfort, style, and the boundless beauty that surrounds you. It's a living experience that transcends expectations, and it's yours to savor.
Elite Linen Experience:
Rest assured, our linens are expertly laundered at a premium commercial facility, ensuring a superior experience during your stay in this exclusive vacation rental.
And that's not all! Your reservation also comes with a delightful array of complimentary amenities, including bikes, beach chairs, beach towels, a beach wagon, a beach cooler, and more, ensuring that your vacation is as convenient and enjoyable as possible.
Parking Information:
Convenient outdoor parking is available for up to six cars in the driveway at no extra cost. Please keep in mind that temporary street parking is limited to a maximum of one hour, in full compliance with the City of Sarasota's regulations. Furthermore, pay-to-park designated spots are conveniently positioned along the street, continuing all the way up to St. Armands Circle.
certificate number 25-VR-000052
Property amenities
Beach
On the beach
Beach loungers
Beach towels
Pool/Spa
Heated pool
Hot tub
Outdoor pool
Private pool
Internet
Available in the house: Free WiFi
Parking and transport
Onsite parking options include a garage
Kitchen
Blender
Coffee grinder
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Ice maker
Kitchen island
Kitchenette
Microwave
Oven
Paper towels
Refrigerator
Toaster
Dining
Dining table
Bedrooms
5 bedrooms
Bedsheets provided
Sofa bed
Bathroom
5 bathrooms
Bathtub or shower
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Living room
Separate dining area
Entertainment
Games
Smart TV
Stereo
Video games
Outdoor areas
Balcony
Barbecue grill
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Work spaces
Desk
Desk chair
Comfort
Air conditioning
Heating
Pets
Service animals only (pets not allowed)
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Safe
Location highlights
In the city centre
Near a hospital
Near an outlet shopping centre
Near the bay
Near the marina
Near the ocean
On the waterfront
Things to do
Arcade/game room
Bicycles
Billiards/pool table
Foosball table
Heated pool
Table tennis
Basketball nearby
Cycling nearby
Fishing nearby
Golfing nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Parasailing nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Swimming nearby
Water skiing nearby
Water tubing nearby
Wildlife walks nearby
Windsurfing nearby
Safety features
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets not 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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
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
About the area
Located in Sarasota, this holiday home is in the city centre and on 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 Lido Beach and Longboat Key Beaches. Travelling with kids? Consider Mote Marine Laboratory & Aquarium, or check out an event or a game at Ed Smith Stadium. Discover the area's water adventures with jet skiing, kayaking and scuba diving nearby, or enjoy the great outdoors with cycling. Visit our Sarasota travel guide
Does Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block. have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
Is Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block. pet-friendly?
No, only service animals are welcome at the property.
How much is parking at Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block.?
On-site parking is available at the property.
What time is check-in at Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block.?
Check-in begins at 4:00 PM.
What time is check-out at Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block.?
Checkout is at 10:00 AM.
Where is Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block. located?
Located in Sarasota, this beachfront holiday home is in the city centre and within a 5-minute walk of Lido Beach and St. Armands Circle. South Lido Park and Sarasota BayWalk are also within 2 miles (3 km).
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Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block. Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Unbelievable house in the best location in St. Armands. If we vacation here again we will definitely check on availability to re-book. Check-in/out was seamless and the property manager was available throughout our stay when we had questions.
We had an incredible stay at this beautifully appointed home. The location couldn’t be better—just a short walk to the beach and minutes from St. Armands Circle. The house itself was luxurious, spacious, and spotless, with stunning views from every room. It was the perfect blend of comfort, style, and convenience. Highly recommend for a high-end Sarasota escape!
Our family of 16 spent Thanksgiving week at this beautiful beach house, and it was absolutely perfect for our group. The home was exactly as pictured—spacious, clean, and thoughtfully designed—and truly did not disappoint.The game room and pool area were huge highlights, giving everyone plenty to do and enjoy without ever feeling crowded. The location was ideal as well, just a short distance to St. Armands Circle, where we found great dining, shopping, and entertainment.The host was incredibly attentive throughout our stay, quick to respond and genuinely committed to making sure we had everything we needed.Overall, this house was everything we hoped for and more. We couldn’t have asked for a better place to celebrate Thanksgiving together, and we would absolutely stay here again!
Peaceful, plush and comfortable. The house is amazing with great views and amenities.Walking distance to the beach, shops, restaurants.Kids loved the pool more than the ocean.
This house was amazing, we had a great time for my wife’s birthday. This place would be great for families as well, lots of stuff to do for the kids. The location was perfect. We will definitely be back.
It was a perfect location for our 12 person group. Within walking distance to restaurants, shops and beach. Clean and spacious. Lovely ambiance and vey well put together.
This place by far exceeded all of our expectations. It was SUPER clean, was fully stocked and was in the best location. We would grill on the porch and walk to get ice cream a block away. The week went by so fast, we didn’t want to leave. We now can’t wait to go back!Also, the host was THE BEST. He answered all of our texts within seconds and was overall a pleasure to deal with.I HIGHLY recommend this property!!!
Property was beautiful, the pool was under construction and we knew that going in, but the team worked hard to get the pool ready for our family, and maybe was not totally completed but was amazing and we were able to use it - a big bonus for older parents traveling with us. Can't say enough about Justin and Gary, great to work with, awesome communication, and we look forward to staying here again. Best place by beach in Sarasota, no question, and I've been coming here for 30+ years.
I wish I could give this house 1000 stars! We absolutely LOVED our stay at the pirate house. Gary and his team were incredible, answering all of our questions and extremely responsive if we had any questions during our stay. The house has everything you could ever need and more. It is in the perfect location, walkable to everything. We had a wide range of ages (2 year old, teenage girls and adults) and everyone had plenty of space. If yo are considering renting this house, do it, you will not regret it! We will be back!!!
Wish I could give The Pirate House and Host Justin 12 stars! Our extended family spent Christmas week there. The home, the location and the host all were spectacular! Home is stunning, superbly equipped, immaculate and directly across from the very short walkway to beautiful and wide Lido Beach. One block walk to the high end restaurants and stores of St. Armand’s Circle. Justin even bought a gift for our grandson. Overall it was just a wonderful experience. You won’t find a better vacation rental or host anywhere. 12 Stars!
We started planning our vacation almost a year ago from start to finish Gary and Justin were amazing . Anytime I had any questions they promptly answered. We had a large family ranging in ages from 60 to 8 years old … 15 in total
The home is Beautiful plenty of room for everyone to escape if they needed to and comfortably have their own space.
The home has everything you could imagine,
Every little detail has been thought of.
The new pool was a huge hit !!
It was hard to leave .
But we will be back for sure !!!
Thank you Gary and Justin for making the planning so easy :)
We could not have asked for better accomodations for this week-long beach / baseball / spring break trip for our group of extended family and friends. The house is large, comfortable, perfectly located, and well-equipped for resting, cooking, and hanging out. It's big enough to accomodate a huge group but still allow plenty of space and privacy for everyone. Beds are super comfortable. Roof top deck with hot tub is amazing at sunrise and sunset. The grill is large and powerful enough to cook big dinners in no time. The location could not be better in Lido - steps to the beach or a short walk to the circle for anything you need (mostly ice cream, in our case). Justin (owner) and Gary (manager) went above and beyond to make sure our stay was perfect, including picking up additional pack n plays to make sure the three infants in our group were taken care of. We will be back - if you are considering this house, just book it; I can't imagine a better place to stay in the area.
We stayed at The Pirate House while in Sarasota for our destination wedding. I cannot say enough about this house as it fit all of our needs perfectly! The fact that each bedroom had it's own en suite bathroom was very convenient for us as well as our family that stayed with us. We were very impressed with all the unique and high end features in this home, which made leaving even more difficult than it already was! All of us kept saying "they thought of everything" as in the house is stocked with everything you will need for your stay! The house is conveniently located within a very short walking distance of St. Armands Circle which was great to be able to walk to for food, drinks, and shopping. The spectacular Lido Beach, where our ceremony was held, is a quick one minute walk from the house. Most importantly, it was an absolute pleasure to work with Gary. The ease of communication made my life easier while planning all the other details of my wedding. I hope to be able to return to The Pirate House in the future!
We had a family bday to be in the area for and stumbled onto the Pirate house. We had 8 adults staying in 5 rooms with private baths for each. The house is well laid out with all the need amenities from plate, flatware, grills, lots of glassware and so on. The "smart" features are amazing and surprisingly easy to use so don't be concerned- more importantly Gary was more than willing to come by and clarify a few things on day 2. He brought us two irons and ironing boards too. I fell the most important thing is does the host want you to enjoy the property and come back and I would say there is no doubt that is the case.
I want to add that the roof area is awesome on a warm evening when the stars come out or the sun is rising or setting, or just to get some sun during the day.
The beach is literally 2 minutes walk if you are slow.
We had several meals in even though there are amazing restaurants 4 minutes away at St. Armand's circle. It was great to go have a meal and drinks and not have to drive back when we did go out.
The game room was a blast too. If you have a small group and want to go enjoy an amazing area in an awesome house- this it the place.
The Pirate House is truly a treasure on Lido Key! It was a perfect home for our destination beach wedding. This house is spectacular! It is loaded with modern technologies which makes it great for entertaining. We loved the SONOS system to play music throughout the house, from the Roof top, to the balcanys, to the ground level gameroom. The main floor (2nd story) has a great room which was perfect for our family to gather in. The views from the balconies are simply breathtaking! Bonus note: All drinking water and ice makers are supported by Reverse Osmosis Systems (yeah, I’m a water snob).
This house is loocated a short distance from St Armand’s Circle and the beach where our wedding was held.
Our daughter, the bride, was thrilled that the masterbedroom and bath was large enough for her and all bridesmaids to get ready in. That really helped with the wedding day jitters! This room also has a world class shower and water closet.
We were extremely pleased with the communication with the host and the local management contact. We also appreciated all of the additional extras that were provided by the host. This is a very clean and classy atmosphere.
We highly recommend “The Pirate House” and look forward to staying here again.
Not only was our host, Gary welcoming and informative, but when we reached out to him during our stay, he was always timely and helpful. Also, the property was fantastic.
Incredible house. Incredible vacation. This house has everything you could want in a vacation. We had a group of 12 with ages ranging from 1-76. Everyone felt comfortable and there was plenty for everyone to do. The pool is incredible and almost made the beach an afterthought. I would recommend this house to anyone. We would love to revisit this place in the future.
Our stay at this house was the best VRBO experience and house we've ever stayed at. We have already requested for 2 more trips. From the host Gary to the house and all that it offers it is all top notch. Gary welcomed us and showed us everything we would need to know and was 100% available for any questions we had. We had adults, young adults, teens and children with us and everyone had a fantastic time and also their own space. Looking forward to returning very soon