Experience the ultimate in coastal luxury at the Captain’s Quarters. While most premium properties on Longboat Key strictly require a 30-day minimum stay year-round, this exclusive penthouse uniquely offers weekly rentals during the off-season months—making it the perfect, rare find for a flexible spring, summer, or fall getaway.
This upscale, third-floor corner penthouse was meticulously redesigned by the renowned Leader/Sawa Design Studio. Originally intended for the owner’s personal use, no expense was spared in creating a bright, sophisticated sanctuary flooded with southern exposure sunlight.
As the largest floor plan in the complex (1,500 sq. ft.), this spectacular unit features soaring cathedral ceilings, an open-concept modern layout, and a massive private balcony positioned perfectly away from pool noise. If you are seeking premium privacy, abundant space, and serene quietness on Longboat Key, you have found it.
Why You’ll Love the "Captain’s Quarters": - Dual Master Suites: Perfect for couples or families seeking privacy, featuring two expansive bedrooms with King beds, large custom modular closets, and independent private balconies. - Spa-Like Bathrooms: Indulge in oversized bathrooms equipped with double sinks, spacious walk-in showers, an enclosed water closet, a premium bidet seat, and natural window light. - Designer Living Spaces: Unwind on a premium Italian sectional sofa (spacious enough to accommodate two children for sleep) alongside curated modern decor and a large marble dining table that comfortably seats eight. - Massive Waterfront Patio: Relax on your incredibly quiet, roomy balcony overlooking the tranquil bay, complete with a luxury outdoor sectional sofa and lounge chairs. - Chef’s Kitchen: Fully equipped with high-end cookware, premium glassware, and brand-new stainless steel appliances, including an induction range and a refrigerator with water/ice dispensers. - Modern Conveniences: High-end Hunter Douglas blinds, an in-unit washer/dryer, a Nest thermostat, and hassle-free keyless entry so you can go straight to your unit and start your vacation.
Harbor Villa Club Amenities: - Heated Waterfront Pool & Hot Tub - Tennis Courts & 2 Dedicated Pickleball Courts - Private Boat Slips (Available for separate rental) - Covered Parking & Elevator Access
Around Longboat Key & The Neighborhood: Positioned perfectly on the island, you are just minutes away from the best local gems: - Historic Longbeach Village (3 Mins North): Stroll through this historic neighborhood—famous for the local peacocks roaming free—and enjoy incredible waterfront dining at the rustic Mar Vista or the upscale, modern Shore. - Beer Can Island (3 Mins North): Discover this hidden gem beach, famous for its beautifully weathered, uprooted Australian pines that create a stunning, deserted-island aesthetic perfect for exploring. - Local Dining & Essentials (3 Mins South): Visit Harry’s Continental Kitchens, an island staple since 1979, featuring a gourmet deli, corner store, and a fantastic upscale restaurant. - Nature & Wildlife: Hike through the coastal mangroves at Joan M. Durante Community Park just 3 minutes away, or take a short drive to explore the world-class Mote Marine Laboratory & Aquarium.
Whether you are looking to kayak, paddleboard, book a sunset fishing charter, explore the vibrant shops at St. Armands Circle, or head north into the lively atmosphere of Anna Maria Island, this luxury villa serves as your perfect, peaceful home base.
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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 indicated that there is a smoke detector on the property
About the area
Longboat Key
Located in Longboat Key, this condo is on the waterfront. Mote Marine Laboratory & Aquarium is a popular attraction and the area's natural beauty can be seen at Longboat Key Beaches and Coquina Beach. Looking to enjoy an event or a game while in town? See what's happening at Longboat Key Public Tennis Center or IMG Bollettieri Tennis Academy. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and hiking nearby.
Longboat Key, FL
What's nearby
Cannons Marina - 5 min walk - 0.4 km
Longboat Key Beaches - 12 min walk - 1.1 km
Coquina Beach - 6 min drive - 5.8 km
Lido Beach - 20 min drive - 16.7 km
Siesta Key Beach - 43 min drive - 33.2 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 27 min drive
Restaurants
7-Eleven - 13 min drive
Anna Maria Oyster Bar on the Pier - 8 min drive
McDonald's - 15 min drive
Tide Tables - 9 min drive
Cortez Clam Factory - 12 min drive
Frequently asked questions
Is GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!! pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!!?
As of 6 August 2026, prices found for a 1-night stay for 2 adults at GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!! on 15 August 2026 start from NZ$2,571, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!!?
On-site parking is available at the property.
What time is check-in at GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!!?
Check-in begins at 4:00 PM.
What time is check-out at GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!!?
Checkout is at 10:00 AM.
Where is GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!! located?
Situated on the waterfront, this condo building is within a 15-minute walk of Cannons Marina and Longboat Key Beaches. Coquina Beach is 2.7 mi (4.3 km) away.
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We love staying here. Beautiful location and beautiful property. We love the owners' taste in aesthetics.
Jacob G.
Stayed 7 nights in Dec 2024
Response from VrboOwner on 22 April 2025
Your five-star review means the world to us! We're so happy to hear that you enjoyed your stay at our vacation rental. We'd love to have you back for another fantastic getaway!
So very pleased with the unit on LBK. Modern, spacious, quiet and clean.
Jacqueline R.
Stayed 11 nights in Oct 2023
Response from VrboOwner on 18 September 2025
Thank you for your wonderful review! We’re thrilled to hear you found the condo modern, spacious, quiet, and clean. It’s always rewarding to know our guests enjoyed their stay, and we look forward to welcoming you back.
This is a beautiful condo in a great location. We really couldn’t believe how spacious, light and beautifully furnished this place is. If you get a chance book it now.
David P.
Stayed 7 nights in Mar 2023
Response from VrboOwner on 18 September 2025
Thank you for your kind words! We’re thrilled you loved the space, light, furnishings, and location. It’s wonderful to know you felt the condo was exceptional, and we hope to welcome you back soon.
Verified review
4/10 Poor
Crystal F.
30 June 2026
Disliked: Listing accuracy
Not upscale "Penthouse" but an average & modest 3rd floor corner unit condo. 1st day and it was warm in unit. Thermostat was flashing "warning" alert. Owner controls temperature, you'll wake hot, they turn air up to 73 at night. 2nd day Sunday, back from beach 1 pm, it was 84 degrees inside condo. I had to contact mgt. Co. they had to contact HVAC co. Waited 2 hrs for HVAC to show. HVAC there 90 mins. cleaning duct & filters. Took 5 hours after he left to get unit cooled, last, very hot week of June. Can not swim in the pool the water was dingy and hotter than a bowl of soup. Reported it to host but the pool was never corrected. Major warning about the noise. You will not be able to sleep, there is a huge gas run pump outside the condo pumping water out of the waterway, runs 24/7, extremely loud. Imagine an old washing machine stuck on the spin cycle. Also, there is massive construction on the property beside the unit. You will be constantly subjected to extremely loud noise. Debris removal lifting and dumped into steel containers. Backup beeping large bulldozers, horns, steel girders being driven into ground by pounding equipment. It goes on till 6 pm. It was not the relaxing vacation I had planned. Also, the condo next door has began permitted remodeling so there is a lot happening there.
Crystal F.
Stayed 7 nights in Jun 2026
Response from VrboOwner on 15 July 2026
Thank you for your feedback about Harbor Villa Club 314 . We’re sorry your stay fell short of expectations.
We apologize for the HVAC issues and the uncomfortable heat. During your stay we arranged for a technician to attend; we’ll follow up with a full inspection of the system, thermostat controls, and ducting to ensure cooling performance and that temperature settings are appropriate. We regret the long wait you experienced.
The pool condition you described is unacceptable. Unfortunately BBG does not control the Pool or any of Harbor Villa Amenities. We’ve passed your report to the HOA.
Noise from the pump and nearby construction should have been disclosed and is not the relaxing experience you expected. We will investigate the pump noise with the HOA/owner, review construction schedules with the property team, and look for ways to minimize disturbance. We’ll also review our listing and pre-arrival information to make sure ongoing works and noise levels are clearly communicated.
Finally, we will review the unit description to ensure it accurately reflects the space. Thank you for bringing these issues to our attention — we’ll use your comments to make improvements.
Excellent condo. Very clean and well equipped with new furnishings. Wonderful kitchen. Great views of the bay. Couldn't be more pleased.
Diane K.
Stayed 12 nights in Dec 2022
Response from VrboOwner on 18 September 2025
Thank you for your great review! We’re delighted you found the condo clean, well-equipped, and enjoyed the kitchen and bay views. It’s always a pleasure to host guests who appreciate the details, and we look forward to your next stay.
Beautiful, spacious condo with lovely view of the bay.
We had a wonderful time at the condo together. It was nocey appointed and very comfortable. The location was perfect and central to Longboat Key and Anna Maria. The view was spectacular, too! Thank you for hosting us. We'll be back!!
Cindy M.
Stayed 7 nights in Jun 2024
Response from VrboOwner on 26 July 2024
Hi Cindy, we are so appreciative of your positive feedback! We are so glad to hear that our guests had a great time and we love that you enjoyed the location and views of the Harbor Villa Club property. We are so glad to have hosted you and are excited to see you again in the future!
Everything about this property was perfect!
Very comfortable and close to both Anna Maria Island and Siesta Key
The pool was perfect for a pool day.
Spent Beach days at Coquino Beach and Siesta Key. Favorite restaurants on Longboat was Dry Dock and Whitneys. Speaks Clam bar and Colombian are our favorites at St Armand’s Circle.
Would definitely pick this Condo again! Beautiful view from a well apportioned unit
Lynn F.
Stayed 7 nights in Apr 2023
Response from VrboOwner on 18 September 2025
Thank you for your fantastic review! We’re so glad the condo, pool, and location made your mother-daughter trip special. We appreciate the restaurant recommendations and are delighted you enjoyed the view and amenities. We would love to host you again anytime!
Verified review
10/10 Excellent
Elaine
15 October 2023
Liked: Amenities
Unit was lovely, kitchen well stocked, good location, safe property. Bethany at Best Beach Getaways was amazing to deal with. Great customer service.
I’m annoyed that VRBO charged over two hundred dollars / service fee as they added ZERO value to the booking. In fact since I booked thru Expedia and used a different email address than my VRBO email I couldn’t even load it to my app. Had I known this would have booked direct thru Best Beach Getaways and eliminated that extra cost which did absolutely nothing for me.
The property is as nice if not nicer than portrayed on the VRBO site. Very clean, quiet, and well-appointed. It possesses all the technology and appliances you need for a great vacation stay. Great view, layout, pool and furniture. We enjoyed the condo!
The only downside was the fire system in the condo was broken. We had to evacuate the condo twice as the alarms went off on two separate days and we had to leave the complex on two other days while the water to the unit was shut off. The management company informed us of the water issue just before our stay but was not very sympathetic to any of these issues.
If the facility issues have all been dealt with, then this is a great place to stay!
Jeff C.
Stayed 7 nights in Nov 2023
Response from VrboOwner on 18 September 2025
Thank you for sharing your feedback. We are glad you enjoyed the condo’s cleanliness, layout, pool, and view. We sincerely apologize for the fire system issues and water interruptions during your stay. Your concerns about these disruptions and the management response have been shared with our team to improve communication and guest experience. We hope to host you again under smoother circumstances.
Verified review
10/10 Excellent
Jacqueline R.
30 October 2025
Jacqueline R.
Stayed 11 nights in Sep 2025
Response from VrboOwner on 11 November 2025
Thank you for the 5-star review! We appreciate you choosing Best Beach Getaways and hope to welcome you back soon.
About the host
Hosted by Best Beach Getaways
Languages:
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Premier Host
They consistently provide great experiences for their guests