Entire condo
Enjoy endless gulf views from this welcoming oceanfront condo on Longboat Key - Pearl On The Key
Beachfront condo near Lido Beach
Choose dates to view prices
Photo gallery for Enjoy endless gulf views from this welcoming oceanfront condo on Longboat Key - Pearl On The Key





Entire condo
Popular amenities
- Ocean view
- Pool
- Kitchen
- Free WiFi
- Air conditioning
- Laundry
Explore the area

Longboat Key, FL
- Longboat Key BeachesPlace, Longboat Key Beaches1 min walk
- Islandside Golf Course at Longboat Key ClubPlace, Islandside Golf Course at Longboat Key Club3 min drive
- Harborside Golf Course at Longboat Key ClubPlace, Harborside Golf Course at Longboat Key Club3 min drive
- Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)19 min drive
Room options
About the area
Longboat Key
On the beach.Within 2 miles (3 km) of this Longboat Key condo, you'll find Islandside Golf Course at Longboat Key Club and Harborside Golf Course at Longboat Key Club. Lido Beach and Quick Point Nature Reserve are also within 3 miles (5 km).
What's nearby
- Longboat Key Beaches - 1 min walk - 0.0 km
- Quick Point Nature Reserve - 3 min drive - 3.1 km
- Islandside Golf Course at Longboat Key Club - 3 min drive - 3.1 km
- Harborside Golf Course at Longboat Key Club - 3 min drive - 3.1 km
- St. Armands Circle - 6 min drive - 6.1 km
Getting around
- Sarasota-Bradenton Intl. Airport (SRQ) - 30 min drive
Restaurants
- Columbia Restaurant - 6 min drive
- Dry Dock Waterfront Grill - 2 min drive
- New Pass Grill & Bait Shop - 4 min drive
- The Old Salty Dog - 4 min drive
- Riva - 2 min drive
About this property
Entire place
You'll have the entire condo to yourself and will only share it with other guests in your party.
Enjoy endless gulf views from this welcoming oceanfront condo on Longboat Key - Pearl On The Key
Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, an exclusive beachfront community nestled on the pristine shores of Longboat Key. This 2-bedroom, 2-bathroom 7th floor condo offers breathtaking Gulf views from every room, elegant interiors, and access to resort-style amenities—making it the perfect destination for your next Florida escape.
As you step inside, you're greeted by a light, bright, and cozy atmosphere, with large windows that frame the sparkling blue waters of the Gulf. The kitchen is a chef's delight, featuring granite countertops, stainless steel appliances, and a breakfast bar with barstool seating—ideal for enjoying a quick bite or gathering with family and loved ones.
The main living space is designed for comfort and relaxation, with two plush sofas, a flat-screen TV, and an adjacent dining table that seats four comfortably—all with sweeping ocean views. Step through the sliding doors to one of the condo's two private balconies, where you can sip your morning coffee or unwind with a glass of wine as the ocean breeze rolls in.
The primary bedroom is a peaceful retreat, complete with a king-size bed, a sitting area with chairs, a TV, and its own balcony overlooking the pool and Gulf. The attached bathroom boasts an updated vanity and a gorgeous walk-in shower with modern finishes.
The second bedroom features a queen-size bed, TV, ample closet space for personal belongings, and its own private balcony with more stunning ocean views. The second bathroom includes an updated vanity and a shower/tub combo, perfect for relaxing after a day in the sun.
🌴 Community Amenities at Privateer:
Beachfront heated pool & spa
Direct private beach access
Tennis courts
Fitness center & sauna
Social room & library
Grilling area & firepit
Gated entry with secured building access
Assigned covered parking
Lush tropical landscaping throughout
Located just minutes from St. Armands Circle, golf courses, fine dining, and cultural attractions in Sarasota, this condo offers the perfect blend of relaxation and adventure.
Whether you're seeking tranquil beach days or exploring the vibrant coastal lifestyle of Longboat Key, this condo at Privateer is your perfect home away from home.
There is a communal washer and dryer facility that is on the same floor as the unit.
House Rule: No smoking. No burning candles inside of lodging. No parties. No Pets.
Your reservation may require you to fill out a Home Owners Association application that may request personal details. Any application fees required by the HOA are non-refundable.
As you step inside, you're greeted by a light, bright, and cozy atmosphere, with large windows that frame the sparkling blue waters of the Gulf. The kitchen is a chef's delight, featuring granite countertops, stainless steel appliances, and a breakfast bar with barstool seating—ideal for enjoying a quick bite or gathering with family and loved ones.
The main living space is designed for comfort and relaxation, with two plush sofas, a flat-screen TV, and an adjacent dining table that seats four comfortably—all with sweeping ocean views. Step through the sliding doors to one of the condo's two private balconies, where you can sip your morning coffee or unwind with a glass of wine as the ocean breeze rolls in.
The primary bedroom is a peaceful retreat, complete with a king-size bed, a sitting area with chairs, a TV, and its own balcony overlooking the pool and Gulf. The attached bathroom boasts an updated vanity and a gorgeous walk-in shower with modern finishes.
The second bedroom features a queen-size bed, TV, ample closet space for personal belongings, and its own private balcony with more stunning ocean views. The second bathroom includes an updated vanity and a shower/tub combo, perfect for relaxing after a day in the sun.
🌴 Community Amenities at Privateer:
Beachfront heated pool & spa
Direct private beach access
Tennis courts
Fitness center & sauna
Social room & library
Grilling area & firepit
Gated entry with secured building access
Assigned covered parking
Lush tropical landscaping throughout
Located just minutes from St. Armands Circle, golf courses, fine dining, and cultural attractions in Sarasota, this condo offers the perfect blend of relaxation and adventure.
Whether you're seeking tranquil beach days or exploring the vibrant coastal lifestyle of Longboat Key, this condo at Privateer is your perfect home away from home.
There is a communal washer and dryer facility that is on the same floor as the unit.
House Rule: No smoking. No burning candles inside of lodging. No parties. No Pets.
Your reservation may require you to fill out a Home Owners Association application that may request personal details. Any application fees required by the HOA are non-refundable.
Similar properties

Charming 2-bedroom condo with AC, fitness room in wonderful Longboat Key
Charming 2-bedroom condo with AC, fitness room in wonderful Longboat Key
Longboat Key
- Pool
- Hot tub
- Washer
- Dryer

Anna Maria Beach Condo at Bradenton Beach Club: Gulf Front Condo by Anna Maria Life Vacation Rentals
Anna Maria Beach Condo at Bradenton Beach Club: Gulf Front Condo by Anna Maria Life Vacation Rentals
Bradenton Beach
- Ocean view
- Pool
- Hot tub
- Kitchen
5.0 out of 5, Exceptional, 5 reviews
5
Exceptional
5 reviews

Anna Maria Island Club 39 Beachfront. End Unit Condo 2BR/2Bath Gulf-Front Retreat with maximum occupancy of 4 people. Community pool, Max 1 vehicle.
Anna Maria Island Club 39 Beachfront. End Unit Condo 2BR/2Bath Gulf-Front Retreat with maximum occupancy of 4 people. Community pool, Max 1 vehicle.
Bradenton Beach
- Pool
- Hot tub
- Kitchen
- Washer

Resort-style Condo with Pool and Water Views! Near Anna Maria Islands beach
Resort-style Condo with Pool and Water Views! Near Anna Maria Islands beach
Bradenton
- Pool
- Hot tub
- Kitchen
- Washer
4.0 out of 5, Very good, 2 reviews
4.0
Very good
2 reviews

LBK Dreamin' Beach Bungalow
LBK Dreamin' Beach Bungalow
Longboat Key
- Pool
- Kitchen
- Washer
- Pet friendly
4.9 out of 5, Exceptional, 27 reviews
4.9
Exceptional
27 reviews

Buttonwood Cove 204B by FVC
Buttonwood Cove 204B by FVC
Longboat Key
- Pool
- Kitchen
- Washer
- Dryer

HVC #203 - Spa/Pool - Private Paradise on LBK!
HVC #203 - Spa/Pool - Private Paradise on LBK!
Longboat Key
- Hot tub
- Washer
- Dryer
- Free WiFi

Comfortable Family Home | Close to IMG Academy & Beach.
Comfortable Family Home | Close to IMG Academy & Beach.
Bradenton
- Kitchen
- Washer
- Dryer
- Pet friendly
4.8 out of 5, Exceptional, 5 reviews
4.8
Exceptional
5 reviews
The price is CA $226
CA $226
CA $583 total
includes taxes & fees
Jan 31 - Feb 1, 2026

Charming House with Heated Pool
Charming House with Heated Pool
Bradenton
- Pool
- Kitchen
- Washer
- Dryer
5.0 out of 5, Exceptional, 2 reviews
5
Exceptional
2 reviews

Luxury Relaxation Home 8PPL Pool
Luxury Relaxation Home 8PPL Pool
Bradenton
- Pool
- Kitchen
- Washer
- Dryer
5.0 out of 5, Exceptional, 1 review
5
Exceptional
1 review
Property amenities
Beach
- On the beach
Pool/Spa
- Communal pool
Internet
- Available in the condo: Free WiFi
Parking and transportation
- Parking on site
Kitchen
- Cookware, dishware, and utensils
- Dishwasher
- Microwave
- Oven
- Refrigerator
- Stovetop
Dining
- Dining table
Bedrooms
- 2 bedrooms
- Bedsheets provided
Bathroom
- 2 bathrooms
- Bathtub or shower
- Shower
- Towels provided
Living spaces
- Dining table
- Living room
Entertainment
- TV
Outdoor areas
- Balcony
- Barbecue grill
Laundry
- Laundry facilities
Comfort
- Air conditioning
- Heating
Pets
- No pets allowed
Suitability/Accessibility
- Smoking not allowed
Location highlights
- Near a health/beauty spa
- Near a hospital
- Near a zoo
- Near an outlet shopping mall
- Near the marina
- Near the ocean
- On the waterfront
Things to do
- Golf
- Optional golf privileges
- Tennis
- Basketball nearby
- Birdwatching nearby
- Casino nearby
- Cycling nearby
- Ecotours nearby
- Fishing nearby
- Golfing nearby
- Horseback riding nearby
- Jet skiing nearby
- Kayaking nearby
- Motor boating nearby
- Parasailing nearby
- Sailing nearby
- Scuba diving nearby
- Snorkeling nearby
- Swimming nearby
- Theme park nearby
- Water skiing nearby
- Water tubing nearby
- Whale watching nearby
- Wildlife walks nearby
- Winery tours 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)
- Fire extinguisher
General
- Unit size: 1,290 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in 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
Information provided by the property may be translated using automated translation tools
Pets
- No pets allowed
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.
Property is also known as
966322