NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach
Experience the tranquility of Sarasota Bay from this beautifully updated 4th-floor penthouse condo in Longboat Key. With elevator access and panoramic water views, this coastal home offers the perfect balance of comfort and convenience for an extended winter escape or seasonal stay. New listing which is why there is only 1 review.
THE SPACE • 2 bedrooms / 2 baths – King in primary, Queen in guest room • Modern bathrooms with walk-in shower and soaking tub • Fully equipped kitchen with bar seating and separate dining area • Open living space with panoramic bay views • 3 HD Smart TVs, Wi-Fi, and cable included • Washer/dryer inside the unit
COMMUNITY AMENITIES • 2 heated pools, fitness room, tennis & pickleball • Shuffleboard and community grills • Marina access for kayaks and paddleboards • Covered parking and well-maintained common areas
LOCATION • Short walk to the beach • Close to restaurants and shopping at St. Armands Circle • Short drive to Longboat Key dog park • Easy drive to downtown Sarasota attractions
GOOD TO KNOW • A signed renter agreement is required upon booking confirmation and guest will be required to do a background check for HOA approval. • Pet-friendly (small dogs less than 35lbs, limit 2. $200 one time fee ) • 2-month min stays in peak season (Dec–Apr) • $250 Cleaning Fee
Wake up to water views, relax by the pool, and explore everything the island offers — the perfect spot to spend your season on the Gulf Coast.
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Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
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Gulf front 2-bedroom condo with private beach central Longboat Key
Longboat Key
Gulf front 2-bedroom condo with private beach central Longboat Key
Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
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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 indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Longboat Key
Located in Longboat Key, this condo is by the sea. 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 Bradenton Beach 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 Ed Smith Stadium. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
Longboat Key, FL
What's nearby
Longboat Key Beaches - 3 min walk - 0.3 km
Lido Beach - 10 min drive - 12.9 km
St. Armands Circle - 12 min drive - 14.3 km
IMG Academy - 21 min drive - 23.6 km
Siesta Key Beach - 32 min drive - 29.1 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 31 min drive
Restaurants
7-Eleven - 15 min drive
South Philly Cheesesteak Co. - 24 min drive
Pork Belly's Eatery And Catering Co. - 15 min drive
Mar Vista Dockside Restaurant & Pub - 6 min drive
Pesto Bistro & Wine Bar - 15 min drive
Frequently asked questions
Does NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach?
As of 13 Apr, 2026, prices found for a 1-night stay for 2 adults at NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach on 14 Apr, 2026 start from S$363, 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.
Is NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach pet-friendly?
Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.
How much is parking at NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach?
On-site parking is available at the property.
What time is check-in at NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach?
Check-in begins at 4:00 PM.
What time is check-out at NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach?
Checkout is at 11:00 AM.
Where is NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach located?
Situated by the sea, this condo building is 0.2 mi (0.3 km) from Longboat Key Beaches and within 3 miles (5 km) of Cannons Marina and Longboat Key Public Tennis Center. Jewfish Key and Bradenton Beach are also within 6 miles (10 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Very much enjoyed my stay at this Windward Bay property. Well prepared, fully stocked, and very welcomed. Would stay here again.JP
Jon P.
Stayed 94 nights in Dec 2024
About the host
Hosted by Janet Allen
We love to travel and believe the best memories are made when you can truly relax. Hosting gives us the chance to help others experience that same feeling — a comfortable, thoughtfully equipped space that feels like home the moment you arrive.
Why they chose this property
At Windward Bay, enjoy panoramic views of Sarasota Bay by night and easy beach access to catch the island’s best sunsets.
What makes this property unique
We thoughtfully redesigned this condo to capture every view and create a space that feels open, comfortable, and easy to enjoy.