10/10 Excellent
Jon P.
14 April 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Windward Bay PH5 Winter 2025
Jon P.
Stayed 94 nights in Dec 2024
Condo
Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach
Condo in Longboat Key with fitness centre and outdoor pool
Photo gallery for Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach
Reviews
10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4
Popular amenities
Explore the area
- Place, Longboat Key Beaches
- Place, Coquina Beach
- Place, IMG Academy
- Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
Rooms & beds
2 bedrooms (sleeps 4)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
2 bathrooms
Bathroom 1
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Bathtub · Toilet · Shampoo · Hair dryer
Spaces
Kitchen
Separate dining area
Outdoor play area
About this property
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.
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.
• Pet-friendly (breed approval + HOA application required, small dog less than 35lbs, limit 2. $200 one time fee )
• One-month minimum rental per HOA rules
• Preference for 2-month 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.
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.
• Pet-friendly (breed approval + HOA application required, small dog less than 35lbs, limit 2. $200 one time fee )
• One-month minimum rental per HOA rules
• Preference for 2-month 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.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Have a question?
BetaGet instant answers with AI powered search of property information and reviews.
Similar properties
Longboat Key 1st Floor 2 bed/2 bath, Bayside Recreation-Beach Across the Street
Longboat Key 1st Floor 2 bed/2 bath, Bayside Recreation-Beach Across the Street
- Washer
- Dryer
- Pet-friendly
- Air conditioning
House Rules
Check in after 4:00 PM
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
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
About the area
Longboat Key
Longboat Key is home to this condo. 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 Coquina Beach and Lido Beach. Mote Marine Laboratory & Aquarium and Marie Selby Botanical Gardens are also worth visiting.
Longboat Key, FL
What's nearby
- Longboat Key Beaches - 3 min walk - 0.3 km
- Coquina Beach - 7 min drive - 9.5 km
- Lido Beach - 11 min drive - 12.9 km
- IMG Academy - 22 min drive - 25.0 km
- John and Mable Ringling Museum of Art - 24 min drive - 24.1 km
Getting around
Restaurants
- South Philly Cheesesteak Co. - 24 min drive
- Riva - 6 min drive
- Longboat Key Club (The Tavern & Whisky Bar) - 7 min drive
- Portofino - 5 min drive
- Mar Vista Dockside Restaurant & Pub - 6 min drive
Frequently asked questions
Reviews
10
Exceptional
10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
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.
Tell us how we can improve our siteShare feedback