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NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach

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Spacious living area with panoramic views across Sarasota Bay.
Bay and Ocean views!
Fully equipped gourmet kitchen with bar seating and modern appliances.
Peaceful primary suite with King bed and direct Bay views
Second heated community pool located next to the Community Clubhouse.

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4101.8 sq m

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Explore the area

View map
Longboat Key, FL
  • Place, Longboat Key Beaches
    ‪5 min walk‬
  • Place, Lido Beach
    ‪10 min drive‬
  • Place, Siesta Key Beach
    ‪32 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪27 min drive‬

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

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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House Rules

Check in after 4:00 PM
Minimum age to rent: 35
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

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 Longboat Key Beaches and Bradenton 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 cycling and ecotours nearby.
Map
Longboat Key, FL

What's nearby

  • Longboat Key Beaches - 5 min walk - 0.4 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 3 May 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 5 May 2026 start from AU$396, 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jon P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Windward Bay PH5 Winter 2025

Very much enjoyed my stay at this Windward Bay property. Well prepared, fully stocked, and very welcomed. Would stay here again.JP
Stayed 94 nights in Dec 2024
Verified

10/10 Excellent

Roy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We love it turn key ready
Stayed 54 nights in Feb 2026

About the host

Hosted by Janet Allen

Host profile image
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.

Languages:

English
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