RARE LATE-FALL OPPORTUNITY: NOVEMBER & DECEMBER 2026 AVAILABLE FOR A TWO-MONTH MINIMUM STAY AT $10,000, OFFERING A $8,000 SAVINGS. START EVERY DAY ON VACATION WITH A SUNRISE AND END IT WITH A SUNSET. From the first light of sunrise dancing across Sarasota Bay to the breathtaking sunsets over the Gulf of Mexico, this penthouse offers the best of both worlds, and the very essence of Longboat Key living. Bay views grace the eastern side of the residence, while the large kitchen window and entry door offer views west toward the Gulf. Gather each evening along the Gulf-view catwalk to watch spectacular sunsets paint the sky over the water. It’s a daily tradition cherished by owners, neighbors, and guests alike, often enjoyed from a beach chair with a favorite beverage in hand. Designed for comfort and relaxation, this two bedrooms and two bath coastal retreat features a newly remodeled open kitchen with island seating, two newly renovated bathrooms, and an inviting open living and dining area. The bright Florida Room is filled with natural light, creating the perfect spot for morning coffee, reading, or simply taking in the peaceful surroundings. Arrive with ease and park directly in your private under-building garage parking space, complete with a dedicated storage closet for all your beach gear. Perched on the top floor, this penthouse residence offers an added sense of tranquility with no unit above. The beautifully updated kitchen is fully equipped for everything from casual breakfasts to gourmet dinners. Pick up fresh ingredients from local farmer’s markets or explore the many outstanding dining destinations located just minutes away. Nestled within the 26-acre waterfront community of Windward Bay, guests enjoy access to an impressive collection of resort-style amenities. Highlights include two heated swimming pools, tennis and pickleball courts, two marinas, kayak storage, shuffleboard, a clubhouse with kitchen, library, fitness center, saunas, multiple fire pits, and barbecue areas throughout the grounds. Nature lovers will appreciate the abundance of wildlife, scenic walking paths, and more than a half mile of waterfront trails. Whether your days are spent boating, fishing, kayaking, beachcombing, or simply relaxing in the Florida sunshine, the location places you close to everything. Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and renowned arts and cultural attractions are all nearby. Guests return year after year for the exceptional combination of comfort, location, and coastal charm. In fact, one couple has made this their January through March home away from home for many seasons. More than just a place to stay, this is the kind of vacation retreat where cherished memories are made and lasting traditions begin. Your perfect Longboat Key vacation begins here.
Property Details
Price:
$9,000
MLS #:
A4706064
Status:
Active
Beds:
2
Baths:
2
Type:
Rental
Subtype:
Condominium
Subdivision:
WINDWARD BAY AMD
Neighborhood:
34228longboatkey
Listed Date:
Sep 15, 2026
Finished Sq Ft:
1,325
Total Sq Ft:
1,325
Lot Size:
1,161,752 sqft / 26.67 acres (approx)
Year Built:
1975
See this Listing
Schools
Elementary School:
Anna Maria Elementary
Middle School:
Martha B. King Middle
High School:
Bayshore High
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Ice Maker, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile
Heating
Electric
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, Open Floorplan, Solid Wood Cabinets, Thermostat, Walk-In Closet(s), Window Treatments
Laundry Features
Inside
Levels
One
Exterior
Association Amenities
Cable TV, Clubhouse, Elevator(s), Fitness Center, Laundry, Pickleball Court(s), Pool, Recreation Facilities, Sauna, Shuffleboard Court, Tennis Court(s), Trail(s), Wheelchair Access
Attached Garage YN
1
Community Features
Boat Slip, Dock, Fishing, Marina, Water Access, Waterfront, Association Recreation – Owned, Clubhouse, Fitness Center, No Truck/RV/Motorcycle Parking, Pool, Tennis Court(s)
Covered Spaces
1
Direction Faces
West
Exterior Features
Lighting, Outdoor Grill, Private Mailbox, Storage, Tennis Court(s)
Garage Spaces
1
Lot Features
Near Golf Course, Near Marina, Near Public Transit, Street Dead-End
Parking Features
Assigned, Covered, Ground Level, Guest, Under Building
View
Trees/Woods, Water
Waterfront Features
Waterfront, Bay/Harbor
Window Features
Shades
Financial
HOA Name
Meryem Billaouadil
HOA Phone
941-383-3571
Map
Community
- Address4540 GULF OF MEXICO DRIVE UNIT PH2 LONGBOAT KEY FL
- SubdivisionWINDWARD BAY AMD
- CityLONGBOAT KEY
- CountyManatee
- Zip Code34228
Subdivisions in LONGBOAT KEY
- 7981 – LONGBOAT KEY MOORINGS
- 8177 – LONGBOAT KEY MOORINGS MARINA 2
- AQUARIUS CLUB
- ARBOMAR APTS
- ARIA LONGBOAT KEY
- AVIGNON VILLAS
- BAILEY-DOBSON
- BAY HARBOUR APTS
- BAY ISLES
- BAYOU HAMMOCK
- BAYPORT
- BAYPORT BCH & TEN PH A
- BAYPORT BCH & TEN PH B
- BAYPORT BCH & TEN PH C
- BAYPORT BCH & TEN PH D
- BAYPORT BCH & TEN PH E
- BAYPORT BCH & TEN PH F
- BAYPORT BEACH & TENNIS CLUB PH D
- BAYVIEW ESTATES
- BEACH HARBOR CLUB
- BEACHES OF LONGBOAT KEY
- BEACHES OF LONGBOAT KEY PH-1
- BEACHPLACE
- BEACHPLACE 1
- BEACHPLACE I
- BEACHPLACE II
- BEACHPLACE III
- BOATHOUSE ON LONGBOAT
- BONAIRE AT LONGBOAT KEY
- BUTTONWOOD COVE
- BUTTONWOOD HARBOR
- CASA DEL MAR
- CEDARS EAST SEC 1
- CEDARS EAST SEC 2
- CEDARS EAST SEC 3
- CEDARS WEST OF LONGBOAT INC
- CHARLIES
- CLUB LONGBOAT BEACH & TENNIS
- CONRAD BEACH
- COQUINA BEACH
- COREYS LANDING
- COUNTRY CLUB SHORES
- COUNTRY CLUB SHORES IV
- COUNTRY CLUB SHORES SEC 01
- COUNTRY CLUB SHORES SEC 02
- COUNTRY CLUB SHORES SEC 03
- COUNTRY CLUB SHORES SEC 1
- COVERT II
- DOCK ON THE BAY SEC 1
- DREAM ISLAND
- EMERALD HARBOR
- EMERALD HARBOR UNIT 1 REV
- EN PROVENCE
- FAINE APTS
- FAIRWAY BAY
- FAIRWAY BAY 1
- FAIRWAY BAY 2 PH 1
- FAIRWAY BAY 2 PH 2 & 3
- FAIRWAY BAY 3
- FRACTIONAL SUB
- GRAND BAY 1
- GRAND BAY 2
- GRAND BAY 3
- GRAND BAY 4
- GRAND BAY 5
- GRAND BAY 6
- GULFSHORE OF LONGBOAT KEY
- GULFSHORE OF LONGBOAT KEY, INC
- H & M ASSOC
- HARBOR OAKS
- HARBOR OAKS PH I & II
- HARBOUR COURT
- HARBOUR OAKS
- HARBOUR OAKS 2
- HARBOUR VILLA CLUB AT THE BUCCANEER
- HARRIS BAYOU
- HIDEAWAY BAY SUB
- HOOTON
- INN ON THE BEACH PH I
- INN ON THE BEACH PH II
- INN ON THE BEACH PH III
- ISLANDER CLUB OF LONGBOAT
- ISLANDS WEST
- JEWFISH KEY
- L AMBIANCE
- L AMBIANCE 1
- L AMBIANCE AT LONGBOAT KEY CLUB PH 02
- LA FIRENZA
- LAGUNA YACHT VILLAGE
- LAGUNA YACHT VILLAGE A CONDO
- LANDS END
- LIGHTHOUSE POINT
- LONGBEACH
- LONGBEACH ON LONGBOAT KEY
- LONGBEACH REV OF R P JORDANS SUB
- LONGBOAT ARMS
- LONGBOAT BEACH HOUSE
- LONGBOAT HARBOR TOWERS
- LONGBOAT HARBOUR
- LONGBOAT HARBOUR TOWERS
- LONGBOAT KEY
- LONGBOAT KEY CASA DEL MAR
- LONGBOAT KEY ESTATES
- LONGBOAT KEY MOORINGS
- LONGBOAT KEY MOORINGS MARINA
- LONGBOAT KEY MOORINGS MARINA 2
- LONGBOAT KEY TOWERS
- LONGBOAT LANDING
- LONGBOAT SANDPIPERS
- LONGBOAT SHORES REV
- LONGBOAT TERRACE
- MANCHESTER BAY
- MARINA BAY
- MARY REGINA REESE
- MCCALLS BEACH CASTLE
- NEPTUNE ON LONGBOAT KEY
- NEW PASS SHORES
- NORTHGATE OF LONGBOAT KEY
- PELICAN HARBOUR & BEACH CLUB
- PIERRE
- PLAYERS CLUB
- PLAYERS CLUB 3
- PLAYERS CLUB I
- PLAYERS CLUB III
- PLAYERS CLUB IV
- PORTOBELLO
- POSITANO
- PRESERVE/LONGBEACH
- PRIVATEER NORTH
- PRIVATEER SOUTH
- PROMENADE
- QUEENS HARBOUR
- RAUCH
- REGENT COURT
- REGENT PLACE PH 1
- REGENT PLACE PH 2
- RESUB OF LTS 2B&3B OF SLEEPY LAGOON ADD
- SABAL COVE
- SAINT JUDES APTS
- SALTY ACRES
- SANCTUARY I
- SANCTUARY II
- SANCTUARY III
- SANCTUARY IV
- SAND CAY
- SANDS POINT
- SEA GATE CLUB
- SEA PINES
- SEAGRAPE INN
- SEAPLACE
- SEAPLACE I
- SEAPLACE II
- SEAPLACE III
- SEAPLACE V
- SEAPLACE VI
- SEASIDE OF LONGBOAT
- SILVER SANDS
- SLEEPY LAGOON
- SLEEPY LAGOON PARK
- SLEEPY LAGOON PARK 2
- SLEEPY LAGOON PART NO 2
- SPANISH MAIN YACHT CLUB CONDO
- ST REGIS LONGBOAT KEY
- ST. REGIS
- ST. REGIS LONGBOAT KEY
- SUNSET BEACH
- SUNSET BEACH PH 2
- SUTTON PLACE
- T J OXFORD
- TANGERINE BAY CLUB
- THE BANYAN BAY CLUB
- THE GRANDE AT LONGBOAT KEY
- THE PRESERVE/LONGBEACH
- THE SHORE
- TIFFANY PLAZA
- TRITON COVE
- TURTLE CRAWL SEC 36 TOWNSHIP 35S RANGE 16E
- TWIN SHORES MOBILE HOME
- VEINTE
- VILLA DI LANCIA PH 1
- VILLA DOS PALMAS
- WATER CLUB 01 AT LONGBOAT KEY
- WATER CLUB AT LONGBOAT KEY
- WATER CLUB II/LONGBOAT KEY
- WENDY
- WESTCHESTER
- WESTCHESTER APTS
- WESTCHESTER CONDO APTS UN 3
- WHITNEY BEACH
- WINDING OAKS
- WINDWARD BAY
- WINDWARD BAY AMD
Market Summary
Current real estate data for Rental in LONGBOAT KEY as of Sep 16, 2026
140
Rental Listed
746
Avg DOM
5
Avg $ / SqFt
$9,113
Avg List Price
Property Summary
- Located in the WINDWARD BAY AMD subdivision, 4540 GULF OF MEXICO DRIVE UNIT PH2 LONGBOAT KEY FL is a Rental for sale in LONGBOAT KEY, FL, 34228. It is listed for $9,000 To schedule a showing of MLS#a4706064 at 4540 GULF OF MEXICO DRIVE UNIT PH2 in LONGBOAT KEY, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of COLDWELL BANKER REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 4540 GULF OF MEXICO DRIVE UNIT PH2
LONGBOAT KEY, FL
