Available for Annual Lease on September 15th. BEAUTIFUL BAY ISLAND is a gated, well maintained over 55+ complex in the heart of South Pasadena. You must see this beautifu...

Waterfront! This 2nd floor unit checks all of the boxes; End Unit, Split Plan, Covered/Screened Patio and In-Unit Laundry. There are new cabinets, stainless steel applian...

Experience the ultimate Florida lifestyle in this beautifully updated, fully furnished 1-bedroom, 1-bathroom condo on the 4th floor of the highly sought-after Bay Island ...

Welcome to Harbourside, Your Winter get away retreat. Beautifully updated 2 bedroom/ 2 bath available November 2026 thru May 1, 2027. Kitchen has been remodeled with G...

Welcome to Harbourside and the opportunity to live in this luxurious waterfront community. Annual Condo available to lease. This 5th Floor Condo has a Beautiful Updated ...

Welcome to Harbourside, a Luxurious Waterfront condominium community. Enjoy the Water views from this 1300 sq ft Beach Walker end unit, Bldg 9. End units have a wrap aro...

This resort-style waterfront living in the 55+ community of Bay Island. Located at 7920 Sun Island Drive S, Unit 205, South Pasadena, Florida, this spacious 3-bedroom, 2-...

Welcome to Saratoga in the sought after 55+ Waterfront community of Bay Island. This "Unfurnished" Waterfront condo has been completely remodeled and waiting for its new...

503 The Ambassador Building at Bay Island – A Premier 55+ Waterfront Community Located in the highly sought-after Ambassador Building at Bay Island, this spacious fifth...

Completely renovated 2-bedroom, 2-bath home located in the heart of South Pasadena! This beautifully updated property has been renovated from top to bottom and features a...

STUNNING Waterfront Rental on the open Intercoastal Private Dock & Brand-New Boat lift Live the Florida dream in this absolutely gorgeous waterfront home perfectly posit...

Welcome home to your dream come true! Located on Sun Island just a hop skip and a jump away from South Pasadena shops, stores, grocery, restaurants, and hospital as well ...

One or more photo(s) has been virtually staged. This lovely water front condo is ready for immediate occupancy. Available furnished for short-term rental. Experience the ...

Welcome to Bay Island, a guarded, gated 55+ waterfront community. This one bedroom, one bath condo has been tastefully updated and the private porch is only steps away fr...

Discover the relaxed elegance of waterfront living at Bay Island, a highly sought-after 55+ gated community in South Pasadena. Located in the Lexington building, this ren...

This stunning, upgraded, pet-friendly waterfront condo offers an authentic Florida lifestyle. The open floor plan flows to an oversized balcony with breathtaking water vi...

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Move In Special - 2 months...

Pasadena Cove offers great amenities and accessibility to all the BEST beaches, shopping and dining in Pinellas county, This 1 bedroom, 1 and a half bathroom unit on the ...

Welcome to your perfect Florida escape in beautiful South Pasadena! This stunning, fully furnished 2-bedroom, 2-bath waterfront condo offers the ideal blend of comfort, c...

Resort-style living in a gated 55+ community on Boca Ciega Bay! This fully furnished 2BR/2BA condo (2nd bedroom converted to a den with sleeper sofa) is filled with antiq...

Welcome to resort-style living in the highly sought-after gated 55+ community of Bay Island. This beautifully maintained Turn Key rental opportunity comes fully furnished...

This is your chance to live in a completely update water front condo. It is a two bedroom two bath condo with a open concept, the kitchen is open to the large dinning, li...

Welcome to your updated waterfront corner unit in the highly sought-after Bay Island, a 55+ gated community in South Pasadena. Located in the Yorktown building, this reno...

Beautiful 1-bedroom apartment featuring a spacious walk-in closet, central A/C, and brand-new appliances, located in a prime waterfront location and nestled within a char...

Harbourside Windwards Bldg Summer rental available. Updated, beach-themed, waterfront condo in Harbourside Community available April 21, thru October 31, 2026. Monthly re...

Waterfront Paradise! Welcome to Sunrise at Harbourside! Harbourside is a Luxurious Waterfront condominium community, immaculately maintained with 24/7 guard gate. This 2 ...

Can be rented furnished of unfurnished! The beautiful two bedroom and two bathroom condo is in the resort community of Pasadena Cove. The condo has two large bedrooms and...

Are you looking for a peaceful neighbourhood, close to all amenities **** calm & charming Home! Privacy and modern living. LOCATION LOCATION ! Your family will be close t...

This gated resort-style condominium provides the perfect combination of relaxation and excitement. It is ideally located close to the beautiful beaches of the barrier isl...

SUMMER RENTAL! Beautiful updated waterfront condo available June 15th thru November 1st, 2026. Monthly rent is $2300.00 and includes basic cable, internet, water, sewer, ...

VACATION IN PARADISE! Welcome to your coastal retreat in this beautiful 3-bedroom, 2-bath third-floor condo. Everything you need for an extended stay. Modern kitchen and ...

Experience coastal living in this beautifully furnished 1-bedroom, 1.5-bath condo located in the exclusive, gated Bay Island community one of South Pasadena's premier 55+...

One or more photo(s) has been virtually staged. Move In Special - 2 months free rent if lease signed by 7/31/26. This is Florida Living! Stunning 2-Bedroom Apartment in a...

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Move In Special - 2 months free rent if lease signed by 7/31/26. This is F...

One or more photo(s) has been virtually staged. Move In Special - 2 months free rent if lease signed by 7/31/26. DIRECT WATERFRONT UNIT!!!! One or more photo(s) has been ...

AVAILABLE NOW TILL OCTOBER 31ST. Check out the fabulous Bay Islands 55 plus Resort-like waterfront complex 2 BED 2 BATH CONDO where you will find some serious amenities. ...