South Pasadena, FL Homes for Rent in a Gated Community

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+ waterfront enclaves. This condo offers resort-style amenities and serene water views just minutes from Florida's top-rated beaches. Enjoy peaceful mornings and breezy evenings from your private screened balcony, overlooking the

Helena Mathews ELITEEAGLE REALTY SERVICES, LL

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 occupants. Condo has 2 bedrooms, 2 baths and a open concept to enjoy the water view. Carpeted Primary Bedroom has a walk in closet and an ensuite Bath with dual sinks and walk in shower. Carpeted 2nd Bedroom has built in shelves

Kathy Lingelbach FUTURE HOME REALTY INC

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 with 2-bedrooms, 2-baths, 2nd floor condo spanning 1,045 square feet of light-filled living space and serene waterfront surroundings. The spacious eat-in kitchen is thoughtfully designed with granite countertops, stainless steel

Jac Smith KELLER WILLIAMS ST PETE REALTY

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-bathroom condominium offers breathtaking Intracoastal Waterway views from nearly every room and provides the perfect combination of comfort, convenience, and coastal charm.Step inside and discover a bright, open floor plan

Lara Magness LANGEE REALTY

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 beautiful WaterFront Unit in the Presidential Building. This condo has been updated with a spacious and bright Great Room that opens to the handsome Kitchen. Enjoy lovely tile floors throughout the condo. Both large bedrooms feature

Drew Carlyle KELLER WILLIAMS GULF BEACHES

Welcome to Harbourside and the opportunity to live in this luxurious waterfront community. Annual Condo available to lease. This 5th FloorCondo has a Beautiful Updated kitchen with lots of cabinet space and Stainless Steel appliances, 2 spacious Bedrooms and 2 Baths, Waterview from the Front eat in Kitchen area and Balcony off the Living room and Primary bedroom. Primary Bedroom has a

Kathy Lingelbach FUTURE HOME REALTY INC

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. Six pools, Tennis and Pickle ball courts, large clubhouse with his and hers separate fitness gyms, Billiards room, Ping pong room, Card room and library, Marina, an on sight social director and a 1.25-mile waterfront walking

Joe Nix BHHS FLORIDA PROPERTIES GROUP

Waterfront Paradise! Welcome to Sunrise at Harbourside! Harbourside is a Luxurious Waterfront condominium community, immaculately maintained with 24/7 guard gate. This 2 bedroom/ 2 bath condo is available for minimum 6+ months or an Annual lease starting NOW. Enjoy your morning beverage as you look out your Balcony over Boca Ciega Bay. The condo is furnished, just needs your personal belongings.

Kathy Lingelbach FUTURE HOME REALTY INC

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 around balcony off of the Kitchen and Den Area, and a Balcony off the living room and Primary Bedroom. Enjoy your favorite beverage from the Seventh floor balcony as you look out over the panoramic open waters of the Intracoastal

Kathy Lingelbach FUTURE HOME REALTY INC

503 The Ambassador Building at Bay Island – A Premier 55+Waterfront CommunityLocated in the highly sought-after Ambassador Building at Bay Island, this spacious fifth-floor two-bedroom, two-bath condominium offers approximately 1,230 square feet of comfortable Florida living in the heart of South Pasadena. Beautifully updated throughout, the condominium features a modernized kitchen with

Dean Doulou PIB REALTY

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 Gourmet attention, Stainless steel appliances, Granite counter tops and abundant cabinetry. Master Bedroom has a King size bed, walk in closet and ensuite bath with a walk in shower. 2bd Bedroom has a Queen size Bed and 2nd Bath has

Kathy Lingelbach FUTURE HOME REALTY INC

Harbourside Windwards Bldg Summer rental available. Updated, beach-themed, waterfront condo in Harbourside Community available April 21, thru October 31, 2026. Monthly rent is $3,000.00 and includes water, sewer, trash, basic cable, internet and $75 credit towards electric each month. This open floor plan unit is turn-key furnished, down to the linens and dishes. Master Bedroom has an updated

Kathy Lingelbach FUTURE HOME REALTY INC

***SPECTACULAR LUXURY CONDO on BAY ISLAND at the BOCA CIEGA BAY*** Life is Great when you’re living in Paradise at the meticulously maintained and gated community with 24/7 security personnel. This gorgeous FULLY REMODELED unit has 1300 square feet of open floor plan. As you walk in, you’ll be drawn to the Living Room and floor-to-ceiling window wall views of the community, on-site Marina and the

Stanley Chow DALTON WADE INC

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, convenience, and coastal charm—perfect for a short or long-term stay.Step inside this turnkey residence and feel instantly at home. The spacious layout is thoughtfully designed for both relaxation and functionality, featuring

Shawn Peacher NETWORK REAL ESTATE GROUP

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 55+ community in South Pasadena. This turnkey home offers true maintenance-free living with all utilities included. Inside, you'll find a bright, open living space with a coastal palette, and an updated kitchen featuring

Somer Tangorra CHARLES RUTENBERG REALTY INC