Remarks: Available for 6-12 months lease starting May 2026! Waterfront furnished 2 bedroom 2 bath condo located within minutes to the beach in resort-style gated community of Harbourside. Enjoy exclusive location on a private island with 24 hr manned security gate and extensive list of amenities. Rent includes water, cable, Wi-Fi, and full access to: pools, jacuzzi, his-and-her fitness centers, sauna, tennis, pickleball, shuffleboard courts, and a billiards room. A washer and dryer are conveniently located inside the unit. The unit also comes with an assigned garage space. Residents enjoy access to car wash stations (with vacuum and air) as well as electric vehicle charging stations. Sorry, no pets per HOA rules. For outdoor enthusiasts, the beach is just a 5-minute drive away, or enjoy a scenic 1.5-mile waterfront walking trail—perfect for spotting dolphins, launching a kayak, or fishing along the seawall. Boat slips may be available for rent. Condo offers magnificent views of the Intracoastal and the Gulf from an expansive balcony accessible from both the living room and the primary bedroom. Storm shutters provide added peace of mind. The spacious bathrooms include a walk-in shower in the primary suite and a tub in the guest bath. Experience the best of Harbourside living at an affordable price! Tenant application $100, background check required.

Listing is courtesy of: LUXURY & BEACH REALTY INC (727-800-5906)

Listing Agent: Maria Koziakov (727-748-9200)

Remarks: Welcome to Pasadena Cove, a stunning waterfront gated community in the heart of South Pasadena. This beautiful Two-bedroom Two-bathroom condo is fully furnished, and all housewares included with 1 carport. The kitchen has wood cabinets, a large pantry, Corian countertops, tile backsplash and breakfast nook. Ally kitchen layout with pass-through to dining and living room. Off the living room are sliding glass doors to a screened-in balcony with breathtaking views WATERFRONT of Boca Ciega Bay. High ceiling all throughout, plenty of closet space and full-size washer & dryer. This condo is a split floor plan with a huge master bedroom (king size bed) with walk-in closet, large windows with a gorgeous view, and private access to the balcony. Master bathroom has stand up shower. The 2nd bedroom (queen size bed) and 2nd bathroom has stand up shower located on the 4th floor (elevators in building) with an assigned covered carport. Rent Includes: All furniture, housewares, Cable TV, Electricity, Internet, phone, Water, Sewer, Trash and 1 assigned carport and visitor parking. Min lease is 3 months and No pets allowed. Pasadena Cove amenities have a waterfront heated pool, Spa, a beautiful clubhouse with a full kitchen, and social activity, Billiard room, fitness center, Shuffleboard courts. Boat/ trailer parking available and private marina where DEEP WATER BOAT SLIPS can be rented or purchased as available. with immediate access to Boca Ciega Bay, Tampa Bay, and the Gulf Coast. Pasadena Cove has a private pedestrian gate that provides immediate walking access to shopping and other essentials. AMAZING LOCATION only 1.5 miles from ST PETE BEACH and 3 miles from TREASURE ISLAND. Downtown St. Petersburg is a 15-minute drive or take the Sun Runner express bus. a mile, minutes to Gulfport and Downtown St Petersburg, shopping, restaurants, hospitals, and much more.

Listing is courtesy of: ELITE TAMPA BAY REALTY LLC (844-354-8373)

Listing Agent: Debbie Hebden (786-942-8280)

Remarks: Super Complex with loads of amenties. Gated. Walking path around the whole island. Unit is newly furnished in Deccember. Available for May 15st occupancy. 2 month minimum. Lower rate available for off season longer term. Nice large 1 bedroom unit. Big bedroom and living/dining. Great waterview and balcony overlooking the bay. Covered parking included.

Listing is courtesy of: COASTAL PROPERTIES GROUP (727-493-1555)

Listing Agent: William Welch (727-448-2175)

Remarks: Rare, hard to find 2 bed 2 bath UNFURNISHED corner wrap around balcony with sunset water views. This condo is located in a 55 Plus gated waterfront community. It comes with Covered parking and a washer/dryer. All new flooring, move in ready. Breath taking views of Boca Ciega Bay and Harbourside Marina. There is also a gated courtyard entry. This unit is unfurnished and is available for long term lease. Very small pet is ok. No smoking allowed. Must be 55 or older. Perfectly placed Covered Carport. Beaches less than 5 min away. Shopping and dining close by. There is a large community clubhouse with billiards, ping pong, card room, library and his/hers fitness center, 1.25 walking trail, tennis, pickle ball, shuffleboard courts. Available May 10, 2026

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-828-8615)

Listing Agent: Joe Nix (727-687-0555)

Remarks: Available May - Dec 2026. 30 day minimum stays required. Welcome to your waterfront retreat on Florida’s sunny Gulf Coast! Nestled in the coveted Hemingway Condos, this beautifully updated vacation home or mid-term rental is just what you’ve been looking for. Foremost, you’ll love the breathtaking views from your private 4th floor balcony. Spend each morning sipping coffee while watching boats float by or enjoy an evening cocktail at sunset. The island life you crave is within reach. Step inside, and you’ll notice the attention to detail throughout. Clean lines and modern comforts merge with coastal decor to create a feeling of peace and quiet luxury. You’ll appreciate the well-appointed kitchen with sleek finishes, updated appliances, and fully-equipped for easy meal-prep. An open floor plan makes conversation easy, but be warned, the stunning water views may prove a distraction to productivity. Dining and living room also embrace open-concept living, and boast both comfort and coastal elegance. Wherever you find yourself, sweeping water views await. At the end of a sun-filled day, your spacious primary bedroom provides a tranquil escape with en suite bathroom, remodeled walk-in shower and washer/dryer. Hemingway Condo guests will love the luxurious, heated pool and hot tub which overlooks intracoastal waters. There is even a launch point for kayaks or SUP. Ready to venture further? St Pete Beach as well as Downtown St Petersburg are close by and full of opportunities. The former, offers vibrant beach bars, boat rentals, and miles of pristine sand, all with a laid back, Jimmy Buffet style vibe. The latter, downtown St Petersburg, boasts 5 star dining, museums, live theatre, shopping and waterfront strolls along the Tampa Bay. Truly the best of both worlds and all within easy reach. Overall, this exceptional condo is a perfect blend of comfort, style, and location. Don’t miss your chance to discover Hemingway & The Sea!

Listing is courtesy of: PINK CHAIR REALTY (407-212-5358)

Listing Agent: Kelly Strom (407-212-5358)

Remarks: 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 renovated two-bedroom, two-bath residence comes fully furnished and equipped, making it truly move-in ready. The sleek modern kitchen features quartz countertops and a breakfast bar, ample cabinetry and counter space perfect for casual dining, tile flooring and beautifully updated bathrooms carry a clean, contemporary feel throughout. Bright, open living spaces fill with natural light and capture sweeping water views of Boca Ciega Bay from your private screened balcony. The spacious primary suite offers a peaceful retreat with beautiful water views, while the comfortable guest room provides flexibility for visitors or a home office. Hurricane-impact windows and sliders add peace of mind and energy efficiency, and an in-unit laundry closet adds everyday convenience. One small dog or cat may be considered at the landlord's discretion with association approval. Enjoy resort-style living with Bay Island's exceptional amenities, including multiple pools, tennis and pickleball courts, fitness centers, and a scenic waterfront walking path—all just five minutes to famous St. Pete Beach and 15 minutes to vibrant downtown St. Pete, with dining and shopping nearby. Available for long-term rental at this rate.

Listing is courtesy of: COLDWELL BANKER REALTY (727-360-6927)

Listing Agent: Maria Mercado Herbert, Pa (727-642-1151)

Remarks: 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 renovated two-bedroom, two-bath residence features luxury vinyl flooring, a sleek modern kitchen with quartz countertops, and beautifully updated bathrooms throughout. Bright, open living spaces are enhanced by additional corner-unit windows, filling the home with natural light and capturing sweeping water views of Boca Ciega Bay from your private screened balcony. The spacious primary suite offers a peaceful retreat, while the light-filled guest room provides comfort and flexibility for visitors or a home office. Hurricane-impact windows and sliders add peace of mind and energy efficiency, and an in-unit laundry closet adds everyday convenience. One small dog or cat may be considered at the landlord’s discretion with association approval. Enjoy resort-style living with Bay Island’s exceptional amenities, including multiple pools, tennis and pickleball courts, fitness centers, and a scenic waterfront walking path—all just five minutes to famous St. Pete Beach and 15 minutes to vibrant downtown St. Pete, with dining and shopping nearby. Available for long-term rental at this rate.

Listing is courtesy of: COLDWELL BANKER REALTY (727-360-6927)

Listing Agent: Maria Mercado Herbert, Pa (727-642-1151)

Remarks: 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 appliances, a custom granite backsplash, and solid wood cabinetry—perfectly blending style and functionality. The open-concept floor plan allows for effortless flow between the kitchen, dining, and living areas, all enhanced by abundant natural light. The primary suite is a peaceful retreat featuring stunning water views, a private ensuite bath, and the convenience of an in-unit washer and dryer. A generously sized second bedroom and full bath provide comfortable accommodations for guests or additional living space. Step out onto the covered balcony and unwind while taking in tranquil views of Boca Ciega Bay—an ideal setting for morning coffee or evening relaxation. Additional highlights include Hurricane proof windows, assigned covered parking, separate storage, and ample guest parking for visitors. Bay Island offers an exceptional lifestyle with an array of resort-style amenities, including separate men & women's gym, a social club with a variety of events throughout the year, 6 heated pools, 2 hot tubs, tennis courts, shuffleboard, and boat docks. This community is also pet-friendly, adding to its welcoming atmosphere. Ideally located just minutes from St. Pete Beach, vibrant downtown St. Petersburg, and an easy drive to Tampa, this is coastal living at its finest.

Listing is courtesy of: KELLER WILLIAMS ST PETE REALTY (727-894-1600)

Listing Agent: Jac Smith (727-228-1777)

Remarks: 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 a bright living area, a fully equipped kitchen, dual office workspaces, and comfortable bedrooms that make extended stays effortless. Wake up each morning to serene bay views and enjoy your coffee from the comfort of your private space overlooking the water—your own peaceful slice of paradise. This FULLY FURNISHED TURNKEY unit is ready now! This tastefully decorated home features KING BEDS IN BOTH BEDROOMS (an ADJUSTABLE king bed in the master), walk-in closets, stainless steel appliances, flat screen TVs, a pull-out sofa bed with brand new queen mattress, CABLE, HI-SPEED INTERNET (with WiFi), and laundry INSIDE of the unit! Flat-screen TVs in both the master bedroom and living room and a full 2nd bathroom for your guests! Enjoy the gorgeous views of the Bay from your screened in lanai! Comes with an assigned, covered parking spot and a ton of wide-open guest parking for your visitors! Located in the sought-after Bay Island community (a 55+ community), guests enjoy a secure, well-maintained environment with beautifully landscaped grounds and a welcoming atmosphere. The community offers fantastic amenities, including 6 community pools, (including a sparkling waterfront pool), dual hot tubs, tennis, pickleball, fitness center, marina, tiki huts, gas grills, billiards, ping pong, clubhouse, and walking paths—perfect for soaking in the Florida sunshine or staying active during your stay. You can’t beat the location! Just minutes away, you’ll find the pristine white sands of Treasure Island and St. Pete Beach, consistently ranked among the best beaches in the country. Spend your days swimming, sunbathing, or enjoying breathtaking Gulf sunsets. For dining, shopping, and entertainment, you’re a short drive from vibrant Downtown St. Petersburg, where you can explore waterfront parks, art galleries, museums, and a lively restaurant scene. Don’t miss a visit to the renowned Salvador Dalí Museum or a stroll along Beach Drive. Sports fans and event seekers will love being near Tropicana Field, home of the Tampa Bay Rays, while nature lovers can explore nearby parks, boating opportunities, and scenic coastal trails. Whether you’re relocating, working remotely, or simply looking for an extended getaway, this waterfront condo offers everything you need—comfort, convenience, and an unbeatable Florida lifestyle. Come experience the best of bayfront living and make your stay truly unforgettable! ALL UTILITIES INCLUDED IN RENT! Leases 6 months or less are subject to 13% sales/vacation tax. Summer rental rates: (MAY - NOVEMBER): $2,900/month. DECEMBER: $3,500/month. In-Season rental rates: (JANUARY – APRIL): $4,900/month. AVAILABLE for 2026: April, May, June, July, August, September, October, November, December. AVAILABLE for 2027: January, February, March, April, May, June, July, August, September, October, November, December. Don't wait, this unit won't last! Gorgeous condo in one of the most sought-after communities in the area! Association approval is required ($150). Tenant is responsible for a 1-time move-out cleaning fee of $175.

Listing is courtesy of: NETWORK REAL ESTATE GROUP (941-803-0344)

Listing Agent: Shawn Peacher (703-405-2615)

Remarks: 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, living room combination. This unit is completely updated with a retractable screen and storm shutters on the balcony right off the beautiful canal. All new appliances and it even has a wine/beverage fridge built in the the breakfast bar. Bay Island is one of the premier resort communities in the area. It is a gated community that has a his and hers gym, billiards room, ping pong room, car wash stations, tennis/pickleball courts, gas grills, several pools and spas. There is a very active social program at the club house if you choose to participate. Fire Place and stools do not stay.

Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)

Listing Agent: Jane Freel (727-410-6205)