Siesta Key, FL Homes for Rent in a Senior Community

Live the Siesta Key lifestyle in this beautifully updated 2-bedroom, 2-bath residence offering approximately 1,600 sq ft of usable living space, tucked inside one of the island’s most desirable 55+ Gulf-front communities, just a short stroll to Siesta Key Village. The additional square footage comes from a fully finished garage complete with A/C and a built-in Murphy bed, creating the perfect

Curtis Ware KW COASTAL LIVING III

This property is a 30 night minimum.This 2 bedroom, 1 bath is a second floor garden unit on the bay side of Midnight Pass, and is approximately 15 yards from the Intracoastal waterway.The master bedroom has a queen bed and a 40 inch TV. The master bathroom has a tub/shower combination with a sliding glass door.The guest bedroom has 2 twin beds, a ceiling fan, and window with natural

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Starting at $179/night! Step into your perfect beach getaway with this charming ground-floor 1-bedroom unit located in the sought-after Casa Mar complex, just off Midnight Pass Road and only steps from the sand. Relax on the screened lanai overlooking a peaceful courtyard, where two sparkling pools invite you to unwind in the Florida sunshine. A short stroll along the sidewalk brings you directly

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Starting at $179/night! Step into luxury and comfort at our newly renovated 2-bedroom, 1.5-bathroom condo, perfectly designed for your next getaway. This vibrant space features a fully equipped kitchen ready for your culinary adventures and a private carport just steps from the unit for hassle-free parking. Recently updated in Summer 2023, the condo comfortably accommodates up to six guests with

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Starting at $179/night. Discover a luxurious 1-bedroom, 1-bathroom condominium at Casa Mar, where comfort and style meet just steps from the beach. The spacious primary suite features a king-sized bed, while the fully equipped kitchen flows seamlessly into a generous dining area and inviting living room, perfect for relaxing or entertaining. Step outside to enjoy a screened-in lanai furnished

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Still available for season January - April 2026l! Two bedroom 2 bath ground floor with view of the Gulf. Step outside and your on the sand! Escape the winter and be on the beach. Located in the heart of Siesta Key’s most desirable area, this property offers exceptional appeal with being just steps from the world-famous powdery white sand beach. Siesta Key Village is within easy walking distance,

Maureen Plichta STRINGER MANAGEMENT INC

Available for season 2027! This 2 bedroom 2 bath villa with easy ground floor entry features tile flooring in the main living areas and plush new carpeting in the bedrooms. The stylish galley kitchen has been fully updated with custom white cabinetry, granite countertops and backsplash, recessed lighting, and brand-new GE appliances, perfect for preparing meals after a day at the beach.Enjoy

Maureen Plichta STRINGER MANAGEMENT INC

55+ Harbor View Haven on Siesta Key w/beach access!Discover relaxation and adventure at our Siesta Harbor condo on Siesta Key. This bright 2 bedroom unit offers modern comfort and stunning harbor views from the screened porch. Enjoy deeded beach access and watch breathtaking sunsets. You'll have access to amenities like a fishing pier, boat slips, a pool, and clubhouse activities. Whether

Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

BEAUTIFUL WATERFRONT CONDO ON SIESTA KEY AVAILABLE NOW AND the month of January! CANAL VIEW • BEACH ACCESS • BOAT SLIPS UPON AVAILABILITY - REASONABLY PRICED. Now available In Season and as an annual Rental! Private, beautifully furnished condo with a gorgeous view of the Harbor and Sailboat Water Canal in Siesta Harbor. Enjoy water views of the canal from your enclosed balcony and just a

Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

Available now until 4.4.26. 55+ community. Welcome to your dream coastal escape in beautiful Siesta Harbor on Siesta Key! This turnkey furnished; spacious one-bedroom, two-bath condo is available now through October 2025. Perfectly situated along a peaceful canal, it offers stunning water views and a truly relaxing atmosphere. Just a short stroll away, you'll enjoy deeded access to Siesta Key's

Jonathan OSteen O'STEEN GROUP INC

BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available May through December 2026! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed hurricane glass lanai,

Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

This stunning one-bedroom, two-bathroom condo in Siesta Harbor in the Tarpon Building is the perfect combination of luxury, convenience, and breathtaking views. Located in a prime location, boating access, canal frontage, and mesmerizing Intracoastal Waterway views. Step inside and be captivated by the modern elegance of this home. The kitchen is a chef's dream, featuring stainless steel

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new stainless steel appliances, granite countertops, remodeled bathrooms and nice décor. King bed in master bedroom, two twins in second bedroom. One month minimum rental. This over 55 community is ideal for your island beach vacation. Enjoy a cocktail or your morning coffee from the

Kay Esposito SIGNATURE REALTY ASSOCIATES

Available January to April 1, 2026! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Harbor and the Intracoastal Waterway - rarely available! Fifty-five+ community. Easy walk to deeded beach access to Siesta Key, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Saunas, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta Harbor

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

Immaculate End Unit in the Marlin building, Ready for you to Enjoy through January 2026 and April 2026 through year-end 2026! Stunning all the way, Great Location in the complex, close to the pool, clubhouse, spa, sauna, 2 bedroom 2 full baths, enclosed lanai overlooking the canal, steps to Deeded beach access through Crescent Arms, for your pleasure daytime or sunset time! Siesta Harbor offers a

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

Siesta Key vacation rental! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open

Margaret Young JENNETTE PROPERTIES, INC.

This 2 bedroom, 2 bath condo in this popular 55+ community, is conveniently located on the ground floor next to the club house and swimming pool, and features new appliances, granite counter tops and ceramic flooring. Queen size bed in the Master with a full wall length closet for guests. The walk-in closet is reserved for the Owners. The guest bedroom has 2 single beds that can be combined to

Margaret Young JENNETTE PROPERTIES, INC.