Houses for Rent in Longboat Key, FL

Embrace coastal living in this expansive 4-bedroom, 3-bath home boasting over 4,200 sq. ft. of elegant space. Experience natural light through walls of windows in the open living area with vaulted ceilings. The gourmet kitchen, equipped with stainless steel appliances and a curved island, showcases breathtaking Gulf views. Enjoy a private pool, generous patio, and direct beach access. The primary suite features a private balcony and spa-style bath, adding luxury to everyday life.

Nestled in a serene fishing village, this elegant one-bedroom cottage features vaulted ceilings and a contemporary kitchen. Enjoy high-speed internet, in-unit laundry, and exclusive boat parking. With Whitney Beach just a short stroll away, this charming retreat combines island charm with modern comfort, perfect for couples seeking a peaceful seaside getaway.

Immerse in history and elegance at this fully rebuilt coastal home in Historic Longbeach Village. This turnkey 3-bedroom, 2-bath residence features vaulted ceilings, a gourmet kitchen with quartz countertops, and spa-like bathrooms. The serene backyard boasts a lily-pad pond and fire pit, while the prime location allows easy access to beaches and waterfront dining. Enjoy modern amenities along with the charm of its historic roots, perfectly suited for personal use or vacation rentals.

This beautifully updated 4-bedroom, 2-bathroom home features new appliances, cabinetry, and flooring throughout. With 1,280 square feet, it combines modern comfort with historic charm. Lawn maintenance is included, and there's convenient in-unit laundry. Enjoy the close proximity to stunning beaches, vibrant dining, and shopping options, making this residence perfect for the Gulf Coast lifestyle.

This stunning 3-bedroom, 3-bathroom house offers 2,045 sq ft of luxurious living in Country Club Shores. Enjoy the serene ambiance with central air, a deck, and a refreshing pool. Included utilities such as cable, internet, and water make for stress-free living. Perfect for seasonal rentals, available for select dates in late 2026 and early 2027. Embrace the ultimate Florida lifestyle in this exquisite property!

Experience Florida living in this exquisite three-story home, fully furnished for a comfortable stay. Spanning 3,310 sq ft, this rental features ample storage, a private pool surrounded by lush landscaping, and is just a short 3-minute walk to Gulf beaches. Perfect for sun-seekers and those who appreciate a serene outdoor oasis. Ideal for a year-long lease, this property offers the perfect blend of luxury, convenience, and relaxation.

Experience the ultimate in coastal living in this annual rental at The Residences at The St. Regis. This furnished 1-bed, 2-bath residence spans 1,721 sq ft, showcasing soaring ceilings and breathtaking views through floor-to-ceiling sliding glass doors. The gourmet kitchen features high-end Wolf and Sub-Zero appliances, while the elegant owner’s suite includes a spacious walk-in closet and luxurious bath. Enjoy resort-style amenities including pools, spa, fitness center, and private beach access.

Embrace the island lifestyle in this beautifully updated 2-bedroom, 2-bath home with a den, featuring a 20,000-pound boat lift and private heated pool. Perfect for boaters, the property includes hurricane-impact sliders, lush landscaping, and deeded beach access just steps away. An open-concept kitchen with a quartz island complements the upscale finishes throughout. Enjoy the convenience of being in a sought-after community, ideal for both long-term and seasonal leases. Pets welcome!

Experience breathtaking Bay and Marina views in this beautifully furnished 1-bedroom, 1-bath villa in a serene 55+ community. Renovated with a beachy vibe, the airy great room features an open layout with ample sunlight. Enjoy private deeded beach access just a short stroll away, along with a refreshing pool. The spacious bedroom includes a walk-in closet, making this maintenance-free retreat the perfect spot to embrace the Longboat Key lifestyle.

Embrace beachside living in this stunning 4-bedroom, 3.5-bath luxury home. Spanning 2,292 sq ft, it offers direct access to Sarasota Bay and deeded beach access just a short stroll away. The screened patio features a family-friendly heated pool, perfect for endless summer fun. Enjoy outdoor dining beside the gas grill while watching the sunset. Located just 2 miles from St. Armand’s Circle and 4 miles from downtown Sarasota, this home blends relaxation with vibrant local attractions.

Experience luxury living in this beautifully renovated 3-bedroom, 3-bathroom home boasting 3,230 sq ft of space. Features include a modern kitchen with new appliances, an inviting heated pool, and a hot tub. Perfect for boating enthusiasts, it offers a brand new boat dock and lift, plus private beach access just across the street. Enjoy breathtaking views of the wide canal from the main sitting area, making it an ideal retreat for family and friends.

Embrace the coastal lifestyle in this stunning 3-bedroom, 3.5-bath waterfront home boasting direct water access and a private dock, perfect for boating enthusiasts. Two floating jet ski docks add to the allure. Enjoy serene water and lush golf course views while being secure with hurricane-rated doors. Spread across 3,101 sq. ft., this residence captures the essence of Florida living with both luxury and tranquility.

Experience a luxury getaway in this stunning 5-bedroom, 5.1-bathroom home. Spanning 4,858 sq ft, this thoughtfully designed residence features state-of-the-art kitchen appliances, granite countertops, and spacious living areas. Enjoy the screened lanai overlooking the canal, or take a short stroll to the private deeded beach. Ideal for relaxation and recreation, this home is close to golf courses, boutique shopping, and outdoor activities like biking and boating.

Enjoy coastal living in this newly renovated 2-bedroom, 2-bath waterfront villa that offers breathtaking full-bay views. This turnkey furnished gem features a spacious layout, perfect for a tranquil lifestyle. Steps from the Intracoastal Waterway and close to your deeded beach access, experience the best of island living. The vibrant Spanish Main Yacht Club community adds to the charm with a heated pool and clubhouse amenities, all within minutes of downtown shopping and dining.

This tropical retreat accommodates up to 9 guests, featuring a lush garden, a sparkling heated pool, and a spacious screened lanai for outdoor relaxation. The stylish chef's kitchen boasts premium appliances, including a Wolf range, and the newly updated bedrooms provide comfort with a king bed in the primary suite and fun bunk beds in the kids' room. Just a short stroll from Whitney Beach and local dining options, this home is perfect for unforgettable family getaways.

Experience luxurious living in this stunning 4-bedroom, 3.5-bathroom home, boasting breathtaking canal views and direct access to Sarasota Bay. The spacious layout includes a gourmet kitchen, a dedicated office, and a bonus room, perfect for relaxation and productivity. Enjoy your private heated pool and spa, surrounded by beautiful landscaping. This residence features an 11,000 lb boat lift, making it a true boater’s paradise, all just minutes from pristine beaches and upscale dining.