Vacation Rentals

NEW PROPERTY Welcome to 440 Cleveland Drive, a stunning, fully renovated rental property on Lido Key where luxury meets coastal charm. Completed in March 2025, everything inside and outside this home is brand new! Nestled on a canal off the Intracoastal Waterway, this Lido Key 3-bedroom, 3-bathroom retreat offers a perfect blend of modern amenities and serene waterfront living. Whether you're here for relaxation or adventure, 440 Cleveland Drive has…...

Bring the whole family as this home features 3 bedrooms and 2 1/2 baths. This very spacious home is almost 2,600 square feet with plenty of room to relax. Huge open living area. You will love the fenced backyard featuring multiple seating areas and a pool to relax in. Portable putting green and safe ax throwing. Lot's of space. It is steps away from the world famous St. Armand's circle…...

NEW PROPERTY Dreaming of sunshine, beautiful sandy beaches, and warm turquoise Gulf waters? Your airy and bright 3-bedroom, 2-bathroom Lido Beach paradise is ready to make that dream come true! Located at 180 Emerson Drive, Sarasota, FL, this charming home is available now for weekly rentals. Situated on a fully fenced corner lot, this one-level home offers easy access and is directly adjacent to North Lido Beach Park. With a…...

Welcome to Privateer North 305, an exceptional beachfront condo located on the prestigious south end of Longboat Key, behind the gates of the exclusive Longboat Key Club community. This beautifully appointed unit offers breathtaking Gulf and sunset views from not one, but two private balconies. Whether you're looking for a tranquil retreat or an active beachside lifestyle, this property has it all. Amenities Privateer North 305 is designed for comfort…...

Short Term Stays available Imagine waking up to a breathtaking panorama of the Gulf of Mexico,. This completely remodeled condo, the largest in the community, offers unobstructed, 8th-floor views that will take your breath away. Picture yourself stepping onto the expansive terrace and feeling the cool Gulf breeze as you witness the nightly spectacle of a fiery sunset. Inside, immerse yourself in a world of coastal contemporary elegance. Every detail,…...

Immerse Yourself in Luxury at this Waterfront Oasis: Picture yourself stepping into a spacious 5-bedroom haven (4,617 sq ft!) with a private entrance, offering unforgettable experiences for the whole family. This luxurious beach home boasts spectacular views from four private balconies, a rooftop deck with 360-degree panoramas, and a two-level pool and spa with a covered deck, bar, and outdoor TV - perfect for entertaining under the Florida sun. Unwind…...

Winter booking available. Ritz Carlton GOLD membership included. Enjoy convenience to Ritz managed amenities as you step off your private balcony "walk-down" onto the fire-pit and pool deck. This is the only condo in the entire building with this convenient feature. The building is premium as a Ritz Carlton-managed property! This like-new condo residence offers Travertine floors in the spacious main living areas. The Kitchen is designed for a true…...

Located directly on a Canal with a boat lift available for use. This is a single family home that contains 2,192 sq ft and contains 3 bedrooms and 3 bathrooms and a private swimming pool. Dining room has views to the water. Canal connects directly to the Bay and the neighborhood is located on the southern end of Longboat Key, convenient to St Armand's Circle and Sarasota. Bring your boat…...

Spacious 2 bedroom condo in Beachplace gated complex. King in Master bedroom. Come enjoy your time at the Beach. This is a great condo for you to call home for a month or more. Condo is meticulously clean and well cared for. Owners have upgraded the furnishings including large smart TV's One month Minimum. The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate. •…...

Experience Coastal Elegance at Beachplace Penthouse Welcome to your dream beachfront retreat, where coastal living meets luxury at its finest. Nestled on the coveted sixth-floor Beachfront corner of Beachplace building 8, this beautiful penthouse offers an unparalleled living experience with breathtaking panoramic views of the pristine beach, the shimmering Gulf of Mexico, and mesmerizing sunsets that paint the sky year-round. Step onto the expansive wrap-around balcony and let the gentle…...

Immerse yourself in beachfront bliss at Lido Bliss: Imagine stepping off the elevator into your private sanctuary. Breathtaking panoramic views of the Gulf of Mexico greet you from your expansive balcony, setting the scene for an unforgettable stay. This meticulously kept, 4-bedroom 3.5 bath haven exudes luxury with Stunning views from Gulf to Bay showcasing the stunning scenery. Awaken your senses with the sophisticated coastal décor and unique light fixtures,…...

Beautiful beachfront unit on the 5th floor with amazing beach and sunset views. 2 bedroom, 2 bath unit with many modern upgrades. Master bedroom has a king bed and second bedroom has two twins. The master bath is a walk-in shower. Second bathroom is tub/shower combo. Come make this your home for a month or more. 30 day rental required. It is located in Beachplace, which is a premier gated…...

2 Bedroom and 2 Bath condo located in the resort community of Beachplace Association. Faces the golf course with angled Gulf view and has access to the boardwalk to the Beach. Beachplace sets up chairs and umbrellas daily on the beach to make access very simple and inviting. This is a very bright and cheerful condo The master suite with a king bed offers lush views and access to the…...

2 Bedroom and 2 Bath condo located in the resort community of Beachplace Association. Faces the golf course with limited Gulf view and has access to the boardwalk to the Beach. Beachplace sets up chairs and umbrellas daily on the beach to make access very simple and inviting. All NEW furnishings throughout this pristine condo with large tv in living room. The master suite with a king bed offers lush…...

Live life on the beach---Private parking included! Beachplace is one of Longboat Key's premier vacation rental locations on the island! With amazing direct Gulf-front views, this sophisticated and chic 4th floor condo with balcony has it all! This condo has modern updates throughout including upgraded kitchen and bathrooms and hardwood flooring in living and dining areas. The Large master bedroom has a King bed, an en-suite bathroom with a walk-in…...

Penthouse level fully renovated 2 bedroom condo offers modern luxury. It is paradise within paradise. This is a very rare find. Beachplace is one of Longboat Key's premier vacation rental locations on the island! With amazing direct Oceanfront views, this top floor unit boasts a double balcony. This condo has it all including 2 bedrooms each with a King bed. It is freshly renovated and ready to be your home-away-from-home…...

Beautiful Beachplace beachfront unit on the 3rd floor spectacular Gulf and beach view. Has brand new windows and doors and is an end unit in building 3 with glass sliding doors on 2 walls of the living room. This is the closest building to the pool. It has 2 parking spaces. One is covered. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades and a very open feel.…...

3 Bedroom and 3 Bath condo located in the resort community of Beachplace Association. Faces the golf course and has access to the boardwalk to the Beach. Beachplace sets up chairs and umbrellas daily on the beach to make access very simple and inviting. End unit with lots of light in the living space with 2 sets of sliding doors. The master suite offers lush views and access to the…...

Exquisite beach and Gulf view unit on the 3rd floor of building 3. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. New owner has upgraded unit including tiling, furniture replacement, painting, new kitchen appliances, new linen, TV's and more. This condo also has new windows and doors. This is a new and bright condo ready for your beach adventure. Condo is located in the Gated Beachplace complex…...

Come enjoy the Beach - Private parking included. Beautiful beachfront unit on the 3rd floor with a Beach and Lake view. Beachplace Building 3 unit 304. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. A beautiful unit with shiplap wall in living room and master bedroom, great flooring throughout, beautiful walk in shower and a view that will keep you on the balcony full time. This one…...

Penthouse unit on the top floor of building 3 at Beachplace. Top floor units enjoy a double balcony with access from the living room and Master bedroom. Amazing views of Beach, Pool, Pond and downtown Sarasota.This is a very popular floorplan at Beachplace. You have spectacular views of the beach and Gulf of Mexico to the right and the Bay and downtown to the left. Look no further as this…...