Weekly Rentals
“Lido Beach Hideaway “
Emerson Drive
3 Bedroom House
Lido Key -Weekly
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!
“Dolphin Dockside”
Cleveland Drive
3 Bedroom House
Lido Key -Weekly
Step into your private oasis featuring a heated pool and hot tub, perfect for unwinding after a day of exploring. The property boasts a dock that accommodates boats up to 48 feet, making it ideal for boating enthusiasts. Enjoy great fishing opportunities and frequent dolphin sightings right from your backyard. Quick walk to beach.
“Longboat Luxe”
2807 Inn on the Beach
2 Bedroom luxury Condo
South Longboat Key – Short Term
Dreaming of sunshine, beautiful sandy beaches, and warm turquoise Gulf waters? Your airy and bright 3-bedroom, 2-bathroom Longboat Key Beach paradise is ready to make that dream come true! Concierge on the Beach to set up your lounge chair or cabana! 8th floor views!!
Monthly Houses
“Club Estate “
Longboat Club Road
Ultra Luxury
Built 2025
5 Bedroom House
Longboat Key – Monthly
Behind the gates of the Longboat Key Club
Brand new home built in 2025
Experience ultimate luxury behind the gates of the Longboat Key Club at this newly built (2025) five-bedroom estate. Just one block from the beach, this high-end retreat features a screened-in pool area, outdoor kitchen, a a cozy outdoor fireplace for seamless indoor-outdoor living. Two upstairs balconies – including one with breathtaking Gulf views – makes it easy to soak up the Florida sunshine. With a spacious living area, a gourmet kitchen, and every amenity for relaxation and entertaining, this is Longboat Key Living at its finest.
“Dolphin Dockside”
Cleveland Drive
3 Bedroom House
Lido Key -Weekly
Step into your private oasis featuring a heated pool and hot tub, perfect for unwinding after a day of exploring. The property boasts a dock that accommodates boats up to 48 feet, making it ideal for boating enthusiasts. Enjoy great fishing opportunities and frequent dolphin sightings right from your backyard. Quick walk to beach.
“Ringmasters Retreat”
S Blvd of the Presidents
3 Bedroom house with pool and fenced yard
Lido Key Key – St Armand’s
Dr
Welcome to the Ringmasters Retreat – a spacious, family-friendly haven just steps from the vibrant St. Armand’s Circle! Enjoy your own private pool, fenced backyard, and endless fun with yard games and room to unwind. Perfectly located for exploring the Circle’s shops and restaurants or strolling to the beach, this home blends Sarasota’s charm with modern comfort and playful charm. Gather your crew and make every day a celebration at Ringmasters Retreat!
“Circle Modern “
Jackson drive
New Remodel 2025
4 Bedroom House
Lido Key Key – St Armand’s
Circle Modern is your newly remodeled retreat for 2025 (New Pictures soon), just a short stroll from St Armand’s Circle and the beach. Enjoy bright, contemporary interiors, a sleek kitchen, and inviting living spaces designed for comfort and relaxation. Whether you’re exploring Sarasota’s best shops and dining or unwinding after a day at the shore, Circle Modern is the perfect home base for your Gulf Coast getaway. 3 Bedrooms in main house plus a Casita with its own bedroom, bathroom and kitchenette.
“Lido Lookout”
South Polk
5 Bedroom House
Lido Key -Monthly
Experience the pinnacle of Lido Ley Luxury at the Lido Lookout. This extraordinary estate features a two-level pool, private dock, and a sunset rooftop terrace with panoramic views that will take your breath away. Entertain in style with spacious sunlight living areas and seem-less indoor-outdoor flow, or unwind in your own private oasis above the Gulf. With every high-end amenity and a location steps from the sand, this is the ultimate Sarasota getaway.
“Yardarm Dockhouse”
Yardarm Lanes
3 Bedroom house with pool and dock
Longboat Key Key – Country Club Shores
Yardarm Dockhouse offers relaxed canal-front living on South Longboat Key. Enjoy a private pool, spacious interiors, and a sunny patio perfect for unwinding or entertaining. With Boat lift for water adventures if that is your pleasure. Nearest street from Country Club shores to the deeded beach access. This retreat is ideal for families, friends and anyone seeking the classic Florida Lifestyle.
Month and Longer Condos
Beach Residences
Managed by Ritz Carlton
Membership Included
Lido Key -Luxury
Step into refined coastal living at The Beach Residences, where world-class Ritz-Carlton luxury meets the sugar sands of Lido Beach. Choose from premier 4-bedroom, 4-bath residences (3,800 sq. ft.) or a spacious 2-bedroom option, available for stays from one month up to 11 months. Each residence is elegantly appointed for comfort and style, featuring private balconies.
As our guest, you’ll enjoy exclusive membership access to the Ritz-Carlton Beach Club—complete with resort-style pools, fitness center, sauna, concierge services, and direct access to the beach. Whether you’re seeking a peaceful escape or a place to entertain, The Beach Residences offer an unparalleled Sarasota experience in luxury, privacy, and convenience.
Privateer
Gated Community
South Longboat Key – 90 days or longer
Experience the best of beachfront living at The Privateer, an exclusive community on the south end of Longboat Key behind the gates of the prestigious Longboat Key Club. Enjoy direct beach access and sweeping Gulf views, along with resort-style amenities including an Olympic-sized heated pool, tennis and pickleball courts, a fitness center, and a Gulf-side patio with fire pit and BBQ grills. With 24-hour secured lobby access, covered parking, and on-site management, The Privateer ensures both luxury and peace of mind. Whether you’re relaxing on your private balcony or exploring nearby attractions like St. Armands Circle and Lido Beach, The Privateer offers the perfect blend of comfort, sophistication, and relaxation for your Longboat Key getaway.
Beachplace
Gated Community
South Longboat – Gated
30 days or longer.
We have over 30 Listings here!
Experience the best of Longboat Key at Beachplace—a gated, resort-style community offering monthly beachfront rentals and an unbeatable coastal lifestyle. Guests enjoy direct access to the powder-soft sands, where complimentary chairs and umbrellas await, plus a sparkling pool, hot tub, tennis courts, fitness center, and clubhouse. Whether you’re relaxing by the water, staying active on the courts, or unwinding in beautifully appointed condos, BeachPlace is your home for comfort, convenience, and unforgettable Gulf Coast memories.
Choose from a variety of spacious, fully equipped condos—each professionally managed with personalized service to ensure your stay is seamless and relaxing. Discover why so many guests return year after year to Beachplace on Longboat Key..
The Pierre
Longboat Key – 90 days or longer
The Pierre is a prestigious, beachfront condominium community on Longboat Key, offering 66 luxury residences set across seven lush acres with direct access to a pristine sandy beach. Residents and guests enjoy an array of upscale amenities including a resort-style pool and spa, fitness center, tennis courts, and a stylish clubhouse, all within a secure, gated environment. With spacious floor plans, private balconies featuring breathtaking Gulf views, and attentive concierge-level services, The Pierre provides an ideal blend of comfort, elegance, and coastal living—perfect for those seeking a sophisticated, month-or-longer stay on Florida’s Gulf Coast.
Lido Towers
Lido Key – 30 days or longer
Lido Towers is a welcoming, resort-style condominium community ideally situated on Lido Key, just steps from the sparkling sands of Lido Beach and the vibrant shops and dining of St. Armands Circle. This gated mid-rise complex offers spacious one- and two-bedroom residences, each with private balconies perfect for enjoying Gulf breezes. Residents and guests enjoy amenities such as a heated swimming pool, hot tub, sauna, social room, and secure under-building parking, along with private deeded beach access. With a friendly atmosphere, tropical landscaping, and a prime location for beachgoers and culture lovers alike, Lido Towers is an excellent choice for a comfortable, extended stay on Sarasota’s beautiful barrier island.
Promenade
South Longboat Key – 90 days or longer
The Promenade offers an exceptional resort-style living experience on the coveted southern end of Longboat Key, directly along a pristine stretch of white sand beach. This gated community features 24-hour security, an in-building concierge seven days a week, and lush, park-like gardens with Har-Tru tennis courts, a gazebo, and a grill area perfect for gatherings. Enjoy one of the island’s largest swimming pools with a hot tub, recently renovated lobbies, well-equipped fitness centers, elegant club rooms, and garage-covered guest parking for added convenience. With a 90-day minimum rental policy, The Promenade is ideal for those seeking a luxurious, extended stay in an upscale beachfront setting.
Islands West
Longboat Key
Islands West is an upscale, beachfront condominium community located directly on the sands of Longboat Key, offering residents and guests sweeping Gulf views and resort-style amenities. With a three-month minimum stay, Islands West is perfect for those seeking an extended, luxurious escape. The high-rise condos feature spacious layouts and private balconies, while the property boasts a heated pool, tennis courts, fitness center, and private beach access—all within a secure, well-maintained environment. Its prime location and tranquil atmosphere make Islands West an ideal choice for anyone looking to enjoy the very best of Florida’s Gulf Coast living.
Club Longboat
Mid Longboat Key – 30 days or longer
Club Longboat is a vibrant, beachfront condominium community on Longboat Key, renowned for its active lifestyle and exceptional amenities. With a minimum one-month stay, guests and residents enjoy direct access to a beautiful stretch of sandy beach, along with two heated swimming pools, eight Har-Tru tennis courts, a fitness center, sauna, and clubhouse. Spacious condos feature private balconies or patios with Gulf or garden views, all within a secure, well-maintained setting surrounded by tropical landscaping. Club Longboat offers the perfect blend of relaxation and recreation, making it an ideal choice for extended stays on Florida’s Gulf Coast.
Seaplace
Longboat Key – 2 Month Minimum
Reserve your piece of paradise on Longboat Key. Seaplace is a 42 acre gated community of 461 maintenance-free condominiums. There are two mid-rise buildings, nine garden buildings and twelve townhouses. Seaplace is one of the most popular family beach complexes on Longboat Key. Two Month Minimum stays are required in this beachfront location.
Experience Luxury Living, Whether Short or Long Stays
Hear from our guests about unforgettable stays in Sarasota’s finest vacation homes.
“I have been staying her multiple times over the last few years. It is always perfect. Thank you Rick for being so responsive. I will keep recommending you to everyone.”
Sandy.
Vacation Renter – 3 month stay
“This condo is so clean and bright. So convenient to the Beach and Beachplace has every amenity you could imagine. We played pickleball and used the pool and beach almost every day. Easy access to St Armand’s and downtown as well. We will be back. “
Pat.
Winter Guest
“We spent February and March at Beachplace with a frontal view of the Gulf. There were endless sunsets. All of them different. We knew Beachplace well since we had owned a unit there for about 20 years. We were familiar with the pools, the gym, the pickle ball courts and more. The unit was well-equipped, light and easy to feel at home in.
Dealing with Rick was easy. From the beginning with all of the paperwork, to receiving necessary information upon arrival. There were no problems. When we had a few minor technical glitches in the beginning of our stay Rick was there immediately with hands-on help to resolve the issues. He was knowledgeable, pleasant, reliable and easy to deal with.
We would strongly recommend staying at Beachplace and doing business with Rick.”
Janet
Winter Guest
“Rick and Katie are excellent hosts and we would recommend them for any properties they represent. The home was very nice and suitable for families with children. Excellent location for beach, groceries, shopping and restaurants.”
James
Repeat Guest