A Guide to Our Properties on Anna Maria Island and Lido Key

At The Cottages on the Key, we take the utmost pride in our rentals. We offer the best vacation properties in SW Florida. While the majority of our inventory consists of vacation rentals in Siesta Key, we also have a great selection of amazing Lido Key & Anna Maria Island vacation home rentals where you can experience luxury, fun, and relaxation.

Our Lido Key Rentals

Discover the charm of Lido Key, a breathtaking barrier island off Sarasota’s coast in Florida. Known for its stunning beaches, crystal clear waters, and abundant wildlife, Lido Key is perfect for nature enthusiasts and adventure seekers. 

The area features the famed St. Armands Circle, offering upscale shopping and dining. Our Lido Key vacation rentals range from cozy beachside homes to luxurious waterfront villas, providing a blend of relaxation and indulgence for an unforgettable stay.

Coconut Cottage

Coconut Cottage on Lido Key is a delightful vacation rental perfect for a family or group getaway. It features three bedrooms and two full bathrooms, comfortably accommodating up to seven guests. The cottage is a sanctuary of relaxation with exclusive amenities, including a private heated pool and spa, an outdoor lounge area complete with HDTV, exterior heaters, a fire table, a dining area, and a ping pong table. 

Coconut Cottage is ideally situated for beach bums, as it is less than a two-minute walk from St. Armands Circle and a six-minute walk to Lido Key Beach. The cottage includes beach towels, chairs, a cooler, and a caddy to enhance your beach-going experience.

Inside, you’ll find a well-appointed space with two king beds, one queen bed, and a twin roll-away bed, all with linens provided. 

The home has a water filtration system, free WiFi, four Smart HDTVs with cable, a regular and Keurig coffee maker, dishwasher, washer, dryer, and kitchen essentials. Guests also have access to bicycles and kayaks for exploring the area.

Mermaids Oasis

Mermaids Oasis in Lido Key is a luxurious vacation rental offering a tranquil and indulgent getaway. The property features two bedrooms, two full bathrooms, and one-half bathroom, accommodating up to six guests. A highlight of this home is the private heated pool and hot tub set amidst lush tropical foliage, creating a peaceful retreat.

The home is just a five-minute walk to St. Armands Circle and a ten-minute stroll to Lido Key Beach. It boasts a king bed, a queen bed, a futon bed, and a queen sleeper sofa, all with provided linens. The screened-in lanai offers comfortable outdoor lounging space, and the gourmet kitchen is equipped with high-end appliances and a wine refrigerator.

Other amenities include kayaks, bikes, free WiFi, HDTVs, a regular and Keurig coffee maker, and a starter pack of toiletry and home essentials. Mermaids Oasis is designed for those seeking relaxation and adventure, providing a luxurious and convenient base for exploring the beauty of Lido Key.​

Sunset Heaven

Sunset Heaven on Lido Key is a stunning 4-bedroom, 3-bathroom waterfront home, ideal for up to 10 guests. Its standout feature is the breathtaking canal views. The property includes two master bedrooms, each offering unique and scenic vistas. One primary bedroom has direct access to a screened-in patio, while the other opens to a balcony overlooking the pool and canal.

Amenities include a private heated pool and spa, private boat dock access, a covered outdoor lounge area with dining space, and a ping pong table. It’s less than a two-minute walk from St. Armands Circle and less than a mile from Lido Key Beach. The house also offers free WiFi, HDTVs, various coffee makers, beach essentials, and a gas grill. 

Manatee Cove

Manatee Cove in Lido Key is a luxurious 4-bedroom, 4-bathroom waterfront vacation rental that accommodates up to 10 guests. It’s just a 30-second walk to St. Armands Circle and a 5-minute walk to Lido Key Beach. 

Each bedroom has its own bathroom, featuring high-quality linens and plush bedding. The private heated pool, outdoor bar, fire pit, and dining area provide exceptional outdoor entertainment. 

Additional amenities include kayaks, free WiFi, HDTVs, a variety of coffee makers, and a starter pack of essentials. Enhanced cleaning protocols ensure a clean and safe environment for guests​.

Our Anna Maria Island Rentals

Experience the allure of Anna Maria Island, a serene paradise in the Gulf of Mexico off Florida’s coast. Renowned for its pristine white sand beaches and tranquil turquoise waters, the island offers a perfect blend of adventure and relaxation. 

Our rentals on Anna Maria Island place you at the heart of this idyllic setting, ideal for swimming, fishing, boating, or simply soaking in the serene beauty. Each property is thoughtfully curated, ensuring a luxurious and comfortable stay that elevates your beach vacation to an exceptional experience.

Beach A La Mode

Beach A La Mode on Anna Maria Island is a 5-bedroom, 4.5-bathroom canal-front property, perfect for eight guests. It features a private heated pool, spa, boat dock, and rooftop with water views. 

Located just a 7-minute walk from Bayfront Park, the house includes multiple balconies with loungers, a game room, and a poolside dining area. The bedrooms offer two king, two queen, and four twin beds with linens. Other amenities include an outdoor shower, ping pong table, free WiFi, and HDTVs.

Salty Sister

Salty Sister, located on Anna Maria Island, is a 4-bedroom, 4-bathroom luxury vacation home with eight guests. It offers incredible ocean views and a prime beachfront location just steps from the beach. 

The home is a 10-minute walk to Pine Avenue and features a private heated pool and a spacious outdoor lounging area. The newly renovated property includes modern furnishings, an open layout, and a private balcony in the main bedroom with ocean views.