Condo vacation rentals in Lido Key

A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.

5.0 out of 5 average rating, 172 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to Mi Casa Siesta on Siesta Key, the #1 beach in the country! Gorgeous newly renovated one-bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

Superhost

A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.

4.88 out of 5 average rating, 146 reviews

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

A three-story condominium building is shown, featuring a combination of palm trees and lush green landscaping at the forefront. Balconies are visible on each level, with a red-tiled roof adding a distinct character to the architecture.

4.96 out of 5 average rating, 125 reviews

Seaside on Siesta Key Beach

Seaside on Siesta is the perfect walkable location to everything you need for a seaside getaway! Located directly across the street from Siesta Key Beach. Walk or take the FREE trolley (trolley stop located feet from our front patio) to Siesta Key Village, Stickney Point, or Turtle Beach First floor unit so no need to wait on elevators. The spectacular white quartz beach and crystal clear water awaits you just outside your door! Search "Seaside on Siesta Tour" on Youtube for a video tour.

4.79 out of 5 average rating, 109 reviews

Beachwalk Townhouse with view of Gulf of Mexico

Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

4.85 out of 5 average rating, 110 reviews

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

A serene pool area is bordered by palm trees, reflecting the gentle hues of a sunset. Lounge chairs are arranged around the pool, and a shaded cabana is visible in the background. The tranquil water mirrors the evening sky, enhancing a peaceful atmosphere.

4.97 out of 5 average rating, 137 reviews

Heated Pools & Spa · Private Beach + Bay Views

Perfect for family and group beach stays, with reliable Wi-Fi and a dedicated workspace for flexible remote work. This oversized renovated 2‑bed, 2‑bath condo sleeps six: a king in the master and two queens in the second bedroom; both bathrooms serve the group for privacy and convenience. Enjoy full gulf-to-bay living with private beach access and supplied chairs, umbrella, cooler and wagon, plus two heated pools, a heated spa, gym, courts, bay views, free parking and keypad self check-in.

4.98 out of 5 average rating, 253 reviews

A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.

Condo in Longboat Key

Island Time!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

4.94 out of 5 average rating, 154 reviews

The Flamingo's Nest at Sea Club II

The Flamingo's Nest at Sea Club II features a beautiful new pool on the intracoastal waterway, a tiki hut for on-site cocktail hours, a plethora of boats and sea birds to enjoy while cooking on our new charcoal grills, a fishing pier, boat basin, and private beach access directly across the street. We are located 1.5 miles from the Village, loaded with amazing shops, restaurants, and night life. Condo remodeled top to bottom in 2019. Beach towels, chairs, and accessories provided.

4.86 out of 5 average rating, 159 reviews

Heart of Village: Dog-Friendly w/ Pool & Parking

Escape to paradise in our newly renovated 2-bedroom condo, perfectly situated a block from Siesta Key Village. Enjoy the convenience of walking to bars and restaurants, plus two parking spots if you prefer to drive. Relax by the community heated pool or take an 8-minute stroll to the award-winning beach. Explore the area using the free trolley, or venture to downtown Sarasota. This dog-friendly condo offers Wi-Fi, a smart TV, in-unit laundry, and essential home and beach gear.

4.92 out of 5 average rating, 165 reviews

Gulf Views | Walkable | Spacious

Spacious Gulf-view 2BR condo perfect for families & groups—featuring a rare 2-queen guest room, king master, and plenty of room to spread out. Walk to the beach, restaurants, coffee, and more—no car needed. Easy beach access + FREE loungers make beach days effortless. Heated pool, fast WiFi & fully stocked with beach gear. Clean, spacious & comfortable in a prime, walkable location. (Daytime weekday construction nearby may cause intermittent noise in 2026.)

4.92 out of 5 average rating, 170 reviews

Condo in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

A modern living area showcases a comfortable sectional sofa and armchair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a media console. Natural light floods the space through sliding glass doors that lead to a balcony, enhancing the open feel.