Luxury rentals in Sarasota County

An aerial view of a modern, multi-level vacation rental surrounded by lush greenery and palm trees. A private heated pool is visible in the backyard, along with a spiral staircase leading to the roof. The Gulf of Mexico can be seen in the background.

5 out of 5 average rating, 18 reviews

400ft to Beach, Ocean View, Pool, in the Village

Siesta Key Dream’s largest and most luxurious vacation rental, features four levels, totaling 6-bedrooms, 9-beds, & 6 full-bathrooms. Notable attributes include: a heated-pool, hot tub, 2-balconies, a roof-top sundeck, parking, a backyard and an elevator. With a premier location, beach access point #4 is 400 feet away, and the Siesta Key Village is one block away. In addition to a highly desired location, the unique property design allows beach and Gulf of Mexico views from multiple levels.

The image showcases a private pool area, featuring a unique waterslide and in-ground spa, illuminated in vibrant blue tones as the sky transitions to dusk. Comfortable lounge chairs are positioned beside the pool, surrounded by lush palm trees and a spacious deck area.

4.86 out of 5 average rating, 7 reviews

New Home with Pool, Spa, Waterslide - Seascape

Seascape by Lido Key Vacations Sarasota FL 34236 VR24-00004 Welcome to Seascape, a stunning vacation home boasting eight spacious bedrooms and eight-and-a-half luxurious bathrooms. With a gorgeous private pool, spa, and waterslide, you'll be living in paradise! Plus, the rooftop deck offers incredible views, and it's only a block away from Lido Key Beach, where you can catch breathtaking sunsets. This vacation home is perfect for families and large groups seeking a memorable beach

The exterior of a three-story vacation home is highlighted, showcasing large glass doors and multiple balconies. Lush greenery surrounds the property, while a rooftop deck can be seen, providing additional outdoor space. The driveway offers ample parking with two garage spaces visible.

5 out of 5 average rating, 6 reviews

Gulf Views/Walk to St. Armands & Beach-Resort Pool

Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation experience! Per City of Sarasota's Rental Ordinance - This home must be rented for a minimum of 7 nights, and it has a max occupancy of 12 adults, *but children under 6 years of age do not count toward the City's max occupancy count. Vunique Vacations restricts the total occupancy of the home to 16 persons, including adults and children under 6 years of age.

The outdoor space features a landscaped area with a heated saltwater pool and spa, accompanied by a 60-foot waterslide. Smooth putting greens and lounge chairs are situated around the pool, enhanced by lush tropical plants and the inviting glow of dusk.

4.92 out of 5 average rating, 13 reviews

60ft. Water Slide - Golf Simulator - Mini Golf

Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation experience! Located in the heart of South Siesta Key Village! You are literally steps to all South Siesta's restaurants, entertainment, shopping, markets, marina, and much more! This super fun entertainment district is literally at the end of your street, steps away, and it has something for everyone, which is why it's a guest favorite!

The modern exterior of the home features a clean white facade with large windows, providing natural light. A welcoming entrance is marked by stylish light fixtures and palm trees, while colorful landscaping enhances the overall curb appeal.

5 out of 5 average rating, 4 reviews

Elegant 6BR Sarasota Home • Pool + Rooftop Views

Welcome to 2440 Floyd Street, a stunning, modern retreat in the heart of Sarasota. This spacious 6-bedroom, 4.5-bathroom home offers luxury, comfort, and privacy, making it the perfect getaway for families, groups, and corporate travelers. With a heated pool, private rooftop terrace, and a detached guest house, this home offers a true resort-style experience just minutes from Siesta Key Beach, Lido Key, and downtown Sarasota.

A private backyard features a heated pool surrounded by a spacious patio, ideal for relaxation. Adjacent stands a detached guest house, while a modern main house showcases large windows and outdoor seating. Tropical landscaping complements the serene atmosphere.

Luxury 6BR Sarasota Escape • Pool & Rooftop

Welcome to 2430 Floyd Street, a stunning modern retreat in Sarasota’s historic Arlington Park neighborhood. This 6-bedroom, 4.5-bath home offers 2,743 sq. ft. of stylish living space, perfect for families, groups, or business travelers seeking a luxurious and relaxing getaway. With a heated pool, outdoor kitchen, rooftop terrace, and detached guest house, this home delivers the ultimate Sarasota experience.

A modern home with two structures is surrounded by lush tropical landscaping. A sparkling heated pool takes center stage, while spacious patio areas are visible. The upper level of the detached guest house features a staircase leading to an inviting entryway.

Luxury 6BR Sarasota Home Near Siesta Key

Welcome to your ultimate Sarasota getaway! This stunning, modern 6-bedroom, 4.5-bath home is designed for comfort and style, offering a spacious open floor plan, high-end finishes, and resort-style amenities. Located in the heart of Sarasota’s historic Arlington Park neighborhood, this luxurious retreat is just minutes from Siesta Key Beach, Lido Key, and downtown Sarasota.

An aerial view of a modern coastal home highlights its spacious rooftop deck with ample seating. Surrounding palm trees and a backdrop of the Gulf of Mexico contribute to a serene coastal setting under a bright blue sky.

5 out of 5 average rating, 5 reviews

Walk to St. Armands & Beach/Gulf Views/Resort Pool

Per City of Sarasota’s Rental Ordinance - This home must be rented for a minimum of 7 nights, and it has a max occupancy of 12 adults, *but children under 6 years of age do not count toward the City’s max occupancy count. Vunique Vacations restricts the total occupancy of the home to 16 persons, including adults and children under 6 years of age.

The exterior of the house features a modern three-story structure with a light-colored façade and dark accents. A double garage is visible at the base, surrounded by a landscaped yard with palm trees. The sky displays subtle hues of pink and blue at dusk.

5 out of 5 average rating, 7 reviews

1 min to Beach & Pool - Shell-Abrate Good Times

Please note that this home is in close proximity to an ongoing construction project. Please inquire with the host for more information. Shell-Abrate Good Times by Siesta Key Luxury Rental Properties Home in Sarasota FL 34232 Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key!

A modern two-story home is framed by a large, mature tree. The exterior features a combination of light-colored walls and a dark metal roof. Tall windows allow natural light to illuminate the entrance, which is highlighted by stylish wall sconces.

Luxury 5BR Sarasota Stay • Spa + Outdoor Living

Welcome to Arlington Oak House, a stunning modern retreat in the heart of Sarasota’s charming Arlington Park neighborhood. This spacious five-bedroom, four-and-a-half-bathroom home offers a luxurious getaway with designer interiors, an inviting outdoor living area, and easy access to the city’s top beaches, dining, and entertainment.

7Bedroom Luxury Home W/Private Pool on Siesta Key!

Welcome to Las Palmas! This gorgeous new home on Siesta Key offers luxury around every turn. Stay with up to 16 guests in this 7-bedroom, 7.5-bathroom home, complete with a private pool and spa area, fenced in yard, large full kitchen, dining room, two living spaces with a game room, and much more!

An inviting outdoor space showcases a heated saltwater pool, complete with two sun-shelf areas for lounging. Tropical greenery surrounds the area, and colorful lighting enhances the serene atmosphere. Sunning chairs and a table are positioned near the water's edge for relaxation.