Looking for a late summer escape or planning ahead for a holiday sojourn? We have suggestions. From private estates on Martha’s Vineyard to sun-drenched coastal villas in Sardinia, our latest available leases are primed for your next getaway. 

MARTHA’S VINEYARD, MASSACHUSETTS 18 Point Inner Way, Chilmark Represented by Valene Pires  Photos by Luxury Vision

Tucked away in one of the Vineyard’s most coveted Up-Island enclaves, this Chilmark retreat offers the kind of privacy and authenticity that defines a true island escape. Set amid the natural beauty of the island’s interior landscape, the property puts guests within easy reach of Chilmark’s uncrowded beaches, farm stands and unhurried coastal villages.

16 Shepherds Path, Chilmark  Represented by Valene Pires  Photos by Luxury Vision

A refined island escape with interiors designed for long, unhurried summers, 16 Shepherds Path offers generous gathering spaces, carefully considered details and the effortless flow between indoors and out. Whether hosting a large group or settling in for an extended stay, this property delivers a level of comfort and calm that’s difficult to replicate. 

41 Watcha Club Road, West Tisbury Represented by Paul Pertile  Photos by Luxury Vision

Secluded within a quiet West Tisbury setting in the center of the island, this four-bedroom coastal home pairs laid-back beach-house ease with amenities that genuinely deliver. A private beach and swimming pool define the outdoor experience, while the home’s relaxed, sunwashed aesthetic carries the island’s spirit through every room. For those who want waterfront access without the crowds, Watcha Club Road is the answer. 

30 Pierce Lane, Edgartown Represented by Paul Pertile  Photos by Luxury Vision

When a rental is built for a group, it should feel that way from the moment you arrive. This six-bedroom Edgartown estate is designed precisely for the kind of summer gathering that needs room to breathe, featuring multiple sitting rooms, a screened-in porch, a swimming pool and a pool house complete with its own kitchen, bedroom, pull-out sofa and full bath. Below the main level, an entertainment floor with shuffleboard, a television lounge and an electric fireplace ensures that the evening carries on long after dinner. 

NEW YORK, NEW YORK 286 Manhattan Avenue, Williamsburg Represented by Maurice Singer  Photos by Kristen Markoplis, Allyson Lubow Photography

Not every rental story is a retreat from the city; sometimes the city is the destination. This stylish Williamsburg residence puts guests at the center of one of Brooklyn’s most dynamic neighborhoods, with world-class dining, independent boutiques, and waterfront parks all within reach. Polished interiors and a thoughtful layout make it as well suited to a longer stay as a short one.

ASPEN, COLORADO 170 Falcon Road Represented by Heather Sinclair  Photo by Mountain Home Photo

At the end of a private road in Aspen’s exclusive Five Trees neighborhood, 170 Falcon Road is among the rarest offerings in Colorado mountain rental: a true ski-in/ski-out estate with sweeping views across the Roaring Fork Valley. Set on 1.4 acres, the nearly 9,000-square-foot residence pairs timeless mountain architecture ( stone, timber, dramatic proportion) with finishes that feel genuinely refined rather than merely expensive. Five en-suite bedrooms include a main-level primary suite, while the chef’s kitchen and great room centered on a floor-to-ceiling stone fireplace become natural gathering points for any group. Outside, an alpine retreat awaits: a spa, a waterfall feature and multiple entertaining terraces. A large gym with cold plunge rounds out the resort-caliber amenity offering.

705 Spruce Street Represented by  Lisa Hatem  Photos by Mountain Home Photo

Set at the base of Smuggler Mountain with panoramic views toward Aspen Mountain, 705 Spruce Street is a mountain-modern residence built for groups who need space without sacrificing intimacy. The open floor plan, crafted for both everyday living and effortless entertaining, is anchored by elevated finishes and detailed craftsmanship throughout. Eight bedrooms, including a separate guesthouse and a luxurious primary suite, offer the flexibility that larger parties and extended stays require. Expansive outdoor decks frame the mountain views and create an ideal setting for evenings spent outdoors. Privacy, scale and setting, all in one. 

125 W. Main Street Represented by Chris Flynn  Photo Credit: Girls at Flourish

Known as Magpie House, 125 W. Main Street is Aspen’s Victorian heritage reinterpreted for a design-forward generation. Completely reimagined in 2023, this four-bedroom, five-bath residence blends the city’s iconic 19th-century architecture with contemporary interiors of genuine character, which is a rare thing to find in the center of town. Four ensuite bedrooms and curated living spaces make it equally suited to quiet retreats and lively entertaining. 

SARDINIA, ITALY Villa Le Pernici Represented by Salvatore Baldinu 

Villa Le Pernici is Sardinia distilled: a property where traditional island architecture and contemporary luxury arrive at a rare and natural equilibrium. Stone, texture and the unhurried rhythm of Mediterranean life define the experience, while refined amenities ensure every comfort is met. Generous indoor and outdoor gathering spaces flow seamlessly between one another, reflecting the island’s relaxed approach to how people spend their days. 

A Private Coastal Villa Retreat in I Giardini di L’Aldia Represented by Salvatore Baldinu

Set within the sought-after residential enclave of I Giardini di L’Aldia, this private coastal villa is an intimate retreat at the edge of the Mediterranean. Natural surroundings, generous privacy and direct proximity to the sea frame daily life here, a combination that defines Sardinia’s particular brand of coastal luxury. For those seeking an escape that feels genuinely removed from the world while remaining effortlessly connected to the island’s most beautiful stretches of coast, this is exactly that.