Luxury houses with pool for rent Osterville, United States

Single level luxury living offered for September 2024 - May 2025. With character-rich details at every turn, this stylish abode has just undergone a spectacular resurrection. From the sun-drenched eat-in kitchen with double-height ceilings to a glamorous den adorned with an opulent creamy shell chandelier- this midcentury cottage offers delightful, carefully designed elements around each and every corner. The den flows into a light-filled, three-season room (which could serve as an office) overlooking the patio — the perfect sunny spot to read, rest or converse. Past the vibrant powder room is an alluring hallway with a glossy, edgy green ceiling leading to the “sleeping wing,” with four exquisitely appointed bedrooms and three full baths. The woodland-inspired primary suite boasts views of the European-inspired in-ground pool and an acre of lush grounds- perfectly fenced-in and landscaped. The lower level has been finished to create a hip lounge space with adjacent laundry room. With plenty of parking, plus a 2-car garage, this home is exactly what you have been waiting for.

Here's the perfect home for year-round living or summer enjoyment! Sited on a beautifully landscaped 1+/- acre in the Northwest Woods that's convenient to East Hampton Village and bay beaches, this lovely property boasts 4 bedrooms, 2.5 baths, and much more. The living room and dining area with cathedral ceilings and skylights create a bright and airy space with wood burning fireplace and glass doors opening to the heated pool and entertaining deck. The house also boasts a generous eat in kitchen and first floor primary suite with 3 guest bedrooms upstairs and a full basement. The perfectly positioned heated pool has an electric pool cover and is surrounded by spacious decking set among flowering shrubs and mature trees to create an ideal spot for relaxing or entertaining. The house also comes with a generator to set your mind at ease should a storm or accident cause a power disruption. Nicely location close to Three Mile Harbor and bay beaches, and short drive into the Village of East Hampton. [[Rental Registration # 22-1276]] EH RR #: 22-1276 Rental Terms: Winter Season: $25,000 Per Month

Centrally located one level cute traditional with sunny open plan living/dining area well stocked kitchen, 2 bedrooms, 2 baths and finished lower level. This home opens onto a private recently refurbished southeast facing deck with steps down to the pool and surrounding brick patio. Walking distance to the fabulous restaurants and shops on North Main Street and EH Village. Ocean Beaches are five minutes away. [[Rental Registration # 23-688]] EH RR #: 23-688 Rental Terms: August: $30,000 August - Labor Day: $32,000 July: $25,000 Winter Season: $5,000 Per Month

This recently renovated home is an excellent blend of village charm and modern amenities. Located one block from Haven's Beach and a five-minute stroll from the village center, this historic house has a gracious open floor plan that is ideal for summer entertaining. The large open kitchen has an easy flow to the outdoor mahogany deck, tastefully landscaped backyard and 10'x40' heated gunite saltwater pool. The master bedroom features an en-suite bathroom with large glass shower and radiant heated floors. A Juliet balcony overlooks the backyard, complete with its own fruit-producing peach tree. Two additional bedrooms and a recently added fourth bedroom/den on the first floor combine with additional amenities, including a large mudroom, a double set of washer/dryers, three-zone central A/C, a wood burning fireplace, and a 50 HDTV. The dual benefit of a secluded location and proximity to town complete this Sag Harbor Village gem. EH RR #: R-24-0004 Rental Terms: Winter Season: $45,000 Per Month September: $30,000

2024 Rates: June $6,250/week or $25K/month; July $8,125/week or $32,500/month A1-LD $8,750/week or $35K/month. Experience North Fork summer living in this newly introduced gem! Nestled in the sought-after Eastern Sterling Shores community, this impeccably designed modern farmhouse offers exclusive access to a private Long Island Sound beach. Step inside to discover a light-filled and meticulously styled interior adorned with contemporary finishes and furnishings. The heart of the home is the chef's kitchen seamlessly integrated into the Great Room and anchored by a cozy gas fireplace. On the first floor, you'll find a convenient half bath, a junior en-suite bedroom, a spacious mudroom, and a sizeable 2-car garage. Ascend to the second level to encounter two additional guest bedrooms sharing a full bathroom, along with a stunning primary en-suite bedroom. The primary bath boasts a luxurious double vanity, a walk-in shower, a soaking tub, and an expansive walk-in closet for added convenience and indulgence. Outside, the property showcases a captivating landscape featuring a sprawling stone patio enveloping a 20x40 heated salt-water pool, complemented by an outdoor shower - an ideal setting for hosting gatherings and enjoying the summer sun.

In the heart of Southampton Village, this property is walking distance to shops and restaurants. Renovated and beautifully furnished, offering 4 bedrooms, 4 1/2 baths, generous living spaces, and a gorgeous screened in porch overlooking the backyard. New heated gunite pool and hot tub, surrounded by blue stone, outdoor shower, bbq, and pool house with TV, AC, and full bathroom. Everything you need for the perfect stay this summer in the most convenient location! Rental Terms: Winter Season: $70,000 Per Month