Luxury properties for rent Southold, United States

Beautiful renovated 2-bedroom, 2 full bath home in Orient Village. Open concept – living/dining/gourmet kitchen. Lower level with screening room, office, full bath. Walk from Jitney. Enjoy all village amenities, bay & sound beaches. Close to Orient Beach State Park & Cross Sound Ferry. Available April $5,000; May $5,000; June $7,000; July $15,000; Aug $15,000; Sept $8,000. Permit# 1364.

AVAILABLE FOR THE MONTH OF AUGUST. Embrace Coastal Serenity in a Fully Renovated 5 bedroom, direct waterfront Estate WITH ITS OWN PRIVATE BEACH! Discover the epitome of waterfront luxury in this exquisite Clinton, CT residence, where historic charm meets modern elegance. Nestled on a generous .51-acre lot, this multi-level home boasts of a direct waterfront access with plenty of privacy. Built in 1912 and meticulously renovated along the way. Experience the perfect blend of timeless architecture and contemporary updates. A spacious primary suite (with private balcony!) and two additional bedrooms on the second floor, plus two bedrooms and a rec room on the third floor, provide ample space for family and guests. Step outside to enjoy multiple decks with a panoramic view of Long Island Sound and private beach access for tranquil waterfront living. A spacious Living Room with a fireplace, formal Dining Room, light filled Great Room, and a Sunroom offer diverse areas for relaxation and entertainment. This property is a rare gem, offering a waterfront lifestyle coveted by many but enjoyed by few. Whether basking in the warmth of your fireplace or soaking up the sun on your private beach or deck, this home is a sanctuary for those who seek a blend of luxury and tranquility. It's the perfect home for a month retreat!

Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen is highlighted by gleaming wood counters and a beautiful decorative fireplace. Rounding out the first floor, you'll find the sun filled napping corner, a tucked away charming TV area and a second full bath. You'll also appreciate the mini-mudroom drop zone perfect for your bags, boots and hats! Upstairs you'll find an additional bedroom and a second media or lounge area. This space is ideal for guests or a quiet place to unwind. Enjoy the convenience of an outdoor shower, grill, fire pit and the nicely sized, partially fenced in yard. Fancy a stroll to town? It's just down the block with terrific shopping and dining. Enjoy all the amenities that make this shoreline town so popular and accessible, including access to Amtrak and the Shoreline East Train. Tenant: renters insurance, heat, electric, water and a one time end of lease cleaning. Landlord: all other utilities. No pets or smoking. A truly special place to hang your hat. July and August 2026. Also available September 15, 2026 - May 31, 2027 for 3K per month.

Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen is highlighted by gleaming wood counters and a beautiful decorative fireplace. Rounding out the first floor, you'll find the sun filled napping corner, a tucked away charming TV area and a second full bath. You'll also appreciate the mini-mudroom drop zone perfect for your bags, boots and hats! Upstairs you'll find an additional bedroom and a second media or lounge area. This space is ideal for guests or a quiet place to unwind. Enjoy the convenience of an outdoor shower, grill, fire pit and the nicely sized, partially fenced in yard. Fancy a stroll to town? It's just down the block with terrific shopping and dining. Enjoy all the amenities that make this shoreline town so popular and accessible, including access to Amtrak and the Shoreline East Train. Tenant: renters insurance, heat, electric, water and a one time end of lease cleaning. Landlord: all other utilities. No pets or smoking. A truly special place to hang your hat. Available September 15, 2026 - May 31, 2027. Also July and August at 6K per month.

Discover 9 Essex Rd (YEAR ROUND RENTAL) a renovated spacious 3-bedroom, 1-bathroom home in beautiful downtown Westbrook. This property features an updated kitchen, modern bath, washer and dryer, and a shared yard. Enjoy immediate access to the town beach, restaurants, Shoreline East train, and I-95. Water and trash removal are included; tenants are responsible for all other utilities. Pets will be considered. Private parking available in the back of the house.

Now available for rent, this quintessential, fully renovated, New England Gambrel Colonial is nestled on a half-acre and located on a quiet cul-de-sac in the scenic shoreline town of Old Lyme. This four-bedroom home with gleaming refinished hardwood floors, has been fully updated and offers the best of coastal living, situated just minutes from Old Lyme Village, Long Island Sound, Black Hall River Marina, and White Sands Town Beach. This property offers the best of coastal living where breathtaking sunsets, sandy beaches, and endless water activities are right at your doorstep. Whether it's kayaking, paddle boarding, fishing, boating, or simply enjoying nature, this location is perfect for creating lasting memories. Fully repainted and designed for both comfortable entertaining and everyday living, the new spacious eat-in kitchen flows seamlessly into the inviting dining room. Sliders lead to a private deck overlooking the expansive backyard, which is ideal for summer barbecues, relaxing, or recreation. The main level also offers a living room, a new full bathroom, and a bedroom, providing flexibility for guests, multi-generational living, or a home office. Three bedrooms and a new full bath complete the second level. Experience the beauty, comfort, and lifestyle of Old Lyme's shoreline.

ANNUAL UNFURNISHED (OR PARTIALLY FURNISHED) RENTAL), AVAILABLE AUGUST 1. Located between downtown Madison and the Hammonasset State Park Beach, this 3 bedroom renovated ranch offers a comfortable life style. The house offers a deck to enjoy the outdoors, large yard, easy access to the Shoreline Greenway Trail and beach access at the end of Webster Point Road. The primary bedroom has a full bath, the other two bedrooms share a full bath. AC is via window units and heat is electric. This house is cute and comfortable. Some pets considered.

Daydreaming about waking up to the sounds of waves and walking to your very own private beach? Make your dreams come true at 118 Middle Beach Road! With 7 bedrooms, 5 full baths, and 2 half baths, this iconic property comfortably accommodates up to 14 guests. The main level is an entertainer's paradise featuring an oversized kitchen, formal dining area, living room with views from every angle, and generously-sized screened-in porch! In addition to six of the seven bedrooms, the second floor features a family room perfect for kicking back and soaking in the expansive views! The third floor is a private retreat with the seventh bedroom and enormous recreation room. Let's also remember the large, water-facing screened-in porch perfect for soaking in the sunrise and sunset each day. Just outside, sun, sand, and saltwater air await you! This is the perfect place to be this summer - schedule your private viewing today and enjoy your own private beach in a few short months! One month for $45,000, two weeks for $22,500 or one week for $12,500. Please reach out to listing agent for most up-to-date availability.