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Best Vacation rentals and Airbnb offers in Southold, NY
10 3 reviews
Southold, NY
07/05 – 07/09
$2005/nighttotal: $8020 (4 )
New Construction Greenport Pool House - 3 Blocks From Town
4 4
house , Greenport
This Greenport villa is a short walk from the Greenport Farmers' Market, Railroad Museum of Long Island, and Camera Obscura, offering easy access to the town's attractions. The area is known for its charming shops, restaurants, and waterfront views. This 2,700 square foot home has three bathrooms, providing ample space for families or groups. Enjoy a private pool, spa tub, outdoor patio, and a fully equipped kitchen with modern amenities, including free WiFi.
9.5 30 reviews
Southold, NY
07/05 – 07/09
$1636/nighttotal: $6544 (4 )
North Fork Resort
3 4
resort , Greenport
Vacation resort listing with an excellent rating of 95% based on 30 reviews. This accommodation is located in Greenport. Services and facilities: a fridge, air conditioning and a barbecue. Enjoy free parking with this resort in Greenport!
10 6 reviews
Southold, NY
06/25 – 07/18
$1384/nighttotal: $31832 (23 )
Nassau Point Summer Escape
1 2
apartment , Cutchogue
This Nassau Point home, near Cutchogue and Southold, offers a 3.5-acre private setting with easy access to bay beaches (five-minute drive) and local restaurants and shops (ten-minute drive). This luxurious 4-bedroom, 4-bathroom house features a 50-foot gunite pool, spacious open layout, chef's kitchen, and can accommodate up to eight guests, also including a guest cottage, outdoor amenities and a library/office space.
9.6 5 reviews
Southold, NY
06/25 – 07/18
$531/nighttotal: $12213 (23 )
Sweet Southold Beach Cottage Fall Winter Spring Summer 1 Min Walk To Beach
2 2
apartment , Southold
This Southold cottage, a one-minute walk from Founders Landing Beach and a short stroll from the Boatyard Marina, boasts prime Peconic Bay views from its driveway. The 750-square-foot home features two bedrooms, one bathroom, and accommodates two guests; amenities include a fully equipped kitchen, air conditioning, a private spa, fitness center, and a spacious rear deck with a grill.
9.8 10 reviews
Southold, NY
06/25 – 07/18
$943/nighttotal: $21689 (23 )
Greenport Beach Family Home W/ Heated Salt Pool
3 2
apartment , Southold
This Southold home is located just 1.5 miles from Greenport Village and 2.5 miles from the heart of Southold, offering a peaceful retreat in a quiet neighborhood. The apartment has received excellent ratings for its cleanliness, location, and overall experience. This 3-bedroom, 2-bathroom home comfortably accommodates up to 6 guests. Enjoy a private bay beach, a heated pool, a BBQ grill, an outdoor fire pit, a hammock, a deck, and kayaks.
10 38 reviews
Southold, NY
07/05 – 07/09
$1256/nighttotal: $5024 (4 )
Perfect Waterfront Family Vacation Home Next To The Best Vineyards In Ny!
3 4
apartment , Southold
This 3-bedroom, 2-bathroom beachfront cottage in Southold offers direct access to a private community beach and is located near the Railroad Museum of Long Island and East End Seaport Maritime Museum, with Croteaux Vineyards and Mattebella Vineyards also nearby. This pet-friendly rental features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, spa, and parking, with opportunities for swimming, boating, and fishing on Goose Creek.
10 12 reviews
Southold, NY
07/05 – 07/09
$938/nighttotal: $3752 (4 )
Relaxation In Greenport
3 4
apartment , Greenport
This Greenport vacation home is ideally located a 5-minute walk from the Greenport Farmers' Market, Camera Obscura, and Railroad Museum of Long Island, and under 10 minutes from the East End Seaport Maritime Museum and Greenport Carousel. This 1,500-square-foot house features four bedrooms, two bathrooms, accommodates eight guests, and includes a fully equipped kitchen, private patio, free Wi-Fi, and parking.
9.1 249 reviews
Southold, NY
07/05 – 07/09
$685/nighttotal: $2740 (4 )
The Cliffside Resort Condominiums
1 4
apartment , Greenport
This Greenport apartment is located just a short drive from downtown Greenport and the Hortons Point Lighthouse, offering easy access to the area's attractions. The apartment is highly rated for its cleanliness, location, and overall experience. The two-bedroom apartment spans 550 square feet and provides a comfortable space for your stay. Guests can enjoy amenities like a swimming pool, a private beach, and a terrace, as well as convenient features like a kitchen, air conditioning, and free Wi-Fi.
10 4 reviews
Southold, NY
07/05 – 07/09
$2280/nighttotal: $9120 (4 )
Spacious North Fork Home In Greenport, Heated Pool, Perfect For Families
4 4
apartment , Shelter Island Heights
This four-bedroom, 3.5-bathroom house rental in Greenport, on Long Island's North Fork, is a short drive from Shelter Island Heights and offers easy access to beaches like HOA Beach and Southold Town Beach. The 4-bedroom home features a private heated pool and hot tub, multiple indoor/outdoor dining areas, a dedicated workspace, a gas BBQ, and accommodates up to eight guests; StayMarquis management provides 24/7 support.
Southold, NY
06/25 – 07/18
$575/nighttotal: $13225 (23 )
Southold Summer Rental
3 2
apartment , Southold
This three-bedroom Southold house, a short walk or drive from a private Peconic Bay beach, offers a peaceful North Fork escape near local restaurants and vineyards. The 1-acre property features a spacious, fenced backyard with a playground, a Weber grill, sun deck, high-quality entertainment system, and sleeps six guests in a king, queen, and two twin beds, plus two bathrooms and a full kitchen.
Southold, NY
06/25 – 07/18
$868/nighttotal: $19964 (23 )
North Fork Waterfront Beach House
1 2
apartment , Southold
This waterfront home with a private beach is located on the North Fork of Southold, 7 minutes from Greenport and near local vineyards and farm stands. This apartment features direct waterfront access, a private beach, an open floor plan with Sound views, a fully equipped kitchen with a wine refrigerator, and a spacious deck with a BBQ, accommodating up to 6 guests with a queen bed, twin beds, and a queen-size sleeper sofa.
8.6 9 reviews
Southold, NY
07/05 – 07/09
$2921/nighttotal: $11684 (4 )
Beautiful Contemporary Water Mill Home Centrally Located With Private Pool
5 4
apartment , Water Mill
This Water Mill vacation home is located 2.1 miles from the Hamptons Beaches and within 6 miles of attractions like the Elizabeth A. Morton National Wildlife Refuge, Noyac Golf Club, Parrish Art Museum, and Duck Walk Vineyards. This six-bedroom, four-bathroom house sleeps twelve guests and boasts a private pool, hot tub, fenced yard, game room, and fully equipped kitchen, perfect for family getaways or group vacations.
Best Southold, NY vacation rentals with a balcony
9.8 6 reviews
Southold, NY
06/25 – 07/18
$1652/nighttotal: $37996 (23 )
5 Bedrooms ~ Steps From A Private Sandy Beach And Beautiful Vineyard Views..
5 2
apartment , Southold
This Southold vacation rental, steps from a private beach and across from a vineyard, offers direct access to Shelter Island via a short 5-minute ferry ride. The 3200-square-foot home features five bedrooms sleeping ten, a modern contemporary design with high-end appliances (Sub-Zero, Wolf), abundant amenities (kayaks, bikes, beach gear, Sonos sound system), and expansive outdoor spaces including a deck, fire pit, and BBQ.
Southold, NY
07/05 – 07/09
$4351/nighttotal: $17404 (4 )
Hamptons 9bd Mega Compound W Pool Tennis Bball Nightclub
9 4
house , Noyack
This 9-bedroom villa is located in Noyack, 48 miles from Long Island MacArthur Airport. This spacious residence offers 5010 square feet of living space, accommodating up to 60 guests with amenities including a private pool, hot tub, and a well-equipped kitchen.
Southold, NY
06/25 – 07/18
$5396/nighttotal: $124108 (23 )
Private Hamptons Estate - 7 Br, Pool, Spa, Sag Harbor
7 2
apartment , Noyack
This new construction summer retreat is located on a private, gated drive in Sag Harbor, providing privacy and convenient access to Sag Harbor and Bridgehampton villages, as well as The Hamptons Beaches and Cooper's Beach. This 6,000 sq ft, three-level residence offers 7 bedrooms, 6 bathrooms, and can accommodate up to 10 guests, featuring a heated gunite pool, pool house, gym, sauna, and steam shower.
10 6 reviews
Southold, NY
07/05 – 07/09
$2043/nighttotal: $8172 (4 )
Spacious And Modern North Fork Home Close To Multiple Wineries, Perfect For...
3 4
apartment , Cutchogue
This three-bedroom, three-bathroom Cutchogue rental is conveniently located near Peconic Bay Vineyards on the North Fork, offering easy access to the North Fork wine trail and other attractions. The 3-bedroom home features a modern open layout, accommodating up to six guests with amenities including a gas grill, pool table, and foosball table, plus access to StayMarquis services.
Our Favorite Family-Friendly Vacation Rentals in Southold, NY
These family-friendly vacation rentals in Southold, NY offer spacious layouts and easy access to local beaches.
Southold, NY
07/05 – 07/09
$4680/nighttotal: $18720 (4 )
Villa Zainip - Luxury With Pool
5 4
house , Noyack
Villa Zainip is a luxurious home located in Sag Harbor, just 21 miles from Montauk Point Lighthouse and 26 miles from Splish Splash waterpark. The villa is conveniently located near the beautiful beaches of Sag Harbor, making it a perfect choice for families or groups of friends looking for a relaxing and enjoyable vacation. The villa offers 5 bedrooms, 4 bathrooms, and can comfortably accommodate up to 8 guests. The villa features a private pool and garden, a fully equipped kitchen, a sauna, and free Wi-Fi.
Southold, NY
06/25 – 07/18
$976/nighttotal: $22448 (23 )
195 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 2
house , Shelter Island Heights
The Haven on Glynn, a Rove Travel Home, is located in the Glynn district of Shelter Island Heights, offering convenient access to local attractions. This residence provides 2100 square feet of living space, accommodating up to 8 guests with 3 bedrooms, a full kitchen, air conditioning, and a garden, all within a family-friendly environment.
10 10 reviews
Southold, NY
07/05 – 07/09
$1140/nighttotal: $4560 (4 )
Luxury By The Sea
4 4
apartment , Southold
This Southold vacation home is located within 3 miles of five prestigious wineries—Croteaux, Mattebella, Corey Creek, Sparkling Pointe, and Sannino's Bella Vita—perfect for wine tasting. This three-bedroom, three-bathroom house sleeps eight guests comfortably, offering amenities such as a fully equipped kitchen, free Wi-Fi, a fireplace, barbecue grills, and air conditioning.
Southold, NY
06/25 – 07/18
$1213/nighttotal: $27899 (23 )
Elegant Victorian In The Heart Of Greenport
4 2
apartment , Greenport
This Pipes Cove vacation home in Greenport, New York, is steps from the East End Seaport Maritime Museum, Greenport Carousel, and Camera Obscura, and within a 5-minute walk of the Railroad Museum of Long Island and Greenport Farmers' Market. This four-bedroom, four-bathroom house sleeps 13, features a private fenced yard, on-site fitness center, gas grills, free WiFi, and a fully equipped kitchen including a refrigerator, microwave, and dishwasher; Greenport Station is a one-minute walk away.
Frequently Asked Questions about vacation rentals in Southold, NY
What are some interesting places to visit in or near Southold, NY?
Southold is a charming town with plenty to see. Visit the historic Southold Historical Society Museum to learn about the area's past. You can also explore the beautiful Long Island Sound, go wine tasting at one of the many vineyards in the area, or visit the Orient Point Ferry Terminal to catch a ferry to the mainland.
What are the best Airbnb and vacation rentals in Southold, NY?
Which walking or cycling routes are the best in Southold, NY?
The Southold Town Park is a great place to go for a walk or bike ride. You can also explore the scenic Southold Bay by bike on the Southold Bay Bike Path. If you want a longer ride, the Peconic Bay Trail runs for miles along the waterfront.
What are the most popular Airbnbs in Southold, NY?
What sports or outdoor activites can visitors enjoy in and around Southold, NY?
Southold is a great place to enjoy the outdoors. You can go fishing, boating, kayaking, swimming, or even go for a hike in the Orient Point State Park. In the summer, you can also enjoy the Southold Farmers Market, which has fresh produce and local crafts.
What are the best vacation rentals with a pool in Southold, NY?
What other towns or cities can be easily accessed from Southold, NY?
Greenport is just a short drive from Southold and is a great place to visit for its shops, restaurants, and harbor. Mattituck is another nearby town known for its wineries and farms. If you want to explore the rest of Long Island, you can easily get to Riverhead, Montauk, and Shelter Island from Southold.
What are the best rentals for families and kids in Southold, NY?
What amenities are commonly available in vacation rentals in Southold, NY?
Vacation rentals in Southold often come with amenities like a kitchen, laundry, and a private patio or balcony. Many also have access to a pool or hot tub. Some rentals even offer waterfront views or access to a dock.
What are the best rentals or Airbnbs with a jacuzzi in Southold, NY?
What time of year is best to rent a vacation rental Southold, NY?
The best time to rent a vacation rental in Southold is during the summer months, from June to August. The weather is warm and sunny, and there are plenty of outdoor activities to enjoy. However, spring and fall can also be beautiful times to visit, with cooler temperatures and fewer crowds.
Destinations nearby
Best Southold, NY vacation rentals with parking
10 1 review
Southold, NY
07/05 – 07/09
$4349/nighttotal: $17396 (4 )
Traditional-style Home With Private Pool, Sweeping Back Deck, Grand Lawn,...
4 4
apartment , Water Mill
This four-bedroom, three-bathroom Water Mill house rental is located just outside Bridgehampton, a short drive from the Parrish Art Museum and South Fork Natural History Museum. The 8-guest property boasts a private pool, expansive deck, well-equipped kitchen with stainless steel appliances, Wi-Fi, a washer/dryer, and ample parking, perfect for summer barbecues and relaxing after exploring the area.
10 3 reviews
Southold, NY
06/25 – 07/18
$968/nighttotal: $22264 (23 )
Shelter Island 3 Bed 2 1/2 Bath, 1.3 Acres Private, Quiet Water View Bay Access.
3 2
apartment , Shelter Island Heights
This Shelter Island Heights home is located directly across the street from the association day dock and landing to West Neck Bay, offering waterfront views and easy access to the water. It's a short distance from Sunset Beach, Shell Beach, and Shelter Island Country Club. This property has received excellent user ratings. The home has 3 bedrooms, 3 bathrooms, and can accommodate up to 6 guests in its 2,400 square feet of space. It offers a modern kitchen, a game room, a screened porch, a gas grill, and a fire pit, perfect for entertaining and enjoying the beautiful surroundings.
10 5 reviews
Southold, NY
07/05 – 07/09
$810/nighttotal: $3240 (4 )
Northfork Townhouse Walk To All
4 4
apartment , Greenport
This 3-bedroom house is conveniently located in central Greenport, within a 10-minute walk of the Greenport Farmers' Market, Railroad Museum of Long Island, and Camera Obscura. The home comfortably accommodates 6 guests and offers a fully equipped kitchen, outdoor barbecue grills, a garden, and free WiFi.
Southold, NY
06/25 – 07/18
$1333/nighttotal: $30659 (23 )
Haven On Glynn By Rove Travel | 3br Coastal Luxury
3 2
apartment , Shelter Island Heights
This Shelter Island Heights rental is located within 1 mile of Sylvester Manor, Havens House, and Shelter Island Country Club. This apartment offers air conditioning, a balcony, a garden, and a kitchen equipped with a fridge, microwave, and dishwasher, with parking available.
Neighborhoods and points of interest in Southold, NY
Search Vacation Rentals with Swimming Pool in Southold, NY
Enhance your coastal getaway with a Southold, NY vacation rental featuring a pool.
10 11 reviews
Southold, NY
06/25 – 07/18
$1099/nighttotal: $25277 (23 )
Tranquil Farm Setting In The Heart Of North Fork
1 2
apartment , Southold
This Southold apartment is just a short drive from Southold town, Horton Point lighthouse, Mcbain beach, and Greenport Village, nestled in a peaceful farm setting. It boasts excellent user, location, and cleanliness ratings. The 5-bedroom, 2-bathroom dwelling comfortably accommodates up to 10 guests. Enjoy modern amenities like smart TVs, a surround sound system, high-speed Wi-Fi, a fully stocked kitchen, a Weber BBQ, and an in-ground saltwater pool.
10 4 reviews
Southold, NY
06/25 – 07/18
$1481/nighttotal: $34063 (23 )
Northfork Villa! Pool-beach-wine
1 2
apartment , Southold
This luxurious Southold home, a short walk from Kenney's Beach and a short drive from Southold Village and the North Fork vineyards, offers unparalleled convenience to local attractions. The 6-bedroom, 4-bathroom residence boasts a 2-acre yard with a pool, BBQ patio, basketball court, putting green, game room, and multiple family rooms, comfortably accommodating up to 14 guests.
10 1 review
Southold, NY
06/25 – 07/18
$1143/nighttotal: $26289 (23 )
Log Home Sanctuary W/ Heated Pool & Hot Tub
4 2
apartment , Greenport
This Greenport vacation home, located near Gull Pond, is a five-minute drive from the maritime village and beaches. The 4-bedroom, 2-bathroom house sleeps nine, features a private hot tub, saltwater pool (opening summer 2025), air hockey, foosball, and two TV rooms, on a secluded 3.8-acre lot.
Southold, NY
07/05 – 07/09
$21451/nighttotal: $85804 (4 )
Villa Kimaal - Luxury With Pool
5 4
house , Noyack
Villa Kimaal, a luxury 5-bedroom estate in Sag Harbor, is situated 1.7 miles from Havens Beach and 16 miles from Montauk Point Lighthouse. This 5,010-square-foot house boasts a private pool, sauna, spa, and bar, accommodating up to 15 guests and offering amenities including free Wi-Fi, parking, and room service.
Top-Rated Oceanfront Vacation Rentals in Southold, NY
These seaside vacation rentals in Southold, NY provide an excellent base for exploring the coast. Browse top local properties and plan your beach-town trip.
Southold, NY
06/25 – 07/18
$3548/nighttotal: $81604 (23 )
North Fork Summer Rental $50k Per Month
1 2
apartment , Southold
9.9 38 reviews
Southold, NY
07/05 – 07/09
$3646/nighttotal: $14584 (4 )
Stunning Waterfront Estate House With 270 Degree Sea Views On 7 Private Acres
4 4
apartment , Shelter Island Heights
Southold, NY
06/25 – 07/18
$722/nighttotal: $16606 (23 )
North Fork Farmhouse
1 2
apartment , Cutchogue
Southold, NY
07/05 – 07/09
$1566/nighttotal: $6264 (4 )
Historic Over-the-water 3-bedroom Loft Apartment
3 4
apartment , Mattituck
Browse Luxury Vacation Rentals in Southold, NY
Experience 5-star comfort in a luxury Southold, NY vacation rental designed with premium amenities throughout.
Southold, NY
07/05 – 07/09
$1765/nighttotal: $7060 (4 )
Newly Renovated Sag Harbor Beach House With Pool
2 4
apartment , Noyack
Choose the Right Vacation Rentals with a Steam Room in Southold, NY
Relax with an on-site sauna at these vacation rentals in Southold, NY, perfect for a steam session after a day by the water.
