
Vacation rentals in Southold
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Southold
Guests agree: these stays are highly rated for location, cleanliness, and more.

Waterfront Autumn Escape in Wine Country: 2BR
Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on your private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Stylish Beach Getaway: pool & walking location
Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Secluded Farmhouse - Studio Apartment Style Unit
Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

Bright, Southold Studio Apt near beach & town
Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

Luxury by the Sea!!
Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. This home is beautifully designed with too many architectural details to list. Property is fully furnished 🛋 with no detail spared . Open floor plan, spacious great room with gas fire place and flat screen, gourmet eat 🍝 in kitchen with large island is a wonderful place to entertain 🥂. Brand new washer/dryer, butlers pantry and mud room. Where the country meets the sea 🌊

The Sandpiper
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Gorgeous home with saltwater pool. Steps to beach!
Built in 1928, this gorgeous home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The local wineries are all within short drives of this lovely retreat. Enjoy the new heated gunnite pool with plenty of poolside seating. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

Comfortable Suite, a walk to the beach
Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact. Less than five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard, and Love Lane.

Greenport Beach house Mini Resort Spa & Catering
Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Beautiful condo on Long Islands Northfork
This condo is beautifully decorated and has a wonderful stone fire place. Gorgeous shiplap walls with Navy accents. There is also a new deck and wonderful dinning set outside. This unit has capabilities to be handicap accessible. Both bedroom have private bathrooms. The living room sectional opens up to a full sleeper making this condo able to sleep six people. All rooms have flat screen smart tv's.
Popular amenities for Southold vacation rentals
Other great vacation rentals in Southold

Sunny Harbor Suite

Waterfront beach cottage

Petite apt right in southold

Incredible 2 Bedroom Waterfront Cottage!

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

Stunning waterfront modern farmhouse with dock.

Peconic Retreat: Charming Home, Across from Beach

North Fork Estate in Midst of Vinyard
Quick stats about vacation rentals in Southold
Total rentals
260 properties
Nightly prices starting at
$126 CAD before taxes and fees
Total number of reviews
5.8K reviews
Family-friendly rentals
230 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
100 properties have a pool
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Ocean City Vacation rentals
- The Hamptons Vacation rentals
- Rentals with pools Southold
- Rentals with a patio Southold
- Rentals with lake access Southold
- Family-friendly rentals Southold
- House rentals Southold
- Waterfront rentals Southold
- Beachfront rentals Southold
- Rentals with beach access Southold
- Rentals with a washer and dryer Southold
- Rentals with a firepit Southold
- Rentals with a kayak Southold
- Rentals with outdoor seating Southold
- Rentals with a fireplace Southold
- Rentals with a hot tub Southold
- Pet-friendly rentals Southold
- Condo rentals Southold
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Blue Shutters Beach
- Shinnecock Hills Golf Club
- Napeague Beach
- Cedar Beach
- Groton Long Point Main Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Sunken Meadow State Park
- Sandy Beach
- Jennings Beach
- Wildemere Beach
- Ninigret Beach
- Mystic Seaport Museum
- Outer Beach at Smith Point County Park