
Family-friendly holiday rentals in Southold
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Top-rated family-friendly rentals in Southold
Guests agree: these family-friendly homes 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

Amazing Home close to Everything -
Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

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!

The Greenport Suite—private entry + near the beach
Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

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).

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 RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH
4-6 GUEST MAXIMUM PLEASE. Cozy 2 BR and 1 BTHRM apartment in private home in Greenport NY. Total privacy and separation of unit!! Perfectly situated on 1.75 acres. 3 minute drive, or easy walk, to the center of Greenport village, 2 minute ferry ride to quaint Shelter Island, and a 6 minute drive to tip of Orient. So right in the middle of the action with the peace and serenity of living outside the village. Private beach a short walk/ride down the street.

Modern Farmhouse Steps to Beach & Love Lane
Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

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).

Walk to Breakwater Beach in Heart of Wine Country
Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

Walk to Vineyards, Beaches, Farms & Town
Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!
Popular amenities for Southold family-friendly rentals
Family-friendly home rentals with a hot tub

Walk-To-The-Beach House In The Dunes

Greenport Village walking distance to all

Luxe| Pool|Game Room |Outdoor Movie|HotTub|Firepit

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

East Hampton Oasis - Pool and Hot Tub

1800 Historical EH Home, 1 Mile to Town, Hot Tub!

Beach Haven - waterfront, near Yale, sunsets
Family- and pet-friendly home rentals

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Beautiful Airy Barn in Springs

Quaint Cottage on Long Island's South Shore.

The Cottage at Indian Cove

Cozy Farmhouse Retreat in North Fork, NY

Spacious East Hampton Getaway with Pool

Hamptons Oceanfront Oasis

Large heated pool, games room, near private beach
Family-friendly home rentals with a pool

Corwin House

The Perfect North Fork Escape

Peaceful Retreat in Immaculate Architect’s House

Stylish Beach Getaway: pool & walking location

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Stylish Getaway in Greenport

Beautiful Waterview Condo on the North Fork of LI

Classic Southampton Village Home w/ Pool
Quick stats about holiday rentals that are family-friendly in Southold
Total rentals
230 properties
Nightly prices starting at
€ 77 before taxes and fees
Total number of reviews
4.8K reviews
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Destinations to explore
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- House rentals Southold
- Waterfront rentals Southold
- Rentals with pools Southold
- Beachfront rentals Southold
- Pet-friendly rentals Southold
- Rentals with lake access Southold
- Rentals with a kayak Southold
- Rentals with beach access Southold
- Rentals with a fireplace Southold
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- Apartment rentals Southold
- Rentals with a patio Southold
- Rentals with outdoor seating Southold
- Rentals with a firepit Southold
- Rentals with a hot tub Southold
- Family-friendly rentals Suffolk County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Blue Shutters Beach
- Groton Long Point Main Beach
- Napeague Beach
- Cedar Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Silver Sands Beach
- Woodmont Beach
- Sunken Meadow State Park
- Jennings Beach
- Sandy Beach
- Wildemere Beach
- Ninigret Beach
- Seaside Beach
- Outer Beach at Smith Point County Park