
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

Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

East Hampton Village Fringe, Renovated with Pool
This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Summer Retreat at the beach , enjoy Wine Country
* We provide a Beach Parking Pass for all Southold Town Beaches * 10 min walk to neighborhood sandy beach! * 5 min walk to vineyard with tasting room. Spacious Contemporary home. Master Bedroom plus 2 more bedrooms and 2 bathrooms on the second floor. Living room & kitchen on main floor. Wake up to beautiful garden view. Large kitchen and dining area for the whole family. Just minutes from Long Island's wineries and wedding venues. This home comes complete with everything you need!

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!

Private 1st flr apt w/ patio 3 blocks from beach
We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer. Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

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).

Exclusive Sag Harbor Compound
A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.
Popular amenities for Southold family-friendly rentals
Family-friendly home rentals with a hot tub

Private Oasis W/Stunning Vinyard and Pool Views

Greenport Village walking distance to all

Luxury cottage by the sea with hot tub and pool

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

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

Beach Haven - waterfront, near Yale, sunsets

Explore the Water & Woods at a Relaxing Retreat

Delightful Cape House in Greenport
Family- and pet-friendly home rentals

Savor Ocean Sunsets at a Soothing Beachfront Haven

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

Beautiful Airy Barn in Springs

The Cottage at Indian Cove

Maritime Village Getaway with Backyard

Cozy Farmhouse Retreat in North Fork, NY

Secluded Farmhouse - Studio Apartment Style Unit

Hamptons Oceanfront Oasis
Family-friendly home rentals with a pool

Corwin House

The Perfect North Fork Escape

Beautiful condo on Long Islands Northfork

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Beautiful Waterview Condo on the North Fork of LI

Classic Southampton Village Home w/ Pool

Nassau Point, North Fork Home w/ Pool

Large heated pool, games room, near private beach
Quick stats about holiday rentals that are family-friendly in Southold
Total holiday rentals
Explore 230 holiday rentals in Southold
Nightly prices starting at
Southold holiday rentals start at € 78 per night before taxes and fees
Verified guest reviews
Over 4,780 verified reviews to help you choose
Pet-friendly holiday rentals
Find 70 rentals that welcome pets
Holiday rentals with a pool
90 properties feature pools
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Wifi availability
220 of Southold holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Southold rentals
4.9 Average rating
Southold stays are highly rated by guests – averaging 4.9 out of 5!
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- Family-friendly rentals Suffolk County
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- 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