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Family-friendly holiday rentals in Southold

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Southold

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Home

4.88 out of 5 average rating, 226 reviews

Nautical Cottage Near Beach, Wineries, Golf, Shops

Coastal themed cottage located in the center of The Hamptons. Super Hosts! Great WiFi. Bright & comfortable space! Cowfish/Canoe Place Inn closeby! Near WINERIES, BEACHES, GOLF, WATERFRONT RESTAURANTS, & SHOPPING. 4 bedroom areas 2 full baths & outdoor shower. Spacious backyard w/ fire pit & deck w/ string lights. Lot's to do each season for couples, friends, coworkers & families. Everything you need & want in a Hampton's home. Large screen TVs/Roku, Foosball. Access to loft bedroom by ladder.

Guest favourite

Home

4.9 out of 5 average rating, 182 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence and gates around pool. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

Home

4.87 out of 5 average rating, 203 reviews

Cozy fireplace, yard4pup, walk to beach, spotless

Meticulously cleaned home. Tranquil family neighborhood in historic artist's beach community. Wood burning fireplace. Private fenced-in backyard . Heated saltwater pool in summer. Half mile to private bay beach, bike great trails & savor delicious meals prepared in fully equipped kitchen. Don’t miss Clearwater Beach's stunning sunset. Easy living home.Welcoming to all respectful families & guests.East Hampton's best restaurants are nearby. Smoke free.Small dogs permitted.Rental Registry 23-625.

Guest favourite

Cottage

4.93 out of 5 average rating, 264 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Guest favourite

Guest house

4.95 out of 5 average rating, 440 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

Cabin

4.86 out of 5 average rating, 139 reviews

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

Guest favourite

Bungalow

4.98 out of 5 average rating, 110 reviews

Hamptons Waterfront- Relax & Getaway!

My place is right on the water with your own sandy beach. A quick walk to the restaurant and dining. No worries about having a drink and getting home. You’ll love my place because of the location and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Conveniently located just minutes from the center of town for all your shopping needs; grocery store, Starbucks, 7-11, rite-aid, bagel cafe, pizzaria, farmers market and more.

Guest favourite

Home

4.98 out of 5 average rating, 203 reviews

Aqua Vista

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).

Guest favourite

Home

4.93 out of 5 average rating, 105 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Guest favourite

Home

4.93 out of 5 average rating, 108 reviews

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK: Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Pool open: Memorial Day - Labor Day Only.

Guest house

4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

Access to endless pool/spa, private beach around corner, breathtaking views, access for kayak, sup etc on property, playful friendly dog, easy access to all including sunset beach, beautiful breeze, private location, 46 foot classic powerboat available for charter at discounted rate w/ rental

Holiday rentals for every style

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Hotels

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Popular amenities for Southold family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Home

4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Home

4.94 out of 5 average rating, 17 reviews

Chic Beach House: Waterfront, Vineyards, Hot Tub

Guest favourite

Home

4.94 out of 5 average rating, 72 reviews

Family Friendly Springs Beach House

Guest favourite

Cottage

4.96 out of 5 average rating, 177 reviews

Secluded Southampton Cottage w/Pool & Spa

Guest favourite

Cabin

4.86 out of 5 average rating, 98 reviews

Beach & Forest: Cozy Cabin, Hot Tub, Peloton

Guest favourite

Home

4.88 out of 5 average rating, 24 reviews

NEWLY RENOVATED W/ POOL & FIREPLACE

Guest favourite

Home

4.83 out of 5 average rating, 161 reviews

Exquisite spacious waterfront all modern-sleeps 8

Home

4.83 out of 5 average rating, 210 reviews

Cozy & Chic Summer Getaway near village/beaches

Family- and pet-friendly home rentals

Guest favourite

Cottage

4.97 out of 5 average rating, 150 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Home

4.88 out of 5 average rating, 110 reviews

Gorgeous East Hampton Getaway

Guest favourite

Home

4.85 out of 5 average rating, 159 reviews

Sag Harbor House for rent.

Guest favourite

Home

4.98 out of 5 average rating, 244 reviews

The Greenport Bungalow

Flat

4.83 out of 5 average rating, 184 reviews

Pet friendly Apt. Plus cabin, EV charger & sauna.

Guest favourite

Guest suite

4.92 out of 5 average rating, 155 reviews

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

Guest favourite

Home

4.91 out of 5 average rating, 101 reviews

North Fork Escape - Walk To Village, Beach, Parks

Cottage

4.8 out of 5 average rating, 433 reviews

The Red Cottage Circa 1936

Family-friendly home rentals with a pool

Guest favourite

Home

4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

Home

4.94 out of 5 average rating, 122 reviews

Peaceful Retreat in Immaculate Architect’s House

Home

4.82 out of 5 average rating, 136 reviews

Thanksgiving! Sag Harbor Gem!

Home

4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Home

4.74 out of 5 average rating, 89 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

Guest favourite

Home

5 out of 5 average rating, 35 reviews

Stunning Central E. Hampton Home w/ gunite pool.

Guest favourite

Home

4.94 out of 5 average rating, 157 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Guest favourite

Home

4.85 out of 5 average rating, 261 reviews

Exclusive Sag Harbor Compound

Quick stats about holiday rentals that are family-friendly in Southold

Total rentals
180 properties
Nightly prices starting at
£64 before taxes and fees
Total number of reviews
2.5K reviews
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
110 properties have a dedicated workspace

Destinations to explore