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Family-friendly vacation rentals in Southold

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

  • Total vacation rentals

    Explore 220 vacation rentals in Southold

  • Nightly prices starting at

    Southold vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,740 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    210 of Southold vacation rentals include wi-fi 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!

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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Top guest favorite
A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.
Home in Mattituck

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.

FamilyIndoor spacesCheck-in

4.93 out of 5 average rating, 134 reviews
Top guest favorite
Guest suite in Southold

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 and provide a quiet and comfortable stay. About a 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.

Indoor spacesKitchenGetting around

4.94 out of 5 average rating, 157 reviews
Guest favorite
A bright living space is featured, furnished with two light-colored chairs and a dark coffee table. A flat-screen television is mounted on the wall. A doorway leads to a bedroom, while natural light filters in through the windows, illuminating the neutral decor.
Home in Greenport

Aqua Vista

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly-renovated 2-family Home! This rental is 2nd floor apartment (only). Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy. Located right in Greenport. Walking distance to all the restaurants, bars, shopping, coffee shops.

FamilyIndoor spacesBeach

4.95 out of 5 average rating, 270 reviews
Top guest favorite
A serene beach scene captures a golden sunset reflecting on calm waters. The sandy shore leads to gentle ripples, while distant land silhouettes frame the horizon. A tranquil ambiance is created as the sun descends, providing a peaceful setting for evening strolls.
Apartment in Southold

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!

FamilyIndoor spacesGetting around

4.95 out of 5 average rating, 156 reviews
Top guest favorite
A charming historic boathouse features a steeply pitched roof with shingle siding and decorative trim. A white picket fence surrounds the property, while blooming shrubs enhance the entrance. A balcony adorned with planters awaits above the front door, complementing the inviting facade.
Home in Greenport

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's with modern updates. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

FamilyIndoor spacesCleanliness

4.97 out of 5 average rating, 121 reviews
Guest favorite
The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.
Condo in Greenport

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

FamilyKitchenLocation

4.89 out of 5 average rating, 199 reviews
Top guest favorite
A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.
Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

FamilyIndoor spacesAmenities

4.97 out of 5 average rating, 218 reviews
Guest favorite
The front exterior of the bungalow is showcased, featuring a wooden fence that provides privacy and a garden filled with hydrangeas. The house displays large windows that invite natural light, set against a backdrop of gravel and greenery.
Home in Greenport

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

Indoor spacesFamilyCheckout

4.97 out of 5 average rating, 295 reviews
Top guest favorite
A bright and airy great room combines kitchen, dining, and living areas. Light wood cabinetry and stainless steel appliances complement the open layout. Soft white sofas with navy pillows are arranged around a wooden coffee table, and a round mirror enhances the natural light from multiple windows.
Apartment in Greenport

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars.

Indoor spacesKitchenSleep quality

4.96 out of 5 average rating, 178 reviews
Guest favorite
A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.
Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

Indoor spacesFamilyLocation

4.96 out of 5 average rating, 215 reviews
Guest favorite
The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.
Guest suite in North Fork

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!

FamilyKitchenDecor

4.88 out of 5 average rating, 747 reviews
Guest favorite
A vibrant orange car is parked on a gravel driveway in front of a navy blue house. Lush greenery surrounds the property, and a neatly manicured lawn extends beside a stone walkway leading to the entrance.
Home in North Fork

Beach House in L.I. Wine Country

Time to wine 🍷 down and make your way to the scenic North Fork. A clean and clutter-free beach house awaits. The Navy House is centrally located in a quiet residential enclave, steps away from Norman E. Klipp Marine Park (aka Gull Pond Beach) and a short drive to Greenport’s Historic Village, vineyards and farmstands.

KitchenFamilyBeach

4.98 out of 5 average rating, 125 reviews

Popular amenities for Southold family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.
Home in Greenport

Greenport Village walking distance to all

KitchenIndoor spacesHospitality

4.99 out of 5 average rating, 211 reviews
Guest favorite
Home in Sag Harbor

Barefoot Bliss | Quiet Family Retreat Heated Pool

Indoor spacesKitchenQuiet

4.91 out of 5 average rating, 202 reviews
Guest favorite
A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.
Apartment in Southampton

Swimming pool w/Hot tub Fire Pit Coffee Bar

FamilyIndoor spacesDecor

4.96 out of 5 average rating, 109 reviews
Guest favorite
Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

Indoor spacesFamilyDecor

4.96 out of 5 average rating, 184 reviews
Guest favorite
The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.
Home in East Hampton

Sprawling Hamptons Estate with Hot Tub & Amenities

KitchenFamilyBiking

4.78 out of 5 average rating, 145 reviews
Guest favorite
A spacious living area features exposed wooden beams and a cozy brick fireplace. Comfortable seating includes a brown sofa and recliner, with decorative pillows adding warmth. A glass coffee table stands on a colorful area rug, while large windows overlook the greenery outside.
Cabin in North Fork

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Indoor spacesKitchenOutdoor spaces

4.87 out of 5 average rating, 124 reviews
Top guest favorite
A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.
Home in East Hampton

Explore the Water & Woods at a Relaxing Retreat

KitchenFamilyCheck-in

4.98 out of 5 average rating, 144 reviews
Superhost
A cozy bedroom features a queen bed with a light blue quilt and a green loveseat nearby. Natural light enters through sliding glass doors, revealing a serene outdoor space. A decorative plant and framed artwork add a touch of interest to the room.
Guesthouse in East Hampton

Detached bungalow w/ private bath

Indoor spacesFamilyTV

4.82 out of 5 average rating, 349 reviews

Family- and pet-friendly home rentals

Top guest favorite
The exterior of the farmhouse is framed by well-maintained hedges, with a simple wooden staircase leading to the front door. Brightly lit windows are positioned symmetrically, highlighting the home's classic architecture. The surrounding greenery complements the inviting entrance.
Home in Greenport

Cozy Farmhouse Retreat in North Fork, NY

Indoor spacesFamilyNearby

4.92 out of 5 average rating, 133 reviews
Guest favorite
Home in Greenport

Chic greenport village home

Indoor spacesKitchenGrill

4.93 out of 5 average rating, 139 reviews
Guest favorite
A modern cottage is set amidst lush greenery, featuring a spacious rear deck and a lower patio area with two lounge chairs. The second story includes a covered deck with an awning, while large windows invite natural light into the interior.
Home in Mattituck

Walk to Breakwater Beach in Heart of Wine Country

KitchenIndoor spacesCheck-in

4.92 out of 5 average rating, 116 reviews
Superhost
A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.
Apartment in Shelter Island Heights

Squire Chase House

Indoor spacesFamilyCleanliness

4.9 out of 5 average rating, 271 reviews
Guest favorite
Home in Springs

Serene + private ~ 1 block to waterfront dining

Indoor spacesKitchenDecor

4.91 out of 5 average rating, 141 reviews
Guest favorite
A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.
Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

KitchenIndoor spacesBathroom

4.94 out of 5 average rating, 116 reviews
Top guest favorite
An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.
Home in Bridgehampton

Amazing Home close to Everything -

KitchenIndoor spacesHeating

4.94 out of 5 average rating, 334 reviews
Top guest favorite
A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.
Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

Indoor spacesKitchenComfort

4.98 out of 5 average rating, 182 reviews

Family-friendly home rentals with a pool

Superhost
A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.
Condo in Greenport

Waterfront Escape | Private Beach, Pool & Views

KitchenIndoor spacesSleep quality

4.85 out of 5 average rating, 174 reviews
Guest favorite
A serene backyard features a glistening pool surrounded by lush green grass and shaded areas. The house showcases large windows leading to a wooden deck with outdoor seating. Nearby, sun umbrellas provide shelter, enhancing the inviting outdoor space under the trees.
Home in North Fork

Quiet, Upscale Retreat by the Beach NEW Pool

Indoor spacesFamilyParking

4.96 out of 5 average rating, 118 reviews
Guest favorite
A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.
Condo in Greenport

Beautiful condo on Long Islands Northfork

Indoor spacesKitchenWifi

4.86 out of 5 average rating, 135 reviews
Top guest favorite
A well-maintained outdoor space features a blue swimming pool surrounded by lounge chairs and a red umbrella. Lush greenery lines the area, and a small shed is visible near the pool's edge, providing a serene atmosphere for relaxation.
Home in North Fork

The Perfect North Fork Escape

FamilyKitchenWalkability

4.88 out of 5 average rating, 138 reviews
Top guest favorite
A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.
Home in Hampton Bays

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

FamilyIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 154 reviews
Guest favorite
A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.
Home in Westhampton Beach

Luxury Hamptons Home with Heated Saltwater Pool

Indoor spacesFamilyGrill

4.98 out of 5 average rating, 173 reviews
Guest favorite
A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.
Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

Indoor spacesFamilyLocation

4.87 out of 5 average rating, 137 reviews
Guest favorite
A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.
Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

KitchenFamilyNearby

4.95 out of 5 average rating, 204 reviews

When is the best time to visit Southold?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$102,510 GYDG$135,983 GYDG$104,602 GYDG$103,765 GYDG$104,602 GYDG$119,455 GYDG$135,983 GYDG$135,983 GYDG$112,970 GYDG$105,648 GYDG$104,393 GYDG$100,627 GYD
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