House holiday rentals in Southold

4.84 out of 5 average rating, 154 reviews

Home in Hampton Bays

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!

ValueLocationCheckout

A spacious gourmet kitchen is equipped with white cabinetry and a large island featuring a light-colored countertop. Pendant lights hang above the island, and stainless steel appliances are visible in the background, complemented by a tile backsplash and modern fixtures throughout.

4.95 out of 5 average rating, 55 reviews

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 🌊

LocationFamilyWalkability

A hot tub sits at the edge of a serene lake, surrounded by lush greenery and trees. The gentle ripples on the water reflect the sky, enhancing the tranquil setting. The peaceful landscape invites relaxation and offers a scenic view of nature.

4.83 out of 5 average rating, 46 reviews

Southold Sea'renity

Kick back and enjoy the peaceful surroundings of this beautiful 3-bedroom, 2-bathroom house. Outdoor oasis with hot tub, BBQ, shower, brand new deck & kayaks. Steps away from a fishing lake & 6 houses away from Kenny's beach. This house has been completely remodeled & is perfectly located to fit your getaway needs. Master Bedroom- queen bed, full bath Bedroom 2&3- queen beds Pull out couch and some other extras. Towels, bed sheets, soap, toilet paper, and pillows are included

LocationFamilyLaundry

A charming blue house is framed by lush green trees, with a welcoming front porch. Large windows invite natural light, while a white picket fence complements the tranquil outdoor setting. The spacious yard features vibrant grass, enhancing the peaceful atmosphere.

4.96 out of 5 average rating, 56 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

𓇼Walk to the Beach! ༄Location: quiet oasis by nature preserve, vineyards, breweries, farm stands, restaurants + attractions, 5 min to Greenport Village + Southold 𓇼Firepit, outdoor dining with string lights, grill, beverage cooler ༄Equipped kitchen w/blender, coffee, waffle maker + more! 𓇼Bathrooms w/heated floors + a clawfoot soaking tub (Please note there is only 1 shower) ☼Family Friendly: Board games, packNplay, high chair, beach chairs + toys ༄Kayak + bikes 𓇼Smart TVs

LocationFamilySleep quality

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.

4.97 out of 5 average rating, 119 reviews

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.

FamilyLocationBathroom

4.92 out of 5 average rating, 177 reviews

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

Home in Mattituck

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.

ValueLocationIndoor spaces

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.

4.97 out of 5 average rating, 218 reviews

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.

ValueFamilyCheck-in

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.

4.97 out of 5 average rating, 294 reviews

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!

FamilyLocationKitchen

A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.

4.95 out of 5 average rating, 393 reviews

The Sandpiper

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 is for rental of 1st floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

FamilyValueParks

4.92 out of 5 average rating, 115 reviews

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

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.

ValueLocationPets

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.

4.96 out of 5 average rating, 207 reviews

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.

FamilyValueParking

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.

4.99 out of 5 average rating, 211 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

FamilyLocationGetting around

Popular amenities for Southold house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

Home in Westhampton Beach

4.95 out of 5 average rating, 115 reviews

Brand new house with an all year round hot tub.

LocationValueHospitality

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.

4.96 out of 5 average rating, 117 reviews

Quiet, Upscale Retreat by the Beach NEW Pool

LocationFamilyHiking

4.98 out of 5 average rating, 144 reviews

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

FamilyLocationLong stay

Luxe

A charming cottage is surrounded by lush greenery, featuring a spacious lawn edged with neatly arranged flower beds. Large windows invite natural light, and a covered porch adds to the welcoming ambiance of the home.

Home in Amagansett

4.99 out of 5 average rating, 266 reviews

Historic Designer Farmhouse - Saltwater Pool

LocationValueHeating

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.

4.88 out of 5 average rating, 137 reviews

The Perfect North Fork Escape

ValueLocationCheck-in

4.94 out of 5 average rating, 113 reviews

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

LocationFamilyPool

4.94 out of 5 average rating, 332 reviews

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 -

ValueLocationDecor

4.95 out of 5 average rating, 201 reviews

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

ValueFamilyComfort

Weekly house rentals

4.91 out of 5 average rating, 43 reviews

Lakefront NoFo Cottage, walkable to public beach

FamilyLocationAir conditioning

5.0 out of 5 average rating, 39 reviews

Wine Country Home

LocationFamilyWalkability

A private pool area is shown with a clear blue swimming pool surrounded by four lounge chairs. A charming shed is situated in the background, framed by green trees and landscaped gardens.

4.88 out of 5 average rating, 24 reviews

Stylish Beach Getaway: pool & walking location

FamilyLocationComfort

4.9 out of 5 average rating, 41 reviews

Coastal Cottage on the Water

FamilyLocationBackyard

A living area features a comfortable blue couch paired with two round wooden coffee tables. Natural light enters through large windows, illuminating the space. A modern lamp and a decorative shelf add to the décor, while a minimalist fireplace is visible, enhancing the cozy atmosphere.

4.88 out of 5 average rating, 85 reviews

Le Petit Cottage, Southold, NY

ValueFamilyCleanliness

4.98 out of 5 average rating, 62 reviews

Corwin House

LocationValueBackyard

The living area features a combination of modern and historic elements, including a cozy seating arrangement with leather chairs and a round coffee table. Stained-glass windows add color, while a 65" television is mounted above a brick fireplace. Natural light illuminates the hardwood floors.

4.98 out of 5 average rating, 43 reviews

The Olde Church in Greenport

LocationBikingOutdoor spaces

5.0 out of 5 average rating, 6 reviews

Peconic Pearl Cottage

FamilyDecorHospitality

Private house rentals

4.83 out of 5 average rating, 12 reviews

North fork retreat with heated pool

LocationFamilyKitchen

A spacious living area is illuminated by natural light from skylights and large windows. A soft sofa is positioned on a light-colored rug, accompanied by a round pouf. Dining space is visible in the background, showcasing a simple wooden table and chairs.

4.95 out of 5 average rating, 86 reviews

Nassau Point, North Fork Home w/ Pool

FamilyLocationParking

Superhost

A well-lit living area features a large window and a glass door leading to the outdoor space. A modern fireplace is centered in the room, complemented by stylish furniture, including a curved sofa and a standing lamp. Art decor adds visual interest to the wall.

4.81 out of 5 average rating, 42 reviews

Stylish Getaway in Greenport

ValueFamilyDecor

Superhost

4.8 out of 5 average rating, 15 reviews

Peconic Sound Beach Cottage | Walk to Sound

LocationFamilyCheck-in

An aerial view captures the serene landscape of a coastal area, showcasing a blend of residential homes and natural beauty. The water glistens under the sunlight, with sailboats dotted along the horizon, creating a peaceful atmosphere. Trees and green spaces provide a calming ambiance.

4.93 out of 5 average rating, 73 reviews

Walk to Beach and Greenport Village, Two King Beds

FamilyLocationWalkability

5.0 out of 5 average rating, 9 reviews

Home in Mattituck

Serene and refined North Fork home with pool

FamilyLocationBackyard

A round door sign featuring the text 'Greenport Grace' in white script. The sign is divided into two sections with a dark wooden finish at the bottom and a light wooden finish at the top. A decorative black and white striped bow and greenery are attached to the top.

5.0 out of 5 average rating, 18 reviews

Greenport Grace: Private, Serene & Family Friendly

LocationFamilyWalkability

An inviting outdoor space with a spacious patio features a barbecue grill, seating area, and a dining table shaded by umbrellas. Lush greenery surrounds the area, and a glistening pool is visible in the background, enhancing the relaxing atmosphere.