House vacation rentals in Southold
Find and book unique houses on Airbnb
Top-rated house rentals in Southold
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Southold house rentals
House rentals with a pool
Home in East Hampton
4.93 out of 5 average rating, 140 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in Manorville
4.98 out of 5 average rating, 199 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in Southampton
4.96 out of 5 average rating, 130 reviewsWaterview, PoolOpenNow! DogsFree+Kayaks+PingPong
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Weekly house rentals
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Home in Cutchogue
4.97 out of 5 average rating, 30 reviewsCozy Cottage with Views
Home in Southold
4.96 out of 5 average rating, 27 reviewsBright Oasis in Beautiful North Fork Wine Country
Home in Southold
5.0 out of 5 average rating, 31 reviewsSalt & Sea House - Near wineries, farms, & beaches
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
Home in Southold
4.89 out of 5 average rating, 19 reviewsDockside Getaway in Southold NY
Home in Greenport
4.96 out of 5 average rating, 25 reviewsWater front 3 bedrooms 2 bathrooms beach house
Private house rentals
Home in Southold
4.93 out of 5 average rating, 15 reviewsFarm house with vineyard views
Home in Southold
5.0 out of 5 average rating, 19 reviewsHorton House
Home in Greenport
5.0 out of 5 average rating, 70 reviewsBeach House in L.I. Wine Country
Home in Mattituck
5.0 out of 5 average rating, 30 reviewsImmaculate NOFO Beach House Steps from Beach
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
Home in East Marion
4.95 out of 5 average rating, 99 reviewsQuiet, Upscale Retreat by the Beach
Home in Greenport
5.0 out of 5 average rating, 3 reviewsWaterfront Greenport Boathouse
Home in Mattituck
4.92 out of 5 average rating, 61 reviewsWalk to Breakwater Beach in Heart of Wine Country
Quick stats about house rentals in Southold
Total rentals
170 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
160 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
$100 before taxes and fees
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Martha's Vineyard Vacation rentals
- Newark Vacation rentals
- Montauk Vacation rentals
- Hoboken Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Guesthouse rentals New York
- Beach house rentals New York
- Tiny house rentals New York
- Townhouse rentals New York
- House rentals New York
- Lakehouse rentals New York
- Lighthouse rentals United States
- Guesthouse rentals United States
- House rentals United States
- Earth house rentals United States
- Townhouse rentals United States
- House rentals Manhattan
- Guesthouse rentals Manhattan
- Townhouse rentals Manhattan
- House rentals Brooklyn
- Townhouse rentals Brooklyn
- Guesthouse rentals Brooklyn
- House rentals New York
- Townhouse rentals New York
- Guesthouse rentals New York
- Treehouse rentals New York
- Tiny house rentals New York
- Rentals with lake access Southold
- Rentals with a fire pit Southold
- Rentals with a fireplace Southold
- Rentals with a kayak Southold
- Rentals with pools Southold
- Rentals with a washer and dryer Southold
- Rentals with beach access Southold
- Fitness-friendly rentals Southold
- Kid-friendly rentals Southold
- Rentals with a patio Southold
- Family-friendly rentals Southold
- Monthly Rentals Southold
- Rentals with outdoor seating Southold
- Waterfront rentals Southold
- Beachfront rentals Southold
- Pet-friendly rentals Southold
- Rentals with a hot tub Southold
- House rentals Suffolk County
- Tiny house rentals Suffolk County
- Guesthouse rentals Suffolk County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes