House holiday rentals in Southold
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Top-rated house rentals in Southold
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Southold
House rentals with a pool
Home in Hampton Bays
4.98 out of 5 average rating, 113 reviewsBeach House Feel - newly renovated backyard Oasis
Home in East Hampton
4.93 out of 5 average rating, 141 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in Manorville
4.99 out of 5 average rating, 205 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in East Hampton
4.92 out of 5 average rating, 130 reviewsHeated pool, games room, near beach, kid-friendly
Home in Southampton
4.95 out of 5 average rating, 132 reviewsWaterview, Pool, DogsStayFree! Kayaks, PingPong
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in Sag Harbor
4.89 out of 5 average rating, 167 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
Home in East Hampton
4.88 out of 5 average rating, 101 reviewsGorgeous East Hampton Getaway
Weekly house rentals
Home in Southold
4.93 out of 5 average rating, 14 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Home in East Marion
4.92 out of 5 average rating, 24 reviewsWaterfront Bungalow w/Private Beach on Peconic Bay
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
Home in Southold
4.9 out of 5 average rating, 30 reviewsBright Oasis in Beautiful North Fork Wine Country
Home in Cutchogue
4.96 out of 5 average rating, 78 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Home in Greenport
5.0 out of 5 average rating, 38 reviewsBeachfront Greenport Villa
Home in Greenport
5.0 out of 5 average rating, 31 reviewsHistoric Stunner in Heart of Village
Home in Southold
5.0 out of 5 average rating, 32 reviewsSouthold Comfort - North Fork Getaway
Private house rentals
Home in Greenport
4.95 out of 5 average rating, 40 reviewsThe North Star: Greenport Waterview Beach Getaway
Home in Southold
4.88 out of 5 average rating, 16 reviewsLuxury by the Sea!!
Home in Greenport
5.0 out of 5 average rating, 5 reviewsWaterfront Greenport Boathouse
Home in New Suffolk
5.0 out of 5 average rating, 14 reviewsWaterfront Beach Cottage
Home in Southold
4.94 out of 5 average rating, 18 reviewsNEW LISTING: COMPLETELY RENOVATED 4-BED, 3-BATH
Home in Mattituck
5.0 out of 5 average rating, 32 reviewsImmaculate NOFO Beach House Steps from Beach
Home in Greenport
4.96 out of 5 average rating, 25 reviewsWater front 3 bedrooms 2 bathrooms beach house
Home in Greenport
4.99 out of 5 average rating, 73 reviewsBeach House in L.I. 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
€ 92 before taxes and fees
Destinations to explore
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