Southold rentals with pool
We found rentals with pool — enter your dates for availability
Explore Southold rentals with pools
North Fork 7 Bedroom Farmhouse Escape
Sleeps 10 · 7 bedrooms · 3 bathrooms
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Discounted Winter Rental! Hot tub, sauna, fire pit, beach, minutes to vineyards!
Sleeps 10 · 6 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
North Fork Dream Getaway, Walk to Private Beach & In-Ground Pool!
Sleeps 9 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Located in the heart of wine country/BEACHES/shops.
Sleeps 8 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
66 reviews(66 reviews)
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
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Frequently asked questions
Are there any vacation rentals with a pool in Southold?
Book one of our vacation rentals with a pool and start planning your trip to Southold. Whether you’d like to be in Greenport West, Silver Beach, The Heights or another well-known neighborhood, you’ll find the ideal poolside retreat on Vrbo.
How much does it cost to stay in a vacation rental with a pool in Southold?
A range of factors will determine how much you pay for a vacation rental with a pool in Southold, such as property size and when and how long you’re traveling. All you need to do is key in your vacation dates and preferences to find a house where you can have a splashing good time.
When is the best time to book a vacation rental with a pool in Southold?
Do some research into weather conditions during different seasons, especially if you’re thinking of somewhere with an outside pool. Also be aware of any periods with higher demand, as this will affect availability and prices. If you’re unsure about the best time to stay in a vacation rental with a pool in Southold, join some online travel communities and get advice from others.
What vacation rentals with a pool in Southold have nice views?
Houses with views of historic areas are among the types of vacation rentals with a pool you can book in Southold. If you’re searching for properties that promise a splashing good time on top of vistas worth writing home about, you’ll discover them on Vrbo.
Are there vacation rentals with a private pool in Southold?
From making whirlpools with the kids to midnight dips beneath the stars, a vacation rental with a private pool offers plenty of possibilities for fun and relaxation. If you’re headed for Southold, use our “Private pool” filter to search for properties that come with this exclusive amenity.
What are the top things to do in Southold?
The Hamptons Beaches, Orient Point County Park and 67 Steps Beach are top attractions that’ll keep the whole family occupied in Southold. There’s nothing like a fun getaway to bring everyone together, so browse our vacation home rentals in this lively destination.
Why should I book my vacation rental with a pool with Vrbo?
Booking a vacation rental with a pool with Vrbo means you’ll have the whole place for your exclusive use — your own private oasis to make a splash without any interruptions or distractions from anybody else. What’s more, our easy payment and cancellation policies allow you to alter your plans if required.