
Holiday rentals with a pool in Southold
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Southold
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Southold rentals with a pool
House rentals with a pool

East Hampton Home: Heated Pool, Gym, Fully Fenced

Quaint Chalet w/Salt-heated Pool

Spectacular Southampton Retreat!

NorthFork FarmHouse, Amazing Pool, Beach,Vineyards

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

4 BR Hamptons Oasis w/ Pool,Jacuzzi & Beach Access

North Fork Farmhouse with Saltwater Pool

Nassau Point, North Fork Home w/ Pool
Condo rentals with a pool

One Bedroom Apartment Nestled in the Dunes

Cliffside Resort Poolside Condo A204

Beautiful condo on Long Islands Northfork

Waterfront Elevated Bungalow - Spectacular Views

Newly Renovated Modern Townhouse w/Pool & Tennis

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Seaside Summer Escape –2BR Waterfront Condo w/Pool

A Unique Piece of Paradise, Water Front pool
Home rentals with a private pool

Explore the Water & Woods at a Relaxing Retreat
East Hampton Ranch with Access to Clearwater Private Beach

5br / 5ba; Bike to town and beach; Heated Pool

Chic Poolside Hideaway in East Hampton
Enchanting Home with Large Decks and Heated Pool
Perfect Getaway at Sunny Modern Shampton Lake House
Saltbox with Separate Poolhouse in Northwest Woods
Quick stats about holiday rentals with a pool in Southold
Total rentals
90 properties
Nightly prices starting at
$739 NZD before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
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- Rentals with outdoor seating Southold
- Rentals with beach access Southold
- Rentals with a fire pit Southold
- Family-friendly rentals Southold
- Rentals with a washing machine and dryer Southold
- Rentals with lake access Southold
- Rentals with a hot tub Southold
- Pet-friendly rentals Southold
- Rentals with a fireplace Southold
- House rentals Southold
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- Rentals with a patio Southold
- Rentals with a kayak Southold
- Beachfront rentals Southold
- Rentals with pools Suffolk County
- Rentals with pools New York
- Rentals with pools United States
- Yale University
- Charlestown Beach
- Fairfield Beach
- Foxwoods Resort Casino
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Napeague Beach
- Shinnecock Hills Golf Club
- Blue Shutters Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Jennings Beach
- Silver Sands Beach
- Cedar Beach
- Sandy Beach
- Groton Long Point Main Beach
- Ninigret Beach
- Sunken Meadow State Park
- Seaside Beach
- Wildemere Beach
- Harveys Beach