Vacation 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.
Vacation 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
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
Oct 23 – 30
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
Oct 24 – 31
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
Apr 14 – 21
Home in Cutchogue
4.96 out of 5 average rating, 74 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Oct 29 – Nov 5
Home in Cutchogue
5.0 out of 5 average rating, 24 reviewsNorth Fork paradise between beaches and vineyards
Oct 6 – 13
Home in Mattituck
4.98 out of 5 average rating, 41 reviewsModern farmhouse w/ pool, beach, horses and winery
Mar 22 – 29
Home in Mattituck
4.9 out of 5 average rating, 10 reviewsNorthFork FarmHouse, Amazing Pool, Beach, Wineries
Dec 6 – 13
Home in Greenport
5.0 out of 5 average rating, 19 reviewsThe Corwin House
May 16 – 23
Condo rentals with a pool
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
Jan 5 – 12
Condo in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
Apr 8 – 15
Condo in Greenport
4.87 out of 5 average rating, 90 reviewsWaterfront Condo C-204 at The Cliffside Resort
May 27 – Jun 3
Condo in Greenport
4.81 out of 5 average rating, 88 reviewsBeautiful condo on Long Islands Northfolk
Oct 11 – 18
Condo in Old Saybrook
4.91 out of 5 average rating, 57 reviewsSeashore getaway - CT shoreline
May 1 – 8
Condo in Greenport
4.83 out of 5 average rating, 30 reviewsTwo Bedroom Lawn Side 1st Floor Condo!
Nov 19 – 26
Condo in Shelter Island Heights
5.0 out of 5 average rating, 5 reviewsPeaceful and Relaxing Waterfront.
Mar 31 – Apr 7
Condo in Southampton
5.0 out of 5 average rating, 10 reviewsNewly Renovated Modern Townhouse w/Pool & Tennis
Jul 30 – Aug 6
Home rentals with a private pool
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
Jan 24 – 31
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Apr 4 – 11
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Jan 14 – 21
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Apr 2 – 9
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
May 15 – 22
Quick stats about vacation rentals with a pool in Southold
Total rentals
60 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
480 reviews
Nightly prices starting at
€ 168 before taxes and fees
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