Holiday rentals with a pool in Montauk
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Montauk
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 Montauk rentals with a pool
House rentals with a pool
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
18–25 Jul
Home in East Hampton
4.88 out of 5 average rating, 101 reviewsGorgeous East Hampton Getaway
23–30 Nov
Home in Southampton
4.95 out of 5 average rating, 132 reviewsWaterview, PoolOpenNow! DogsFree+Kayaks+PingPong
26 May – 2 Jun
Home in Southampton
4.88 out of 5 average rating, 193 reviewsSecluded Southampton Luxury Estate. 286
20–27 Sep
Home in Montauk
4.98 out of 5 average rating, 55 reviewsMontauk Home: Pool, Backyard Oasis + Private Beach
15–22 Oct
Home in Montauk
4.94 out of 5 average rating, 32 reviewsHeated Pool Open 5.1.24 - Private West Lake
28 Dec – 4 Jan
Home in Montauk
5.0 out of 5 average rating, 34 reviews3 BR/Pool. Walk to Beach & Town!
7–14 Jan
Home in East Hampton
4.86 out of 5 average rating, 76 reviews4 BD w/ Heated Pool in E Hampton, Fully Furnished
11–18 Sep
Apartment rentals with a pool
Apartment in Greenport
4.83 out of 5 average rating, 145 reviewsSound front condominium
5–12 Jun
Apartment in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
4–11 Nov
Apartment in Greenport
4.9 out of 5 average rating, 108 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
20–27 Oct
Apartment in Greenport
4.92 out of 5 average rating, 125 reviewsBeautiful Waterview Condo on the North Fork of LI
19–26 Apr
Apartment in Montauk
4.74 out of 5 average rating, 39 reviewsThe Exclusive Resort in Montauk
18–25 Aug
Apartment in Montauk
4.88 out of 5 average rating, 17 reviews1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!
17–24 Oct
Apartment in Montauk
4.82 out of 5 average rating, 87 reviewsBeautiful Condo on the Ocean Bluffs
23–30 Mar
Apartment in Montauk
4.81 out of 5 average rating, 26 reviewsMontauk Sunsets
14–21 Oct
Home rentals with a private pool
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
4–11 Apr
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
1–8 Jan
Home in East Hampton
4.77 out of 5 average rating, 13 reviewsHistorical Estate Home with Backyard Pool
23–30 Jan
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
7–14 Apr
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
1–8 Jan
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
8–15 May
Quick stats about holiday rentals with a pool in Montauk
Total rentals
360 properties
Wifi availability
360 properties include access to wifi
Rentals with dedicated workspaces
190 properties have a dedicated workspace
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
180 properties are a good fit for families
Total number of reviews
6.4K reviews
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