
Vacation 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.

Detached bungalow w/ private bath
Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

CozyFallRetreat,Walk2Beach,FencedYard4Pup,Spotless
Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset. Easy living home.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

Amazing Home close to Everything -
Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

Montauk Cottage Escape
EH Town Rental Registry: 23-483 Escape to Montauk’s Quiet Side- Enjoy the peaceful beauty of Montauk in the off-season from this updated, spacious, comfortable home - close to town, beaches, and scenic trails. Between cozy nights in and crisp coastal walks, this is the perfect retreat for a weekend getaway or a work-from-home reset. Reliable Wi-Fi and a fully equipped kitchen make it easy to settle in for a few days—or weeks. Dogs are welcome with prior approval (Additional pet fee applies.)

Montauk Waterfront Condo w/ Sunset Views
Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

East Hampton Village Fringe, Renovated with Pool
This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool
Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Montauk Royal Atlantic Beach Resort North
My place is at Royal Atlantic Beach Resort North. The beach is across the street and can be seen from my front door. The Suite is within walking distance to town with great restaurants, live music and dancing, mini-golf, paddle boarding and sailing. You can walk the cliffs at Shadmoore State Park where you’ll see the famous hoodoos. It’s good for couples, solo adventurers, business travelers and families. No pets allowed. No smoking. Cable TV has 100 channels.

Cheerful East Hampton home with Pool
Situated off of a quiet lane on one and a half-acres of land, this amazing residence offers a peaceful and quiet Hamptons getaway. The home consists of 4 wonderful bedrooms, 3.5 modern bathrooms, a heated pool & mature landscaping. Additionally, please read my disclosures and "rules". Not a party house. No Events, parties & No smoking will be permitted. The house is beautiful, tranquil and very comfortable. THANK YOU!

Exclusive Sag Harbor Compound
A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

4 BD w/ Heated Pool in E Hampton, Fully Furnished
Rent a beautiful and spacious 4 bedroom/3 bathroom property in East Hampton with a heated swimming pool in the backyard. This three level house with large kitchen, central A/C, BBQ in the backyard, and a garage is the perfect place to entertain guests or to relax and escape in East Hampton.
Popular amenities for Montauk rentals with a pool
House rentals with a pool

Private & Pristine with Pool and Kid’s Playard

4 BR/3BA Quiet Pool Home

Peaceful Retreat in Immaculate Architect’s House

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

The Perfect Summer Beach Home in Sag Harbor

Rove Travel | Blue Jay Villa | 7BR Home with Pool

Renovated, 5BR, Private Getaway w/ Pool

3BR/3.5BA: East Hampton, Heated Pool, Hot Tub
Condo rentals with a pool

Second Floor Corner Unit Overlooking the Ocean

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Sun N Sound Resort, Montauk, NY

Beautiful condo on Long Islands Northfork

2 BR Waterfront Autumn Escape in Wine Country

Endless Summer Studio Condo w Balcony Bayview

Beautiful Waterview Condo on the North Fork of LI

Condo on the ocean in Montauk
Home rentals with a private pool

East Hampton Ranch with Access to Clearwater Private Beach

Beach Barn w/ Heated Pool & Sauna - Dog Friendly
Enchanting Home with Large Decks and Heated Pool
Perfect Getaway at Sunny Modern Shampton LakeHouse
Saltbox with Separate Poolhouse in Northwest Woods
When is the best time to visit Montauk?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 461 | € 451 | € 434 | € 246 | € 362 | € 467 | € 636 | € 677 | € 395 | € 362 | € 448 | € 474 |
| Avg. temp | -2°C | -1°C | 3°C | 8°C | 13°C | 18°C | 21°C | 21°C | 17°C | 11°C | 6°C | 1°C |
Quick stats about vacation rentals with a pool in Montauk

Total vacation rentals
Explore 400 vacation rentals in Montauk

Nightly prices starting at
Montauk vacation rentals start at € 9 per night before taxes and fees

Verified guest reviews
Over 9,330 verified reviews to help you choose

Family-friendly vacation rentals
190 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
200 properties have a dedicated workspace

Wi-Fi availability
400 of Montauk vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Montauk rentals

4.8 Average rating
Montauk stays are highly rated by guests—averaging 4.8 out of 5!
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