
Holiday rentals with a pool in Northwest Harbor
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Northwest Harbor
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Private + serene Hamptons oasis! Near attractions
Come escape to your serene, chic Hamptons home, any time of year! Just 1 block to the marina + moments to all of the best Hampton's attractions. Curl up @ the wood burning fireplace, cook in the large Chef's kitchen, stream on the 80' TV. Enjoy a BBQ + firepit under the starry sky! You will be surrounded by nature + tranquility. During summer swim all day + enjoy the Hamptons greenery + privacy poolside You will be 5-10 minutes to beaches, restaurants, shopping, Main St, cafes + so much more!

Modern Southampton Cottage | Heated Pool & Peloton
Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

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.

Large heated pool, games room, near private beach
Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (opens 04/25 and closes mid-October (there's an additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool or take a 15 min walk to private bay beach to swim and paddle board. Or drive 15mins to the Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg RR-25-399 Local taxes included

Stunning 3 bed 2 bath home W Pool
Nestled on a serene an acre off a tranquil lane, this contemporary, designer-updated residence provides an idyllic Hamptons retreat. With 3 delightful bedrooms, 2 sleek bathrooms, and a seasonal heated pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. We maintain a strict policy against events, parties, and smoking. our home and property grouds are smoke-free.

Explore the Water & Woods at a Relaxing Retreat
Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

Serene East Hampton Escape - New Outdoor Sauna
A luxurious woodland escape with massive pool, outdoor dining living and play areas, fully fenced and just minutes from EH Village & Ocean Beaches. This impeccably renovated four-bedroom, four-and-a-half-bath home offers refined comfort in a serene, private setting. Sunlight floods the expansive interiors, featuring rich luxurious finishes, a separate office, a freestanding soaking tub, and a designer chef’s kitchen with a custom dining table for ten or more.

Spacious East Hampton Getaway with Pool
This bright and comfortable 3 bedroom, 2 bath Scandinavian home awaits! Located just a 5 minute drive Sag Harbor and 10 minutes to the heart of East Hampton to enjoy beaches, shopping, restaurants and bars. The light hardwood floors create a crisp feel that you have to witness. The first floor's two guest beds open out to a lovely eat-in kitchen with dining and living rooms featuring a wood-burning fireplace and pool to check every box for year-round fun.

Greenport Beach house Mini Resort Spa & Catering
Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Beautiful condo on Long Islands Northfork
This condo is beautifully decorated and has a wonderful stone fire place. Gorgeous shiplap walls with Navy accents. There is also a new deck and wonderful dinning set outside. This unit has capabilities to be handicap accessible. Both bedroom have private bathrooms. The living room sectional opens up to a full sleeper making this condo able to sleep six people. All rooms have flat screen smart tv's.

Astounding Watermill 5 Bedroom home with Pool
Situated off of a quiet lane on a half-acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 5 bedrooms / 3 modern bathrooms offers a relaxing escape. Large open kitchen leads out to the back garden, pool and indoor-outdoor eating areas. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Dream Home with a wonderful heated pool in SH
Situated on a half-acre of land, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 4 wonderful bedrooms 3 modern bathrooms and a solar heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –
Popular amenities for Northwest Harbor rentals with a pool
House rentals with a pool

Hamptons Home w/ Salt Water Pool

Private & Pristine with Pool and Kid’s Playard

4 BR/3BA Quiet Pool Home

Winter Inquiry - 5 Bed Village Cottage Retreat

Light-filled Retreat by the Bay

Hampton Oasis with private Tennis, Pool, Theater

Central Private Bridgehampton

Serene 3 Bed 2.5 Bath House w/Heated Pool
Apartment rentals with a pool

Second Floor Corner Unit Overlooking the Ocean

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

Montauk Waterfront Condo w/ Sunset Views

Endless Summer Studio Condo w Balcony Bayview

Beautiful Waterview Condo on the North Fork of LI

Condo on the Sound - Navy Beach

Waterfront Autumn Escape in Wine Country: 2BR

Beachside Waterview 2Br Condo w/ Pool in Greenport
Home rentals with a private pool

East Hampton Ranch with Access to Clearwater Private Beach

5br / 5ba; Bike to town and beach; Heated Pool
Enchanting Home with Large Decks and Heated Pool

Southampton Quiet Private Home/Pool 6min to Villag
Saltbox with Separate Poolhouse in Northwest Woods
When is the best time to visit Northwest Harbor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £541 | £562 | £624 | £599 | £703 | £862 | £1,028 | £1,043 | £744 | £599 | £562 | £548 |
| 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 holiday rentals with a pool in Northwest Harbor

Total holiday rentals
Explore 470 holiday rentals in Northwest Harbor

Nightly prices starting at
Northwest Harbor holiday rentals start at £90 per night before taxes and fees

Verified guest reviews
Over 7,500 verified reviews to help you choose

Family-friendly holiday rentals
440 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 200 rentals that welcome pets

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wifi availability
460 of Northwest Harbor holiday rentals include wifi access

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

4.9 Average rating
Northwest Harbor stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a washing machine and dryer Northwest Harbor
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- Rentals with pools Suffolk County
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- Rentals with pools United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Point Judith Country Club
- Ocean Beach Park
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Blue Shutters Beach
- Groton Long Point Main Beach
- Cedar Beach
- TPC River Highlands
- Napeague Beach
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Amagansett Beach
- Wildemere Beach
- Sandy Beach
- Ninigret Beach
- Outer Beach at Smith Point County Park
- Groton Long Point South Beach
- Clinton Beach




