Vacation rentals with a pool in Northwest Harbor

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Top-rated rentals with a pool in Northwest Harbor

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in The Hamptons

4.9 out of 5 average rating, 188 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence and gates around pool. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

Superhost

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

Home in The Hamptons

4.87 out of 5 average rating, 209 reviews

HeatedSaltWaterPool, Walk2Beach, FencedYard4Dog

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

Superhost

A modern home is set in a lush green environment, showcasing a spacious heated saltwater pool surrounded by a stone patio. Relaxing lounge chairs are placed alongside the pool, and the house features large windows that reflect the tranquility of the yard.

Home in The Hamptons

4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe deck and huge yard. The house also features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 24-656

Guest favorite

A spacious backyard is highlighted, featuring a well-maintained lawn and a refreshing pool. Black wooden chairs surround a fire pit in the foreground, while a small shed and lush greenery can be seen creating a serene atmosphere for relaxation.

Villa in The Hamptons

4.99 out of 5 average rating, 99 reviews

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.

Guest favorite

A spacious pool area features a large swimming pool surrounded by a wooden deck. Lounge chairs are positioned along the perimeter, with vibrant flowers enhancing the outdoor setting. A decorative lamp provides soft lighting, while trees and greenery offer a natural backdrop.

Guest suite in The Hamptons

4.98 out of 5 average rating, 138 reviews

Hamptons Dream Suite

Hampton's Dream Suite- Is a guest suite in East Hampton, NY. From relaxing by the pool, to taking a day trip to Montauk, or visiting some of the best beaches in the Hamptons, the opportunities here are endless! It offers a bedroom with a Queen size Select Comfort bed, living room has two queen sofa beds and a full bathroom. It has a Kitchenette, Central AC/Heat with a 65" smart TV with surround sound and DVD, Blue ray and Xbox Games . There is also at TV and blue Ray player in the bedroom.

Guest favorite

A spacious pool area features a crystal-clear swimming pool surrounded by a wooden deck. Colorful sun loungers are arranged neatly, accompanied by large umbrellas offering shade. Lush greenery is visible in the background, enhancing the tranquil outdoor setting.

Home in The Hamptons

4.93 out of 5 average rating, 155 reviews

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

Guest favorite

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

4.97 out of 5 average rating, 159 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

Superhost

A charming guesthouse is situated near a tranquil pool. The exterior displays natural wood shingles, with large glass doors inviting light inside. Two blue lounge chairs are positioned by the pool, surrounded by lush greenery and a bamboo forest, creating a serene atmosphere.

Guesthouse in The Hamptons

4.82 out of 5 average rating, 322 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house with use of amenities (shared with our family of 4). The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, micrwave, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 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.

Guest favorite

A serene backyard scene is captured, featuring a curved in-ground heated pool surrounded by natural stone decking. Lush green grass and landscaped vegetation create a tranquil atmosphere, while the charming farmhouse is visible in the background, nestled among mature trees.

Home in The Hamptons

4.93 out of 5 average rating, 141 reviews

Walk to East Hampton Village & Ocean Beaches

Great Location! The center of East Hampton village is only 1 mile from the house where you can enjoy fabulous restaurants, wonderful shopping, or a relaxing night at the movies. Enjoy a terrific day at the ocean or evening walk on the beach - Main Beach is only 1 mile from the house-just a short walk or bike ride! If you prefer spending time at home, then relaxing by the pool and enjoying the manicured yard is the perfect way to spend the day! (The pool closes in Mid October)

Top guest favorite

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

Home in The Hamptons

4.98 out of 5 average rating, 132 reviews

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.

Top guest favorite

A serene pool area is highlighted by a clear blue swimming pool with colorful floatation devices. Surrounding the pool are lounge chairs and a shaded dining area. Lush greenery creates a private, tranquil atmosphere, enhancing the outdoor retreat experience.

Guest suite in The Hamptons

4.96 out of 5 average rating, 167 reviews

Be our guest! Central, peaceful & private pool!

Beautiful, bright, spacious King suite w fireplace, two bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book/movie! The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Guest favorite

A spacious backyard is highlighted, featuring a beautifully landscaped lawn, a heated pool, and a fire pit area with unique wooden seating. The modern home with large windows presents a stylish facade, surrounded by lush greenery under a clear blue sky.

Villa in The Hamptons

4.97 out of 5 average rating, 31 reviews

SERENITY AT SHOREWOOD Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.