
Vacation rentals with a pool in Upper West Side
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Upper West Side
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

2BR/2BA Near EWR • Long Stays • Fast WiFi
Spacious 2BR/2BA near Newark Airport, ideal for long-term stays, business travelers, or relocation. Fully furnished with kitchen, cozy living area, and fast WiFi. Elizabeth Train Station is a 6 min drive/15 min walk → NYC in 30 min. All inclusive rates, no cleaning fees. Discounts for 14+ day and monthly stays. EWR Airport: 7 min drive Bus Stop: 1 min walk Trinitas Hosp: 7 minute drive Union College of Union County: 4 min drive Kean Univers: 10 min drive Local shops & eateries: walking distance

Low cleaning fee, pool,swing, EWR 7min , NYC 27min
We just know you're going to love your stay at our Luxe Glass house .Get a good nights rest on our Queen pillow top mattress. Walk into a custom mirror background including a beautiful crystal chandelier in the bedroom . Glass barn door adjacent to our Luxurious swing complimented by a bright LED sign for photos .Just 7 minutes away from EWR & 27 mins from NYC . Enjoy a beautiful city skyline view with our oversized windows ! We are dedicated to giving our Glass House guest a 5 star experience!✨

Lush Townhouse 15 mins from Times Square.
Newly renovated townhouse in the up-and-coming West New York, NJ. Easy access to the city and to all local attractions. Steps away from the bus stop. The ride to midtown Manhattan takes 15-20 min. Each bedroom has smart TV, air conditioning and ceiling fan. Fully fenced private back yard with a grill, "Solo Stove" fire pit for cold winter days, and your own pool for hot summer days. Pool has highest grade Saltwater system. 16 ft round, 52" deep, professionally cleaned and maintained weekly.

Private, cozy, one bedroom apartment close to NYC!
The Arlington House is the perfect get away, vacation home for families, friend groups, remote workers, looking to explore New York City! Easy access to trains, 15 minutes from NYC, Big Apple. Backyard, hot tub, pool, a private entrance, and an apartment in a quiet, safe, family-friendly, walkable neighborhood in Jersey City. **Travel nurse friendly We provide maps to help you get around, offer NYC tour options, Newark Airport transportation services, and menus for some of the best food!

Cozy and private studio mins to NYC/Airport
A chic and cozy stay with a great price ,1700 for monthly stays, just ask. A Queen bed & also a couch that turns into a bed! Your own entrance, outside lounge, mins from NYC,street parking. The Train station is a 5 min walk. Restaurant, bars and shopping area walking distance. Come stay in this Extra large studio which is clean and chic in an amazing, quiet neighborhood. Close to the water and several parks.food,bars, nail shops & a mall all steps away. Returning guest always get a discount.

13-Room Colonial Montclair NJ House, 30 min to NYC
Be at home in this grand historic 1906 house in Montclair. 6400 square feet - a "4 square" colonial 8 bedroom house (6 setup as bedrooms, 2 as offices), 4.5 bathrooms, 3 living areas (incl. fireplace), dining room, gourmet kitchen, excellent wifi, 4 fully furnished floors, etc. Smart TVs. Private , fenced-in yard, large covered porch. 10-minute walk to downtown Montclair: restaurants, coffee shops, movie theater, gyms, etc. Trains/buses to New York city. 30-minute drive to NYC non-rush hour.

*NEW*Luxe 2bd/2ba w/ Pool & More
After the success of our first listing, we bring our talents to Hoboken, New Jersey. Echelon Living presents a luxurious residence just off Manhattan. This 1,300-square-foot apartment features two well-appointed bedrooms, a king and a queen, plus two modern bathrooms. Explore Hoboken’s scenic waterfront, lively Pier A Park, and Washington Street’s unique shops and restaurants. Visit the Hoboken Historical Museum or stroll the Hudson River Waterfront Walkway with stunning skyline views..

Studio, Fire Pl, Spa BTR, EWR 7mins NY 27
🖤 Welcome to The BLACK AFFECT – A Luxury Studio Apartment with a Spa-Inspired Bathroom! Experience the perfect blend of comfort and convenience in the heart of Elizabeth. Our stylish studio features premium amenities, including a heated toilet seat, towel warmer, and cold water bidet, ensuring a truly relaxing stay. 10 minutes to Newark Airport(EWR), 25 mins to Penn Station, NYC (Madison Square Garden), 25 mins to Met Life Stadium. Surrounded by top-rated restaurants, shops, and malls.

Luxury apt/amenities train to NYC/EWR
Luxury apt next to train station to NYC. Cubical working areas on 1st floor. On 2nd floor pool, gym, pool table, foosball, fire pits, gas grills, large casino type sports TV, poker table, sky bar, pizza oven, and more! Across the street there is a plaza with CVS Pharmacy, Panera Bread, Chipotle, Star Bucks, Quinn’s BBQ and more. Lots of nightlife lounges, restaurants, bars, and night clubs are 5 to 15 driving distance. Ubers readily avl NYC driving distance 30 min

NOVA Stay Apartment Near Newark AirPort
A clean and simple design space. Few pieces of furniture but of high quality, neutral colors, and plenty of natural light. Ideal for those seeking a quiet retreat, yet with everything needed for a comfortable stay. A touch of contemporary art can be a nice detail. Enjoy the simplicity of this tranquil and central accommodation. We also have another listing available same location http://airbnb.com/h/demajo.

Englewood NJ Country Carriage House (15 min NYC)
Spacious eclectic luxurious renovated carriage house on 1 acre with a pool & hot tub, & a separate private 6 seat 60 jet hot tub, sauna, steam room, gas & wood burning fire pits, pool/ping pong table, trampoline & basketball court in a gorgeous quiet suburb of NYC. In 20 minutes you can be enjoying all that NYC has to offer & then come back for a sauna & steam. Great small reunion/intimate party space!

Cozy apartment near NYC 15 min
Apartment located in a house only 15 min from Manhattan. Bus stop in front of the building . Parking permit required to park on the street. Located in central area nearby restaurants, pizzeria, coffee shops, supermarkets and a laundry mat.The neighborhood is quiet . 3 spacious bedrooms . Office room, spacious living room dining room,Kitchen,pantry room and a bathroom.
Popular amenities for Upper West Side rentals with a pool
House rentals with a pool

Amazing luxury suite

Casa Bella

Luxury 4BR Home – Saltwater Pool, EV, Near NYC

Amazing suite luxury

Charming Home with Pool & Patio

Sleep 18! Free parking & only 30 min to NYC

Cozy Private Apt near NYC|Family & Pet Friendly
Other vacation rentals with a pool

Hoboken Views: Pool, Gym, PATH Shuttle Access

Luxury 2 BR Apt with Gym and Pool

Cozy 2 bed / Terrace / Pool / Gym /Grill /Rooftop

The Manhattan Club in the heart of midtown!!!!

Penthouse Condo | City Skyline View | 15m to NYC

Warm & Welcoming • Minutes from the City

Cozy & Comfy 2BR/2BA: 15 Min to NYC, 5 Min to EWR

NY Skyline | Pool Table| 3 mins to train to NYC
When is the best time to visit Upper West Side?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $256 CAD | $259 CAD | $269 CAD | $292 CAD | $325 CAD | $348 CAD | $326 CAD | $324 CAD | $331 CAD | $322 CAD | $313 CAD | $309 CAD |
| Avg. temp | 1 °C | 2 °C | 6 °C | 12 °C | 17 °C | 22 °C | 25 °C | 25 °C | 21 °C | 14 °C | 9 °C | 4 °C |
Quick stats about vacation rentals with a pool in Upper West Side

Total vacation rentals
Explore 80 vacation rentals in Upper West Side

Nightly prices starting at
Upper West Side vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 670 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
80 of Upper West Side vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Upper West Side rentals

4.6 Average rating
Upper West Side stays receive an average rating of 4.6 out of 5 from guests

Nearby attractions
Upper West Side’s top spots, include The Metropolitan Museum of Art, American Museum of Natural History, and Solomon R. Guggenheim Museum
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- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- New York Public Library Main Branch
- Grand Central Terminal
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Asbury Park Beach
- Mountain Creek Resort
- Jones Beach
- Yankee Stadium
- United Nations Headquarters
- Manasquan Beach
- Citi Field
- Fairfield Beach
- Empire State Building
- Radio City Music Hall
- Statue of Liberty
- Sea Girt Beach
- Canarsie Beach
- Rye Beach
- USTA Billie Jean King National Tennis Center
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