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Vacation rentals with a pool in Orange County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Orange County

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

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Top guest favourite
A tranquil outdoor pool is surrounded by colorful autumn trees, showcasing shades of yellow and orange. The three-story building, featuring a mix of warm colors, stands in the background with several balconies visible. Lounge chairs are arranged neatly around the pool area.
Condo in Vernon Township

Discounted 1 Bed *patio closed during construction

Welcome to the Appalachian! This 1 Bedroom 1 Valley View private unit sleeps 4 and is located within Mountain Creek Resort. A great spot to enjoy year round activities; Winter- true Ski-in/Ski-out hotel steps to the main lift! Summer-on site Waterpark, downhill/XC mountain biking, zip lining, horseback riding, wineries, farm stores, hiking the Appalachian trail as well as a beautiful state parks. 7 public golf courses. Fall-Pumpkin/apple picking, fresh cider donuts, beer and concert festivals!

4.93 out of 5 average rating, 191 reviews
Superhost
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

4.81 out of 5 average rating, 136 reviews
Superhost
A spacious backyard features a heated pool surrounded by a stone patio, overlooking the scenic lake. Vibrant fall foliage adorns the landscape, and the serene water reflects the clear sky. A cozy home is visible, nestled against the lush greenery.
Home in Greenwood Lake

Luxury Villa w Lake View & Private Heated Pool

Greenwood Lake Outlook, top-rated luxury getaway - 1 hour from NYC. Newly renovated home, surrounded in serene nature with stunning lake views & many amenities. Kids & pets friendly. Close to ski resorts. Fun all seasons. A few guest review highlights: ✭✭✭✭✭ This was the best Airbnb we’d ever stayed in. ✭✭✭✭✭ Words can’t describe how beautiful the house and the views are. ✭✭✭✭✭ If I could give this place 10 stars, I would!!! ✭✭✭✭✭ This is a true vacation resort to enjoy to the fullest.

4.91 out of 5 average rating, 116 reviews
Guest favourite
A scenic view from the steps leading down to the backyard, showcasing a heated pool surrounded by a fenced patio and a newly installed hot tub. Lush green lawn and vibrant flowers complement the serene lake visible in the background, providing a tranquil outdoor atmosphere.
Home in Monroe

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

4.96 out of 5 average rating, 141 reviews
Top guest favourite
Home in New Windsor

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King

Welcome to The Storm King Farmhouse! Experience the best of upstate living in this beautifully renovated 1800s farmhouse located 50 mi from NYC. The property features a heated pool, Finnish sauna, premium hot tub, pickleball & basketball court, fire pit, pond, and more! Located close to exciting Hudson Valley activities - Storm King Art Center (1 min), West Point (15 min), Legoland (25 min), hiking trails, breweries, etc. This is the perfect place to relax with family & friends! Pet friendly!

5.0 out of 5 average rating, 105 reviews
Top guest favourite
A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.
Loft in Cornwall

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

4.85 out of 5 average rating, 699 reviews
Top guest favourite
Chalet in Warwick

Mountain View Retreat w/ Hot Tub, Theater, and Gym

Thoughtfully designed, this secluded retreat is nestled on 12 acres of picturesque land in Warwick, NY. The exquisite home offers the perfect blend of luxury and tranquility, making it an ideal getaway for families and friends. Highlights include: -Huge deck with mountain views -115" 4k projection theater w/ seating for 10, wet bar, & popcorn machine -Hot tub w/ seating for 7 -Gym w/ indoor endless lap pool, Peloton bike, and yoga equipment -Game room w/ billiards & Pac-man -Gourmet kitchen

4.99 out of 5 average rating, 186 reviews
Top guest favourite
Condo in Vernon Township

Mountain Creek Appalachian Condo Waterpark

Relax in the most convenient Condo in Appalachian Hotel with the whole family at this one bedroom apartment, peaceful place to stay. All amenities Resort just at walking distance to Mountain Creek Ski Slope!!, 1st Floor one bedroom apartment just in front of the pool , jacuzzi and sauna facilities! Ski lift Sugar quad is close to the condo’s backyard,cable tv. As of March 2026, The Appalachian started a garage renovation project and also includes the small parking area up top.

4.96 out of 5 average rating, 162 reviews
Guest favourite
An inviting backyard features an inground pool surrounded by a spacious patio area. Loungers are positioned alongside the pool, and a diving board extends over the water. A fenced perimeter provides privacy, with lush greenery adding a natural backdrop.
Home in Sussex

Mountain Creek sanctuary pool & hot tub

⸻ Welcome to The Spruce, a privately owned, modern farmhouse retreat less than 5 miles from Mountain Creek Ski Resort in Vernon, NJ. Relax in your private backyard oasis with a fenced-in pool, 6–7 person hot tub, two decks, BBQ grill, and outdoor fireplace. Explore nearby wineries, breweries, farms, and the charming town of Warwick, NY—just 15 minutes away. Whether you’re visiting for adventure or relaxation, The Spruce offers the perfect balance of comfort and luxury.

4.94 out of 5 average rating, 115 reviews
Guest favourite
A serene pool area features a deep blue unheated swimming pool with steps leading in. A gazebo, softly illuminated by string lights, is nestled among lush greenery in the background. The natural landscape creates a tranquil retreat.
Apartment in Chester

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 15 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

4.97 out of 5 average rating, 184 reviews
Guest favourite
Home in Beacon

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Welcome to Hudson Valley Hideaway — a Modern stylish family friendly home in Beacon, NY, just 1.5 miles from downtown and the train. Bright, stylish home with 4 bedrooms, w/ 1 King bedroom, 2 queens and a Twin XL, stocked kitchen, and cozy living spaces. Enjoy a private fenced backyard retreat with pool, hot tub, fire pit, and grill. Perfect for relaxing or exploring the Hudson Valley, with easy access to Route 84 and local attractions.

4.92 out of 5 average rating, 180 reviews
Top guest favourite
Cabin in Montgomery

Historic Cabin with Pool and Fire Pit

Escape to our 100-year-old renovated cabin in the Hudson Valley, a perfect romantic getaway for two. This cozy retreat blends rustic charm with modern comforts like A/C and Wi-Fi. Enjoy panoramic pond views and shared access to a summer pool, fire pit, and BBQ. Perfectly situated between Beacon and New Paltz for exploring the region's best hiking and wineries. Your private, charming base for adventure awaits!

4.94 out of 5 average rating, 105 reviews

Popular amenities for Orange County rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
An aerial view of a house is surrounded by dense green trees, with a clear pool visible in the backyard. The lawn is lush and includes a pathway leading to the pool area, blending harmoniously with the natural landscape.
Home in Warwick

Beautiful Retreat w/Pool, Hot Tub & Fire Pit, 6 BR

4.91 out of 5 average rating, 144 reviews
Top guest favourite
A spacious backyard is featured, showcasing vibrant green grass and a large tree offering shade. The well-maintained landscape includes a gazebo and patio area, creating a serene outdoor space. Various shrubs and plants are arranged around the property, enhancing the natural surroundings.
Home in Port Jervis

Your Summer Escape - Cozy Forest with Deck & Views

4.96 out of 5 average rating, 114 reviews
Top guest favourite
A two-story home with a light-colored exterior and burgundy shutters is set against a clear blue sky. The well-maintained lawn features manicured shrubs and trees, enhancing the inviting curb appeal. The entrance is framed by steps leading to the front door, creating an approachable feel.
Home in Chester

4 Bedroom Home with Hot-Tub

5.0 out of 5 average rating, 57 reviews
Guest favourite
A serene outdoor setting features a sparkling swimming pool surrounded by lush greenery. Comfortable seating areas, including deck chairs, are positioned nearby. Hammocks hang between trees, providing a relaxing retreat. Scenic views of the Hudson River and mountains enhance the tranquil atmosphere.
Home in Philipstown

Arkadia House Mid-century retreat with pool & view

4.88 out of 5 average rating, 50 reviews
Guest favourite
Home in Slate Hill

The Wooden Igloo Near Legoland NY

4.96 out of 5 average rating, 24 reviews
Top guest favourite
An aerial view of a spacious property reveals a large house with a deck and a fenced saltwater pool. The expansive green lawn is bordered by trees, creating a serene atmosphere. The property is surrounded by ample open space, ideal for outdoor activities.
Home in Warwick

The Hilltop • Fenced 8-Acre Dog-Friendly Retreat

4.98 out of 5 average rating, 87 reviews
Guest favourite
Home in Sparrow Bush

Villa on the Hill

4.93 out of 5 average rating, 15 reviews
Guest favourite
A single-story home is set amidst trees and greenery, featuring a front porch with a railing. A driveway leads to a two-car garage. An American flag is displayed near the entrance, while a fenced area is visible in the background, highlighted by a bright blue sky.
Home in Sparrow Bush

3BR Home with Pool & Private Acreage

4.98 out of 5 average rating, 40 reviews

Condo rentals with a pool

Top guest favourite
A spacious living area features a cozy sofa adorned with a throw blanket, set against a stone fireplace. A flat-screen TV is mounted above the fireplace. Nearby, a small dining table with two chairs sits near large windows that offer views of the outdoors.
Condo in Vernon Township

Appalachian Lodge Top Floor w/views

4.94 out of 5 average rating, 950 reviews
Top guest favourite
Condo in Vernon Township

Modern, Upscale Condo at Mountain Creek 1 hr NYC

4.9 out of 5 average rating, 332 reviews
Guest favourite
A spacious living and dining area features a large wooden table surrounded by chairs, with a cozy seating arrangement across from a fireplace. Large windows offer natural light and a view of the outdoors, enhancing the inviting ambiance of the space.
Condo in Vernon Township

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5

4.95 out of 5 average rating, 129 reviews
Guest favourite
The exterior of the Appalachian building is shown, featuring a combination of vibrant wood siding in warm hues and decorative green shutters. Balconies are visible, nestled among well-maintained landscaping, creating a welcoming entrance leading to the facility.
Condo in Vernon Township

Comfy Studio at Mountain Creek Resort

4.93 out of 5 average rating, 227 reviews
Guest favourite
A cozy living area features a comfortable sofa accompanying a rustic coffee table. A large window showcases mountain views, while natural light enhances the space. A wall-mounted television is placed above a gas fireplace, with minimalist decor elements positioned for a welcoming atmosphere.
Condo in Vernon Township

Cozy Retreat | Pool & Hot Tub | Mountain Creek Res

4.97 out of 5 average rating, 112 reviews
Guest favourite
An illuminated salt-water pool reflects soft light at night, surrounded by a well-maintained patio. The backdrop features a multi-story building with balconies and warm lights glowing from the windows, creating a serene atmosphere.
Condo in Vernon Township

Valley Overlook @ Mtn Creek Resort Park & Play

4.88 out of 5 average rating, 146 reviews
Top guest favourite
A cozy bedroom featuring a spacious bed with white bedding and decorative pillows. Two bedside tables with lamps flank the bed, providing soft lighting. A textured wooden accent wall adds warmth to the space, complementing the neutral tones of the room.
Condo in Vernon Township

Walk to Waterpark! Open Through Labor Day!

4.98 out of 5 average rating, 354 reviews
Guest favourite
The living room features a cozy sectional sofa and a wooden coffee table positioned in front of a modern electric fireplace. A flat-screen TV is mounted on a textured wall, displaying various streaming options. A dining area with a table and chairs is visible, creating a welcoming space.
Condo in Vernon Township

Mt Creek | Walk to Water Park | Pool & Hot Tub

4.95 out of 5 average rating, 103 reviews

Other vacation rentals with a pool

Top guest favourite
A spacious bed is centered against a soft green wall, adorned with pillows and a decorative fur throw. Two tall lamps with silver bases provide gentle lighting, while a floral artwork piece hangs above the headboard, adding a subtle touch of elegance.
Townhouse in Vernon Township

Country Chic Getaway at Black Creek Sanctuary

4.93 out of 5 average rating, 296 reviews
Top guest favourite
The exterior of The Appalachian Hotel showcases a charming combination of red and yellow hues. The building features a pitched roof and multiple balconies. In the foreground, a clear blue pool reflects the evening sky, while landscaped greenery surrounds the area.
Apartment in Vernon Township

Mtn. Creek Heated Pool HotTub Sauna Fire Place

4.96 out of 5 average rating, 130 reviews
Guest favourite
A large historic home is visible in the background, featuring multiple stories and a wraparound porch. Lush green trees frame the property, and a serene swimming pool reflects the clear blue sky. Comfortable lounge chairs are positioned on the poolside for relaxation.
Villa in Goshen

Goshen Retreat w/ Hot Tub & Pool near Legoland

5.0 out of 5 average rating, 24 reviews
Guest favourite
A spacious outdoor area features a large swimming pool surrounded by a paved patio. The villa, with a red-tiled roof, stands in the background amidst lush greenery. Sun loungers are arranged at the pool's edge, inviting relaxation.
Villa in Monroe

Mediterranean villa •pool•hot tub•fire place

4.94 out of 5 average rating, 71 reviews
Top guest favourite
A tranquil outdoor space features a modern pool area surrounded by lounge chairs and potted plants. Soft lighting highlights the inviting seating beneath a covered patio. The backdrop includes a dark-colored cottage, with warm lights illuminating the entrance.
Guesthouse in Tomkins Cove

The cottage at Oasis Cove

4.89 out of 5 average rating, 36 reviews
Top guest favourite
A rustic log cabin is nestled among trees, surrounded by autumn foliage. Large windows reflect the exterior landscape, while a gently winding pathway leads to the entrance. The warm tones of the wood blend with the natural setting, creating a serene atmosphere.
Cabin in Sparrow Bush

Cheerful Log Cabin for memorable family moments.

5.0 out of 5 average rating, 60 reviews
Top guest favourite
An expansive snowy landscape is visible, showcasing a covered field bordered by a wooden fence. In the background, mid-century farm buildings are seen nestled among leafless trees. The distant hills contribute to the serene rural setting under a cloudy sky.
Guest suite in Warwick

Green Pond Farmhouse Downstairs

4.97 out of 5 average rating, 58 reviews
Superhost
Guest suite in Goshen

The 5-Star Pool Retreat-5 Mins from Legoland!

4.77 out of 5 average rating, 35 reviews

Destinations to explore