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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Guest favorite

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

4.92 out of 5 average rating, 168 reviews

Lodge style getaway 50 miles from NYC patio 207

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!

Guest favorite

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

4.96 out of 5 average rating, 134 reviews

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.

Guest favorite

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

4.85 out of 5 average rating, 623 reviews

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.

Superhost

An expansive outdoor area features a private pool surrounded by lush greenery. Shade is provided by colorful umbrellas over seating arrangements. A custom-built outdoor kitchen is visible, along with a bar seating space. The paved patio offers ample room for relaxation and entertainment.

Home in Goshen

4.81 out of 5 average rating, 165 reviews

TheGoshenGetawayPoolHotTubLegoLandArcade

TheGG is a beautiful spacious home with more amenities than one can ask for! Cooking for 10? We have options! Our double oven is perfect for holiday dinners! Not to mention our customs built outdoor kitchen and grill! Keep your kids entertained by throwing a pizza party using our beautiful stainless pizza oven! Burn those calories off in a private gym or laps in the heated pool MAY1ST Then relax in our 8per hot tub! Bring your clubs! Near by are four 18hole golf course with in a 15min drive!

Guest favorite

A spacious bedroom features a large king bed adorned with a patterned quilt and decorative pillows. Soft lighting from a bedside lamp illuminates the area, while the en-suite bathroom is visible through an open door. Neutral tones and artwork add a touch of elegance.

Condo in Vernon Township

4.8 out of 5 average rating, 300 reviews

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

The Appalachian is a true 4 season resort overlooking Mountain Creek Ski Resort/ Waterpark and other activities such as farms, mountain biking, multiple golf courses, horseback riding, and ziplining! NEAR LEGOLAND (25 min drive) Hike the Appalachian Trails, tour the wineries and enjoy Octoberfest/Spas/Pumpkin and Apple picking. This is a true 4 season resort with a heated(in winter) year-round OUTDOOR pool/hot tubs/Suana. Ski-in/out right to the main lift from the building

Guest favorite

A well-appointed studio room features a spacious king bed with plush bedding and decorative pillows. A stylish desk with a chair is positioned alongside a modern seating area, complemented by a coffee table. Natural light floods the space through large windows, enhancing the warm atmosphere.

Condo in Vernon Township

4.91 out of 5 average rating, 286 reviews

Upscale Condo Ski-In/Out Mountain Creek 1 hr NYC

Voted NJ’s #1 new host!!! Experience a grand escape in our NEW UPSCALE and LUXURIOUS STUDIO at The Appalachian Hotel at Mountain Creek, NJ. The most convenient ski-in ski-out resort, just walk to the lifts. BOOK NOW and go skiing, snowboarding, snow tubing, hot tub & heated pool swimming, mtn biking, horseback riding, hiking, golf, water park, visit farms, wineries & more! Then, relax at our super soft king bed, sleeper sofa, amazing bathroom and cozy fireplace. You'll love it!

Top guest favorite

A light-filled living area features a comfortable sofa and a blue armchair, complemented by a modern coffee table. Two framed images hang on the wall, with a large window providing views of the greenery outside.

Apartment in Vernon Township

4.96 out of 5 average rating, 118 reviews

Mountain Creek Appalachian Apartment Ski slope

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,let us pamper you with robe and slippers available for your comfy outdoor heated pool, hot tub and sauna open all year round

Guest favorite

A spacious main room is featured with high ceilings and a skylight. The kitchenette is visible alongside a dining table and chairs. A wooden coffee table sits in the living space, adorned with decorative items. Natural light flows through large windows framed by greenery.

Apartment in Chester

4.98 out of 5 average rating, 146 reviews

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 10 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.

Guest favorite

A serene bedroom space features a spacious bed adorned with cozy linens and decorative throw pillows. Geometric wall carvings in dark tones create an artistic backdrop, complemented by bedside lamps providing soft lighting. Natural light fills the room through a nearby window.

Condo in Vernon Township

4.93 out of 5 average rating, 180 reviews

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna

Ski-In-Ski-Out ! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

Top guest favorite

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

4.97 out of 5 average rating, 101 reviews

Your Summer Escape - Cozy Forest with Deck & Views

Welcome to our peaceful sanctuary, tucked away in nature's embrace! This delightful home fuses modern amenities with the beauty of the wild, ideally located near a vibrant forest filled with towering trees. Outside, nature’s wonders await. Step onto the expansive deck, where cozy seating invites you to relax and take in the mesmerizing forest views. You might catch sight of birds flitting through the canopy or glimpse wildlife roaming freely in their natural habitat.

Guest favorite

Chalet in Warwick

4.93 out of 5 average rating, 134 reviews

Mountain Luxury: Pool, Theater & Outdoor Kitchen

Permit #P25-0121 Discover the perfect blend of mountain charm and luxury on several acres just minutes from Downtown Warwick. This serene retreat features stunning Hudson Valley views, a heated pool, covered outdoor kitchen with fireplace, and elegant indoor spaces including a Great Room and cinematic media room. Enjoy wineries, orchards, hiking, skiing, and more all within 15 minutes and just one hour from Manhattan.

Superhost

A serene view of a tranquil lake is framed by tall trees at dusk. The water reflects the soft colors of the evening sky, while a grassy slope leads down to the shore. A small structure is visible to the left, enhancing the natural setting.

Cottage in Monticello

4.84 out of 5 average rating, 112 reviews

bungalow summer cottages on the lake Catskills

Catskill summer bungalow with 1950s flair 100 acre lake , tennis, full kitchen ,hiking ,all NY upstate has to offer for a weekend or all summer near casino and new water park near great country food and fairs and all the fishing and lazy days on the lake you can enjoy .Finish your night with music and spirits by the campfire plus spectacular 4th of July fireworks display