Vacation rentals with a pool in Monticello

5 out of 5 average rating, 103 reviews

An aerial view of BoHo Farm House showcases a modern black exterior with expansive glass panels. The garden features a swimming pool surrounded by lounging chairs and a fire pit, set against a backdrop of lush green grass and trees.

Home in Accord

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

BoHo Farm House is a luxe, modern 3BR/3BA retreat on 8 stunning acres in Accord, Hudson Valley with a large fully-fenced area for dogs & kids to roam safely. Featured in PureWow, this newly renovated Scandi farm escape includes vaulted wood ceilings, large open living space and chef’s kitchen, cozy fireplace, fire pits, and spa-like ensuite bathrooms. Close to incredible hiking, skiing, and farm-to-table dining. 5 minutes from Inness, Westwind, Arrowood, and the towns of Stone Ridge & Kerhonkson

4.97 out of 5 average rating, 159 reviews

A spacious living area features two modern armchairs with orange accent pillows facing a large picture window. The serene view of the wooded area surrounding the private pond is visible, inviting natural light into the space. A low coffee table occupies the center, complemented by a soft sofa nearby.

Cottage in Saugerties

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

Kick back and relax in this calm, stylish space, with private wildlife filled pond & cowboy pool This house is great for a family, or two couples. There are lots of relaxing spaces inside and several seating areas in nature outside. Ten minutes to the towns of Woodstock and Saugerties, you will have the perfect location to enjoy the best experiences the Hudson Valley has to offer. This 4 bedroom, 3 bath house has been recently gut renovated. Enjoy the beautiful design and natural landscape.

4.89 out of 5 average rating, 151 reviews

An indoor heated pool is featured within a cozy enclosure, surrounded by large windows showcasing tranquil winter scenery. A distinctive swan-shaped float rests on the water's surface, and comfortable seating is positioned nearby for relaxation.

Home in North Branch

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This cozy home in the woods has 3 stunning acres with creek access towards the end of the property! Enjoy a full-size heated indoor pool + an infrared sauna open year-round combined with breathtaking scenery. If you're looking for a vacation for kids + adults, this peaceful home is for you! Enjoy a relaxing vacation in a comfortable home with all the beauty that nature has to offer.

4.84 out of 5 average rating, 228 reviews

An inviting living space showcases expansive floor-to-ceiling windows, allowing natural light to illuminate the room. A cozy sofa is complemented by stylish chairs, while a large area rug unifies the seating arrangement. Dining space is visible in the background, enhancing the open floor plan.

Cabin in Swan Lake

Stunning Mountain Cabin w/ Pool & Hot Tub

This designer home is in the western Catskills, 2hrs away from NYC on 10 acres of hillside property. 20 mins from the Kartrite indoor water park. Perfect family getaway for hiking, canoeing, fishing , water sports. Quiet, secluded, fully stocked kitchen, 360 degree views , patio deck seating private heated pool from May 20- Sept 30 cabana, hammock, loungers Starting March 1st 2021, we are offering our newly installed Hot Tub/ Spa ( 5-6 seater) set into the side of hill w/ magnificent views

4.86 out of 5 average rating, 110 reviews

Home in Woodridge

Family Fun w Hot tub/Pool/Sauna near Ski Holidaymt

This Lake House getaway sits on a serene 7 acres of private land. Perfectly positioned for adventures in Sullivan County,Ny and beyond, it is an oasis of tranquility for couples, families, and friends alike. This home is a spacious six bedroom with 10 beds an extra sleeping amenities if needed.Seasonal pool, 2 Canoes, Kayak, and indoor Sauna,Pool table , and a 6 person hot tub , hikes, great restaurants, farm stands, and fresh mountain air await. Close to holiday mt skiing & catskill casino

5 out of 5 average rating, 225 reviews

The spacious living area features a large green sofa, two cozy accent chairs, and a rustic coffee table made from natural wood. A stone fireplace adds warmth, while soft lighting and large windows enhance the inviting atmosphere.

Home in Penn Estates

Enchanted Poconos Forest Escape | Movie Screen

A truly unique stay in the Pocono Mountains, home to rolling mountain terrain, breathtakingly beautiful waterfalls, thriving woodlands, + 170 miles of winding river. Created with the “ultimate night in" themed experience, guests can sip wine under the stars in a private hot tub, + enjoy movies on their own 135" movie screen equipped w/ the world's first LED 4K gaming projector. Enjoy themed bedrooms and experience a stay where the forest takes you away as you stay in ultimate comfort + luxury.

4.85 out of 5 average rating, 175 reviews

The exterior of a contemporary home is shown at dusk, with warm light emanating from large windows. Surrounded by trees, the property features a gentle incline leading to the entrance and includes several parked vehicles in the driveway.

Cabin in Lackawaxen

Large Country Home with a Beach and Skiing

The height of luxury and class. Just a short walk from the Masthope Beach or short drive to Ski Lift. Great for family reunions or a quite getaway. This luxury home features 6 bedrooms , 4 bathrooms, gorgeous open floor plan with hardwood floors, family room w/kitchenette, stone fireplace in both the living room and attached vaulted sun room and tons of natural light. Bring the whole group skiing , horseback riding or just plain relaxing. Just 2 miles from the Delaware River and canoeing.

Cabin in Livingston Manor

An inviting hot tub is positioned on a wooden deck, overlooking a spacious backyard and the tastefully designed home. Soft lighting enhances the outdoor setting as sunset hues paint the sky, creating a serene atmosphere perfect for relaxation.

4.97 out of 5 average rating, 338 reviews

Experience The Zen House

Enjoy your own private indoor movie theater with 7.1 Klipsch Premiere Surround Sound and leather recliner seats, a spa with a cold plunge pool & sauna, and a hot tub to reach the maximum level of relaxation. Play a game of ping pong, enjoy the fireplace outside and inside along with 5 acres! Amenities Include: - Hot Tub - Bath House with Sauna & Cold Plunge Pool - 12 Person Theater with immersive visual & surround sound + recliners - Game Room - Outdoor Fire Pit - Hammock & much more!

4.94 out of 5 average rating, 228 reviews

Home in Narrowsburg

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing

A modern 3BR/2BA Catskills retreat on 6 private acres with a hot-tub, and fireplace. Perched on a hill, this single-level home offers serenity, scenic views, mid-century modern decor, and comfort—ideal for girls' trips, couples and families. Amenities: Fireplace Hot Tub Spa Mini Ping-Pong Dart Board High-speed Wi-Fi Narrowsburg Offers: -Restaurants & Shops -Luxury Spas & Yoga -Alpaca Farm -Hiking -Farmer's Markets -Delaware Valley Arts Alliance Experience the best of the Catskills!

4.95 out of 5 average rating, 157 reviews

A small red cabin is framed by lush greenery, with a welcoming porch featuring two wooden rocking chairs. Natural stone path leads to the entrance, surrounded by a forest of tall trees and soft moss-covered ground.

Cabin in New Paltz

The Little Shelter at Gunks EcoLodge

Now open in Winter, but subject to refunded cancellation if Snow makes the driveway unpassable for those without 4 or all wheel drive. This rental is a small cabin in the woods of New Paltz, NY. The cabin sleeps 4 with 2 twin beds in the loft and has a pullout couch with a quality queen size mattress. The kitchen is equipped but does not have an oven. Streaming TV and Internet. Check out our other listings at the EcoLodge, with Private Rooms/Baths, on the "About Me" page.

4.95 out of 5 average rating, 391 reviews

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

Fenced & Salt Water Pool | Cozy Catskills Cottage

The perfect spot to unwind with family, friends, and pups. Spend the day hiking, visiting farms, or trying local restaurants, then come home to the yard for kid-and-dog frolicking, “Squirrel TV” through long windows. Soak in the claw-foot tub or the jetted spa tub, then gather by the fire with wine and board games. Swim and make s’mores in summer, watch snow fall in winter, and enjoy peaceful views in every season, relax, play, laugh, repeat.

4.89 out of 5 average rating, 148 reviews

A bright scene shows a refreshing pool surrounded by a wooden deck. In the background, a spacious black cabin is visible along with a game shed. Towering trees and manicured landscaping enhance the serene atmosphere of the private outdoor space.

Home in Long Pond

Resort-style Living:Pocono Estate with pool/hottub

Welcome to our secluded Poconos paradise! This enchanting Airbnb offers the ultimate escape, surrounded by a lush, tree-lined landscape that guarantees unparalleled privacy. Dive into our refreshing pool, indulge in the soothing hot tub, and let the games begin in our fantastic game shed. Unwind, rejuvenate, and create unforgettable memories. Book now for the perfect getaway in nature's embrace!😀

Popular amenities for Monticello rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 9 reviews

Home in Fallsburg

Indoor Yr round heated pool/Hot Tub/Gameroom

4.98 out of 5 average rating, 137 reviews

The exterior perspective highlights a modern Scandinavian-style home with oversized glass doors that provide a view into the inviting interior. An outdoor seating area with two chairs is visible, along with a dining table and kitchen beyond. String lights frame the scene, enhancing the ambiance.

Home in Tobyhanna

Oak View: Vintage Fireplace, Sonos Sound, Firepit!

4.81 out of 5 average rating, 165 reviews

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

TheGoshenGetawayPoolHotTubLegoLandArcade

4.91 out of 5 average rating, 153 reviews

The living room features a spacious wrap-around couch and a coffee table, creating an inviting area for relaxation. Large windows allow natural light to fill the space, while views of the surrounding trees are visible. A dining area and kitchen can be seen in the background.

Home in Penn Estates

Poconos Mountain Retreat 4BR 3BA 15 Min Camelback

4.92 out of 5 average rating, 130 reviews

Home in Pocono Summit

Lakefront,Game room, with dock, close to Camelback

4.92 out of 5 average rating, 37 reviews

A serene outdoor space features a private pool surrounded by a well-maintained garden. A koi pond with lily pads adds tranquility, while lounge chairs provide comfortable seating. Lush greenery and colorful shrubs create a peaceful atmosphere, perfect for relaxation and enjoying nature.

Home in Montgomery

Serene Hudson Valley Escape Hottub/Pool/King Suite

4.91 out of 5 average rating, 164 reviews

Home in Beacon

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

4.99 out of 5 average rating, 159 reviews

Home in East Stroudsburg

Fancy Poconos Castle & Indoor MEGA 10+ SWIM SPA

Condo rentals with a pool

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.

4.88 out of 5 average rating, 138 reviews

Valley Overlook @ Mtn Creek Resort Park & Play

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.

4.97 out of 5 average rating, 109 reviews

Cozy Retreat | Pool & Hot Tub | Mountain Creek Resort @ Appalachian

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.

4.94 out of 5 average rating, 217 reviews

Comfy Studio at Mountain Creek Resort

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.

4.94 out of 5 average rating, 920 reviews

Appalachian Lodge Top Floor w/views

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.

4.95 out of 5 average rating, 94 reviews

Comfortable, chic, modern and sophisticated condo

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.

4.8 out of 5 average rating, 302 reviews

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

The living area is highlighted by a large picture window, offering panoramic views of the slopes. A cozy couch is positioned near a modern fireplace, while a wooden dining table and chairs complete the open concept space. A wall-mounted television enhances the inviting atmosphere.

4.92 out of 5 average rating, 396 reviews

Appalachian TOP 4TH FLOOR Studio+ w/amazing views!

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.

4.93 out of 5 average rating, 181 reviews

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

Other vacation rentals with a pool

5 out of 5 average rating, 17 reviews

An inviting sunroom features large windows offering views of the surrounding nature. A spacious indoor hot tub occupies the corner, surrounded by two lounge chairs and a small blue table. Warm wood paneling enhances the cozy atmosphere, making it suitable for relaxation.

Home in Monticello

Hemlock Mntn Estate; Spacious, Indoor Hotub, POOL

5 out of 5 average rating, 32 reviews

A spacious living area features a striking stone fireplace surrounded by wooden furnishings. Large windows provide ample natural light and showcase views of the outdoors. Rustic decor elements add to the charming cabin atmosphere.

Cabin in Glen Spey

Spacious lodge w/ indoor pool!

4.95 out of 5 average rating, 65 reviews

An aerial view captures a lakeside retreat at sunset, revealing a spacious property featuring a saltwater pool, sports courts, and a dock with kayaks on the water. Surrounding trees in various shades of green create a peaceful natural backdrop.

Home in Woodbourne

Private Lakeside Retreat- Pool/2HotTub/Sauna/RV

5 out of 5 average rating, 27 reviews

Cottage in Highland Lake

SwimSpa | Sport Courts | Lake | Fishing | Firepit

4.78 out of 5 average rating, 18 reviews

The living area features contemporary furnishings, including a cozy beige sofa and comfortable armchairs. A white coffee table is centered on a soft area rug, with a television mounted on the wall. Large windows allow natural light and views of the surrounding trees.

Home in Hawley

Sunset Views over Lake Wallenpaupack

4.9 out of 5 average rating, 62 reviews

An aerial view showcases a charming retreat surrounded by lush greenery and rolling hills. The property is positioned in the center, with trees framing the landscape and mountains rising in the background under a clear blue sky.

Home in Kerhonkson

Tranquil Retreat in Kerhonkson

4.97 out of 5 average rating, 63 reviews

The pool area is surrounded by modern lounge chairs, accompanied by vibrant turquoise umbrellas for shade. Lush greenery and a well-maintained lawn can be seen in the background, enhancing the relaxing outdoor space.

Home in Middletown

5Bdrm Estate/Tennis near LegoLand