Vacation rentals with a pool in Sullivan County

5 out of 5 average rating, 3 reviews

A plunge pool is set within a wooden deck, surrounded by sun loungers. Lush greenery and trees provide a serene backdrop, with a hint of a grassy area in the distance. Potted plants add a natural touch to the outdoor space.

Home in Livingston Manor

Livingston Manor Retreat

Only 2 hours from NYC, 5 minutes from the popular Catskills town, Livingston Manor, you’ll find this designer home and nature retreat. The home is filled with windows overlooking the wooded backyard, and a gurgling stream going off in the distance. Glass doors take you out to the sprawling patio that hosts a large dining table, solo stove, sun loungers and a plunge pool for the hot summer days. The house is designed as a calm retreat with daily luxuries and a social space for family and friends.

4.97 out of 5 average rating, 121 reviews

A spacious outdoor pool is surrounded by lush greenery and a protective fence. Sun loungers line the perimeter, offering seating for relaxation. Guests can be seen enjoying the pool area, which features slides and varying depths, under a partly cloudy sky.

Chalet in Lackawaxen

Serene Mountain Haven at Masthope

Masthope Mountain Community, is a beautiful community and our home is ready to welcome you no matter what the season. By winter you can ski, snowboard and snow tube, or just cozy up to the gas fireplace and stay warm. By summer you can enjoy the peaceful surroundings on the porch, WALK down to the lake for a swim, enjoy one of the two community’s pools or just relax at the Tiki Bar. AMENITIES WILL NOT BE AVAILABLE TO RENTERS JULY 4, 5,6 &7th (This includes but not limited to pool/beach/lake)

4.95 out of 5 average rating, 202 reviews

A modern home is viewed from the edge of a heated pool, surrounded by a fenced patio area. Comfortable outdoor seating is present near vibrant flower arrangements. Lush green fields and a clear blue sky provide a scenic backdrop to the tranquil setting.

Home in Narrowsburg

Modern House with Private Pool, Hot-Tub, Fireplace

A modern 3BR/2BA Catskills retreat on 6 private acres with heated pool, hot-tub, and fireplace. Perched on a hill, this single-level home offers scenic views, mid-century modern decor, and comfort—ideal for girls' trips, couples and families. Amenities: Private Heated Pool Fireplace High-speed Wi-Fi Modern kitchen Grill A/C Narrowsburg offers: -Restaurants & Shops -Luxury Spas & Yoga -Alpaca Farm -Hiking -Farmer's Markets -Delaware Valley Arts Alliance Experience the best of the Catskills!

Guesthouse in Loch Sheldrake

An aerial view captures the property, showcasing its expansive manicured lawns and two private ponds. The main house is situated centrally, surrounded by trees and outdoor seating areas, with pathways leading to the water's edge. The landscape reflects a serene and natural setting.

4.96 out of 5 average rating, 27 reviews

Magical Catskills Guesthouse. Pool & private lake!

One-of-a-kind magic in the Catskills at “Casa del Monte” — a secluded, luxuriously appointed living space on 10 manicured acres of private land and water. Lake swimming, kayaking, paddleboarding and fishing on property! 5-minute walk from Loch Sheldrake lake and 15-25 minutes’ drive from the area's finest hiking, F&B, and entertainment — including Livingston Manor, Mountaindale, Callicoon, Roscoe, Beaverkill River, Willowemoc, Napanoch, White Lake, and Bethel Woods. 45 minutes from Woodstock.

4.88 out of 5 average rating, 121 reviews

An indoor heated pool area features large windows allowing natural light to fill the space. Surrounding the pool are loungers, a colorful floating swan, and a bright orange inflatable, creating a cheerful atmosphere. Wood paneling and a beamed ceiling complete the inviting setting.

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.

4.83 out of 5 average rating, 202 reviews

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

Cabin in Livingston Manor

4.97 out of 5 average rating, 307 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 - Hammocks and much more!

4.92 out of 5 average rating, 39 reviews

The exterior of the retreat showcases a modern structure set amidst lush greenery, featuring a fenced pool area with lounge seating and an umbrella. An upper balcony overlooks the vibrant pool, creating an inviting outdoor space for relaxation.

Home in Narrowsburg

Garden Villa | Pool + Hot Tub + Lake Passes + Chic

Welcome to our secluded retreat in Narrowsburg, just two hours from NYC. Enjoy the beauty of blooming trees & relax by the sparkling pool, surrounded by vibrant gardens. Enjoy dining al fresco at the large table under cafe lights. Evenings are perfect for roasting s’mores around the fire pit under a starlit sky. Explore nearby Bethel Woods & local wineries, & take advantage of four seasonal passes to Lake Superior State Park, just 15 minutes away. Create unforgettable summer memories with us!

4.75 out of 5 average rating, 102 reviews

An outdoor deck showcases a round swimming pool surrounded by lounge chairs. Soft lighting lines the perimeter, enhancing the natural setting with greenery in the background. A peaceful ambiance is created as evening approaches.

Home in Roscoe

Roscoe Haven

Situated on 1 acre of land, 2 hours from NYC, Roscoe Haven is a private oasis. 4 bedrooms & 3 bathrooms comfortably sleep up to 14 guests. Indoor game room features large screen TV, the fully stocked kitchen & dining room w/ indoor fireplace provide a cozy atmosphere. Backyard & deck overlook a flowing stream. Seasonal swimming pool, year-round hot tub, outdoor deck w/seating areas, BBQ, fire pit, play set & ample parking. Perfect for families, friends & couples seeking a peaceful getaway.

4.98 out of 5 average rating, 53 reviews

Cabin in Parksville

20 Acres Luxe Swimming Pond Cabin+Game Rm, Hot Tub

New: Dock, kayaks, water toys coming soon to our private swimming pond! Hunter House is a 5-star, 3,500 sq ft Catskills getaway on 20 private acres with a lake, hot tub, mountain views, and huge game room. Luxe Primary Suite, chef’s kitchen, cozy fireplace, and more. Enjoy lakefront hangs, stargazing, and nonstop fun. Family-friendly and fully stocked. 2 extra full size air mattresses + 2 pac n plays with mattresses available on site. Follow @stayhunterhouse for updates and offers!

4.94 out of 5 average rating, 206 reviews

A wooden deck is presented, featuring two floral-patterned lounge chairs positioned beside a circular blue swimming pool. Potted plants are arranged near the steps, surrounded by lush greenery and forested surroundings, creating a peaceful outdoor retreat.

Cabin in Eldred

Quiet Modern Cabin in the Woods w Hot Tub

This 3 acre hidden gem is tucked away in the woods of the Catskills. It's a wonderful getaway from the city or any bustling lifestyle. The outdoor fire pit and hot tub are both the perfect settings for serenity. When you come up here you can enjoy hiking, cooking, swimming or simply lounging & listening to our record collection and watching nature exist around you. Our house is about 20 minutes from Big Bear mountain which is a great (small) mountain for skiing and tubing.

4.98 out of 5 average rating, 119 reviews

Cottage in Eldred

Bella Cottage w/Pool, BBQ - Catskill Getaway

Pool is now open! Pool temperate is set to 84 degrees Disconnect, relax and rejuvenate in this cute country home! Enjoy the serene, wooded surroundings as you watch deer trot by and end your day unwinding under starlit night skies. This 2-acre gem is tucked away on a private drive, just off the main road. Though secluded, grocery stores and restaurants are just down the street. The house is equipped with all the modern amenities to make your stay comfortable.

Vacation rentals for every style

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Popular amenities for Sullivan County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.76 out of 5 average rating, 50 reviews

An aerial view captures a private heated pool surrounded by a spacious patio, featuring several light blue umbrellas and lounge chairs. Lush greenery borders the area, enhancing the outdoor environment. The pool's clear water reflects the sky above, inviting relaxation.

Home in Swan Lake

Hilltop Hideaway | Hot Tub • Heated Pool • Golf

ZachRating, 5 stars2 months ago

My friends and I were looking forward a relaxing weekend getaway and we found it! This house has incredible amenities with ample space for a large group. We loved the hot tub, fire pit and the projector in the basement allowed us to have a home theater!

5 out of 5 average rating, 12 reviews

A spacious living area features a large, U-shaped sectional sofa adorned with decorative pillows. A round wooden coffee table sits on a plush rug, and large windows allow natural light to fill the room. A prominent wall art piece displaying the word 'LOVE' adds a charming focal point.

Home in Lackawaxen

Stylish Masthope Ski/Lake House

CassieRating, 5 stars4 months ago

We had a wonderful and relaxing stay for our Ski Big Bear vacation. Walking in, we felt right at home. We enjoyed playing games, watching TV and relaxing by the fire. The house was nicely decorated, clean and had plenty of towels for a family of 4. We highly recommend!

5 out of 5 average rating, 25 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/HotTub/Sauna/RV

EvgheniaRating, 5 stars3 weeks ago

We had such a great stay! The house was perfect~spacious, clean, and full of charm. There was so much to do, from swimming to hiking and everything in between. Whether we were relaxing by the pool or out exploring nature, this place had it all. It’s the kind of spot where you can truly unwind and have an adventure. Highly recommend~would love to come back soon!

5 out of 5 average rating, 17 reviews

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

FabiolaRating, 5 stars3 days ago

The house is beautiful, the area is quiet and pretty, my children enjoyed the pool and the playground. Andrea was always very kind and attentive, she responds very quickly to any questions.

5 out of 5 average rating, 35 reviews

An inground heated pool is surrounded by a concrete patio and lush green grass. Adjacent lounge chairs await relaxation under the sun, while a dining area beneath a canopy offers a shaded retreat. The tranquil backdrop of trees creates a serene atmosphere.

Home in Glen Spey

Modern Woodland Oasis w/ Hot Tub, Fire Pit & Pool

HelenRating, 5 stars3 days ago

Gabe is an awesome host and the house is a perfect oasis in the woods! Highly recommend staying here.

4.93 out of 5 average rating, 45 reviews

The three-story farmhouse is showcased from the perspective of the pool, reflecting the structure’s exterior and surrounding trees in the clear water. The house features multiple decks and stairs leading from the pool area, inviting guests to explore the outdoor space.

Home in White Lake

Spacious, Cozy Catskills Getaway with Heated Pool

EricRating, 5 stars5 months ago

Two-family get-together over a holiday weekend; one from Boston, the other Baltimore, meeting in the middle. Tyson was a terrific host. The property was lovely and exactly as expected. Everyone had a great time. Success all around!

4.83 out of 5 average rating, 29 reviews

Home in Liberty

Maison Liberty w/pool, hot tub, firepit and more

QueenieRating, 5 stars4 months ago

This was a great place to stay. Kitchen was fully stocked and the guests were quickly responded whenever needed.