Vacation rentals with a pool in Penn Estates

Townhouse in Tannersville

A spacious living area features wooden beams and large windows, allowing natural light to illuminate the room. A cozy fireplace stands against a brick wall, complemented by two stylish lounges and a sectional sofa. Decorative artwork adds a touch of color to the walls.

4.9 out of 5 average rating, 153 reviews

Cozy and spacious place to ski, swim, and play

Ski slopes open on December 15! Bring the whole family and friends to our stylish, cozy unit, just a walk away from ski slopes, water parks, indoor pool, tennis courts, sauna, hot tub, and more. Enjoy the local villages, with the nearby hiking trails, waterfalls and breathtaking scenery, nearby casino. Indoors you have cozy living area with a wood fireplace, 3 large screen smart TVs, super fast WiFi. Get comfortable with central AC for hot weather days and a fully equipped kitchen for cooking.

4.8 out of 5 average rating, 118 reviews

Poconos Play Park Resort | Hot Tub, Bowling, Games

Welcome to your private Poconos resort! This massive 5 bedroom home has been completely upgraded to create a modern vacation experience, loaded with amenities! TWO game rooms, pool table, ping pong, air hockey, arcade games, fire pit, hot tub, bowling, frisbee golf, and so much more - all completely yours! 15 min - Delaware Water Gap, Downtown Stroudsburg 20 min - Kalahari Resort, Shawnee Mountain, Big Pocono State Park 30 min - Bushkill Falls Experience The Poconos With Us & Learn More Below!

Chalet in East Stroudsburg

The cozy outdoor area features a fire pit surrounded by several Adirondack chairs. Soft lighting from string lights enhances the inviting atmosphere of the cabin, which is illuminated from within, showcasing a spacious deck and large windows that reflect the night sky.

4.99 out of 5 average rating, 174 reviews

Poconos Treetop Lakehouse: Lakefront/Spa/Sauna

Accessible, dog-friendly, waterfront A-line with breathtaking views only 50 ft from lake. Stepless entry/shower, elevator. Newly renovated & stylishly furnished w/ 4 bedrooms, 3 full bathrooms, hot tub, sauna, gourmet kitchen, 12 person custom dining table, coffee bar, fireplace, game room w/ billiards/foosball/arcade, many outdoor games, 3 outdoor decks, Big Green Egg grill, fire pit, fire table, hammocks, many types of boats, fishing poles, work desk, high speed WiFi, 5 Smart TV’s, EV charger.

4.99 out of 5 average rating, 167 reviews

An outdoor deck features comfortable lounge furniture in shades of blue, surrounded by lush greenery. A stock tank pool is seen, offering a relaxing spot. Soft gravel pathways lead to various seating areas, creating a serene outdoor retreat on the property.

Home in Stroudsburg

Simply Serene: Wild West City, 4 acres of privacy

✨IT'S ALL ABOUT FINDING THE CALM IN THE CHAOS ✨ & making memories .. 🌿4 ACRES OF PRIVACY, TRANQUILITY & WILD WEST CHARM 🌿4 COZY BEDROOMS • 3000+ SQ FT OF PURE FUN 🏡Unique Custom Designed Retreat in the Heart of the Poconos - Stunning Nature & Wildlife yet Minutes from All Major Poconos' Attractions 💖Perfect for Any Group Size - From Romantic Getaways, to Family Reunions, Special Occasions, OR Relaxing with Friends & Loved Ones ⭐Over 100 Indoor & Outdoor FUN Activities for All Ages ⭐

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.

5 out of 5 average rating, 224 reviews

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.

The spa room features a natural stone wall with two reclining lounge chairs. Glass walls allow natural light, while plush robes hang nearby. A table holds two glasses of orange juice, offering a serene space for relaxation.

4.92 out of 5 average rating, 146 reviews

Poconos - Blue Canoe Lakefront Retreat w/Spa Room

18 in of snow!!! 10 miles to Camelback. Welcome to The Blue Canoe, where lakefront luxury meets mountain adventure. Perfectly located near premier skiing this retreat offers the best of all seasons—kayak through misty mornings, relax at the community’s beach or pool, or enjoy serene afternoons on the water. Inside, indulge in a private spa-inspired suite, complete with a spacious two-person shower and relaxation room. Evenings bring cozy fireside gatherings, hot tub soaks under the stars.

Chalet in East Stroudsburg

Large windows allow natural light to illuminate the open living space, featuring a sectional leather sofa, a round wooden coffee table, and a stone fireplace with a wood stack. A dining area with an elegant table is visible in the background, framed by greenery.

4.96 out of 5 average rating, 205 reviews

The Blue Forest Chalet: Hot tub + Firepit + Skiing

Welcome to the Blue Forest Chalet! This newly remodeled home perfectly blends chic with woodsy for the ultimate Pocono Retreat. Whether you come for adventure or just to relax, we have you covered. Unwind and indulge in an art-filled bathroom with a Japanese soaking tub or sit outside and watch the deer roam by from your private hot tub. Located in the heart of the Poconos, just minutes from excellent Hiking, Skiing, Swimming, Kayaking, Fishing, Shopping, Restaurants, Waterparks, and more.

4.89 out of 5 average rating, 214 reviews

A modern chalet is nestled within a wooded landscape, surrounded by trees shedding their leaves. An inviting pathway leads to the entrance, illuminated by soft outdoor lighting. The sky exhibits gentle hues of orange and pink as sunset approaches.

Chalet in Albrightsville

Newly Renovated! Tucked Away Precious Haven

Brand new. Renovated 2/24/2026! Newly refreshed, modern, expansive & family welcoming chalet in an amenity filled community Private 3000sqft 4bed3bath escape resting on 1.5acres with uninterrupted views into a protected woodland preserve Enjoy the sauna, new hot tub, game room, fireplace, fire pit Community offers 5lakes, 3beaches, fishing lake, 2pools, playgrounds, tennis & basketball courts Moments from bird watching, hiking, wineries, skiing, indoor waterparks, golfing & casinos

The spacious living area features a rustic stone fireplace beneath a flat-screen television. Natural light floods the space through large windows, enhancing the warm wooden tones. Comfortable seating includes a mix of armchairs and a plush sofa arranged around a coffee table, creating an inviting atmosphere.

4.89 out of 5 average rating, 133 reviews

Summit Lodge in The Poconos - Hot Tub

Kick back and relax in this newly renovated mountainside cabin. Girls weekend? Perfectly close to multiple wineries and eateries. Many adventure seeking attractions nearby. To make your stay as relaxing as possible, we provide linens, towels and paper products! **Renters must be at least 25 years of age. **All guests, including infants and children MUST be included in the guest count and may not exceed 8. **No pets please. **Please note 3 car max due to short/steep driveway.

4.88 out of 5 average rating, 141 reviews

Poconos Chalet -Kayaks- HotTub-Karaoke-Lake

Charming 5-Bedroom Getaway - 15 Minutes from Camelback! Enjoy our newly renovated home with a hot tub, projector, fireplace, and billiards table. Relax on the outdoor patio with a propane grill, and make use of our kayaks and inflatable boat at the community lake. Located close to restaurants, shopping, and 5 minutes from two community pools and sports courts for tennis, basketball, baseball, soccer, and volleyball. Nearby activities include hiking, skiing Kalahari, casino.

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.

4.91 out of 5 average rating, 153 reviews

Poconos Mountain Retreat 4BR 3BA 15 Min Camelback

Newly renovated Poconos Mountain Retreat home! House contains 4 bedrooms and 3 full bathrooms with plenty of back and side decks. The home is equipped with a new central ac and heating system with vents in each room! About a 15 minute drive to Camelback. Close to Shawnee Mountain, Tannersville Outlets, Sunset Shooting Range, Great Wolf Lodge, and all the major attractions. Less than a 12 min drive from 24 hour grocery stores, as well as bars and restaurants!

An outdoor area features a spacious deck with a hot tub at its center, surrounded by wooden fencing. Dining furniture is arranged on the deck, and decorative string lights hang overhead, enhancing the inviting atmosphere of the space.

5 out of 5 average rating, 143 reviews

Hot Tub, GameRoom, Fire Pit, Mins to Skiing, Pets

Escape to the Poconos at the Whispering Willow Lodge. Relax with family or friends at our beautifully appointed 4 bedroom + loft with plenty of space for everyone. Enjoy the outdoors on our spacious deck, have a soak in the hot tub or cozy up by the fireplace. Centrally located in Penn Estates Private, gated community which offers swimming pools, lakes, beach, tennis, volleyball & more. Minutes to skiing, water parks, shopping, rafting, hiking, and wineries.

Popular amenities for Penn Estates rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A modern living room is showcased, with large windows allowing natural light to fill the space. A comfortable sectional couch is adorned with decorative pillows, and a wooden coffee table sits nearby. A vibrant area rug adds color, while a staircase complements the setting.

4.93 out of 5 average rating, 41 reviews

Lakewalk Home, 5 BRM, Hot Tub, Game Room, Grill!

4.98 out of 5 average rating, 136 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!

A serene outdoor space is presented with a circular arrangement of blue adirondack chairs around a fire pit. Twinkling string lights hang above, illuminating the area. A wooden deck is visible in the background, surrounded by trees and scattered leaves, creating a peaceful atmosphere.

4.88 out of 5 average rating, 77 reviews

Poconos Family Retreat: Hot Tub*Fire Pit*Lake*Ski

4.95 out of 5 average rating, 154 reviews

13 Beds, 4BA, Pools, Lakes, Sauna, Game Room, EV

The exterior of the mountain chalet is showcased, surrounded by lush greenery. A spacious deck is visible, complemented by a staircase leading to the main entrance. The driveway accommodates parking, while the natural setting emphasizes the property's secluded charm.

4.91 out of 5 average rating, 64 reviews

Modern 4B Cabin w/ Gamerm & Firepit + Nr Pool&Lake

4.98 out of 5 average rating, 104 reviews

An outdoor deck is highlighted with cozy seating arrangements, including two armchairs and a loveseat, all placed on a patterned rug. Warm string lights dangle overhead, creating an inviting ambiance. A modern fire pit serves as the focal point, surrounded by seasonal plants in pots.

Home in Tobyhanna

Cozy Mtn Retreat! Luxury Hot Tub, Grill & Firepit

A decorated Christmas tree with twinkling lights and ornaments stands beside a glowing fireplace. The mantel is adorned with greenery and candles, casting a warm light across the wooden floor.

4.79 out of 5 average rating, 278 reviews

Getaway Dream - Hot Tub- Surrounded by Nature

5 out of 5 average rating, 17 reviews

Home in Albrightsville

NEW Dog-Lovers Retreat:Dog Bath-WFH-Coffee-EV Chrg

Condo rentals with a pool

A well-appointed sleeping area features a spacious bed with white linens and decorative throw pillows. Soft lighting from two bedside lamps creates a cozy ambiance. Framed nature artworks adorn the walls, complemented by patterned curtains that frame the window.

Condo at Split Rock

4.87 out of 5 average rating, 23 reviews

Ski-Side Lakefront Getaway Waterfront Serenity

The image depicts a calm lake under a clear blue sky. Gentle waves ripple across the water, reflecting the surrounding landscape, including distant trees and buildings along the shoreline. A few clouds are visible scattered in the sky, contributing to the serene atmosphere.

4.83 out of 5 average rating, 132 reviews

Lakefront 2 Bedroom Condo Lake Harmony

A ground floor covered patio features comfortable Adirondack chairs and a propane grill. A blue area rug lies beneath, and the outdoor space offers views of the pool and Big Boulder Lake beyond, framed by green trees and a clear blue sky.

4.92 out of 5 average rating, 96 reviews

Lakeview Retreat: 2 min to Ski, Fireplace

A large window frames a serene view of Big Boulder Lake, with lush greenery in the foreground and colorful boats visible on the water. Sheer curtains softly diffuse the natural light, adding a gentle brightness to the cozy living space.

4.99 out of 5 average rating, 68 reviews

Midlake Magic. Lakefront, Ski, Hike, Beach, Pool

4.91 out of 5 average rating, 46 reviews

2BR Lakefront Condo Ski Big Boulder-Mountain View

Condo in East Stroudsburg

5 out of 5 average rating, 3 reviews

Shawnee Village, Poconos, PA.-2Bd

4.98 out of 5 average rating, 47 reviews

The living area features vaulted ceilings with decorative wooden beams and a cozy fireplace. A comfortable seating area is accompanied by a coffee table, while large glass doors open to a private deck with scenic views. Stylish decor enhances the space.

Condo in Tannersville

Pocono Mountain Chalet | 5 Min to Waterpark | Pool

Other vacation rentals with a pool

An inviting outdoor seating area features a wooden deck overlooking a serene lake, framed by lush trees. A person relaxes in a dark wooden chair, holding a drink, while mist rises gently from the water's surface, enhancing the tranquil setting.

4.97 out of 5 average rating, 58 reviews

Lakefront | Hot Tub I Game RoomI Fire Pit I Kayaks

5 out of 5 average rating, 10 reviews

Pocono Cabin w/Fire Pit, Fireplace |Near Camelback

4.89 out of 5 average rating, 36 reviews

Home in Long Pond

Serene Pocono Hide Out - Game Room, Theater & Bar

A cozy dining area is showcased, featuring a wooden bench with textured pillows alongside a simple white table supported by turned legs. Gray upholstered chairs provide additional seating, with natural light illuminating the space through nearby windows.

4.98 out of 5 average rating, 63 reviews

Pocono Mountains Beautiful & Calm Family Retreat

The exterior of the home features a light blue facade surrounded by lush green trees. A set of stairs leads up to the entrance, which is framed by large windows and an upper-story round window. A gravel pathway is visible, integrating the house into the natural setting.

4.94 out of 5 average rating, 70 reviews

Quiet + Cozy 4BD-3BA|GameRoom|Firepit|DogFriendly

The cabin features a contemporary wooden façade with large vertical windows that enhance natural light. A front porch with steps and decorative shrubs offers an inviting entrance. Surrounding trees create a serene and private atmosphere, complemented by a pastel-colored sky at dusk.

4.8 out of 5 average rating, 88 reviews

Private Wooded Escape w/ Hot Tub + Fire Pit

Chalet in East Stroudsburg

5 out of 5 average rating, 82 reviews

Cozy Pocono Retreat - Hot Tub Fire Pit Family Ski

A cozy fire pit area is surrounded by brightly colored Adirondack chairs, creating a welcoming seating arrangement. In the background, the black two-story home is partially visible, complemented by strings of lights. A children's playground is located nearby, set against a wooded backdrop.