Holiday rentals with a pool in Stroudsburg

4.97 out of 5 average rating, 200 reviews

A spacious mountain home is framed by lush greenery, featuring a combination of wooden and stone elements. Large windows reflect the surrounding landscape, and a manicured lawn provides an inviting outdoor space. Tall trees create a natural backdrop, enhancing the peaceful setting.

Home in Lake Harmony

Mountain & Lake Escape w/ Hot Tub & Free Massages!

Our special place is close to everything for your Poconos visit! Make memories at our unique Mountain & Lake Home. Free access to a zero gravity, full body massage chair as you relax. Short walk into lake harmony beach, indoor waterpark & pools right there! Golf course right off our backyard. Skiing in only 7 minutes! Enjoy a private hot tub, full range of games & arcade systems for your family sleeping up to 10. Enjoy covered porch, gazebo, grilling, large outdoor dining & large fire pit area!

4.99 out of 5 average rating, 164 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, 218 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.

Chalet in East Stroudsburg

4.97 out of 5 average rating, 269 reviews

Sauna | Hot Tub | Fire Pit | Hiking | Skiing

Relax and unwind at this stunning Poconos vacation property. Melt your troubles away with a dip in the hot tub or experience our custom-built Finnish-style sauna. This property has been thoughtfully remodeled throughout with warm wood floors, hand crafted ceramic tiles, extra comfortable beds, and custom artistic details, creating a truly unique and luxurious feel. Relax in the spa-like bathroom, sit by the firepit, or enjoy the lakes, pools, tennis courts or other amenities in the community.

Townhouse in Tannersville

4.93 out of 5 average rating, 212 reviews

Cozy Camelback Townhome - Ski In/Out Amazing View!

Welcome to High Pass Lodge! Freshly renovated & conveniently located on top of Camelback Mountain, within walking distance ski-in/out. Indoor heated pool, sauna, hot tub, & more for guests to enjoy (included with your stay). Close to Water Parks, Big Pocono State Park, Breweries, Casinos, Pocono Raceway, Shopping Outlets, Restaurants, & more activities for any season! Enjoy the breathtaking views from the deck while grilling, or cozy up in front of the living room fireplace, and Roku TV.

Cottage in East Stroudsburg

An outdoor patio space is illuminated by string lights, featuring comfortable seating arrangements with colorful cushions. A hot tub is positioned nearby, while a large projector screen displays a movie, creating a cozy atmosphere for evening gatherings.

4.85 out of 5 average rating, 157 reviews

Cozy Lakehouse: Hot Tub/Games/Boat/Outdoor Theater

Welcome to "Casa Bianca", the most perfectly cozy lakehouse getaway for families and friends. Surround yourself with style in my beautiful home in the heart of the Poconos! My home features 3 bedrooms, 3 bathrooms, and 6 beds. It comfortably sleeps a total of 8-10 guests. Cots are available for additional guests for an added fee. The home is stylishly decorated, with all the amenities you'll want in your Poconos vacation. Enjoy the hot tub, game room, or a canoe ride in the lake!

Cabin in East Stroudsburg

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, 131 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.

5 out of 5 average rating, 126 reviews

A spacious dining area features a large wooden table surrounded by tan chairs. A blue vase filled with greenery is centered on the table. The open-concept space is complemented by a cozy yellow sofa in the background and artwork on the dark wall.

Cabin in Albrightsville

Poconos Cabin Retreat w/ Hot Tub & Fireplace

Picture this: morning coffee on an oversized deck as deer wander by, evenings soaking in your private year-round hot tub under the stars, and nights curled up by the fireplace in a home guests call “exceptionally clean and incredibly cozy.” Set in a quiet private lake community and close to top Pocono attractions, Winnie’s Retreat is your peaceful reset without giving up comfort or convenience—perfect for romantic escapes, anniversaries, and unforgettable weekend getaways.

4.87 out of 5 average rating, 110 reviews

Modern 5BR Pocono Cabin | Fire Pit, Hot Tub, Games

This 5 bedroom beauty will take your breath away! This sleek, modern home is masterfully designed from head-to-toe to give you and your friends & family the vacation of your dreams. Game room, pool table, foosball, fire pit, hot tub, and SO much more awaits for you here! 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!

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, 150 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!

Cabin in East Stroudsburg

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, 141 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.

The living area showcases a spacious layout with hardwood floors and large windows allowing natural light to flood the space. A black sofa is positioned near the double-height ceiling under a skylight, enhancing the open feel of the room. A staircase leads to additional areas.

4.85 out of 5 average rating, 227 reviews

Quiet rustic house/Jacuzzi in safe gated community

"Enjoy this beautiful spacious home that is located in a secured gated community, Indoor jacuzzi tub in the master bedroom on the second floor , the jacuzzi is a lay down tub for 2 people max .There is free parking on the premises, the driveway can hold up to 5 vehicles. The home is equipped with fast high speed WiFi that can be access all around the home." I have air conditioners in the top 2 floor bedrooms, the house stays cool in summer as well

Popular amenities for Stroudsburg rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 54 reviews

5BR | Movie Theater+Poker+Arcade+Fire Pit+Jacuzzi

Home in Tobyhanna Township

A charming lakeside home is set against a sunset sky painted in shades of pink and purple. Snow blankets the ground, leading to the welcoming front porch adorned with an American flag. The lake can be seen in the background, enhancing the serene landscape.

4.91 out of 5 average rating, 139 reviews

Lake Escape - LAKEFRONT Home - Arrowhead

A spacious deck is surrounded by tall trees and illuminated by warm string lights. Colorful seating is arranged around a central fire pit, creating a cozy gathering area. The outdoor space features a mix of natural and built elements, enhancing the relaxed atmosphere.

4.91 out of 5 average rating, 112 reviews

*Lakeside Retreat* Beach | Hot Tub | Game Room

5 out of 5 average rating, 45 reviews

Poconos Hilltop Lakehouse: Lakefront/Spa/Sauna

4.86 out of 5 average rating, 124 reviews

Home in Pocono Summit

Hot Tub, Hammocks, Fire-Pit, Sunroom, Game Room!

4.97 out of 5 average rating, 105 reviews

The exterior of the lodge showcases a wooden deck surrounded by trees, with simple outdoor seating. Soft lighting illuminates the space, inviting relaxation in a natural setting. The rustic charm of the building blends harmoniously with the surrounding forest.

Home in Gouldsboro

Poconos Lodge Retreat in Private Lake Community

4.9 out of 5 average rating, 73 reviews

Peaceful Streamside Chalet | Fire Pit | King Bed

4.8 out of 5 average rating, 149 reviews

An inviting dining area is shown with a long wooden table set for a meal, featuring dark plates and glassware. The space is filled with natural light from large windows, while stylish light fixtures and modern decor complement the open layout, seamlessly connecting to the living area.

Home in Albrightsville

The Pocono House | Hot Tub | Games | Lake Access

Apartment 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

4.86 out of 5 average rating, 21 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

Apartment in East Stroudsburg

5 out of 5 average rating, 3 reviews

Shawnee Village, Poconos, PA.-2Bd

Apartment in Tannersville

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.

4.98 out of 5 average rating, 47 reviews

Pocono Mountain Chalet | 5 Min to Waterpark | Pool

Other holiday rentals with a pool

Cabin in East Stroudsburg

A sunroom is filled with natural light from large windows, surrounded by greenery. Comfortable seating includes mid-century leather and vintage chairs. A textured area rug anchors the space, while a coffee table is adorned with decorative items, creating a warm, inviting atmosphere for relaxation.

4.8 out of 5 average rating, 61 reviews

Poconos Cabin with Woodland Views!

An inviting fire pit is surrounded by eight Adirondack chairs, situated by the lake. Soft outdoor lighting illuminates the scene as the sun sets, casting warm hues across the sky. A wooden deck can be seen in the background, nestled among trees.

4.98 out of 5 average rating, 47 reviews

Poconos Lakefront | Hot tub/Sauna, Firepit, Kayaks

4.81 out of 5 average rating, 70 reviews

The modern A-frame cabin is set against a winter landscape, featuring a soft snow-covered ground. A private hot tub sits next to an outdoor dining area, while a BBQ grill is available for outdoor cooking. The cabin's triangular roof and large windows are outlined by a serene twilight sky.

Cabin in Albrightsville

Cozy A-Frame | Hot tub, Fire place, Soak tub, BBQ

Townhouse in Tannersville

An open-concept living area features a large sectional couch arranged around a coffee table. A stone fireplace serves as a centerpiece, with a mounted television above it. Expansive windows allow natural light to fill the space, offering views of the surrounding nature.

4.96 out of 5 average rating, 254 reviews

EASTSKY CHALET - Comfort, Privacy, Knockout Views!

4.91 out of 5 average rating, 213 reviews

A log-sided cabin is showcased amidst autumn foliage, featuring a set of welcoming steps leading to the entrance. The surrounding trees display vibrant fall colors, and sunlight filters through the branches, illuminating the exterior of the home and driveway.

Cabin in Albrightsville

Cozy Pocono Cabin on an Acre

An outdoor space is illuminated by string lights, creating a cozy ambiance. The red chalet exterior features large windows and sliding doors. Comfortable seating surrounds a fire pit, set on a grassy area, providing a welcoming spot for gatherings under the night sky.

5 out of 5 average rating, 77 reviews

Pocono Cove: Hot Tub,Bar,Fire Pit,Theater,Games +!

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, 275 reviews

Getaway Dream - Hot Tub- Surrounded by Nature

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.