Holiday rentals with a pool in Penn Estates

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Penn Estates

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
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.
Chalet in Penn Estates
4.99 out of 5 average rating, 182 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.

Guest favourite
A spacious living area is highlighted by a stone fireplace and large windows allowing natural light. Comfortable seating is arranged around a coffee table, with a television mounted on the wall. The layout connects to an adjacent dining area, creating an open concept feel.
Home in Penn Estates
4.95 out of 5 average rating, 154 reviews

Pools, Lakes & Family Fun | Game Loft + Fire Pit

Welcome to your family-friendly Pocono escape in gated Penn Estates! • 5 bedrooms + office, 12 beds & 4 bathrooms • Vaulted living room with fireplace + 75” Smart TV • Game loft with pool table, foosball & arcade games • Kid-favorite bunk rooms with slide, toys & Legos • Fire pit, hammock, swing set & indoor sauna • Fully stocked kitchen + baby gear included • Dog-friendly + EV charger • 12 passes to pools, lakes & playgrounds Near Kalahari, Shawnee Mountain, hiking, tubing, shopping & more!

Top guest favourite
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
4.99 out of 5 average rating, 180 reviews

Simply Serene: Wild West City/Escape Room/4 Acres

✨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 ⭐

Top guest favourite
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
5 out of 5 average rating, 235 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.

Guest favourite
Chalet in Penn Estates
4.97 out of 5 average rating, 281 reviews

Hot Tub | Sauna | Lake | Firepit | Hiking

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.

Guest favourite
A spacious bathroom is equipped with a glass-enclosed shower and a sleek, black concrete soaking tub. Natural light filters through large windows, offering views of the surrounding greenery. Gray tile lines the floors and walls, while modern fixtures add a stylish touch.
Home in Penn Estates
4.89 out of 5 average rating, 160 reviews

Modern Poconos Mansion 5BR 3BA | Hot Tub | Sauna +

This is a one of a kind home custom built home, completely remodeled from the ground-up with custom finishes not found in the Poconos! This massive 5 bedroom home is not only stunning inside, but is also filled with amenities such as a outdoor 6 person hot tub, a sauna, a custom made concrete bathroom tub overlooking the forest, and has one of the largest, most breath-taking private deck with endless views of the Poconos forest that you can enjoy with seating for 12 and a propane fire pit!

Top guest favourite
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.
Home in Penn Estates
4.93 out of 5 average rating, 150 reviews

Poconos - Blue Canoe Lakefront - Fishing/Firepit

Welcome to The Blue Canoe, where lakefront luxury meets peaceful mountain escape. Set directly on a private shoreline, this Pocono retreat offers year-round adventure—kayak across calm morning waters, fish right from your private lakefront, relax at the community beach or pool, or unwind beside the water. Inside, enjoy a spa-inspired primary suite with a spacious two-person shower and relaxation room. Evenings are made for fireside gatherings and soaking in the hot tub under the stars.

Superhost
A comfortable living area is centered around a stone fireplace, adding warmth to the space. A soft rug lies on the hardwood floor, complemented by a light gray sofa and two blue accent chairs. Natural light filters through the large windows adorned with sheer curtains.
Cottage in Penn Estates
4.85 out of 5 average rating, 162 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!

Guest favourite
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.
Cabin in Penn Estates
4.9 out of 5 average rating, 134 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.

Superhost
Home in Penn Estates
4.86 out of 5 average rating, 116 reviews

Lakefront Resort w/ HotTub, Fire Pit, Games, Boats

Poconos relaxation at it's finest. Tranquility awaits at our beautiful lakefront vacation home, located just over an hour from NYC. Our Pocono lakehouse is the perfect escape for those who want to feel like they are a world away, but may not want to drive for hours to get there. Our home is situated in the Penn Estates Gated Community of East Stroudsburg. The lakehouse home feels cozy and secluded with a large, private, wooded property, with direct access to the backyard lake.

Guest favourite
Home in Penn Estates
4.88 out of 5 average rating, 145 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.

Top guest favourite
An indoor mini golf course features four holes set against a vibrant mural of mountains and colorful skies. The course is surrounded by artificial green turf, with obstacles made from wood. The ceiling is adorned with glowing accents that enhance the whimsical atmosphere.
Home in Penn Estates
4.94 out of 5 average rating, 101 reviews

OMG! Glow in the Dark Mini Golf, Pickleball, Bball

Conveniently located just minutes away from all the natural attractions that the Poconos has to offer (lakes, hiking, & more!), you will have all the amenities & entertainment you could need right here at home. Indoor mini golf, movie theater, fire pit, game room, and much more! 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!

Popular amenities for Penn Estates rentals with a pool

When is the best time to visit Penn Estates?

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Avg. price$368 SGD$359 SGD$310 SGD$282 SGD$293 SGD$318 SGD$401 SGD$424 SGD$266 SGD$286 SGD$329 SGD$389 SGD
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Quick stats about holiday rentals with a pool in Penn Estates

  • Total holiday rentals

    Explore 170 holiday rentals in Penn Estates

  • Nightly prices starting at

    Penn Estates holiday rentals start at $154 SGD per night before taxes and fees

  • Verified guest reviews

    Over 10,890 verified reviews to help you choose

  • Family-friendly holiday rentals

    170 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wifi availability

    170 of Penn Estates holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Penn Estates rentals

  • 4.8 Average rating

    Penn Estates stays are highly rated by guests – averaging 4.8 out of 5!

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