Luxury Vacation Rentals with a Private Pool in Monroe

Luxury Vacation Rentals with a Private Pool in Monroe

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 2 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Monroe

w/ Heated Pool, Fire Pit & Gazebo property photo 1

w/ Heated Pool, Fire Pit & Gazebo

6 bedrooms•4 baths
2,604 US dollars for 3 nights•

~$230 less than other sites

Spacious Retreat w/ Pool, Hot Tub & Great Room property photo 1

Spacious Retreat w/ Pool, Hot Tub & Great Room

7 bedrooms•4 baths
2,371 US dollars for 3 nights•

~$205 less than other sites

Welcome to private poolside luxury in Monroe

Welcome to private poolside luxury in Monroe

Discover our collection of luxury private-pool vacation rentals in Monroe, New York, where the Hudson Valley’s calm meets modern comfort. Each Wander home is meticulously operated and exactly as pictured, so you can arrive confident and relax from the first moment.
Expect sparkling private pools with generous outdoor lounging, expansive living spaces, fully equipped kitchens, dedicated workstations with ultra fast WiFi, and inspiring views. Hotel-grade touches come standard, including pristine cleaning, premium linens, smart-home details, and 24/7 concierge support.
Whether you are planning a quiet escape or a productive retreat, settle into a polished home that elevates privacy, space, and effortless downtime.

Available soon in Monroe

w/ Heated Pool, Fire Pit & Gazebo property photo 1

w/ Heated Pool, Fire Pit & Gazebo

6 bedrooms•4 baths
2,604 US dollars for 3 nights•

~$230 less than other sites

Spacious Retreat w/ Pool, Hot Tub & Great Room property photo 1

Spacious Retreat w/ Pool, Hot Tub & Great Room

7 bedrooms•4 baths
2,371 US dollars for 3 nights•

~$205 less than other sites

Featured private pool vacation rentals in Monroe

w/ Heated Pool, Fire Pit & Gazebo property photo 1

w/ Heated Pool, Fire Pit & Gazebo

6 bedrooms•4 baths
2,604 US dollars for 3 nights•

~$230 less than other sites

Spacious Retreat w/ Pool, Hot Tub & Great Room property photo 1

Spacious Retreat w/ Pool, Hot Tub & Great Room

7 bedrooms•4 baths
2,371 US dollars for 3 nights•

~$205 less than other sites

Highlights in Monroe

Discover a perfect blend of world-class shopping, rich local history, and breathtaking Hudson Valley outdoor adventures just moments from Monroe.
Museum Village
Woodbury Common Premium Outlets
Harriman State Park
Brotherhood Winery
Storm King Art Center
Bear Mountain State Park

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Monroe

w/ Heated Pool, Fire Pit & Gazebo property photo 1

w/ Heated Pool, Fire Pit & Gazebo

6 bedrooms•4 baths
2,604 US dollars for 3 nights•

~$230 less than other sites

Spacious Retreat w/ Pool, Hot Tub & Great Room property photo 1

Spacious Retreat w/ Pool, Hot Tub & Great Room

7 bedrooms•4 baths
2,371 US dollars for 3 nights•

~$205 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Monroe

Jacuzzi (2)
Hot tub (2)
Outdoor pool (2)
Outdoor shower (1)
Patio (2)
Fire pit (2)
Garden (2)
Fire place (2)
Outdoor dining area (2)
Playground nearby (1)
Hammock (1)
Washer (2)
Oven (2)
Garden view (2)
Kitchen (2)
Tv (2)

Other popular amenities & vacation types in Monroe

Hot tub vacation rentals in Monroe
Discover more beyond the pool in Monroe

Discover more beyond the pool in Monroe

Monroe places you at the bend where forested ridgelines meet glassy lakes. Morning mist drifts over Walton, Round, and Mombasha Lakes, while trailheads into Harriman State Park sit minutes away. Summer brings paddle-friendly water and leafy shade, fall lights up the hillsides, and winter swaps in crisp air and quiet.
Browse designer finds at Woodbury Common, take a scenic drive to Greenwood Lake, explore vineyard-dotted backroads near Warwick, and pause for vistas atop Bear Mountain. With tranquil neighborhoods set against rolling hills, Monroe blends small-town ease with wild open spaces. This is why Wander's luxury private-pool vacation rentals in Monroe, New York are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Monroe

Why should I book a Wander in Monroe over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.
Every home in Monroe delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Monroe?

Some of our most popular private pool vacation rentals in Monroe include 6BR w/ Heated Pool, Fire Pit & Gazebo | Sleeps 22, Spacious Retreat w/ Pool, Hot Tub & Great Room, and 6BR w/ Heated Pool, Fire Pit & Gazebo | Sleeps 22. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Monroe?

Wander offers 2 private pool vacation rentals in Monroe, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Monroe?

You can check-in to Wander private pool vacation rentals in Monroe after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Monroe have WiFi access?

Yes. Every Wander home in Monroe has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.