Luxury Vacation Rentals with a Private Pool in Maryland

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 3 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Maryland

Apartment in Ocean City

3 bedrooms•2 baths

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Apartment in Ocean City

2 bedrooms•2 baths

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Apartment in Ocean City

2 bedrooms•2 baths

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Welcome to private poolside luxury in Maryland

Choose a better way to stay in the Old Line State. Wander’s luxury private pool vacation rentals in Maryland fuse the polish of a five star hotel with the privacy of a beautifully designed home. In Baltimore, our residences are meticulously operated so the experience always matches the photos.

Settle into sunlit living rooms, chef-ready kitchens, and suites dressed in premium linens, then slip outside to your own pool for uninterrupted downtime. Expect ultra fast WiFi, dedicated work setups, spotless housekeeping, and attentive 24/7 concierge support. Whether it is a focused work trip or a celebratory weekend, your private pool retreat is ready when you are.

Available soon in Maryland

Apartment in Ocean City

2 bedrooms•2 baths

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All homes in Maryland

Apartment in Ocean City

3 bedrooms•2 baths

•

Apartment in Ocean City

2 bedrooms•2 baths

•

Apartment in Ocean City

2 bedrooms•2 baths

•

View all homes

Highlights in Maryland

From historic coastal towns and sandy beaches to rich maritime heritage and mountain lakes, Maryland offers diverse adventures for every traveler.

National Aquarium

Ocean City Boardwalk

Fort McHenry National Monument

Annapolis Historic District

Assateague Island National Seashore

Deep Creek Lake

Antietam National Battlefield

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.

Most popular amenities for private pool vacation rentals in Maryland

More popular private pool destinations in Maryland

Private pool vacation rentals in Baltimore

Other popular amenities & vacation types in Maryland

Family vacation rentals in Maryland

Large group vacation rentals in Maryland

Lakefront vacation rentals in Maryland

Discover more beyond the pool in Maryland

Maryland rewards travelers who love a rich blend of coastal character and city culture. In Baltimore, colorful rowhouses frame the harbor, historic markets buzz, and a passionate sports scene keeps energy high from spring through fall. World class institutions, live music, and a thriving theater calendar add depth to every itinerary.

Weekend plans come easy. Watch the sun spark off the Patapsco, catch a game at Camden Yards, sample Chesapeake flavors, or wander waterfront trails for a slower pace. With major airports and rail links close at hand, gathering here is effortless. That is why Wander’s private-pool luxury rentals in Maryland are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Maryland

Why should I book a Wander in Maryland 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 Maryland 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 Maryland?

Some of our most popular private pool vacation rentals in Maryland include Plaza1606, MarigotBeach_1003, and MarigotBeach_1002. 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 Maryland?

Wander offers 3 private pool vacation rentals in Maryland, 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 Maryland?

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

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

Yes. Every Wander home in Maryland 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.