Luxury Vacation Rentals with a Private Pool in Boston

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

Top-rated private pool vacation rentals in Boston

Apartment in Boston

2 bedrooms•2 baths

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New

Apartment in Cambridge

1 bedroom•1 bath

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New

Apartment in Boston

2 bedrooms•2 baths

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New

Apartment in Boston

2 bedrooms•2 baths

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New

Welcome to private poolside luxury in Boston

Make Boston your next escape with Wander's luxury private pool vacation rentals in Boston. Our handpicked homes combine the polish of a five star stay with the privacy of a residence, operated to exacting standards.

Enjoy a private swim whenever you like, ultra fast WiFi, refined bedrooms, and thoughtfully equipped kitchens that make work and downtime effortless. With pristine cleaning, dependable smart tech, and a 24/7 concierge, every detail is handled so you can relax without compromise.

Every Wander looks like the photos and feels like a hotel, so you can book Boston with confidence.

Available soon in Boston

Apartment in Boston

2 bedrooms•2 baths

•

New

Apartment in Cambridge

1 bedroom•1 bath

•

New

Apartment in Boston

2 bedrooms•2 baths

•

New

Apartment in Boston

2 bedrooms•2 baths

•

New

All homes in Boston

Apartment in Boston

2 bedrooms•2 baths

•

New

Apartment in Cambridge

1 bedroom•1 bath

•

New

Apartment in Boston

2 bedrooms•2 baths

•

New

Apartment in Boston

2 bedrooms•2 baths

•

New

View all homes

Highlights in Boston

Discover America's storied past, world-class museums, and iconic sports culture in the historic and vibrant city of Boston.

The Freedom Trail

Faneuil Hall Marketplace

Fenway Park

Museum of Fine Arts, Boston

New England Aquarium

Boston Common and Public Garden

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 Boston

More popular private pool destinations near Boston

Private pool vacation rentals in Barnstable

Private pool vacation rentals in Hyannis Port

Other popular amenities & vacation types in Boston

Family vacation rentals in Boston

Pet-friendly vacation rentals in Boston

Discover more beyond the pool in Boston

Boston blends sleek harbor views with brick lined charm, creating a city that feels current and timeless. Start on the Charles River Esplanade, browse Newbury Street, then take in a curtain call in the Theater District. Culture, sport, and style intersect at every turn.

Each season reshapes the mood, from sail filled summers and vivid fall canopies to crisp winters with twinkling lights and fresh spring blooms on the Common. Powered by renowned universities and a bold dining and arts scene, the city hums year round. This is why Wander's luxury private pool vacation rentals in Boston are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Boston

Why should I book a Wander in Boston 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 Boston 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 Boston?

Some of our most popular private pool vacation rentals in Boston include Central 2BR in Boston w/Pool, Gym, Washer/Dryer, Upscale Penthouse near MIT & Harvard in Central Square!, and 2BR Penthouse Boston Common DT. 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 Boston?

Wander offers 4 private pool vacation rentals in Boston, 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 Boston?

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

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

Yes. Every Wander home in Boston 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.