We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Boston Holiday Vacation with Pools

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 km
Price per night
C$0
C$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
Show more
194 rentals in Boston.
Sort by:
Tripadvisor Sort
Beautiful Back Bay Duplex
Back Bay
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
5 other travellers have booked this property
Luxury Suite, Moroccan Furnishings, Boston
Charlestown
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
15 other travellers have booked this property
Elegant new renovation of a historic brownstone on a prime South End street
South End
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
22 other travellers have booked this property
Elegance at Salem Court, Boston
Charlestown
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
25 other travellers have booked this property
Cozy, comfy Boston single family house, fully equipped and close to everything!
Jamaica Plain
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
4 other travellers have booked this property
Boston, New Beautiful chic 3BR 3BA apt. sleeps 7 (M1G)
North End
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
7 other travellers have booked this property
Quiet cozy apartment close to train & restaurants
Jamaica Plain
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Boston's 2 bedroom vacation rental condo near Stony Brook's Orange line subway
Jamaica Plain, Egleston Square
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 other travellers have booked this property
Houseboat in Boston Harbor
Charlestown, Bunker Hill
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
10 other travellers have booked this property
Newly Renovated Condo near Boston (No Party)
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
8 other travellers have booked this property
Save time - get the best Boston rentals sent straight to your email!
4 bedroom Victorian Condo
Jamaica Plain
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
8 other travellers have booked this property
Back Bay Condos 1BD/1BA 3
Symphony
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Location! Location! Modern 2BD 2 BA w/Parking
South Boston
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
5 other travellers have booked this property
Adorable 2 Bedroom Apartment in Boston
Roslindale
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 other travellers have booked this property
Chic South End, Back Bay, Downtown Boston Apartment
South End
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Architectural, Accessible, Charming House
Jamaica Plain
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
4 other travellers have booked this property
Seaport Luxe Condo Studio 4
Seaport District / South Boston Waterfront
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beacon Hill Brownstone - 2 br condo on Beacon Hill
Beacon Hill
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spectacular Luxury Super Yacht In Boston Harbor Sleeps Eight In Four Staterooms
Charlestown, Bunker Hill
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston
Eagle Hill
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
8 other travellers have booked this property
Beautiful Design, Perfect Location and enough space for a large group
Jamaica Plain
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Brand New comfort Home Close to T and Boston
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
13 other travellers have booked this property
Incredible 1br Luxury Condo - Charlesview Suites
Fenway / Kenmore, Symphony, Kenmore
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Amazing Historical 1BR Modern Loft in the Heart of Downtown, Waterfront
Downtown, Financial District
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful Large 3 bed apt, close to river and Universities, Downtown 4m v quiet
Brighton
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
3 bedroom private condo recently renovated, near Logan airport T station
Jeffries Point, Central Maverick Square - Paris Street
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 other travellers have booked this property
Private 4 bedroom apartment close to airport T on treelined street great loc!
Jeffries Point, Central Maverick Square - Paris Street
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
5 other travellers have booked this property
Global Luxury Suites Fenway
Fenway / Kenmore, West Fens, Kenmore
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Clean and Spacious 2 bedroom condo in Dorchester
Dorchester / Roxbury / Mattapan, Neponset - Port Norfolk
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Boston penthouse
Downtown
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious Modern Sunny Upscale 3br Apt w/ WiFi close to Ⓣ DT ✈ Encore casino ♠♣♢
Jeffries Point
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Private Room in Spacious Boston Home
Eagle Hill
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful Beacon Hill Penthouse
Downtown, Beacon Hill
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sunny 2 Bedrooms Victorian Fully Furnished Condo
Lower Washington - Mount Hope, Roslindale
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
North End Enchanted Cottage
North End
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Historic Brownstone
Allston Village, Brighton
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Entire 2br Spacious Modern Private Art Gallery Close to Subway Airport Downtown
Jeffries Point
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Global Luxury Suites at China Town
Chinatown, Theater District
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Global Luxury Suites Downtown Boston
Chinatown
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tourist Heaven
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious Coolidge Corner Apt
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sunny & Cozy 2 bdrm Duplex, Jamaica Plain, Boston
Jamaica Plain
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
2 Bedroom Apartment Available
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Charming House in Downtown Boston
Chinatown
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Historic Boston Townhouse with Courtyard
Downtown, Government Center
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
4 Bedroom Fully Furnished Tudor House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Large 3 bedrooms 3.5 bath right in the city of Boston
Downtown
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
5br - 2200ft2 - Duxbury Beach
Mattapan, Southern Mattapan
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious Studio in Boston's North End/Little Italy
North End
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Wonderful, Sunny and Big Bedroom beautiful house
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
1234
Boston Vacation Rentals
Planning a trip to Boston? Consider a Boston vacation rental instead of a hotel. There’s a great variety of vacation rental properties available in Boston, and one’s sure to be right for you. How about a quaint apartment in Harvard Square? Or an elegant Boston vacation rental apartment on Beacon Hill? If you’re traveling with a big family, you might want to consider renting a vacation house in a Boston suburb like Lexington or Arlington. Whatever you choose, we’ll help you find a great deal on your Boston vacation rental, and we’ll give you plenty of unbiased user reviews of Boston vacation rentals, so you can book with confidence.
More
Boston Vacation Rentals
Planning a trip to Boston? Consider a Boston vacation rental instead of a hotel. There’s a great variety of vacation rental properties available in Boston, and one’s sure to be right for you. How about a quaint apartment in Harvard Square? Or an elegant Boston vacation rental apartment on Beacon Hill? If you’re traveling with a big family, you might want to consider renting a vacation house in a Boston suburb like Lexington or Arlington. Whatever you choose, we’ll help you find a great deal on your Boston vacation rental, and we’ll give you plenty of unbiased user reviews of Boston vacation rentals, so you can book with confidence.
Boston attractions
Many of Boston’s top attractions are located within a relatively small area, and a Boston vacation rental in Back Bay or Beacon Hill will put you within walking distance. If it’s your first time in Boston, definitely walk the Freedom Trail. It’s an excellent introduction to Boston’s role in the Revolutionary War. Explore Boston’s North End for a little taste of Italy (dine at almost any restaurant, but save room for a cannoli from Mike’s Pastry or Modern Pastry). If you like the arts, visit the Museum of Fine Arts and the Isabella Stewart Gardner Museum. Finally, if the Red Sox, Celtics or Bruins are in town, try to catch a game. You haven’t really experienced Boston unless you’ve sat in the cheap seats at Fenway Park! A vacation rental in Boston makes it easy to explore all of these attractions and more.
Family vacation rentals in Boston
Boston’s a great destination if you’re traveling with kids. You might find your kids have a newfound interest in American history after seeing landmarks like the Old North Church and the U.S.S. Constitution in person! Boston boasts an excellent Children’s Museum and Science Museum, too. Teens will love shopping at Quincy Market, a collection of shops and restaurants near Faneuil Hall. And Boston has plenty of family-friendly restaurants, especially the old-school, no-frills seafood places near Boston Harbor.
Day trips in the Boston area
If you have a car at your disposal, you might venture a bit farther afield from your vacation rental in Boston. Continue the Revolutionary War theme with a visit to Minuteman National Park in Lexington… then stop in at Thoreau’s Walden Pond. The De Cordova Museum and Sculpture Park is a fun option, especially for families. Finally, there’s plenty of great shopping around Boston—the Wrentham Outlets are a popular day-trip destination for travelers renting a vacation home or condo in Boston.