Holiday rentals near Castle Island
We found 2,475 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals near Castle Island that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Castle Island
Showing deals for:14 Nov - 21 Nov
Image gallery for Beautiful Boston Brownstone!
1010 out of 10 rating
Exceptional
(77 reviews)
Beautiful Boston Brownstone!
Boston, MA
8% off
Price is AU$6,217
AU$6,217
AU$888 per night
includes taxes & fees
Image gallery for 80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
9.49.4 out of 10 rating
Exceptional
(15 reviews)
80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
Boston, MA
15% off
Price is AU$3,847
AU$3,847
AU$550 per night
includes taxes & fees
Image gallery for Stunning South End/Back Bay Penthouse!
1010 out of 10 rating
Exceptional
(89 reviews)
Stunning South End/Back Bay Penthouse!
Boston, MA
8% off
Price is AU$6,893
AU$6,893
AU$985 per night
includes taxes & fees
Image gallery for West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
9.89.8 out of 10 rating
Exceptional
(63 reviews)
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Boston, MA
15% off
Price is AU$4,185
AU$4,185
AU$598 per night
includes taxes & fees
Image gallery for Modern 2BR/ Close to Boston with a lovely outdoor space
9.49.4 out of 10 rating
Exceptional
(22 reviews)
Modern 2BR/ Close to Boston with a lovely outdoor space
Melrose, MA
8% off
Price is AU$3,219
AU$3,219
AU$460 per night
includes taxes & fees
Image gallery for 39-SPRING GETAWAY EARLY BIRD 10%! Newly Built & Cozy Townhouse
9.69.6 out of 10 rating
Exceptional
(44 reviews)
39-SPRING GETAWAY EARLY BIRD 10%! Newly Built & Cozy Townhouse
Quincy, MA
15% off
Price is AU$3,720
AU$3,720
AU$531 per night
includes taxes & fees
Image gallery for Back-Bay Upscale Central Condo Bos Common Downtown
1010 out of 10 rating
Exceptional
(6 reviews)
Back-Bay Upscale Central Condo Bos Common Downtown
Boston, MA
7% off
Price is AU$6,789
AU$6,789
AU$970 per night
includes taxes & fees
Image gallery for Back-Bay 2BR Penthouse w Roof top and GYM
8.48.4 out of 10 rating
Very good
(6 reviews)
Back-Bay 2BR Penthouse w Roof top and GYM
Boston, MA
15% off
Price is AU$6,187
AU$6,187
AU$884 per night
includes taxes & fees
Image gallery for Travelers Choice Best of Boston Houseboat Suite 2!
9.89.8 out of 10 rating
Exceptional
(44 reviews)
Travelers Choice Best of Boston Houseboat Suite 2!
Boston, MA
8% off
Price is AU$4,669
AU$4,669
AU$667 per night
includes taxes & fees
Image gallery for Pleasant and fully furnished 4-bedroom and two bathrooms house in Braintree MA
1010 out of 10 rating
Exceptional
(6 reviews)
Pleasant and fully furnished 4-bedroom and two bathrooms house in Braintree MA
Braintree, MA
21% off
Price is AU$4,982
AU$4,982
AU$712 per night
includes taxes & fees
Image gallery for SPRING GETAWAY EARLY BIRD 10% - 82 Newly renovated, luxury apartment in Boston
9.69.6 out of 10 rating
Exceptional
(26 reviews)
SPRING GETAWAY EARLY BIRD 10% - 82 Newly renovated, luxury apartment in Boston
Boston, MA
15% off
Price is AU$3,304
AU$3,304
AU$472 per night
includes taxes & fees
Image gallery for 76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
9.69.6 out of 10 rating
Exceptional
(7 reviews)
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
Boston, MA
12% off
Price is AU$5,162
AU$5,162
AU$737 per night
includes taxes & fees
Image gallery for Spacious Triplex with Large backyard FreePrkg
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Spacious Triplex with Large backyard FreePrkg
Boston, MA
8% off
Price is AU$35,481
AU$35,481
AU$5,069 per night
includes taxes & fees
Image gallery for Boston Luxury Home, Free parking, 5 mins to the Casino, 10 minutes to airport.
9.89.8 out of 10 rating
Exceptional
(64 reviews)
Boston Luxury Home, Free parking, 5 mins to the Casino, 10 minutes to airport.
Everett, MA
8% off
Price is AU$3,158
AU$3,158
AU$451 per night
includes taxes & fees
Image gallery for Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
Medford, MA
15% off
Price is AU$2,571
AU$2,571
AU$367 per night
includes taxes & fees
Image gallery for 76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
1010 out of 10 rating
Exceptional
(8 reviews)
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Boston, MA
8% off
Price is AU$6,785
AU$6,785
AU$969 per night
includes taxes & fees
Image gallery for 284-Cozy House with free huge parking
9.89.8 out of 10 rating
Exceptional
(67 reviews)
284-Cozy House with free huge parking
Quincy, MA
15% off
Price is AU$5,470
AU$5,470
AU$781 per night
includes taxes & fees
Image gallery for 14b-Charming, beautiful 3-bedroom apartment in Boston
9.89.8 out of 10 rating
Exceptional
(8 reviews)
14b-Charming, beautiful 3-bedroom apartment in Boston
Boston, MA
8% off
Price is AU$4,329
AU$4,329
AU$618 per night
includes taxes & fees
Image gallery for Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!
Revere, MA
8% off
Price is AU$4,340
AU$4,340
AU$620 per night
includes taxes & fees
Image gallery for Cody's Place Winthrop Boston Logan Airport Beaches
1010 out of 10 rating
Exceptional
(31 reviews)
Cody's Place Winthrop Boston Logan Airport Beaches
Winthrop, MA
15% off
Price is AU$2,392
AU$2,392
AU$342 per night
includes taxes & fees
Image gallery for A Cozy 5BR Apartment near Harvard Square and MIT
9.89.8 out of 10 rating
Exceptional
(41 reviews)
A Cozy 5BR Apartment near Harvard Square and MIT
Cambridge, MA
8% off
Price is AU$7,572
AU$7,572
AU$1,082 per night
includes taxes & fees
Image gallery for Great Apartment on River/ Harvard Square two blocks
9.09.0 out of 10 rating
Wonderful
(17 reviews)
Great Apartment on River/ Harvard Square two blocks
Cambridge, MA
8% off
Price is AU$2,526
AU$2,526
AU$361 per night
includes taxes & fees
Image gallery for Adams Village 6-Bed Apt: City Perks, Suburban Vibe
8.68.6 out of 10 rating
Excellent
(8 reviews)
Adams Village 6-Bed Apt: City Perks, Suburban Vibe
Boston, MA
8% off
Price is AU$6,536
AU$6,536
AU$934 per night
includes taxes & fees
Image gallery for Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Boston, MA
8% off
Price is AU$8,350
AU$8,350
AU$1,193 per night
includes taxes & fees
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Find the best place to stay - Castle Island
Spectacular Ocean Sunsets I Pet Friendly
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Spectacular Oceanfront 1 Bedroom Unit in Winthrop
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
The Pistachio Room at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
Pet-Friendly Revere Getaway, Steps from the T!
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Sleeps 4 · 1 bedroom · 1 bathroom
8.88.8 out of 10
Excellentexcellent
36 reviews(36 reviews)
Beautiful Beach House, Hull Sleeps 5
Sleeps 6 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Top rated rentals - Castle Island
Quiet and comfortable
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value