456+ Private Villas and Holiday Rentals in Roslindale |
Roslindale Holiday Rentals
New
Villa
3 Bedrooms
2 Baths
8 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $825/Night
7 Nights - US $5,772
Apartment
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1786.81 ft²
- Fireplace/Heating
- Parking
Air Conditioner
Internet
US $256/Night
7 Nights - US $1,792
House
- Boston
- ·
- Hyde Square
- 0.23 mi to center
3.6Average
(51 Reviews)
1 Bedroom
1 Bath
- Kitchen
- Parking
- Internet
Child Friendly
US $153/Night
7 Nights - US $1,070
New
Condo
- Boston
- ·
- West Codman Hill - West Lower Mills
- 0.26 mi to center
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $742/Night
7 Nights - US $5,197
Apartment
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
4 Guests
1905.21 ft²
- Parking
- Air Conditioner
- Internet
Security/Safety
US $222/Night
7 Nights - US $1,553
New
Condo
2 Bedrooms
1 Bath
4 Guests
- Internet
- Child Friendly
Laundry
Bedding/Linens
US $151/Night
7 Nights - US $1,054
New
Apartment
- Boston
- ·
- West Roxbury
- 0.85 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $48/Night
7 Nights - US $338
Apartment
- Boston
- ·
- Jamaica Plain
- 0.34 mi to center
10.0Exceptional
(127 Reviews)
2 Bedrooms
2 Baths
6 Guests
2000 ft²
Hot Tub- Fireplace/Heating
- Kitchen
- Parking
US $345/Night
7 Nights - US $2,414
Apartment
- Boston
- ·
- Roslindale
- 0.43 mi to center
10.0Exceptional
(106 Reviews)
2 Bedrooms
1 Bath
5 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $333/Night
7 Nights - US $2,334
Luxury Holiday Rentals in Roslindale
Over 447+ Luxury Holiday Rentals in or Near Roslindale
House
- Boston
- ·
- Fields Corner West
- 0.26 mi to center
10.0Exceptional
(1 Review)
10 Bedrooms
4 Baths
30 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $2,948/Night
7 Nights - US $20,638
Condo
- Boston
- ·
- Forest Hills - Woodbourne
- 0.32 mi to center
10.0Exceptional
(1 Review)
10 Bedrooms
5 Baths
24 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,758/Night
7 Nights - US $12,308
House
10.0Exceptional
(3 Reviews)
6 Bedrooms
5 Baths
12 Guests
4898 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,752/Night
7 Nights - US $12,267
Condo
- Boston
- ·
- Forest Hills - Woodbourne
- 0.32 mi to center
15 Bedrooms
7 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,641/Night
7 Nights - US $11,484
Apartment
- Boston
- ·
- West Roxbury
- 0.66 mi to center
3 Bedrooms
1 Bath
5 Guests
1194.79 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,344/Night
7 Nights - US $9,409
House
- Boston
- ·
- Fields Corner West
- 0.24 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
2 Baths
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,338/Night
7 Nights - US $9,363
House
- Boston
- ·
- Codman Square
- 0.39 mi to center
10.0Exceptional
(5 Reviews)
5 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,322/Night
7 Nights - US $9,252
New
Apartment
- Boston
- ·
- Dudley - Brunswick King
- 0.54 mi to center
3 Bedrooms
2 Baths
8 Guests
1399.31 ft²
- Balcony/Terrace
Breakfast- Parking
- Air Conditioner
US $1,315/Night
7 Nights - US $9,204
Condo
- Boston
- ·
- West Codman Hill - West Lower Mills
- 0.44 mi to center
8.0Excellent
(10 Reviews)
5 Bedrooms
2 Baths
8 Guests
2800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,313/Night
7 Nights - US $9,189
Top-Rated Holiday Rentals with a Pool in Roslindale
Over 4+ The Best Private Villas and Holiday Rentals in Roslindale with a Pool
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
3500 ft²
Private Pool- Hot Tub
- Fireplace/Heating
Pool
US $996/Night
7 Nights - US $6,971
House
- Boston
- ·
- Jamaica Plain
- 1.04 mi to center
9.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Pool
Pet Friendly- Kitchen
- Internet
US $500/Night
7 Nights - US $3,501
Apartment
- Boston
- ·
- West Roxbury
- 0.51 mi to center
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $242/Night
7 Nights - US $1,692
Apartment
- Boston
- ·
- West Roxbury
- 0.06 mi to center
1 Bedroom
1 Bath
1 Guest
800 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $110/Night
7 Nights - US $770
Pet-Friendly Holiday Rentals in Roslindale
Over 153+ Pet-Friendly Holiday Rentals in or Near Roslindale
Condo
- Boston
- ·
- Metropolitan Hill - Beech Street
- 0.41 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $240/Night
7 Nights - US $1,681
Apartment
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
9 Guests
1302.43 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $832/Night
7 Nights - US $5,826
Apartment
- Boston
- ·
- Hyde Square
- 0.23 mi to center
3.6Average
(4 Reviews)
1 Bedroom
1 Bath
1 Guest
- Pet Friendly
- Kitchen
- Internet
- Child Friendly
US $163/Night
7 Nights - US $1,141
House
- Boston
- ·
- Roslindale
- 0.69 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
780 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $316/Night
7 Nights - US $2,210
Apartment
- Boston
- ·
- West Roxbury
- 0.68 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
6 Guests
1097.92 ft²
- Fireplace/Heating
View- Pet Friendly
- Parking
US $240/Night
7 Nights - US $1,681
Condo
- Boston
- ·
- Egleston Square
- 0.19 mi to center
9.8Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $463/Night
7 Nights - US $3,243
Apartment
- Boston
- ·
- Codman Square
- 0.67 mi to center
9.6Exceptional
(153 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $276/Night
7 Nights - US $1,931
Apartment
- Boston
- ·
- Egleston Square
- 0.08 mi to center
9.6Exceptional
(64 Reviews)
2 Bedrooms
1 Bath
5 Guests
1350 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $472/Night
7 Nights - US $3,301
Apartment
- Boston
- ·
- Brook Farm
- 0.55 mi to center
9.4Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $337/Night
7 Nights - US $2,356
Large Holiday Rentals and Private Villas in Roslindale
Over 101+ Large Holiday Rentals and Private Villas in or Near Roslindale
Apartment
9.4Exceptional
(9 Reviews)
5 Bedrooms
3 Baths
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $669/Night
7 Nights - US $4,686
Apartment
- Boston
- ·
- Codman Square
- 0.30 mi to center
9.9Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
13 Guests
807.29 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $652/Night
7 Nights - US $4,566
Apartment
6.0Good
(1 Review)
6 Bedrooms
2 Baths
23 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $765/Night
7 Nights - US $5,357
House
9.8Exceptional
(31 Reviews)
4 Bedrooms
3 Baths
10 Guests
2002.09 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $292/Night
7 Nights - US $2,045
House
- Boston
- ·
- High Street Hill
- 0.14 mi to center
6 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $817/Night
7 Nights - US $5,716
New
House
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $473/Night
7 Nights - US $3,313
House
- Boston
- ·
- Jamaica Plain
- 0.39 mi to center
10.0Exceptional
(103 Reviews)
4 Bedrooms
2 Baths
10 Guests
2200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $850/Night
7 Nights - US $5,951
Apartment
- Boston
- ·
- Codman Square
- 0.30 mi to center
10.0Exceptional
(17 Reviews)
3 Bedrooms
2 Baths
13 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $513/Night
7 Nights - US $3,588
Apartment
- Boston
- ·
- Jamaica Plain
- 0.67 mi to center
10.0Exceptional
(16 Reviews)
4 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $714/Night
7 Nights - US $4,995
Wheelchair Accessible Holiday Homes in Roslindale
Over 26+ Wheelchair Accessible Holiday Homes in or Near Roslindale
Apartment
- Boston
- ·
- Lower Mills
- 0.42 mi to center
2 Bedrooms
1 Bath
4 Guests
804 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $241/Night
7 Nights - US $1,690
Apartment
- Boston
- ·
- Lower Washington - Mount Hope
- 0.46 mi to center
2 Bedrooms
2 Baths
4 Guests
1054 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $239/Night
7 Nights - US $1,675
Apartment
- Boston
- ·
- Lower Mills
- 0.42 mi to center
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $228/Night
7 Nights - US $1,597
Apartment
- Boston
- ·
- Lower Washington - Mount Hope
- 0.46 mi to center
2 Bedrooms
2 Baths
4 Guests
1054 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $181/Night
7 Nights - US $1,264
Apartment
- Boston
- ·
- Lower Washington - Mount Hope
- 0.46 mi to center
1 Bedroom
1 Bath
2 Guests
767 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $157/Night
7 Nights - US $1,097
Apartment
- Boston
- ·
- Forest Hills - Woodbourne
- 0.44 mi to center
1 Bedroom
1 Bath
2 Guests
643 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $152/Night
7 Nights - US $1,066
Apartment
- Boston
- ·
- Lower Mills
- 0.42 mi to center
1 Bedroom
1 Bath
2 Guests
656 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $152/Night
7 Nights - US $1,064
Apartment
- Boston
- ·
- Lower Mills
- 0.42 mi to center
1 Bedroom
1 Bath
2 Guests
624 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $152/Night
7 Nights - US $1,062
Apartment
- Boston
- ·
- Forest Hills - Woodbourne
- 0.44 mi to center
1 Bedroom
1 Bath
2 Guests
660 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $148/Night
7 Nights - US $1,036
Roslindale Private Villas and Holiday Homes Under $200
Over 83+ Roslindale Private Villas and Holiday Homes Under $200
House
- Boston
- ·
- Highland Park
- 0.30 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $138/Night
7 Nights - US $966
Apartment
9.8Exceptional
(9 Reviews)
1 Bedroom
1 Bath
5 Guests
602.78 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $166/Night
7 Nights - US $1,161
House
- Boston
- ·
- Hyde Square
- 0.23 mi to center
2.6Average
(116 Reviews)
1 Bedroom
1 Bath
Spa- Breakfast
- Kitchen
- Parking
US $80/Night
7 Nights - US $560
Apartment
- Boston
- ·
- West Roxbury
- 0.06 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
1 Guest
700 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $173/Night
7 Nights - US $1,212
Apartment
- Boston
- ·
- Roslindale
- 0.25 mi to center
9.1Exceptional
(9 Reviews)
1 Bedroom
1 Bath
6 Guests
182.99 ft²
- View
- Parking
- Air Conditioner
- Internet
US $73/Night
7 Nights - US $514
House
2 Bedrooms
1 Bath
2 Guests
900 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $185/Night
7 Nights - US $1,298
Condo
- Boston
- ·
- Highland Park
- 0.26 mi to center
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $172/Night
7 Nights - US $1,207
Apartment
- Boston
- ·
- Highland Park
- 0.25 mi to center
2 Bedrooms
2 Baths
3 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $145/Night
7 Nights - US $1,014
Apartment
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $123/Night
7 Nights - US $860
Instantly Bookable Holiday Homes in Roslindale
Over 243+ Instantly Bookable Holiday Homes in or Near Roslindale
Condo
- Boston
- ·
- Lower Washington - Mount Hope
- 0.41 mi to center
10.0Exceptional
(70 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $264/Night
7 Nights - US $1,851
Apartment
10.0Exceptional
(19 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $275/Night
7 Nights - US $1,923
Apartment
- Boston
- ·
- Jamaica Plain
- 0.48 mi to center
10.0Exceptional
(18 Reviews)
2 Bedrooms
1 Bath
4 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $481/Night
7 Nights - US $3,369
House
- Boston
- ·
- Jamaica Hills - Pond
- 0.42 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,164/Night
7 Nights - US $8,147
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $380/Night
7 Nights - US $2,663
House
- Boston
- ·
- West Codman Hill - West Lower Mills
- 0.46 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
1020 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $294/Night
7 Nights - US $2,055
House
- Boston
- ·
- Brook Farm
- 0.10 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $527/Night
7 Nights - US $3,689
Apartment
9.8Exceptional
(111 Reviews)
2 Bedrooms
2 Baths
4 Guests
1148 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $394/Night
7 Nights - US $2,760
Condo
9.8Exceptional
(77 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $204/Night
7 Nights - US $1,425
Book a Last Minute Place to Stay in Roslindale
About Casai's Private Villas and Holiday Rentals in Roslindale
Discover more than 456 vacation rentals available in Roslindale. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Roslindale.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Roslindale, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Roslindale. On average, places to stay near Roslindale offer 701.48 ft², with nightly prices averaging US $433.
With Casai, finding and comparing holiday rentals in Roslindale is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Roslindale
| Type | Count |
|---|---|
| Holiday Apartments | 277 |
| Vacation Homes | 122 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Roslindale
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Roslindale.
Weather in Roslindale, MA
View the weather forecast for Roslindale before booking your Roslindale Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Other Places to Stay in Roslindale, MA
Frequently Asked Questions About Roslindale?
What are the top holiday rentals in Roslindale?
With numerous options available in Roslindale, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Roslindale:
- Airy new apt for 2-6. Off-street parking. Walk to shops/restaurants/subway/bus
- Boston-Modern Spacious Family Friendly Apartment w/Parking
- City's Hippest Neighborhood. n
- Modern 2br with W/D in unit, Parking, central air
- 🎖The Ashmont Suite - Close to Subway + Downtown🎖
- Milton Retreat, 5 min to Boston ,major highways . Safe family neighborhood . 😀
- Spacious, Comfy Colonial, minutes to Boston and highways
- Victorian house, clean comfortable and well located
- Budget-Friendly Basement 2BR Retreat
- Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train
Which holiday homes in Roslindale are best for families?
If you're searching for a family-friendly holiday home in Roslindale, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Roslindale:
How many Casai.com holiday rentals are available in Roslindale?
As of 2026, Casai boasts over 456 properties listed in the Roslindale area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Roslindale.
Nearby Neighborhood (8)
| Neighborhood | Property Count |
|---|---|
| Jamaica Hills - Pond Vacation Rentals in Boston, Massachusetts | 1511 |
| West Street - River Street Vacation Rentals in Boston, Massachusetts | 351 |
| Forest Hills - Woodbourne Vacation Rentals in Boston, Massachusetts | 780 |
| Lower Washington - Mount Hope Vacation Rentals in Boston, Massachusetts | 501 |
| Stony Brook - Cleary Square Vacation Rentals in Boston, Massachusetts | 206 |
| Brook Farm Vacation Rentals in Boston, Massachusetts | 174 |
| Metropolitan Hill - Beech Street Vacation Rentals in Boston, Massachusetts | 262 |
| Southern Mattapan Vacation Rentals in Boston, Massachusetts | 437 |
People Also Ask
Finding the best prices in Roslindale
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