Milton Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Milton, Massachusetts, USA

3 Mi to Blue Hills Skiing & Hiking! Couple’s Apt
10.0 (1 Review)
1 Bedroom 2 Guests
Charming Milton Escape- Blue Hills Reservation
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10.0 (2 Reviews)
3 Bedrooms 6 Guests
Large 3BR & 2BA Milton Apt w Free Parking, Balcony, TV, AC 141
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10.0 (1 Review)
3 Bedrooms 9 Guests
Spacious, Comfy Colonial, minutes to Boston and highways
10.0 (33 Reviews)
4 Bedrooms 6 Guests
Pristine 5BR Milton Apt - Free Parking, Balcony, AC & TV 142
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10.0 (1 Review)
5 Bedrooms 15 Guests
10-Spacious 5BR apt with gym, games room in the attic
10.0 (19 Reviews)
5 Bedrooms 18 Guests
Modern Red Door Haven +5mins to Boston
FromAU $1,483 per night
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9.6 (7 Reviews)
3 Bedrooms 6 Guests
Peaceful Milton Getaway- Trails & City Nearby
10.0 (3 Reviews)
6 Bedrooms 12 Guests
Jacaranda
FromAU $274 per night
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8.5 (18 Reviews)
3 Bedrooms 6 Guests
Charming Milton Escape- Blue Hills Reservation
10.0 (2 Reviews)
3 Bedrooms 6 Guests
Prestigious Milton Designer Home
FromAU $865 per night
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New
3 Bedrooms 12 Guests
8-Peaceful & Bright apt/3br right to Boston line
9.6 (4 Reviews)
3 Bedrooms 10 Guests
Milton Cozy Home
FromAU $1,713 per night
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New
5 Bedrooms 15 Guests
14-2 5BR - Milton Spacious Home near Blue Hills
9.4 (9 Reviews)
5 Bedrooms 15 Guests
3 Mi to Blue Hills: Cozy Dual-Unit Retreat
FromAU $1,210 per night
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New
4 Bedrooms 8 Guests
Red Door Oasis
FromAU $1,028 per night
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New
6 Bedrooms 12 Guests
14/1 - 3BR Milton - Cozy Apt near Blue Hills Museum
9.2 (17 Reviews)
3 Bedrooms 9 Guests
Stylish and Comfortable 3Bed 2Bath
FromAU $818 per night
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New
1 Bedroom 6 Guests
JACARANDA. A comfortable, secure two-story colonial. Whole house.
8.2 (45 Reviews)
3 Bedrooms 6 Guests
All-Season Fun! Charming Apt 3 Mi to Blue Hills
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New
3 Bedrooms 6 Guests
Hot Deal up to 20%, 6BR Milton, Parking & Pets - 172
6.0 (1 Review)
6 Bedrooms 23 Guests
3 Mi to Blue Hills Skiing & Hiking! Couple’s Apt
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New
1 Bedroom 2 Guests
All-Season Fun! Charming Apt 3 Mi to Blue Hills
4.0 (1 Review)
3 Bedrooms 6 Guests
Spacious and Comfortable 1 Bed 25 km from Gillette
New
1 Bedroom 2 Guests
3 Mi to Blue Hills: Cozy Dual-Unit Retreat
FromAU $1,274 per night
New
4 Bedrooms 8 Guests
Spacious 5BR Executive Retreat - 10 Min to Boston
New
5 Bedrooms 12 Guests
Prestigious Milton Designer Home
FromAU $847 per night
New
3 Bedrooms 12 Guests
5ES Remodeled Expansive Home, Off Street Parking
New
5 Bedrooms 10 Guests
1EC REMODELED Expansive Home, Off Street Parking
New
4 Bedrooms 9 Guests
Ski & Explore! Colorful Apt 10 Mi to Dtwn Boston!
New
3 Bedrooms 7 Guests
6 bedroom house in a quiet and convenient neighborhood
6.8 (3 Reviews)
6 Bedrooms 8 Guests

About Milton Vacation Rentals

With more than 44 Milton vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Milton.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Milton, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Milton. Places to stay near Milton are 1642.18 ft² on average, with prices averaging AU $779 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Milton with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Milton?

What are the top vacation rentals in Milton?

How many Rentbyowner vacation rentals are available in Milton?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 44 in the Milton area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Milton. 

Nearby Neighborhood (1)

NeighborhoodProperty Count
Lower Mills Vacation Rentals in Boston, Massachusetts 425