Best Vacation Homes in South Side
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
1800 ft²
Fireplace/Heating
Kitchen
Parking
Air Conditioner
US $482/Night
7 Nights - US $3,376
Apartment
9.0(1 Review)
3 Bedrooms
1 Bath
6 Guests
1248.61 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
Internet
US $340/Night
7 Nights - US $2,380
Apartment
9.6(1198 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace
Pet Friendly- Kitchen
US $189/Night
7 Nights - US $1,321
New
House
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $530/Night
7 Nights - US $3,708
Apartment
8.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
1248.61 ft²
- Fireplace/Heating
View- Parking
- Air Conditioner
US $270/Night
7 Nights - US $1,890
Condo
10.0(32 Reviews)
3 Bedrooms
1 Bath
5 Guests
1100 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $306/Night
7 Nights - US $2,142
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1065 ft²
- Fireplace/Heating
Pool- Pet Friendly
- Kitchen
US $303/Night
7 Nights - US $2,120
Apartment
9.6(38 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $199/Night
7 Nights - US $1,394
South Side Luxury Rentals
House
4 Bedrooms
3 Baths
10 Guests
2195.84 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $1,248/Night
7 Nights - US $8,736
Condo
9.8(27 Reviews)
4 Bedrooms
4 Baths
10 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,153/Night
7 Nights - US $8,072
House
9.8(71 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $972/Night
7 Nights - US $6,803
House
6 Bedrooms
2 Baths
10 Guests
5005.22 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $950/Night
7 Nights - US $6,650
Apartment
6 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $937/Night
7 Nights - US $6,557
Apartment
6 Bedrooms
4 Baths
12 Guests
2443.41 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $896/Night
7 Nights - US $6,271
House
5 Bedrooms
3 Baths
382 ft²
- Fireplace/Heating
- Balcony/Terrace
- Air Conditioner
- Internet
US $800/Night
7 Nights - US $5,600
Villa
9.2(15 Reviews)
4 Bedrooms
3 Baths
10 Guests
2196 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $759/Night
7 Nights - US $5,311
South Side Pet Friendly Vacation Rentals
Apartment
9.6(19 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $536/Night
7 Nights - US $3,753
Apartment
7.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
1194.79 ft²
- View
- Pet Friendly
- Parking
- Air Conditioner
US $502/Night
7 Nights - US $3,513
Apartment
9.4(30 Reviews)
2 Bedrooms
2 Baths
5 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $391/Night
7 Nights - US $2,734
Apartment
1 Bedroom
1 Bath
3 Guests
850.35 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Air Conditioner
US $231/Night
7 Nights - US $1,617
Apartment
9.2(56 Reviews)
2 Bedrooms
2 Baths
5 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $354/Night
7 Nights - US $2,476
Apartment
2 Bedrooms
2 Baths
4 Guests
1108 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $378/Night
7 Nights - US $2,646
Apartment
2 Bedrooms
2 Baths
4 Guests
1108 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $262/Night
7 Nights - US $1,834
Apartment
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $252/Night
7 Nights - US $1,764
South Side Large Vacation Homes
Apartment
1 Bedroom
1 Bath
30 Guests
- Parking
- Air Conditioner
- Internet
Child Friendly
US $124/Night
7 Nights - US $868
House
10.0(11 Reviews)
4 Bedrooms
2 Baths
10 Guests
2592 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $215/Night
7 Nights - US $1,505
House
9.2(7 Reviews)
4 Bedrooms
1 Bath
11 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $640/Night
7 Nights - US $4,477
House
10.0(6 Reviews)
6 Bedrooms
5 Baths
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,656/Night
7 Nights - US $11,590
Villa
10.0(6 Reviews)
6 Bedrooms
5 Baths
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,321/Night
7 Nights - US $9,245
House
10.0(2 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $992/Night
7 Nights - US $6,943
House
10.0(1 Review)
5 Bedrooms
5 Baths
11 Guests
9000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $3,445/Night
7 Nights - US $24,114
House
8.4(7 Reviews)
4 Bedrooms
2 Baths
10 Guests
1800 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $620/Night
7 Nights - US $4,340
Why Choose Rent By Owner for your South Side Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit South Side
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience in this region, so consider planning your trip during the seasons when the area offers optimal weather and local events for a more memorable stay.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this destination experiences high tourism activity, making it an ideal time for enjoying the area's outdoor amenities and vibrant community events.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
Fall (September to November)
Autumn brings cooler weather and colorful foliage, attracting visitors seeking a picturesque setting and outdoor activities in the region.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter months are quieter, offering a peaceful experience with colder temperatures that make it perfect for cozy stays and indoor activities.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 25°F
Spring (March to May)
In early spring, the area sees fewer tourists, providing an excellent opportunity for budget-friendly bookings and enjoying the budding landscape in a tranquil setting.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 45°F
Weekly Weather Forecast for South Side
How to Book Your South Side Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in South Side
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a spacious patio or picnic area perfect for gatherings.
- Take advantage of private gardens or landscaped yards to relax and unwind.
- Make the most of outdoor grills available for cooking your favorite meals.
- Benefit from comfortable outdoor seating areas designed for enjoying the fresh air.
- Spend time in nearby parks or walking trails that are accessible from the property.
- Use outdoor recreational facilities such as sports courts or play areas for added entertainment.
- Relax in outdoor hot tubs or pools often available for a soothing experience after exploring the region.
Top Attractions Around South Side
What attractions are nearby?
During your stay, you'll find plenty of nearby activities to enjoy in this area, from exploring local parks to discovering charming cafes and dining options just moments from your South Side vacation rentals.
Family Activities
- Waltham Common Park: Enjoy a relaxing day outdoors at this family-friendly park with scenic walking trails, playgrounds, and picnic areas perfect for a day out with children.
- The Charles River Reservation: Explore the picturesque riverfront, where you can partake in gentle walks or bike rides along the scenic paths ideal for all ages.
- Charles River Museum of Industry and Innovation: Discover local history and interactive exhibits that captivate young minds while learning about the region's industrial heritage.
- Prospect Hill Park: Visit this expansive green space offering open fields, sports facilities, and playgrounds, making it an excellent spot for family gatherings and outdoor fun.
Adult Activities
- Waltham Historical Society Museum: Dive into the area's rich history by exploring this museum, which offers insight into the local heritage and cultural development.
- Charles River Esplanade: Enjoy a leisurely stroll or scenic views along the riverfront, perfect for relaxing while taking in the natural beauty of this regional outdoor space.
- Prospect Hill Park: Experience outdoor recreation and panoramic city views at this popular park, ideal for picnics and unwinding after your travels.
- Alumni Stadium: Attend a lively sporting event at the region's renowned stadium, offering an exciting way to engage with local sports culture and cheer on the home team.
Other Places to Stay in South Side, MA
Moody Street Historic District
South Side Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area's diverse culinary scene by visiting local restaurants and cafes to enjoy authentic flavors unique to this destination.
- Plan Your Transportation: Arrange for reliable transportation options ahead of time to easily access popular attractions and navigate the region comfortably.
- Discover Outdoor Spaces: Make the most of nearby parks and outdoor areas to relax, unwind, or engage in recreational activities during your stay.
- Coordinate Nearby Attractions: Research must-see spots within the region so you can efficiently plan your itinerary and maximize your time here.
Transportation Options
- Waltham Commuter Rail Station: This station offers convenient train access to Boston and other regional destinations, making it easy to explore beyond the area.
- Bus Services: Local bus routes connect this part of Waltham to nearby neighborhoods and transit hubs, providing flexible transportation options.
- Rideshare Services: Popular ride-hailing apps operate here, offering a reliable and on-demand way to navigate within the region and reach key points of interest.
- Car Rentals: Several car rental agencies are available in the area, giving you the freedom to explore Waltham and its surroundings at your own pace.
Local Customs Options
- Respect for Local Heritage: Visitors often observe the community's deep appreciation for preserving its historical roots through local customs and traditions.
- Community Gatherings: Participating in neighborhood events and festivals reflects the area's strong sense of togetherness and local pride.
- Dining Etiquette: When dining out, it’s customary to embrace the region’s culinary traditions and appreciate locally sourced ingredients.
- Environmental Consciousness: The community values sustainable practices, encouraging visitors to engage in eco-friendly habits during their stay here.
South Side Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in South Side?
There are a lot of options in South Side. If you plan on staying in the South Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in South Side:
- Premium Furnished 2B 1.5B Home Monthly Stay in Newton
- Spacious Private Retreat Near Downtown Boston!
- Family-Friendly 4BR, 2B Near Boston, Walk to Moody St, Free Parking, Fast WIFI
- Contemporary Room | Free Breakfast, Parking & Gym Access
- Double Room at Fairfield Waltham | EV Charger, Pool & Fitness Center| 2 Units
- Luxury Apt with Rooftop Terrace and Pool
- Tranquil Getaway Perfect for Outdoor Enthusiasts Near Boston Attractions
- Harvard House: Make Your 2025 Family Gathering Unforgettable"
- Remodeled Townhouse close to Boston
- Luxury large house minutes to Cambridge and Boston
2. How many vacation rentals have private pools in South Side?
There are 12 vacation rentals with private pools near South Side. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in South Side are best for families?
If you are looking for a family-friendly vacation home in South Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in South Side:
4. How many Rentbyowner vacation rentals are available in South Side?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 199 in the South Side 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 South Side.
5. What is the cancellation policy for vacation rentals in South Side, Waltham?
Cancellation policies vary depending on the individual listing. You should review the specific rental agreement or contact the property owner directly to understand the terms and any potential fees associated with cancellations.
6. How do I find the best vacation rentals in Waltham for my stay?
To find the best options, use search filters related to your preferred dates, amenities, and budget on the booking website. Reading guest reviews and viewing high-quality photos can also help you select a comfortable and suitable accommodation here.
7. Are pets allowed in vacation rentals around Waltham?
Pet policies differ by property. When browsing listings, check the specific rental details or contact the owner to confirm whether pets are permitted during your stay.
8. What amenities should I expect in vacation rentals in this area?
Most vacation rentals in Waltham offer key amenities such as free Wi-Fi, fully equipped kitchens, and parking. Be sure to read each listing carefully to determine what is included to ensure it meets your needs.
9. How do I inquire about last-minute bookings or availability in Waltham?
For last-minute stays, use the website’s messaging feature to contact property owners directly or check the real-time availability calendar on the listing to see if your desired dates are open.
South Side Top Rated Vacation Rentals
Hotel
10.0(2 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $221/Night
7 Nights - US $1,548
Hotel
10.0(1 Review)
2 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $441/Night
7 Nights - US $3,088
Hotel
10.0(1 Review)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $271/Night
7 Nights - US $1,900
House
9.8(18 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $390/Night
7 Nights - US $2,731
Hotel
9.4(1848 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $122/Night
7 Nights - US $857
Hotel
9.2(1000 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $136/Night
7 Nights - US $954
Hotel
9.2(862 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $160/Night
7 Nights - US $1,119
US $160/Night
7 Nights - US $1,118
