Discover Your Perfect Fenway–Kenmore Rentals by Owner

Fenway–Kenmore Rentals by Owner

9.4 (1386 Reviews)
House
Oasis Guest House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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8.7 (956 Reviews)
House
Oasis Guest House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
View Availability
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8.6 (8 Reviews)
Apartment
Brownstone Townhouse in Fenway
  • Air Conditioner
  • Parking
  • Security/Safety
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More Top-Rated Rentals by Owner in Fenway–Kenmore Area

Why Choose Rent By Owner for your Fenway–Kenmore vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Fenway–Kenmore Rentals by Owner

Where are the best neighborhoods to stay in Fenway–Kenmore?

When choosing where to stay in Fenway–Kenmore, Boston, Massachusetts, you’ll find a neighborhood rich in character and convenience. This area offers easy access to renowned sports venues, vibrant dining options, and cultural attractions, making it ideal for travelers seeking an authentic Boston experience. Staying in Fenway–Kenmore provides a central location that allows you to explore the city comfortably while enjoying the lively atmosphere of one of Boston’s most iconic neighborhoods. Whether you're interested in the local arts scene or simply soaking in the urban charm, this neighborhood offers a reliable and accessible base for your visit.

Back Bay

In this vibrant neighborhood, you'll enjoy easy access to upscale shopping, historic architecture, and beautiful waterfront views, making it an ideal area to stay for both leisure and business travelers.

View 341+ Rentals in Back Bay

Allston

Known for its lively atmosphere and diverse dining options, the region offers a more affordable yet energetic environment close to Boston's top entertainment and nightlife venues.

View 67+ Rentals in Allston

South End

This charming neighborhood features picturesque tree-lined streets and eclectic cafes, providing a relaxed setting perfect for exploring local culture while enjoying convenient access to downtown Boston.

View 215+ Rentals in South End

Roxbury

Here, you’ll experience a culturally rich area with community-focused events and parks, offering a welcoming environment for travelers seeking authentic Boston experiences.

View 92+ Rentals in Roxbury

Mission Hill

Set on elevated terrain, this neighborhood provides stunning skyline views and proximity to medical campuses, making it a practical choice for visitors in town for healthcare or academic purposes.

View 3216+ Rentals in Mission Hill

Shawmut

This serene residential area offers peace and quiet while still being within reach of Boston’s bustling city life, ideal for those looking for a relaxing retreat in the city.

View 97+ Rentals in Shawmut

West Fens

Known for its proximity to Fenway Park, the neighborhood is perfect for sports enthusiasts wanting to stay close to game day excitement and local parks.

View 186+ Rentals in West Fens

Medical Center Area

Conveniently located near major healthcare institutions and educational facilities, this area appeals to visitors who prioritize accessibility and professional connections during their stay.

View 3410+ Rentals in Medical Center Area

Best Times to Visit Fenway–Kenmore

When should you plan your Rentals by Owner stay?

Choosing the right time to visit here can enhance your experience, allowing you to enjoy the local ambiance and attractions at their best during your stay in Fenway–Kenmore.

Peak Season Highlights

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Summer (June to August)

During the summer months, you'll find this region bustling with activity, attracting visitors who want to enjoy warm weather and outdoor events.

Average Temperature Daytime: approximately 80°F - Nighttime: around 65°F
autumn
Fall (September to November)

Autumn offers pleasant weather and vibrant foliage, making it an ideal time for travelers seeking comfortable outdoor experiences in the area.

Average Temperature Daytime: around 70°F - Nighttime: roughly 55°F

Off-Season Highlights

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Winter (December to February)

The winter season tends to see fewer visitors, offering a quieter experience with cooler temperatures that are perfect for cozy indoor stays.

Average Temperature Daytime: about 40°F - Nighttime: close to 30°F
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Spring (March to May)

Spring brings milder weather and fewer crowds, providing a peaceful time to explore and enjoy more affordable rental options here.

Average Temperature Daytime: around 55°F - Nighttime: approximately 40°F

Weekly Weather Forecast for Fenway–Kenmore

How to Book Your Fenway–Kenmore vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Fenway–Kenmore

More Top-Rated Rentals by Owner in Fenway–Kenmore Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 access to a private or shared outdoor patio, perfect for relaxing after exploring the city’s attractions.
  • Discover nearby parks and green spaces where you can go jogging, picnicking, or simply unwind in nature.
  • Benefit from on-site bike storage or bike rentals, making it easy to explore the region's vibrant neighborhoods.
  • Take advantage of outdoor seating areas with barbecue grills, ideal for socializing with friends or family.
  • Find accommodations that feature gardens or landscaped courtyards, providing a peaceful retreat in the city.
  • Look for properties with balconies or terraces offering views of the surrounding cityscape or local landmarks.
  • Access outdoor parking facilities to conveniently explore the area by car during your stay here.

Top Attractions Around Fenway–Kenmore

What attractions are nearby?

Within this vibrant neighborhood, you can enjoy a variety of nearby activities that showcase the best of Boston’s cultural and recreational offerings, making it an ideal area for exploring local attractions and experiencing the dynamic energy of the region during your stay.

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Family Activities

  • Fenway Park Tour: Experience the iconic baseball history by taking a guided tour of this historic sports stadium, perfect for sports-loving families visiting the area.
  • The Museum of Fine Arts, Boston: Explore diverse art collections that captivate both kids and adults, making it an educational and engaging activity within reach here.
  • Boston Children's Museum: Enjoy interactive exhibits and hands-on activities designed to entertain and educate children of all ages during your stay in the region.
  • The Emerald Necklace Parks: Take a relaxing stroll or family picnic in the expansive green spaces and scenic waterways that provide outdoor fun near here.
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Adult Activities

  • Visit Fenway Park: Experience an iconic baseball game or take a guided tour of the historic ballpark to immerse yourself in the area's rich sports culture.
  • Explore Museum of Fine Arts, Boston: Discover world-class art collections and exhibitions that highlight the region's vibrant artistic heritage, right within this destination’s proximity.
  • Stroll through the Emerald Necklace: Enjoy scenic walks or bike rides along this picturesque series of parks and waterways nestled nearby, perfect for leisure and relaxation.
  • Enjoy dining in local restaurants: Savor diverse cuisines at eateries around here, offering authentic flavors and a taste of the area's lively culinary scene.

Other Places to Stay in Fenway–Kenmore, MA

House of Blues Boston
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Kenmore Square
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Fenway Park
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Charles River Bike Path
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Back Bay Fens
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New England Conservatory of Music
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Northeastern University
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Boston Museum of Fine Arts
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New England Conservatory Jordan Hall
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Medical Center Area
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Longwood Medical Area
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West Fens
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Fenway–Kenmore Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Take advantage of the area's vibrant culinary scene by trying popular eateries near your rental to experience authentic regional flavors.
  • Utilize public transportation: Make the most of accessible transit options to conveniently explore the city’s attractions and avoid parking hassles in this bustling neighborhood.
  • Book rentals close to key attractions: Choose a rental by owner within walking distance of major venues to maximize your sightseeing time without unnecessary travel.
  • Engage with community events: Keep an eye on local calendars for events or festivals happening nearby to immerse yourself in the area's lively culture and entertainment.

Transportation Options

  • MBTA Green Line Subway: The local light rail provides quick and convenient access to the heart of Boston from your rental in this vibrant neighborhood.
  • Bus Services: Multiple city bus routes serve the area, offering flexible public transportation options for exploring around here.
  • Commuter Rail: Commuter trains connect nearby stations to surrounding suburbs, making day trips outside the city straightforward and comfortable.
  • Taxi and Rideshare Services: Reliable taxi companies and popular ride-sharing apps offer on-demand transportation directly from your accommodation here, ensuring easy travel at any time.

Local Customs Options

  • Red Sox Nation Spirit: Embracing the area's deep-rooted baseball culture, locals and visitors alike cherish the tradition of supporting the Boston Red Sox at Fenway Park.
  • Historic Cheers: The neighborhood's vibrant pub scene celebrates its famous sports bar ambiance, embodying a friendly and spirited welcoming atmosphere.
  • Artistic Appreciation: Connecting with the local arts scene reveals a community proud of its murals and galleries that showcase Boston's creative personality.
  • Neighborhood Hospitality: Engaging in community events and local dining customs reflects the region’s warm and inviting spirit toward both newcomers and residents.

Frequently Asked Questions About Fenway–Kenmore Rentals by Owner

1. What are the top vacation rentals in Fenway–Kenmore?

There are a lot of options in Fenway–Kenmore. If you plan on staying in the Fenway–Kenmore area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Fenway–Kenmore:

2. How many Rentbyowner vacation rentals are available in Fenway–Kenmore?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 199 in the Fenway–Kenmore 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 Fenway–Kenmore. 

3. What is the cancellation policy for a rental by owner in Fenway–Kenmore?

The cancellation policy varies by listing. You should review the specific rental's terms on the listing page or contact the owner directly for detailed information regarding cancellations and associated fees.

4. How do I ensure my reservation in a Fenway–Kenmore rental is secure?

Reservations are secured through the booking platform, which offers secure payment options. For added peace of mind, confirm the listing's reviews and communicate directly with the owner before finalizing your reservation.

5. Are there any extra fees or deposits required when booking through Rent By Owner in this area?

Some listings may include additional fees such as cleaning or service charges, and security deposits may be required. These details are specified on each individual listing, so be sure to review them carefully before completing your booking.

6. What amenities are typically included in rentals here?

Amenities vary depending on the property but often include essentials like Wi-Fi, kitchen access, and laundry facilities. Check the specific listing for a comprehensive list of what is offered during your stay.

7. How close are these rentals to local attractions and public transportation?

Most rentals are conveniently located near public transit options and key attractions in the region. For precise location details and transportation access, refer to the property description and map provided in the listing.

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More Top-Rated Rentals by Owner in Fenway–Kenmore Area