Fenway–Kenmore holiday lettings

We found 577 holiday rentals — enter your dates for availability

Discover a selection of 117 apartments and other holiday rentals in Fenway–Kenmore that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. At the end of the day, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Fenway Kenmore?
Prices for holiday rentals in Fenway Kenmore vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Fenway Kenmore to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Fenway Kenmore holiday house rentals?
You can find great discounts on house rentals in Fenway Kenmore on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Fenway Kenmore holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Fenway Kenmore with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Fenway Kenmore?
A long-stay holiday rental in Fenway Kenmore is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Fenway Kenmore for a holiday rental?
The best time to visit Fenway Kenmore is during the vibrant summer months of June to August, with July being particularly popular. This season attracts a bustling crowd eager to enjoy the lively option, particularly those interested in the rich cultural experiences and outdoor activities the area has to offer. The warm temperatures, typically ranging from 20 to 30 degrees Celsius, provide superb conditions for exploring nearby attractions, including the iconic Fenway Park and beautiful public gardens.

In July, the neighbourhood comes alive with various events and festivals, making it an excellent choice for travellers seeking entertainment and social experiences. Visitors can enjoy outdoor dining, stroll through local markets, and take in the vibrant street life, all while soaking up the warm summer sun.

If you're looking for a more budget-friendly option, consider planning your visit in December. While this month may be quieter, it offers a unique charm with festive decorations and a chance to experience the holiday spirit in the city. Plus, accommodation rates tend to be lower, providing excellent value for your stay.
How early should I book a Fenway Kenmore holiday rental?
Book your Fenway Kenmore holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Fenway Kenmore, Massachusetts, United States of America?
In Fenway Kenmore, visitors can enjoy a variety of attractions that showcase the area's cultural and historical significance. One of the main highlights is Fenway Park, home to the Boston Red Sox, where sports enthusiasts can catch a game or take a guided tour of this iconic ballpark. The surrounding area is rich with eateries and pubs that offer a lively option on game days.

Another great attraction is the Museum of Fine Arts, which boasts an extensive collection of artwork from around the world and frequently hosts special exhibitions. Just a short stroll away, the Isabella Stewart Gardner Museum captivates with its unique architecture and stunning courtyard, making it a favourite among art lovers.

For those interested in science and natural history, the nearby Boston Museum of Science provides engaging exhibits and an IMAX theatre, superb for families.
Can I change or cancel my Fenway Kenmore home rental booking on Vrbo?
To find Fenway Kenmore holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Fenway Kenmore holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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