Vacation Rentals with Pool in Kenmore Square, MA: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Massachusetts

  5.  Boston
  6.  Kenmore Square

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103 Best Vacation Rentals with Pool in Kenmore Square (Starting from $210)

Spacious 2bed 2bath, King bed, steps fenway park
Spacious 2bed 2bath, King bed, steps fenway park
Apartment
Boston, MA, USA
0.4k from Kenmore Square center

Pet Friendly, Barbecue/Outdoor Cooking, Air Conditioner, Pool, Security/Safety, Child Friendly

2 Bedrooms4 Guests
New to Booking
$600
Average price / night
Check Availability
Walk to the Bay! Ships, Dining & Cambridge Minutes Away (KING BED,POOL)
Walk to the Bay! Ships, Dining & Cambridge Minutes Away (KING BED,POOL)
Apartment
Cambridge, MA, 02139, United States
1.3k from Kenmore Square center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Elevator, Fireplace

3 Bedrooms20 Guests
2.0

Review score

3 reviews

$1541
Average price / night
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An apartment like no other, heart of fenway Boston
An apartment like no other, heart of fenway Boston
Apartment
Boston, MA, USA
0.7k from Kenmore Square center

Pet Friendly, Internet, Security/Safety, Pool, Air Conditioner, Child Friendly

2 Bedrooms4 Guests
New to Booking
$399
Average price / night
Check Availability
Cambridge Luxury Near Harvard & MIT 150” Home Theater Airport Shuttle Netflix
Cambridge Luxury Near Harvard & MIT 150” Home Theater Airport Shuttle Netflix
Apartment
Cambridge, MA, 02139, United States
1.4k from Kenmore Square center

AC, Barbecue, Breakfast Available, Crib, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

2 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1695
Average price / night
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Luxury Bliss Boston
Luxury Bliss Boston
Apartment
Cambridge, MA, USA
1.1k from Kenmore Square center

Apartments, Luxury, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

3 Bedrooms20 Guests
New to Booking
$999
Average price / night
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Raffles Pied-A-Tier Studio
Raffles Pied-A-Tier Studio
Condo
Boston, MA, 02116, United States
1.8k from Kenmore Square center

AC, Balcony, Breakfast Available, Dryer, Elevator, Fitness Equipment, Heater, Hot Tub, Internet

1 Bedroom2 Guests
New to Booking
$788
Average price / night
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Central Serene Condo King Bed by MIT Harvard GYM
Central Serene Condo King Bed by MIT Harvard GYM
Apartment
Cambridge, MA, USA
1.7k from Kenmore Square center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Places to stay, Family, Condos

2 Bedrooms7 Guests
9.2

Superb

5 reviews

$688
Average price / night
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Luxury 2BR/2BA | Prime Downtown Boston
Luxury 2BR/2BA | Prime Downtown Boston
Apartment
Boston, MA, 02111, United States
2.5k from Kenmore Square center

AC, Internet, Kitchen, No Smoking, Pool, TV, Washer

2 Bedrooms4 Guests
New to Booking
$1012
Average price / night
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Upscale Penthouse near MIT Harvard Central Square
Upscale Penthouse near MIT Harvard Central Square
Apartment
Cambridge, MA, USA
1.7k from Kenmore Square center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom5 Guests
9.0

Fabulous

1 reviews

$680
Average price / night
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Luxury King Apartment - 2 Bedroom, Amazing Views - South End Boston
Luxury King Apartment - 2 Bedroom, Amazing Views - South End Boston
Apartment
Boston, MA, 02118, United States
2.6k from Kenmore Square center

AC, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms8 Guests
3.4

Review score

3 reviews

$716
Average price / night
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Well-located Kendall Sq 1BR w courtyard BOS-388
Well-located Kendall Sq 1BR w courtyard BOS-388
Apartment
Boston, MA, USA
2.1k from Kenmore Square center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$217
Average price / night
Check Availability
Modern Boston 2BR Apt. | Prime Downtown Location
Modern Boston 2BR Apt. | Prime Downtown Location
Apartment
Boston, MA, 02118, United States
2.6k from Kenmore Square center

AC, Internet, Kitchen, Living Area, Pool, TV, Washer

2 Bedrooms4 Guests
New to Booking
$1046
Average price / night
Check Availability
Global Luxury Suites in South End
Global Luxury Suites in South End
Apartment
Kenmore Square, Boston, Massachusetts, USA
2.6k from Kenmore Square center

Apartments, Luxury, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay

40 Bedrooms9 Guests
New to Booking
$234
Average price / night
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Affordable Luxury 1BR | Business & Fitness Center| Downtown Boston
Affordable Luxury 1BR | Business & Fitness Center| Downtown Boston
Apartment
Boston, MA, 02118, United States
2.7k from Kenmore Square center

AC, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom3 Guests
New to Booking
$353
Average price / night
Check Availability
Harmony Medical Suites on Canal
Harmony Medical Suites on Canal
Apartment
Kenmore Square, Boston, Massachusetts, USA
2.6k from Kenmore Square center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Pet Friendly, Wheelchair Accessible

4 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$210
Average price / night
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Spacious Downtown 1BR | Laundry In-unit | High Ceilings
Spacious Downtown 1BR | Laundry In-unit | High Ceilings
Apartment
Boston, MA, 02118, United States
2.7k from Kenmore Square center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom3 Guests
New to Booking
$353
Average price / night
Check Availability
South End Club Suites by Orchard
South End Club Suites by Orchard
Apartment
Boston, MA, USA
2.7k from Kenmore Square center

Internet, Pool, Balcony/Terrace, Kitchen, Parking, Pet Friendly, Air Conditioner

3 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$344
Average price / night
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Furnished Downtown 1BR | Gym & Yoga | South End
Furnished Downtown 1BR | Gym & Yoga | South End
Apartment
Boston, MA, 02118, United States
2.7k from Kenmore Square center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom3 Guests
New to Booking
$353
Average price / night
Check Availability
Boston Royale Club Suites Family Collection by Orchard Group
Boston Royale Club Suites Family Collection by Orchard Group
Apartment
Boston, MA, USA
2.7k from Kenmore Square center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay, Family, Accessible hotels

2 Bedrooms5 Guests
New to Booking
$504
Average price / night
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Sleek 1BR Near Beacon Hill | Great Amenities | Downtown Boston
Sleek 1BR Near Beacon Hill | Great Amenities | Downtown Boston
Apartment
Boston, MA, 02118, United States
2.7k from Kenmore Square center

AC, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom3 Guests
New to Booking
$353
Average price / night
Check Availability
Central Boston Two-Bedroom Two-Bath Suite
Central Boston Two-Bedroom Two-Bath Suite
Apartment
Boston, MA, USA
2.7k from Kenmore Square center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay

2 Bedrooms7 Guests
New to Booking
$1760
Average price / night
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Ideal for Medical Professionals! South End Boston 1BR | WiFi & Laundry
Ideal for Medical Professionals! South End Boston 1BR | WiFi & Laundry
Apartment
Boston, MA, 02118, United States
2.7k from Kenmore Square center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom3 Guests
New to Booking
$353
Average price / night
Check Availability
The Splendid One-Bedroom Sanctuary in the Boston
The Splendid One-Bedroom Sanctuary in the Boston
Apartment
Boston, MA, USA
2.7k from Kenmore Square center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$736
Average price / night
Check Availability
On-site Theater! 1BR | W/D | Desk | WiFi | Downtown Boston
On-site Theater! 1BR | W/D | Desk | WiFi | Downtown Boston
Apartment
Boston, MA, 02118, United States
2.7k from Kenmore Square center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom3 Guests
New to Booking
$353
Average price / night
Check Availability
Medical Centers Nearby | 1BR | Desk & WiFi | Downtown Boston
Medical Centers Nearby | 1BR | Desk & WiFi | Downtown Boston
Apartment
Boston, MA, 02118, United States
2.7k from Kenmore Square center

AC, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom3 Guests
New to Booking
$353
Average price / night
Check Availability
Sunlit 1BR | Full Kitchen + In-unit Laundry | Close to Hospitals
Sunlit 1BR | Full Kitchen + In-unit Laundry | Close to Hospitals
Apartment
Boston, MA, 02118, United States
2.7k from Kenmore Square center

AC, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom3 Guests
New to Booking
$353
Average price / night
Check Availability
close to subway 1 BR | near Restaurant Row
close to subway 1 BR | near Restaurant Row
Apartment
Boston, MA, 02118, United States
2.7k from Kenmore Square center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom3 Guests
New to Booking
$352
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Kenmore Square.

Where to stay in Kenmore Square? Best neighborhoods & areas

Kenmore Square Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 103 verified vacation rentals with a pool in Kenmore Square. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Kenmore Square vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $210 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Kenmore Square offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Kenmore Square welcome pets. Currently, 73 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Kenmore Square often include additional outdoor features such as Pool, Pet Friendly, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Kenmore Square offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.