Oceanfront Rentals in Highland Park, MA: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
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  4.  Massachusetts

  5.  Boston
  6.  Highland Park

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74 Best Oceanfront Rentals in Highland Park (Starting from $151)

Perrin Place Unit 1
Perrin Place Unit 1
Apartment
Boston, MA, USA
1.4k from Highland Park center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Self-catering

5 Bedrooms12 Guests
8.7

Fabulous

32 reviews

$344
Average price / night
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Lovely two bedroom Apartment on a two floor unit.\n
Lovely two bedroom Apartment on a two floor unit.\n
Condo
Boston, MA, 02119, United States
0.4k from Highland Park center

AC, Balcony, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$172
Average price / night
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Perrin Place Unit 3
Perrin Place Unit 3
Apartment
Boston, MA, USA
1.4k from Highland Park center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Self-catering

3 Bedrooms6 Guests
8.6

Fabulous

26 reviews

$430
Average price / night
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Uber Cool! Modern City Triplex +Close to center
Uber Cool! Modern City Triplex +Close to center
Apartment
boston, MA, 02119-0000, United States
0.5k from Highland Park center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

4 Bedrooms8 Guests
9.2

Superb

10 reviews

$704
Average price / night
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2 bedroom Boston condo in Jamaica Plain with parking
2 bedroom Boston condo in Jamaica Plain with parking
Apartment
Boston, MA, USA
1.4k from Highland Park center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

2 Bedrooms6 Guests
9.0

Fabulous

10 reviews

$235
Average price / night
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Extremely clean and Affordable.
Extremely clean and Affordable.
Apartment
Boston, MA, 02119, United States
1.3k from Highland Park center

AC, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Toys

3 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$241
Average price / night
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Luxury Furnished Apartments by Hyatus Boston South Bay
Luxury Furnished Apartments by Hyatus Boston South Bay
Apartment
Boston, MA, USA
2.6k from Highland Park center

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

6 Bedrooms6 Guests
New to Booking
$18040
Average price / night
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Upscale Unit 1 at Perrin Place
Upscale Unit 1 at Perrin Place
Apartment
Boston, MA, 02119, United States
1.4k from Highland Park center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
9.2

Superb

47 reviews

$343
Average price / night
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Franklin Park nearby
Franklin Park nearby
Apartment
Boston, MA, USA
2.9k from Highland Park center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Jacuzzis, Places to stay, Family

1 Bedroom4 Guests
8.7

Fabulous

12 reviews

$190
Average price / night
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UltraLuxe Apt in Boston Brownstone2 in Prime Location
UltraLuxe Apt in Boston Brownstone2 in Prime Location
Apartment
Brookline, MA, 02446, United States
2.4k from Highland Park center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.8

Exceptional

79 reviews

$678
Average price / night
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Global Luxury Suites in South End
Global Luxury Suites in South End
Apartment
Highland Park, Boston, Massachusetts, USA
3.0k from Highland Park 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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ASTONISHING 1 BEDROOM PARLOR, WELL APPOINTED, -SOUTH END BOSTON -BEST LOCATION
ASTONISHING 1 BEDROOM PARLOR, WELL APPOINTED, -SOUTH END BOSTON -BEST LOCATION
Apartment
Boston, MA, 02118, United States
2.7k from Highland Park center

AC, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
10.0

Exceptional

52 reviews

$649
Average price / night
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Boston Royale Club Suites Family Collection by Orchard Group
Boston Royale Club Suites Family Collection by Orchard Group
Apartment
Boston, MA, USA
3.1k from Highland Park 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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World Cup Group Stay 5BR Sleeps 16 Near Train Downtown\n
World Cup Group Stay 5BR Sleeps 16 Near Train Downtown\n
House
Boston, MA, 02122, United States
2.7k from Highland Park center

AC, Balcony, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms15 Guests
8.8

Fabulous

8 reviews

$1302
Average price / night
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Sunny convenient home w/private patio! Easy walk to everything!
Sunny convenient home w/private patio! Easy walk to everything!
Apartment
Boston, MA, USA
3.7k from Highland Park center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay, Self-catering

1 Bedroom4 Guests
7.2

Good

4 reviews

$435
Average price / night
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Super Location Boston 3 1/2,bd. Apt. Driveway Parking
Super Location Boston 3 1/2,bd. Apt. Driveway Parking
Apartment
Boston, MA, 02125, United States
2.8k from Highland Park center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
9.6

Exceptional

105 reviews

$318
Average price / night
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North End TD Garden Condo Shared Pool & Rooftop
North End TD Garden Condo Shared Pool & Rooftop
House
Boston, MA, USA
5.0k from Highland Park center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

2 Bedrooms7 Guests
8.0

Good

4 reviews

$825
Average price / night
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Boston Spacious Apartment with private outdoor patio
Boston Spacious Apartment with private outdoor patio
Apartment
Boston, MA, 02125, United States
3.0k from Highland Park center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
8.8

Fabulous

10 reviews

$862
Average price / night
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Global Luxury Suites at Boston Seaport
Global Luxury Suites at Boston Seaport
Apartment
Boston, MA, USA
5.0k from Highland Park center

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

21 Bedrooms9 Guests
New to Booking
$151
Average price / night
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Panoramic view, large deck, ground floor apartment, walk to subway and beach
Panoramic view, large deck, ground floor apartment, walk to subway and beach
Apartment
Boston, MA, 02125, United States
3.0k from Highland Park center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Heater, Internet

1 Bedroom3 Guests
9.4

Superb

110 reviews

$215
Average price / night
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3BR Group Stay Sleeps 12 Near Train Downtown
3BR Group Stay Sleeps 12 Near Train Downtown
House
Boston, MA, 02122, United States
3.1k from Highland Park center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms12 Guests
9.0

Fabulous

21 reviews

$903
Average price / night
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Elegant Back Bay Brownstone-Comm Av 1+ Bed - 1 Week Min, beyond 2 wks considered
Elegant Back Bay Brownstone-Comm Av 1+ Bed - 1 Week Min, beyond 2 wks considered
Condo
Boston, MA, 02116, United States
3.1k from Highland Park center

AC, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms3 Guests
9.6

Exceptional

34 reviews

$581
Average price / night
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12BR Private Compound Sleeps 35+ Backyard & Parking
12BR Private Compound Sleeps 35+ Backyard & Parking
House
Boston, MA, 02122, United States
3.2k from Highland Park center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

12 Bedrooms40 Guests
9.2

Superb

7 reviews

$5444
Average price / night
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Lovely Two Bedroom Condo in South Boston
Lovely Two Bedroom Condo in South Boston
Condo
Boston, MA, 02127, United States
3.3k from Highland Park center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
8.0

Good

7 reviews

$582
Average price / night
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Excellent 2 bedroom condo in South Boston
Excellent 2 bedroom condo in South Boston
Condo
Boston, MA, 02127, United States
3.3k from Highland Park center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
9.8

Exceptional

38 reviews

$467
Average price / night
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Lg suite for up to 8 ppl/3 floor
Lg suite for up to 8 ppl/3 floor
Condo
Boston, MA, 02125, United States
3.4k from Highland Park center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms8 Guests
9.6

Exceptional

16 reviews

$539
Average price / night
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Lg Suite for up to 8 ppl/1 floor
Lg Suite for up to 8 ppl/1 floor
Condo
Boston, MA, 02125, United States
3.4k from Highland Park center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms8 Guests
9.0

Fabulous

14 reviews

$551
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 Oceanfront Rentals in Highland Park.

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Highland Park Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 74 verified oceanfront rentals in Highland Park. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Highland Park vary depending on the property size, exact beachfront location, and season. Rates typically start from around $151 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Highland Park offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Highland Park welcome pets. Currently, 24 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Highland Park often include features designed for a comfortable coastal stay, such as Oceanfront, View, and Ocean View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.