Owner Direct Vacation
Rentals in Highland Park
The Best Owner Direct Vacation Rentals in Highland Park. Explore thousands of vacation home rentals, large cabins, and villas near Highland Park
GUESTS
Explore the Best Highland Park Vacation Homes
Looking for the perfect place to stay in Highland Park? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Highland Park character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Highland Park Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Highland Park
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Tuesday Jan 27
Highland Park, Boston
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Highland Park vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Highland Park
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How to Reserve Your Highland Park Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Highland Park Vacation Rental FAQs
1. What are the top vacation rentals in Highland Park?
There are a lot of options in Highland Park. If you plan on staying in the Highland Park area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland Park:
- Fort Hill Inn- Modern City Triplex !*L@K *Minutes to Center! With Parking!
- *Fresh* Modern Triplex in a Classic Boston Row House, Amazing City Views!
- Spacious 2 bedroom apartment
- Cozy Oasis | Near South End
- Spacious 3BR for 10 | Prime Boston Location
- Luxury 3BR 2BA Boston Penthouse
- Bright Brownstone w Terrace+View
- Single family home close to universities and and major hospitals.
- Fresh Modern City Loft Apt! Easy Access to the city!
- "Fort Hill Inn" Sunny, Penthouse Duplex! L@K 3 bed, 2 bath, 1.5 miles Center
2. Which vacation homes in Highland Park are best for families?
If you are looking for a family-friendly vacation home in Highland Park, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland Park:
3. How many vacation rentals are available in Highland Park?
Currently, the total number of properties listed in 2026 is over 61 in the Highland Park area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Highland Park.