294+ Vacation Rentals Near Highland Beach |
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  3. Highland Beach

Villas Rentals - Vacation Rentals in Highland Beach

PRIVATE BEACH, 2 min walk. WIFI, AC, sunny/clean. New Kitchen & screened porch. From US $915
         

10.0 (142 Reviews)
House
PRIVATE BEACH, 2 min walk. WIFI, AC, sunny/clean. New Kitchen & screened porch.
  • Air Conditioner
  • Parking
  • TV

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Sandpiper Cottage From US $325
         

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New
House
Sandpiper Cottage
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Cape View Motel From US $120
         

9.2 (328 Reviews)
Hotel
Cape View Motel
  • Air Conditioner
  • Parking
  • Pool

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4BR historic cottage on Pamet & Cape Cod Bay. Kayak heaven. WIFI. Washer dryer. From US $645
         

9.6 (40 Reviews)
Cottage
4BR historic cottage on Pamet & Cape Cod Bay. Kayak heaven. WIFI. Washer dryer.
  • Parking
  • Pet Friendly
  • TV

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Beautiful backyard pool deeded beach rights From US $833
         

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10.0 (1 Review)
House
Beautiful backyard pool deeded beach rights
  • Air Conditioner
  • Parking
  • Pet Friendly

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Prince of Whales From US $422
         

9.2 (201 Reviews)
Hotel
Prince of Whales
  • Air Conditioner
  • Parking
  • Pet Friendly

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Spacious Contemporary, Walk to Private Tru-Haven Beach From US $959
         

9.6 (31 Reviews)
House
Spacious Contemporary, Walk to Private Tru-Haven Beach
  • Parking
  • TV
  • View

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Sunroom 1 3 Miles to Longnook Beach From US $779
         

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10.0 (1 Review)
House
Sunroom 1 3 Miles to Longnook Beach
  • Air Conditioner
  • Parking
  • View

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Architectural modern home 5 mins to beach! From US $409
         

9.6 (25 Reviews)
House
Architectural modern home 5 mins to beach!
  • Air Conditioner
  • Parking
  • Pet Friendly

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GREAT LOCATION/3 bedroom/bay view/Pond village area From US $654
         

9.8 (39 Reviews)
House
GREAT LOCATION/3 bedroom/bay view/Pond village area
  • Air Conditioner
  • Parking
  • TV

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NEWLY RENOVATED, LARGE, SERENE, SUNNY HOME ON PRIVATE ROAD From US $1,273
         

10.0 (17 Reviews)
House
NEWLY RENOVATED, LARGE, SERENE, SUNNY HOME ON PRIVATE ROAD
  • Air Conditioner
  • Parking
  • TV

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Water View Cottage within Steps to Private Beach From US $233
         

10.0 (73 Reviews)
Cottage
Water View Cottage within Steps to Private Beach
  • Air Conditioner
  • Parking
  • TV

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Charming 2 bedroom rental Pond Village area available June 8-17 From US $377
         

10.0 (58 Reviews)
House
Charming 2 bedroom rental Pond Village area available June 8-17
  • Air Conditioner
  • Parking
  • TV

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Cottage #11 - Spectacular views of Cape Cod Bay on a private association beach! From US $489
         

10.0 (40 Reviews)
Cottage
Cottage #11 - Spectacular views of Cape Cod Bay on a private association beach!
  • Parking
  • TV
  • View

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Beachfront on Private Beach w/AC! From US $549
         

10.0 (30 Reviews)
House
Beachfront on Private Beach w/AC!
  • Air Conditioner
  • Parking
  • TV

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Large, Renovated, Pet Friendly home w/room for everyone! Close to everything. From US $780
         

10.0 (29 Reviews)
House
Large, Renovated, Pet Friendly home w/room for everyone! Close to everything.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cape Escape in North Truro. Completely renovated. 1/2 mile walk to the beach. From US $444
         

10.0 (22 Reviews)
Condo
Cape Escape in North Truro. Completely renovated. 1/2 mile walk to the beach.
  • Air Conditioner
  • Parking
  • TV

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Private Garden-Level Retreat Near Corn Hill Beach - Quiet - Dog Friendly From US $353
         

10.0 (21 Reviews)
Apartment
Private Garden-Level Retreat Near Corn Hill Beach - Quiet - Dog Friendly
  • Air Conditioner
  • Parking
  • Pet Friendly

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Views of Bay Access to Private Beach! From US $265
         

10.0 (15 Reviews)
House
Views of Bay Access to Private Beach!
  • Air Conditioner
  • Parking
  • TV

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Newly updated cozy condo, conveniently located near stunning beaches From US $203
         

10.0 (15 Reviews)
Condo
Newly updated cozy condo, conveniently located near stunning beaches
  • Air Conditioner
  • Parking
  • Pool

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5 Min. Drive to Fisher Beach and Pamet Harbor! From US $365
         

10.0 (13 Reviews)
House
5 Min. Drive to Fisher Beach and Pamet Harbor!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautiful backyard, pool, deeded beach rights! From US $755
         

10.0 (6 Reviews)
House
Beautiful backyard, pool, deeded beach rights!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Stunning Modern Masterpiece on the Beach in Truro RPAM031 From US $3,940
         

10.0 (3 Reviews)
House
Stunning Modern Masterpiece on the Beach in Truro RPAM031
  • Air Conditioner
  • Parking
  • TV

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25-27% off the listed price 2026 6 en-suite, pets, privacy, views, linens, ADA. From US $1,293
         

10.0 (3 Reviews)
House
25-27% off the listed price 2026 6 en-suite, pets, privacy, views, linens, ADA.
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Villas Rentals makes it easy to compare the best listings on Villas Rentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Villas Rentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Highland Beach.

Weather in Highland Beach

View the weather forecast for Highland Beach before booking your Highland Beach Vacation Rentals to confirm your best time to go.

December - February
High 45°F       Low 20°F
March - May
High 63°F       Low 22°F
June - August
High 80°F       Low 57°F
September - November
High 74°F       Low 30°F

Top Attractions Around Highland Beach, MA

Villas Rentals offers a large selection of top attractions around Highland Beach. Research things to do on your vacation before you visit Highland Beach.


Cape Cod National Seashore Pilgrim Monument Cahoon Hollow Beach Race Point Beach Herring Cove Beach Whale-Watching Art House Cape Cod Beaches Coast Guard Beach MacMillan Pier Wellfleet Bay Wildlife Sanctuary Marconi Beach Ballston Beach Truro Vineyards of Cape Cod Provincetown Theater Wellfleet Harbor Actors Theater Nauset Lighthouse Provincetown Town Hall Wellfleet Preservation Hall Pamet River

Highland Beach Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Highland Beach?

Currently, the total number of properties listed in 2026 is over 294 in the Highland Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Highland Beach.