Trailride - Vacation Rentals in Sherwood Beach

Waimanalo Beach Cottages From US $507
         

8.8 (31 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Hawaii's Hidden Hideaway Bed & Breakfast From US $325
         

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8.4 (67 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Bedding/Linens
Lanikai Ohana Hale From US $976
         

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New
House
  • Air Conditioner
  • Parking
  • Pool
Hale Pohaku, Waimanalo - Lic.#1990/NUC-1689 From US $1,433
         

Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast From US $386
         

9.2 (100 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Hale Mokulua - Lanikai w/heated pool, spa, steps to Beach! From US $1,121
         

Ocean View Cottage with Separate Suite From US $364
         

Ocean views and Private pool - Mariners Ridge Home From US $511
         

Steps to beach, tropical garden and private pool From US $650
         

9.2 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen From US $255
         

10.0 (5 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Kailua Home Pool & Spa with amazing views From US $340
         

9.8 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Pro Tip: Trailride makes it easy to compare the best listings on Trailride homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Trailride 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 Sherwood Beach.

Weather in Sherwood Beach

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

December - February
High 81°F       Low 67°F
March - May
High 85°F       Low 70°F
June - August
High 89°F       Low 74°F
September - November
High 89°F       Low 73°F

Sherwood Beach Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Sherwood Beach?
How many vacation rentals are available in Sherwood Beach?

Currently, the total number of properties listed in 2026 is over 148 in the Sherwood Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sherwood Beach.