Long Island Holidays - Vacation Rentals in Oak Street Beach

Near Yale and Lighthouse Point Beach Home with Pool! From US $780
         

Walkable New Haven Retreat w/Ocean Views! From US $881
         

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New
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Beachfront Apartment - 8 min from downtown From US $558
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Walkable New Haven Retreat with Ocean Views! From US $797
         

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9.7 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Homewood Suites by Hilton Orange New Haven From US $169
         

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9.2 (1011 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Clear LI Sound waterview, Wedding pics, Yale&Beach From US $982
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Beach Bungalow, walk to beach, private backyard From US $441
         

On the Water Spacious Comfortable Historic Home From US $985
         

3BR Gem, 10 min to Yale, walk to Tweed From US $306
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lovely apartment with Waterview & Patio in New Haven From US $368
         

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Balcony/Terrace
Sunny Beach Cottage close to Yale 1.5 hr from NYC From US $550
         

Spacious 3-BR apartment in brilliant Near Yale University and Hospitals#Apt 5 From US $421
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
2-BR apartment in fantastic New Haven near Yale Hospital and Yale Unv. Apt#9 From US $257
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Walkable New Haven Retreat w/Ocean Views! From US $536
         

9.8 (34 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Jewel of The Cove - Historic Coastal Retreat From US $513
         

McAngel Haven: 5 mins from Yale From US $523
         

9.6 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays From US $824
         

9.6 (14 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Near Yale & Lighthouse Point Beach: Home w/Pool! From US $526
         

Pro Tip: Longislandholidays makes it easy to compare the best listings on Longislandholidays homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Longislandholidays 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 Oak Street Beach.

Weather in Oak Street Beach

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Oak Street Beach Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 151 in the Oak Street Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Oak Street Beach.