Henry Island holiday homes

We found 225 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Henry Island

Showing deals for:18 Dec - 25 Dec

Living area
Exterior
Great fire pit is perfect for smores.
Living area
Exceptional
(59 reviews)

Luxury four bedroom home on sixteen acres of wooded privacy.

Friday Harbor

8% off
NZ$14,329
for 7 nights, 1 home
NZ$2,047 per night
includes taxes & fees
Luxury four bedroom home on sixteen acres of wooded privacy.
Antique bell over carport
A neighbor viewed from Guesthouse
Studio Kitchenette with Dishwasher and Countertop Oven
House and Guesthouse from Southeast
Exceptional
(163 reviews)

Shared hot tub with meadow view

Friday Harbor

12% off
NZ$3,040
for 7 nights, 1 apartment
NZ$434 per night
includes taxes & fees
Shared hot tub with meadow view
Room
Marina
Property grounds
Terrace/patio
Exceptional
(139 reviews)

Golf Course Guesthouse , Friday Harbor, San Juan Isl.

Friday Harbor

8% off
NZ$2,174
for 7 nights, 1 room
NZ$311 per night
includes taxes & fees
Golf Course Guesthouse , Friday Harbor, San Juan Isl.
View of the buildings on the property.
Beautiful light all year long.
Join us on the beautiful deck to relax and take in the view!
 Cozy sitting area with expansive view over Deer Harbor
Exceptional
(28 reviews)

Madrona Suite - Summer on Orcas Island- rest where sea meets stillness

Deer Harbor

8% off
NZ$3,574
for 7 nights, 1 apartment
NZ$511 per night
includes taxes & fees
Madrona Suite - Summer on Orcas Island- rest where sea meets stillness
Property grounds
Exterior
Interior
Interior
Exceptional
(376 reviews)

Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.

Friday Harbor

8% off
NZ$4,649
for 7 nights, 1 home
NZ$664 per night
includes taxes & fees
Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.
Interior
Interior
Room
Private kitchen
Exceptional
(5 reviews)

Peaceful 1-bedroom condo in charming Friday Harbor

Friday Harbor

8% off
NZ$2,573
for 7 nights, 1 apartment
NZ$368 per night
includes taxes & fees
Peaceful 1-bedroom condo in charming Friday Harbor
Large yard to enjoy playing badminton, corn hole or just enjoying the beauty
Firepit with 2 Adirondack chairs.. This portion of the deck is covered
Property grounds
Covered and open deck w/ 6, seating dining table, firepit, BBQ, yard for games
Exceptional
(107 reviews)

Perfect location to relax, unwind, rejuvinate, explore and enjoy San Juan Island

Friday Harbor

8% off
NZ$5,070
for 7 nights, 1 home
NZ$724 per night
includes taxes & fees
Perfect location to relax, unwind, rejuvinate, explore and enjoy San Juan Island
Interior
Exterior
Interior
Room
Excellent
(20 reviews)

Tahlequah's Place Condo in Downtown Friday Harbor

Friday Harbor

8% off
NZ$2,084
for 7 nights, 1 apartment
NZ$298 per night
includes taxes & fees
Tahlequah's Place Condo in Downtown Friday Harbor
Eat in Bar
Nano doors open to bring the outdoors in.
Property grounds
Spiral Stairs
Exceptional
(212 reviews)

Roche Harbor Bayfront Escape: Luxe Retreat with Kayaks, Deck & Wildlife Views

Friday Harbor

8% off
NZ$6,032
for 7 nights, 1 home
NZ$862 per night
includes taxes & fees
Roche Harbor Bayfront Escape: Luxe Retreat with Kayaks, Deck & Wildlife Views
Room
Nichols Street Suites is above Funk & Junk Antiques, 85 Nichols St.
Private kitchen
Living area
Exceptional
(130 reviews)

Family Friendly In Town Accommodations

Friday Harbor

13% off
NZ$2,462
for 7 nights, 1 room
NZ$352 per night
includes taxes & fees
Family Friendly In Town Accommodations
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Henry Island getaway

Learn about the unique charm of Henry Island with a stay in a holiday home rental. This city has something for everyone. Victoria Clipper Ferry Terminal and Victoria Harbour are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Henry Island

Do you want to find top things to see and do in the city? Venture out of your holiday home and check out everything that makes Henry Island a one-of-a-kind holiday spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Cordova Bay Golf Course (9.8 mi / 15.8 km)
  • Victoria Butterfly Gardens (11.8 mi / 19 km)
  • Orcas Island Golf Course (12.8 mi / 20.6 km)
  • Panorama Recreation Centre (10.7 mi / 17.2 km)
  • Church and State Wines (11.9 mi / 19.1 km)
  • Cedar Hill Golf Course (12.3 mi / 19.8 km)

Exploring the natural landscape of Henry Island

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Henry Island is a great place to spend some time outside. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • San Juan Islands Sculpture Park (2 mi / 3.2 km)
  • San Juan County Park (4.3 mi / 6.8 km)
  • Elk Lake (10.9 mi / 17.5 km)
  • Elk/Beaver Lake Regional Park (11 mi / 17.8 km)
  • Turtleback Mountain (11.2 mi / 18 km)
  • Cadboro Bay (11.4 mi / 18.4 km)

More holiday ideas