Harbor Island Vacation Packages

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Top Holiday Package Deals in Harbor Island

Price found within the past 48 hours. Click for updated prices.

Paradise Point Resort & Spa

Mission Bay

Save 100% on your flight

CA $1,338

per person

Jan 6 - Jan 13

found 4 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to San Diego (SAN)

8.8/10 Excellent! (2,906 reviews)

Room was clean and spacious with lots of drawers for storage. Small refrigerator, no microwave. Lots of extra towels, and an extra pillow. Ironing board and iron, nice spa quality toiletries. Parking close to room but shocked at $50/night charge for parking. Gardens and ponds everywhere, beautiful. Lots of squirrels, birds. Gazebos to hang out in. Several swimming pools, but no outside beverages aloud inside. At night, lots of fire pits available. I don’t recommend premium rooms by the bay if you plan on swimming. Sign said bacteria in water swimming not recommended but view is nice, with several fire pits (bring your own wood).

Reviewed on Oct 15, 2026

The Sofia Hotel

Downtown San Diego

Save 100% on your flight

CA $1,633

per person

Nov 15 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to San Diego (SAN)

8.6/10 Excellent! (2,695 reviews)

Great stay! We appreciated the cold water dispenser on the floor and fridge and microwave. Room had a modern design and controls for lights etc. It was a very reasonable price during a sale. Property had some older carpet and worn surfaces in common areas.

Reviewed on Oct 15, 2026

The Lodge at Torrey Pines

Torrey Pines

Save 100% on your flight

CA $3,110

per person

Dec 25 - Jan 1

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to San Diego (SAN)

9.4/10 Exceptional! (991 reviews)

Alila Marea Beach Resort Encinitas, a Hyatt Luxury Resort

Save 100% on your flight

CA $2,686

per person

Dec 26 - Jan 1

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to San Diego (SAN)

8.8/10 Excellent! (291 reviews)

Pantai Inn

Village of La Jolla

Save 100% on your flight

CA $2,137

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to San Diego (SAN)

9.4/10 Exceptional! (1,008 reviews)

Great place to stay. I would go back again. The location is steps away from the ocean. Nice to take a morning walk along the coast and in the evenings to view the beautiful sunsets. Walkable to the town. The staff was excellent and very accommodating. The free breakfasts were very good with many selections.

Reviewed on Oct 13, 2026

Where to stay in Harbor Island

Find the best Harbor Island areas and neighborhoods for the activities you enjoy most. Learn more about Harbor Island

A grand building with a central fountain, palm trees, and a flag.

Downtown San Diego

3 out of top 10 points of interest in this area

Cultural and financial hub, Downtown San Diego boasts the Symphony, Opera, theaters, museums, and historic sites like Gaslamp Quarter. Enjoy diverse shops, dining, nightlife, and convenient public transport options.

A pier extending into calm waters with people on it and a sandy beach with seaweed and a few individuals.

Pacific Beach

Boasting a lively nightlife scene, Pacific Beach offers miles of sandy shores, a bustling 3.2-mile boardwalk, and attractions like Crystal Pier and Kate Sessions Park. Enjoy local shops, bars, and eateries along the vibrant walkway.

A lively street scene with outdoor seating at various bars and restaurants, including 'The Field' and 'Sloppy Joe's'.

Gaslamp Quarter

Downtown San Diego's historic district boasts Victorian-era buildings, now housing vibrant restaurants, shops, and entertainment venues. Stroll from Broadway to Harbor Drive, and 4th to 6th Avenue, admiring the newly installed gaslamps at Market Street.

A sandy beach with a lifeguard tower, ocean waves, and people in the distance.

Mission Beach

Spanning nearly two miles of oceanfront, this sandbar community offers sunbathing, surfing, and beach volleyball, with nearby attractions like Belmont Park's Giant Dipper Roller Coaster and SeaWorld in Mission Bay Park.

An aerial view of a coastal city with a marina, a large body of water, and a peninsula with buildings.

Mission Bay

1 out of top 10 points of interest in this area

If you're spending some time in Mission Bay, Mission Bay and Ski Beach are top sights worth seeing.

Harbor Island Hotel Deals

Sheraton San Diego Resort

1380 Harbor Island Dr San Diego CA

Fully refundableReserve now, pay when you stay

CA $197

CA $299 total

Oct 25 - Oct 26

includes taxes & fees

Wyndham San Diego Bayside

1355 N Harbor Drive San Diego CA

Fully refundableReserve now, pay when you stay

CA $194

CA $275 total

Oct 27 - Oct 28

includes taxes & fees

8.4/10 Very good! (6,343 reviews)

"Generally a great stay. Definitely a wonderful location. We had a harbor view room and it was great just to sit on the balcony and enjoy the scenery. All the staff were A+ Our bathroom was a little worn looking and the toilet plumbing needed to be adjusted."

Reviewed on Oct 16, 2026

Paradise Point Resort & Spa

1404 Vacation Rd San Diego CA

Fully refundableReserve now, pay when you stay

CA $274

CA $390 total

Nov 1 - Nov 2

includes taxes & fees

8.8/10 Excellent! (2,933 reviews)

"Room was clean and spacious with lots of drawers for storage. Small refrigerator, no microwave. Lots of extra towels, and an extra pillow. Ironing board and iron, nice spa quality toiletries. Parking close to room but shocked at $50/night charge for parking. Gardens and ponds everywhere, beautiful. ..."

Reviewed on Oct 15, 2026

See all 8,612 properties in Harbor Island

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.