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.

Hotel Z

Downtown San Diego

CA $1,187

per person

Nov 17 - Nov 24

found 24 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to San Diego (SAN)

9.2/10 Wonderful! (1,129 reviews)

Very nice and helpful

Reviewed on Aug 31, 2026

The Sofia Hotel

Downtown San Diego

CA $1,335

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to San Diego (SAN)

8.6/10 Excellent! (2,550 reviews)

Margaritaville Hotel San Diego Gaslamp Quarter

Downtown San Diego

CA $2,184

per person

Oct 4 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to San Diego (SAN)

9/10 Wonderful! (1,516 reviews)

Great staff, pillows and mattress should be updated

Reviewed on Sep 1, 2026

Fairmont Grand Del Mar

Carmel Valley

CA $2,099

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to San Diego (SAN)

9.4/10 Exceptional! (1,001 reviews)

Rooms are spacious, the cleaning staff is not great though. Our room was cleaned late and very subpar.

Reviewed on Aug 30, 2026

Guesthouse Hotel at La Valle

CA $1,603

per person

Nov 7 - Nov 14

found 21 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to San Diego (SAN)

9.2/10 Wonderful! (213 reviews)

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 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.

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.

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 Mission and Pacific Beaches 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 $211

CA $312 total

Sep 7 - Sep 8

includes taxes & fees

Manchester Grand Hyatt San Diego

1 Market Pl San Diego CA

Fully refundableReserve now, pay when you stay

CA $276

CA $395 total

Sep 7 - Sep 8

includes taxes & fees

9/10 Wonderful! (2,833 reviews)

"The room appeared to be newly refurbished and the bathroom was nice. The main lobby looks amazing."

Reviewed on Sep 1, 2026

Paradise Point Resort & Spa

1404 Vacation Rd San Diego CA

Fully refundableReserve now, pay when you stay

CA $291

CA $408 total

Sep 8 - Sep 9

includes taxes & fees

See all 8,562 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.