Harbor Island Vacations from $477

Book a Hotel + Flight or Car together to unlock savings

The Latest Harbor Island Vacation Packages

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

Hotel Z

Downtown San Diego
Save 100% on your flight
$477
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9.2/10 Wonderful! (1,191 reviews)
The Sofia Hotel

The Sofia Hotel

Downtown San Diego
$563
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.6/10 Excellent! (2,695 reviews)
Pantai Inn

Pantai Inn

Village of La Jolla
$1,549
per person
Dec 1 - Dec 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to San Diego (SAN)
9.4/10 Exceptional! (1,008 reviews)
Paradise Point Resort & Spa

Paradise Point Resort & Spa

Mission Bay
Save 100% on your flight
$724
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.8/10 Excellent! (2,906 reviews)
Ocean Villas of Carlsbad

Ocean Villas of Carlsbad

Carlsbad Village
Save 100% on your flight
$1,385
per person
Nov 18 - Nov 23
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to San Diego (SAN)
9/10 Wonderful! (24 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 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

Sheraton San Diego Resort

1380 Harbor Island Dr San Diego CA
Fully refundableReserve now, pay when you stay
$183 nightly
$210 total
Oct 25 - Oct 26
Total with taxes and fees
8.6/10 Excellent! (3,773 reviews)
"Make sure you read the parking sign as you enter in regards to pricing. everything else was great. The room was clean. The beds were comfortable. The staff was great. We didn’t have time to eat breakfast in the morning so we were able to DoorDash Starbucks. We had a wedding to go to so we were running ..."

Reviewed on Oct 17, 2026

Sheraton San Diego Resort
Wyndham San Diego Bayside

Wyndham San Diego Bayside

1355 N Harbor Drive San Diego CA
Fully refundableReserve now, pay when you stay
$182 nightly
$211 total
Oct 22 - Oct 23
Total with taxes and fees
Wyndham San Diego Bayside
Paradise Point Resort & Spa

Paradise Point Resort & Spa

1404 Vacation Rd San Diego CA
$239 nightly
$274 total
Nov 1 - Nov 2
Total with taxes and fees
Paradise Point Resort & Spa
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.

Things to do

San Diego Whale Watching Tour

San Diego Whale Watching & Dolphin Cruise

$71
per adult
88% of travellers recommend
San Diego Whale Watching & Dolphin Cruise
San Diego: Luggage Storage in Marina

San Diego: Luggage Storage in Marina

$11
per adult
San Diego: Luggage Storage in Marina
See all activities in San Diego

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.