Harbor Island Vacations from $316
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.
The Westin San Diego Gaslamp Quarter
Downtown San Diego
Save 100% on your flight
Price was $502, price is now $316 per person
$316
per person
Mar 7 - Mar 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
9/10 Wonderful! (1,002 reviews)
Bathroom in 805 needs attention
Reviewed on Jan 6, 2026
Hilton San Diego Gaslamp Quarter
Downtown San Diego
Save 100% on your flight
Price was $1,567, price is now $927 per person
$927
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
9/10 Wonderful! (232 reviews)
The room was clean and quiet.
Reviewed on Jan 7, 2026
Hyatt Vacation Club at The Welk, San Diego Area
Lawrence Welk Resort Village
Save 100% on your flight
Price was $698, price is now $421 per person
$421
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
8.2/10 Very Good! (1,508 reviews)
Nice room with free amenities. Feels like home
Reviewed on Feb 2, 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
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.
Harbor Island Hotel Deals
Sheraton San Diego Resort
1380 Harbor Island Dr San Diego CA
Fully refundableReserve now, pay when you stay
$207 nightly
The price is $238 total per night from Feb 6 to Feb 7
$238 total
Feb 6 - Feb 7
Total with taxes and fees
8.2/10 Very Good! (3,302 reviews)
clean rooms
Reviewed on Feb 3, 2026
Bay Club Hotel & Marina
2131 Shelter Island Dr San Diego CA
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $164 total per night from Feb 24 to Feb 25
$164 total
Feb 24 - Feb 25
Total with taxes and fees
9/10 Wonderful! (3,354 reviews)
Clean and comfortable room with a nice view of the marina and the water. Excellent breakfast as well.
Reviewed on Feb 4, 2026
Hard Rock Hotel San Diego
207 5th Ave San Diego CA
Fully refundableReserve now, pay when you stay
$266 nightly
The price is $308 total per night from Feb 6 to Feb 7
$308 total
Feb 6 - Feb 7
Total with taxes and fees
8.8/10 Excellent! (3,287 reviews)
Room was very clean and luxurious
Reviewed on Feb 5, 2026
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.
Discover the most popular places to visit in Harbor Island
San Diego Zoo
See nature up-close and personal at one of the country’s largest and most educational zoos.
San Diego Convention Center
Whether you come for Comic-Con or a medical convention, this huge gathering place in the Marina District of San Diego will more than satisfy your needs.
Mission Bay
Mingle with eccentric locals at bohemian beaches, soak up the sun on a Jet Ski and fish from marshy islands at San Diego’s premier water park.
Things to do
San Diego: Museum of Illusions Entry Ticket
$35
per adult
80% of travellers recommend
San Diego Whale Watching & Dolphin Cruise
$71
per adult
88% of travellers recommend
San Diego Old Town Trolley Hop-On Hop-Off Tour
$55
per adult
94% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.