Harbor Island Vacations from $635
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The Latest Harbor Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Sofia Hotel
Downtown San Diego
Price was $1,305, price is now $635 per person
$635
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
8.4/10 Very Good! (1,627 reviews)
Clean room, nice area. Really close to most things we wanted to visit. Uber rides were pretty cheap since everything was close by!
Reviewed on Jan 26, 2026
Paradise Point Resort & Spa
Mission Bay
Save 100% on your flight
Price was $1,127, price is now $700 per person
$700
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
8.6/10 Excellent! (2,326 reviews)
Clean. Great location. Hidden treasure. Heated pools.
Reviewed on Jan 25, 2026
Margaritaville Hotel San Diego Gaslamp Quarter
Downtown San Diego
Save 100% on your flight
Price was $1,500, price is now $934 per person
$934
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
9/10 Wonderful! (1,128 reviews)
The room was amazing and the staff was great! Especially Dylan H at the front desk
Reviewed on Jan 26, 2026
Hyatt Vacation Club at The Welk, San Diego Area
Lawrence Welk Resort Village
Save 100% on your flight
Price was $1,074, price is now $669 per person
$669
per person
Mar 28 - Apr 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
8.2/10 Very Good! (1,508 reviews)
The property was beautiful, well managed , great staff.
Reviewed on Jan 24, 2026
The Beau Downtown San Diego Gaslamp Quar
Downtown San Diego
Save 100% on your flight
Price was $1,219, price is now $775 per person
$775
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
8.8/10 Excellent! (535 reviews)
Great room great people
Reviewed on Jan 16, 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
4.5/5(8,497 area reviews)
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
$237 nightly
The price is $273 total per night from Jan 29 to Jan 30
$273 total
Jan 29 - Jan 30
Total with taxes and fees
8.2/10 Very Good! (3,277 reviews)
Clean room pool looked nice was to cold to swim for me I liked the closeness to airport and shuttle to airport perfect for myself
Reviewed on Jan 23, 2026
Bay Club Hotel & Marina
2131 Shelter Island Dr San Diego CA
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $171 total per night from Jan 27 to Jan 28
$171 total
Jan 27 - Jan 28
Total with taxes and fees
9/10 Wonderful! (3,327 reviews)
The room was clean , the view was nice Hot tub and pool are wonderful Thank u
Reviewed on Jan 25, 2026
Manchester Grand Hyatt San Diego
1 Market Pl San Diego CA
Fully refundableReserve now, pay when you stay
$286 nightly
The price is $332 total per night from Feb 6 to Feb 7
$332 total
Feb 6 - Feb 7
Total with taxes and fees
9/10 Wonderful! (2,910 reviews)
Great
Reviewed on Jan 24, 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 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
San Diego: Luggage Storage in Marina
$9
per adult
80% 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.