Harbor Island Vacations from $417
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The Latest Harbor Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sand Castle Inn
Price was $848, price is now $417 per person
$417
per person
Dec 9 - Dec 15
found 8 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.2/10 Very Good! (483 reviews)
Conveniently located. Spacious room. Best quality and pricing combination in Imperial Beach.
Reviewed on Sep 9, 2025
The Shoal La Jolla Beach
Beach Barber Tract
Save 100% on your flight
Price was $937, price is now $597 per person
$597
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.8/10 Excellent! (1,010 reviews)
Well kept, recently remodeled. A little noisy but I slept well for the mist part. I spent a week there. I would go back.
Reviewed on Oct 3, 2025
WorldMark San Diego - Balboa Park
Downtown San Diego
Save 100% on your flight
Price was $782, price is now $511 per person
$511
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Seattle (SEA) to San Diego (SAN)
8.2/10 Very Good! (89 reviews)
The property was lovely and the staff was incredibly friendly and welcoming.
The location of the property was also good, close to most attractions.
Unfortunately, around the property there were too many homeless people, leaving us slightly uncomfortable when walking in the evenings.
Reviewed on Jul 19, 2025
Southern California Beach Club
Townsite
Save 100% on your flight
Price was $1,531, price is now $1,016 per person
$1,016
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to San Diego (SAN)
9.2/10 Wonderful! (516 reviews)
Great location. Had the old property smell.
Reviewed on Sep 1, 2025
City24 Hotel Little Italy Mission Hills
Middletown
Save 100% on your flight
Price was $1,566, price is now $1,046 per person
$1,046
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
9.6/10 Exceptional! (89 reviews)
Stunning location to everything in San Diego. Beautiful modern excellent architecture and huge space for the price. Only drawback is locating to freeway and loud plane noise. However, this can easily be overlooked for the other great reasons.
Reviewed on Sep 24, 2025
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
2 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
$200 nightly
The price is $230 total per night from Oct 31 to Nov 1
$230 total
Oct 31 - Nov 1
Total with taxes and fees
8.2/10 Very Good! (3,092 reviews)
"Beautiful and friendly"
Reviewed on Oct 8, 2025
Wyndham San Diego Bayside
1355 N Harbor Drive, San Diego, CA
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $205 total per night from Oct 12 to Oct 13
$205 total
Oct 12 - Oct 13
Total with taxes and fees
8.2/10 Very Good! (5,971 reviews)
"Excellent view of the Bay, cruise ships docked at the hotel front door."
Reviewed on Oct 7, 2025
The DEXTRO Little Italy, BW Premier Collection
1617 1st Avenue, San Diego, CA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $129 total per night from Oct 15 to Oct 16
$129 total
Oct 15 - Oct 16
Total with taxes and fees
8.6/10 Excellent! (500 reviews)
"Room was clean and modern. Bed comfy. Was noisy beside the highway. Pool are very underwhelming."
Reviewed on Oct 2, 2025
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 Sunset Cruise from Mission Bay
$40
per adult
78% 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.