Harbor Island Vacations from $318
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The Latest Harbor Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Alila Marea Beach Resort Encinitas, a Hyatt Luxury Resort
Save 100% on your flight
Price was $2,042, price is now $1,044 per person
$1,044
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to San Diego (SAN)
8.8/10 Excellent! (221 reviews)
Staff, sunset views, service, food at Vaga! All good!
Room was spacious and lovely. One issue was that the fire pit area in the room as really wet due to the mist/dew from the weather.
Reviewed on Dec 1, 2025
Margaritaville Hotel San Diego Gaslamp Quarter
Downtown San Diego
Save 100% on your flight
Price was $1,119, price is now $623 per person
$623
per person
Feb 27 - Mar 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
9/10 Wonderful! (1,128 reviews)
Clean room . No closet. Bar tenders were nice and fun!
Reviewed on Dec 14, 2025
Paradise Point Resort & Spa
Mission Bay
Save 100% on your flight
Price was $1,108, price is now $652 per person
$652
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
8.6/10 Excellent! (2,326 reviews)
Everything about this place was awesome including the staff
Reviewed on Dec 13, 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
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
$138 nightly
The price is $158 total per night from Dec 24 to Dec 25
$158 total
Dec 24 - Dec 25
Total with taxes and fees
8.2/10 Very Good! (3,160 reviews)
Room was clean, hotel is well cared for, staff was friendly and helpful.
Reviewed on Dec 19, 2025
Hilton San Diego Airport/Harbor Island
1960 Harbor Island Drive San Diego CA
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $188 total per night from Dec 28 to Dec 29
$188 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (1,224 reviews)
The hotel was perfectly close to many San Diego attractions. Rooms were spacious and clean. Staff was friendly. The food in the Panoramic was good and M&M the server was awesome and funny. I am planning to return.
Reviewed on Dec 12, 2025
Lafayette Hotel & Club
2223 El Cajon Blvd San Diego CA
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $263 total per night from Dec 29 to Dec 30
$263 total
Dec 29 - Dec 30
Total with taxes and fees
9.2/10 Wonderful! (1,342 reviews)
My favorite hotel in San Diego. Staff is always helpful, kind and professional. The rooms are comfortable, clean, eclectic and possibly the best minibar selection of top shelf products anywhere. The property invites you to discover and play and socialize. The bar and food programs are superb.
Reviewed on Dec 17, 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 Whale Watching & Dolphin Cruise
$64
per adult
86% 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.