Harbor Island Vacations from $417

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.
Sand Castle Inn
The Shoal La Jolla Beach
WorldMark San Diego - Balboa Park
Southern California Beach Club
City24 Hotel Little Italy Mission Hills

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

Harbor Island Hotel Deals

Sheraton San Diego Resort

Sheraton San Diego Resort

4 out of 5
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

Sheraton San Diego Resort
Wyndham San Diego Bayside

Wyndham San Diego Bayside

4 out of 5
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

Wyndham San Diego Bayside
The DEXTRO Little Italy, BW Premier Collection

The DEXTRO Little Italy, BW Premier Collection

3 out of 5
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

The DEXTRO Little Italy, BW Premier Collection
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.

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Things to do

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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.