Harbor Island Vacation Packages
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Top Harbor Island vacation package deals
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Little Italy Inn - Limited Service Apart Hotel
Downtown San Diego
8.4/10 Very Good! (117 reviews)
Jun 15 - Jun 20
5 night stay
Boston (BOS) to San Diego (SAN)
JetBlue Airways • Roundtrip • Coach
Price was $748, price is now $464 per person
$464
per person
found 2 hours ago
It was very simple and affordable. The location was excellent. A couple blocks walk to great restaurants and a 15 walk to sea front. Highly recommend.
Reviewed on Nov 6, 2025
3.5-star property
The Sofia Hotel
Downtown San Diego
8.6/10 Excellent! (1,868 reviews)
Jun 14 - Jun 19
5 night stay
Boston (BOS) to San Diego (SAN)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,309, price is now $678 per person
$678
per person
found 1 day ago
Beautiful historical hotel, amazing location a few minutes from the port, incredibly fast checkin, room had character and stay was perfect
Reviewed on Jan 5, 2026
4.0-star property
The Westin San Diego Gaslamp Quarter
Downtown San Diego
9/10 Wonderful! (1,003 reviews)
Jun 14 - Jun 19
5 night stay
Boston (BOS) to San Diego (SAN)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,292, price is now $725 per person
$725
per person
found 1 day ago
We had a very pleasant stay at the hotel. The room was clean and specious, and the service staff were nice and helpful.
Reviewed on Jan 25, 2026
3.0-star property
Urban Boutique Hotel
Downtown San Diego
8.6/10 Excellent! (1,274 reviews)
Jun 17 - Jun 25
8 night stay
Boston (BOS) to San Diego (SAN)
JetBlue Airways • Coach
San Diego (SAN) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $2,809, price is now $1,740 per person
$1,740
per person
found 23 hours ago
Love the location. Walkable from the trolley, friendly staff. Quiet, safe I’ll be coming back for sure.
Reviewed on Jul 28, 2025
4.0-star property
Paradise Point Resort & Spa
Mission Bay
8.6/10 Excellent! (2,489 reviews)
Jun 14 - Jun 19
5 night stay
Boston (BOS) to San Diego (SAN)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,330, price is now $842 per person
$842
per person
found 1 day ago
The view was great. The stay was pleasant. We we were caught off guard with the resort fees, amenities and daily parking costs but overall a great stay.
Reviewed on Apr 6, 2026
Top rated hotels for your Harbor Island vacation package
Sheraton San Diego Resort
1380 Harbor Island Dr San Diego CA
0.52 mi from Harbor Island
$185 nightly
The price is $213 total per night
$213 total
Apr 12 - Apr 13
Total with taxes and fees
Guests of Sheraton San Diego Resort have access to a marina, 3 outdoor pools, and a 24-hour gym. Parking is USD 55 per night (USD 67 per night for valet parking)—but if you prefer not to drive, catch a ride in the free airport shuttle during limited hours. Multilingual staff at the 24-hour front desk can assist with luggage storage, dry cleaning/laundry, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include 2 hot tubs, free WiFi in public areas, and a conference center.
Pool
Hot Tub
Paradise Point Resort & Spa
1404 Vacation Rd San Diego CA
Free Cancellation
Reserve now, pay when you stay
3.92 mi from Harbor Island
$199 nightly
The price is $229 total per night
$229 total
Apr 12 - Apr 13
Total with taxes and fees
Paradise Point Resort & Spa features a marina, a full-service spa, and 5 outdoor pools. Self parking is available for USD 49 per night. The front desk has multilingual staff on hand 24/7 to help with luggage storage, securing valuables, and dry cleaning/laundry. Other amenities at this beach resort include a gym, 5 hot tubs, and a sauna.
Pool
Hot Tub
Best Western Seven Seas
411 Hotel Circle South San Diego CA
Free Cancellation
Reserve now, pay when you stay
3.39 mi from Harbor Island
$82 nightly
The price is $94 total per night
$94 total
Apr 14 - Apr 15
Total with taxes and fees
Guests of Best Western Seven Seas have access to an outdoor pool, a gym, and 2 hot tubs. Free parking is included with your stay. The front desk has multilingual staff on hand 24/7 to help with luggage storage, tours or tickets, and securing valuables. Additional amenities include free WiFi in public areas, conference space, and a business center.
Pool
Hot Tub
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.