
Harbor Island Vacation Packages
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Price found within the past 48 hours. Click for updated prices.

2.5-star property
Los Bungalows
8.2/10 Very Good! (523 reviews)
May 29 - May 31
2 night stay
Denver (DEN) to San Diego (SAN)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $553, price is now $342 per person
$342
per person
found 1 day ago
Great stay as usual. I absolutely love staying here.
Reviewed on Nov 27, 2023

3.5-star property
The Sofia Hotel
Downtown San Diego
8.6/10 Excellent! (1,868 reviews)
Jun 15 - Jun 22
7 night stay
Boston (BOS) to San Diego (SAN)
Alaska Airlines • Roundtrip • Coach
Price was $2,530, price is now $1,180 per person
$1,180
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

4.0-star property
Kona Kai San Diego
Point Loma
8.2/10 Very Good! (1,006 reviews)
Jun 17 - Jun 20
3 night stay
Seattle (SEA) to San Diego (SAN)
Southwest Airlines • Non-stop • Coach
San Diego (SAN) to Seattle (SEA)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $930, price is now $604 per person
$604
per person
found 18 hours ago
When we travel to San Diego, we always stay on Shelter Island because we like the area. The staff was very friendly and helpful. For the price, Kona Kai is not worth the amount of money you pay to stay there. The resort was nice, but the cost of the rooms and resort fees are excessive. I believe the other hotels on the island are just as nice and far more affordable. Other issues: the bar at the adult pool closed at 5pm on Thursday, the hair dryer in our room was sticking with hair on it, the bathroom door was a barn door and did not lock- very little privacy, and the room was a bit dusty. My family enjoyed the fire pits at night fall and our view of the marina was nice.
Reviewed on Oct 20, 2025

2.5-star property
Little Italy Inn - Limited Service Apart Hotel
Downtown San Diego
8.4/10 Very Good! (117 reviews)
May 28 - May 31
3 night stay
Boston (BOS) to San Diego (SAN)
American Airlines • Non-stop • Coach
San Diego (SAN) to Boston (BOS)
Alaska Airlines • Non-stop • Coach
Price was $541, price is now $364 per person
$364
per person
found 1 day 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
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
The price is $213 total per night
$213 total
per night
Apr 12 - Apr 13
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
The price is $229 total per night
$229 total
per night
Apr 12 - Apr 13
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
The price is $94 total per night
$94 total
per night
Apr 14 - Apr 15
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.