Harbor Island Vacations from $535

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The Latest Harbor Island Vacation Packages

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The Beau Hotel Gaslamp Quarter San Diego

The Beau Hotel Gaslamp Quarter San Diego

Downtown San Diego
Save 100% on your flight
$535
per person
Oct 25 - Oct 31
found 22 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.8/10 Excellent! (906 reviews)
A million degrees in the room. Impossible to sleep. The AC doesn’t work . Night time staff guy gaslighting me. Would never stay here again.

Reviewed on Aug 21, 2026

The Sofia Hotel

The Sofia Hotel

Downtown San Diego
$618
per person
Sep 24 - Sep 28
found 14 hours ago
Roundtrip flight included
Dallas (DAL) to San Diego (SAN)
8.6/10 Excellent! (2,462 reviews)
Hotel stay was excellent! Room was great! Super clean! Our only issue was was parking. When we first booked our hotel back in May, parking was listed as $40/ day. At check-in, we were told parking had increased to $58. I asked for the original pricing to be honored which it was however, the staff checking us in appeared bothered and annoyed. I certainly was taken back from the abruptness and rude demeanor of the clerk after asking for an adjustment. After a brief conversation, I was advised the charge would be adjusted. I certainly did not have an issue with the parking itself. The parking staff were quite helpful and it is understandable the parking lot was full & it would be tandem parking as we were close to downtown. My biggest issue was at checkout when I noticed my bill and was charged for the increased parking price $58/day! When I brought it up to the staff at checkout, she apologized however, said she could not adjust as there were no notes regarding the change. We have no complaints about the room or the area. We think it’s beautiful but perhaps be a bit more transparent with the parking. And train your staff to be more hospitable ;)

Reviewed on Aug 22, 2026

Los Bungalows

Los Bungalows

Save 100% on your flight
$567
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.2/10 Very Good! (546 reviews)
The location of this property is fantastic! Unfortunately, the beach was closed because of a sewage contamination. The parking is a challenge as the lot is very small. Our room was in fairly good shape, but the floors were filthy.

Reviewed on Aug 20, 2026

Ocean Villas of Carlsbad

Ocean Villas of Carlsbad

Carlsbad Village
Save 100% on your flight
$1,271
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9/10 Wonderful! (20 reviews)
Great location and incredible views. Large deck and living room. Ellie in the office is great

Reviewed on Jun 17, 2026

Ocean Park Inn

Ocean Park Inn

Pacific Beach
Save 100% on your flight
$645
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9.4/10 Exceptional! (1,009 reviews)

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
A grand building with a central fountain, palm trees, and a flag.

Downtown San Diego

3 out of top 10 points of interest in this area

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.

A pier extending into calm waters with people on it and a sandy beach with seaweed and a few individuals.

Pacific Beach

Boasting a lively nightlife scene, Pacific Beach offers miles of sandy shores, a bustling 3.2-mile boardwalk, and attractions like Crystal Pier and Kate Sessions Park. Enjoy local shops, bars, and eateries along the vibrant walkway.

A sandy beach with a lifeguard tower, ocean waves, and people in the distance.

Mission Beach

Spanning nearly two miles of oceanfront, this sandbar community offers sunbathing, surfing, and beach volleyball, with nearby attractions like Belmont Park's Giant Dipper Roller Coaster and SeaWorld in Mission Bay Park.

A lively street scene with outdoor seating at various bars and restaurants, including 'The Field' and 'Sloppy Joe's'.

Gaslamp Quarter

Downtown San Diego's historic district boasts Victorian-era buildings, now housing vibrant restaurants, shops, and entertainment venues. Stroll from Broadway to Harbor Drive, and 4th to 6th Avenue, admiring the newly installed gaslamps at Market Street.

An aerial view of a coastal city with a marina, a large body of water, and a peninsula with buildings.

Mission Bay

1 out of top 10 points of interest in this area

If you're spending some time in Mission Bay, Mission Bay and Mission and Pacific Beaches are top sights worth seeing.

Harbor Island Hotel Deals

Sheraton San Diego Resort

Sheraton San Diego Resort

1380 Harbor Island Dr San Diego CA
Fully refundableReserve now, pay when you stay
$196 nightly
$225 total
Sep 2 - Sep 3
Total with taxes and fees
8.6/10 Excellent! (3,668 reviews)
"This is a beautiful property with an abundant of activities."

Reviewed on Aug 21, 2026

Sheraton San Diego Resort
Paradise Point Resort & Spa

Paradise Point Resort & Spa

1404 Vacation Rd San Diego CA
Fully refundableReserve now, pay when you stay
$245 nightly
$282 total
Aug 23 - Aug 24
Total with taxes and fees
Paradise Point Resort & Spa
Manchester Grand Hyatt San Diego

Manchester Grand Hyatt San Diego

1 Market Pl San Diego CA
Fully refundableReserve now, pay when you stay
$235 nightly
$272 total
Sep 7 - Sep 8
Total with taxes and fees
9/10 Wonderful! (2,816 reviews)
"Exceptional stay. Clean, comfortable, well planned rooms. The only challenge was there was lots of construction - which is a positive because they're obviously keeping up on maintaining and upgrading the property, however the pool situation is a bit of cluster. There is a smaller pool open currently ..."

Reviewed on Aug 22, 2026

Manchester Grand Hyatt San Diego
See all 8,514 properties in Harbor Island
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.

Things to do

San Diego Padres Baseball Game at Petco Park

San Diego Padres Baseball Game at Petco Park

$44
per adult
San Diego Padres Baseball Game at Petco Park
San Diego: 3 Hour Whale Watching Cruise

San Diego: 3 Hour Whale Watch Cruise with Legacy Whale Watch

$34
per adult
94% of travellers recommend
San Diego: 3 Hour Whale Watch Cruise with Legacy Whale Watch
See all activities in San Diego

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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.