Harbor Island Vacations from $396
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Harbor Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Riviera Oaks Resort
San Diego Country Estates
Save 100% on your flight
Price was $635, price is now $396 per person
$396
per person
Jul 30 - Aug 4
found 12 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9.6/10 Exceptional! (1,005 reviews)
An oasis in the mountains! The scenery of the outdoors was great but the room was clean and very spacious! The staff are amazing and friendly! There was a power outage on our last night so we were given a refund for the inconvenience. We will definitely be back!
Reviewed on Jun 10, 2026
The Sofia Hotel
Downtown San Diego
Save 100% on your flight
Price was $1,419, price is now $742 per person
$742
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Dallas (DAL) to San Diego (SAN)
8.6/10 Excellent! (2,160 reviews)
Property was clean and the staff were very helpful.
Reviewed on Jun 11, 2026
Los Bungalows
Save 100% on your flight
Price was $1,485, price is now $815 per person
$815
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.2/10 Very Good! (536 reviews)
Honestly one of the best hotels I’ve stayed in the views the vibes overall very very peaceful place loved it
Reviewed on Jun 7, 2026
Hyatt Vacation Club at The Welk, San Diego Area
Lawrence Welk Resort Village
Save 100% on your flight
Price was $827, price is now $484 per person
$484
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.4/10 Very Good! (1,856 reviews)
We enjoyed our stay but there were a couple things I thought could be better. Our room had a strange musty smell to it. I tried to make coffee and realized that the coffee pot was cracked. Luckily, they have tea packets in the rooms so I had that instead. I wanted a Mountain View room but my balcony view was the back of the large kids slide instead with fencing. I also wish there were more places to eat around the grounds that had decent food. I didn’t want to have to leave the property but had to often.
Reviewed on Jun 12, 2026
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(8,598 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
The price is $234 total per night from Jul 1 to Jul 2
$234 total
per night
Jul 1 - Jul 2
8.4/10 Very Good! (3,536 reviews)
"Great place! Beautiful location, awesome food, amenities, staff, view, etc. Will definitely stay again."
Reviewed on Jun 11, 2026
Manchester Grand Hyatt San Diego
1 Market Pl San Diego CA
Fully refundableReserve now, pay when you stay
The price is $355 total per night from Jul 1 to Jul 2
$355 total
per night
Jul 1 - Jul 2
9/10 Wonderful! (2,807 reviews)
"The view from our room was amazing. Super clean & everyone was super nice, helpful & welcoming"
Reviewed on Jun 12, 2026
The Sofia Hotel
150 W Broadway San Diego CA
Fully refundableReserve now, pay when you stay
The price is $166 total per night from Jun 15 to Jun 16
$166 total
per night
Jun 15 - Jun 16
8.6/10 Excellent! (2,230 reviews)
"Great stay."
Reviewed on Jun 12, 2026
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.
Explore a world of travel with Expedia
- Flights to San Diego
- Flights from San Francisco (SFO) to San Diego (SAN)
- Flights from Seattle (SEA) to San Diego (SAN)
- Flights from Phoenix (PHX) to San Diego (SAN)
- Flights from New York (JFK) to San Diego (SAN)
- Flights from Las Vegas (LAS) to San Diego (SAN)
- Flights from Chicago (ORD) to San Diego (SAN)
- Flights from Dallas (DFW) to San Diego (SAN)
- Flights from San Jose (SJC) to San Diego (SAN)
- Flights from Los Angeles (LAX) to San Diego (SAN)
- Flights from Denver (DEN) to San Diego (SAN)
- Flights from San Diego Intl.
- Flights from Portland (PDX) to San Diego (SAN)
- Flights from Boston (BOS) to San Diego (SAN)
- Flights from Sacramento (SMF) to San Diego (SAN)
- Flights from Houston (IAH) to San Diego (SAN)
- Flights from Salt Lake City (SLC) to San Diego (SAN)
- Flights from Fresno (FAT) to San Diego (SAN)
- Flights from Minneapolis (MSP) to San Diego (SAN)
- Flights from Atlanta (ATL) to San Diego (SAN)
- Flights from Philadelphia (PHL) to San Diego (SAN)
- Flights from Detroit (DTW) to San Diego (SAN)
- Flights from Washington (IAD) to San Diego (SAN)
- Flights from Orlando (MCO) to San Diego (SAN)
- Flights from Honolulu (HNL) to San Diego (SAN)
- Flights from Oakland (OAK) to San Diego (SAN)
- Flights from Austin (AUS) to San Diego (SAN)
- Flights from Charlotte (CLT) to San Diego (SAN)
- Flights from Raleigh (RDU) to San Diego (SAN)
- Flights from Tucson (TUS) to San Diego (SAN)
- Flights from Boise (BOI) to San Diego (SAN)
- Flights from Reno (RNO) to San Diego (SAN)
- Flights from Baltimore (BWI) to San Diego (SAN)
- Flights from Cleveland (CLE) to San Diego (SAN)
- Flights from Kansas City (MCI) to San Diego (SAN)
- Flights from Pittsburgh (PIT) to San Diego (SAN)
- Flights from Tampa (TPA) to San Diego (SAN)
- Flights from Norfolk (ORF) to San Diego (SAN)
- Flights from St. Louis (STL) to San Diego (SAN)
- Flights from Nashville (BNA) to San Diego (SAN)
- Flights from Indianapolis (IND) to San Diego (SAN)
- Flights from Spokane (GEG) to San Diego (SAN)
- Flights from San Antonio (SAT) to San Diego (SAN)
- Flights from Cincinnati (CVG) to San Diego (SAN)
- Flights from Burbank (BUR) to San Diego (SAN)
- Flights from Milwaukee (MKE) to San Diego (SAN)
- Flights from Santa Rosa (STS) to San Diego (SAN)
- Flights from San Luis Obispo (SBP) to San Diego (SAN)
- Flights from Columbus (CMH) to San Diego (SAN)
- Flights from Jacksonville (JAX) to San Diego (SAN)
- Flights from Santa Barbara (SBA) to San Diego (SAN)
- Flights from Hartford (BDL) to San Diego (SAN)
- Flights from Miami (MIA) to San Diego (SAN)
- Flights from Monterey (MRY) to San Diego (SAN)
- Flights from Omaha (OMA) to San Diego (SAN)
- Flights from New Orleans (MSY) to San Diego (SAN)
- Flights from Fort Lauderdale (FLL) to San Diego (SAN)
- Flights from Richmond (RIC) to San Diego (SAN)
- Flights from Oklahoma City (OKC) to San Diego (SAN)
- Flights from Eugene (EUG) to San Diego (SAN)
- Flights from Memphis (MEM) to San Diego (SAN)
- Flights from El Paso (ELP) to San Diego (SAN)
- Flights from Albuquerque (ABQ) to San Diego (SAN)
- Flights from Washington (DCA) to San Diego (SAN)
- Flights from Palm Springs (PSP) to San Diego (SAN)
- Flights from Medford (MFR) to San Diego (SAN)
- Flights from Des Moines (DSM) to San Diego (SAN)
- Flights from Louisville (SDF) to San Diego (SAN)
- Flights from Pasco (PSC) to San Diego (SAN)
- Flights from Vancouver (YVR) to San Diego (SAN)
- Flights from Charleston (CHS) to San Diego (SAN)
- Flights from Tulsa (TUL) to San Diego (SAN)
- Flights from Syracuse (SYR) to San Diego (SAN)
- Flights from Grand Rapids (GRR) to San Diego (SAN)
- Flights from Colorado Springs (COS) to San Diego (SAN)
- Flights from Providence (PVD) to San Diego (SAN)
- Flights from Buffalo (BUF) to San Diego (SAN)
- Flights from Bakersfield (BFL) to San Diego (SAN)
- Flights from Redmond (RDM) to San Diego (SAN)
- Flights from Knoxville (TYS) to San Diego (SAN)
- Flights from Rochester (ROC) to San Diego (SAN)
- Flights from Manila (MNL) to San Diego (SAN)
- Flights from Bozeman (BZN) to San Diego (SAN)
- Flights from Long Beach (LGB) to San Diego (SAN)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.