Updated: April 2021
This post has been updated to include a roundup of my favorite boutique properties and vacation rentals in San Diego.
Renting an Airbnb is one of my favorite ways to see a place. Getting to see a neighborhood from a local’s perspective and finding places with serious design goals? That’s a win-win for me!
Whether you’re planning the perfect staycation, road tripping around California, or you just want to experience all the magic of San Diego, there are some pretty darn cool Airbnbs around the city.
Here are the coolest Airbnbs to stay at in San Diego!
Little Italy
Unique Urban Treehouse in Little Italy
BOOK HERE
Golden Hill
Cozy Craftsman in Historic Golden Hill
Take a step back in time in this 100-year-old craftsman home in Historic Golden Hill. The comfy retreat is fitted with a retro kitchen and darling built-in corner shelves.
The Airbnb is located right next to an iconic San Diego historic home and an architecturally eclectic neighborhood!
BOOK HERE
Little Italy
Industrial Light-Filled Loft
What a cool industrial vibe! Little Italy is known for its incredible restaurants and is a wonderful base to explore the rest of San Diego. Also, how epic are those windows?
BOOK HERE
South Park
Peaceful Casita in South Park
This studio casita has so much Southwestern-style charm. Wake up to the fountain sounds outside the door, and enjoy relaxing in the sunny courtyard surrounded by native plants.
BOOK HERE
French Tudor Studio
Located in the heart of Normal Heights, this newly-built studio is a private oasis tucked behind the main house. Gorgeous double glass doors lead out onto a paved patio—the ideal place to hang out with a cocktail under the twinkling lights!
BOOK HERE
Mission Hills
Cozy Studio with a Private Patio on a Canyon
If you’re a fan of French doors, you’ll love this place! A double pair of French doors lead directly from the European-style bedroom to a private patio. The ideal place for relaxing with a book and a cool beverage, or firing up the barbeque.
BOOK HERE
Gaslamp Quarter
Cool Loft Apartment in the Gaslamp
The area of Gaslamp is such a fun and hip place to hang out. This place is fitted with classic and sumptuous furnishings. I especially love the elegant tufted bed!
BOOK HERE
Kensington
Serene Garden Guesthouse
Central Kensington is full of boutique shops and local eateries—a lovely place to stay in San Diego! This secret garden house is filled with stylish and colorful décor and all the vibrant hues are so much fun. I’d suggest making a batch of margaritas and then hanging out in the garden!
BOOK HERE
Bankers Hill
Admire Harbor Views from the Porch of this Gem
This might be the cutest and most colorful casita. I adore the 1920s charm with all the Spanish-style accents.
The neighborhood is known for its eclectic vibe with some homes more than 100 years old. An easy walk to Balboa Park, Little Italy, or Downtown.
BOOK HERE
Hillcrest
Spanish Revival 1920s Bungalow
Nestled on an olive tree-shaded corner in the historic area of Hillcrest, this neighborhood is fantastic for walking around sidewalks filled with cafes, boutiques, and pubs. This 1924 Spanish Revival bungalow is fitted with modern touches.
BOOK HERE
This makes me want to visit San Diego again ASAP!
Aren’t they gorgeous? I love San Diego 🙂
We stayed in the Spanish Revival 1920s Bungalow a few years ago. Donna, the owner, is a wonderful woman and she really restored the character of the unique property. Loved the area. This property absolutely belongs on this list!
Thank you for sharing, Keely!