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The Coolest Airbnbs in San Diego

Coolest Airbnbs in San Diego

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

Want to hang out in Little Italy? This “urban treehouse” offers 180-degree city and bay views from this industrial penthouse in a super cool building designed by a local architect.
I’m a big fan of the succulent-filled private patio, and the wall featuring all the vibrant spirits and liquors!

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

I’d love to hear about your favorite Airbnbs in the San Diego area! Let me know in the comments below!

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    1. Natasha Ntone

      This makes me want to visit San Diego again ASAP!

      September 4, 2020 at 1:54 am · Reply
      • The Blonde Abroad

        Aren’t they gorgeous? I love San Diego 🙂

        September 6, 2020 at 6:28 pm · Reply
    2. Keely

      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!

      November 9, 2020 at 4:05 pm · Reply
      • The Blonde Abroad

        Thank you for sharing, Keely!

        November 13, 2020 at 10:22 am · Reply

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    Four Seasons is known for their luxury and incredible service, but they really kick things up a notch for families here:

    🧸 The Mystery Toy Closet: As part of the VIK experience (aka Very Important Kid Experience), guests are given a large golden key that grants access to an AMAZING toy closet behind the front desk. Filled with trinkets like rubber ducks, slinkys, coloring books, and–Ollie’s favorite–wiggly frogs, this was SUCH an amazing and one-of-a-kind treat to experience.

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    🦞 The Food: Whether it’s in-room dining you’re after, quaint tea service in-between sight-seeing, or you want to experience New England’s famous seafood, Four Seasons treats your tastebuds with exquisite table-side service at their restaurant, Coterie.

    This was truly such a luxurious end to our trip, I wish we could have extended it just so we could enjoy more time at this fantastic property.

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    The most luxurious family-friendly stay at Four Seasons Boston @fsboston 🏢 •••••••••••••••••••••••••••••••••••••• If you’ve been following along, you know we recently took a trip through New England for leaf-peeing and sightseeing amidst the crisp, Autumn foliage. We concluded our 10-day roadtrip at the amazing Four Seasons property in the historic city of Boston, Massachusetts. Four Seasons is known for their luxury and incredible service, but they really kick things up a notch for families here: 🧸 The Mystery Toy Closet: As part of the VIK experience (aka Very Important Kid Experience), guests are given a large golden key that grants access to an AMAZING toy closet behind the front desk. Filled with trinkets like rubber ducks, slinkys, coloring books, and–Ollie’s favorite–wiggly frogs, this was SUCH an amazing and one-of-a-kind treat to experience. 🍭 The Vault: One of the newer features to the Four Seasons Boston: a small room on each guest floor filled with complimentary snacks, candy, and beverages to grab-and-go! 🛎️ Amenities: Once again, Four Seasons has outdone itself with its amazing service. This city retreat offers a complimentary coffee bar for guests (and hot chocolate for the little ones), 24-hour gym, a pool with a fantastic view, a world-class spa, and even a morning run club to get your Boston marathon fix in! 🦞 The Food: Whether it’s in-room dining you’re after, quaint tea service in-between sight-seeing, or you want to experience New England’s famous seafood, Four Seasons treats your tastebuds with exquisite table-side service at their restaurant, Coterie. This was truly such a luxurious end to our trip, I wish we could have extended it just so we could enjoy more time at this fantastic property. A huge thank you to @fsboston for hosting us on our dream trip to New England and concluding our stay with memories that will last a LIFETIME! •••••••••••••••••••••••••••••••••••••• #fourseasons #boston #familytravel #newengland

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    ✨ Escape to luxury without the overnight price tag! ✨ Did you know you can enjoy five-star resort amenities without staying the night? Thanks to @ResortPass, I booked a dreamy daycation at a local luxury hotel in San Diego. From poolside lounging to world-class spa facilities (hello, dry sauna and cold plunge 🧖‍♀️), I had a self-care day to remember—for a fraction of the price. Whether you’re upgrading a layover, planning a day out on your next trip, or just treating yourself, ResortPass makes it easy to get more vacation for less starting at just $10/person. Use my code RPKIKI50 for $50 off $200+ before 12/3! #ad

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    440 11
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    BLACK FRIDAY DEAL! You can save 30% or MORE on select hotels—read below! #ExpediaAmbassador 🚨 •••••••••••••••••••••••••••••••••••••••••••• @Expedia is having a crazy Black Friday sale you HAVE to jump on! If you sign up for One Key, you can save 30% or MORE on select hotels when you book from November 22nd to December 4, 2024 (so long as you travel before December 15, 2025).” You know I LOVE a good hotel and have been using Expedia for years to get great deals on some of the best luxury stays around the world. New Year’s is just around the corner, and it’s the perfect time to start planning your dream trip — Expedia’s black Friday sale includes hotels all over the world. For some of my favorite properties, check out the link in my bio for a collection of my bucket list luxury properties that are currently on sale! •••••••••••••••••••••••••••••••••••••••••••• If you’re planning an epic trip in 2025, do not walk, FLY to this Black Friday Sale. Disclaimer: Book by 12/4/24 11:59pm in hotel property local time. Stay between 11/21-12/15/25. Prices are available to Expedia app users and One Key members. Limited availability, blackout periods may apply.
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