House holiday rentals in Little Italy

Admire Harbor Views from the Porch at a City Gem

Unwind in a cozy colorful casita in this light-filled 1920s Spanish bungalow decorated with Mexican folklorico. Take a walk into Little Italy for dinner. Or to a show at the Old Globe.What’s best, is how close you are to so much, all without needing a car. A very small single car garage is provided, think compact car. Street parking is free but challenging at times. The house is located directly below the incoming flight path. You are encouraged to read the reviews regarding this.Ideal for four.

Golden Hill Tree House

The Golden Hill Tree House is an urban oasis hiding in the branches of two mature trees in the heart of San Diego. While you enjoy elevated privacy you can also treat yourself to a soaker tub with double shower heads or settle down in a cozy reading nook to enjoy a good book! You'll also be walking distance to some amazing restaurants and super close to the best of San Diego, including downtown, the beach and the zoo! It's a perfect place to recharge after a long day of business or pleasure!

The Island View Penthouse

Enjoy staying in San Diego like a true native, our 3 bedroom, 3 bath, plus formal dining room, ocean view balcony, wood burning fireplace, and ample space to share with your entire group! Relax and enjoy our spacious front yard while dinning under the stars or sipping cocktails. All rooms feature luxury beds from Davenport Collection. We require minimum 2-night minimum per City code, and a $299 cleaning fee to support living wages in our area. Only guests with positive reviews please

*New* Renovated Historic Home in Little Italy

Step into the newly renovated Crowell Home, a historic 1888 gem in Little Italy. This luxury retreat blends timeless elegance with modern upgrades, offering an exclusive stay in San Diego’s trendiest neighborhood. ✨ Highlights: ✔ Landmark 1888 Crowell Home – Fully renovated. ✔ Prime Location – Steps from top dining & attractions. ✔ Modern Upgrades – Smart tech, WiFi, keyless entry. ✔ Outdoor Living – Private patio for relaxation. 🌟 Book now & experience the best of Little Italy!

Little Italy 2BR Loft Near Waterfront & Convention

Discover the heart of San Diego from our spacious loft in Little Italy, the culinary gem of downtown. Perfectly situated for both business and leisure travelers, you're steps away from the waterfront, convention center, and vibrant city life. Embrace the urban experience with convenience at your doorstep, including eclectic bars and restaurants. We provide a white noise machine and earplugs, though the lower floor offers a quieter retreat. Experience the best of city living!

Mid-Century Retreat Hillcrest, Parking, A/C

This 2nd floor retreat sits in a prime location of Hillcrest, a highly desirable area in San Diego. It is very bright, quiet, and private and sits directly behind our house(pictured) with no common walls. You are within walking distance to "The Heart of Hillcrest" where you will discover many fabulous restaurants, coffee and boutique shops, and so much more. We are a short Uber drive to downtown and everywhere else San Diego has to offer. We hope you stay with us soon!

The Pink Casita of Barrio Logan

This quaint home is central to everything San Diego. A stylish experience just minutes from Petco Park & Gaslamp! Barrio Logan, known for its art and culture, has tons of shops and restaurants just blocks away. Little Italy, Banker’s Hill, & Hillcrest are a quick Uber away! A quick 15 min drive from SAN. On site amenities include a private parking space, spacious balcony, dedicated workspace, TV & pool table! This carefully curated home will be yours away from home!

King Comfort in New Home + Projector

Luxury 2BR home in vibrant North Park, San Diego. Enjoy top-notch king/queen beds, a 150" projector, fresh coffee from our pour over, and sun-soaked patios. Walk to local attractions or reach others like Seaworld & the Zoo in <15 min. Benefit from free parking, ensuite bathrooms, a fully stocked large kitchen, and meticulous cleaning. Experience comfort, style, and convenience in our 1350+ sqft property. Your San Diego dream starts here!"

Walk to Bars, Restaurants 1 BD Hillcrest, Parking

This unique and luxurious house is located in Hillcrest, 1 block from University Avenue, within walking distance to some of San Diego’s finest restaurants, bars, and shopping. This location truly cannot be beat if you want to be close to it all in San Diego. You'll love the private outdoor space, and open concept home with designer finishes! Easy parking for one car. The perfect relaxing retreat in the city center of San Diego!