Pet-friendly holiday rentals in Old Town, San Diego

Ventana Vista | Ocean View | EV Charger | Designer

@ventanacollection This cliff-side Mission Hills home is a light filled and custom designed to elevate your future vacation rental expectations. Highlights: - Ocean views from every room - Outdoor patio w/propane firepit and Grill - Modern fully stocked open kitchen with high-end Thermador appliances - Theatre Quality 75" TV and speakers in the plush living room - Premium work from home sit/stand desk, monitor, computer, webcam, speaker set up - Helix and Sleep Night memory foam mattresses

Stylish Downtown Loft w/ Parking in Little Italy

Stylish Modern Loft In The Heart Of Little Italy. Immerse Yourself In San Diego's Trendiest Neighborhood With A Stay In This Elegant Loft. Featuring Exposed Brick, Tall Ceilings, A Cozy Loft Bed Accessed By A Ladder, And An Open Layout Adorned With Stunning Artwork, This Space Blends Charm And Sophistication. Enjoy Vibrant Culture, Renowned Dining, And Little Italy’s Lively Atmosphere—All Steps From Your Front Door. Includes 1 Free Onsite Parking Spot. 1 Dog Accepted With A $50 Pet Fee.

Modern Penthouse Loft w/ Balcony & Sunset Views

Penthouse loft in recently built ultra-modern building. Minimal and clean, but with all of the essentials. Gorgeous Sunset and neighborhood views from large private terrace. Paid reserved parking available. Conveniently located in the heart of Hillcrest, only 2 blocks to Whole Foods, Trader Joes, Ralphs grocery store, and many great restaurants, bars and boutique shops. Other nearby attractions include Balboa Park, Downtown San Diego, SeaWorld, The San Diego Zoo, and Mission Beach.

Canyon Views w/ Outdoor Seating & Parking

Prime location! Within walking distance to Trader Joe’s, Whole Foods, Ralph’s, cafes, gyms, amazing restaurants, great nightlife, and Sunday's Farmer's Market! This newly restored historic cottage is in the heart of Hillcrest, San Diego. Originally located in Balboa Park, it housed workers for the 1915 Panama–California Exposition. Perched on a canyon, the cottage blends modern amenities with farmhouse charm. Book now for a San Diego stay that fuses the past with modern comforts!

The California II- Luxury Mission Hills Hideaway

Escape to this luxurious Mission Hills home, a true sanctuary offering breathtaking panoramic views of San Diego. By day, marvel at the stunning vistas – the sparkling bay, the bustling airport, the Point Loma peninsula, and Coronado Island. The home itself is spacious and well-appointed, providing ample room for families or groups of friends. From the pristine beaches to the world-class museums and vibrant nightlife, your San Diego adventure truly begins here. 🏄

Om Home Beach Studio Bungalow - Walk to the Beach

The Om Home is a well-equipped private front studio in the Aloha Shores beach bungalow complex located in the heart of Ocean Beach! It has an awesome beachy ambiance & is just a short 5 minute walk to the beach and everything great OB has to offer! The Om Home has its own private entrance and deck with great views, full kitchen, and clean & comfy private bathroom. It’s the perfect spot for single travelers or couples looking for some R & R close to the beach!

The Cozy Craftsman

Escape to this serene, stylish retreat. Built in 1935, this Craftsman-style home exudes timeless San Diego charm. Perfectly situated in University Heights, bordering Hillcrest and North Park, you’ll be close to restaurants, cafés, grocery stores, public transportation, the San Diego Zoo, and Balboa Park. This 650 sq ft home has been renovated inside and out, and equipped with everything you need for a comfortable stay!

Hidden Casita with Private Deck & Patio

Charming Hidden Gem Studio in the Heart of Hillcrest Discover this hidden gem – a cozy, French-inspired studio casita with elegant furnishings and a private, furnished patio. Enjoy a fully equipped kitchen, a spacious open living and sleeping area, and an attached deck overlooking the tranquil canyon. Perfect for a peaceful retreat just steps from the vibrant Hillcrest scene.

Casa Nova - Central San Diego FREE parking

This gorgeously remodeled one bedroom home is conveniently located within historic University Heights. - a quick drive to the major attractions of San Diego and mere steps to plenty of shops and restaurants right outside your front door. Please also check our other listings if you can't find the dates you're looking for.