Smoking friendly vacation rentals in Downtown San Diego

Spacious apartment, old world charm

Our open-space apartment is full of charm and character. From the Spanish-tiled private entry to the footed tub shower, you will experience a unique feeling. Enjoy the nearby vibrant restaurant scene as well as the rooftop deck with its harbor view! The ceilings are low in a couple spots and could be a challenge for folks who are especially tall. My boyfriend is 6'4" and has learned to adapt! It may be something to consider. House noises travel in this old home, so it can be a factor for some.

Central San Diego! Your home away from home!

Guest house on property, outdoor smoking areas, and outdoor gym. Art, fun, movie-like experience with cable, over 30 movie channels, a DVD player, and a dining table for eating or working. Extensive and secure business network. Cleaned, sanitized, and checked after every visit. Full Kitchen, cooking utensils, Small 7.6 cu. ft. fridge, pots, pans, and baking dishes for longer stays. Top-notch air conditioning and heating, plus plenty of extra blankets for your comfort. Your home away from home.

Hilltop Hideaway w/Jacuzzi, King Bed, close2 DTown

Welcome to our charming home nestled in the heart of a vibrant neighborhood atop a scenic hill overlooking breathtaking views of the San Diego countryside! Just a quick 10-minute drive from downtown, the airport, Coronado Island and the convention center, your location here provides easy access to freeways, making travel a breeze! Relax in comfort and step outside to an inviting outdoor area, designed for you to immerse yourself in San Diego's spectacular sunsets and cool evening air.

SDCannaBnB #1 *420 *parking *dog-friendly *hot tub

Welcome to SDCannaBnB - San Diego's premier cannabis-friendly rental!   Our casita is newly remodeled with luxury ammenities.  We proudly cater to the cannabis community and non-users alike.   Our casita has HEPA air purifiers, is fully ventilated and receives deep cleanings between each guest.  This ensures that every guest checks into a clean, fresh-smelling place that feels like home.   Our casita is located in our quiet, fully fenced in backyard, close to San Diego's attractions

Guest Room with Beautiful Views

Welcome to our charming retreat nestled in San Diego. This private suite, attached to the main house, features its own bathroom, kitchenette, and a convenient private entrance with easy self-check-in. Just 10 minutes from Mission Beach, downtown San Diego, Balboa park, and SeaWorld. 5 min from Fashion Valley Mall, and only 2 minutes from the University of San Diego. You can either use the free parking space in front of the house or make use of the private driveway next to the house.

Upgraded Pt Loma Panoramic Views - 1 Bedroom Suite

Brand new full kitchen installed November 2025. Enjoy your home away from home and beautiful Pt Loma. With an expansive view of the gorgeous San Diego Bay & Shelter Island you can enjoy a comfortable space with luxury amenities. A spacious oasis to escape the hustle and bustle of the city, but close enough for a night out on the town. If you’d rather stay in and enjoy the views, relax on the patio, soak in the hot tub, or have a drink by the fire pit with your fur baby.

Romantic Bay View Suite • Rooftop deck & jacuzzi

Luxury Romantic Gateway Experience. Wake up to breathtaking views of the San Diego skyline and bay from your private rooftop deck. Relax in a stylish suite with a king-size adjustable bed, spa-style indoor Jacuzzi for two, and exclusive access to a rooftop fire pit and garden corner—perfect for a romantic night under the stars. Nestled in Point Loma, one of San Diego’s most exclusive and quiet neighborhoods, just minutes from Little Italy, the airport, and the beach.

Hot Tub Getaway by the Coast

Enjoy quality time with your entire family at this well-equipped home featuring a hot tub and tons of kids amenities! We cater to families. High-speed wifi, toys, and an outdoor wood-burning fire pit. Situated within walking distance to the Marina, downtown 3rd Ave, a 5 min drive to Sesame Place, a 15 min drive to the Zoo, downtown San Diego, liberty station, sea world, beaches, and more! This property is equipped with external security cameras for added safety.

Penthouse, Parking & Panoramic Views Little Italy

Walk to restaurants, bars, and Waterfront Park. Bask in stunning sunsets, balcony views, and refreshing bay breezes. My long-time residence embodies the neighborhood's charm, with the harbor nearby. Enjoy Saturday's local farmer's market just two blocks away. Experience the best of San Diego in the city's most walkable neighborhood! Happy to set you up at local restaurants and provide reservations as well. Will give you the best HH spots as well ;)

South Park Pet Friendly Bungalow

This 1940's 2 Bdrm 1 Bungalow is in a very quiet and secluded section of South Park. The yard was recently upgraded and is ideal for dogs and/or children. Entertaining is fine with us, friends, children and overall just enjoying life. In San Diego outside life is a given , please enjoy our patio, horse shoe pit, fire-pit, hammock and peacefulness of the yard. Please bring your family, pets and friends to enjoy some overdue relaxation!

OB Casita

Stay in a cozy Casita surrounded by a private garden. The inside space is petite, the yard is large. This in-law unit features a kitchenette, a private bathroom, a BBQ, and a fenced outdoor area perfect for pups! Sit under the avocado tree on the back deck and watch for the OB parrots. Or, take a short walk in this lively neighborhood to, beaches, dog beach, tennis courts, restaurants, bars, shopping, a playground, or a dog park.

Beach views for 2! Jacuzzi, fire pit

This mid-century modern jewel offers one of the best views in San Diego while still being walking distance (9 blocks) to the beach. You'll get a 1 bedroom with queen bed, full kitchen, living room with a futon couch (suitable for only one adult or two kids). I live upstairs and have a deck so you get your own private deck below me with a firepit and jacuzzi. Perfect place for a couple (or possibly a family with 2 small children).