House holiday rentals in Lakeside

Wine Country Retreat - Tranquility Hottub/Views

Our famed Wine Country Retreat is back online! (LTR for the last year) Take the back roads scenic drive 50mins up the hill from San Diego and enjoy some much needed quiet and comfy tranquility. Right in the heart of San Diego Wine Country, it’s a rather well appointed place situated on 10 private acres that overlooks expansive green space. With few neighbors in any direction, you can either sleep with the windows open and wake early to roosters crowing, or close the windows and sleep til Noon!

San Diego Casita for 6 Morey de Prieto Surf Ranch

The Morey de Prieto Surf Ranch is truly awesome! Reserve your stay in this 2 Bed/1 Bath 650 sq. ft. casita for six. Home includes a kitchen with a GE electric cooktop, refrigerator, microwave/air fryer, rice cooker, mixer for drinks, sink with prep trays, Moen faucet fixtures, gorgeous shower, Krups coffee maker, 50" smart TV equipped with WiFi and NetFlix, mountain views, workspace and a sofa bed. Relax on the large 240 sq. ft. private deck featuring a fire pit, adirondack chairs and BBQ.

Sunnyside Resort Spa, Beach, Zoo, Arcade

SEND US A MESSAGE FOR SPECIAL OFFER! Imagine booking the most memorable experience with your party! Kick back and relax in a safe, stylish casita. Check in contactless and enjoy! Cozy, comfy, and a perfect base for exploring the city. Cook your own meal in the alluring kitchen or enjoy your meal at the cute dining area outside. Great for family's or trips with friends! The entire guest house is is 5 minutes from SDSU, 15 minutes from the beach and 15 minutes from downtown San Diego! Enjoy

The Glass House - A Nature Retreat

Enjoy a unique retreat; 180 degrees of views from inside the home. Nestled at the end of a private road, our place is nearby great hiking and countryside wineries. The Glass House provides a magical space and nature retreat where individuals, couples, families and friends can gather together to re-connect with nature, each other, and themselves. The breathtaking mountain top views, the huge deck, hot tub, fireplace, and the open concept living space is unbeatable for the perfect getaway.

XLarge Artist's Retreat w/private patio/parking

*Forget your worries in this beautiful 700sq/ft spacious and serene space. *Come soak up in the artsy feel of this newly renovated large guest suite, ideally located in the middle of town close to SDSU. Roll out of bed and Enjoy a cup of coffee in the private patio then explore ALL of the city’s top attractions a short drive away. This beautiful space is clean, crisp and fully decorated with great style uniquely curated with original art by one of SD’s most established artists. * Enjoy*

Cottage in the Garden! New! Modern!

COTTAGE IN THE GARDEN - New! Modern! Find beauty and serenity in this special guest house in one of San Diego's most desirable areas! Flowering bushes, plants, olive tree and fruit trees seen from all windows. All amenities: WiFi, Cable, serving dishes and tableware, full coffee bar, Ninja Blender, Flat screen TVs, 100% Egyptian Cotton Sheets or Boll and Branch Sheets (used by 3 Presidents), Japanese Toilette and more. 15 minutes to Downtown San Diego and 20 minutes to the beach!

SDCannaBnB #2 *420 *parking *dog-friendly *hot tub

Welcome to SDCannaBnB - San Diego's premier cannabis-friendly rental!   Our studio is newly remodeled with luxury ammenities.  We proudly cater to the cannabis community and non-users alike.   Our studio 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 studio is located in our quiet, fully fenced in backyard, close to San Diego's attractions

Peaceful Casita | Firepit • Near SDSU

Welcome to our cozy home, perfect for couples visiting the area. It's also a great spot for SDSU parents visiting their kids. Conveniently close to the campus but far enough to enjoy some peace and quiet. If you enjoy this listing, click the heart icon ❤ in the top-right corner to bookmark it for easy access! Minutes from key attractions: ★ 6 min to SDSU/Viejas Arena ★ 14 min to Balboa Park ★ 17 min to Downtown SD (Gaslamp) ★ 19 min to San Diego Zoo ★ 21 min to the Airport

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!

Lux Casita with Pickleball & Resort Amenities

Escape to this inviting Casita, where bright white walls and French doors fill each room with light and warmth. Thoughtfully furnished and full of charm, it offers a serene retreat with private resort-style amenities, including a tennis court, pool, and lush gardens. Step outside to hiking and biking trails, then return to cozy comfort. An optional second suite provides extra space for a relaxed, luxurious stay.

Suite Charles Way: A Cozy Fletcher Hills Studio

This newly remodeled spacious studio retreat features a private courtyard with barbecue, kitchenette, a brand-new California King bed, and a reclining love seat with charging ports. Enjoy a relaxed cabana vibe, a charming neighborhood and treetop views with easy access to all your favorite San Diego destinations. Within minutes from Grossmont Sharp Hospital, Grossmont Center, the trolley and Grossmont College.

Shadow House Mt. Helix

Shadow House is a 1-bedroom 1-bathroom sanctuary nestled on an exclusive road, yet, oh so close to the vibrant heart of San Diego. This charming retreat is your perfect base camp as it's only 15 minutes away from sun-kissed beaches or downtown. With boutique hotel amenities and lush outdoor spaces, we’ve practically invented outdoor comfort with a side of charm.