Family-friendly holiday rentals in El Cajon

Private 1 BR Paradise Retreat

Private, yet central. It is your exclusive paradise retreat to enjoy from your spacious 1 bedroom guest house located on the lower level of our home. Hang out in the expansive and private backyard with pool, different sitting areas and covered BBQ room. Or maybe a workout in the gym. Centrally located in the Village of La mesa. Just a 1/4 mile jaunt into the quaint village with its numerous assortments of dining options, stores and trolley station. Freeway close to beaches, downtown and airport

Family · Kitchen · Quiet

East Watch- a private getaway

East Watch is a 740 sq ft, 1 bedroom private retreat that provides the comforts and amenities of home with the style of a high-end hotel. All 5 to 15 min from shopping, downtown, and the beach. It's a short walk from Mt. Helix Park which offers a 360* view, weekday yoga, and stunning sunrises and sunsets. We have EV high speed car charging, a full kitchen with all appliances, workspace with dedicated fast WIFI, a spa shower, and super comfortable beds and pillows. Stay and let us charm you!

Indoor spaces · Family · Long stay

Modern mountain guest house. Incredible views

Neighboring San Diego, quaint country living with incredible views minutes from everything, breathtaking sunsets, 20 mins to beach, close by hiking trails, and only 3 minutes hop on the freeway. Full Kitchen, Laundry, and Living area and with beautiful furnishings, a perfect home away from home. Whether traveling for work or play we have had guests stay for a conference in San Diego or just to visit friends and hit the beach a few days, we look forward to you loving our home as much as we do.

Kitchen · Family · Air conditioning

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

Kitchen · Family · Check-in

Stylish Boho Studio | Walk to Cafes | Outdoor Livi

The studio is located within a quiet leafy neighborhood right in the heart of La Mesa giving you a great base to explore everything San Diego has to offer. Inside you will find a bright, sun-filled space with a chic kitchen, an open plan living/dining area with a comfortable sofa bed, a stylish queen bedroom and a modern, sparkling bathroom with a built in laundry. Stay a short 15 min walk to a shopping center nearby with cafes, restaurants and stores and an easy 15 min drive into Downtown.

Indoor spaces · Family · Access

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!

Indoor spaces · Kitchen · Outdoor spaces

Modern Cottage Getaway!

Welcome to your cozy getaway! This charming 1,000+ sq ft cottage offers an open-concept layout. Perfect for couples, small families, solo travelers, or anyone looking for a peaceful retreat. 🧺 Washer and dryer included for added convenience Located in a very quiet, residential neighborhood—ideal for those seeking rest and relaxation. 🚗 Parking: Guests have 1/2 reserved parking spot in the driveway. No Street Parking 🚭 No smoking 🐾 No pets or service animals due to health concerns

Family · Indoor spaces · Location

Farmhouse Cottage Retreat with Beautiful View’s

Welcome to the Farmhouse Cottage a serene countryside escape set on a former horse & cattle ranch, where wide open skies, rolling pastures, and quiet vintage luxury come together. Tucked away in a peaceful valley, this thoughtfully designed cottage invites you to slow down and reconnect-with nature, with loved ones, and with yourself. Once home to horses and grazing cattle, the land still carries that grounding , pastoral beauty. The Cottage sleeps 2 in a comfortable Queen bed.

Family · Indoor spaces · Walkability

Jamul Hacienda | Couples Retreat | Pool & Views!

The Casita retreat is a guesthouse situated among a private 20 acre oasis surrounded by majestic mountain views and a citrus grove 30-40 minutes from San Diego. The space is designed for nature enthusiasts to retreat from the daily hustle and bustle and find peace and slowness. Come take a pause, relax poolside, pick citrus (when in season), enjoy nearby trails, and wineries. The sunsets and starry skies are breathtaking. We hope you get to experience their magic for yourself.

Kitchen · Family · Bathroom

Quiet Country Home

Extremely clean home. Fenced private yard with Webber Genesis BBQ & Tables. Outdoor smoking. 25 minutes to beach or downtown. Rural area with animals “talking”. Horse visits and carrots included. Seasonal Fruits & Vegetables. 1st bedroom: king/full bath. 2nd bedroom: queen/work desk. 3rd bedroom: full & 2 twin trundle. All dishes/appliances. Crib & Highchair available Host lives in a separate complete 1 bedroom studio with a shared laundry room.

Family · Indoor spaces · Check-in

Valley View Garden Suite

Kick back, relax, and enjoy the view in this delightful, 1 bedroom w/ livingroom suite. 20 mins from beaches, downtown, Sea World, Zoo. 2 mi to Grossmont Hosp, 8 mi to SDSU, 3 mi to Gillespie Field The suite is attached on the side of a house. But it is completely separate and has its own private entrance. The back patio & side breezeway are just for you. The rest of the backyard is private for owners only. Free, reserved, off-street parking.

Kitchen · Indoor spaces · Bathroom

Beautiful 3,000 Sq Ft Tropical Oasis

Beautiful 4 Bedroom, 2 1/2 Bath Family Home Located in Tranquil Fletcher Hills. This 3,000 sq. ft. Home is Perfect for large families who wish to Relax in a Peaceful Setting. 24-hour self check-in keypad after 4pm and check-out at 11AM. Host does not allow parties/events. This is NOT a Party House! This home is located in a quiet residential neighborhood, Guests who do not respect this will be asked to leave.

Kitchen · Indoor spaces · Layout