Guest house holiday rentals in East County, San Diego

Anna's Historic Stone Cottage w/panoramic View!

Welcome to Anna's Historic Stone Cottage! The 110 year old cottage has been transformed into the perfect combination of romantic and rustic for a dream-worthy getaway. The 280sq ft cottage features stunning, panoramic views of the San Diego skyline while offering rooftop seating for sunrise and sunset viewing. The Cottage is conveniently located 20 minutes from the world famous San Diego zoo and most other must-see, tourist spots. Amenities for special occasions offered too. Check out our menu!

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.

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!

San Diego Mountain Retreat

3 bedroom 1 bathroom loft (2 separate sides) open concept guest house. Very peaceful East San Diego getaway. Enjoy beautiful ocean and Mountain Views during the day then relax in the jacuzzi with breath taking sunsets and the city lights at night. Best views in San Diego! Only 25 minutes from the SD airport and beaches. Minutes away from 2 local wineries and casinos. House sleeps 6 but you can invite guests up for the day for a fee. Event prices will be discussed per event. We live in main home

Loft Cabin•SoakTub•FirePit• Cinema•View+Zoo add-on

Tucked into a quiet hillside canyon above the city, this very private, nature-immersed retreat is just a short drive outside of downtown San Diego. Features include: ✦Private Hot Soaking Tub under the stars ✦Panoramic City views ✦Custom outdoor theatre ✦Queen bed - always white sheets ✦Fast Wi-Fi ✦New quiet AC/Heat ✦Gated, off street prkg Relax on your private patio, unwind in the outdoor hot soaking tub or rain shower and end the night with a movie at your very own "Cinema Under the Stars"!

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.

Mountain top view getaway loft

This loft is completely sound proof! VIEWS, VIEWS, VIEWS!! Do not miss this stunning contemporary loft, located in the highly desired Mt. Helix community. The guest house faces west, giving you phenomenal 270-degree views of the ocean, Downtown, Point Loma, Coronado islands, Coronado bridge, and more! Designed and built by an acclaimed San Diego home designer, this property was featured in Dream Homes Magazine and is well known for its incredible design and construction.

Back Country Retreat

Back Country Retreat is nestled under oak trees and surrounded by a natural rock setting. You will be greeted with several flower gardens. The retreat has a lovely flagstone patio with outdoor gas firepit and custom cedar bar. Pine Valley has clear night skies with no light pollution. You will feel right at home in this quiet neighborhood with access to the Cleveland National Forest for hiking, biking or birding. Owners live on the same property, so you may see them.

Airstream•Sauna•SoakTub• Views•Firepit+Zoo add-on

Nestled in a quiet hillside canyon above San Diego, this one of a kind glamping retreat offers: ✦Private Hot Soaking Tub under the stars ✦Panoramic city/sunset views ✦Custom wood-fired sauna ✦Golf chipping tee ✦Fast Wi-Fi ✦AC & Heat ✦Gated, off street parking Cozy up by the fire as the city sparkles below or try your swing at the golf tee. Reconnect & recharge in your own outdoor hot soaking tub, rain shower & wood-fired sauna - the perfect retreat for nature lovers!

Cool Julian Mountain Nights • Firepit + Stars

🏡 Oak Perch Cottage is a warm, family-friendly Julian retreat designed for easy, relaxing stays. Sleeps 4 adults plus kids, with queen beds, cozy fireplace, private deck, fast WiFi & a fully stocked kitchen. Thoughtful kid amenities include a Pack-n-Play, baby gates, toys & books. 🍼🌿 Outside, enjoy a firepit, BBQ & a large fully enclosed yard and deck—great for kids and a dog alike. Minutes to downtown Julian, orchards & hiking. 🍎🌲

Private Julian Cottage• Sunrises•Starry Skies

Experience all four seasons from this peaceful hillside guesthouse, where expansive views and quiet mornings set the pace. Sip your coffee on the private redwood deck, enjoy meals outdoors, and unwind in the rocking chairs as the sun rises and sets over the hills. This cozy retreat is designed for rest, reflection, and simple moments that linger long after your stay. Designed for two adults only or solo travelers.

La Cabana

Perfect getaway for the wandering individual, couple, or young family. This rustic casita is surrounded by beautiful mountain and ocean views! Enjoy swimming in the pool, stargazing, lounging, or casual day trips around San Diego (All the amenities are shared with the main house) . The casita has one queen bed and a sofa bed, small kitchenette. Plenty of parking in driveway. Please read entire listing for details.