Guesthouse holiday rentals in Rancho 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!

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

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!

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.

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

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.

Enchanting private Mt Helix retreat close to SDSU

This quiet retreat (5 min. from the quaint main street of downtown La Mesa) used to be a doll workshop. Drink your morning ritual on a private deck amongst the trees. 15 min. from downtown and SD airport. 10 minutes from SDSU. 25 minutes to La Jolla/ beaches and most San Diego colleges and attractions like Birch Aquarium. 15 minutes from Balboa Park museums. Hike Mission trails-15 min. from trailheads. Take a walk up scenic Mt Helix and enjoy the vistas. Flora and fauna abound.

Vineyard & Winery Guest House

A hidden gem! Please send an inquiry if you are interested in staying with us. Get away and stay at the historic pioneer era Clark Ranch established in 1885. Our guest house sits above our winery tasting room and has its own private entrance and driveway. It's clean, cozy, and self-contained . Make it a weekend 'getaway' stay and sample our fine wines. There is a tower in the vineyard where you can enjoy a glass of wine and watch the sun set. Balcony overlooks Dulzura Creek.

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.

Beautiful Bright Mt. Helix Studio

This beautiful newly remodeled studio is in the heart of Mt Helix, a unique community in San Diego close to freeways, shopping, dining and more. Mt. Helix is called the lungs of San Diego because of it's lush surroundings and unique lots. We are surrounded by citrus orchards and are on a mountain giving you beautifully fantastic views. We are located in a private and quiet community just minutes from everything SD is so famous for.

Gorgeous Guest Home

NEWER 1 bed/1bath guest home located in beautiful Alpine. Includes a fully furnished living space, equipped kitchenette, Two Smart TVs, and WIFI. Extra large room with a super comfy Queen size bed. Full size bathroom with washer and dryer. Unit has A/C and heat. Parking is located on property. Wonderful neighbors and neighborhood. The entrance is completely private. Minutes to Viejas or the Sky Falconry. 🦅

Mt Helix Studio Loft with Mountain Views

Mountain Views: Freshly renovated, quiet and spacious studio loft in private neighborhood. Close to coffee shops, grocery stores, and quick access to major highways. 500 sqft open concept. Laundry, Fast Internet, Cable TV and streaming services. Additionally, if you like oranges and avocados we grow them on the property (Seasonal of course). We also have a chicken coop and fresh eggs on request.