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

Cozy Spanish Casita w/ Mountain View in Ramona

Perfect getaway for wine lovers and hikers in this serene spanish ranch style casita with beautiful orchard & mountain views! Enjoy visiting Ramona's local wineries, hiking Mt. Woodson or Iron Mountain, swimming in the pool, stargazing, golfing, a day trip to Julian, or San Diego Wild Animal Park. The Casita has one private bedroom with a king bed and a cozy upstairs loft with a full bed located in a second room. Casita sits on top of a hill with the main house. Please read entire listing.

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.

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

Nestled in a quiet hillside canyon only 20 min from Downtown 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!

Hilltop Casita Mount Helix

View the sunrise and sunset from this panoramic hilltop casita. Enjoy a charming getaway with sweeping views of the mountains and valleys. Enjoy refreshments on private patio while taking in the sights of palm trees and endless hills. Located 15 miles from the beach and 20 minutes from many major San Diego attractions. Please note: we currently have an outdoor renovation project in process behind the casita. There may be days during your stay in which outdoor work is being performed.

Adorable Hawaiian themed Guest House

Enjoy the quaintness of country living just 35 miles from San Diego. Ramona is the heart of San Diego's wine country; home to many boutique winery’s and vineyards. Our guesthouse will provide the perfect space to unwind and relax after sightseeing, beaching, or visiting the world famous San Diego zoo. Guest home has one bedroom with king bed, separate great room/kitchenette w/hide-a bed and a couch. Fire pit, large grassy play area with zip-line and a pool to cool off in.

Fletcher Hills - modern 1 BR.Easy, no step access.

** 36 hours between check-ins. Thorough cleaning and sanitizing.. Four night minimum stay. Dogs ONLY are welcomed on a case by case basis. They must be house trained and are not permitted on any furniture. If you instant book, you must contact me about your pet within 24 hours. Smoking is permitted in the outside areas - patio, gazebo, yard. Easy freeway access helps any commute to downtown and area attractions. Having your own vehicle is the best way to get around..

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.

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 located just 20 min from downtown San Diego ✦Private Hot Soaking Tub under the stars ✦Panoramic City views ✦Custom outdoor movie theatre ✦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"!