Holiday rentals in Lakeside

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 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.

Cozy, secure, and quiet studio in Lakeside

Studio granny flat w/full bath. Large windows front & back giving great natural light. Located at the end of a dead-end private drive. The 420 sq ft space includes a 65" HD TV w/DirectTV service, high speed wireless & wired internet, kitchenette w/convection cook microwave, fridge/freezer, w/many other extras. Unit was recently remodeled with new furniture. 1 Queen bed, dbl recliners, & dinette. (Also, the picture of the front of our property is not accurate - Airbnb uses Google photos 😕)

The Outside Inn at The Tipsy Goat Ranch

Nestled near Iron Mountain, a popular hiking destination, and less than 16 miles from San Diego's pristine beaches and local attractions, enjoy all SD has to offer in a one-of-kind farm-to-beach experience. Immerse yourself in a rarely seen side of San Diego you won't find anywhere else. Based on adventure, wrapped in luxury, a deep love for nature and the creatures it inhabits (mini goats, alpacas, babydoll sheep, lop bunnies, and chickens), it'll be a tranquil getaway you'll never forget.

Lakeside Hilltop Retreat w/Amazing Pool & Spa

Beautiful private living, spectacular sunrises & mood-altering sunsets. This stunning home sits directly on top of a hill offering BREATHTAKING 300° VIEWS from floor to ceiling windows. Primary Suite offers a walk-in closet, sitting/office area and a spa-tacular bathroom with large steam shower and soak-in tub. The luxury kitchen features high end appliances, limestone flooring and leather finished granite counters! Outside you can enjoy the view from the sunken fire pit, pool, or hot tub.

Home at the Sanctuary

Welcome to our charming and eco-friendly tiny home located in between fruit orchards and an animal rescue in a serene rural setting. The perfect place to disconnect from the hustle and bustle of city life and immerse yourself in nature. Wake up to the sounds of birds chirping and the sight of our resident farm animals grazing in the pasture. Pick any of the ripe fruit from over 70 different fruit trees. Come experience sustainable living and succulent garden in our charming tiny home.

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

Hillside Retreat with Views

Escape to the mountains of San Diego and into a peaceful, well-furnished, private living space with plenty of room to spread out and enjoy the California lifestyle. Take in the panoramic views of El Capitan and the Cuyamaca mountain range as you enjoy your favorite beverage around the firepit. California awaits as you can wander east to the mountains and desert, or west to the beaches and shopping centers. Legoland, Seaworld, and the Sesame Place waterpark are all within a short drive.

Red Tail Ranch

A custom Log Cabin, perched on top of 15 acres located just outside of Ramona.You have an open-air experience while still having all necessary amenities to feel at home.Step outside and be surrounded by green, rolling hills and tall trees.Interact with animals, and enjoy the outdoors.Evenings you can retreat inside, sit by the cozy fireplace, play a game of pool, or go sit under the stars . Come fall in love with animals like mini highlands, alpaca, emu, mini donkeys, and more .

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

This is your perfect Guest House with a salt & heated pool & hot tub. We are located in a super quiet & very safe neighborhood in beautiful San Diego, 15 minutes drive to beaches, Downtown, La Jolla, Zoo, Stadiums, Sea World, Convention Center + more. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes and furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

Sycamore Creek cottage with Mountain View’s

Welcome to Sycamore Creek Cottage. A unique retreat in the foothills of San Diego county. A Delightfully decorated, fully furnished 2 room studio cottage . Sleeps 1 or 2 in a comfortable Queen bed. 1 full bathrooms, Fully fenced private patio, BBQ , firepit area with beautiful garden and mountain views. Pet friendly. close to Alpine & Sycuan Resort & golf. Ideal for business travelers, work remotely, visiting family or friends . I look forward to hosting you.