Holiday rentals with outdoor seating in Ramona

Luxury Julian Home w/ Cedar Tub, View, Horse Stall

Welcome to our stunning Julian retreat, Sierra Jean just 5 minutes from the famous Pie Town! This gorgeous home offers panoramic views from all rooms! Designed by a local interior designer, it's not your average Julian home. Enjoy Sonos sounds, a wood-burning fireplace & a fully stocked kitchen. Step onto the expansive deck with cantina doors for seamless indoor/outdoor living, complete with a fire pit & custom cedar soaking tub & 2 horse stalls. With 3 bedrooms 2 baths it's the perfect getaway!

VIEWS! Top of Mountain CABIN on 40 Acres Pets ok

Welcome to our “Above the Clouds” cabin, perched at 6,000 feet, the highest residential point in San Diego County. Take in breathtaking views of the surrounding mountains, Anza-Borrego State Park and city lights. Wake up to unforgettable sunrises and surround yourself with nature and tranquility. Lake Cuyamaca is just minutes away, offering hiking, fishing, birdwatching and stunning scenery. Enjoy a delicious lakeside meal, or take a short drive to visit the only Wolf Sanctuary in California.

Retreat:GameRoom/PuttGreen/Volleyball/Pool/HotTub

Located high on the mountain and surrounded by the best trails & wineries, this house offers something for everyone to enjoy their vacations at its best. See SD hot spots - Little Italy, Sea world, Balboa park, Lego land, Beaches, 30-40 mins away, SD safari zoo in 20 mins. Once you enter the house, you might not want to go out. A fully stocked kitchen, all kinds of games you can dream of from indoor to outdoor. When everyone is tired, just relax in the pool & enjoy sunset at the pool side bar.

Wine Country Retreat - Tranquility Hottub/Views

Our famed Wine Country Retreat is back online! (LTR for the last year) Take the back roads scenic drive 50mins up the hill from San Diego and enjoy some much needed quiet and comfy tranquility. Right in the heart of San Diego Wine Country, it’s a rather well appointed place situated on 10 private acres that overlooks expansive green space. With few neighbors in any direction, you can either sleep with the windows open and wake early to roosters crowing, or close the windows and sleep til Noon!

Mid-Century Modern A-Frame Secluded with Hot Tub

Secluded mid-century modern A-Frame cabin located in the Pine Hills community of historic Julian, CA. Built in 1969, the cabin completed a 2.5 year renovation in 2023 to meet modern tastes and amenities but keeps the original 60's groovy vibe. This unique family retreat offers a 900 sq ft deck, hot tub, firepits, and stunning views. Julian, a 1.5 hours drive east from San Diego, is a small town with big activities: hiking, biking, fishing, winery/breweries, winter sledding, apple pie eating.

Modern vineyard cabins in Ramona

Travino, a unique luxury vineyard glamping concept, is located in the beautiful Ramona Valley, just 40 min from San Diego! Named for winemaker’s favorite grapes Malbec and Syrah, our modern tiny cabins allow guests to wake up to beautiful views of the vineyard, offering the perfect escape from the city! Enjoy the opportunity to walk to the on-site vineyard tasting room or take a short drive to many other vineyards, great hiking trails, golfing, local restaurants, boutiques and shopping center.

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.

The Glass House - A Nature Retreat

Enjoy a unique retreat; 180 degrees of views from inside the home. Nestled at the end of a private road, our place is nearby great hiking and countryside wineries. The Glass House provides a magical space and nature retreat where individuals, couples, families and friends can gather together to re-connect with nature, each other, and themselves. The breathtaking mountain top views, the huge deck, hot tub, fireplace, and the open concept living space is unbeatable for the perfect getaway.

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 .

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.

Luxury RV- Edge of the Cleveland Nat’l Forest!

Scenic vistas and unique landscapes right outside the door! Nestled in the hills of San Diego, our luxury RV sits right on the edge of the Cleveland National Forest and is hiking distance from the famous Cedar Creek Falls. These hills host a wide variety of unique plant and animal life, like Laurel Sumacs, Yuccas, California Quail, and if you're lucky, you might even see a coyote or wild turkey. Book us today to experience a once in a lifetime opportunity!

The Dell, a relaxing country estate in Ramona.

The Dell in Ramona offers a 4 bedroom 2 1/2 bath single story house with a deck with two fire pits, a swim spa/jacuzzi and the most peaceful, serene place to enjoy a sunset. We are set up to handle your next event what ever it may be, We also offer the Pacific Room that's connected to the house and can sleep up to 6. Perfect for a girls weekend or couples that want to gather for wine tasting, hiking or visiting Antiques stores.