Family-friendly holiday rentals in Ramona

The Wood Pile Inn getaway

Kick back and relax in this calm, stylish space. This historic cabin built in 1920 was recently refurbished to its old charm with some modern upgrades for your comfort. The original owner of the Cabin was an author named Catherine Woods. She wrote the very first book on the history of Palomar Mountain; Teepee to Telescope. You'll find a copy in the cabin for a good read.Lots of natural light make this little cabin feel spacious, the windows throughout the cabin offer a beautiful forest view.

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!

Wine Country Cabin Near San Diego - Private

Kick back and relax in this private cabin on 9 acre ranch. It’s a true get away. Come enjoy all the amenities including: Queen bed, full kitchen/bath, spa shower, 9 acres of private trails, intentional spaces, majestic views and a huge deck with a soaking tub to cool you in the summer (June - October). New A/C and heating. Enjoy a 5 minute walk to Milagro Winery and return to Littlepage for the amazing sunset. Or venture 15 minutes to the towns of Ramona, Julian or San Ysabel. Book Now!

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.

Glamping Getaway With Farm Animals

🤠 Adventure awaits on this ranch getaway, where the love of animals & nature is a must! Stroll the property and enjoy the sights and sounds of our friendly farm animals. Whether you’re seeking a quiet retreat, a family adventure, or a chance to reconnect w/ the outdoors, this ranch has something for everyone. We are a working ranch in collaboration w/ Right Layne Foundation, we work w/ the IDD community to offer an outdoor reset. Come stay, explore & fall in love w/ the magic of ranch life!

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.

Lazy Y Guest Ranch Jacuzzi, stars, peace and quiet

The jacuzzi, AC and heat are all in working order. A million stars and no cars at 4200’ elevation. Stay in a 25' renovated 1990's trailer with AC and a 280 sq ft covered deck with misters and fan, propane grill and PRIVATE JACUZZI! Dedicated WiFi bridge insures solid connectivity. Fresh air, no crowds, nice local trails. Local wineries and restaurants are tasty. Wifi is great. TV with Roku indoors; bluetooth speakers on the deck, and cows in the pasture. It’s a peaceful get-away!

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!