Holiday rentals with a pool in Ramona

Hilltop cabin retreat with lake & mountain views

Rustic hilltop cabin overlooking Lake Hodges. Surrounded by open canyons & mountains, you will feel like you're a million miles away from everything as you take in the views from the cabin, deck or the outside shower, swim in the saltwater pool, or relax by the fire bowl. A short walk to lake with boating, fishing & miles of hiking/mountain biking trails. Property offers swimming pool, fire bowl, and shaded arbor. SD Zoo Safari Park, wineries, breweries, & ocean beaches all within easy reach.

Secluded Casita in Wine Region

The Casita is a separate building next to our home. Its unique design with saltilo tile and natural stone kitchen gives it lots of character. You will enjoy a private bedroom and separate living space. Close to Orfila winery, and San Diego's incredible wine region. You will have a private patio with access from french doors in your unit. There is a bbq and pool in our shared back yard space, available for our guests only, upon request. This space is not offered for parties, or gatherings, sorry.

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!

French Garden Poolside Retreat -Wine & Safari Park

170+ Perfect 5.0 Reviews – Amazing views, peaceful and beautiful apartment on a French estate in San Diego Wine Country close to the Wild Animal Park. A perfect setting to celebrate a special occasion and create memories. Amazing sweeping views of the vinyards/mountains situated on the golf course with full access to the pool, spa, covered parking, EV chg. and private European garden park. Beautiful luxury apartment suite with a kitchen, sitting room, bathroom, steam shower/sauna and bedroom.

Gorgeous guesthouse with tranquility spa.

That privacy. That gorgeous two-story guesthouse nestled among 1.5 acres of tranquil gardens. That luxurious soaking tub for two. That cascading rain shower. That soft mood lighting. Those flickering candles. That indoor–outdoor spa experience. That rooftop lounging deck. That secret enchantment garden. Oh- we deserve this. Whether you're seeking a romantic getaway, a peaceful solo retreat, or a quiet space to recharge, this haven offers the perfect blend of comfort, privacy, and nature.

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.

Ramona Wine Country Cabin Near San Diego

This Tiny Cabin is located on beautiful 8 acres in Ramona Wine Country. Walking distance to Turtle Rock Ridge winery and many more nearby. 600 acre open space preserve next door with miles of trails. Enjoy a pool in the summertime. Forever views to enjoy from your private patio area. Comfy queen size bed in the loft (remote control stairs)Small Refrigerator, freezer, microwave and coffee pot. Only 55 minutes from downtown San Diego and within an hour from all areas of San Diego County.

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.

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.

One Bedroom Condo in San Diego Country Estates

San Diego Country Estates is nestled against the foothills near the quaint and historic towns of Ramona and Julian. Resort guests enjoy “The Good Life,” a perfect blend of active play and total relaxation. A resort fee of $27.00/night is included in the total price shown on Airbnb. This fee covers parking, Wi-Fi, and access to offsite pool, tennis, and pickleball. Please read through full House Rules prior to booking.