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Holiday rentals in Ramona

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Top-rated holiday rentals in Ramona

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Campervan/Motorhome in Ramona

4.9 out of 5 average rating, 144 reviews

Vintage Trailer Glamping in a Vineyard!

Ready to getaway? Need to get out of the house? Rosie is the perfect spot for you to escape and just breathe! Set at Hatfield Creek Winery in Ramona, San Diego's wine country, you can breathe in the country air and walk through the vineyard. Rosie has a full kitchen with sink, icebox, and a pink vintage stove. Enjoy some wine, the fabulous views, the peace and quiet, and the stars. Less than a 30-minute drive to historic Julian. Photoshoots must be approved in advance. Please notify the host.

Guest favourite

Guest house in Rancho Bernardo

4.92 out of 5 average rating, 662 reviews

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.

Guest favourite

Home in Alpine

4.99 out of 5 average rating, 158 reviews

Fully Fenced Alpine Property with Guest House

Our guest house is located in the back of our personal property & kept private by fencing. Our property is fully fenced & guests have access in & out by using a keypad. We have laundry facilities, a queen size bed in the master bedroom, a sofa sleeper in the living room/kitchen area and a private patio with bbq. We occupy the main home on the property. We have 2 dogs on the property so other animals are not recommended at this location. Children swing set/tramploine not included with Airbnb.

Guest house in Ramona

4.93 out of 5 average rating, 319 reviews

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.

Guest favourite

Guest house in Ramona

4.91 out of 5 average rating, 128 reviews

San Diego Country Retreat in Ramona Country

Private guest home minutes away from some of SD County's best hiking trails and wineries open year round, autumn weather now! Country serenity with beautiful sunrise views close to Mt Woodson Golf Course and the county's best hiking including: Mt. Woodson (home of San Diego's famous Potato Chip Rock), Iron Mountain, and Ramona Grassland's Preserve. Walk to wineries, scenic drive to Julian, The Laguna Mountains, The Anza-Borrego Desert State Park, casinos are nearby and downtown San Diego

Guest favourite

Home in Ramona

4.97 out of 5 average rating, 757 reviews

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.

Guest favourite

Guest house in Ramona

4.96 out of 5 average rating, 102 reviews

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.

Guest favourite

Tiny home in Ramona

4.93 out of 5 average rating, 119 reviews

Ramona Wine Country Cabins 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)Refrigerator, freezer, microwave and coffee pot. Only 45 minutes from downtown San Diego and within an hour from all areas of San Diego County.

Guest favourite

Farm stay in Ramona

4.95 out of 5 average rating, 359 reviews

Rustic, country farmstay. Fresh eggs & new pigs!

This space, formally a working barn, was remodeled into an amazing, one-bedroom home, meant to be enjoyed by couples and small families looking to make incredible memories. Every detail was thoughtfully crafted to create an experience that caters to those deserving of a destination escape in a country-like setting, yet close enough to all of San Diego's local attractions. We have goats, sheep, pigs, chickens, ducks, rabbits and barn kitties. We are a legit hobby farm.

Guest favourite

Tent in Ramona

4.91 out of 5 average rating, 151 reviews

Star Gazer Tent at Own Rooted Glamping

Own Rooted Glamping is located in the stunning Ballena Valley on the east side of Ramona. The glamp site overlooks Edwards Vineyard and is surrounded by the most stunning mountain views all around. Own Rooted Glamping is on 64 acres, which is private family owned, Please be respectful. The site is completely off-grid and 100% green natural energy. We are located near many attractions such as: Julian Historical Town: 17 min. Julian Pie Company: 10min Ramona: 15min

Guest favourite

Farm stay in Ramona

4.95 out of 5 average rating, 133 reviews

Casa de Piedra - Winery Guest House

This unique and upscale straw bale-constructed guest house on winery grounds is filled with delightful surprises, from the stone-carved walls to the beautiful artwork and furnishings. The fantastic view from the deck includes our vineyards and a view of Iron Mountain. Located in the heart of wine country, there are many wineries, including our own, that you can visit in Ramona. *Children under 18, pets, and parties not allowed*

Guest favourite

Tiny home in Ramona

4.93 out of 5 average rating, 338 reviews

Gnomewood: Rock Tiny House

Nestled in a canyon in the backcountry of San Diego County lies Gnome Wood. These 120 acres of oak woodland and mountain terrain provide habitat for multiple species... Enjoy a quiet nature retreat: a hike up the mountain, watch and hear the incredible bird activity from the front porch or read in the hammock. No visitors of guests are permitted. The Canyon Getaway, Hershey Bar, Bunk House, and others available for retreats...

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Popular amenities for Ramona holiday rentals

Free parking on premises

Air conditioning

Stay near Ramona's top sights

Ramona Cafe15 locals recommend

Stater Bros. Markets12 locals recommend

Kountry Kitchen6 locals recommend

Marinade on Main27 locals recommend

D'Carlos6 locals recommend

Mariscos del Mar de Cortez8 locals recommend

Other great holiday rentals in Ramona

Guest favourite

Farm stay in Escondido

5 out of 5 average rating, 63 reviews

Peaceful new Tiny Home on farm, steps to wineries!

Guest favourite

Campervan/Motorhome in Ramona

5 out of 5 average rating, 21 reviews

Soul Fungi Ramona Ranch RV

Guest favourite

Tiny home in Ramona

5 out of 5 average rating, 51 reviews

Country cottage in Ramona near Potato Chip Rock

Guest favourite

Campervan/Motorhome in Ramona

5 out of 5 average rating, 36 reviews

Dragon Fruit Farm Stay in Airstream

Guest favourite

Home in Ramona

5 out of 5 average rating, 98 reviews

The Dell, a relaxing country estate in Ramona.

Guest favourite

Tiny home in Ramona

4.97 out of 5 average rating, 36 reviews

Private Getaway - Southwest Art Studio

Guest favourite

Home in Ramona

4.95 out of 5 average rating, 86 reviews

The little Farm stay

Guest favourite

Farm stay in Ramona

4.94 out of 5 average rating, 34 reviews

George Gardens

Quick stats about holiday rentals in Ramona

Total rentals
60 properties
Nightly prices starting at
£31 before taxes and fees
Total number of reviews
2.6K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool

Destinations to explore