Vacation rentals in Ramona

4.99 out of 5 average rating, 302 reviews

An aerial view captures the A-frame cabin surrounded by lush greenery. Warm light spills from large windows, illuminating the interior. The expansive deck is equipped with loungers, inviting seating areas, and a built-in BBQ, showcasing a welcoming outdoor space for relaxation.

Cabin in Julian

Welcome to your ideal retreat—a secluded mid-century modern A-Frame cabin nestled in serene Pine Hills, Julian. It's the perfect getaway for comfort and relaxation. ☞900ft² Deck // Dual propane firepits// propane BBQ ☞(6) Velux Skylights total: (5) incl blackout blinds & (2) open/close ☞75" and 55” LG Smart TVs w/Directv ☞Sony Soundbar & Sony PS-LX310BT Turntable. Classic and new LPs ☞Heated Bidet toilet seat ☞Binoculars: Celestial & Field both ☞Propane indoor heating stove ☞Tree house "vibe"

4.88 out of 5 average rating, 139 reviews

A vibrant camper is positioned on a grassy area with a sunset backdrop. A retractable awning provides shade over a picnic table. Nearby, outdoor seating and a BBQ grill are arranged, creating an inviting space for gatherings surrounded by nature.

Camper/RV in Ramona

Harley Glampling/Hot Tub/Kids Play/Privacy Fence

Disconnect from the world and enjoy a stay in this romantic and memorable 5 acre ranch located in San Diego's beautiful Ramona. This is a Harley-Davidson themed experience inside and out! This camper is equipped with everything you need to cook, BBQ, and have a great time surrounded by nature. Ramona also has many amazing winery's, hikes, Safari Park & horse trails. This stay includes Hot Tub, trampoline, kids playground, WIFI, AC/heat, BBQ grill, Solo Stove fire pit, picnic table, Smart TV's

4.79 out of 5 average rating, 131 reviews

A wooden deck features a soaking tub, surrounded by a potted plant. Large windows allow natural light into the cabin. The rustic landscape is visible in the background, providing a serene outdoor setting.

Cabin in Ramona

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!

4.9 out of 5 average rating, 154 reviews

A modern interior features a cozy loveseat and coffee table, complemented by a soft throw on the spacious bed. Large windows offer views of the vineyard, while an electric fireplace adds warmth. Soft natural light filters through, creating a serene environment.

Cabin in Ramona

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.

4.91 out of 5 average rating, 369 reviews

The casita is illuminated under a night sky, with the warm glow of string lights reflecting off the tranquil pool. The charming architecture features a second-floor window, while the inviting outdoor area showcases a blend of nature and modern design.

Guesthouse in Ramona

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.

An open-concept living area is highlighted by high ceilings and large windows, offering natural light. A modern kitchen features wood cabinets and a white island, while a dining table with turquoise chairs accommodates several guests. A cozy seating area is visible in the background.

4.97 out of 5 average rating, 867 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.

Cabin in Palomar Mountain

4.99 out of 5 average rating, 119 reviews

Cedar Crest

Cedar Crest is a nicely remodeled cabin while keeping its original charm. It is easy access. A few steps lead you to the deck in the middle of the trees... This cabin can sleep 2 people in a king bed and if you would like to bring your kids, the master bedroom has a full size futon. (Kids sleep free) For pet owner, the east side of the cabin has a fenced-in space. We recommend you do not let them be there unsupervised as a motivated mountain lion could jump the fence and arm your pet.

A rustic entrance to Elliott Pond Farm is framed by wooden fencing and trees providing shade. A sign adorned with a cow design and green grass welcomes guests, inviting them to explore the expansive farm area beyond. The dirt road extends into a serene landscape.

4.8 out of 5 average rating, 192 reviews

ENJOY A REAL FARM EXPERIENCE!

EXPERIENCE FARM LIFE! RESTORED OLD 3-BEDROOM 2-BATH FARMHOUSE ON 20 ACRES OF COWS, GOATS, CHICKENS, DUCKS! FEED THEM IF YOU LIKE. COLLECT EGGS FROM THE COOP AND PREPARE THEM IN THE OLD KITCHEN, RING THE TRIANGLE BELL AND DINE IN THE PASTURE! Stocked for breakfast, and since our farm is near town, a short drive for more groceries. Wi-fi. Netflix. Stay for a night or stay a month! Ramona offers antiquing, 3 excellent golf courses, 30 wineries, hiking, horseback riding, birdwatching.

5 out of 5 average rating, 154 reviews

A spacious log cabin features a green roof and an expansive porch. Surrounding the cabin are grazing animals, including mini highlands and alpacas. Rolling hills and trees provide a natural backdrop, with mountains visible in the distance under a cloudy sky.

Cabin in Ramona

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 .

4.96 out of 5 average rating, 138 reviews

A welcoming front porch with comfortable seating is situated beneath a covered roof. Hanging flower baskets add a touch of color, while the neatly manicured lawn frames the entrance. The exterior features a light blue siding with white trim, creating a calm atmosphere.

Guesthouse in Ramona

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.

5 out of 5 average rating, 111 reviews

A luxury RV is shown nestled among lush greenery, featuring a spacious wooden deck and a retractable awning. Colorful flowering plants are arranged in planters at the base, complementing the natural landscape. The sky above displays soft clouds drifting across a bright blue backdrop.

Camper/RV in Ramona

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!

4.95 out of 5 average rating, 153 reviews

The guest house exterior features textured stone-carved walls and a welcoming entrance. A sturdy staircase leads to the main door, while two vine sculptures adorn the sides of the entrance. The covered awning provides shade, complementing the surrounding landscaping.

Farm stay in Ramona

Casa de Piedra (Stone House) - 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*

Popular amenities for Ramona vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Ramona

5 out of 5 average rating, 41 reviews

The exterior of a stone studio is seen at dusk, featuring an arched entrance framed by natural stone walls. Steps lead to a small patio area, with expansive views of the surrounding landscape, including distant city lights and the twilight sky.

Cave in San Marcos

Casa Grotto, Romantic Stone Cottage w/ Ocean Views

5 out of 5 average rating, 95 reviews

A softly lit wooden pathway meanders through a lush garden, framed by greenery. Warm lights illuminate the edges, creating a serene ambiance as the path leads deeper into the vibrant landscape.

Home in La Mesa

Shadow House Mt. Helix

4.86 out of 5 average rating, 490 reviews

A comfortable living area features a high ceiling and large windows providing natural light and scenic views. A stone fireplace serves as a focal point, complemented by wooden furniture, a rocking chair, and a plush sofa. Warm, earthy tones create a cozy atmosphere.

Tiny homes in Ramona

Wind n Tail Ranch Tiny House Homestay

4.98 out of 5 average rating, 53 reviews

A cozy living area features a grey sofa adorned with decorative pillows. Natural light floods the space through large windows, offering views of green foliage outside. A wooden coffee table with a soft throw rests atop hardwood flooring, complemented by potted plants and rustic decor.

Tiny homes in Ramona

Private Getaway - Southwest Art Studio

A serene exterior view of the property showcases lush landscaping with various plants and rocks, framed by tall trees. The home is warmly lit from within, with a wooden deck inviting guests to enjoy the tranquil surroundings at dusk.

4.8 out of 5 average rating, 66 reviews

Peaceful and Gorgeous Oasis

5 out of 5 average rating, 13 reviews

A spacious living area is highlighted by a large stone fireplace, creating a central gathering place. Light wooden beams extend across the ceiling, with large windows offering natural light. A comfortable sectional sofa faces the fireplace, enhancing the inviting atmosphere of the space.

Home in Julian

Triple V Ranch (Veranda View of Volcan Mountain)

4.87 out of 5 average rating, 124 reviews

The Airstream is illuminated at night, resting on a wooden deck adorned with string lights. A cozy seating area with chairs is provided, framed by softly lit pathways. Surrounding trees create a serene ambiance, with a fenced area visible in the background.

Camper/RV in Ramona

Vintage Airstream w/ Farm Experience & Jacuzzi

The outdoor area features a spacious pool and hot tub, surrounded by lush greenery and palm trees. A cozy fire pit is positioned nearby, with comfortable seating areas scattered around. The house is illuminated by soft evening light, reflecting off the water's surface under a clear sky.