Vacation rentals in Ramona

4.8 out of 5 average rating, 120 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!

4.91 out of 5 average rating, 139 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.

4.95 out of 5 average rating, 382 reviews

A remodeled barn home is set amid a vibrant country landscape, featuring light-colored exterior walls and a welcoming porch. A garden area is visible beyond a rustic fence, complemented by surrounding trees and open skies, suggesting a serene outdoor space.

Farm stay in Ramona

Newly re-imagined space. Fresh & bright. Eggs too!

This space, formally a working barn, was remodeled into an amazing, one-bedroom home. Every detail was thoughtfully crafted to create an experience that caters to couples deserving of a destination escape in a country-like setting, yet close enough to all of San Diego's local attractions. We just completed a mini remodel with newly inspired spaces that include the living room with new furniture and a cozy reading nook and all new linens for both the bedroom and bathroom. Come see the changes!

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, 845 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.

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.

4.83 out of 5 average rating, 186 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.

A secluded hot tub is situated within a fenced yard, offering privacy and a serene space for relaxation. The area is bordered by wooden fencing, providing a cozy atmosphere. Nearby, the surrounding garden is visible, complementing the tranquil outdoor setting.

4.95 out of 5 average rating, 125 reviews

The little Farm stay

Escape to our charming two-bedroom farmhouse and experience the relaxing life outside the city. Enjoy watching our farm animals including Horses, Sheep, Pigs, Goats and two lovely Great Danes! Enjoy a complementary Farm Basket with your stay. Included in 2 night stays or more is a free farm tour, scheduled at booking. Sweet Heart Farms Sourdough is a popular local treat included in your farm basket, and available in our Farm Stand. This is not a wheel chair accessible property.

5 out of 5 average rating, 141 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, 130 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.

4.87 out of 5 average rating, 119 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

Join the royal court & stay in our 1975 Airstream Sovereign Land Yacht! Immerse yourself in a budding rescue ranch with pot belly pigs, horse, mini horse, mini donkey, alpacas, sheep, and tortoises, or take a romp on our 5 acres with lots of hidden gems to discover, or explore the many hiking trails nearby. You also have exclusive access to your own jacuzzi & 300sf deck! Our location is also unique because we are fully fenced in & an additional camper for more sleeping space!

5 out of 5 average rating, 100 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- End of Summer Sale

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!

4.96 out of 5 average rating, 148 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*

A spacious kitchen area features wooden cabinetry and a blue-tiled countertop that forms a kitchen island. The room is filled with natural light, showcasing stone accents and wooden beams on the ceiling. A dining area with wooden chairs is visible in the background.

5 out of 5 average rating, 112 reviews

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.

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Popular amenities for Ramona vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Ramona

Guesthouse in Rancho Bernardo

A scenic view captures lush hillsides and a calm lake under a clear sky, with a rainbow arching gracefully over the landscape. Green vegetation sprawls across the area, adding vibrancy to the tranquil scene.

4.91 out of 5 average rating, 782 reviews

Hilltop cabin retreat with lake & mountain views

4.98 out of 5 average rating, 48 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 home in Ramona

Private Getaway - Southwest Art Studio

Cabin in Palomar Mountain

A cozy living area features rich wooden beams and rustic stone walls. Two leather couches are arranged around a natural stone fireplace, which serves as a focal point. Warm light fixtures provide gentle illumination, enhancing the inviting ambiance of the space.

5 out of 5 average rating, 177 reviews

The Wood Pile Inn getaway

A three-story home is viewed from the pool's perspective, featuring a spacious porch and stone accents. Solar panels are visible on the roof. Surrounding landscaping includes lush greenery and well-kept plants, complementing the inviting blue of the pool's crystal-clear water.

4.67 out of 5 average rating, 12 reviews

Boulder Family Retreat! W/Pool!

5 out of 5 average rating, 38 reviews

A cozy exterior of a country home is presented, featuring a large arched window that allows natural light to fill the space. Wooden steps lead to a welcoming entrance. Decorative elements, such as vibrant artwork, add a touch of charm to the façade.

Tiny home in Ramona

Cozy Country Home

4.98 out of 5 average rating, 60 reviews

A charming exterior view of the main home is displayed, featuring a well-maintained entryway surrounded by various potted plants and decorative stones. The building is painted in light colors, with large windows letting in natural light, and a covered patio area is visible to the side.

Farm stay in Ramona

Cozy farmhouse near preserve

4.88 out of 5 average rating, 129 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 Davidson Glampling / Kids Play Area/Hot Tub

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.