Vacation rentals in Ramona

4.9 out of 5 average rating, 134 reviews

Two modern tiny cabins are nestled among tall evergreen trees, surrounded by the expansive vineyard landscape. Large picture windows allow for ample natural light, while Adirondack chairs are positioned outside for guest relaxation. The soft hues of twilight can be seen in the sky, enhancing the serene setting.

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, 378 reviews

An inviting open-concept living area showcases exposed wooden beams and a modern fan. A round dining table is set with place settings, while a comfortable sofa is positioned nearby. The kitchen features rustic cabinetry and ample natural light streaming in through large windows.

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!

4.92 out of 5 average rating, 357 reviews

The casita is viewed from a pool, reflecting its Spanish ranch style architecture and surrounding greenery. Warm evening lights adorn the exterior, enhancing the inviting appearance of the home, while the tranquil water surface captures the serene atmosphere.

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.

4.97 out of 5 average rating, 834 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.

5 out of 5 average rating, 102 reviews

A well-equipped kitchenette features open shelves displaying glassware and dishware. Dark cabinetry contrasts with white subway tile and a large window allows natural light. Modern appliances, including a coffee maker and microwave, are neatly arranged, offering convenience for meal preparation and dining.

Farm stay in Escondido

Peaceful new Tiny Home on farm, steps to wineries!

This new tiny home sits on a beautiful ranch in the middle of citrus and olive trees, with a vineyard as part of your view. It is near the Safari Park, wedding venues and is walking distance to 4 wineries! The property is gated so guests feel safe and sleep peacefully in the quiet of the country. You will love the fresh fruit, farm animals, and tranquility of the location - all while only being 4.5 miles off the freeway. This space is excellent for couples, friends and solo adventurers.

A small chick is being held gently in a person's hand, showcasing its fluffy yellow and black feathers. The chick's distinct crest and expressive eyes are prominently visible, suggesting a curious demeanor. The soft indoor lighting highlights the texture of the chick's feathers.

4.83 out of 5 average rating, 183 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.

Two Great Danes are positioned on a rocky surface, showcasing their distinct coats—one is black with brindle patterns, and the other is predominantly white with black spots. The backdrop features layered rock formations under a clear blue sky.

4.96 out of 5 average rating, 114 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, 133 reviews

Two highland cows are seen grazing near a pond, surrounded by lush green grass and trees. The cows display their distinctive long fur and horns in a serene outdoor setting, with a bright blue sky overhead reflecting the peaceful ambiance of the area.

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, 125 reviews

An outdoor seating area showcases a circular stone fire pit surrounded by dark wicker couches. String lights are hung overhead. Nearby, a dining table and chairs are positioned on the patio, while a rustic outdoor kitchen is visible against a backdrop of lush greenery.

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.

4.86 out of 5 average rating, 113 reviews

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!

4.92 out of 5 average rating, 192 reviews

A wooden picnic table is shaded by a large umbrella, positioned on a grassy area overlooking vineyards. A soft, warm light casts a gentle glow across the landscape, with hills visible in the background, creating a tranquil outdoor setting.

Tent in Ramona

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

4.84 out of 5 average rating, 122 reviews

A ping pong table is set outdoors, with a red paddle and ball placed on its surface. Lush greenery and distant mountains create a serene backdrop, while a pool area is visible in the distance, surrounded by seating and trees.

Hotel room in Ramona

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 with a variety of indoor and outdoor activities. 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 on-site amenities. Please read through full House Rules prior to booking.

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Popular amenities for Ramona vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Ramona

5 out of 5 average rating, 65 reviews

A cozy kitchen area is set against a rustic wooden wall featuring charming decorations. The kitchenette is equipped with modern appliances, complemented by a small rug on the floor. Stairs lead to the loft bedroom, and a clock adorns the wall beside the kitchen.

Tiny home in Ramona

Country cottage in Ramona near Potato Chip Rock

SkylerRating, 5 stars2 weeks ago

We absolutely loved the tiny barn! It was perfect for a couples getaway. Ty and Betsy were amazing hosts, and it was a beautiful spot to stay for a weekend. Lovely to bring our dog, they had dog beds and bowls available that made it super easy to have her. Beautiful yard to run around in. All of their recommendations were lovely, and they were so kind and communicative. Went above and beyond any hosts I’ve had before! The bathroom had several well stocked items that we really appreciated.

Guesthouse in Rancho Bernardo

A rustic sleeping area features a spacious bed with a patterned coverlet. Large windows provide natural light and views of the outdoors. A cozy armchair adds seating, while shelves display various decorative items. A mirror and soft lighting enhance the inviting ambiance.

4.91 out of 5 average rating, 763 reviews

Hilltop cabin retreat with lake & mountain views

EmilyRating, 5 stars1 week ago

We’re glad we booked this spot! It has a rare view and tasteful landscaping. The cabin was private and comfortable. Plenty of amenities, we especially enjoyed the pool! The hosts were extremely hospitable and generous with their personal space, and we would gladly book here again and again.

5 out of 5 average rating, 12 reviews

A gated entryway is framed by large boulders and surrounded by lush greenery. The gate is constructed of black metal, contrasting with the natural stone and earth tones of the pathway. Flashes of pink flowers add a touch of color to the serene landscape.

Guesthouse in Ramona

Woodson Hollow Bungalow

AdaRating, 5 stars1 month ago

Great stay. Enjoyed the BBQ and pool area for the weekend. Wonderful host. Calm and peaceful area. Very quiet and serene.

4.93 out of 5 average rating, 122 reviews

A wooden tiny cabin is nestled on a gravel area, surrounded by lush vegetation and palm trees. The warm wood tones of the cabin contrast with the natural landscape. A small porch is visible at the entrance, offering a glimpse of the cabin's exterior. Soft light is seen in the evening sky.

Tiny home in Ramona

Ramona Wine Country Cabins Near San Diego

TracieRating, 5 stars1 week ago

This was our 4th trip to the tiny home, and will gladly return in the future! We love the location… near a winery…the best view ever… pristine pool… and cozy loft. So many amazing restaurants and shops nearby. I love hitting up Squash blossom Trading Co. and Olive and Oak. Dining at Heroes (best wings hands down) and Marinade on Main. Becky is an amazing host and always super responsive and friendly.

A serene outdoor area features a curved swimming pool surrounded by lush palm trees and natural landscaping. The soft glow of sunset illuminates the scene, casting warm hues across the hillside, providing a tranquil environment for relaxation.

4.92 out of 5 average rating, 12 reviews

Spacious Retreat on 8 Acres with Pool/360 Views

ZaraRating, 5 stars6 months ago

My whole family gathered for Thanksgiving here. The house was even more beautiful than the pictures! It was like an oasis and we found everything one needed to feel right at home. We highly recommend this stay.

4.92 out of 5 average rating, 52 reviews

Several pigs are resting on the ground amidst a bed of straw. The animals are sprawled comfortably, showcasing their varying shades of black and pink. A gentle atmosphere is created by their relaxed postures, common to peaceful farm life.

Farm stay in Ramona

Farm Stay in Ramona

VirginiaRating, 5 stars1 week ago

Such a fun stay and experience. Fresh baked bread, adorable animals, and a SUPER host, we had a great time at Lana's.

Cabin in Palomar Mountain

The living area features wooden walls and a high ceiling, creating a warm ambiance. Two brown leather sofas are arranged around a stone fireplace, with natural light streaming through multiple windows. Cozy curtains frame the windows, and a vintage typewriter adds charm to the space.

5 out of 5 average rating, 161 reviews

The Wood Pile Inn getaway

KatherineRating, 5 stars4 days ago

I cannot say enough great things about the Woodpile Inn! Such a beautiful and cozy little cabin. The cabin was well stocked and had everything you could need for a little getaway. Sandra was an amazing host and was very responsive and helpful. Would absolutely recommend!