Holiday houses in Rancho San Diego

4.96 out of 5 average rating, 84 reviews

A modern two-story guest house is set amidst lush natural surroundings, featuring a sloped roof and charming design. The property is accessed via a dirt pathway, with greenery and mountain views framing the scene, highlighting the tranquil rural setting.

Farm stay in El Cajon

Modern Farmhouse Hideaway near San Diego

Welcome to our guest house. Enjoy the peace and tranquility of this modern farmhouse sitting on the edge of nature. Hiking trails are nearby or just relax and enjoy the beautiful sunset on your private deck. This guest house is perfect for two adults who want to escape from the city. Relax in the newly renovated indoor space by enjoying a quiet dinner for two or a movie on the big screen. This can also be a winter escape for Snowbirds as we offer a long term rental discount (30d) James & Zdenka

A welcoming entrance features a textured walkway leading to a front door, framed by a wooden railing. Colorful flowers bloom along the sloped landscape, enhancing the natural appeal of the surroundings. Clear skies and distant homes provide a serene backdrop.

4.99 out of 5 average rating, 229 reviews

Modern mountain guest house. Incredible views

Neighboring San Diego, quaint country living with incredible views minutes from everything, breathtaking sunsets, 20 mins to beach, close by hiking trails, and only 3 minutes hop on the freeway. Full Kitchen, Laundry, and Living area and with beautiful furnishings, a perfect home away from home. Whether traveling for work or play we have had guests stay for a conference in San Diego or just to visit friends and hit the beach a few days, we look forward to you loving our home as much as we do.

A serene courtyard features smooth stones and desert landscaping, accented by palm trees and a vibrant green plant. The rustic entryway, marked by wooden doors, invites guests into the home while sunlight filters through the foliage above.

4.84 out of 5 average rating, 25 reviews

Weekend at Berny's

This 4 bdr, 5 bed home captures the essence of a SoCal lifestyle, blending modern amenities w/ family-friendly charm. The home is tastefully decorated to promote relaxation & togetherness. The loft area, transformed into a state-of-the-art gym, invites you to keep up w/ your fitness routine while enjoying views of the garden. Enjoy the gleaming pool perfect for morning laps or lazy afternoon floats. The well-appointed BBQ area & cozy fire pit set the stage for memorable evenings under the stars

Apartment in Rancho San Diego

A bright kitchen and living area features wooden cabinets and a small dining table with red chairs. A smart TV is mounted on the wall, and a light sofa sits beside a wooden coffee table. Sunlight filters through sliding glass doors, enhancing the space.

Quaint Apt with International decor

Minutes from all San Diego has to offer, this lovely 600 sq. ft. apt is newly redecorated, secluded, bright, with a skylight, 2 sliding glass doors, large private patio & designed with mementos and photos from your hosts travels around the world! Fully equipped kitchen & full bath. Shopping, dining, & attractions located within a 5 to 30 minute drive. Your hosts, Janet and Bill, are on site for support and to make your stay a great experience, but won’t initiate interaction. Welcome!

4.94 out of 5 average rating, 72 reviews

A spacious outdoor area showcases a sparkling pool and a heated spa, both surrounded by palm trees and vibrant greenery. The patio features lounge seating, and a wooden deck extends toward the pool, inviting relaxation in the warm sun.

5.0 out of 5 average rating, 66 reviews

*San Diego Oasis* Sunrise Views Pool Spa Sleeps 13

Enjoy your next San Diego getaway at our spacious estate in prestigious Fuerte Hills, Uninc. El Cajon. The property accommodates 13 people, both children and adults are welcome. The private backyard entertainment spaces are surrounded by mountain views. Amenities abound with a high-end chef's kitchen. Gas BBQ +Traeger smoker. Spacious indoor and outdoor living areas, game room, smart TV’s, & fast Wi-Fi. Relax in the heated spa or splash in the sparkling pool & enjoy the family by the fire pit.

4.85 out of 5 average rating, 424 reviews

Home in La Mesa

Cozy 4bd Family Home near all SD Attractions!

This sunny, 4bd home located on a private cul de sac in Mount Helix. Perfect for both family vacations & business trips. Conveniently situated near freeways & grocery stores. It’s comfortably furnished with a fully equipped kitchen. We have new beach chairs towels & toys! Pac-n-play available, fast Wi-Fi and smart TVs. The home features a quiet, private fenced backyard, BBQ, & covered patio. There’s plenty of room for kids to play! Please note that parties and events are not allowed.

A serene pool area is framed by vibrant green foliage and terracotta walls, with lounge chairs positioned nearby. Majestic mountains rise in the background under a clear blue sky. A shaded picnic table is visible, inviting relaxation in a tranquil outdoor setting.

4.98 out of 5 average rating, 120 reviews

Jamul Hacienda | Couples Retreat | Pool & Views!

The Casita retreat is a guesthouse situated among a private 20 acre oasis surrounded by majestic mountain views and a citrus grove 30-40 minutes from San Diego. The space is designed for nature enthusiasts to retreat from the daily hustle and bustle and find peace and slowness. Come take a pause, relax poolside, pick citrus (when in season), enjoy nearby trails, and wineries. The sunsets and starry skies are breathtaking. We hope you get to experience their magic for yourself.

4.97 out of 5 average rating, 116 reviews

Villa in Jamul

@ Paradise villa, Top view, 4600sqrt on 10 acres

TOT #COSD-00749 Experience stunning 360-degree views from every corner of this spacious villa, which spans 4,600 square feet on 10-acre lot. This is the perfect place for family gatherings and celebrations. The house features five oversized bedrooms and four bathrooms. There is parking +25 cars. Max 50 guests. Enjoy a massive pool, deck, golf, chess, pool table, foosball, ping pong, Nintendo game, and screen projector. This truly one-of-a-kind property is not to be missed!

5.0 out of 5 average rating, 19 reviews

Jamul Luxurious Estate-Playground-Private-Spacious

Bring the whole family to this serene estate with endless room for fun. 🔸Full playground 🔸Pool table and indoor/outdoor speaker system 🔸Outdoor dining and endless views 🔸Incredible design and custom designed architecture 🔸2.5 gated and private acres 🔸Chef kitchen with fully loaded amenities and coffee bar 🔸30 minutes from San Diego's beaches, zoo, and downtown attractions 🔸Perfect for families, couples, golfers, and more seeking an elevated San Diego experience.

An open-concept living area is highlighted by vaulted ceilings and natural light from large windows. A spacious L-shaped sofa is positioned around a coffee table, facing a wall-mounted TV above a modern fireplace. Nearby, a dining area can be seen through an archway.

4.99 out of 5 average rating, 131 reviews

Spacious & Fun | 5br, 4.5ba | Hot Tub | Views

Experience sunny San Diego from this 5 bedroom, 4.5 bathroom foothill home. Wake up to panoramic views of the surrounding hillsides and gather in the spacious living and dining rooms. The home is conveniently located just 15-20 minutes from San Diego's famous beaches and top attractions. After a day of exploration, unwind in the backyard area featuring a hot tub, fire pit, pool table, and life-sized chessboard.

4.96 out of 5 average rating, 393 reviews

Private Vineyard Estate w/ Guest House & Hot Tub

Enjoy a quiet oasis where family and friends can relax and play within the privacy of a gated 2-acre vineyard with endless on-site activities. The home layout is ideal for families or friends, with 4 bedrooms in the main house and the convenience and privacy of a separate Guest House (included in rental) with a full kitchen, living room, bathroom and bedroom. **Please no extra guests, events or gatherings**

An open concept studio loft is depicted, featuring a light-filled living space. A comfortable sofa is positioned in the foreground, with a sliding barn door leading to a kitchenette and laundry area. Natural light streams through a large window, brightening the entire room.

4.97 out of 5 average rating, 220 reviews

Mt Helix Studio Loft with Mountain Views

Mountain Views: Freshly renovated, quiet and spacious studio loft in private neighborhood. Close to coffee shops, grocery stores, and quick access to major highways. 500 sqft open concept. Laundry, Fast Internet, Cable TV and streaming services. Additionally, if you like oranges and avocados we grow them on the property (Seasonal of course). We also have a chicken coop and fresh eggs on request.

Popular amenities for Rancho San Diego holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Rancho San Diego

Superhost

A spacious pool area is framed by a smooth, curved edge with clear turquoise water. Lush palm trees and colorful potted plants surround the pool, providing a vibrant outdoor setting, enhanced by natural sunlight filtering through the clouds.

Home in Rancho San Diego

Palmeras House: Pool + outdoor BBQ

4.76 out of 5 average rating, 82 reviews

4.94 out of 5 average rating, 50 reviews

Private Mountaintop Retreat

5.0 out of 5 average rating, 84 reviews

The spacious kitchen and living area features modern appliances, including a stove and refrigerator. A comfortable sectional sofa is situated near a coffee table, with two floral wall art pieces enhancing the decor. A dining table and chairs are positioned to the side, under natural light from the large window.

Guesthouse in La Mesa

Secluded, tranquil guesthouse in plumeria paradise

Superhost

4.85 out of 5 average rating, 89 reviews

Nice Studio for 2-4 People in San Diego

An outdoor balcony features a gas fire pit at its center, surrounded by stylish seating arrangements. A large umbrella provides shade, while vibrant plants add a touch of greenery. The sky is painted with soft hues of pink and purple, creating a serene atmosphere.

4.97 out of 5 average rating, 65 reviews

The Coral House - Gorgeous Apt.+Grill+Fire pit +EV

Superhost

Home in Spring Valley

Family Coastal Farmhouse w/ Views

4.92 out of 5 average rating, 96 reviews

The exterior of a two-story house showcases a modern design with a neutral color palette and stone accents. A spacious balcony extends from the upper level, surrounded by trees. The driveway leads to the main entrance, offering a welcoming aspect in a serene setting.

5.0 out of 5 average rating, 20 reviews

The Bunny’s Burrow | Jamul Mountain Getaway