Holiday houses in Rancho San Diego

Guesthouse in Lake Murray

The poolside area features a well-maintained saltwater pool reflecting the colors of the sunset. Comfortable seating arrangements, including lounge chairs and a cozy fire pit, are visible. Large umbrellas provide shade, and lush greenery adds to the serene ambiance.

4.97 out of 5 average rating, 153 reviews

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

Welcome to your personal resort! This is the perfect Guest House with a salt & heated pool + hot tub. Located in a super quiet & very safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

4.99 out of 5 average rating, 216 reviews

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.

Guesthouse in El Cajon

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 bright living area is visible, featuring a mix of modern furnishings including a cozy sofa, a smart TV, and a circular dining table with wooden chairs. Large windows allow natural light to fill the space, highlighting the warm wooden flooring and inviting decor.

4.97 out of 5 average rating, 111 reviews

East Watch- a private getaway

East Watch is a 740 sq ft, 1 bedroom private retreat that provides the comforts and amenities of home with the style of a high-end hotel. All 5 to 15 min from shopping, downtown, and the beach. It's a short walk from Mt. Helix Park which offers a 360* view, weekday yoga, and stunning sunrises and sunsets. We have EV high speed car charging, a full kitchen with all appliances, workspace with dedicated fast WIFI, a spa shower, and super comfortable beds and pillows. Stay and let us charm you!

4.98 out of 5 average rating, 105 reviews

The vibrant sunset sky is filled with hues of pink, orange, and purple, reflecting beautifully in the calm water of the pool. Palm trees stand in silhouette, framing the picturesque view of the surrounding mountains and valleys.

Guesthouse in Jamul

San Diego Mountain Retreat

3 bedroom 1 bathroom loft (2 separate sides) open concept guest house. Very peaceful East San Diego getaway. Enjoy beautiful ocean and Mountain Views during the day then relax in the jacuzzi with breath taking sunsets and the city lights at night. Best views in San Diego! Only 25 minutes from the SD airport and beaches. Minutes away from 2 local wineries and casinos. House sleeps 6 but you can invite guests up for the day for a fee. Event prices will be discussed per event. We live in main home

4.97 out of 5 average rating, 110 reviews

Lavender plants are prominently displayed in the foreground, with tall, slender purple blooms reaching towards a clear blue sky. In the background, a lush green lawn and trees are visible, enhancing the garden's serene setting.

Farm in El Cajon

Sycamore Creek cottage with Mountain View’s

Welcome to the Sycamore Cottage Retreat- a serene countryside escape set on a former horse & cattle ranch, where wide open skies, rolling pastures, and quiet vintage luxury come together. Tucked away in a peaceful valley, this thoughtfully designed cottage invites you to slow down and reconnect-with nature, with loved ones, and with yourself. Once home to horses and grazing cattle, the land still carries that grounding , pastoral beauty. The Cottage sleeps 2 1 Queen bed Pets welcome, pet fee.

4.9 out of 5 average rating, 105 reviews

A spacious private patio features a tiled floor and comfortable seating around a square table. Potted cacti adorn the edges, while the sunset casts a vibrant pink and purple hue over the surrounding hills and valleys, creating a serene backdrop.

Guesthouse in El Cajon

Hilltop Casita Mount Helix

View the sunrise and sunset from this panoramic hilltop casita. Enjoy a charming getaway with sweeping views of the mountains and valleys. Enjoy refreshments on private patio while taking in the sights of palm trees and endless hills. Located 15 miles from the beach and 20 minutes from many major San Diego attractions. Please note: we currently have an outdoor renovation project in process behind the casita. There may be days during your stay in which outdoor work is being performed.

Guest suite in Spring Valley

A modern kitchen is presented with butcher block countertops and stainless steel appliances. Open shelving displays decorative items, while plants add a touch of greenery. Two black stools are situated at a small dining space, and natural light filters through a window with a wood frame.

4.92 out of 5 average rating, 171 reviews

🤲🏼 Handmade hideaway Mt. Helix - AC/Laundry/Parking

Tucked away in the foothills of beautiful Mt. Helix, the Hand-made Hideaway has everything you need. - Pet friendly - 450 sf ground level apartment. - Private entrance with outdoor seating - Designated parking - Fully stocked kitchen and dining area - Safe, quite neighborhood - 20 minute drive to beaches, downtown, hiking areas - Ride-shares and delivery services readily available “The Hide-away is gorgeous! The pictures don’t do it justice - a lot of crafty considerations”

4.97 out of 5 average rating, 627 reviews

The exterior of a two-story guest house is illuminated in warm light, showcasing a balcony with railing that overlooks the surrounding greenery. A welcoming entrance is framed by well-kept garden areas, with steps leading up to the house.

Guesthouse in Dulzura

Vineyard & Winery Guest House

A hidden gem! Please send an inquiry if you are interested in staying with us. Get away and stay at the historic pioneer era Clark Ranch established in 1885. Our guest house sits above our winery tasting room and has its own private entrance and driveway. It's clean, cozy, and self-contained . Make it a weekend 'getaway' stay and sample our fine wines. There is a tower in the vineyard where you can enjoy a glass of wine and watch the sun set. Balcony overlooks Dulzura Creek.

4.95 out of 5 average rating, 221 reviews

Mountain top view getaway loft

This loft is completely sound proof! VIEWS, VIEWS, VIEWS!! Do not miss this stunning contemporary loft, located in the highly desired Mt. Helix community. The guest house faces west, giving you phenomenal 270-degree views of the ocean, Downtown, Point Loma, Coronado islands, Coronado bridge, and more! Designed and built by an acclaimed San Diego home designer, this property was featured in Dream Homes Magazine and is well known for its incredible design and construction.

4.96 out of 5 average rating, 202 reviews

A dining space features a round table with four white chairs, complemented by a potted plant. Large glass doors slide open to reveal expansive views of the backyard, pool, and surrounding hills, with soft evening light illuminating the scene.

Home in Spring Valley

Upscale Resort House /Views, Saltwater Pool/Spa !

This home offers Saltwater pool and Spa. Saltwater pools and Spa produce softer-feeling water. breathtaking views from its location high in the hills overlooking Rancho San Diego. In the backyard you can enjoy the sunrise from the private pool or deck or practice your putting on our putting green. The House is a mid-century modern home perched above the City. It's great for groups seeking easy access to San Diego's highlights (15 to 20 minutes to Beaches and Downtown)

4.97 out of 5 average rating, 348 reviews

The exterior view showcases a spacious parking area beneath a covered carport, surrounded by lush vegetation and vibrant flowers. The property features a neat driveway and a backdrop of rolling hills, enhancing the natural setting. The clear blue sky adds to the inviting atmosphere.

Cottage in La Mesa

La Mesa House On a Hill With Mountain Views!

SUNRISE PERCH - A standalone guest house, perfect spot for your San Diego stay! Enjoy inspiring sunrise views from the deck or relax indoors with super fast WiFi and a 43" TV. Enjoy a full kitchen! The king bed is super comfy and the bathroom is stocked. The space is only for those looking for quiet. No partying/loud socializing. Families welcome! Located 20 min from downtown San Diego and 25 min from the nearest beach (Ocean Beach).

A cozy interior features wooden paneling and a comfortable grey sofa with a decorative pillow. A small kitchenette is equipped with cabinets and appliances. A dining table is set for two, and a guitar is displayed on the wall, adding a touch of creativity to the space.

4.92 out of 5 average rating, 216 reviews

La Cabana

Perfect getaway for the wandering individual, couple, or young family. This rustic casita is surrounded by beautiful mountain and ocean views! Enjoy swimming in the pool, stargazing, lounging, or casual day trips around San Diego (All the amenities are shared with the main house) . The casita has one queen bed and a sofa bed, small kitchenette. Plenty of parking in driveway. Please read entire listing for details.

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

4.97 out of 5 average rating, 67 reviews

Two goats are positioned closely together, showcasing their distinctive markings. Their soft fur is complemented by a light-colored strap around one of their necks. The background depicts a natural setting with dry grass and wooden fencing, contributing to the farm's rustic charm.

Farm stay in El Cajon

Farmstay Gem near San Diego

Superhost

Guesthouse in Spring Valley

4.79 out of 5 average rating, 42 reviews

La Casita Guest House, yard, now with A/C, pets ok

5 out of 5 average rating, 15 reviews

Tierra Alta Casita

Superhost

The exterior of the house features a well-maintained yard with artificial grass and a decorative fountain. A spacious driveway leads to the two-car garage, while the backdrop reveals a picturesque lake and rolling hills under a clear blue sky.

Home in Spring Valley

4.96 out of 5 average rating, 73 reviews

Luxury 4 BR w/ Serene Lake Views

4.98 out of 5 average rating, 90 reviews

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.

Home in Jamul

Jamul Hacienda | Couples Retreat | Pool & Views!

4.94 out of 5 average rating, 65 reviews

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.

Apartment in El Cajon

Quaint Apt with International decor

4.97 out of 5 average rating, 72 reviews

An elevated view of a spacious backyard reveals a refreshing pool surrounded by lush greenery and palm trees. The home's exterior features solar panels on the roof and ample outdoor seating around the pool, creating a serene oasis for relaxation.

Home in Jamul

Hilltop 2200sqft Oasis: Pool, Views, BBQ

A cozy living area is furnished with a gray sleeper sofa and matching love seat, complemented by two accent tables. A large flat screen smart TV is mounted on the wall, and natural light enters through the front door and window adorned with shades. A dining area is visible in the background.