Guesthouse holiday rentals in Rancho San Diego

The exterior of a historic stone cottage showcases a rounded structure with large, circular windows. Native plants and decorative rocks surround the entrance, highlighting the natural landscape. The name 'Anna' is displayed on a rustic wooden sign, further enhancing the cottage's character.

4.9 out of 5 average rating, 454 reviews

Anna's Historic Stone Cottage w/panoramic View!

Welcome to Anna's Historic Stone Cottage! The 110 year old cottage has been transformed into the perfect combination of romantic and rustic for a dream-worthy getaway. The 280sq ft cottage features stunning, panoramic views of the San Diego skyline while offering rooftop seating for sunrise and sunset viewing. The Cottage is conveniently located 20 minutes from the world famous San Diego zoo and most other must-see, tourist spots. Amenities for special occasions offered too. Check out our menu!

4.99 out of 5 average rating, 221 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, 119 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!

The exterior of a two-story guesthouse is showcased, featuring a combination of wood paneling and painted walls. A bright white door and two small windows add contrast. The area is complemented by a compact patio set with two chairs and a table on a stone surface.

4.93 out of 5 average rating, 271 reviews

Fig Tree Bungalow

Enjoy your stay in San Diego in this newly renovated guesthouse. Centrally located about a mile from Hwy 8, Hwy 125, and the Grossmont Trolley Station & Transit Center. Only a 15-20 minute drive to downtown, the airport, the beaches, and most of San Diego's other popular tourist attractions. This cozy, two-story, detached unit is located behind my home, and has its own private entrance and partitioned yard for your enjoyment. There's plenty of street parking directly in front of the house.

Guesthouse in Spring Valley

4.98 out of 5 average rating, 431 reviews

Airstream•Sauna•SoakTub• Views•Firepit+Zoo add-on

Nestled in a quiet hillside canyon only 20 min from Downtown San Diego, CA, this is a one-of-a-kind glamping retreat! ✦Private Hot Soaking Tub under the stars ✦Panoramic city/sunset views ✦Exclusive amenities ✦Custom wood-fired sauna ✦Golf chipping tee ✦Fast Wi-Fi ✦AC & Heat ✦Gated parking Cozy up by the fire as the city sparkles below or try your swing at the golf tee. Reconnect & recharge in your outdoor hot soaking tub, rain shower & wood-fired sauna - the perfect retreat for nature lovers!

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, 163 reviews

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

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & 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.

A private deck is shown, featuring a red umbrella over a round table with four chairs. The entrance to the guest house is framed by glass doors and accompanied by a vibrant red door. Lush greenery and flowerbeds enhance the outdoor space.

4.99 out of 5 average rating, 223 reviews

Stunning Guest House 15 min. from Zoo, Downtown

Stunning guest house that's 15 minutes to San Diego Zoo + downtown San Diego. The cottage is decorated with mid-century and one-of-a kind furniture in a comfy living space overlooking a gorgeous garden. Enjoy the the garden on your private deck, watch TV while relaxing in the handcrafted Nicaraguan rocker or 1950s Danish slipper chair. The cottage also has a comfy queen-sized bed and a full kitchen that's stocked with what you'd need. Oh, and all guests arrive to a homemade loaf of bread.

4.91 out of 5 average rating, 109 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.

Guesthouse in Spring Valley

4.99 out of 5 average rating, 417 reviews

Casita•Views•Outdoor Cinema• SoakTub+Zoo add-on

Escape to a private canyon retreat overlooking 30 acres of scenic hillsides just 20 minutes from Downtown San Diego ✦ Private Hot Soaking Tub ✦ Outdoor Movie Theater ✦ Panoramic Sunset & City Views (west facing) ✦ Entire casita - no shared walls, or above/below units ✦ Exclusive amenities - just for you! ✦ Fast Wi-Fi ✦ 50" Smart TV ✦ Quiet A/C & Heat ✦ Private Patio ✦ Gated Parking A perfect retreat for those wanting a special getaway on a very unique property overlooking the city!

4.98 out of 5 average rating, 250 reviews

A spacious living area is equipped with a plush sofa and light-colored chairs, accented by decorative pillows. A wooden coffee table rests on a colorful area rug. Natural light fills the room through two windows, highlighting a work desk and welcoming artwork on the wall.

Guesthouse in El Cajon

Fletcher Hills - modern 1 BR.Easy, no step access.

** 36 hours between check-ins. Thorough cleaning and sanitizing.. Four night minimum stay. Dogs ONLY are welcomed on a case by case basis. They must be house trained and are not permitted on any furniture. If you instant book, you must contact me about your pet within 24 hours. Smoking is permitted in the outside areas - patio, gazebo, yard. Easy freeway access helps any commute to downtown and area attractions. Having your own vehicle is the best way to get around..

A newly remodeled studio is showcased, featuring a private entrance and a black door, framed by potted plants. A spacious deck area extends below, with stairs leading down. An umbrella provides shade for outdoor seating, while lush greenery is visible in the background.

5 out of 5 average rating, 101 reviews

Beautiful Bright Mt. Helix Studio

This beautiful newly remodeled studio is in the heart of Mt Helix, a unique community in San Diego close to freeways, shopping, dining and more. Mt. Helix is called the lungs of San Diego because of it's lush surroundings and unique lots. We are surrounded by citrus orchards and are on a mountain giving you beautifully fantastic views. We are located in a private and quiet community just minutes from everything SD is so famous for.

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, 220 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 guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

A well-maintained putting green is surrounded by lush greenery, featuring multiple flags indicating different holes. A sand trap is positioned nearby, and a winding path made of stone leads through the garden space, enhancing the serene outdoor environment.

4.94 out of 5 average rating, 152 reviews

Pool Side Safari Cabin-On the backend of our Home

A charming exterior of a white house is framed by vibrant green plants and orange flowers. A stone pathway leads to an inviting front door, flanked by decorative lanterns. A small dog stands on the path, adding a sense of welcoming to the scene.

4.98 out of 5 average rating, 110 reviews

Mt. Helix Casita private petite home

4.99 out of 5 average rating, 193 reviews

A bright living area is characterized by large windows that invite natural light and provide views of greenery outside. A wall-mounted TV is positioned opposite a comfortable sofa, while a colorful dining chair adds a playful touch to the space.

Guesthouse in Del Cerro

The Happy Family * 2 playhouses near SDSU!

A spacious studio room features a queen-sized bed with a blue comforter, enhanced by wooden beams overhead. A comfortable seating area includes a sofa and coffee table. Large glass doors open to a patio, allowing natural light to fill the space.

4.99 out of 5 average rating, 293 reviews

Spacious, private Mt. Helix country style studio

Two red Adirondack chairs are positioned under a covered patio, facing a serene backyard with a pool. Lush greenery surrounds the area, creating a tranquil atmosphere. A BBQ room and various seating arrangements are visible beyond the pool, enhancing the outdoor retreat experience.

4.99 out of 5 average rating, 170 reviews

Private 1 BR Paradise Retreat

Guesthouse in Chula Vista

The exterior of a two-story building is surrounded by lush tropical plants, including tall palms and vibrant greenery. A paved walkway leads to a private entrance, which is framed by a low wall and several ornamental plants, creating an inviting and serene environment.

4.95 out of 5 average rating, 647 reviews

Private Casita in Great Eastlake Neighborhood

A modern loft space features warm wood flooring and a plush area rug. A gray sofa faces a sleek entertainment center. A desk and stool are situated by a window, offering views of the surrounding landscape. Natural light fills the room through large windows.

4.95 out of 5 average rating, 228 reviews

Mountain top view getaway loft

A spacious living area is presented with a gray sectional sofa adorned with colorful throw pillows. A round coffee table sits on a textured area rug. The kitchen features modern fixtures, while natural light fills the room through windows with a view of the patio.

4.95 out of 5 average rating, 222 reviews

Cozy Coop with a View

Guesthouses with a patio

4.98 out of 5 average rating, 122 reviews

Guesthouse in Bonita

Adorable 1- bedroom guesthouse/Casita

4.98 out of 5 average rating, 142 reviews

A private outdoor patio presents comfortable seating with two chairs and a sofa surrounding a coffee table. An umbrella provides shade, and greenery is visible alongside the patio. The paved surface features decorative stones, creating a cozy area for relaxation.

Guesthouse in Poway

Gorgeous Guesthouse Poway w/Private Yard

A vibrant sunset casts warm hues of orange and pink across the sky, contrasting with silhouettes of palm trees and distant hills. The scene captures the serene beauty of a Southern California evening, with a peaceful residential backdrop subtly illuminated by the fading light.

4.99 out of 5 average rating, 106 reviews

AmazingVIEWS! Hilltop Guest House with XL Balcony~

A spacious deck is visible, furnished with a table and four wicker chairs. A decorative bowl sits at the center of the table. The panoramic view of the surrounding landscape and city skyline stretches into the distance under a clear blue sky.

4.96 out of 5 average rating, 254 reviews

Da Hui Hut - La Mesa’s best view and spa

A cozy living area features a sectional sofa and wooden coffee table, complemented by a television mounted on the wall. Several light sources illuminate the space, including a ceiling fan. Decorative wall art adds a personal touch, while windows allow natural light to brighten the room.

4.99 out of 5 average rating, 356 reviews

SDCannaBnB #1 *420 *parking *dog-friendly *hot tub

4.96 out of 5 average rating, 193 reviews

Guesthouse in Julian

Cool Julian Mountain Nights • Firepit + Stars

An open layout studio is presented, featuring a cozy seating area with a grey couch and a rustic wooden coffee table. A dining space with a round table and chairs is visible. The kitchen area, equipped with modern appliances, is complemented by a ceiling fan with decorative light fixtures.

4.98 out of 5 average rating, 139 reviews

NEW construction - Studio by Village of La Mesa

4.87 out of 5 average rating, 232 reviews

Private Studio with a Panoramic View

Guest house rentals with a washing machine and dryer

Guesthouse in Golden Hill

A bright bedroom is furnished with a gold metal bed, adorned with white linens and decorative pillows. Large windows allow natural light to fill the room, and a green plant adds a touch of nature. A comfortable chair and a small bedside table complete the decor.

4.94 out of 5 average rating, 421 reviews

*BEAUTIFUL* Sunny Home in Golden Hill

4.95 out of 5 average rating, 146 reviews

A bright living area features a cozy sofa paired with a stylish coffee table, surrounded by large windows that allow natural light. A round mirror hangs above the seating, while indoor plants add a touch of greenery, creating a serene atmosphere.

Guesthouse in Poway

Charming Guest House in Poway - Kid friendly

4.93 out of 5 average rating, 105 reviews

A softly lit pool area is highlighted by string lights, reflecting gently on the water's surface. A small wooden structure is visible at the pool's edge, surrounded by lounge chairs. The tranquil ambiance is enhanced by the deep blue of the evening sky.

Guesthouse in Julian

el Castillo - spanish-inspired getaway in SD mtns

4.96 out of 5 average rating, 123 reviews

A modern kitchen space features wood cabinetry complemented by stainless steel appliances. A dining table with two chairs sits alongside a vibrant flower arrangement. Natural light enters through a nearby window, illuminating the open layout and inviting atmosphere.

Guesthouse in Poway

Private GuestHouse with Kitchen,Bath,Dryer, Washer

4.98 out of 5 average rating, 361 reviews

The entrance to the apartment is framed by a charming pathway, leading to a welcoming front door. Two light-colored chairs sit on the porch, surrounded by landscaped greenery and decorative stones. The overall design features a blend of stone and wood, creating an inviting entry.

Guesthouse in Escondido

Private 2 bedroom apt in new craftsman ranch!

Guesthouse in Rancho Santa Fe

A spacious outdoor area features a pool and spa surrounded by tropical landscaping and palm trees. Sunlight reflects off the water's surface, creating a serene ambiance. Comfortable seating is arranged nearby, enhancing the inviting atmosphere of the space.

4.99 out of 5 average rating, 182 reviews

Rancho Relaxo / Spacious Detached Guest House

4.98 out of 5 average rating, 120 reviews

A cozy living space is furnished with a dark leather sofa facing a coffee table. A dining area, equipped with a wooden table and four chairs, is visible. Light-colored walls are complemented by plantation shutters and two art pieces, while a ceiling fan hangs overhead.

Guesthouse in Alpine

Gorgeous Guest Home