Family-friendly holiday rentals in Rancho San Diego

4.99 out of 5 average rating, 215 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.

Guest house 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.

4.97 out of 5 average rating, 108 reviews

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.

Guest house in La Mesa

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!

Guest house 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, 152 reviews

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

This is your perfect Guest House with a salt & heated pool + hot tub. Located in a super quiet & very safe neighborhood in beautiful San Diego, 15 minutes drive to the beaches, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike up Cowell Mountain next door at Mission Trails Park or around 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.

4.98 out of 5 average rating, 104 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.

Guest house 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

4.99 out of 5 average rating, 155 reviews

The welcoming entrance of Cedar Cottage is framed by lush greenery and decorative potted plants. A wooden porch, adorned with comfortable seating, leads to glass-paned doors. Elements such as a bubbling fountain and seasonal pumpkins add charm to the rustic facade.

Cottage in El Cajon

Cedar Cottage Retreat with Mountain View’s

Welcome to the Cedar 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 3. 1 Queen bed, one twin bed. Pets OK

4.86 out of 5 average rating, 117 reviews

A refreshing pool is surrounded by a spacious deck, showcasing lounge chairs and a large umbrella. Expansive views of the city and distant hills are visible under clear blue skies, creating a serene outdoor retreat.

Bungalow in El Cajon

Stylish Relaxation-Panoramic Views-Private OASIS!

~BRAND NEW DRIVEWAY~Perched high on granite hills, our comfy, stylish bungalow is perfect for a quiet getaway in San Diego. Brew your morning coffee and stroll to the pool to let the expansive views of the city fuel your daily adventures. Host a barbeque in the spacious, private backyard after your day at the beach. Cozy up in the recliner loveseat and enjoy the big screen 4k smart TV (with cable). 420 Friendly! “Enjoy the hillside pool—just coordinate with Johnny for your own private swim.”

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.

Guest house 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.

4.88 out of 5 average rating, 170 reviews

A comfortable seating area is observed, featuring a soft green sofa adorned with light-colored pillows. A small white side table holds a decorative arrangement of autumn-colored flowers. Natural light pours in through a large glass door, highlighting the pleasant, welcoming ambiance.

Ranch in Jamul

Fun 1 bd apt on a horse ranch, hiking and biking !

Welcome to our family petting zoo farm and horse ranch in Jamul! Our small ranch is in a quiet, beautiful valley with miles of trails right outside our gate. We horses, mini donkeys, goats, chickens and we sell fresh eggs, ask us! We are a 30 minute drive to the beaches, downtown San Diego, and most SD attractions. Locally we have a gas/convince/liquor store. Rancho San Diego is a 10 minute drive with Target, Grocery, Starbucks and many restaurants. We have hot water and WIFI.

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.

Guest house 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

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.

Guest house in La Mesa

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, 198 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)

4.92 out of 5 average rating, 214 reviews

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.

Guest house in La Mesa

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 family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 258 reviews

An expansive wooden deck showcases a cedar hot tub surrounded by nature. The area features additional seating, including two wooden chairs, and is framed by lush oak trees. Sunlight filters through the leaves, creating a warm and inviting outdoor space.

Home in Julian

Hot Tub | Disney Train Track | Secluded 20 acres

4.99 out of 5 average rating, 150 reviews

The tiny home is nestled among vibrant flowers and lush greenery. A rainbow arcs overhead, enhancing the cheerful exterior of the home, which features large windows and a welcoming porch. The surrounding landscape showcases a peaceful rural setting with gentle hills in the background.

Tiny home in Lakeside

Home at the Sanctuary

4.97 out of 5 average rating, 902 reviews

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.

Home in Ramona

The Glass House - A Nature Retreat

4.97 out of 5 average rating, 129 reviews

A custom cedar soaking tub is positioned on a stone patio, offering sweeping views of the surrounding hills and valleys. Two wooden chairs are situated nearby, providing a serene spot to relax. The clear blue sky enhances the natural beauty of the landscape.

Home in Julian

Luxury Julian Home w/ Cedar Tub, View, Horse Stall

A contemporary casita is featured with a neatly landscaped front yard and stone pathway leading to the entrance. A garage is visible to the left, and large windows allow natural light to illuminate the welcoming exterior, which is surrounded by lush greenery.

4.92 out of 5 average rating, 120 reviews

Sunnyside Resort Spa, Beach, Zoo, Arcade

4.91 out of 5 average rating, 379 reviews

An open living area features a large wooden dining table surrounded by six white chairs. A cozy sofa, adorned with neutral pillows and a blanket, overlooks expansive glass windows showcasing hillside views. A Christmas tree stands in the corner, adding a festive touch.

Home in Bonita

Glass Home with Views, Hot Tub, FREE EV Charging!

4.84 out of 5 average rating, 100 reviews

The Palm | Poolside Lounger• Hot Tub • GameRoom

4.98 out of 5 average rating, 254 reviews

A bright and inviting living area features a mustard-yellow sofa complemented by patterned cushions. Two armchairs in light grey are positioned around a wooden coffee table, while an acoustic guitar is mounted on the wall. A television is mounted beside large windows that allow natural light to stream in.

Bungalow in La Mesa

Townhouse - Hot Tub, Fire Pit La Mesa Village

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 128 reviews

A well-lit bedroom featuring a spacious bed adorned with decorative pillows and a soft bedspread. Two stylish lamps flank the bed, providing additional lighting. Natural light enters through a window, which is dressed with light curtains, emphasizing a serene and relaxing atmosphere.

Home in Spring Valley

Paradise View Staycation Q Bed, Sofa-bed *420 *

Guest suite in Spring Valley

4.92 out of 5 average rating, 107 reviews

Cozy Gem. 20 mins to Airport, Beaches, Gaslamp

Camper van/Motorhome in El Cajon

The interior of the trailer features a cozy sleeping area with a spacious bed adorned with decorative pillows. Wood paneling complements the mid-century modern design. A welcome sign and colorful decor are visible, along with a kitchenette and a refrigerator, enhancing the functional living environment.

4.94 out of 5 average rating, 326 reviews

Spring Sale in Bettie Blue RV fun!

4.91 out of 5 average rating, 479 reviews

A cozy living area features a wood-burning stove as the focal point, surrounded by string lights that add warmth. A round coffee table sits at the center, with a sofa and side chairs arranged for comfort. The walls are adorned with wooden panels, enhancing the rustic charm.

Cabin in Descanso

The High Country Hobo Preserve: Rustic Cabin

4.98 out of 5 average rating, 245 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.

Guest house in El Cajon

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

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, 170 reviews

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

Camper van/Motorhome in Ramona

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.

5 out of 5 average rating, 132 reviews

Luxury RV- Edge of the Cleveland Nat’l Forest!

4.94 out of 5 average rating, 201 reviews

A swimming pool reflects sunlight under a clear blue sky, surrounded by a patio area. A colorful hammock is suspended near the pool, while potted plants add greenery. The adjoining building features large windows and a seating area.

Guest suite in La Mesa

Hacienda de las Campanas (Bell Hacienda)

Family-friendly home rentals with a pool

Double glass doors provide access to the patio, revealing views of a kidney-shaped pool surrounded by a deck. Lush greenery and hills are visible in the background, creating a serene outdoor setting.

4.77 out of 5 average rating, 126 reviews

Views - Quiet Mt. Helix Home - Pool -Sleeps 11

A serene outdoor pool area features a refreshing blue pool surrounded by terracotta tiles. Two lounge chairs are positioned nearby, inviting relaxation. A wooden fence offers privacy while views of the landscape and sky are visible in the background, creating a tranquil atmosphere.

4.82 out of 5 average rating, 100 reviews

The Agave House | Mountain Views & Pool

4.88 out of 5 average rating, 219 reviews

A serene outdoor space features a salt-water pool surrounded by a concrete patio and manicured grass. An umbrella provides shade over the poolside area, with lush greenery and mountains visible in the background under a partly cloudy sky.

Home in Lake Murray

Bright and spacious home with views, pool & spa.

4.99 out of 5 average rating, 124 reviews

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.

Home in Ramona

The Dell, a relaxing country estate in Ramona.

4.8 out of 5 average rating, 133 reviews

The outdoor area showcases a clear pool surrounded by a spacious patio. Lounge chairs, a poolside table, and an umbrella are positioned for relaxation. The backdrop features low landscaping with cacti and a glimpse of the house, enhancing the tranquil setting.

Home in Lake Murray

Mid-Century Modern and Contemporary House

4.94 out of 5 average rating, 144 reviews

The outdoor pool area features a clear, inviting pool surrounded by a stone deck. Tall palm trees sway gently in the background, which is complemented by lush greenery. A shade sail is stretched overhead, providing comfort on sunny days.

Guest suite in La Mesa

Birdsong Suite | Family-friendly getaway

4.92 out of 5 average rating, 213 reviews

A private pool is surrounded by natural stone and lush greenery. Palm trees provide shade, while a bamboo privacy fence enhances the secluded atmosphere. The clear blue water invites relaxation, showcasing gentle ripples under the sunlight.

Home in Chula Vista

Oasis with ocean views/Pool/Hot tub! Sleeps 10!