Family-friendly holiday rentals in Rancho San Diego

4.98 out of 5 average rating, 114 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

4.99 out of 5 average rating, 363 reviews

An aerial view captures the A-frame cabin surrounded by lush greenery. Warm light spills from large windows, illuminating the interior. The expansive deck is equipped with loungers, inviting seating areas, and a built-in BBQ, showcasing a welcoming outdoor space for relaxation.

Cabin in Julian

Mid-Century Modern A-Frame Secluded with Hot Tub

Secluded mid-century modern A-Frame cabin located in the Pine Hills community of historic Julian, CA. Built in 1969, the cabin completed a 2.5 year renovation in 2023 to meet modern tastes and amenities but keeps the original 60's groovy vibe. This unique family retreat offers a 900 sq ft deck, hot tub, firepits, and stunning views. Julian, a 1.5 hours drive east from San Diego, is a small town with big activities: hiking, biking, fishing, winery/breweries, winter sledding, apple pie eating.

Guesthouse in Spring Valley

4.98 out of 5 average rating, 442 reviews

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

Just 20 minutes from San Diego's most iconic attractions, yet seemingly a world away, this classic Airstream overlooks 30 acres of native California chapparal, wild sage and California pepper trees with sweeping city and sunset views Designed as a private nature retreat, it invites you to slow down, reconnect, and recharge. Soak beneath the stars, unwind in the handcrafted wood-fired redwood sauna, refresh under the open-air rain shower, and gather around the fire as city lights twinkle below

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, 175 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.

4.89 out of 5 average rating, 193 reviews

Farm stay in Jamul

Farm stay 1 bd on horse ranch with farm fresh eggs

Welcome to our family petting zoo farm and horse ranch in Jamul! Our small ranch is nestled in a quiet, beautiful valley with miles of hiking trails right outside our gate. We are a 30 minute drive to the beaches, downtown San Diego, and most SD attractions. We sell farm fresh eggs $5 a dozen if your interested 🤗 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, 132 reviews

A light-filled dining area features a simple white table set for two, complemented by wooden chairs. A comfortable seating area with neutral cushions is positioned against a green wall, while a glimpse of the kitchen is visible in the background, showcasing charming decor and a welcoming ambiance.

Guest suite in El Cajon

Farmhouse Cottage Retreat with Beautiful View’s

Welcome to the Farmhouse Cottage 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 in a comfortable Queen bed.

4.98 out of 5 average rating, 120 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!

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!

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, 236 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, 220 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)

Villa in Rancho San Diego

A serene outdoor area features a hot tub surrounded by stone elements and a waterfall feature. Sunlight filters through the overhead pergola, creating a play of light and shadow. Lush greenery and a glimpse of a spacious pool can be seen in the background.

4.9 out of 5 average rating, 294 reviews

Private Villa: Pool, Slide & Hot Tub

Summary: * Spacious: 5,000 SF indoor living space & 10,000+ SF outdoor living space * Fantastic Pool: Complete with waterslide, cave /grotto & multiple fountains / waterfalls * Relaxing Hot Tub: 5 hours of free heating daily from 5pm-10pm * Event Policy: No weddings, events, or parties with 16 or more guests * Accommodates: This home can accommodate up to 16 guests /see “more things to note" for more info on beds/air mattresses

4.96 out of 5 average rating, 393 reviews

Home in El Cajon

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**

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

4.99 out of 5 average rating, 212 reviews

A six-person hot tub is set against a backdrop of rolling mountains and valleys, providing expansive views of the landscape. The water is inviting, with bubbles rising gently. The area surrounding the hot tub is accented by natural stones and vegetation, enhancing the serene environment.

Home in Julian

Private Getaway - Breathtaking Views

4.97 out of 5 average rating, 929 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

4.96 out of 5 average rating, 417 reviews

A cozy living area showcases a modern yet rustic design, featuring a large wooden table and comfortable seating. Warm lighting from pendant fixtures complements the natural wood accents on the walls, while a decorative fireplace enhances the inviting atmosphere.

Farm stay in Lakeside

The Outside Inn at The Tipsy Goat Ranch

4.96 out of 5 average rating, 272 reviews

A stunning sunset is captured over a serene landscape, with the sun dipping below the horizon. Soft hues of orange and pink dominate the sky, reflecting on the water's surface. In the distance, the outline of an island is visible against the ocean.

Guesthouse in Jamul

Retreat house. Nature, Hot Tub, Views!

4.97 out of 5 average rating, 151 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.

4.9 out of 5 average rating, 138 reviews

Sunnyside Resort Spa, Beach, Zoo, Arcade

Villa in Rancho San Diego

An inviting outdoor entertainment area features a heated saltwater pool surrounded by elegant lighting and stylish lounge furniture. Inflatable swan floats rest in the water, while vibrant umbrellas provide shade over seating. Lush landscaping enhances the serene environment, making it ideal for relaxation.

4.92 out of 5 average rating, 212 reviews

Enchanted Paradise! ♨ Pool+Spa+Outdoor Kitchen ☀

4.98 out of 5 average rating, 277 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

4.94 out of 5 average rating, 329 reviews

The retro-style trailer is set against a green lawn, featuring turquoise and white stripes. Two white chairs with floral cushions are positioned beside a fire pit, creating a cozy outdoor seating area. Pink flamingo decorations add a playful touch to the surroundings.

Campervan/RV in El Cajon

Limited-Time Savings at Bettie Blue!

4.91 out of 5 average rating, 118 reviews

San Diego Oasis: Private Pool & Sunny Escape!

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, 178 reviews

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

4.99 out of 5 average rating, 147 reviews

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.

Campervan/RV in Ramona

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

4.98 out of 5 average rating, 120 reviews

Home in El Cajon

Quiet Country Home

4.98 out of 5 average rating, 517 reviews

Home in Encinitas

Lux Casita with Pickleball & Resort Amenities

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.

4.98 out of 5 average rating, 129 reviews

East Watch- a private getaway

4.98 out of 5 average rating, 260 reviews

An outdoor gazebo features a hot tub beside a small table and chairs. Lush greenery and plants surround the space, creating a private atmosphere. The patio is laid with pavers, enhancing the inviting environment for relaxation.

Home in Escondido

Gated Estate-Guest House-Private Backyard-Hot Tub!

Family-friendly home rentals with a pool

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.

4.81 out of 5 average rating, 102 reviews

The Agave House | Mountain Views & 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, 134 reviews

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

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, 179 reviews

Private 1 BR Paradise Retreat

4.84 out of 5 average rating, 215 reviews

A tiny house is nestled in a hillside, surrounded by lush greenery and cacti. The wooden structure features a spacious deck with seating, and large windows that invite natural light. Scenic mountain views are present in the background, enhancing the tranquil setting.

Tiny home in Escondido

Lakeview Tiny House w/hillside pool

4.87 out of 5 average rating, 237 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 San Diego

Bright and spacious home with views, pool & spa.

4.96 out of 5 average rating, 48 reviews

An inviting pool area is shown with a clear blue pool surrounded by tan decking. Lounge chairs are placed nearby, and a pergola offers shaded seating. Lush greenery and distant hillside views enhance the outdoor space under a bright blue sky.

Guesthouse in El Cajon

Sunset house

4.97 out of 5 average rating, 157 reviews

A welcoming front porch with comfortable seating is situated beneath a covered roof. Hanging flower baskets add a touch of color, while the neatly manicured lawn frames the entrance. The exterior features a light blue siding with white trim, creating a calm atmosphere.

Guesthouse in Ramona

Adorable Hawaiian themed Guest House