Family-friendly vacation rentals in Lakeside

4.99 out of 5 average rating, 191 reviews

The studio features exposed wooden beams and a spacious layout. A queen bed is positioned against the wall, while two comfortable chairs are set nearby. A well-equipped kitchen area with appliances and a counter is visible, alongside a door leading to the patio.

Tiny home in La Mesa

Townhouse - Private Yard, La Mesa Village

Enjoy a stylish experience at this centrally-located studio. Walking distance to La Mesa Village, where you can enjoy restaurants, coffee shops, boutiques, & more. With all the things you need in a kitchen to whip up any meal, and a patio to enjoy the San Diego sun. Hop on the trolley to get to anywhere. Bringing more friends or family along with you? We also have another listing, Casa de Pueblo at the same property. 20 min drive to the Beach or Downtown 15 min drive to Balboa Park or Old Town

4.95 out of 5 average rating, 388 reviews

A spacious bedroom features a king bed dressed with a patterned duvet. A stone fireplace adds warmth, while a dresser and TV are positioned nearby. Natural light filters through large windows, highlighting the vaulted wooden ceiling and creating an inviting atmosphere.

Guest suite in Santee

Spacious 1 Bdrm Unit: king bed, fireplace, parking

Come relax in this bright & spacious 1 bedroom detached unit with private entrance. This room has a king bed, fireplace, full bathroom, table & chairs, mini fridge/freezer, microwave, closet ,dresser, Tv and beautiful mountain views. La Jolla Beaches, downtown San Diego, the Zoo, and Sea World are 25 minutes away. Santee Lakes is just a short drive away where you can enjoy fishing, paddle boating, splash park, biking and picnic area. Mission Gorge Trails is also located just 5 minutes away.

4.93 out of 5 average rating, 122 reviews

A contemporary casita is set against a vibrant sunset, showcasing large windows that reflect the warm colors of the sky. The entrance features a clear path leading to a well-lit doorway, surrounded by natural landscaping and scenic hillside views.

Home in Lakeside

San Diego Casita for 6 Morey de Prieto Surf Ranch

The Morey de Prieto Surf Ranch is truly awesome! Reserve your stay in this 2 Bed/1 Bath 650 sq. ft. casita for six. Home includes a kitchen with a GE electric cooktop, refrigerator, microwave/air fryer, rice cooker, mixer for drinks, sink with prep trays, Moen faucet fixtures, gorgeous shower, Krups coffee maker, 50" smart TV equipped with WiFi and NetFlix, mountain views, workspace and a sofa bed. Relax on the large 240 sq. ft. private deck featuring a fire pit, adirondack chairs and BBQ.

5 out of 5 average rating, 118 reviews

A studio space features a queen bed with a patterned comforter, complemented by bedside lamps. A seating area with a reclining sofa is positioned near a 65" TV, providing an inviting setup for relaxation. The kitchenette is equipped with modern appliances, contributing to functional living.

Guest suite in Lakeside

Cozy, secure, and quiet studio in Lakeside

Studio granny flat w/full bath. Large windows front & back giving great natural light. Located at the end of a dead-end private drive. The 420 sq ft space includes a 65" HD TV w/DirectTV service, high speed wireless & wired internet, kitchenette w/convection cook microwave, fridge/freezer, w/many other extras. Unit was recently remodeled with new furniture. 1 Queen bed, dbl recliners, & dinette. (Also, the picture of the front of our property is not accurate - Airbnb uses Google photos 😕)

4.96 out of 5 average rating, 390 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

Nestled near Iron Mountain, a popular hiking destination, and less than 16 miles from San Diego's pristine beaches and local attractions, enjoy all SD has to offer in a one-of-kind farm-to-beach experience. Immerse yourself in a rarely seen side of San Diego you won't find anywhere else. Based on adventure, wrapped in luxury, a deep love for nature and the creatures it inhabits (mini goats, alpacas, babydoll sheep, lop bunnies, and chickens), it'll be a tranquil getaway you'll never forget.

4.99 out of 5 average rating, 145 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

Welcome to our charming and eco-friendly tiny home located in between fruit orchards and an animal rescue in a serene rural setting. The perfect place to disconnect from the hustle and bustle of city life and immerse yourself in nature. Wake up to the sounds of birds chirping and the sight of our resident farm animals grazing in the pasture. Pick any of the ripe fruit from over 70 different fruit trees. Come experience sustainable living and succulent garden in our charming tiny home.

4.96 out of 5 average rating, 135 reviews

An open living area features a comfortable sofa and a sleek glass coffee table. Natural light fills the space through large windows, complemented by soft curtains. Nearby, a dining area with seating and a well-equipped kitchen area is visible, enhancing the overall spacious feel.

Cottage in Lakeside

Modern Cottage Getaway!

Welcome to your cozy getaway! This charming 1,000+ sq ft cottage offers an open-concept layout. Perfect for couples, small families, solo travelers, or anyone looking for a peaceful retreat. 🧺 Washer and dryer included for added convenience Located in a very quiet, residential neighborhood—ideal for those seeking rest and relaxation. 🚗 Parking: Guests have 1/2 reserved parking spot in the driveway. No Street Parking 🚭 No smoking 🐾 No pets or service animals due to health concerns

4.99 out of 5 average rating, 116 reviews

An outdoor patio area features cushioned, wooden seating arranged around a gas fire pit. In the background, mountains and rolling hills are visible, complemented by a clear sky. A grill is seen in the corner, enhancing the outdoor living experience.

Guest suite in Sky Ranch

Hillside Retreat with Views

Escape to the mountains of San Diego and into a peaceful, well-furnished, private living space with plenty of room to spread out and enjoy the California lifestyle. Take in the panoramic views of El Capitan and the Cuyamaca mountain range as you enjoy your favorite beverage around the firepit. California awaits as you can wander east to the mountains and desert, or west to the beaches and shopping centers. Legoland, Seaworld, and the Sesame Place waterpark are all within a short drive.

4.98 out of 5 average rating, 181 reviews

A bedroom is equipped with a metal bed frame featuring a floral-patterned quilt. Two bedside lamps cast soft light, and wall art in calming colors adds a touch of design. Sliding glass doors reveal outdoor access to a private patio area with furniture.

Apartment in La Mesa

Lovely Hideaway Studio by Village-Private Patio

Enjoy the cool vibe at this unique rustic getaway tucked back on a tree-lined hill 5 minutes above City of La Mesa Village, 20 minutes from downtown San Diego. The studio is on the ground floor of our two-story house. We live on the 2nd floor, and the studio is it's own completely private space. 5 miles to San Diego State University; 16-20 miles to San Diego beaches; 10 miles to Downtown San Diego; 15 miles to Sea World San Diego; and 13 miles to the World Famous San Diego Zoo!

4.88 out of 5 average rating, 163 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, 106 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 stay in El Cajon

Sycamore Creek cottage with Mountain View’s

Welcome to Sycamore Creek Cottage. A unique retreat in the foothills of San Diego county. A Delightfully decorated, fully furnished 2 room studio cottage . Sleeps 1 or 2 in a comfortable Queen bed. 1 full bathrooms, Fully fenced private patio, BBQ , firepit area with beautiful garden and mountain views. Pet friendly. close to Alpine & Sycuan Resort & golf. Ideal for business travelers, work remotely, visiting family or friends . I look forward to hosting you.

A softly lit wooden pathway meanders through a lush garden, framed by greenery. Warm lights illuminate the edges, creating a serene ambiance as the path leads deeper into the vibrant landscape.

5 out of 5 average rating, 105 reviews

Shadow House Mt. Helix

Shadow House is a 1-bedroom 1-bathroom sanctuary nestled on an exclusive road, yet, oh so close to the vibrant heart of San Diego. This charming retreat is your perfect base camp as it's only 15 minutes away from sun-kissed beaches or downtown. With boutique hotel amenities and lush outdoor spaces, we’ve practically invented outdoor comfort with a side of charm.

Popular amenities for Lakeside family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in University Heights

A colorful living area features a vibrant blue couch adorned with decorative pillows. A round white coffee table sits prominently on a multi-colored rug, while a television is mounted above a red cabinet. Artwork and framed prints decorate the pink walls, enhancing the playful ambiance.

4.94 out of 5 average rating, 105 reviews

Casa De Colores

4.99 out of 5 average rating, 255 reviews

A charming cottage exterior features a brick pathway leading to the front door, surrounded by well-kept grass and shrubs. The wooden siding is complemented by a welcoming porch and a prominent chimney, set against a clear blue sky.

Cottage in La Jolla

La Jolla Shores redwood beach cottage

4.96 out of 5 average rating, 237 reviews

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.

Guesthouse in La Mesa

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

4.97 out of 5 average rating, 889 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, 255 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!

Guesthouse in Spring Valley

An Airstream is positioned on a hillside, surrounded by lush greenery and desert plants. Lounge chairs and a shaded patio area are visible, providing a space for relaxation. The backdrop features rolling hills under a clear sky, highlighting a peaceful and private setting.

4.98 out of 5 average rating, 410 reviews

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

4.93 out of 5 average rating, 422 reviews

A spacious studio is shown with warm wood flooring and white walls. A large window offers garden views, while a queen bed and a fold-down sofa bed provide sleeping options. A cozy workspace is positioned nearby, with a desk and chair, enhancing the room's functionality.

Guest suite in Escondido

Cozy Hilltop Garden Studio w/ City Views & Jacuzzi

A colorful studio space features turquoise walls and a ceiling fan. A comfortable sofa with decorative pillows is paired with a coffee table. A bed with a floral-patterned comforter sits against a window, while a TV and white refrigerator complete the modern setup.

4.98 out of 5 average rating, 310 reviews

SDCannaBnB #2 *420 *parking *dog-friendly *hot tub

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 161 reviews

An open living space is illuminated by natural light, featuring a light-colored sofa and a woven coffee table. A bed with neutral bedding is positioned beside a bright kitchenette. Decorative elements include a round mirror, a rattan light fixture, and a potted plant, enhancing the welcoming ambiance.

Guesthouse in San Diego

Insta-worthy! 1 night/many nights, no min required

4.96 out of 5 average rating, 157 reviews

A charming turquoise cottage is surrounded by tropical greenery. A spacious patio area features blue adirondack chairs and a dining table shaded by an umbrella. A winding brick path leads to additional cottages within the gated community.

Home in Ocean Beach

𖤓 OB Palms - 1 Br Close to all the Action!

4.87 out of 5 average rating, 147 reviews

Guest suite in Rolando

Spacious studio in La Mesa-near SDSU/Central 2 all

4.86 out of 5 average rating, 498 reviews

A comfortable living area features a high ceiling and large windows providing natural light and scenic views. A stone fireplace serves as a focal point, complemented by wooden furniture, a rocking chair, and a plush sofa. Warm, earthy tones create a cozy atmosphere.

Tiny home in Ramona

Wind n Tail Ranch Tiny House Homestay

4.94 out of 5 average rating, 323 reviews

Camper/RV in El Cajon

Spring Sale in Bettie Blue RV fun!

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, 168 reviews

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

4.97 out of 5 average rating, 189 reviews

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.

Guesthouse in El Cajon

Mt Helix Studio Loft with Mountain Views

4.98 out of 5 average rating, 488 reviews

Home in Encinitas

Lux Casita with Pickleball & Resort Amenities

Family-friendly home rentals with a pool

Superhost

The sunset illuminates the sky with vibrant hues, casting a warm glow over the swimming pool and surrounding backyard. Outdoor seating is arranged near the pool, complemented by lush greenery and a large rock. The scene evokes a sense of tranquility.

Guest suite in La Mesa

4.86 out of 5 average rating, 195 reviews

Peaceful Valley Ocean View - Restful and Relaxing

4.87 out of 5 average rating, 106 reviews

Entertainers Dream Pool Home

A spacious outdoor area features a clear blue pool surrounded by palm trees. Lounge chairs are positioned nearby, and a shaded table with chairs offers a spot for relaxation. The backyard showcases a privacy fence and ample sunlight.

4.85 out of 5 average rating, 232 reviews

San Diego Pool | Fire Pit | Sunshine | Sleeps 10

5 out of 5 average rating, 415 reviews

The pool area features a clear swimming pool surrounded by lounge chairs, palm trees, and a shaded seating space. The scenic backdrop showcases mountains under a partly cloudy sky, emphasizing the tranquil outdoor atmosphere.

Guesthouse in La Mesa

Private Poolside Cabana

4.81 out of 5 average rating, 176 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

4.94 out of 5 average rating, 140 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

4.96 out of 5 average rating, 190 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 !