Family-friendly vacation rentals in Lakeside

4.99 out of 5 average rating, 187 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, 381 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.

4.94 out of 5 average rating, 116 reviews

A spacious living area features a large, modern sectional sofa and a round dining table. A ceiling fan provides airflow, while a 50" smart TV displays a vibrant underwater scene. Light floods in through large windows, enhancing the inviting atmosphere, with surfboards displayed on the wall.

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, 116 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, 387 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, 141 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.

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, 326 reviews

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

Welcome to SDCannaBnB - San Diego's premier cannabis-friendly rental! Our casita is newly remodeled with luxury ammenities. We proudly cater to the cannabis community and non-users alike. Our casita has HEPA air purifiers, is fully ventilated and receives deep cleanings between each guest. This ensures that every guest checks into a clean, fresh-smelling place that feels like home. Our casita is located in our quiet, fully fenced in backyard, close to San Diego's attractions

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, 114 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, 179 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!

Apartment in Cherokee Point

A lush garden path leads through vibrant greenery, featuring blooming roses and various colorful flowers. Tropical palm trees rise in the background, and the exterior of the house is painted in a soft hue, creating a welcoming atmosphere in the outdoor space.

4.88 out of 5 average rating, 245 reviews

Private Studio close by North Park

Fiber WIFI, twin bed, TV (Roku & Netflix), microwave, fridge, hotplate, toaster, coffee maker, desk, office chair, armchair, folding table, iron & board. No pets please. Quiet, clean, central location. Free offstreet parking. Walk to University Ave eateries, shops, buses. See Host Guidebook. 1 mi to 30th St/North Park, 10 min drive to Balboa Park, Downtown, Airport. #7, 10 & 215 bus to downtown. Near I-I5, 805, I-8 freeways. Check-in: Lockbox. Cleaned & Disinfected for Your Safety.

Guest suite in Lemon Grove

A compact kitchenette features cream-colored cabinetry complemented by a vibrant blue countertop. Appliances include a microwave and refrigerator, with cooking utensils and dishware neatly arranged on the open shelves above. A flat-screen TV is mounted on the wall, enhancing the functional space.

4.87 out of 5 average rating, 252 reviews

GROVE CASITA/ Amiable Room, Private Enrty, Bath

Quaint Guest Space - 2 easy, fast access ways to Freeway - Keypad entry - Parking - AIR CONDITIONING, - Wired internet, Wi-Fi - Laundry - 10 to 15 minutes to downtown San Diego, the Convention Center, Little Italy, and 32nd Naval Base, San Diego Zoo/ Balboa Park, Coronado Island beach - 15 to 20 minutes to Sea World, Tijuana Mexico, La Jolla, Imperial Beach, Ocean Beach - 1.6 miles to Trolley - 0.6 miles to bus Bus lines - Close to Grocery Stores , fast food, and restaurants

Popular amenities for Lakeside family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 118 reviews

A refreshing pool area is surrounded by lush tropical foliage and rock formations. Waterfalls cascade from a natural stone archway into the turquoise water, creating a serene atmosphere. Smooth stone pathways lead around the pool, enhancing the space's inviting nature.

Home in La Mesa

Paradise Lagoon Resort Style Pool Getaway

4.99 out of 5 average rating, 252 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

Guesthouse in Normal Heights

A spacious bedroom features a large king size bed with a textured blanket, complemented by a nightstand and a decorative lamp. Sliding glass doors open to a deck, allowing natural light to fill the room. A flat-screen TV and a desk are visible in the background.

4.98 out of 5 average rating, 461 reviews

Mountain View Retreat in Gated Estate (Hot Tub)

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, 234 reviews

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

4.93 out of 5 average rating, 412 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

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

4.94 out of 5 average rating, 319 reviews

A spacious living area features large glass sliding doors that reveal an expansive ocean view with a sunset. Comfortable seating includes a modern gray sectional and two accent chairs, inviting relaxation. The room is illuminated with warm, natural light, enhancing the serene coastal atmosphere.

Condo in Pacific Beach

Beach Front Condo - Capri by the Sea - Remodeled

4.97 out of 5 average rating, 311 reviews

Home in Ramona

Wine Country Retreat - Tranquility Hottub/Views

Family- and pet-friendly home rentals

Apartment in Little Italy

An open living space is highlighted by a large sectional sofa and a round coffee table. The neutral-toned decor includes a colorful area rug. A dining table with two chairs is visible, while the kitchen area features a minimalist design with essential appliances.

4.92 out of 5 average rating, 213 reviews

State & Fir (Little Italy Loft, Free Parking)

4.97 out of 5 average rating, 152 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

Bungalow in Mission Hills

A spacious bed with a striped comforter and two plush pillows occupies the center of the room. Soft bedside lamps provide warm lighting, while a framed artwork hangs on the wall above the bed. Two small, elegant stools are positioned beside the bed.

4.79 out of 5 average rating, 524 reviews

Quiet studio: King bed, AC, Washer

4.87 out of 5 average rating, 146 reviews

A spacious bedroom features a comfortable bed with a textured blanket and several decorative pillows. Soft lighting is provided by wall sconces, and a circular mirror adds visual interest. A patterned bench sits at the foot of the bed, alongside a stylish closet and a decorative basket.

Guest suite in Rolando

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

4.94 out of 5 average rating, 323 reviews

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.

Camper/RV in El Cajon

Stay in a Retro Camper | A Tiny Adventure Awaits

4.86 out of 5 average rating, 496 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

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

5 out of 5 average rating, 118 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.

Camper/RV in Ramona

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

Family-friendly home rentals with a pool

Superhost

A two-story building is set among lush greenery, with well-manicured lawns and trees. Pathways lead to the entrances, while a balcony extends from the upper floor, providing outdoor space. The surrounding nature enhances the tranquil setting against a backdrop of rolling hills.

Hotel room in Ramona

4.82 out of 5 average rating, 162 reviews

One Bedroom Condo in San Diego Country Estates

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

4.87 out of 5 average rating, 192 reviews

Peaceful Valley Ocean View - Restful and Relaxing

Guesthouse in Allied Gardens

A cozy bedroom is highlighted by a neatly made bed, featuring a patterned quilt and two pillows. A small tray with snacks sits attractively on the bed. Natural light pours in through a window adorned with light curtains.

4.94 out of 5 average rating, 431 reviews

The BEST NEST Clean, peaceful, private, affordable

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, 147 reviews

Private 1 BR Paradise retreat

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.

5 out of 5 average rating, 414 reviews

Private Poolside Cabana

4.81 out of 5 average rating, 171 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

4.93 out of 5 average rating, 196 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)