Family-friendly holiday rentals in La Mesa

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, 177 reviews

Private 1 BR Paradise Retreat

Private, yet central. It is your exclusive paradise retreat to enjoy from your spacious 1 bedroom guest house located on the lower level of our home. Hang out in the expansive and private backyard with pool, different sitting areas and covered BBQ room. Or maybe a workout in the gym. Centrally located in the Village of La mesa. Just a 1/4 mile jaunt into the quaint village with its numerous assortments of dining options, stores and trolley station. Freeway close to beaches, downtown and airport

Indoor spacesKitchenAccuracy

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.

4.91 out of 5 average rating, 466 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!

FamilyIndoor spacesGetting around

An outdoor seating area is equipped with sectional sofas arranged around a fire pit, featuring a grassy lawn surrounded by lush greenery. A large tree provides shade, while a spacious porch is visible in the background, contributing to the serene atmosphere.

4.94 out of 5 average rating, 158 reviews

Family Fun! Game Garage + Big Yard + Free Parking

Embodying the epitome of cool! This home has the perfect blend of a vintage feel with a modern touch. Stepping inside, you’re greeted by an atmosphere of fun & creativity. A large private serene retreat in the backyard w/abundant seating and fire pit. Huge 3-car garage bonus space with games. Located just minutes from downtown La Mesa, many dining options & conveniences. Everything you need & more! Distance to: San Diego Zoo: 18 min Sea World: 23 min SDSU: 13 min Airport: 19 min Gaslamp: 18 min

Indoor spacesKitchenCheckout

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, 127 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!

FamilyIndoor spacesLocation

4.99 out of 5 average rating, 176 reviews

A spacious sleeping area is featured, highlighted by a plush green bedspread atop a comfortable bed. Flanking lamps on either side provide soft illumination, while a large round mirror reflects the room's light. Decorative artwork and potted plants add a serene touch.

Guest suite in La Mesa

Emerald Suite Spa Experience with Sauna & Desk

Soothe your senses and unwind in your private spa retreat, featuring a restorative sauna, a huge soaking tub, and the refreshing scent of eucalyptus aromatherapy. Sink into a luxuriously comfortable king bed, surrounded by a calming ambiance. Thoughtful touches like plush robes and a chilled filtered water dispenser elevate your experience. Set in a tranquil neighborhood with easy access to San Diego’s highlights, this sanctuary offers the perfect blend of relaxation, rejuvenation, and comfort.

Indoor spacesFamilyQuiet

4.98 out of 5 average rating, 273 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

Enjoy a stylish experience at this centrally-located bungalow. Just a short walk to La Mesa Village, where you can enjoy restaurants, coffee shops, boutiques, & more. The outdoor space has a hot tub, fire pit, yard games, & bbq. Hop on the trolley to get anywhere. Traveling with additional friends and family? We have the Casita de Pueblo located at the same location. Check it out under our other listings where you can book both. 20 min drive to the Beach, Downtown, Balboa Park, or Old Town

KitchenIndoor spacesHospitality

4.87 out of 5 average rating, 206 reviews

An open kitchen and living area is shown, featuring a modern design with white cabinetry and wooden accents. A comfortable sofa is positioned in front of a wall-mounted TV. A dining table with seating for four is placed next to the kitchen, surrounded by natural light.

Guest suite in La Mesa

Stylish Boho Studio | Walk to Cafes | Outdoor Livi

The studio is located within a quiet leafy neighborhood right in the heart of La Mesa giving you a great base to explore everything San Diego has to offer. Inside you will find a bright, sun-filled space with a chic kitchen, an open plan living/dining area with a comfortable sofa bed, a stylish queen bedroom and a modern, sparkling bathroom with a built in laundry. Stay a short 15 min walk to a shopping center nearby with cafes, restaurants and stores and an easy 15 min drive into Downtown.

KitchenIndoor spacesCleanliness

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, 173 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.

FamilyKitchenHot tub

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, 231 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.

Indoor spacesKitchenLocation

A view into a modern living space reveals a sleek kitchen with bar seating and a spacious dining area. Natural light floods the room through large glass doors, showcasing lush greenery outside. A cozy area is completed with a colorful rug beneath and a inviting seating arrangement.

4.93 out of 5 average rating, 244 reviews

Cottage in the Garden! New! Modern!

COTTAGE IN THE GARDEN - New! Modern! Find beauty and serenity in this special guest house in one of San Diego's most desirable areas! Flowering bushes, plants, olive tree and fruit trees seen from all windows. All amenities: WiFi, Cable, serving dishes and tableware, full coffee bar, Ninja Blender, Flat screen TVs, 100% Egyptian Cotton Sheets or Boll and Branch Sheets (used by 3 Presidents), Japanese Toilette and more. 15 minutes to Downtown San Diego and 20 minutes to the beach!

Indoor spacesFamilyAccess

4.98 out of 5 average rating, 192 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!

Indoor spacesKitchenHospitality

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, 112 reviews

Enchanting private Mt Helix retreat close to SDSU

This quiet retreat (5 min. from the quaint main street of downtown La Mesa) used to be a doll workshop. Drink your morning ritual on a private deck amongst the trees. 15 min. from downtown and SD airport. 10 minutes from SDSU. 25 minutes to La Jolla/ beaches and most San Diego colleges and attractions like Birch Aquarium. 15 minutes from Balboa Park museums. Hike Mission trails-15 min. from trailheads. Take a walk up scenic Mt Helix and enjoy the vistas. Flora and fauna abound.

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Popular amenities for La Mesa family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 293 reviews

Private Villa: Pool, Slide & Hot Tub

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A spacious outdoor area features a swimming pool, accompanied by colorful lounge chairs and a large umbrella for shade. A unicorn float is visible in the water, with potted flowers adding a touch of vibrancy. The home's façade offers multiple windows and seating options nearby.

4.99 out of 5 average rating, 201 reviews

Mid-Century Style Family House with Spa

KitchenFamilyComfort

4.91 out of 5 average rating, 115 reviews

HotTub & 100+ Game Arcade Family Getaway San Diego

Indoor spacesKitchenBathroom

A private pool is surrounded by a spacious patio, featuring a built-in spa and floating pool accessories. Lounge chairs are arranged by the poolside, while the nearby house is complemented by green shrubbery and playful palm trees. Bright sunlight highlights the inviting blue water.

4.9 out of 5 average rating, 109 reviews

QUIET HOME -3 Bedroom & Den, + POOL, sleep 8 plus

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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, 374 reviews

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

FamilyKitchenLaundry

4.82 out of 5 average rating, 120 reviews

A light-filled living area features a comfortable white sofa adorned with various pillows. A small marble table sits in front of the sofa, complemented by fresh tulips in a vase. A side chair and decorative elements add to the inviting ambiance.

Condo in La Mesa

Sweet Little La Mesa Condo(pool+hot tub) NEAR SDSU

Indoor spacesKitchenCondition

4.98 out of 5 average rating, 132 reviews

A well-appointed backyard features a heated pool with a waterfall, surrounded by palm trees and lounge chairs. An outdoor dining area is under a covered gazebo, providing a view of the landscaped space. Soft evening light hints at a serene atmosphere.

Home in Spring Valley

Tropical Oasis: spa, solar heated pool, waterslide

Indoor spacesFamilyCondition

4.86 out of 5 average rating, 121 reviews

Entertainers Dream Pool Home

Indoor spacesFamilyLaundry

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 713 reviews

The interior of the dome showcases unique angular wooden walls, creating a modern architectural feature. A spacious open area includes a small dining table with a chair, a comfortable sofa, and a television. Large windows provide natural light and views of the outside greenery.

Dome in La Mesa

Dome Life

Indoor spacesKitchenAccess

A view of the inviting swimming pool surrounded by a spacious patio. Natural rock elements and vibrant landscaping enhance the outdoor area. The multi-level deck is visible, offering seating options and picturesque canyon surroundings under a clear blue sky.

4.9 out of 5 average rating, 212 reviews

The Queen House

FamilyKitchenValue

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, 234 reviews

Mountain top view getaway loft

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A private guest home features a modern exterior with corrugated metal siding and a vibrant red door. A wooden deck is visible, surrounded by greenery, providing an inviting entrance. Two small windows are positioned on either side of the door, offering natural light.

4.99 out of 5 average rating, 323 reviews

Hawks nest

FamilyIndoor spacesPets

A welcoming living area features a spacious beige sectional sofa adorned with patterned throw pillows. Natural light filters through a large window, complemented by soft, flowing curtains. A dark ottoman with decorative details adds a contrasting element to the cozy space.

4.96 out of 5 average rating, 139 reviews

Zen Retreat: 3-Bedroom Oasis near La Mesa Village

KitchenFamilyWalkability

4.93 out of 5 average rating, 116 reviews

San Diego Oasis: Private Pool & Sunny Escape!

KitchenFamilyValue

An outdoor patio area features a glass table shaded by an orange umbrella. Two chairs are positioned nearby, surrounded by green grass and trees. The peaceful setting includes wooden fencing in the background, adding to the privacy of the space.

4.98 out of 5 average rating, 111 reviews

Escape to tranquility: the perfect retreat

KitchenIndoor spacesValue

4.98 out of 5 average rating, 254 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.

KitchenIndoor spacesLocation

Family-friendly home rentals with a pool

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.

4.93 out of 5 average rating, 228 reviews

La Cabana

Indoor spacesKitchenWalkability

5.0 out of 5 average rating, 429 reviews

Private Poolside Cabana

KitchenIndoor spacesBathroom

Superhost

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

KitchenFamilyDecor

The property features a spacious backyard with a heated pool surrounded by lounge chairs. Palm trees line the perimeter, and soft lighting illuminates the outdoor area during sunset. The two-story house overlooks the pool, creating an inviting atmosphere for relaxation and gatherings.

4.94 out of 5 average rating, 248 reviews

Family Pool Retreat + Gym, Fire Pits, Views (Sleep

KitchenIndoor spacesHospitality

4.96 out of 5 average rating, 217 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 !

FamilyIndoor spacesGetting around

4.85 out of 5 average rating, 257 reviews

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.

Home in El Cajon

San Diego Pool | Fire Pit | Sunshine | Sleeps 10

KitchenIndoor spacesAccess

4.96 out of 5 average rating, 119 reviews

An outdoor seating area is equipped with a sectional couch surrounding a stone fire pit, with flames flickering invitingly. A large dining table offers ample seating. The heated pool glistens in the background, surrounded by lounge chairs and shaded umbrellas.

Home in El Cajon

Family Fun Oasis Pool Spa and Game Room

Indoor spacesFamilyBackyard