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, 166 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

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, 145 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

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.

4.97 out of 5 average rating, 116 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!

4.98 out of 5 average rating, 262 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

Casa de Pueblo - 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

4.87 out of 5 average rating, 195 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.

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, 157 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.

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, 221 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.

A serene bedside scene features a spacious bed topped with crisp white linens. A modern nightstand stands beside it, holding a decorative white vase with greenery and a stylish lamp providing soft light.

4.88 out of 5 average rating, 268 reviews

5 Bed Zen Oasis | Fire Pit, BBQ, Laundry, Parking

Capture the essence of San Diego in our 3 bedroom house hosted by Ethos Vacation Homes. The peaceful property features elite comfort for up to 10 guests with beautiful outdoors and garden, fire pit table, BBQ grill, FREE laundry, central A/C and heating, 5 comfortable king and queen size beds, plenty of sheets and towels, 4 large HDTVs, Netflix, Max, Hulu, Disney+, Apple+, and ESPN+. This spacious San Diego vacation rental home has everything you need for your California Dreaming Vacation!

4.96 out of 5 average rating, 219 reviews

A spacious living area is presented with a gray sectional sofa adorned with colorful throw pillows. A round coffee table sits on a textured area rug. The kitchen features modern fixtures, while natural light fills the room through windows with a view of the patio.

Guest house in Rolando

Cozy Coop with a View

This house is perfect for a private get away. There is a patio bar & a large picture frame window that commands the best views in the area. Sit & enjoy the large patio right off the entryway to the house. I have been told our home used to be a chicken coop in the 50-60's. It is far different now, we just finished a complete remodel. Everything is updated, upgraded & ready for you. Being on the top of the hill you get the nice views, but sounds carries as well, please respect the neighbors.

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, 242 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!

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, 109 reviews

Mt. Helix Casita private petite home

This cozy, quiet retreat (5 min. from the quaint main street of downtown La Mesa) used to be a doll factory. Drink your morning ritual on our deck amongst the trees. 15 min. from downtown and SAN 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.

Superhost

4.84 out of 5 average rating, 107 reviews

Mountain View• Solar-heated Pool •HotTub •GameRoom

☀️Welcome to our fun, newly updated home in a quiet, secure neighborhood in La Mesa ☀️ 🌊Swim in our beautiful blue, solar-heated pool while enjoying an elevated mountain view, perfect for relaxation and fun. Unwind in our fantastic game room, equipped with a pool table, arcade machines and pop-a-hoop, offering endless entertainment for guest at all age. End the day in our in-home movie theater, where you can enjoy your favorite films in ultimate comfort. ☀️

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

A well-maintained putting green is surrounded by lush greenery, featuring multiple flags indicating different holes. A sand trap is positioned nearby, and a winding path made of stone leads through the garden space, enhancing the serene outdoor environment.

4.94 out of 5 average rating, 152 reviews

Pool Side Safari Cabin-On the backend of our Home

4.88 out of 5 average rating, 112 reviews

Entertainers Dream Pool Home

Guest suite in Spring Valley

A comfortable armchair with an ornate design is positioned near a glass door, allowing natural light to illuminate the space. An arched wall leads to the sleeping area featuring a spacious bed and decorative elements. Soft curtains frame the door, enhancing the serene atmosphere.

4.82 out of 5 average rating, 313 reviews

Comfy Mountain Top Casita

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, 248 reviews

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

4.9 out of 5 average rating, 189 reviews

A welcoming sitting room features two wooden chairs with green cushions and a comfortable sofa. In the center, a woven coffee table rests on a floral rug. A soft light is provided by a ceiling fixture, with doors leading to a bedroom visible in the background.

Guest suite in La Mesa

Charming Suite in Historic Home

Camper van/Motorhome in La Mesa

An Airstream trailer is situated under a wooden pergola, surrounded by decorative plants and a stone path. A comfortable seating area is positioned in front, featuring a cushioned bench with vibrant green cushions. The outdoor space offers access to the private courtyard.

4.99 out of 5 average rating, 143 reviews

Zen Airstream Experience

A scenic hillside is displayed, featuring a variety of homes nestled among lush greenery. The landscape showcases a blend of residential architecture within a mountainous region, with expansive views of the surrounding area under a clear blue sky.

4.93 out of 5 average rating, 124 reviews

Updated TownHome, Great Location, Fantastic Views

A well-lit bedroom features a spacious bed adorned with a light purple comforter. Nightstands are placed on each side of the bed, and a colorful floral area rug adds warmth to the floor. Light filters through sheer floral curtains, enhancing the calm ambiance.

4.86 out of 5 average rating, 165 reviews

Cozy Casita

Family- and pet-friendly home rentals

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, 103 reviews

Escape to tranquility: the perfect retreat

Guest suite in Spring Valley

4.92 out of 5 average rating, 112 reviews

Cozy Gem. 20 mins to Airport, Beaches, Gaslamp

4.93 out of 5 average rating, 102 reviews

San Diego Oasis: Private Pool & Sunny Escape!

4.98 out of 5 average rating, 248 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.

4.91 out of 5 average rating, 153 reviews

An outdoor seating area features a large sectional sofa in dark wicker with neutral cushions. A glass-top table sits in the center, complemented by an umbrella for shade. The space is enclosed by a wooden fence adorned with greenery and decorative flowers.

Home in College East

Cozy 2Bed-Private Parking, Dog Friendly, Big Yard!

4.99 out of 5 average rating, 128 reviews

Home in Rolando

Peaceful Casita | Firepit • Near SDSU

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, 226 reviews

Mountain top view getaway loft

A vibrant sunset casts shades of orange and pink across the sky, viewed from a residential street. Palm fronds frame the scene, while neighboring homes and trees are softly silhouetted against the colorful backdrop.

4.95 out of 5 average rating, 184 reviews

San Diego Newly Built Private Guesthouse (Sleep 4)

Family-friendly home rentals with a pool

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, 244 reviews

San Diego Pool | Fire Pit | Sunshine | Sleeps 10

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, 420 reviews

Private Poolside Cabana

4.96 out of 5 average rating, 406 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

4.88 out of 5 average rating, 225 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.

4.95 out of 5 average rating, 147 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

4.97 out of 5 average rating, 133 reviews

A serene backyard oasis features a small spa surrounded by lush greenery and decorative plants. The space is framed by an open wooden structure with a sloped roof, providing a cozy seating area with soft cushions. Unique pendant lights hang above, adding a touch of elegance.

Home in Normal Heights

Luxe Home w. Serene Backyard Spa

4.92 out of 5 average rating, 202 reviews

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.

Villa in El Cajon

Enchanted Paradise! ♨ Pool+Spa+Outdoor Kitchen ☀