Guesthouse 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, 173 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

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, 258 reviews

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

Da Hui Hut is a very private oasis uniquely situated at the top of San Diego county's magnificent Mt. Helix. At roughly 1,300 feet above sea level, Mt. Helix is the crown jewel of natural landmarks in the area. The landscape provides bountiful views, and the large deck is positioned perfectly to see it all. It feels like you're on top of the city! Inside, guests will encounter Californian and Hawaiian inspired decor as they collide with wooden walls to compose a symphony of color and good vibes.

An open layout studio is presented, featuring a cozy seating area with a grey couch and a rustic wooden coffee table. A dining space with a round table and chairs is visible. The kitchen area, equipped with modern appliances, is complemented by a ceiling fan with decorative light fixtures.

4.98 out of 5 average rating, 146 reviews

NEW construction - Studio by Village of La Mesa

New studio - Attached Dwelling Unit (ADU) with a private entrance. Walking distance to the Village of La Mesa which has several restaurants, shops and a Vons. Very close to SDSU and quick access to multiple freeways that take you to beaches, mountains, SD Zoo, the nightlife in downtown SD (8, 94, 125). Access to shared laundry room, 2 parking spaces and its own outdoor area. AC & heat. WiFi. Netflix, Hulu with live TV, Apple TV, Disney +, Prime Video and HBO Max. Crib and high chair upon request

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.

4.9 out of 5 average rating, 461 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!

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, 124 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!

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.

4.96 out of 5 average rating, 169 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, 230 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 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, 365 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

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.

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, 228 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.

A newly remodeled studio is showcased, featuring a private entrance and a black door, framed by potted plants. A spacious deck area extends below, with stairs leading down. An umbrella provides shade for outdoor seating, while lush greenery is visible in the background.

5 out of 5 average rating, 105 reviews

Beautiful Bright Mt. Helix Studio

This beautiful newly remodeled studio is in the heart of Mt Helix, a unique community in San Diego close to freeways, shopping, dining and more. Mt. Helix is called the lungs of San Diego because of it's lush surroundings and unique lots. We are surrounded by citrus orchards and are on a mountain giving you beautifully fantastic views. We are located in a private and quiet community just minutes from everything SD is so famous for.

Superhost

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.

Guesthouse in Normal Heights

4.99 out of 5 average rating, 482 reviews

Mountain View Retreat in Gated Estate (Hot Tub)

Perched above a canyon with spectacular panoramic mountain views, this private guest house is a secluded retreat in one of San Diego’s most eclectic and desirable neighborhoods less than 6 miles from the Downtown San Diego airport. Enjoy a fully equipped kitchen, luxe king size bed and dual sliding glass doors that open to an expansive deck with patio seating, private hot tub and BBQ area.

Popular amenities for La Mesa guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

4.99 out of 5 average rating, 198 reviews

A bright living area is characterized by large windows that invite natural light and provide views of greenery outside. A wall-mounted TV is positioned opposite a comfortable sofa, while a colorful dining chair adds a playful touch to the space.

Guesthouse in Del Cerro

The Happy Family * 2 playhouses & baby gear

The exterior of a two-story guesthouse is showcased, featuring a combination of wood paneling and painted walls. A bright white door and two small windows add contrast. The area is complemented by a compact patio set with two chairs and a table on a stone surface.

4.93 out of 5 average rating, 274 reviews

Fig Tree Bungalow

A spacious studio room features a queen-sized bed with a blue comforter, enhanced by wooden beams overhead. A comfortable seating area includes a sofa and coffee table. Large glass doors open to a patio, allowing natural light to fill the space.

4.99 out of 5 average rating, 295 reviews

Spacious, private Mt. Helix country style studio

An open living space featuring hardwood floors and exposed beam ceilings is shown. Comfortable seating arrangements include a sleek sofa and a red chair. A modern dining table sits adjacent to large windows, allowing natural light to brighten the area and offering views of the surrounding landscape.

4.86 out of 5 average rating, 114 reviews

The Carriage House at Mt. Helix

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.

4.98 out of 5 average rating, 253 reviews

Fletcher Hills - modern 1 BR.Easy, no step access.

A quaint wooden counter is displayed, featuring a vintage cash register and an old-fashioned gramophone. Behind the counter, shelves are filled with various antique items and collectibles, creating a nostalgic atmosphere. A wooden chair sits invitingly in front of the counter.

4.93 out of 5 average rating, 183 reviews

Granny Flat with Bedroom/Bathroom/Kitchen

4.88 out of 5 average rating, 240 reviews

Garden Room- Private Studio with a Panoramic View

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, 189 reviews

San Diego Newly Built Private Guesthouse (Sleep 4)

Guesthouses with a patio

Guesthouse in Mission Hills

A curving staircase is visible, flanked by white walls and adorned with vibrant blue tiles. Handrails provide support along the ascent, leading to a bright upper space. A potted plant enhances the serene ambiance at the top of the stairs.

5 out of 5 average rating, 263 reviews

Santorini-Inspired Cottage w/ Hot Tub + Views

4.98 out of 5 average rating, 128 reviews

Guesthouse in Bonita

Adorable 1- bedroom guesthouse/Casita

Guesthouse in Pacific Beach

An outdoor terrace features a spacious seating area with plush cushions, a central firepit, and lounge chairs overlooking a panoramic view of the landscape and ocean in the distance. The setting invites relaxation and enjoyment in a serene environment.

4.96 out of 5 average rating, 116 reviews

Beach views for 2! Jacuzzi, fire pit

A cozy outdoor seating area is framed by large glass windows, offering sweeping views of a vibrant sunset over the landscape. Plush cushions rest on a spacious sofa, inviting relaxation as the sky transitions to hues of orange and pink.

4.99 out of 5 average rating, 109 reviews

AmazingVIEWS! Hilltop Guest House with XL Balcony~

4.96 out of 5 average rating, 167 reviews

A private patio area is presented with a round dining table and four chairs, shaded by a large umbrella. Lush greenery surrounds the space, and sunlight filters through, creating a serene outdoor setting ideal for relaxation or dining.

Guesthouse in San Diego

SDSU Central Cozy Casita | Fast WiFi | Walkable

The living area features a spacious dark blue sectional sofa complemented by two brown leather armchairs. A flat-screen television is placed on a white media console. Decorative wall art is visible, along with a standing lamp and a potted plant, creating a cozy yet modern ambiance.

4.92 out of 5 average rating, 100 reviews

Cozy Hillside Retreat with View

Guesthouse in Spring Valley

The tiny cabin is illuminated by soft lighting, showcasing its wooden exterior and welcoming design. Surrounding cacti and plants enhance the natural setting, while steps lead up to a private deck. The evening sky provides a serene backdrop, highlighting the cabin's cozy atmosphere.

4.98 out of 5 average rating, 225 reviews

Loft Cabin•SoakTub•FirePit• Cinema•View+Zoo add-on

4.98 out of 5 average rating, 162 reviews

A spacious two-story guest house is presented, featuring a smooth concrete driveway and a large carport. The exterior is characterized by creamy white walls and stone accents. A basketball hoop is positioned nearby, contributing to the outdoor recreational possibilities.

Guesthouse in Lakeside

Cozy ADU in San Diego’s suburban rural mix area.

Guest house rentals with a washing machine and dryer

Guesthouse in Greater North Park

The exterior of a renovated guesthouse is presented, featuring a white stucco facade with decorative tiles along the steps. A green door, large windows, and a charming walkway leading to the stairs enhance the inviting appearance of the property.

4.99 out of 5 average rating, 196 reviews

Carrie’s North Park Casita, in Heart of San Diego

Guesthouse in Golden Hill

A bright bedroom is furnished with a gold metal bed, adorned with white linens and decorative pillows. Large windows allow natural light to fill the room, and a green plant adds a touch of nature. A comfortable chair and a small bedside table complete the decor.

4.94 out of 5 average rating, 425 reviews

*BEAUTIFUL* Sunny Home in Golden Hill

A welcoming entrance features a textured walkway leading to a front door, framed by a wooden railing. Colorful flowers bloom along the sloped landscape, enhancing the natural appeal of the surroundings. Clear skies and distant homes provide a serene backdrop.

4.99 out of 5 average rating, 224 reviews

Modern mountain guest house. Incredible views

Guesthouse in Ocean Beach

An open indoor space features a comfortable sofa adorned with decorative pillows. A large glass garage door leads to a private outdoor lounge area with natural greenery, seating, and a dining table, creating a seamless transition between indoor and outdoor living.

4.89 out of 5 average rating, 345 reviews

Indoor/Outdoor Sanctuary in Ocean Beach

Guesthouse in National City

An outdoor seating area features a covered gazebo with warm lighting, creating a welcoming ambiance. Surrounding the space are well-maintained grassy areas and neatly arranged stone pathways. Palm trees add a tropical touch against a backdrop of evening clouds and distant city lights.

4.95 out of 5 average rating, 234 reviews

Trendy 1 BR Guesthouse. Great views, no chores.

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.

4.97 out of 5 average rating, 212 reviews

Mt Helix Studio Loft with Mountain Views

Guesthouse in Mission Hills

A spacious living area features a large sectional sofa adorned with decorative pillows, complemented by a wooden coffee table. A vibrant wall art piece with colorful surfboards is displayed above the couch, while natural light fills the room through expansive windows.

4.97 out of 5 average rating, 296 reviews

Beautiful Historic Home and Gardens Near Downtown!