Guest house holiday rentals in La Mesa

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, 477 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!

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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, 185 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

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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, 161 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

FamilyLocationLong stay

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, 266 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.

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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, 133 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!

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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, 279 reviews

Fig Tree Bungalow

Enjoy your stay in San Diego in this newly renovated guesthouse. Centrally located about a mile from Hwy 8, Hwy 125, and the Grossmont Trolley Station & Transit Center. Only a 15-20 minute drive to downtown, the airport, the beaches, and most of San Diego's other popular tourist attractions. This cozy, two-story, detached unit is located behind my home, and has its own private entrance and partitioned yard for your enjoyment. There's plenty of street parking directly in front of the house.

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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, 181 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.

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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, 233 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.

ValueFamilyLong stay

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, 385 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

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4.98 out of 5 average rating, 114 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.

FamilyLocationLong stay

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, 304 reviews

Spacious, private Mt. Helix country style studio

Located in a quiet and lush neighborhood, in hills of La Mesa. This private studio has everything you need to relax and experience the California life: comfy queen size bed, full kitchen, patio, bbq, and fire pit. Within walking distance to Mt. Helix Historic Park for a spectacular 365-degree view of San Diego. You are 20 minutes from the beach, airport, and mountains.

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4.88 out of 5 average rating, 255 reviews

Garden Room- Private Studio with a Panoramic View

Escape to Your Hilltop Retreat! Relax in secluded studio. Sip wine by the cozy fire pit or unwind on the patio with a bird’s-eye view. Conveniently located just 15-20 minutes from the beach and downtown, you’re never far from the action. Bringing more friends or family along with you? We also have another listing, The Eagles Nest at the same property.

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Popular amenities for guest house rentals in La Mesa

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

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, 234 reviews

La Cabana

ValueFamilyBathroom

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.

4.95 out of 5 average rating, 232 reviews

Cozy Coop with a View

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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, 196 reviews

San Diego Newly Built Private Guesthouse (Sleep 4)

ValueLocationLong stay

5.0 out of 5 average rating, 210 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.

Guest house in Del Cerro

The Happy Family * 2 playhouses & baby gear

ValueFamilyHeating

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.

4.94 out of 5 average rating, 188 reviews

Granny Flat with Bedroom/Bathroom/Kitchen

ValueFamilyTV

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, 242 reviews

Mountain top view getaway loft

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Superhost

The living area features a grey sofa complemented by two pink chairs arranged around a low coffee table. An ornate area rug anchors the space, while framed botanical art adorns the wall. A large mirror reflects the light from stylish floor lamps and greenery.

Guest house in San Diego

Farm Vibe near City with Friendly Goats & Big Deck

ValueFamilyWifi

4.93 out of 5 average rating, 248 reviews

Guest house in Lemon Grove

A cozy living area features a dark sectional sofa adorned with various cushions. A round coffee table is placed in front, set on a plush area rug. Two windows with patterned curtains allow natural light to enter, highlighting the warm tones of the space.

Adorable Lemon Grove Studio

ValueFamilyBack garden

4.97 out of 5 average rating, 224 reviews

Guest house rentals with a patio

Guest house 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.

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

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4.98 out of 5 average rating, 233 reviews

Superhost

The bathroom features a modern design with a glass-enclosed shower and a spacious vanity. A dark cabinet complements the white walls, while a bright yellow rug adds a pop of color to the black hexagonal tile floor. Ample lighting is provided above the mirror.

Guest house in Spring Valley

*Look*Secluded/studio/getaway w/ Sunset View+patio

ValueLocationWifi

4.8 out of 5 average rating, 100 reviews

4.93 out of 5 average rating, 107 reviews

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.

Guest house in El Cajon

Cozy Hillside Retreat with View

ValueLocationWifi

4.99 out of 5 average rating, 112 reviews

AmazingVIEWS! Hilltop Guest House with XL Balcony~

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4.96 out of 5 average rating, 174 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.

Guest house in San Diego

SDSU Central Cozy Casita | Fast WiFi | Walkable

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Guest house 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.

Beach views for 2! Jacuzzi, fire pit

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4.95 out of 5 average rating, 128 reviews

4.85 out of 5 average rating, 260 reviews

A peaceful residential exterior is shown with a two-story house featuring a balcony. Lush greenery and colorful flowers border the driveway, which provides ample space for parking, including a white vehicle. The entrance is framed by a decorative gate and a brick pathway.

Guest house in San Diego

Keighley Guest Apartment (balcony w/views, A/C)

ValueLocationView

An open living area is shown with a cozy sofa adorned with decorative pillows. A spacious bed with neutral bedding occupies one corner, while a wooden desk and chair are positioned nearby. A ceiling fan and wall-mounted air conditioning unit provide comfort.

4.96 out of 5 average rating, 138 reviews

Violet Oasis | hot tub + kitchen, dog friendly!

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Guest house rentals with a washing machine and dryer

Guest house 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.

*BEAUTIFUL* Sunny Home in Golden Hill

ValueLocationKitchen

4.94 out of 5 average rating, 436 reviews

Guest house in Normal Heights

The “OUT” House: Artist’s Loft/Studio

ValueLocationHeating

4.94 out of 5 average rating, 175 reviews

4.97 out of 5 average rating, 226 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.

Guest house in El Cajon

Mt Helix Studio Loft with Mountain Views

FamilyValueAir conditioning

Guest house in Spring Valley

A warm living area features a comfortable gray sofa facing a modern electric fireplace with colorful artwork displayed above. An open layout connects the space to a well-equipped kitchen, enhanced by natural light streaming through the window and recessed lighting overhead.

Private SD Guesthouse 20 Min to Beaches & Downtown

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4.99 out of 5 average rating, 112 reviews

5.0 out of 5 average rating, 581 reviews

A tranquil koi pond is nestled within a landscaped garden, featuring several colorful koi fish swimming gracefully near the surface. Rocks and plants frame the pond, while a small waterfall cascades gently into the water, creating a soothing ambiance.

Guest house in Hillcrest

Waterhaven - A Pondside Oasis

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Guest house 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.

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

LocationValueHospitality

4.99 out of 5 average rating, 199 reviews

Guest house in Golden Hill

A charming exterior of a boutique guesthouse is presented, featuring a vibrant yellow door and large windows. Lush greenery with various plants and flowers adorns the landscape, while a crafted stone pathway leads to the entrance. A warm, inviting atmosphere is conveyed through well-maintained landscaping.

The Golden Hill mosaic "casita"

LocationFamilyGetting around

4.87 out of 5 average rating, 568 reviews