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, 178 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

LocationValueSleep quality

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, 153 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

FamilyValueCondition

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, 469 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!

FamilyLocationQuiet

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, 129 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!

ValueLocationCondition

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, 174 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.

FamilyValueCleanliness

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.

FamilyLocationBeach

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.

4.96 out of 5 average rating, 228 reviews

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.

FamilyValueLaundry

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, 376 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

FamilyLocationWi-Fi

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, 113 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.

FamilyLocationCondition

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, 235 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.

ValueLocationCleanliness

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, 108 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.

LocationFamilySleep quality

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, 301 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.

FamilyValueCondition

Popular amenities for La Mesa guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

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, 276 reviews

Fig Tree Bungalow

ValueLocationAccuracy

5 out of 5 average rating, 203 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

FamilyValueIndoor spaces

4.99 out of 5 average rating, 112 reviews

AmazingVIEWS! Hilltop Guest House with XL Balcony~

LocationValueAccess

5 out of 5 average rating, 429 reviews

Private Poolside Cabana

ValueFamilyLaundry

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, 263 reviews

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

LocationValueBarbecue

Guesthouse in Spring Valley

4.98 out of 5 average rating, 442 reviews

Airstream•Sauna•SoakTub• Views•Firepit+Zoo add-on

ValueFamilyAccess

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, 186 reviews

Granny Flat with Bedroom/Bathroom/Kitchen

ValueLocationOutdoor spaces

Superhost

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.

4.84 out of 5 average rating, 173 reviews

Cozy Casita

FamilyValueSleep quality

Guesthouses with a patio

4.98 out of 5 average rating, 133 reviews

Guesthouse in Bonita

Adorable 1- bedroom guesthouse/Casita

LocationFamilyPool

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.

4.95 out of 5 average rating, 121 reviews

Beach views for 2! Jacuzzi, fire pit

LocationFamilyLong stay

4.96 out of 5 average rating, 171 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

ValueFamilyKitchen

Superhost

A well-lit bedroom features a spacious bed adorned with blue decorative pillows. A television is mounted on the wall opposite, with a dresser below. A window allows natural light to enter, and a plant is placed on the dresser near the window, enhancing the room's decor.

Guesthouse in Bonita

4.75 out of 5 average rating, 106 reviews

Great Location Conveniently Located to All

LocationValueDecor

Guesthouse in Sunset Cliffs

A scenic view of the ocean is visible from a balcony. Lush greenery and palm trees frame the coastline, while rooftops and solar panels from nearby homes are seen below. The clear blue sky reflects the tranquil ambiance of the surroundings.

4.97 out of 5 average rating, 119 reviews

Guest house with ocean views and private deck.

FamilyValueCheck-in

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, 103 reviews

Cozy Hillside Retreat with View

FamilyValueView

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, 230 reviews

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

FamilyValueAmenities

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, 136 reviews

Violet Oasis | hot tub + kitchen

LocationFamilyBathroom

Guest house rentals with a washing machine and dryer

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, 428 reviews

*BEAUTIFUL* Sunny Home in Golden Hill

LocationFamilyLayout

Guesthouse in Mission Beach

The living area features natural wood paneling and a warm color palette. Large windows allow ample light, framed by woven shades. A comfortable white sofa and a stylish entertainment unit with a television are visible, along with a decorative chair and a small side table.

4.91 out of 5 average rating, 852 reviews

South Mission Beach Zen-Like Studio

FamilyLocationAmenities

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, 228 reviews

Modern mountain guest house. Incredible views

ValueFamilyAccess

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, 254 reviews

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

LocationValueIndoor spaces

4.92 out of 5 average rating, 106 reviews

A modern kitchen and living area features comfortable seating with a yellow sofa across from a rustic wooden coffee table. Barstool seating is available at an island, with kitchen appliances and decorative artwork adorning the walls, creating a cozy and functional space.

Guesthouse in Bay Park

Casa de Estilo - Rooftop Views and Tranquility

FamilyValueBeach

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, 218 reviews

Mt Helix Studio Loft with Mountain Views

LocationFamilyLong stay

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, 299 reviews

Beautiful Historic Home and Gardens Near Downtown!

FamilyValueKitchen