Guesthouse holiday rentals in Chula Vista

The exterior of a rustic stone cottage is framed by lush greenery and colorful plants. A seating area with chairs overlooks the surrounding garden and distant skyline. Sunlight illuminates the natural stone, highlighting the texture and structure of the cottage.

4.9 out of 5 average rating, 442 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.

4.97 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!

A cozy bedroom is highlighted by a spacious bed adorned with a bright yellow knit blanket. Framed photographs of palm trees and cityscapes decorate the walls, while bedside lamps provide soft illumination on either side of the bed.

4.95 out of 5 average rating, 232 reviews

Central Guest House with Private yard

Enjoy a private, fully equipped guesthouse for two in central San Diego — professionally cleaned, thoughtfully hosted & designed for a comfortable stay. Full kitchen, washer/dryer, filtered RO water & a fenced backyard with ambient lighting. Keyless entry keeps arrival simple & secure. Quick access to freeways. Within 15 minutes of the airport, Gaslamp District, Balboa Park, the Zoo, Petco Park, Seaport Village, the Convention Center, and beaches; tucked into a quiet residential neighborhood…

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.

Guesthouse in Chula Vista

The bathroom features a modern design with double sinks set within a marble countertop. Two round mirrors reflect the sleek fixtures. A decorative box holds tissues, while a wall-mounted towel rack and a shower curtain can be seen in the background.

4.85 out of 5 average rating, 124 reviews

King Bed Studio in Chula Vista

Prime location in Chula Vista! Less than 2 miles away from the Gaylord Pacific Resort (10 min drive). Just a 20 min drive to most San Diego hot spots. Private studio with very comfortable king bed. Queen air mattress also available in unit. Modern bathroom with double-sink, standing shower, marble tile countertops. Spacious layout, a dedicated workstation and fast wifi. Prep your morning coffee and simple breakfast in the kitchenette. The mini fridge can store your favorite drinks.

A covered patio features a table and four chairs, providing a shaded space for relaxation. Lush greenery is visible in the background, and a serene sunset glow illuminates the area, enhancing the tranquil atmosphere.

4.95 out of 5 average rating, 114 reviews

Secluded Guesthouse in Central San Diego

Very private guesthouse w/ full kitchen and bathroom. Quiet space perfect for anyone who wants to work or relax in the heart of San Diego. Plenty of FREE on-street parking. Location ⁃ 5 min to 94 and 805 freeways ⁃ 10 min from Downtown ⁃ 15 min from beaches and SeaWorld ⁃ 10 min walk to trolley ⁃ Restaurants/supermarkets within walking distance Amenities ⁃ Brand new mini-splits ⁃ Smart TV w/ Roku (BYOP) ⁃ Queen bed - Tempur-Pedic ⁃ Full kitchen ⁃ Air purifier ⁃ Free on-site laundry

An outdoor dining area features a large wooden table set with decorative dishes and neatly folded napkins. An umbrella provides shade above the table. Surrounding greenery and hanging hammocks create a tranquil atmosphere, while a pergola frames the space, enhancing the inviting outdoor setting.

4.96 out of 5 average rating, 419 reviews

Betty- Guesthouse near CBX & San Ysidro border

This comfy studio located in San Diego is the perfect spot for a quiet & cozy weekend retreat. Inside is bright & inviting with stylish spacious studio, private entrance from side gate, private patio with bbq & hanging hammocks; driveway parking spot & plenty of street parking! The view from the patio is very relaxing, making it the perfect weekend get away. Centrally located in a quiet & peaceful area within 5 minutes away from Plaza Las Americas & 10 minutes away from the CBX.

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.

Guesthouse in Chula Vista

A cozy studio space is highlighted by a daybed adorned with a decorative headboard and intricate bedding. A round table with two chairs offers a dining area, while a potted plant adds a touch of greenery. Natural light illuminates the room through nearby doors.

4.88 out of 5 average rating, 153 reviews

Bayside Boho Casita

Large open concept guest suite is equipped with a wet bar, mini-fridge, private bath and shower. French doors leading you to a private deck within small picket gated area. West facing room is perfect for enjoying your morning coffee and cool bay breeze. We are one block from the bay, trolley, mall, restaurants, and highway. About a 5 minute drive to the Gaylord Hotel and Convention Center The suite is privately attached to the front house also a vacation rental.

Superhost

A clean, modern studio features a spacious bed with light blue and white striped bedding. A kitchenette with a microwave and electric burners is equipped with essential utensils. Large sliding glass doors provide access to a private deck, allowing natural light to fill the room.

Guesthouse in Bonita

4.82 out of 5 average rating, 230 reviews

Private Modern Studio with Ocean View

Newly remodeled clean, bright, and modern private entrance studio with beautiful view of the ocean and downtown from your room. Brand new sliding glass door opening up to a newly built 240 square foot private deck attached to the studio to enjoy breakfast in the morning and sunsets in the evening. Imagine relaxing while having wonderful conversation on your ocean view deck! Just 15 minutes away from downtown San Diego and the beach!

Guesthouse in Chula Vista

The exterior of a two-story building is surrounded by lush tropical plants, including tall palms and vibrant greenery. A paved walkway leads to a private entrance, which is framed by a low wall and several ornamental plants, creating an inviting and serene environment.

4.95 out of 5 average rating, 644 reviews

Private Casita in Great Eastlake Neighborhood

This room is a "casita" (seperate living space) away from the house. It has a private entrance with a cypher lock on the door. The room has new carpet, new tile, and queen size bed. The Eastlake neighborhood is very safe and very quiet. We are located about 20 mins from the beach, downtown San Diego, and San Diego international airport. This location is only 2 miles from the Otay Ranch Mall.

Guesthouse in National City

A spacious living area features light brown walls and hardwood flooring. A mounted television is displayed on one wall, accompanied by a small coffee table. A dining table with wooden chairs is situated near a window, which is dressed in sheer curtains allowing natural light to filter in.

4.87 out of 5 average rating, 246 reviews

Open concept Guesthouse w/private entrance

Welcome Travelers! We’re thrilled to host fellow Airbnb guests, especially those who love to travel as much as we do. My husband and I have had amazing experiences with Airbnb around the world, and now we're excited to share the beauty of San Diego with you! A few things to note: We live on the property in a completely separate unit with our dog and five chickens.

Popular amenities for Chula Vista guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

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

4.99 out of 5 average rating, 189 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 near SDSU!

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

Guesthouse in Spring Valley

4.98 out of 5 average rating, 427 reviews

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

A cozy living area is presented with a plush couch and a reading chair, accompanied by a coffee table. A cushioned bed rests within an alcove, framed by soft curtains. Natural light filters through nearby windows, illuminating the warm wooden flooring.

4.91 out of 5 average rating, 656 reviews

Quaint Craftsman#2- Walkable, Parking, EV Charging

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.

4.96 out of 5 average rating, 110 reviews

Guest house with ocean views and private deck.

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, 133 reviews

NEW construction - Studio by Village of La Mesa

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, 313 reviews

Hawks nest

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, 254 reviews

Santorini-Inspired Cottage w/ Hot Tub + Views

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

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.

4.96 out of 5 average rating, 160 reviews

SDSU Central Cozy Casita | Fast WiFi | Walkable

Superhost

A living area features a cozy orange sofa adorned with colorful pillows. A desk with a green chair is situated near a window covered with vertical blinds, allowing natural light to illuminate the space. An air conditioning unit is mounted on the wall.

4.93 out of 5 average rating, 148 reviews

*KING BED* Colorful Guesthouse by Downtown

Superhost

Guesthouse in City Heights

4.85 out of 5 average rating, 337 reviews

Heart of SD | Zoo Nearby | Private Patio | Central

4.87 out of 5 average rating, 228 reviews

Private Studio with a Panoramic View

4.91 out of 5 average rating, 106 reviews

A spacious private patio features a tiled floor and comfortable seating around a square table. Potted cacti adorn the edges, while the sunset casts a vibrant pink and purple hue over the surrounding hills and valleys, creating a serene backdrop.

Guesthouse in El Cajon

Hilltop Casita Mount Helix

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)

Guest house rentals with a washing machine and dryer

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, 191 reviews

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

Guesthouse in Pacific Beach

The open living area features a modern dining table with four white chairs, accompanied by a small black side table. Light wood tile flooring creates a warm atmosphere. Large windows provide natural light and a view of the outdoors, while soft curtains frame the space.

4.98 out of 5 average rating, 338 reviews

Charming Modern Apartment with private terrace

Guesthouse 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.

4.86 out of 5 average rating, 547 reviews

The Golden Hill mosaic "casita"

4.97 out of 5 average rating, 204 reviews

Guesthouse in Hillcrest

Luxury Studio W/ Garden View in Heart of Hilcrest

A spacious bedroom features a king bed with neutral bedding and decorative pillows. French doors provide natural light and open to a balcony overlooking lush greenery. A modern ceiling fan and soft lighting complement the hardwood floor and simple decor, creating a comfortable and inviting space.

4.96 out of 5 average rating, 216 reviews

New Guest House - North Park

Guesthouse in City Heights

4.96 out of 5 average rating, 456 reviews

Central San Diego! Your home away from home!

A sunset is captured shining through trees, casting rays of light over the guest house. The structure features large windows, allowing natural light to fill the space. Palm trees and distant silhouettes of buildings are visible against the colorful sky.

4.95 out of 5 average rating, 648 reviews

Early 1900's Carriage House w/Views