Guesthouse holiday rentals in Chula Vista

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, 183 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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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, 475 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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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.

Guesthouse in San Diego

Farm Vibe near City with Friendly Goats & Big Deck

Charming home has spacious bedroom (king bed), full bath (tub/shower), living/dining area and stocked kitchen all with stylish touches. Relax and lounge on your back deck while saying hello to the friendly goats. Your lodging is nearby the city where you can have a touch of countryside as well as modern amenities throughout with keyless entry, WiFi and Smart TV (W/D also available). It's a perfect space for a couple, small family or group of friends looking for a bit of it all next to it all!

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4.93 out of 5 average rating, 248 reviews

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, 179 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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Guesthouse in Lemon Grove

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. A spacious island features four high stools arranged for seating, while a large window allows natural light to illuminate the area. Cooking essentials and a coffee maker are visible on the countertop.

STUNNING Casita with a View!!

If you’re reading this, we want to thank you for showing interest in our charming Casita! 🏡 Recently renovated with couples in mind, it’s a cozy, relaxing space perfect for your getaway. Features include: • 🚗 On-property parking • 🍳 Fully furnished kitchen with all appliances • 🧺 Washer and dryer in-home • 💻 High-speed internet • ✨ Clean, modern, comfortable space • 🌄 Breathtaking mountain and valley views We’d love to host you and make your San Diego stay truly memorable!

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4.89 out of 5 average rating, 243 reviews

4.96 out of 5 average rating, 435 reviews

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.

Guesthouse in San Diego

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.

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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.

Trendy 1 BR Guesthouse. Great views, no chores.

This is a beautiful 1 bedroom guest house with a new Queen size bed (4/13/2026)and full-size sofa bed. It is close to everything, making it easy to plan your visit. AirPort, Downtown, Coronado, Balboa Park, local beaches, Mexico, and Navy bases are just a few minutes' drive. Private on-site parking. Charge your EV on site. 110v or 220V Don't waste precious time on charging stations. Public transportation as well as plenty of shopping and restaurants within walking distance.

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4.95 out of 5 average rating, 248 reviews

Guesthouse in National City

Private Pet-Friendly Studio w/Fenced Yard +Parking

Private, pet-friendly studio perfect for couples or travelers with a dog. Enjoy easy parking, a private side-gate entrance, self check-in, and a fenced yard for pets to play safely. The studio is fully separate from the main house for added privacy. Located just 4 miles from the Gaslamp District, with easy access to downtown, Coronado, nearby dog-friendly beaches, restaurants, and bars, it’s a quiet and convenient home base for your San Diego stay.

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4.87 out of 5 average rating, 216 reviews

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

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!

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4.81 out of 5 average rating, 243 reviews

Guesthouse in National City

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.

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4.87 out of 5 average rating, 263 reviews

4.96 out of 5 average rating, 138 reviews

Guesthouse in San Diego

Relax & Unwind – Cozy 1BR | Comfortable Beds!

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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.

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 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.

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4.95 out of 5 average rating, 666 reviews

Popular amenities for Chula Vista guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

5.0 out of 5 average rating, 208 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

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The spacious studio features a modern design with a cozy seating area that includes a dark leather couch and a patterned armchair. A dining table is set for four, and natural light fills the room from large windows. The kitchen showcases sleek cabinets and stainless steel appliances.

4.92 out of 5 average rating, 359 reviews

Private Detached Modern Studio located in La Mesa

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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

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Guesthouse 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

ValueFamilySolo travel

4.97 out of 5 average rating, 224 reviews

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

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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.

The Golden Hill mosaic "casita"

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4.87 out of 5 average rating, 568 reviews

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, 160 reviews

NEW construction - Studio by Village of La Mesa

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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.

Beautiful Historic Home and Gardens Near Downtown!

LocationFamilyCheck-in

4.97 out of 5 average rating, 300 reviews

Guesthouses with a patio

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

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Guesthouse in Bankers Hill - Park West

A bright sleeping area features a spacious bed with soft linens and decorative pillows. Natural light floods the room through two windows adorned with white shutters, while a small seating area is visible through an open door, offering a cozy view of the private deck.

Upper Suite - Walk to Little Italy - AC + Deck

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4.83 out of 5 average rating, 132 reviews

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.

5.0 out of 5 average rating, 113 reviews

Beautiful Bright Mt. Helix Studio

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A modern kitchen is visible, featuring sleek black cabinets and white countertops. Stainless steel appliances, including a gas stove, are present. A small dining area with a black table and checkered tablecloth complements a cozy seating area, illuminated by natural light from large windows.

4.94 out of 5 average rating, 412 reviews

La Mesa Suite

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4.88 out of 5 average rating, 252 reviews

Garden Room- Private Studio with a Panoramic View

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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, 383 reviews

SDCannaBnB #1 *420 *parking *dog-friendly *hot tub

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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.

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

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4.98 out of 5 average rating, 232 reviews

4.98 out of 5 average rating, 113 reviews

Enchanting private Mt Helix retreat close to SDSU

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Guest house rentals with a washing machine and dryer

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, 326 reviews

Hawks nest

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Guesthouse in Golden Hill

A view of downtown San Diego is captured from the balcony, framed by lush palm trees and residential rooftops. City skyscrapers rise in the distance, under a clear blue sky, creating a vibrant urban landscape complemented by greenery.

Golden Hill House, Gorgeous Skyline, Private Patio

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4.89 out of 5 average rating, 487 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.

4.96 out of 5 average rating, 231 reviews

Cozy Coop with a View

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4.98 out of 5 average rating, 115 reviews

The vibrant sunset sky is filled with hues of pink, orange, and purple, reflecting beautifully in the calm water of the pool. Palm trees stand in silhouette, framing the picturesque view of the surrounding mountains and valleys.

Guesthouse in Jamul

San Diego Mountain Retreat

LocationFamilyHospitality

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.

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

LocationFamilyCheck-in

4.99 out of 5 average rating, 199 reviews

Guesthouse in Greater North Park

The bedroom features a upholstered headboard and is accented by warm bedside lamps. A large photograph of a pier over water hangs above the bed, while blue and white decorative pillows add contrasting color. A cozy quilt covers the spacious bed.

Enjoy North Park at Comfy & Chic Bungalow Retreat

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4.94 out of 5 average rating, 328 reviews

Guesthouse in Normal Heights

The “OUT” House: Artist’s Loft/Studio

ValueFamilyBarbecue

4.94 out of 5 average rating, 175 reviews

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.