House holiday rentals in Lakeside

4.99 out of 5 average rating, 211 reviews

An aerial view of Zen House reveals a glass solarium and inviting outdoor spaces illuminated by soft lighting. The lush garden features various plants and cozy seating. A sleek dining area is visible, all set against the backdrop of distant city lights and a twilight sky.

Home in Chula Vista

Zen Retreat with Solarium & Spa Tub

A Zen-like Airbnb, combining Haute Design with Leisure and Resort amenities. Self Managed : details matter. Distant Ocean View. Close to SD landmarks; within a quiet neighborhood surrounded by canyons & parks. A blissful escape. A design that provokes a unique experience; Interior-sparkling clean. Each room unique to allow you to relax in the moment. A 2nd floor solarium offers amazing views; soak in the jacuzzi tub in an exquisite bathroom; a boutique kitchen & dining open to a sensory garden.

4.97 out of 5 average rating, 314 reviews

Home in Ramona

Wine Country Retreat - Tranquility Hottub/Views

Our famed Wine Country Retreat is back online! (LTR for the last year) Take the back roads scenic drive 50mins up the hill from San Diego and enjoy some much needed quiet and comfy tranquility. Right in the heart of San Diego Wine Country, it’s a rather well appointed place situated on 10 private acres that overlooks expansive green space. With few neighbors in any direction, you can either sleep with the windows open and wake early to roosters crowing, or close the windows and sleep til Noon!

A contemporary casita is set against a vibrant sunset, showcasing large windows that reflect the warm colors of the sky. The entrance features a clear path leading to a well-lit doorway, surrounded by natural landscaping and scenic hillside views.

4.94 out of 5 average rating, 119 reviews

San Diego Casita for 6 Morey de Prieto Surf Ranch

The Morey de Prieto Surf Ranch is truly awesome! Reserve your stay in this 2 Bed/1 Bath 650 sq. ft. casita for six. Home includes a kitchen with a GE electric cooktop, refrigerator, microwave/air fryer, rice cooker, mixer for drinks, sink with prep trays, Moen faucet fixtures, gorgeous shower, Krups coffee maker, 50" smart TV equipped with WiFi and NetFlix, mountain views, workspace and a sofa bed. Relax on the large 240 sq. ft. private deck featuring a fire pit, adirondack chairs and BBQ.

A spacious living area features a large leather sectional sofa positioned around a circular wooden coffee table. A wall-mounted TV is visible above a decorative fireplace, while natural light streams through a large window adorned with sheer curtains. A dining area is seen in the background.

4.87 out of 5 average rating, 111 reviews

Sunny & Spacious 3BR Retreat w/ Parking & A/C

Centrally located in La Mesa is this newly refurbished home ideal for business or pleasure with all of life’s little luxuries waiting for you to enjoy. The home features open concept living with a gourmet kitchen, a chic dining space, 3 beautiful bedrooms, 2 modern bathrooms and an expansive yard with an outdoor lounge. Walk 10 mins to Grossman Center with a Target, restaurants, cafes, a cinema & Walmart or drive to the heart of San Diego and all its attractions just 20 mins from your door.

4.97 out of 5 average rating, 887 reviews

An open-concept living area is highlighted by high ceilings and large windows, offering natural light. A modern kitchen features wood cabinets and a white island, while a dining table with turquoise chairs accommodates several guests. A cozy seating area is visible in the background.

Home in Ramona

The Glass House - A Nature Retreat

Enjoy a unique retreat; 180 degrees of views from inside the home. Nestled at the end of a private road, our place is nearby great hiking and countryside wineries. The Glass House provides a magical space and nature retreat where individuals, couples, families and friends can gather together to re-connect with nature, each other, and themselves. The breathtaking mountain top views, the huge deck, hot tub, fireplace, and the open concept living space is unbeatable for the perfect getaway.

4.96 out of 5 average rating, 105 reviews

A spacious studio features a purple sofa and a queen bed, both adorned with soft blankets and decorative pillows. Vibrant area rugs cover the wooden floor. Natural light floods the room through glass doors, leading to a private patio surrounded by greenery.

Home in San Diego

XLarge Artist's Retreat w/private patio/parking

*Forget your worries in this beautiful 700sq/ft spacious and serene space. *Come soak up in the artsy feel of this newly renovated large guest suite, ideally located in the middle of town close to SDSU. Roll out of bed and Enjoy a cup of coffee in the private patio then explore ALL of the city’s top attractions a short drive away. This beautiful space is clean, crisp and fully decorated with great style uniquely curated with original art by one of SD’s most established artists. * Enjoy*

The kitchen area features modern black cabinetry and stainless steel appliances, including a microwave and compact refrigerator. A smart TV is mounted on the wall, complementing the wooden counter workspace equipped with essential cooking utensils. A dining table with two chairs is positioned nearby.

4.85 out of 5 average rating, 247 reviews

Newer "Manor Studio"

Centrally located in San Diego County this newer studio style unit has a private entrance, private patio area and street parking. Furnished with a queen size bed, love seat, full bathroom and kitchen area. One large drawer to accommodate personal items, and a wall rack to hang clothing. There is a smart TV with WiFi streaming capabilities and lots of USB plugs to charge your devices. On street parking in front of unit (no parking in driveway). No Pets allowed. No Hair Dying allowed.

A view into a modern living space reveals a sleek kitchen with bar seating and a spacious dining area. Natural light floods the room through large glass doors, showcasing lush greenery outside. A cozy area is completed with a colorful rug beneath and a inviting seating arrangement.

4.94 out of 5 average rating, 234 reviews

Cottage in the Garden! New! Modern!

COTTAGE IN THE GARDEN - New! Modern! Find beauty and serenity in this special guest house in one of San Diego's most desirable areas! Flowering bushes, plants, olive tree and fruit trees seen from all windows. All amenities: WiFi, Cable, serving dishes and tableware, full coffee bar, Ninja Blender, Flat screen TVs, 100% Egyptian Cotton Sheets or Boll and Branch Sheets (used by 3 Presidents), Japanese Toilette and more. 15 minutes to Downtown San Diego and 20 minutes to the beach!

A welcoming living area features a spacious beige sectional sofa adorned with patterned throw pillows. Natural light filters through a large window, complemented by soft, flowing curtains. A dark ottoman with decorative details adds a contrasting element to the cozy space.

4.97 out of 5 average rating, 119 reviews

Zen Retreat: 3-Bedroom Oasis near La Mesa Village

Relax in this charming 3-bedroom, 1-bathroom home located just 1 mile from the heart of Historic Downtown La Mesa Village. Nestled in a quiet, central neighborhood, this cozy retreat offers easy access to major freeways, top-rated restaurants, and the local trolley line making it a breeze to explore the best of San Diego. Within 10 to 15 miles, you’ll find yourself in iconic destinations like Downtown San Diego, Balboa Park, Coronado Island, scenic beaches, and beautiful mountain trails.

A colorful studio space features turquoise walls and a ceiling fan. A comfortable sofa with decorative pillows is paired with a coffee table. A bed with a floral-patterned comforter sits against a window, while a TV and white refrigerator complete the modern setup.

4.98 out of 5 average rating, 306 reviews

SDCannaBnB #2 *420 *parking *dog-friendly *hot tub

Welcome to SDCannaBnB - San Diego's premier cannabis-friendly rental! Our studio is newly remodeled with luxury ammenities. We proudly cater to the cannabis community and non-users alike. Our studio 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 studio is located in our quiet, fully fenced in backyard, close to San Diego's attractions

4.96 out of 5 average rating, 141 reviews

The inviting entrance features a covered porch adorned with a vibrant yellow door. Succulents and greenery enhance the landscape, complemented by a palm tree nearby. The porch area includes seating, providing a welcoming atmosphere for relaxation.

Home in San Diego

The Cozy Craftsman

Escape to this serene, stylish retreat. Built in 1935, this Craftsman-style home exudes timeless San Diego charm. Perfectly situated in University Heights, bordering Hillcrest and North Park, you’ll be close to restaurants, cafés, grocery stores, public transportation, the San Diego Zoo, and Balboa Park. This 650 sq ft home has been renovated inside and out, and equipped with everything you need for a comfortable stay!

4.98 out of 5 average rating, 487 reviews

Home in Encinitas

Lux Casita with Pickleball & Resort Amenities

Escape to this inviting Casita, where bright white walls and French doors fill each room with light and warmth. Thoughtfully furnished and full of charm, it offers a serene retreat with private resort-style amenities, including a tennis court, pool, and lush gardens. Step outside to hiking and biking trails, then return to cozy comfort. An optional second suite provides extra space for a relaxed, luxurious stay.

Popular amenities for house rentals in Lakeside

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A view of the inviting swimming pool surrounded by a spacious patio. Natural rock elements and vibrant landscaping enhance the outdoor area. The multi-level deck is visible, offering seating options and picturesque canyon surroundings under a clear blue sky.

4.89 out of 5 average rating, 196 reviews

The Queen House

Home in University Heights

A well-lit bedroom features a spacious bed with neutral bedding and striped pillows. Natural light enters through glass doors leading to a semi-private patio. A textured area rug and a potted plant add subtle warmth to the wood flooring.

4.86 out of 5 average rating, 100 reviews

Cozy University Heights Cottage

4.86 out of 5 average rating, 103 reviews

Entertainers Dream Pool Home

A spacious outdoor area features a clear blue pool surrounded by palm trees. Lounge chairs are positioned nearby, and a shaded table with chairs offers a spot for relaxation. The backyard showcases a privacy fence and ample sunlight.

4.85 out of 5 average rating, 232 reviews

San Diego Pool | Fire Pit | Sunshine | Sleeps 10

4.85 out of 5 average rating, 103 reviews

The private pool area is surrounded by palm trees and cacti, with lounge chairs positioned for relaxation. A shaded dining area is visible in the background, complemented by the warm glow of a sunset sky. The scene creates a serene outdoor retreat.

Home in San Diego

Surf Cottage w/Pool & Firepit 10min from the beach

4.99 out of 5 average rating, 115 reviews

Home in Escondido

Mountain Top Getaway w/ Pool & Hot tub

Superhost

A serene outdoor space features a salt-water pool surrounded by a concrete patio and manicured grass. An umbrella provides shade over the poolside area, with lush greenery and mountains visible in the background under a partly cloudy sky.

Home in Lake Murray

4.88 out of 5 average rating, 215 reviews

Bright and spacious home with views, pool & spa.

4.81 out of 5 average rating, 128 reviews

The outdoor area showcases a clear pool surrounded by a spacious patio. Lounge chairs, a poolside table, and an umbrella are positioned for relaxation. The backdrop features low landscaping with cacti and a glimpse of the house, enhancing the tranquil setting.

Home in Lake Murray

Mid-Century Modern and Contemporary House

Weekly house rentals

5 out of 5 average rating, 26 reviews

A cozy outdoor seating area features two white Adirondack chairs positioned beside a small round table. The inviting entryway of the tiny home is visible, surrounded by lush greenery and trees, creating a peaceful and refreshing environment.

Home in Rolando

Tiny Home with a View

Superhost

An outdoor gazebo is surrounded by lush greenery, with comfortable seating comprising wooden chairs and a central table. Soft curtains provide privacy. Artificial grass covers the ground, enhancing the space's appeal. Bright sunlight creates a warm environment, perfect for relaxation.

Home in Teralta East

4.86 out of 5 average rating, 77 reviews

Cozy San Diego Home

5 out of 5 average rating, 36 reviews

Farmhouse on Sunny Outdoor Dining area 20min to SD

5 out of 5 average rating, 16 reviews

Lakeside Deluxe 1-Bedroom

Superhost

The living area is accented with wooden beams and features a cozy sofa, an armchair, and a round wooden coffee table. Natural light fills the room through a window, with a piece of abstract artwork displayed on the wall, enhancing the inviting space.

4.88 out of 5 average rating, 25 reviews

Lakeside Haven | Mountain Views, Private Pool

A private deck features a small round table surrounded by two blue chairs, situated under a palm tree. The view includes rolling hills and a clear blue sky with scattered clouds, offering a peaceful outdoor space to enjoy the scenery.

4.96 out of 5 average rating, 27 reviews

Studio In Home with Private Entry

5 out of 5 average rating, 98 reviews

Home in Los Olivos

Quiet Country Home

5 out of 5 average rating, 22 reviews

A bright living area is furnished with a spacious gray sectional sofa, complemented by a wooden coffee table. A dining area with high stools is visible in the background, while a well-equipped kitchen showcases neutral cabinetry. Natural light fills the room, enhancing its open feel.

Home in South Park

South Park Gem with Amazing Canyon Views!

Private house rentals

5 out of 5 average rating, 29 reviews

Home in El Cajon

Full Home sleeps 8 with Spa and Views

4.79 out of 5 average rating, 24 reviews

Home in El Cajon

The Manor Cottage

The living room is furnished with a comfortable loveseat and a coffee table, complemented by a white TV stand supporting a large smart TV. Decorative plants and slender white branches enhance the ambiance, while soft lighting is provided by a standing lamp. Framed artwork adorns the walls.

4.98 out of 5 average rating, 60 reviews

Discover La Mesa: Your Perfect Cozy Base

4.95 out of 5 average rating, 19 reviews

Helix Haven

4.97 out of 5 average rating, 78 reviews

A serene pool area is framed by vibrant green foliage and terracotta walls, with lounge chairs positioned nearby. Majestic mountains rise in the background under a clear blue sky. A shaded picnic table is visible, inviting relaxation in a tranquil outdoor setting.

Home in Jamul

Jamul Hacienda | Couples Retreat | Pool & Views!

4.93 out of 5 average rating, 100 reviews

A charming exterior of a single-story home is showcased, surrounded by lush palm trees and vibrant landscaping. The front entrance features a round window and an archway, while the driveway is paved, offering easy access to the front door.

Home in Linda Vista

Guest Room with Beautiful Views

4.88 out of 5 average rating, 8 reviews

*New La Mesa Escape – Private Studio

The front entrance of the house features a covered porch with a wooden deck. Two outdoor chairs are situated on the left side, alongside vibrant plants and flowers. The door is flanked by modern light fixtures, and a large window provides a view of the surrounding greenery.