House holiday rentals in Lakeside

4.9 out of 5 average rating, 288 reviews

A private yard showcases a small seating area with blue chairs under a large umbrella. Colorful flower beds line the space, with vibrant pink bougainvillea blooming nearby. Circular stepping stones lead through the natural ground, enhancing the outdoor setting.

Home in Emerald Hills

Snazzy Spot with yard near beaches and downtown

Welcome to this modern get-away that is as bright and cheerful as a sunny day! You'll be sure to be rejuvenated here after your trips to the nearest beach (only a 15 minute drive) and outings on the town (only 10 minutes by car to downtown). This spot includes a private parking spot and a private yard. Yours to enjoy are a very comfortable queen bed, TV in bedroom, Fast WiFi, and a well stocked kitchenette. There are also two canyon hikes within a 2 minute walk with views of downtown for sunset.

4.97 out of 5 average rating, 310 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!

4.99 out of 5 average rating, 395 reviews

The interior space features a cozy living area with a soft gray sofa, warm wood accents, and natural light flowing in through large windows. A staircase leads to the upper level, where the tree-themed wall art adds character. A dining table is positioned near the double French doors.

Home in Golden Hill

Golden Hill Tree House

The Golden Hill Tree House is an urban oasis hiding in the branches of two mature trees in the heart of San Diego. While you enjoy elevated privacy you can also treat yourself to a soaker tub with double shower heads or settle down in a cozy reading nook to enjoy a good book! You'll also be walking distance to some amazing restaurants and super close to the best of San Diego, including downtown, the beach and the zoo! It's a perfect place to recharge after a long day of business or pleasure!

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, 112 reviews

SD Casita Sleeps 6 - Morey from 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 many amenities including a GE electric cooktop, refrigerator, microwave and air fryer, rice cooker, Kitchenaid mixer, 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 sofabed. How about a large deck with fire pit and BBQ?

4.97 out of 5 average rating, 879 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.

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, 233 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.

4.98 out of 5 average rating, 116 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, 300 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

A spacious outdoor area features a swimming pool, accompanied by colorful lounge chairs and a large umbrella for shade. A unicorn float is visible in the water, with potted flowers adding a touch of vibrancy. The home's façade offers multiple windows and seating options nearby.

4.99 out of 5 average rating, 183 reviews

Mid-Century Style Family House with Spa

Beautiful Mt. Helix mid-century modern family home with incredible views, designed by architect of original Las Vegas, Desert Inn 3/4 acre.Less than 20 minute drive to beaches/Zoo/Sea World/Downtown, . With a swimming pool/hot tub, whole House have AC to. surrounded by California Oak/orange/lemonpomegranate trees and herb garden this home is the epitome of 1950’s luxury. A perfect family oasis, you won’t even want to leave the property. No loud parties please, this is a quite community.

5 out of 5 average rating, 106 reviews

Home in Rolando

Peaceful Casita | Firepit • Near SDSU

Welcome to our cozy home, perfect for couples visiting the area. It's also a great spot for SDSU parents visiting their kids. Conveniently close to the campus but far enough to enjoy some peace and quiet. If you enjoy this listing, click the heart icon ❤ in the top-right corner to bookmark it for easy access! Minutes from key attractions: ★ 6 min to SDSU/Viejas Arena ★ 14 min to Balboa Park ★ 17 min to Downtown SD (Gaslamp) ★ 19 min to San Diego Zoo ★ 21 min to the Airport

4.96 out of 5 average rating, 136 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!

4.91 out of 5 average rating, 363 reviews

An open living area features a large wooden dining table surrounded by six white chairs. A cozy sofa, adorned with neutral pillows and a blanket, overlooks expansive glass windows showcasing hillside views. A Christmas tree stands in the corner, adding a festive touch.

Home in Bonita

Glass Home with Views, Hot Tub, FREE EV Charging!

Update: We just installed a level 2 EV charger and are giving away free EV charging to the next 5 guests! Our modern, light-filled, scandinavian inspired home is a beautiful place to rest while you enjoy the magic of San Diego. The entire front of our home is glass with breathtaking views over the mountains and reservoir below. Neutral decor and warm wood accents provide a relaxing atmosphere and a tranquil setting.

Popular amenities for Lakeside house rentals

Kitchen

Wi-Fi

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, 192 reviews

The Queen House

4.99 out of 5 average rating, 194 reviews

A serene backyard is framed by colorful sunset skies, featuring a cozy hammock in the foreground and a comfortable seating area with grey couches. String lights add warmth to the outdoor space, complemented by lush greenery throughout the neatly landscaped yard.

Home in La Jolla

La Jolla Beach House-Family Focused-3min to Beach

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, 211 reviews

Bright and spacious home with views, pool & spa.

4.82 out of 5 average rating, 126 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

4.99 out of 5 average rating, 171 reviews

A bright living space features a warm wooden ceiling and large windows. A comfortable orange sofa is paired with a wooden coffee table on a patterned area rug. The kitchen, visible in the background, includes modern appliances and white cabinetry, enhancing the cozy atmosphere.

Home in Hillcrest

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool

A scenic hillside is displayed, featuring a variety of homes nestled among lush greenery. The landscape showcases a blend of residential architecture within a mountainous region, with expansive views of the surrounding area under a clear blue sky.

4.93 out of 5 average rating, 124 reviews

Updated TownHome, Great Location, Fantastic Views

Home in San Pasqual Valley

An outdoor seating area is equipped with comfortable chairs surrounding a modern fire pit, where flames flicker gently. The pool glistens nearby, framed by lush landscaping and a serene hillside, with a light hue of sunset in the background.

4.95 out of 5 average rating, 152 reviews

Stunning 3 bedroom w/Views! Game Room/Pool/Hot Tub

4.96 out of 5 average rating, 110 reviews

A serene backyard oasis features a small spa surrounded by lush greenery and decorative plants. The space is framed by an open wooden structure with a sloped roof, providing a cozy seating area with soft cushions. Unique pendant lights hang above, adding a touch of elegance.

Home in Normal Heights

Luxe Home w. Serene Backyard Spa

Weekly house rentals

5 out of 5 average rating, 18 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

4.98 out of 5 average rating, 92 reviews

The exterior of a single-family home is showcased, featuring a spacious driveway and a two-car garage. Mature cacti and landscaped greenery enhance the front yard, while a clear blue sky provides a bright background.

Home in Santee

Santee Gem: Luxe Modern Home, Spacious Backyard

5 out of 5 average rating, 35 reviews

Farmhouse on Sunny Outdoor Dining area 20min to SD

4.97 out of 5 average rating, 69 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!

5 out of 5 average rating, 11 reviews

Helix Haven

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.

4.86 out of 5 average rating, 22 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, 25 reviews

Studio In Home with Private Entry

5 out of 5 average rating, 94 reviews

Home in Los Olivos

Quiet Country Home

Private house rentals

5 out of 5 average rating, 15 reviews

Airbnb Luxe: Designer Pool, Fitness and Office

4.94 out of 5 average rating, 32 reviews

A breathtaking sunset view showcases vibrant orange and pink hues filling the sky above rolling hills. The scene includes an outdoor deck area with a dining table and chairs, framed by expansive glass doors, inviting the beauty of nature indoors.

Home in Spring Valley

Serenity in San Diego

Superhost

A modern home is showcased with a clear blue heated pool reflecting the evening sky. The pool area is bordered by sleek stone and features a welcoming outdoor seating area. Lush greenery frames the property, enhancing the serene atmosphere of the neighborhood.

4.71 out of 5 average rating, 82 reviews

Peaceful Modern 8 Bed Home With Pool

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, 54 reviews

Discover La Mesa: Your Perfect Cozy Base

A saltwater pool with a built-in spa is framed by a stone patio, offering an inviting space for relaxation. Adjacent to the pool, a covered outdoor bar area with a grill and seating is visible, surrounded by lush greenery.

4.97 out of 5 average rating, 72 reviews

The Pool House

Superhost

An open living space is depicted, featuring a light-colored sofa adorned with decorative cushions. A patterned area rug lies on the hardwood floor, with a modern coffee table placed centrally. A flat-screen TV is mounted on the wall, while a dining area can be seen in the background.

4.73 out of 5 average rating, 56 reviews

Serene Lakeside Getaway-Sleeps 8

5 out of 5 average rating, 13 reviews

A sunlit bedroom features a spacious queen bed adorned with decorative bedding and a light throw. A minimalist bench sits at the foot of the bed, while a desk and lamp occupy a corner. Windows provide natural light, illuminating the soft-toned walls.

Home in El Cajon

Cozy quiet getaway, great mattress (1-br)