House holiday rentals in Lakeside

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Top-rated house rentals in Lakeside

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Top guest favourite

A serene view of Lake Cuyamaca is framed by lush greenery and trees. The distant Stonewall Peak rises majestically against a clear blue sky, creating a tranquil landscape that invites relaxation and reflection.

Home in Julian

4.99 out of 5 average rating, 163 reviews

Maison Zen

Nestled high on the hill, this private, cozy mountain sanctuary offers breathtaking views of Lake Cuyamaca and majestic Stonewall Peak. Enter the door of our serene and peaceful zen home and feel your entire body relax in the calming space. The floor-to-ceiling sliding glass doors open to a deck where you can enjoy a morning coffee, an evening glass of wine or a restorative yoga session. Maison Zen is ideal for a couple's getaway or an individual's "escape." Not suitable for children or infants.

Guest favourite

A well-appointed backyard features a heated pool with a waterfall, surrounded by palm trees and lounge chairs. An outdoor dining area is under a covered gazebo, providing a view of the landscaped space. Soft evening light hints at a serene atmosphere.

Home in Spring Valley

4.98 out of 5 average rating, 102 reviews

Tropical Oasis: spa, solar heated pool, waterslide

This home is ideal for FAMILY trips and QUIET friend groups Hours of entertainment in the private backyard that includes heated pool, waterslide, grotto, spa, gazebo, half bath, BBQ, and more. Clean and spacious home with over 2,100 sqft of living space. Minutes from everything San Diego has to offer. Distance to main attractions: SDSU- 5 mi Downtown/PetcoPark park-11 mi SD Zoo/balboa park-12 mi SD Airport- 13 mi Old town- 14 mi Coronado-15 mi Belmont park/Mission beach-18mi Sea world- 18mi

Top guest favourite

A spacious studio features a comfortable queen bed topped with a patterned blanket. Natural light filters in through a nearby window, illuminating the room's neutral tones. A piece of art depicting a tree-lined path hangs above the bed, enhancing the room's calming ambiance.

Home in Lakeside

4.99 out of 5 average rating, 120 reviews

Terra Mesa - Charming Retreat

Welcome to TerraMesa! This charming studio boasts a thoughtfully designed space, blending modern comfort with a touch of rustic elegance. With a fully equipped kitchenette, a plush queen bed, and a stylish sitting area, it’s perfect for couples seeking a romantic getaway or solo travelers exploring the San Diego area. Sip a cup of coffee or glass of wine in your private little patio. Centrally located in scenic Lakeside, you’ll have easy access to downtown, beaches or our local mountain towns.

Top guest favourite

An outdoor seating area features several adirondack chairs arranged around a modern fire pit, where vibrant flames dance above colorful glass stones. Soft illumination from lanterns casts a warm glow, and the backdrop showcases gently rolling hills under a twilight sky.

Home in Lakeside

4.98 out of 5 average rating, 100 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 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?

Guest favourite

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

4.97 out of 5 average rating, 860 reviews

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.

Guest favourite

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, 208 reviews

Bright and spacious home with views, pool & spa.

This beautiful and recently remodeled, open-floor plan home is conveniently located directly across from Cowles Mountain, one of San Diego's most visited hiking trails. Each bedroom has its own full bathroom. Perfectly located for the outdoorsy family. Tons of hiking and mountain bike trails are just across the street. Only 15 min. away from beaches, zoo, & Sea World. Gaslamp/Downtown is only 20 min. by car. After a day of exploring, come home to a newly-built, salt-water pool and spa.

Top guest favourite

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.

Home in La Mesa

4.93 out of 5 average rating, 226 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!

Guest favourite

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.

Home in La Mesa

4.98 out of 5 average rating, 109 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.

Guest favourite

The bathroom features a modern glass shower with black fixtures and a sliding door. Shelves hold complimentary toiletries, while neatly folded towels are arranged above. Natural light enters through a small window, enhancing the clean and functional design of the space.

Home in Teralta East

4.94 out of 5 average rating, 229 reviews

Private Studio

Enjoy a cozy studio all to yourself, just minutes from University Ave, walking distance to shopping and food like Denny's Jamba Juice and Starbucks. Less than 15 min to Gaslamp (Downtownthe San Diego zoo, North Park, the 805, 15, and other great places nearby. This is a unit with a private entrance and black out shades and a gated driveway for security. California King with plush top Serta mattress. check in can be earlier. Please ask PLEASE READ INFO to ensure it's a fit for you.

Top guest favourite

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.

Home in La Mesa

4.98 out of 5 average rating, 284 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

Top guest favourite

A six-person hot tub is set against a backdrop of rolling mountains and valleys, providing expansive views of the landscape. The water is inviting, with bubbles rising gently. The area surrounding the hot tub is accented by natural stones and vegetation, enhancing the serene environment.

Home in Julian

4.99 out of 5 average rating, 160 reviews

Private Getaway - Breathtaking Views

Discover the Julian Ridgetop Retreat, a private haven with breathtaking panoramic views. 🔸Wake to stunning Salton Sea sunrises from your bed 🔸Unwind in the hot tub under starry skies. 🔸Immerse yourself in nature with nearby trails and adventures 🔸Enjoying year-round comfort with central AC/heat. 🔸Explore historic Julian's charms—apple orchards, wineries, and quaint shops—just minutes away. 🔸Book now and receive our exclusive local guide for an unforgettable mountain escape.

Top guest favourite

A comfortable living area features a large sectional sofa with decorative pillows. Natural light streams in through two windows, adorned with dark curtains. A rustic brick fireplace and a low wooden coffee table with magazines add character to the space, enhancing its welcoming ambiance.

Home in Rolando

4.93 out of 5 average rating, 141 reviews

(Relist!) Relax at a Stunning 1931 Historic Tudor!

Come & enjoy our 1931 historic tudor home! Beautifully rebuilt within the last 2 years. This house has a huge front lawn and space to roam. Enjoy the serenity this large property has to offer. Three peaceful patios to enjoy your morning coffee. The kitchen has an 48-inch 1950’s oven for the chef in the family. Bay windows, arched entryways and original light fixtures make this such a charming place to stay. Centrally located to enjoy everything San Diego & La Mesa has to offer.