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Holiday rentals in Lakeside

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Top-rated holiday rentals in Lakeside

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Top guest favourite
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.
Guest house in La Mesa
4.99 out of 5 average rating, 134 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

Top guest favourite
A welcoming entrance features a textured walkway leading to a front door, framed by a wooden railing. Colorful flowers bloom along the sloped landscape, enhancing the natural appeal of the surroundings. Clear skies and distant homes provide a serene backdrop.
Guest house in El Cajon
4.99 out of 5 average rating, 203 reviews

Modern mountain guest house. Incredible views

Neighboring San Diego, quaint country living with incredible views minutes from everything, breathtaking sunsets, 20 mins to beach, close by hiking trails, and only 3 minutes hop on the freeway. Full Kitchen, Laundry, and Living area and with beautiful furnishings, a perfect home away from home. Whether traveling for work or play we have had guests stay for a conference in San Diego or just to visit friends and hit the beach a few days, we look forward to you loving our home as much as we do.

Guest favourite
A spacious bedroom features a king bed dressed with a patterned duvet. A stone fireplace adds warmth, while a dresser and TV are positioned nearby. Natural light filters through large windows, highlighting the vaulted wooden ceiling and creating an inviting atmosphere.
Guest suite in Santee
4.95 out of 5 average rating, 363 reviews

Spacious 1 Bdrm Unit: king bed, fireplace, parking

Come relax in this bright & spacious 1 bedroom detached unit with private entrance. This room has a king bed, fireplace, full bathroom, table & chairs, mini fridge/freezer, microwave, closet ,dresser, Tv and beautiful mountain views. La Jolla Beaches, downtown San Diego, the Zoo, and Sea World are 25 minutes away. Santee Lakes is just a short drive away where you can enjoy fishing, paddle boating, splash park, biking and picnic area. Mission Gorge Trails is also located just 5 minutes away.

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?

Top guest favourite
A studio space features a queen bed with a patterned comforter, complemented by bedside lamps. A seating area with a reclining sofa is positioned near a 65" TV, providing an inviting setup for relaxation. The kitchenette is equipped with modern appliances, contributing to functional living.
Guest suite in Lakeside
5 out of 5 average rating, 110 reviews

Cozy, secure, and quiet studio in Lakeside

Studio granny flat w/full bath. Large windows front & back giving great natural light. Located at the end of a dead-end private drive. The 420 sq ft space includes a 65" HD TV w/DirectTV service, high speed wireless & wired internet, kitchenette w/convection cook microwave, fridge/freezer, w/many other extras. Unit was recently remodeled with new furniture. 1 Queen bed, dbl recliners, & dinette. (Also, the picture of the front of our property is not accurate - Airbnb uses Google photos 😕)

Guest favourite
A cozy living area showcases a modern yet rustic design, featuring a large wooden table and comfortable seating. Warm lighting from pendant fixtures complements the natural wood accents on the walls, while a decorative fireplace enhances the inviting atmosphere.
Farm stay in Lakeside
4.96 out of 5 average rating, 374 reviews

The Outside Inn at The Tipsy Goat Ranch

Nestled near Iron Mountain, a popular hiking destination, and less than 16 miles from San Diego's pristine beaches and local attractions, enjoy all SD has to offer in a one-of-kind farm-to-beach experience. Immerse yourself in a rarely seen side of San Diego you won't find anywhere else. Based on adventure, wrapped in luxury, a deep love for nature and the creatures it inhabits (mini goats, alpacas, babydoll sheep, lop bunnies, and chickens), it'll be a tranquil getaway you'll never forget.

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
The tiny home is nestled among vibrant flowers and lush greenery. A rainbow arcs overhead, enhancing the cheerful exterior of the home, which features large windows and a welcoming porch. The surrounding landscape showcases a peaceful rural setting with gentle hills in the background.
Tiny home in Lakeside
4.98 out of 5 average rating, 127 reviews

Home at the Sanctuary

Welcome to our charming and eco-friendly tiny home located in between fruit orchards and an animal rescue in a serene rural setting. The perfect place to disconnect from the hustle and bustle of city life and immerse yourself in nature. Wake up to the sounds of birds chirping and the sight of our resident farm animals grazing in the pasture. Pick any of the ripe fruit from over 70 different fruit trees. Come experience sustainable living and succulent garden in our charming tiny home.

Guest favourite
An open living area features a comfortable sofa and a sleek glass coffee table. Natural light fills the space through large windows, complemented by soft curtains. Nearby, a dining area with seating and a well-equipped kitchen area is visible, enhancing the overall spacious feel.
Cottage in Lakeside
4.95 out of 5 average rating, 132 reviews

Modern Cottage Getaway!

Welcome to your cozy getaway! This charming 1,000+ sq ft cottage offers an open-concept layout. Perfect for couples, small families, solo travelers, or anyone looking for a peaceful retreat. 🧺 Washer and dryer included for added convenience Located in a very quiet, residential neighborhood—ideal for those seeking rest and relaxation. 🚗 Parking: Guests have 1/2 reserved parking spot in the driveway. No Street Parking 🚭 No smoking 🐾 No pets or service animals due to health concerns

Guest favourite
An outdoor patio area features cushioned, wooden seating arranged around a gas fire pit. In the background, mountains and rolling hills are visible, complemented by a clear sky. A grill is seen in the corner, enhancing the outdoor living experience.
Guest suite in Sky Ranch
4.99 out of 5 average rating, 107 reviews

Hillside Retreat with Views

Escape to the mountains of San Diego and into a peaceful, well-furnished, private living space with plenty of room to spread out and enjoy the California lifestyle. Take in the panoramic views of El Capitan and the Cuyamaca mountain range as you enjoy your favorite beverage around the firepit. California awaits as you can wander east to the mountains and desert, or west to the beaches and shopping centers. Legoland, Seaworld, and the Sesame Place waterpark are all within a short drive.

Top guest favourite
The welcoming entrance of Cedar Cottage is framed by lush greenery and decorative potted plants. A wooden porch, adorned with comfortable seating, leads to glass-paned doors. Elements such as a bubbling fountain and seasonal pumpkins add charm to the rustic facade.
Cottage in El Cajon
4.99 out of 5 average rating, 144 reviews

Cedar Cottage Retreat with Mountain View’s

Welcome to the Cedar Cottage nestled in the foothills of San Diego county. Where Vintage/Rustic charm meets modern sophistication. The Cottage sleeps 3 in 1 Queen bed and 1 comfortable Twin bed, 1 bathroom. Pet friendly. Just 2 miles from Sycuan resort, casino & golf . Get back to nature at this delightful cabin hideaway in the hills just 3.5 miles from the quaint town of Alpine. This very special private estate has natural beauty when looking out from the cottage in any direction.

Popular amenities for Lakeside holiday rentals

Quick stats about holiday rentals in Lakeside

  • Total rentals

    50 properties

  • Nightly prices starting at

    € 51 before taxes and fees

  • Total number of reviews

    2.1K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    30 properties have a pool

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  5. Lakeside