Holiday houses in Lakeside

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Top-rated holiday rentals in Lakeside

Guests agree: these stays are highly rated for location, cleanliness and more.

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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.
Guesthouse in Crest
4.99 out of 5 average rating, 212 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.

Top Guest favourite
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.
Guesthouse in La Mesa
4.97 out of 5 average rating, 102 reviews

East Watch- a private getaway

East Watch is a 740 sq ft, 1 bedroom private retreat that provides the comforts and amenities of home with the style of a high-end hotel. All 5 to 15 min from shopping, downtown, and the beach. It's a short walk from Mt. Helix Park which offers a 360* view, weekday yoga, and stunning sunrises and sunsets. We have EV high speed car charging, a full kitchen with all appliances, workspace with dedicated fast WIFI, a spa shower, and super comfortable beds and pillows. Stay and let us charm you!

Top Guest favourite
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
4.98 out of 5 average rating, 102 reviews

San Diego Mountain Retreat

3 bedroom 1 bathroom loft (2 separate sides) open concept guest house. Very peaceful East San Diego getaway. Enjoy beautiful ocean and Mountain Views during the day then relax in the jacuzzi with breath taking sunsets and the city lights at night. Best views in San Diego! Only 25 minutes from the SD airport and beaches. Minutes away from 2 local wineries and casinos. House sleeps 6 but you can invite guests up for the day for a fee. Event prices will be discussed per event. We live in main home

Top 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, 395 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.

Guest favourite
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.
Home in Eucalyptus Hills
4.93 out of 5 average rating, 123 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.

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, 118 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
An open kitchen and living area is shown, featuring a modern design with white cabinetry and wooden accents. A comfortable sofa is positioned in front of a wall-mounted TV. A dining table with seating for four is placed next to the kitchen, surrounded by natural light.
Guest suite in La Mesa
4.87 out of 5 average rating, 186 reviews

Stylish Boho Studio | Walk to Cafes | Outdoor Livi

The studio is located within a quiet leafy neighborhood right in the heart of La Mesa giving you a great base to explore everything San Diego has to offer. Inside you will find a bright, sun-filled space with a chic kitchen, an open plan living/dining area with a comfortable sofa bed, a stylish queen bedroom and a modern, sparkling bathroom with a built in laundry. Stay a short 15 min walk to a shopping center nearby with cafes, restaurants and stores and an easy 15 min drive into Downtown.

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, 395 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 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
4.96 out of 5 average rating, 135 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

Top 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, 119 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
Lavender plants are prominently displayed in the foreground, with tall, slender purple blooms reaching towards a clear blue sky. In the background, a lush green lawn and trees are visible, enhancing the garden's serene setting.
Farm stay in Harbison Canyon
4.97 out of 5 average rating, 106 reviews

Sycamore Creek cottage with Mountain View’s

Welcome to Sycamore Creek Cottage. A unique retreat in the foothills of San Diego county. A Delightfully decorated, fully furnished 2 room studio cottage . Sleeps 1 or 2 in a comfortable Queen bed. 1 full bathrooms, Fully fenced private patio, BBQ , firepit area with beautiful garden and mountain views. Pet friendly. close to Alpine & Sycuan Resort & golf. Ideal for business travelers, work remotely, visiting family or friends . I look forward to hosting you.

Guest favourite
A cozy living space is furnished with a dark leather sofa facing a coffee table. A dining area, equipped with a wooden table and four chairs, is visible. Light-colored walls are complemented by plantation shutters and two art pieces, while a ceiling fan hangs overhead.
Guesthouse in Alpine
4.98 out of 5 average rating, 112 reviews

Gorgeous Guest Home

NEW 1 bed/1bath guest home located in beautiful Alpine. Includes a fully furnished living space, equipped kitchenette, Two Smart TVs, and WIFI. Extra large room with a super comfy Queen size bed. Full size bathroom with washer and dryer. Unit has A/C and heat. Parking is located on property. Wonderful neighbors and neighborhood. The entrance is completely private. Minutes to Viejas or the Sky Falconry. 🦅

Popular amenities for Lakeside holiday rentals

When is the best time to visit Lakeside?

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Avg. price$278 NZD$348 NZD$364 NZD$302 NZD$294 NZD$352 NZD$355 NZD$364 NZD$297 NZD$384 NZD$357 NZD$410 NZD
Avg. temp15°C15°C16°C17°C18°C20°C21°C22°C22°C20°C17°C14°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Lakeside?

    Lakeside has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Lakeside?

    Experience the best of Lakeside with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Lakeside?

    Four-legged friends are welcome in Lakeside. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Lakeside?

    Yes! Work meets play with ease at over 30 vacation rentals in Lakeside featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Lakeside house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Lakeside, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Lakeside?

    Make yourself at home in Lakeside by choosing from our most frequently booked neighborhoods. We have over 380 vacation rentals in Lakeside, and over 320 vacation rentals in Winter Gardens.

  • Do house rentals in Lakeside have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Lakeside. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lakeside have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Lakeside. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lakeside have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Lakeside. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lakeside have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Lakeside. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Lakeside

  • Total holiday rentals

    Explore 50 holiday rentals in Lakeside

  • Nightly prices starting at

    Lakeside holiday rentals start at $85 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Lakeside holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Lakeside rentals

  • 4.9 Average rating

    Lakeside stays are highly rated by guests—averaging 4.9 out of 5!

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