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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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Guesthouse in Rancho Bernardo

4.92 out of 5 average rating, 701 reviews

Hilltop cabin retreat with lake & mountain views

Rustic hilltop cabin overlooking Lake Hodges. Surrounded by open canyons & mountains, you will feel like you're a million miles away from everything as you take in the views from the cabin, deck or the outside shower, swim in the saltwater pool, or relax by the fire bowl. A short walk to lake with boating, fishing & miles of hiking/mountain biking trails. Property offers swimming pool, fire bowl, and shaded arbor. SD Zoo Safari Park, wineries, breweries, & ocean beaches all within easy reach.

Guest favourite

Cottage in Lakeside

4.97 out of 5 average rating, 116 reviews

Modern Cottage Getaway!

Open and airy cottage getaway in Lakeside. This cottage has an open layout that allows you to be everywhere at one time! It Reminds me of a loft space. Over 1000 sqft. Recently renovated bathroom and add a washer and dryer! Great for couples, small families and anyone else! Very quiet neighborhood & all neighbors are older. Guest have 1 reserved parking spot on driveway. (No street parking) No smoking anywhere on property (Inside or outside) No pets or service animals. Health Hazard

Guest favourite

Guest suite in Santee

4.95 out of 5 average rating, 297 reviews

Spacious 1 Bedroom unit w/ king bed & 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

Guesthouse in El Cajon

4.97 out of 5 average rating, 147 reviews

Mt Helix Studio Loft with Mountain Views

Mountain Views: Freshly renovated, quiet and spacious studio loft in private neighborhood. Close to coffee shops, grocery stores, and quick access to major highways. 500 sqft open concept. Laundry, Fast Internet, Cable TV and streaming services. Additionally, if you like oranges and avocados we grow them on the property (Seasonal of course). We also have a chicken coop and fresh eggs on request. Security Deposit Hold and Signed Short-term Rental Agreement Required as we live on the property.

Guest favourite

Farm stay in Lakeside

4.96 out of 5 average rating, 326 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

Cottage in El Cajon

4.98 out of 5 average rating, 118 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.

Guest favourite

Home in Alpine

4.99 out of 5 average rating, 174 reviews

Fully Fenced Alpine Property with Guest House

Our guest house is located in the back of our personal property & kept private by fencing. Our property is fully fenced & guests have access in & out by using a keypad. We have laundry facilities, a queen size bed in the master bedroom, a sofa sleeper in the living room/kitchen area and a private patio with bbq. We occupy the main home on the property. We have 2 dogs on the property so other animals are not recommended at this location. Children trampoline not included with Airbnb.

Guest favourite

Home in Lakeside

4.93 out of 5 average rating, 133 reviews

The Hills Oasis Pool, Jacuzzi & Pickleball

SEND US A MESSAGE FOR SPECIAL OFFER! Imagine booking the most memorable experience with your party! Kick back and relax in a safe stylish, family and friend oriented experience! Check in contactless and enjoy! Cozy, modern and includes an outdoor fire pit, spa, and pickle ball! With the whole house comes parking up to 6 cars, 2 bathrooms (1 is ADA compliant), and an alluring kitchen. The entire house is 30 minutes from the beach, 45 to the snow, and 30 minutes from downtown San Diego.

Guest favourite

Guesthouse in El Cajon

4.98 out of 5 average rating, 206 reviews

Fletcher Hills - modern 1 BR.Easy, no step access.

** 48 hours between check-ins. Thorough cleaning and sanitizing.. Four night minimum stay. Dogs ONLY are welcomed on a case by case basis. They must be house trained and are not permitted on any furniture. If you instant book, you must contact me about your pet within 24 hours. Smoking is permitted in the outside areas - patio, gazebo, yard. Easy freeway access helps any commute to downtown and area attractions. Having your own vehicle is the best way to get around..

Guest favourite

Campervan/RV in El Cajon

4.94 out of 5 average rating, 302 reviews

Make memories this holiday in Retro Bettie Blue

Your one of a kind RV adventure is centered between the Laguna Hills and the coast of San Diego, in sunny East County! Glamp in style in the new 2019 Retro Riverside trailer. This camper is set up with all the modern amenities with the quaint mid-century modern design of a teardrop trailer. The trailer sleeps 3 adults or 2 adults and 2 small children. You will have 1 designated parking spot available to you. Come have flashback fun in a Retro RV!

Guest favourite

Guesthouse in Lakeside

4.94 out of 5 average rating, 137 reviews

Sky Mesa-Adorable Cottage on the Hill

SkyMesa is a lovely space to unwind and relax after a busy day. Awake refreshed and ready for a day of exploring San Diego County in this quaint, sunny cottage with impressive views. Head out and wander east to the mountains and desert, or west to the many beautiful beaches. After a day of fun, grab a glass of wine, soak in the hot tub, and look out over the Cuyamaca Mountains.

Guest favourite

Home in San Diego

4.98 out of 5 average rating, 413 reviews

Private Home with Sweeping Views!

Enjoy sweeping panoramic views from your own private 600 square feet guest house in the San Diego countryside! This is the ideal place to escape... If you're looking for quiet, serenity, and peace you've found it here! If you're looking to party or hold an event, this is NOT the place. Please read through the rules before booking. Thank you!

Holiday rentals for every style

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Popular amenities for Lakeside holiday rentals

Free parking on premises

Air conditioning

Stay near Lakeside's top sights

Eastbound Bar & Grill12 locals recommend

Ottavio's Italian Restaurant8 locals recommend

Lakeside Rodeo Arena7 locals recommend

Santee Drive In Theatre7 locals recommend

Lake Jennings6 locals recommend

Willowbrook Country Club3 locals recommend

Other great holiday rentals in Lakeside

Guest favourite

Guesthouse in La Mesa

4.99 out of 5 average rating, 70 reviews

ino Mt. Helix Casita

Guest favourite

Guesthouse in El Cajon

4.96 out of 5 average rating, 69 reviews

Luxury *Private Studio Apartment

Guest favourite

Guesthouse in Lakeside

4.92 out of 5 average rating, 36 reviews

Quiet & Privacy 1.5 acres gated A+ views & A/C

Guest favourite

Farm stay in El Cajon

5 out of 5 average rating, 45 reviews

Farmstay Gem near San Diego

Guest favourite

Farm stay in Lakeside

4.98 out of 5 average rating, 47 reviews

San Diego Casita - The Morey by Prieto Surf Ranch

Guest favourite

Rental unit in El Cajon

4.9 out of 5 average rating, 40 reviews

Quaint Apt with International decor

Guest favourite

Guesthouse in El Cajon

4.97 out of 5 average rating, 33 reviews

Barbie’s Guest House

Guest favourite

Guesthouse in Lakeside

4.84 out of 5 average rating, 56 reviews

Cute Tiny House in Lakeside

Quick stats about holiday rentals in Lakeside

Total rentals
40 properties
Nightly prices starting at
$102 NZD before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
30 properties have a pool

Destinations to explore