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Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

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

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Guesthouse in El Cajon

4.99 out of 5 average rating, 172 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.

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 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.

Home in La Mesa

4.86 out of 5 average rating, 206 reviews

Newer "Manor Studio"

Centrally located in San Diego County this brand new studio style unit has a private entrance, private patio area and street parking. Furnished with a queen size bed, love seat, full bathroom and kitchen area. One large drawer to accommodate personal items, and a wall rack to hang clothing. There is a smart TV with WiFi streaming capabilities and lots of USB plugs to charge your devices. On street parking in front of unit (no parking in driveway). No Pets allowed. No Hair Dying allowed.

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.

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.

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.

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.

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..

Home in El Cajon

4.97 out of 5 average rating, 117 reviews

Suite Charles Way: A Cozy Fletcher Hills Studio

This newly remodeled spacious studio retreat features a private courtyard with barbecue, kitchenette, a brand-new California King bed, and a reclining love seat with charging ports. Enjoy a relaxed cabana vibe, a charming neighborhood and treetop views with easy access to all your favorite San Diego destinations. Within minutes from Grossmont Sharp Hospital, Grossmont Center, the trolley and Grossmont College.

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.

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!

Vacation rentals for every style

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Unique stays

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Popular amenities for Lakeside vacation 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 vacation rentals in Lakeside

Hotel room in Ramona

4.89 out of 5 average rating, 66 reviews

One Bedroom Condo in San Diego Country Estates

Guesthouse in Lakeside

4.92 out of 5 average rating, 36 reviews

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

Tiny home in Lakeside

5 out of 5 average rating, 83 reviews

Home at the Sanctuary

Farm stay in El Cajon

5 out of 5 average rating, 45 reviews

Farmstay Gem near San Diego

Tiny home in Jamul

5 out of 5 average rating, 21 reviews

Majestic Private Mountain Glamping Oasis

Guesthouse in El Cajon

4.97 out of 5 average rating, 33 reviews

Barbie’s Guest House

Home in El Cajon

5 out of 5 average rating, 44 reviews

Quiet Country Home

Guesthouse in La Mesa

5 out of 5 average rating, 56 reviews

Beautiful Bright Mt. Helix Studio

Quick stats about vacation rentals in Lakeside

Total rentals
40 properties
Nightly prices starting at
G$12,518 GYD 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

Frequently Asked Questions

Are there Lakeside vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Lakeside, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Lakeside have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Lakeside. Enjoy a tailored experience with all the comforts you desire.
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.
How much does it cost to stay in house rentals in Lakeside?
Experience the best of Lakeside with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Lakeside?
Lakeside has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Lakeside have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Lakeside. Enjoy a tailored experience with all the comforts you desire.
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.
Do house rentals in Lakeside have free parking?
Absolutely! We offer over 20 house rentals with free parking in Lakeside. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Lakeside?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with wifi, over 20 homes with air conditioning, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Lakeside have wifi?
Absolutely! We offer over 20 house rentals with wifi in Lakeside. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore