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Vacation rentals in Lakeside

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Lakeside

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

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Home in Alpine

4.99 out of 5 average rating, 172 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 swing set/tramploine not included with Airbnb.

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.

Guest suite in La Mesa

4.94 out of 5 average rating, 100 reviews

Relaxing guest studio in La Mesa

Relax with the whole family at this peaceful place to stay. Forget your worries in this spacious and serene space. This is a fully furnished suite with: -2 Off-street parking spots -1 King-size bed -1 Pull-out Queen-size sofa bed -Smart-TV (Use your app log-ins for services) -295 Mbps Wifi -Fully equipped kitchen -Dining area with hidden leaf table to eat or work comfortably. !!! Very Important !!! -NO SMOKING -NO PETS -NO EXTRA GUESTS **There will be some construction noise during the day.**

Cottage in Lakeside

4.97 out of 5 average rating, 114 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, 294 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.

Farm stay in Lakeside

4.96 out of 5 average rating, 324 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, 117 reviews

Cedar Cottage Retreat with Mountain View’s

A countryside retreat. Escape for a long weekend, week or month. Work remotely with the great wifi, pet friendly. Just 2 miles from Sycuan resort and casino and 5 miles from Singing Hills golf resort. Get back to nature at this delightful cabin hideaway in the hills just 2 miles from the quaint town of Alpine. This very special private estate has natural beauty when looking out from the cottage in any direction. I look forward to hosting you. Pets welcome $60 pet fee per pet per booking.

Home in Lakeside

4.95 out of 5 average rating, 110 reviews

Vibey😎Pool House🏡 ModernFarmhouse 1700sqft + View🌄

Come and relax as this home gives you the open concept, views, and coziness we all desire when you're on vacation. It is the perfect location, right off of San Diego's main freeway with options to drive to the beach, mountains, or desert. The backyard is an oasis that you can enjoy during the day and at night with our splash pool that easily heats into an extra large jetted hot tub with waterfall. Enjoy the view from inside with floor to ceiling windows or outside with plenty of seating.

Yurt in El Cajon

4.97 out of 5 average rating, 315 reviews

Glamping @ Eden East

Looking for the perfect place to chill with your favorite person or just some alone time? Yome with private patio and spacious pool area. Not just a place to stay but an artsy retreat full of color, butterflies, birds and life. Hot shower and flush toilet in plant filled outdoor bathroom. We've been told the shower alone is worth the stay. Come glamping and get cozy with heated blanket, heater and flannel sheets. By reserving, we assume you've read the entire ad and agree to all rules.

Home in Lakeside

4.93 out of 5 average rating, 131 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.

Rental unit in La Mesa

4.98 out of 5 average rating, 135 reviews

Lovely Hideaway Studio by Village-Private Patio

Enjoy the cool vibe at this unique rustic getaway tucked back on a tree-lined hill 5 minutes above City of La Mesa Village, 20 minutes from downtown San Diego. The studio is on the ground floor of our two-story house. We live on the 2nd floor, and the studio is it's own completely private space. 5 miles to San Diego State University; 16-20 miles to San Diego beaches; 10 miles to Downtown San Diego; 15 miles to Sea World San Diego; and 13 miles to the World Famous San Diego Zoo!

Guesthouse in El Cajon

4.98 out of 5 average rating, 205 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..

Vacation rentals for every style

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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, 64 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

Farm stay in El Cajon

5 out of 5 average rating, 45 reviews

Farmstay Gem near San Diego

Home in La Mesa

5 out of 5 average rating, 34 reviews

Shadow House*November 14-25 discount!*

Farm stay in Lakeside

4.98 out of 5 average rating, 45 reviews

San Diego Casita - The Morey by Prieto Surf Ranch

Guesthouse in El Cajon

4.97 out of 5 average rating, 32 reviews

Barbie’s Guest House

Home in Lakeside

4.83 out of 5 average rating, 6 reviews

Studio In Home with Private Entry

Home in El Cajon

5 out of 5 average rating, 42 reviews

Quiet Country Home

Quick stats about vacation rentals in Lakeside

Total rentals
40 properties
Nightly prices starting at
G$12,524 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 a kitchen, over 20 homes with free parking, over 20 homes with air conditioning, over 20 homes with wifi, 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.

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