Family-friendly vacation rentals in Lakeside

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Top-rated family-friendly rentals in Lakeside

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in La Mesa, California, US

4.92 out of 5 average rating, 208 reviews

Fig Tree Bungalow

Enjoy your stay in San Diego in this newly renovated guesthouse. Centrally located about a mile from Hwy 8, Hwy 125, and the Grossmont Trolley Station & Transit Center. Only a 15-20 minute drive to downtown, the airport, the beaches, and most of San Diego's other popular tourist attractions. This cozy, two-story, detached unit is located behind my home, and has its own private entrance and partitioned yard for your enjoyment. There's plenty of street parking directly in front of the house.

Sep 8 – 15

ﺩ.ﺇ451 per night

Guest favorite

Yurt in El Cajon, California, US

4.98 out of 5 average rating, 303 reviews

Glamping @ Eden East

Are you looking for the perfect most cozy space to chill with your favorite person or just for some time alone? Cozy Yome with private deck and spacious pool area. Not just a place to stay, but a peaceful retreat. Seasonal creek when it's raining & hot tub, hot shower and flush toilet in plant filled outdoor bathroom. Cozy warm fluffy sheets as well as space heater inside. By reserving, we are assuming you've read entire ad and agree to rules. We are located outside of the city of El Cajon.

Jun 10 – 17

ﺩ.ﺇ434 per night

Guest favorite

Home in Ramona

4.98 out of 5 average rating, 730 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.

Sep 16 – 23

ﺩ.ﺇ1,380 per night

Guest favorite

Apartment in San Diego

4.98 out of 5 average rating, 404 reviews

Lovely spacious upstairs studio with private entry

You’ll love our place as its spacious, quiet, private, comfortable in a residential neighborhood. The king-size bed is extremely comfortable and we have big relaxing patio chairs on our large balcony overlooking a beautiful landscaped garden. We are centrally located to most all of San Diego's attractions and close to freeways. The famous Gaslamp, Zoo, downtown and beaches are all within 13 to 20 minute drive. The kitchen is stocked with goodies, coffee and an assortment of teas.

Apr 11 – 18

ﺩ.ﺇ367 per night

Guest favorite

Guesthouse in El Cajon

4.98 out of 5 average rating, 191 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..

Mar 22 – 29

ﺩ.ﺇ432 per night

Guest favorite

Guesthouse in San Diego

4.99 out of 5 average rating, 364 reviews

*Private Canyon Retreat: Your Own Guesthouse*

An airy 1BD guest house at the end of a quiet dead-end street that overlooks a tranquil canyon....and an owner that works hard to create a fabulous experience for each guest; not just “another average rental”. With private entrance, full kitchen & bath, and double french doors opening onto a 400 sq ft deck with canyon views, it's the ideal retreat to come back to after exploring San Diego. Come fall in love with your next home away from home!

Oct 6 – 13

ﺩ.ﺇ586 per night

Guest favorite

Guesthouse in Dulzura

4.97 out of 5 average rating, 579 reviews

Vineyard & Winery Guest House

A hidden gem! Get away and stay at the historic pioneer era Clark Ranch established in 1885. Our guest house sits above our winery tasting room and has its own private entrance and driveway. It's clean, cozy, and self-contained . Make it a weekend 'getaway' stay and sample our fine wines , and Estate Olive Oil. There is a tower in the vineyard where you can enjoy a glass of wine and watch the sun set. Balcony overlooks Dulzura Creek.

Aug 5 – 12

ﺩ.ﺇ513 per night

Guest favorite

Cottage in La Mesa, California, US

4.97 out of 5 average rating, 278 reviews

La Mesa House On a Hill With Mountain Views!

SUNRISE PERCH - A standalone guest house, perfect spot for your San Diego stay! Enjoy inspiring sunrise views from the deck or relax indoors with super fast WiFi and a 43" TV. Enjoy a full kitchen! The king bed is super comfy and the bathroom is stocked. The space is only for those looking for quiet. No partying/loud socializing. Families welcome! Located 20 min from downtown San Diego and 25 min from the nearest beach (Ocean Beach).

Sep 1 – 8

ﺩ.ﺇ603 per night

Guest favorite

Home in El Cajon

4.95 out of 5 average rating, 309 reviews

Private Vineyard Estate w/ Guest House & Hot Tub

Enjoy a quiet oasis where family and friends can relax and play within the privacy of a gated 2-acre vineyard with endless on-site activities. The home layout is ideal for families or friends, with 4 bedrooms in the main house and the convenience and privacy of a separate Guest House (included in rental) with a full kitchen, living room, bathroom and bedroom. **Please no extra guests, events or gatherings**

Oct 2 – 9

ﺩ.ﺇ1,779 per night

Guest favorite

Guesthouse in Chula Vista, California, US

4.95 out of 5 average rating, 476 reviews

Private Casita in Great Eastlake Neighborhood

This room is a "casita" (seperate living space) away from the house. It has a private entrance with a cypher lock on the door. The room has new carpet, new tile, and queen size bed. The Eastlake neighborhood is very safe and very quiet. We are located about 20 mins from the beach, downtown San Diego, and San Diego international airport. This location is only 2 miles from the Otay Ranch Mall.

Jun 13 – 20

ﺩ.ﺇ396 per night

Guest favorite

Guesthouse in San Diego

4.94 out of 5 average rating, 333 reviews

The BEST NEST Clean, peaceful, private, affordable

This lovely private & separate unit is comfortable, clean and convenient. Your completely private suite is accessible via your own entrance. Minutes from major attractions, away from the hustle and bustle. Full kitchen for easy meal preparation. Located in a nice usually quiet neighborhood, close to major freeways. Enjoy the gorgeous San Diego weather in the quaint outdoor patio area.

Mar 1 – 8

ﺩ.ﺇ407 per night

Guest favorite

Guest suite in San Diego

4.97 out of 5 average rating, 301 reviews

Comfy, cozy updated Guest Home (patio, views, a/c)

Retreat to our peaceful guest home, only a short 20-minute drive from lively beaches. Relax in comfortable spaces filled with sunlight, perfect for enjoying your morning coffee or evening wine as you watch the sunset. After exploring the nearby shores and indulging in endless adventures, come back to unwind on the secluded patio or gaze at the stars while sipping cocktails.

Oct 13 – 20

ﺩ.ﺇ414 per night