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Holiday rentals in Lakeside

Find and book unique accommodation on Airbnb

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 private garden area features two large orange umbrellas shading wicker seating arrangements. Lush greenery and colorful potted plants surround the space, with a stone patio leading to a warm-toned guesthouse wall. A window on the guesthouse reflects natural light, enhancing the serene atmosphere.
Guest house in Kensington
4.97 out of 5 average rating, 616 reviews

Central & Serene Secret Garden Guesthouse

My cozy & stylish Garden Guesthouse features colorful decor that gives a fun, relaxed vibe. Relax in style inside or outside in my peaceful garden w a cup of coffee, or glass of wine. I love to say a hi to my guests yet your privacy is #1. Reach me via Airbnb app if I can help! Kensington is a central, 1920’s historic neighborhood w shops & great local eateries. Close to downtown, Gaslamp, Zoo, airport, beaches, Balboa Park. Bus stop, & trolley nearby. Reserved off street parking space too!

Top guest favourite
The studio features exposed wooden beams and a spacious layout. A queen bed is positioned against the wall, while two comfortable chairs are set nearby. A well-equipped kitchen area with appliances and a counter is visible, alongside a door leading to the patio.
Tiny home in La Mesa
4.99 out of 5 average rating, 184 reviews

Casita de Pueblo - Private Yard, La Mesa Village

Enjoy a stylish experience at this centrally-located studio. Walking distance to La Mesa Village, where you can enjoy restaurants, coffee shops, boutiques, & more. With all the things you need in a kitchen to whip up any meal, and a patio to enjoy the San Diego sun. Hop on the trolley to get to anywhere. Bringing more friends or family along with you? We also have another listing, Casa de Pueblo at the same property. 20 min drive to the Beach or Downtown 15 min drive to Balboa Park or Old Town

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.
Guest house in El Cajon
4.99 out of 5 average rating, 209 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 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
4.96 out of 5 average rating, 379 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.

Top guest favourite
The welcoming entrance of Cedar Cottage is framed by lush greenery and decorative potted plants. A wooden porch, adorned with comfortable seating, leads to glass-paned doors. Elements such as a bubbling fountain and seasonal pumpkins add charm to the rustic facade.
Cottage in El Cajon
4.99 out of 5 average rating, 150 reviews

Cedar Cottage Retreat with Mountain View’s

Escape to the countryside. Welcome to the Cedar Cottage nestled in the foothills of San Diego county. Where Vintage/Rustic charm meets modern sophistication. The Cottage sleeps 3. 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.

Guest favourite
A spacious living area features a large, modern sectional sofa and a round dining table. A ceiling fan provides airflow, while a 50" smart TV displays a vibrant underwater scene. Light floods in through large windows, enhancing the inviting atmosphere, with surfboards displayed on the wall.
Home in Lakeside
4.94 out of 5 average rating, 114 reviews

SD Casita Sleeps 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 many amenities including a GE electric cooktop, refrigerator, microwave and air fryer, rice cooker, Kitchenaid mixer, 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 sofabed. How about a large deck with fire pit 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, 115 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 😕)

Top guest favourite
A private deck is shown, featuring a red umbrella over a round table with four chairs. The entrance to the guest house is framed by glass doors and accompanied by a vibrant red door. Lush greenery and flowerbeds enhance the outdoor space.
Guest house in La Mesa
4.99 out of 5 average rating, 208 reviews

Stunning Guest House 15 min. from Zoo, Downtown

Stunning guest house that's 15 minutes to San Diego Zoo + downtown San Diego. The cottage is decorated with mid-century and one-of-a kind furniture in a comfy living space overlooking a gorgeous garden. Enjoy the the garden on your private deck, watch TV while relaxing in the handcrafted Nicaraguan rocker or 1950s Danish slipper chair. The cottage also has a comfy queen-sized bed and a full kitchen that's stocked with what you'd need. Oh, and all guests arrive to a homemade loaf of bread.

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, 112 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
The poolside area features a well-maintained saltwater pool reflecting the colors of the sunset. Comfortable seating arrangements, including lounge chairs and a cozy fire pit, are visible. Large umbrellas provide shade, and lush greenery adds to the serene ambiance.
Guest house in Lake Murray
4.96 out of 5 average rating, 139 reviews

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

This is your perfect Guest House with a salted & heated pool & hot tub. We are located in a super quiet & very safe neighborhood in beautiful San Diego, 15 minutes drive to beaches, Downtown, La Jolla, Zoo, Stadiums, Sea World, Convention Center + more. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes and furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

Guest favourite
A light-filled living area features a comfortable white sofa adorned with various pillows. A small marble table sits in front of the sofa, complemented by fresh tulips in a vase. A side chair and decorative elements add to the inviting ambiance.
Apartment in La Mesa
4.81 out of 5 average rating, 102 reviews

Sweet Little La Mesa Condo(pool+hot tub) NEAR SDSU

1 Br condo Quite literally 15 minutes from ANY/EVERYTHING! Full kitchen, open living room, breakfast bar, full bathroom, large screen TV with fire stick. Cute, cozy patio.Have your morning coffee with the hummingbirds. Pool+ hot tub on site. 8 minute drive from Cowles Mountain, the highest peak in the area, GORGEOUS 40 up & 40 min down hike!!

Popular amenities for Lakeside holiday rentals

When is the best time to visit Lakeside?

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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 30 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 $60 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 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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 a kitchen?

    Absolutely! We offer over 30 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 30 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 30 homes with a kitchen, over 30 homes with wifi, over 30 homes with air conditioning, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 £45 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    50 of Lakeside holiday rentals include wifi 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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