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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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Top guest favorite
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, 191 reviews

Townhouse - 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

Guest favorite
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
4.95 out of 5 average rating, 387 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 favorite
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, 152 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 favorite
A contemporary casita is set against a vibrant sunset, showcasing large windows that reflect the warm colors of the sky. The entrance features a clear path leading to a well-lit doorway, surrounded by natural landscaping and scenic hillside views.
Home in Lakeside
4.94 out of 5 average rating, 120 reviews

San Diego Casita for 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 a GE electric cooktop, refrigerator, microwave/air fryer, rice cooker, 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 sofa bed. Relax on the large 240 sq. ft. private deck featuring a fire pit, adirondack chairs and BBQ.

Top guest favorite
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, 118 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 favorite
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.
Guesthouse in La Mesa
4.99 out of 5 average rating, 214 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 favorite
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 favorite
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, 115 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 favorite
A bedroom is equipped with a metal bed frame featuring a floral-patterned quilt. Two bedside lamps cast soft light, and wall art in calming colors adds a touch of design. Sliding glass doors reveal outdoor access to a private patio area with furniture.
Apartment in La Mesa
4.98 out of 5 average rating, 181 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!

Top guest favorite
A modern kitchen area features sleek cabinetry and stainless-steel appliances. A spacious island with bar seating provides ample space for dining. Large windows allow natural light to fill the room, with greenery visible beyond the sliding glass doors.
Loft in Little Italy
4.98 out of 5 average rating, 176 reviews

Waterfront Loft | 1BR | Little Italy | Downtown

The local neighborhood is highly walk-able and perched along the San Diego Bay in Little Italy. Little Italy is the most vibrant neighborhood in downtown San Diego with a main street that abounds with restaurants, boutiques, craft beer, and wine bars all at your doorstep. This is a very urban location which brings a lot of urban noise. The unit sits adjacent the train and trolley line in the urban core. No parking provided, Ideal for guests without a car.

Top guest favorite
A sunset is captured over the ocean, with shades of orange, pink, and yellow in the sky. Silhouettes of palm trees frame the scene, while the distant pier is visible along the coastline. The tranquil atmosphere reflects a peaceful end to the day.
Guest suite in Ocean Beach
4.95 out of 5 average rating, 786 reviews

Place to Stay with Private Entrance near Beach

The room has a private entrance. It's ideally located in a residential area of Ocean Beach. 5 blocks to the beach, OB pier, and 2 blocks to village life, shops & restaurants. It has a queen bed, a small private bathroom with a shower, a fridge, TV, Wifi, microwave, etc. Guests will love the location and privacy! Beach chairs, towels, umbrellas, etc. are available for your enjoyment. Enjoy the great ocean view from the backyard.

Guest favorite
A light-filled studio apartment is presented, featuring a dining table with two chairs and a kitchenette equipped with modern appliances. The space boasts a ceiling fan and large mirror, while a bathroom area is visible with a blue rug. Neutral-toned walls create a clean atmosphere.
Guesthouse in San Diego
4.87 out of 5 average rating, 1,072 reviews

Private Garden Studio

Enter through a hidden garden filled with plants into a cute, clean, recently refurbished studio apartment. Although the house sits on a quiet street with abundant free street parking, it is within easy walking distance of craft breweries, cocktail bars, cafes, and some of San Diego's best restaurants, as well as Trolley Barn Park. We're also an easy shot to the zoo, Balboa Park museums, downtown, and the beaches.

Popular amenities for Lakeside vacation rentals

When is the best time to visit Lakeside?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$34,022 GYDG$42,579 GYDG$44,458 GYDG$36,944 GYDG$35,900 GYDG$42,997 GYDG$43,414 GYDG$44,458 GYDG$36,318 GYDG$46,962 GYDG$43,623 GYDG$50,093 GYD
Avg. temp15°C15°C16°C17°C18°C20°C21°C22°C22°C20°C17°C14°C

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 vacation rentals in Lakeside

  • Total vacation rentals

    Explore 50 vacation rentals in Lakeside

  • Nightly prices starting at

    Lakeside vacation rentals start at G$10,436 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,080 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Lakeside vacation rentals include wi-fi 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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