
Holiday houses in Lakeside
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Top-rated holiday rentals in Lakeside
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

East Watch- a private getaway
East Watch is a 740 sq ft, 1 bedroom private retreat that provides the comforts and amenities of home with the style of a high-end hotel. All 5 to 15 min from shopping, downtown, and the beach. It's a short walk from Mt. Helix Park which offers a 360* view, weekday yoga, and stunning sunrises and sunsets. We have EV high speed car charging, a full kitchen with all appliances, workspace with dedicated fast WIFI, a spa shower, and super comfortable beds and pillows. Stay and let us charm you!

San Diego Mountain Retreat
3 bedroom 1 bathroom loft (2 separate sides) open concept guest house. Very peaceful East San Diego getaway. Enjoy beautiful ocean and Mountain Views during the day then relax in the jacuzzi with breath taking sunsets and the city lights at night. Best views in San Diego! Only 25 minutes from the SD airport and beaches. Minutes away from 2 local wineries and casinos. House sleeps 6 but you can invite guests up for the day for a fee. Event prices will be discussed per event. We live in main home

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.

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.

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 😕)

Stylish Boho Studio | Walk to Cafes | Outdoor Livi
The studio is located within a quiet leafy neighborhood right in the heart of La Mesa giving you a great base to explore everything San Diego has to offer. Inside you will find a bright, sun-filled space with a chic kitchen, an open plan living/dining area with a comfortable sofa bed, a stylish queen bedroom and a modern, sparkling bathroom with a built in laundry. Stay a short 15 min walk to a shopping center nearby with cafes, restaurants and stores and an easy 15 min drive into Downtown.

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.

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

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.

Sycamore Creek cottage with Mountain View’s
Welcome to Sycamore Creek Cottage. A unique retreat in the foothills of San Diego county. A Delightfully decorated, fully furnished 2 room studio cottage . Sleeps 1 or 2 in a comfortable Queen bed. 1 full bathrooms, Fully fenced private patio, BBQ , firepit area with beautiful garden and mountain views. Pet friendly. close to Alpine & Sycuan Resort & golf. Ideal for business travelers, work remotely, visiting family or friends . I look forward to hosting you.

Gorgeous Guest Home
NEW 1 bed/1bath guest home located in beautiful Alpine. Includes a fully furnished living space, equipped kitchenette, Two Smart TVs, and WIFI. Extra large room with a super comfy Queen size bed. Full size bathroom with washer and dryer. Unit has A/C and heat. Parking is located on property. Wonderful neighbors and neighborhood. The entrance is completely private. Minutes to Viejas or the Sky Falconry. 🦅
Popular amenities for Lakeside holiday rentals
Other great holiday rentals in Lakeside

Lakeside Luxury-Panoramic Paradise

Private cozy house

The Queen House

A Perfect Pet Friendly Getaway.

Not Quite Perfect

The Bunny’s Burrow | Jamul Mountain Getaway

Little Cozy Guesthouse in Lakeside

Lakeside Haven | Mountain Views, Private Pool
When is the best time to visit Lakeside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $278 NZD | $348 NZD | $364 NZD | $302 NZD | $294 NZD | $352 NZD | $355 NZD | $364 NZD | $297 NZD | $384 NZD | $357 NZD | $410 NZD |
| Avg. temp | 15°C | 15°C | 16°C | 17°C | 18°C | 20°C | 21°C | 22°C | 22°C | 20°C | 17°C | 14°C |
Frequently Asked Questions
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.
How much does it cost to stay in house rentals in Lakeside?
Experience the best of Lakeside with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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.
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.
Are there Lakeside house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Lakeside, available on Airbnb. Make a splash and soak up the sun in style!
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 air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Lakeside. Enjoy a tailored experience with all the comforts you desire.
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.
Do house rentals in Lakeside have wifi?
Absolutely! We offer over 30 house rentals with wifi in Lakeside. Enjoy a tailored experience with all the comforts you desire.
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.
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 $85 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
50 of Lakeside holiday 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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