Vacation rentals in Lakeside

Guesthouse in Rancho Bernardo

A scenic view captures lush hillsides and a calm lake under a clear sky, with a rainbow arching gracefully over the landscape. Green vegetation sprawls across the area, adding vibrancy to the tranquil scene.

4.91 out of 5 average rating, 783 reviews

Hilltop cabin retreat with lake & mountain views

Rustic hilltop cabin overlooking Lake Hodges. Surrounded by open canyons & mountains, you will feel like you're a million miles away from everything as you take in the views from the cabin, deck or the outside shower, swim in the saltwater pool, or relax by the fire bowl. A short walk to lake with boating, fishing & miles of hiking/mountain biking trails. Property offers swimming pool, fire bowl, and shaded arbor. SD Zoo Safari Park, wineries, breweries, & ocean beaches all within easy reach.

4.99 out of 5 average rating, 195 reviews

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.

Guesthouse in El Cajon

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.

4.95 out of 5 average rating, 353 reviews

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

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.

A spacious studio features a comfortable queen bed topped with a patterned blanket. Natural light filters in through a nearby window, illuminating the room's neutral tones. A piece of art depicting a tree-lined path hangs above the bed, enhancing the room's calming ambiance.

4.99 out of 5 average rating, 112 reviews

Terra Mesa - Charming Retreat

Welcome to TerraMesa! This charming studio boasts a thoughtfully designed space, blending modern comfort with a touch of rustic elegance. With a fully equipped kitchenette, a plush queen bed, and a stylish sitting area, it’s perfect for couples seeking a romantic getaway or solo travelers exploring the San Diego area. Sip a cup of coffee or glass of wine in your private little patio. Centrally located in scenic Lakeside, you’ll have easy access to downtown, beaches or our local mountain towns.

4.99 out of 5 average rating, 117 reviews

The tiny home is nestled among vibrant flowers and lush greenery. A rainbow arcs overhead, enhancing the cheerful exterior of the home, which features large windows and a welcoming porch. The surrounding landscape showcases a peaceful rural setting with gentle hills in the background.

Tiny home in Lakeside

Home at the Sanctuary

Welcome to our charming and eco-friendly tiny home located at a succulent nursery and animal rescue in a serene rural setting. The perfect place to disconnect from the hustle and bustle of city life and immerse yourself in nature. Wake up to the sounds of birds chirping and the sight of our resident farm animals grazing in the pasture. You can even enjoy fresh eggs from our free-range chickens for breakfast! Come experience sustainable living and succulent nursery in our charming tiny home.

5 out of 5 average rating, 106 reviews

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

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 😕)

4.96 out of 5 average rating, 371 reviews

A cozy living area showcases a modern yet rustic design, featuring a large wooden table and comfortable seating. Warm lighting from pendant fixtures complements the natural wood accents on the walls, while a decorative fireplace enhances the inviting atmosphere.

Farm stay in Lakeside

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.

4.95 out of 5 average rating, 131 reviews

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

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

4.99 out of 5 average rating, 100 reviews

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 Lakeside

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.

4.98 out of 5 average rating, 229 reviews

A spacious living area is equipped with a plush sofa and light-colored chairs, accented by decorative pillows. A wooden coffee table rests on a colorful area rug. Natural light fills the room through two windows, highlighting a work desk and welcoming artwork on the wall.

Guesthouse in El Cajon

Fletcher Hills - modern 1 BR.Easy, no step access.

** 36 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..

4.97 out of 5 average rating, 121 reviews

A light-filled dining area features a simple white table set for two, complemented by wooden chairs. A comfortable seating area with neutral cushions is positioned against a green wall, while a glimpse of the kitchen is visible in the background, showcasing charming decor and a welcoming ambiance.

Guest suite in El Cajon

Farmhouse Cottage Retreat with Beautiful View’s

Welcome to the farmhouse studio cottage. Located in the foothills of San Diego County. See beautiful views as you drive down the tree lined inner roads of the property. Hear birds as you awake in the morning and an occasional rooster off in the distance. Get back to nature at this lovingly appointed studio hideaway. Close to Alpine and Sycuan Resort & Casino, Golf. Pet friendly, Pet fee of $60.00 per pet per stay.

4.98 out of 5 average rating, 105 reviews

A cozy living space is furnished with a dark leather sofa facing a coffee table. A dining area, equipped with a wooden table and four chairs, is visible. Light-colored walls are complemented by plantation shutters and two art pieces, while a ceiling fan hangs overhead.

Guesthouse in Alpine

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. 🦅

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Lakeside vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Lakeside

Superhost

The image showcases a well-maintained house surrounded by a lush green lawn, featuring various palm trees. A fountain is situated in the foreground amidst landscaped gardens, enhancing the serene ambiance of the outdoor space.

4.78 out of 5 average rating, 32 reviews

A Perfect Pet Friendly Getaway.

4.98 out of 5 average rating, 93 reviews

A newly constructed casita is framed by natural landscaping, with a gravel path leading to the entrance. The structure features large windows that offer views of the surrounding mountain landscape, highlighted by the soft glow of sunset.

Farm stay in Lakeside

Casita Sleeps 6 at The Morey de Prieto Surf Ranch

An outdoor entertainment area features a dining table with chairs beneath a large umbrella, providing shade. Two adirondack chairs are positioned nearby. A grill is located in the corner, while a decorative fence with painted designs adds a colorful touch to the space.

5 out of 5 average rating, 28 reviews

Farmhouse on Sunny Outdoor Dining area 20min to SD

4.89 out of 5 average rating, 38 reviews

A compact kitchenette is displayed, featuring stainless steel appliances, including an oven and microwave. A small table with a chair is positioned against the wall, while light filters in through a window above the sink, enhancing the modern, clean layout.

Guesthouse in Lakeside

Little Cozy Guesthouse in Lakeside

The living area is accented with wooden beams and features a cozy sofa, an armchair, and a round wooden coffee table. Natural light fills the room through a window, with a piece of abstract artwork displayed on the wall, enhancing the inviting space.

4.94 out of 5 average rating, 18 reviews

Lakeside Haven | Mountain Views, Private Pool

A private deck features a small round table surrounded by two blue chairs, situated under a palm tree. The view includes rolling hills and a clear blue sky with scattered clouds, offering a peaceful outdoor space to enjoy the scenery.

4.95 out of 5 average rating, 19 reviews

Studio In Home with Private Entry

5 out of 5 average rating, 77 reviews

The exterior of the home features a single-story design with a welcoming front porch. A green railing enhances the porch area, and multiple windows allow natural light to enter. A spacious driveway leads up to the house, with a manicured lawn and surrounding shrubs.

Home in El Cajon

Quiet Country Home