Cottage vacation rentals in Lakeside

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Top-rated cottage rentals in Lakeside

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Top guest favorite
A cozy living area is presented with warm wood paneling and exposed beams. A comfortable sofa faces a rustic coffee table, while a nearby dining space features a round table set for four, surrounded by classic wooden chairs. Large windows offer views of the lush outdoors.
Cottage in El Cajon
4.99 out of 5 average rating, 154 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.

Top guest favorite
The spacious bedroom features a vaulted-beamed ceiling and an inviting California King-size bed, draped with a light blanket. Decorative elements include a wooden headboard, a vintage bench at the foot of the bed, and tasteful wall art. Natural light enters through the frosted window.
Cottage in Normal Heights
4.96 out of 5 average rating, 136 reviews

LOFT: Detached Cottage with Patio

Located in the heart of Normal Heights, where everything is walkable; pubs, markets, cafes. Local’s favorite! The LOFT is a spacious open-space studio loft, in a stand-alone cottage. Whether you fall in love with the vaulted-beamed ceilings, the Loft-style open kitchen, the clawfoot tub, the art & decor, or the lush landscaping, you won’t likely forget this place any time soon. Everywhere you turn is a feast for your eyes. We’ve ensured that comfort is as much of a priority as is beauty.

Top guest favorite
A living area features a light grey sofa and an elegant glass coffee table on a patterned rug. A ceiling fan hangs above, and large sliding glass doors open to a landscaped backyard. A cozy armchair and a TV complete the inviting space.
Cottage in Pacific Beach
4.85 out of 5 average rating, 260 reviews

Pacific Beach Cottage w/ backyard & parking

You’ll love our cozy beach cottage because it is fully equipped in a wonderful area in North Pacific Beach. Only a few blocks away from the beach and boardwalk. Our cottage is good for couples, solo adventurers, business travelers, families, and furry friends. It's close to the beach and lots of bars, restaurants, shops, cafes...Everything a traveler wants for a wonderful stay. We also love long stays and want to accommodate whatever you might need for your longer term stay in San Diego!

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 exterior view of a bungalow features an orange front door set against a light blue wall. Two small planters with ornamental grasses are positioned on either side of the entrance, and three steps lead up to the door. Large windows flank the entrance, allowing natural light to enter.
Cottage in Mission Beach
4.94 out of 5 average rating, 528 reviews

50 Steps to the Bay & 100 steps to the Ocean!

Mid-Century Modern inspired fully remodeled 1-bdrm + 1-bath beach bungalow with an additional Queen sofa pull-out bed for up to 4 people. All new interior finishes, air conditioning, heating, appliances, and furniture. Located on the nicest pedestrian-only court in Mission beach, this quiet community is occupied by long-term native SD residents. This cozy high-end contemporary home is perfect for a quiet & relaxing beach vacation. Unsafe for children (under 12), infants, or pets.

Top guest favorite
An outdoor patio area is furnished with four gray lounge chairs and a rectangular table in the center. A red umbrella provides shade over the seating arrangement. The backdrop includes a well-maintained structure with a large window and various potted plants. Lush greenery surrounds the setting.
Cottage in Greater North Park
4.86 out of 5 average rating, 314 reviews

Private Cottage near Balboa Park

Welcome to this stylish, romantic, and quiet casita situated in a private garden setting! Located in exciting North Park, you can walk just blocks to some of San Diego's best restaurants, cafes, and breweries, as well as the Observatory for concerts and Morley Field, home to a beautiful outdoor public pool and tennis facility. You are a five minute drive to the San Diego Zoo and Balboa Park, a 10 minute drive to downtown/airport, and a 15 minute drive to beautiful beaches.

Top guest favorite
A serene beach scene at sunset captures gentle waves lapping at the shore. The sky is painted in soft hues of blue, pink, and orange, while palm trees line the coastline in the distance. The tranquil atmosphere invites relaxation and reflection.
Cottage in La Jolla
4.92 out of 5 average rating, 512 reviews

La Jolla Beach Cottage Gem

This is the perfect beach cottage for your La Jolla stay. Located a few short blocks to world famous beaches & La Jolla's iconic Village. Within walking distance is the La Jolla Cove, restaurants, shops, parks, historic buildings, museums, art center, the library, yoga, gyms, spas and more. A short drive to The Shores, scuba diving, kayaking, snorkeling, the Pier & Birch Aquarium. Enjoy all the comforts of home and the pleasures of a vacation.

Top guest favorite
Cottage in Ocean Beach
4.94 out of 5 average rating, 420 reviews

Fabulous Cottage at the Beach

Newly remodeled 1940's cottage just 50 steps to the sand with fabulous beach and ocean views. Enjoy the ocean breeze from your front porch and watch people walk by. Go sunbathing and swimming, take a bike ride or a stroll on the beach, have a glass of wine and witness the most beautiful sunsets. We are located in a quiet residential neighborhood of Ocean Beach. This bright and cozy cottage has everything you'll need to feel at home.

Top guest favorite
The exterior view showcases a spacious parking area beneath a covered carport, surrounded by lush vegetation and vibrant flowers. The property features a neat driveway and a backdrop of rolling hills, enhancing the natural setting. The clear blue sky adds to the inviting atmosphere.
Cottage in La Mesa
4.96 out of 5 average rating, 341 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).

Top guest favorite
A welcoming entrance features a white front door framed by large windows, offering natural light. Two blue chairs are positioned on a small grassy area, ideal for outdoor relaxation. Surrounding plants enhance the calm and inviting setting.
Cottage in La Mesa
4.94 out of 5 average rating, 201 reviews

Private cozy cottage

Set on top of a hill with a wonderful breeze. It is a private, cozy quaint place. Five minutes from the trolley making it easy to go downtown. Close to the 8, 52, 94 & 125 freeways. Downtown San Diego is 20 mins away. If you like to hike we are only 5 minutes from Cowles mountain and other trails. Restaurants and shopping nearby. Beaches are 20 minutes away. We allow house trained pets. Please notify us of pets when booking.

Guest favorite
Cottage in Normal Heights
4.81 out of 5 average rating, 402 reviews

Kensington Cottage Escape- Sleeps 2!

Live and enjoy life like a local in this Chic Cozy Cottage in an upscale Kensington neighborhood! Enjoy the tranquil outdoor dining area along with comfortable queen bed with 1800 thread count sheets. There is ample free street parking. You are only 7-10 minutes to downtown, airport, zoo, Sea World & beaches! Walking distance to tons of restaurants, bars, shops, coffee shops & restaurants! This cottage has AC and heat throughout!

Guest favorite
Cottage in Pacific Beach
4.96 out of 5 average rating, 439 reviews

Beach Getaway on Hornblend

GREAT FOR STAYCATIONS, REMOTE WORKING, GETAWAYS, BUT ABSOLUTLEY NO PARTIES. Beautiful 1 bed 1 bath cottage located just 5 BLOCKS FROM TH BEACH. Queen bed in bedroom and sofa bed in living room. Kitchen is fully equipped and includes ice maker fridge. Bathroom: shower and basic toiletries. Tons of amenities: outdoor shower, boogie boards, beach chairs/towels, pack ‘n’ play, BBQ, firepit and much more. Garage parking included.

Popular amenities for Lakeside cottage rentals

Quick stats about cottage rentals in Lakeside

  • Nightly prices starting at

    Lakeside vacation rentals start at G$25,099 GYD per night before taxes and fees

  • Verified guest reviews

    Over 130 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lakeside rentals

  • 5 Average rating

    Lakeside stays are highly rated by guests—averaging 5 out of 5!