Vacation rentals in Cowles Mountain

Two red Adirondack chairs are positioned under a covered patio, facing a serene backyard with a pool. Lush greenery surrounds the area, creating a tranquil atmosphere. A BBQ room and various seating arrangements are visible beyond the pool, enhancing the outdoor retreat experience.

4.99 out of 5 average rating, 134 reviews

Private 1 BR Paradise retreat

Private, yet central. It is your exclusive paradise retreat to enjoy from your spacious 1 bedroom guest house located on the lower level of our home. Hang out in the expansive and private backyard with pool, different sitting areas and covered BBQ room. Or maybe a workout in the gym. Centrally located in the Village of La mesa. Just a 1/4 mile jaunt into the quaint village with its numerous assortments of dining options, stores and trolley station. Freeway close to beaches, downtown and airport

4.99 out of 5 average rating, 170 reviews

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

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

The exterior of a historic stone cottage showcases a rounded structure with large, circular windows. Native plants and decorative rocks surround the entrance, highlighting the natural landscape. The name 'Anna' is displayed on a rustic wooden sign, further enhancing the cottage's character.

4.89 out of 5 average rating, 388 reviews

Anna's Historic Stone Cottage w/panoramic View!

Welcome to Anna's Historic Stone Cottage! The 110 year old cottage has been transformed into the perfect combination of romantic and rustic for a dream-worthy getaway. The 280sq ft cottage features stunning, panoramic views of the San Diego skyline while offering rooftop seating for sunrise and sunset viewing. The Cottage is conveniently located 20 minutes from the world famous San Diego zoo and most other must-see, tourist spots. Amenities for special occasions offered too. Check out our menu!

4.97 out of 5 average rating, 37 reviews

A stylish bathroom features a floating double vanity with wooden drawers and a large mirror above. Adjacent, a curbless walk-in shower showcases elegant tile work and both rain and handheld showerheads, completed with modern gold fixtures and a glass enclosure.

Guest suite in San Diego

Cozy Resort-Style Retreat

The perfect getaway for 1–2 guests! This private unit features a master suite that offers resort-style comforts, complete with a luxurious bathroom and a spacious patio. Nestled in a quiet, peaceful neighborhood just minutes from Cowles Mountain, Lake Murray, Mission Trails Golf Course, and SDSU. You’ll enjoy easy access to local dining, shopping, public transit, and freeways. Downtown San Diego, the Gaslamp Quarter, and airport are just a short drive away, a great home base for work or play!

Guesthouse in Spring Valley

An Airstream is positioned on a hillside, surrounded by lush greenery and desert plants. Lounge chairs and a shaded patio area are visible, providing a space for relaxation. The backdrop features rolling hills under a clear sky, highlighting a peaceful and private setting.

4.98 out of 5 average rating, 393 reviews

Nature Escape •Sauna•SoakTub•Views+Zoo pkg add-on

Nestled in a hillside canyon, a short drive outside the city, this Airstream glamping retreat offers incredible panoramic city, sunset & nature views. Modern comforts include A/C & heat, a full kitchen, fast Wi-Fi, and convenient off-street parking on a gated estate. Cozy up by the firepit as the city sparkles below or try your swing at the golf tee. Reconnect & recharge with your own outdoor hot soaking tub, open-air rain shower, and wood-fired sauna - the perfect retreat for nature lovers!

4.87 out of 5 average rating, 207 reviews

A serene outdoor space features a salt-water pool surrounded by a concrete patio and manicured grass. An umbrella provides shade over the poolside area, with lush greenery and mountains visible in the background under a partly cloudy sky.

Home in San Diego

Bright and spacious home with views, pool & spa.

This beautiful and recently remodeled, open-floor plan home is conveniently located directly across from Cowles Mountain, one of San Diego's most visited hiking trails. Each bedroom has its own full bathroom. Perfectly located for the outdoorsy family. Tons of hiking and mountain bike trails are just across the street. Only 15 min. away from beaches, zoo, & Sea World. Gaslamp/Downtown is only 20 min. by car. After a day of exploring, come home to a newly-built, salt-water pool and spa.

4.89 out of 5 average rating, 55 reviews

A dining area is highlighted by a round wooden table surrounded by six wooden chairs. A cozy blue sofa is positioned nearby, with large glass doors opening to a pool area. Natural light enhances the space, complemented by a modern pendant light overhead.

Home in San Diego

San Diego Oasis- A Retro Retreat w/ King Size Bed!

Welcome to San Diego Oasis, a retro retreat--a mid-century modern oasis in sunny San Diego! This stylish home combines classic charm with all the modern upgrades you desire. Unwind by the sparkling pool, enjoy a friendly game of air hockey or corn hole, board games or enjoy s'mores around the gas fire pit . The retro retreat is the perfect blend of comfort, convenience, and timeless design. SD's most popular attractions are all within a 20-30 minute drive. Only 20 minutes to the beach!

A bright living area features a comfortable brown couch adorned with colorful cushions. A white table accommodates seating for four, while vibrant wall art enhances the atmosphere. A retro-style refrigerator adds a pop of color, and natural light floods through the windows.

5 out of 5 average rating, 58 reviews

Stylish San Diego Guesthouse - Walk to the Lake!

Our vibrant guest house in La Mesa is located minutes from SDSU, Lake Murray, La Mesa Village, and central San Diego! This colorful retreat combines modern comforts with serene, expertly curated charm. Enjoy tall ceilings throughout, a bright living area with a queen-sized pullout couch, a useful kitchen with basic amenities, a serene private patio, and a tranquil primary suite with a plush king bed & blackout curtains. Enjoy amenities like fast WiFi, air conditioning, & washer/dryer!

4.96 out of 5 average rating, 125 reviews

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.

Guesthouse in San Diego

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

This is the 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 Downtown, La Jolla, Beaches, Zoo, Sea World & Convention Center. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes await you inside. Everything you need for memorable vacation! No smoking or vaping on the property.

5 out of 5 average rating, 58 reviews

A cozy living room area is displayed, featuring a gray couch adorned with decorative cushions, a comfortable armchair with plush accents, and a wooden coffee table. Natural light fills the space through a window with blinds, complemented by wall art showcasing colorful sea motifs.

Guesthouse in San Diego

Lrg 1 bedrm unit Full Kitchen by SDSU & Cowles Mtn

Escape your worries in this spacious, separate unit that is approximately 600 square feet located between scenic hiking trails and downtown attractions. It is attached to the rear of the property with a common wall, yet separate with a private entrance. You are 20 minutes from beaches and downtown and 10 minutes to SDSU. It is walking distance to Cowles Mountain and Mission trails. Nearby is historic La Mesa Village famous for great dining and shopping.

A vibrant sunset casts shades of orange and pink across the sky, viewed from a residential street. Palm fronds frame the scene, while neighboring homes and trees are softly silhouetted against the colorful backdrop.