Vacation rentals in Cowles Mountain

A spacious room features light blue walls and a mounted flat-screen television. A small wooden side table with a decorative bowl is positioned near the bed. Natural light enters through sliding glass doors, leading to an outdoor area, enhancing the room's airy feel.

4.98 out of 5 average rating, 55 reviews

La Mesa Hidden Gem: Chic & Cozy!

Kick back in this calm, stylish oasis! This modern, well-maintained home features chic furniture, a unique flush-mounted TV, and a fully equipped kitchen with a dining area. Nestled in a safe, quiet residential neighborhood close to shopping centers, you'll have easy access to multiple freeways. Best of all, you're just a short 20-minute drive from San Diego's beautiful beaches and top hotspots. Perfect for an effortless, relaxing getaway. You will love the free parking and peaceful atmosphere.

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.

4.9 out of 5 average rating, 457 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!

5 out of 5 average rating, 38 reviews

An inviting pool area is shown with a clear blue pool surrounded by tan decking. Lounge chairs are placed nearby, and a pergola offers shaded seating. Lush greenery and distant hillside views enhance the outdoor space under a bright blue sky.

Guesthouse in El Cajon

Casa sunset

Casa sunset Modern 2BR/1BA in quiet Fletcher Hills with hillside views, shared pool, and in-unit laundry. Fully remodeled with stylish decor, full kitchen, coffee machine, fast Wi-Fi, A/C, and free parking. Enjoy sunset views, outdoor seating area for morning coffee or glass of wine sunset, cozy bedrooms, and a bright living space perfect for couples, families, or business trips. Just 20 mins to downtown San Diego and beaches. Clean, comfortable, and move-in ready — your perfect SoCal retreat!

4.86 out of 5 average rating, 199 reviews

A spacious bed is dressed in crisp white linens, complemented by decorative throw pillows. A wooden accent wall adds warmth to the room. A patterned rug covers the floor, and a small dog relaxes nearby. A clothing rack and a set of fresh towels are visible.

Guest suite in San Diego

Wilson's Sunny Retreat

Welcome to Wilson's Sunny Retreat! This is a nice relaxing studio retreat with basic amenities. Newly remodeled private bathroom , in-suite sitting area , coffee bar and refrigerator. Great place to relax and have a coffee. View from private suite and outside sitting area. We are centrally located and 15 minutes or less from everywhere - beaches, San Diego State University, Downtown San Diego and the Gaslamp District, and shopping in Fashion Valley. Close to Mission Trails Regional Park.

4.98 out of 5 average rating, 266 reviews

A bright and inviting living area features a mustard-yellow sofa complemented by patterned cushions. Two armchairs in light grey are positioned around a wooden coffee table, while an acoustic guitar is mounted on the wall. A television is mounted beside large windows that allow natural light to stream in.

Bungalow in La Mesa

Casa de Pueblo - Hot Tub, Fire Pit La Mesa Village

Enjoy a stylish experience at this centrally-located bungalow. Just a short walk to La Mesa Village, where you can enjoy restaurants, coffee shops, boutiques, & more. The outdoor space has a hot tub, fire pit, yard games, & bbq. Hop on the trolley to get anywhere. Traveling with additional friends and family? We have the Casita de Pueblo located at the same location. Check it out under our other listings where you can book both. 20 min drive to the Beach, Downtown, Balboa Park, or Old Town

4.96 out of 5 average rating, 165 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

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

4.88 out of 5 average rating, 228 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.

4.92 out of 5 average rating, 88 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!

4.91 out of 5 average rating, 22 reviews

Private Studio w/ Parking + Kitchen | 15 Min to SD

Relax and unwind at this peaceful and centrally located studio in La Mesa. Perfect for solo travelers or couples, this cozy studio offers a quiet retreat with everything you need for a comfortable stay. Enjoy a private entrance, a comfy queen bed, and a small kitchen for simple meals. Conveniently located approximately 15 miles from San Diego’s main attractions. Peaceful and private space perfect for rest and recharge. Cozy, clean, and thoughtfully designed for a comfortable stay

Superhost

A gas fire pit is surrounded by four outdoor chairs, offering a cozy gathering spot. The expansive backyard provides views of the surrounding hills and valley, with twinkling lights from nearby homes under the twilight sky.

Home in San Diego

4.92 out of 5 average rating, 470 reviews

Spacious home with incredible backyard views

This beautifully appointed home is located in a quiet neighborhood & is central to all San Diego attractions - 5 min to hiking, 15 min to beaches/Zoo/Sea World, 20 min to downtown & 35 min to Legoland. But should you chose to stay in to relax there's plenty to enjoy - Bocce Ball, hot tub, BBQ & gas fire pit. Perfect for families or small groups looking to enjoy San Diego. Please note, if you’re looking to have a party or gathering this is NOT the property for you.

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, 91 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, curated charm. Enjoy tall ceilings, a bright living area with a queen-sized pullout couch, a useful kitchen with basic amenities, a quiet private patio, and a tranquil primary suite with a plush king bed & blackout curtains. Enjoy amenities like fast WiFi, air conditioning, & washer/dryer!

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.