Vacation rentals in Cowles Mountain

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Top-rated vacation rentals in Cowles Mountain

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Top guest favourite
The living area features a gray sofa paired with a coffee table, overlooked by a ceiling fan. Large doors provide access to a balcony with leafy views. Decorative plates adorn the walls, while a tall plant adds a natural touch to the inviting space.
Guest suite in San Diego
4.96 out of 5 average rating, 324 reviews

Find a Country Feel in the City with Rural Views

Sit out in the backyard then come indoors to relish leafy views from a triple-aspect living room. The apartment has a cottage feel with window boxes and wooden fittings. A hanging plant, and white linens provide a calming feeling. Awake to the songs of birds and explore our 1/2 acre of fruit trees, vegetable beds, and landscape. Yet most of San Diego’s attractions are just 5 to 10 miles away. The new kitchen is included in your space so you can prepare your own meals if desired. Cooking equipment included are a convection toaster oven, coffee maker, hot pot, a microwave, and an induction plate, pots & pans, kitchen tools, cutlery and dishes. We also provide coffee, tea, sugar, salt & pepper, cooking oil, and ice. This space is attached to our main home but you’ll have your own separate entrance and private kitchen/ living, bed and bath. We'd love to greet you and show you around when you arrive, but if we happen to miss you will have your own unique door code to get in. We’ve prepared a binder of information for guests and can help you plan for best use of your time. However if you prefer to be on your own we’re fine with that too. We have walked to downtown or to the nearest trolley, but unless you are walkers and out for exercise, you will probably want a car. There are now lots of bikes available for rent, but it will be uphill to get back to the house. Some of our guests have chosen to rely only on Uber, in which case grocery and/or meal delivery are helpful. If you have an afternoon or evening flight you are welcome to store luggage at our house after your 10 AM check out. We are in a hilly residential area with stores, restaurants and bus/ trolley access about 2 miles away, so you'll have the most flexibility if you come by car. If you choose to Uber, you can order groceries or takeout meals to be delivered.

Top guest favourite
A spacious backyard is illuminated by string lights, creating a warm ambiance. Lush greenery, including tall palm trees and banana plants, frames the area. A wooden deck provides an outdoor seating space, while comfortable patio furniture is visible nearby. The sky displays soft pastel colors at twilight.
Home in San Diego
4.97 out of 5 average rating, 375 reviews

SDSU Beach Cottage

Welcome to our stunning SDSU Beach Cottage. Our home is 10 minutes away from everything amazing in San Diego! Our home is Centrally located in San Diego and in a desirable neighborhood. We are steps away from a Local favorite Eatery, Wine Bar, Beer Pub, Natural-Holistic Market, Pizza shop, Liquor Store, Nail shop, and Einstein's Bagels. Play in San Diego or stay and relax in our tropical yard that is set up to entertain you and your family with outside games and Ping Pong. 25 Yr's of age req'd

Top guest favourite
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.
Guesthouse in La Mesa
4.9 out of 5 average rating, 429 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!

Top guest favourite
A bright living area is visible, featuring a mix of modern furnishings including a cozy sofa, a smart TV, and a circular dining table with wooden chairs. Large windows allow natural light to fill the space, highlighting the warm wooden flooring and inviting decor.
Guesthouse in La Mesa
4.97 out of 5 average rating, 102 reviews

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!

Top guest favourite
The exterior of a two-story guesthouse is showcased, featuring a combination of wood paneling and painted walls. A bright white door and two small windows add contrast. The area is complemented by a compact patio set with two chairs and a table on a stone surface.
Guesthouse in La Mesa
4.94 out of 5 average rating, 263 reviews

Fig Tree Bungalow

Enjoy your stay in San Diego in this newly renovated guesthouse. Centrally located about a mile from Hwy 8, Hwy 125, and the Grossmont Trolley Station & Transit Center. Only a 15-20 minute drive to downtown, the airport, the beaches, and most of San Diego's other popular tourist attractions. This cozy, two-story, detached unit is located behind my home, and has its own private entrance and partitioned yard for your enjoyment. There's plenty of street parking directly in front of the house.

Top guest favourite
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
4.86 out of 5 average rating, 197 reviews

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.

Superhost
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
4.88 out of 5 average rating, 217 reviews

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.

Top guest favourite
A cozy living area features a sectional sofa and wooden coffee table, complemented by a television mounted on the wall. Several light sources illuminate the space, including a ceiling fan. Decorative wall art adds a personal touch, while windows allow natural light to brighten the room.
Guesthouse in La Mesa
4.99 out of 5 average rating, 335 reviews

SDCannaBnB #1 *420 *parking *dog-friendly *hot tub

Welcome to SDCannaBnB - San Diego's premier cannabis-friendly rental!   Our casita is newly remodeled with luxury ammenities.  We proudly cater to the cannabis community and non-users alike.   Our casita has HEPA air purifiers, is fully ventilated and receives deep cleanings between each guest.  This ensures that every guest checks into a clean, fresh-smelling place that feels like home.   Our casita is located in our quiet, fully fenced in backyard, close to San Diego's attractions

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, 460 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.

Guest favourite
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.
Guesthouse in La Mesa
4.94 out of 5 average rating, 179 reviews

San Diego Newly Built Private Guesthouse (Sleep 4)

Newly built one-bedroom private guesthouse w/view of Cowles Mountain and separate street entrance. Living room has queen futon. A 50" smart TV with YouTube TV. Free high-speed Wi-Fi. Kitchen with refrigerator, stove, oven, microwave, dishwasher, toaster, and Keurig coffee machine. Bedroom has queen bed and 40" smart TV. Bathroom has large shower and electronic bidet. Washer/dryer. Allow small pets up to 35 lbs. for $20 fee.

Top guest favourite
A pool table with a blue felt surface is positioned under a covered outdoor area, surrounded by lush greenery. The scene includes palm trees and various plants in the background, providing a serene view of the surrounding landscape.
Guest suite in El Cajon
4.96 out of 5 average rating, 276 reviews

NEW! Valley View Garden Suite

Kick back, relax, and enjoy the view in this delightful, 1 bedroom w/ livingroom suite. 20 mins from beaches, downtown, Sea World, Zoo. 2 mi to Grossmont Hosp, 8 mi to SDSU, 3 mi to Gillespie Field The suite is attached on the side of a house. But it is completely separate and has its own private entrance. The back patio & side breezeway are just for you . Free, reserved, off-street parking.

Top guest favourite
A view of the inviting swimming pool surrounded by a spacious patio. Natural rock elements and vibrant landscaping enhance the outdoor area. The multi-level deck is visible, offering seating options and picturesque canyon surroundings under a clear blue sky.
Home in La Mesa
4.9 out of 5 average rating, 200 reviews

The Queen House

Welcome to Endless Summer, your ideal family retreat! This beautiful 4-bedroom, 2.5-bath home is just 15 minutes from Downtown San Diego, near attractions like Petco Park, the San Diego Zoo, and local beaches. Located in Mount Helix, La Mesa, enjoy stunning canyon views and a refreshing swimming pool with a waterfall. Experience a unique stay at a home that has it all!

Popular amenities for Cowles Mountain vacation rentals