Holiday houses in Cowles Mountain

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.

4.91 out of 5 average rating, 464 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!

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.

4.98 out of 5 average rating, 125 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!

4.99 out of 5 average rating, 175 reviews

A spacious sleeping area is featured, highlighted by a plush green bedspread atop a comfortable bed. Flanking lamps on either side provide soft illumination, while a large round mirror reflects the room's light. Decorative artwork and potted plants add a serene touch.

Guest suite in La Mesa

Emerald Suite Spa Experience with Sauna & Desk

Soothe your senses and unwind in your private spa retreat, featuring a restorative sauna, a huge soaking tub, and the refreshing scent of eucalyptus aromatherapy. Sink into a luxuriously comfortable king bed, surrounded by a calming ambiance. Thoughtful touches like plush robes and a chilled filtered water dispenser elevate your experience. Set in a tranquil neighborhood with easy access to San Diego’s highlights, this sanctuary offers the perfect blend of relaxation, rejuvenation, and comfort.

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.

4.96 out of 5 average rating, 171 reviews

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.

4.98 out of 5 average rating, 112 reviews

Home in Serra Mesa

5 Min > Convoy | King Bed | Parking | Private Yard

Experience the beauty of San Diego at prime location, and inviting home 5 min → All freeways 9 mins → Balboa Park 13 mins → Petco Park / Gaslamp Quarter 14 mins → Airport 15 mins → La Jolla Shores Park 16 mins → USS Midway Museum 18 mins → Beach / Coronado 25 mins → Lagoon Trails ⭐️ "One of the best stays in SD" ⭐️ • Extreme Privacy & Fully Fenced • 2 Vehicles Private Parking • Large Patio + BBQ • Stocked Kitchen • Washer + Dryer Add to your wishlist - click ❤️ in the upper-right corner

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.

4.88 out of 5 average rating, 232 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.

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.

4.92 out of 5 average rating, 93 reviews

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 bedroom features a spacious bed adorned with a textured blanket and decorative pillows. The wall behind the bed is designed with bold black shapes, complemented by a macramé hang and soft lighting from bedside lamps. Natural light streams through a nearby window.

4.99 out of 5 average rating, 122 reviews

Tranquil Airy San Diego Home

Welcome to your peaceful home-away-from-home! This charming & spacious TWO STORY house offers the perfect blend of comfort, privacy, and convenience. Nestled in a quiet neighborhood cul-de-sac, yet just minutes drive from everything, this is the ideal spot for both relaxation and exploration. It's the perfect space for a couple, a group of friends, a small family (with kids aged 12 & above) or remote workers looking to relax and enjoy San Diego’s beautiful weather year round.

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.

4.92 out of 5 average rating, 474 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 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.

4.95 out of 5 average rating, 190 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.

4.97 out of 5 average rating, 156 reviews

The studio features a spacious bed adorned with a plush white quilt. A decorative basket with a bottle and glass rests on the bed. A cozy love seat is positioned nearby, complemented by soft grey curtains that frame the window, allowing natural light to illuminate the room.

Home in El Cajon

Suite Charles Way: A Cozy Fletcher Hills Studio

This newly remodeled spacious studio retreat features a private courtyard with barbecue, kitchenette, a brand-new California King bed, and a reclining love seat with charging ports. Enjoy a relaxed cabana vibe, a charming neighborhood and treetop views with easy access to all your favorite San Diego destinations. Within minutes from Grossmont Sharp Hospital, Grossmont Center, the trolley and Grossmont College.

A cozy living room features a dark brick fireplace beneath a large flat-screen TV. Two teal armchairs and a brown sofa surround a low coffee table, with a colorful area rug adding warmth. A sliding glass door leads to a bright outdoor space.