Holiday houses in Cowles Mountain

A serene outdoor space showcases a sparkling pool adjacent to a jetted hot tub, with canyon views stretching in the background. A glass fence enhances the vista, and the surrounding landscape features palm trees and gentle hills under a clear blue sky.

4.98 out of 5 average rating, 116 reviews

ModernCoastal I View I Pool ITub

Spectacular canyon views are the backdrop to this stunning, modern newly renovated San Diego home! The jetted hot tub with water falling in the sparkling pool, the natural light streaming through the french doors, huge screened folding door, and skylights, the beautiful Great Room with the inviting living room, gourmet kitchen, indoor/outdoor dining, comfy beds, spectacular rooms & bath, sunset vista point, outdoor BBQ & backyard loungers and daybed are all designed to get you in vacation mode!

4.97 out of 5 average rating, 148 reviews

Guest suite in San Diego

Aloha Private Suite | Central Location!

Welcome to the Aloha Private Suite, a tropical inspired stay in the heart of San Diego. This bright, ocean inspired private guest suite features a private entrance, a comfy queen bed, and a relaxed island feel. Centrally located 15 minutes from the airport and beaches, and close to the stadium and San Diego’s main neighborhoods. Whether you are visiting the city, heading to the beach, or looking for a quiet place to unwind, the Aloha Private Suite offers a comfortable and convenient stay.

4.96 out of 5 average rating, 181 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 La Mesa

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.

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.

4.87 out of 5 average rating, 239 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, 102 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 spacious living area is highlighted by a light-colored couch, a coffee table, and an area rug with a leaf pattern. An open layout leads to a dining area with wooden chairs and a kitchen visible in the background, featuring modern appliances and bright windows.

4.92 out of 5 average rating, 100 reviews

Your SD Home Away from Home-Big Family Retreat

Not just a stay—a space to belong. This 4BR San Diego retreat is designed for real connection, with room to breathe, soft touches throughout, and everything you need to feel at home from the moment you arrive. Laugh late into the night, greet sunlit mornings with coffee in the garden, and linger over unhurried meals. Become a local in one of San Diego’s safest, quietest neighborhoods—your home base for memory-making, firelit stories, and the kind of moments that stay with you.

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, 479 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.

4.96 out of 5 average rating, 314 reviews

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

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. The rest of the backyard is private for owners only. Free, reserved, off-street parking.

4.95 out of 5 average rating, 196 reviews

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

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, 401 reviews

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 Del Cerro

SDSU Beach Cottage

Welcome to our charming SDSU Beach Cottage! Centrally located in a desirable San Diego neighborhood, you're just 10 minutes from many of the city's top attractions. Steps away, you'll find popular local dining, a wine bar, pub, natural market, pizza shop, nail salon, liquor store, and Einstein Bros. Bagels. Enjoy San Diego's best or unwind in our tropical backyard featuring outdoor games and ping pong. Minimum age to book: 25.

4.99 out of 5 average rating, 133 reviews

An open-concept living area is highlighted by vaulted ceilings and natural light from large windows. A spacious L-shaped sofa is positioned around a coffee table, facing a wall-mounted TV above a modern fireplace. Nearby, a dining area can be seen through an archway.

Home in El Cajon

Spacious & Fun | 5br, 4.5ba | Hot Tub | Views

Experience sunny San Diego from this 5 bedroom, 4.5 bathroom foothill home. Wake up to panoramic views of the surrounding hillsides and gather in the spacious living and dining rooms. The home is conveniently located just 15-20 minutes from San Diego's famous beaches and top attractions. After a day of exploration, unwind in the backyard area featuring a hot tub, fire pit, pool table, and life-sized chessboard.