Vacation rentals with a pool in Rancho San Diego

4.99 out of 5 average rating, 121 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

4.89 out of 5 average rating, 266 reviews

Villa in La Mesa

Private Villa: Pool, Slide & Hot Tub – $799 Sale

🍂 Fall/Winter Sale! ❄️ 🎉 Sale: $799/night (Reg. $899 - $999) 🗓️ Valid through Feb 28, 2026 🌴 Perfect for holiday get-togethers (up to 16 people)! ✅ Taxes paid by owners! (Cleaning and Airbnb fees apply.) 💬 Some of our reviews: 🌅 "Perfect for our group trip—amazing views and outdoor spaces." 🏊‍♂️"Kitchen, pool, and hot tub made our stay unforgettable." 🎉 "So many fun activities—swimming, jacuzzi, pool slide, and more." 🏡 "This was one of the best Airbnb properties we've ever been to."

4.96 out of 5 average rating, 366 reviews

Farm stay in Lakeside

The Outside Inn at The Tipsy Goat Ranch

Nestled near Iron Mountain, a popular hiking destination, and less than 16 miles from San Diego's pristine beaches and local attractions, enjoy all SD has to offer in a one-of-kind farm-to-beach experience. Immerse yourself in a rarely seen side of San Diego you won't find anywhere else. Based on adventure, wrapped in luxury, a deep love for nature and the creatures it inhabits (mini goats, alpacas, babydoll sheep, lop bunnies, and chickens), it'll be a tranquil getaway you'll never forget.

4.94 out of 5 average rating, 117 reviews

Guest suite in La Mesa

Birdsong Suite | Family-friendly getaway

Welcome to our cozy and spacious Birdsong Suite! Tucked in the lush foothills of Mt Helix, on a private road, this private one-bedroom unit will accommodate up to 6 travelers (perfect for a family!). The pool and hot tub are a delight after a day of exploring. The San Diego Zoo, downtown, and Balboa Park are a mere 20 minute drive. Downtown La Mesa is only 5 minutes by car and has restaurants to suit every taste. We look forward to having you stay at our peaceful getaway!

4.99 out of 5 average rating, 100 reviews

Hilltop Haven~BALCONY~Sunset & Sunrise VIEWS!~

~PANORAMIC VIEWS~ ~PEACEFUL & PRIVATE~ ~CENTRAL LOCATION~ ~XL BALCONY~ ~POOL/SPA ADD ON PACKAGE~ OCEAN, Mountain, Harbor, & Valley views~to Pt Loma & Coronado! Historic Mt Helix neighborhood. Balcony with panoramic views~ an outdoor living space! Private entrance, 1 Driveway parking space Ask about our POOL/SPA/LOUNGE-available as an ADD ON fee package only~Scroll down for details on EXTRA deposits/fees & approval terms that apply NON SMOKING/VAPING property indoor & out

4.96 out of 5 average rating, 154 reviews

Home in Spring Valley

Upscale Resort House /Views, Saltwater Pool/Spa !

This home offers Saltwater pool and Spa. Saltwater pools and Spa produce softer-feeling water. breathtaking views from its location high in the hills overlooking Rancho San Diego. In the backyard you can enjoy the sunrise from the private pool or deck or practice your putting on our putting green. The House is a mid-century modern home perched above the City. It's great for groups seeking easy access to San Diego's highlights (15 to 20 minutes to Beaches and Downtown)

Guesthouse in Lake Murray

4.96 out of 5 average rating, 116 reviews

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.

Guesthouse in Tierrasanta

4.87 out of 5 average rating, 163 reviews

Fig Tree Cottage

The private upstairs addition to our home was built new Spring of 2017. Sitting over our garage, it is a cozy 500 sqft & offers guests a quaint & quiet place to relax. With well appointed furnishings & thoughtful decor, Fig Tree Cottage offers everything you need to enjoy all the comforts of home. Just 15 min away enjoy the beautiful beaches of La Jolla along with some of the best restaurants and boutique shopping San Diego has to offer!

4.88 out of 5 average rating, 354 reviews

Guest suite in Bonita

Resort-Style Living, Pool, Close to All San Diego

Nestled in a quiet, discreet neighborhood, our private air-conditioned studio offers a safe and serene retreat. Attached to a stunning ranch-style executive home, it features an amazing pool for your relaxation. Conveniently located near the Olympic Training Center, downtown San Diego, Comic-Con, major attractions, concert venues, beaches, the airport, and Mexico. Enjoy a complimentary butler tray that includes coffee, tea, and snacks.

4.91 out of 5 average rating, 186 reviews

La Cabana

Perfect getaway for the wandering individual, couple, or young family. This rustic casita is surrounded by beautiful mountain and ocean views! Enjoy swimming in the pool, stargazing, lounging, or casual day trips around San Diego (All the amenities are shared with the main house) . The casita has one queen bed and a sofa bed, small kitchenette. Plenty of parking in driveway. Please read entire listing for details.

4.86 out of 5 average rating, 107 reviews

Bungalow in El Cajon

Stylish Relaxation-Panoramic Views-Private OASIS!

~BRAND NEW DRIVEWAY~Perched high on granite hills, our comfy, stylish bungalow is perfect for a quiet getaway in San Diego. Brew your morning coffee and stroll to the pool to let the expansive views of the city fuel your daily adventures. Host a barbeque in the spacious, private backyard after your day at the beach. Cozy up in the recliner loveseat and enjoy the big screen 4k smart TV (with cable). 420 Friendly!