Holiday rentals with a pool in Rancho San Diego

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

Infinity Poolside Apt. In San Diego Wine Country

158 Perfect 5.0 Reviews-Amazing views, peaceful and beautiful space in a wine country setting. A perfect setting to celebrate a special occasion and create memories. Amazing sweeping views of wine country, lake, golf course and mountains on the 14th green of a golf course with full access to the estate pool, spa, covered parking, EV charger w/private European park. Large luxury suite with a Kitchen, Sitting Room, Bathroom, Steam shower/Sauna and bedroom with luxurious robes, linens and towels.

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."

Former ManCave with Pool & Spa!

Our 'MAN CAVE' is now a bright, spacious basement studio with a large stone and marble OUT-DOOR SHOWER We're freeway close and very accessible to the sites of San Diego: Downtown in 10-15 minutes; Beaches, San Diego Zoo, Sea World all within 15-20 minutes. An adjoining space is also an AIRBNB one bedroom suite. Great for traveling friends or as an alternative place to consider for your stay. Just click on our 'PROFILE PICTURE' to see our 'Comfy & Cozy Flat' plus our many reviews.

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!

Deluxe Escape~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

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.

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.

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!