Holiday rentals with a pool in Lakeside

Hilltop cabin retreat with lake & mountain views

Rustic hilltop cabin overlooking Lake Hodges. Surrounded by open canyons & mountains, you will feel like you're a million miles away from everything as you take in the views from the cabin, deck or the outside shower, swim in the saltwater pool, or relax by the fire bowl. A short walk to lake with boating, fishing & miles of hiking/mountain biking trails. Property offers swimming pool, fire bowl, and shaded arbor. SD Zoo Safari Park, wineries, breweries, & ocean beaches all within easy reach.

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

Wine Country Retreat - Tranquility Hottub/Views

Our famed Wine Country Retreat is back online! (LTR for the last year) Take the back roads scenic drive 50mins up the hill from San Diego and enjoy some much needed quiet and comfy tranquility. Right in the heart of San Diego Wine Country, it’s a rather well appointed place situated on 10 private acres that overlooks expansive green space. With few neighbors in any direction, you can either sleep with the windows open and wake early to roosters crowing, or close the windows and sleep til Noon!

Cozy Spanish Casita w/ Mountain View in Ramona

Perfect getaway for wine lovers and hikers in this serene spanish ranch style casita with beautiful orchard & mountain views! Enjoy visiting Ramona's local wineries, hiking Mt. Woodson or Iron Mountain, swimming in the pool, stargazing, golfing, a day trip to Julian, or San Diego Wild Animal Park. The Casita has one private bedroom with a king bed and a cozy upstairs loft with a full bed located in a second room. Casita sits on top of a hill with the main house. Please read entire listing.

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.

Hacienda de las Campanas (Bell Hacienda)

Stay in classic, historic California Hacienda style! A complete, self-contained apartment--your casita--within our beautiful, historic Monterey Spanish Revival hacienda home, situated on a half acre. The apartment has a separate, private entrance and includes a sunlit living/dining room opening on to a large swimming pool; a small kitchenette; and a private bedroom and bathroom down your own hallway. The suite is tastefully furnished consistently with the historic Spanish architecture.

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

This is your 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 beaches, Downtown, La Jolla, Zoo, Stadiums, Sea World, Convention Center + more. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes and furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

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!

Comfy, Cozy Flat With Pool & Spa!

Our flat has a patio that enjoys great sunsets. We are freeway close to all, easy in and easy out!! You’ll love the place because of the comfy bed, space, patio and access to pool and spa. Also, the yard can be enjoyed for relaxing, eating, bonfires, horseshoes and cornhole. An adjoining space is also an AIRBNB studio suite. Great for traveling friends or as an alternative place to consider for your stay. Look for Foemer man Cave with Pool And Spa.

Tranquil Poolside Studio

Quiet Poolside Studio Suite! Perfect for visiting family in La Mesa or enjoying everything San Diego has to offer! Please note: this is not a party house. Private side entrance to a relaxing poolside studio. Very quiet with TV, and full kitchen. Comfortable queen size bed and sofa that can sleep one more person comfortably. We are 20 min to the beach, or relax and enjoy the pool! Close to SDSU and easy freeway access to anywhere in San Diego.

Paradise Lagoon Resort Style Pool Getaway

A unique one-of-a-kind poolside oasis with a tiki bar and spacious 4-bedroom house Welcome to Paradise Lagoon! This stunning home is the perfect place to relax and unwind with your family and friends. With its private pool (*best in San Diego), tiki bar, game room, and roomy 4-bedroom layout fit for multiple families, you'll never want to leave. Come make some magical memories with family and friends in your own resort style vacation home.

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.