Vacation rentals with a pool in Lakeside

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lakeside

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Superhost

Guesthouse in Escondido

4.91 out of 5 average rating, 772 reviews

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.

Top guest favourite

Guesthouse in La Mesa

4.99 out of 5 average rating, 122 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

Top guest favourite

Guesthouse in Kit Carson

5 out of 5 average rating, 158 reviews

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.

Guest favourite

Guesthouse in Ramona

4.92 out of 5 average rating, 359 reviews

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.

Guest favourite

Farm stay in Lakeside

4.96 out of 5 average rating, 369 reviews

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.

Top guest favourite

Guest suite in La Mesa

4.94 out of 5 average rating, 119 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!

Top guest favourite

Guesthouse in La Mesa

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

Top guest favourite

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.

Superhost

Hotel room in Ramona

4.84 out of 5 average rating, 130 reviews

One Bedroom Condo in San Diego Country Estates

San Diego Country Estates is nestled against the foothills near the quaint and historic towns of Ramona and Julian. Resort guests enjoy “The Good Life,” a perfect blend of active play and total relaxation with a variety of indoor and outdoor activities. A resort fee of $27.00/night is included in the total price shown on Airbnb. This fee covers parking, Wi-Fi, and access to on-site amenities. Please read through full House Rules prior to booking.

Guest favourite

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!

Guest favourite

Guesthouse in La Mesa

4.91 out of 5 average rating, 187 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.

Guest favourite

Bungalow in El Cajon

4.86 out of 5 average rating, 107 reviews

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!