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Vacation rentals with a pool in El Cajon

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in El Cajon

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

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Top guest favorite
Two red Adirondack chairs are positioned under a covered patio, facing a serene backyard with a pool. Lush greenery surrounds the area, creating a tranquil atmosphere. A BBQ room and various seating arrangements are visible beyond the pool, enhancing the outdoor retreat experience.
Guesthouse in La Mesa
4.99 out of 5 average rating, 135 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

Guest favorite
The property features a spacious backyard with a heated pool surrounded by lounge chairs. Palm trees line the perimeter, and soft lighting illuminates the outdoor area during sunset. The two-story house overlooks the pool, creating an inviting atmosphere for relaxation and gatherings.
Home in La Mesa
4.95 out of 5 average rating, 215 reviews

XTRA 10% OFF until Nov: Pool, outdoor fire pits, c

Find your family's dream spot in San Diego! Our cozy house sits on a quiet hill, offering privacy and amazing sunset views. Dive into our pool year-round (heating at an additional cost), roast marshmallows by the fire, and cook up fun meals together. With 3 bedrooms and 2 bathrooms, it’s perfect for families, accommodating up to 9 guests. Plus, we're close to all the best attractions. Want a vacation you'll always remember? Send us a message to make it happen! 🌅🏠 We have 3 comfy beds that can

Guest favorite
A living room features a luxury hanging chair suspended from the ceiling. Natural light filters through sheer curtains, illuminating a cozy seating area with a plush sofa and wooden coffee table. A 50” television is mounted above an elegant fireplace, enhancing the room's comfort.
Home in City Heights
4.93 out of 5 average rating, 124 reviews

Designer Luxury Rental With Pool

Welcome to Wander Haven, a luxury central rental. With it’s on trend design, custom built stock tank pool, array of amenities and thoughtful touches throughout, you won’t ever want to leave. But when do you do decide to venture out and explore all that beautiful San Diego has to offer, you will find the central location gets you to anywhere you want to be in minutes. You’re 15 minutes or less from beaches, downtown, balboa park, sea world, the zoo and hundreds of amazing bars and restaurants.

Guest favorite
A refreshing pool is surrounded by a spacious deck, showcasing lounge chairs and a large umbrella. Expansive views of the city and distant hills are visible under clear blue skies, creating a serene outdoor retreat.
Bungalow in El Cajon
4.86 out of 5 average rating, 112 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! “Enjoy the hillside pool—just coordinate with Johnny for your own private swim.”

Top guest favorite
A cozy living area showcases a modern yet rustic design, featuring a large wooden table and comfortable seating. Warm lighting from pendant fixtures complements the natural wood accents on the walls, while a decorative fireplace enhances the inviting atmosphere.
Farm stay in Lakeside
4.96 out of 5 average rating, 376 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.

Guest favorite
A sunny outdoor view showcases a vintage red and white travel trailer surrounded by tropical palm trees. A hot tub is positioned on a wooden deck, complemented by potted plants and cozy seating nearby.
Camper/RV in La Mesa
4.97 out of 5 average rating, 191 reviews

“Pineapple Express”

Aloha! If your looking for a relaxing & mellow vibe, We invite you to stay the night in our cozy 1948 16ft Travelo travel trailer, “The Pineapple Express” Enjoy your private pool and hot tub, behold a beautiful San Diego sunset from the hillside deck or pull up a stool at the Tiki Bar for your morning coffee. We now have an outdoor gas grill, hot water pitcher, microwave, mini fridge and utility sink for food prep! Hablamos español Deaf friendly 🏳️‍🌈. Alycen ASL fluent.

Top guest favorite
This open concept studio features a light-filled seating area with a plush sectional sofa adorned with decorative pillows. A well-equipped kitchenette and a dining area with bar stools are present. The spacious bed is positioned in the background, complemented by soft lighting and neutral decor.
Guesthouse in La Mesa
4.99 out of 5 average rating, 103 reviews

Private Balcony! Sunset & SunriseVIEWS!

~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

Guest favorite
A dining space features a round table with four white chairs, complemented by a potted plant. Large glass doors slide open to reveal expansive views of the backyard, pool, and surrounding hills, with soft evening light illuminating the scene.
Home in Spring Valley
4.96 out of 5 average rating, 178 reviews

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)

Top guest favorite
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 Lake Murray
4.96 out of 5 average rating, 130 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.

Guest favorite
A serene pool area features crystal-clear water, with striped lounge floats anchored in the center. Surrounding palm trees offer shade, while natural stone accents decorate the pool's edge. The sound of a waterfall can be faintly heard, contributing to a calming atmosphere.
Guest suite in La Mesa
4.89 out of 5 average rating, 244 reviews

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.

Guest favorite
A residential property is featured, surrounded by lush greenery and tall palm trees. The house, characterized by a tiled roof and stucco exterior, is set on a corner lot, showcasing a well-maintained garden with a variety of plants and decorative stones.
Guesthouse in Tierrasanta
4.87 out of 5 average rating, 170 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 favorite
The sunset illuminates the sky with vibrant hues, casting a warm glow over the swimming pool and surrounding backyard. Outdoor seating is arranged near the pool, complemented by lush greenery and a large rock. The scene evokes a sense of tranquility.
Guest suite in La Mesa
4.88 out of 5 average rating, 187 reviews

Mountain Retreat Ocean View-Great for Staycation

Located on the historic Mount Helix. High above the valley below, with an exquisite view of the ocean evening sunsets through the beautiful valley. Beautiful Mountain Retreat with ocean view. Private entrance. Full kitchen (toaster oven only). Access to shared pool. Beautiful sunsets. Newly remodeled. (NO SMOKING) Your Co-host lives upstairs and is available for you if needed! The backyard is a shared area.

Popular amenities for El Cajon rentals with a pool

When is the best time to visit El Cajon?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$62,598 GYDG$59,876 GYDG$66,785 GYDG$58,620 GYDG$64,901 GYDG$75,159 GYDG$84,790 GYDG$76,416 GYDG$68,460 GYDG$64,692 GYDG$61,342 GYDG$65,110 GYD
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Quick stats about vacation rentals with a pool in El Cajon

  • Total vacation rentals

    Explore 140 vacation rentals in El Cajon

  • Nightly prices starting at

    El Cajon vacation rentals start at G$6,281 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,450 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    140 of El Cajon vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across El Cajon rentals

  • 4.8 Average rating

    El Cajon stays are highly rated by guests—averaging 4.8 out of 5!

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