Holiday rentals with a pool in El Cajon

4.99 out of 5 average rating, 164 reviews

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.

Guest house in La Mesa

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

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.

4.95 out of 5 average rating, 239 reviews

Family Pool Retreat + Gym, Fire Pits, Views (Sleep

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

4.98 out of 5 average rating, 106 reviews

The vibrant sunset sky is filled with hues of pink, orange, and purple, reflecting beautifully in the calm water of the pool. Palm trees stand in silhouette, framing the picturesque view of the surrounding mountains and valleys.

Guest house in Jamul

San Diego Mountain Retreat

3 bedroom 1 bathroom loft (2 separate sides) open concept guest house. Very peaceful East San Diego getaway. Enjoy beautiful ocean and Mountain Views during the day then relax in the jacuzzi with breath taking sunsets and the city lights at night. Best views in San Diego! Only 25 minutes from the SD airport and beaches. Minutes away from 2 local wineries and casinos. House sleeps 6 but you can invite guests up for the day for a fee. Event prices will be discussed per event. We live in main home

4.86 out of 5 average rating, 117 reviews

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

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.”

4.96 out of 5 average rating, 155 reviews

A spacious living area features large floor-to-ceiling windows showcasing panoramic views of the outdoor pool and surrounding landscape. A pool table is positioned in the center with comfortable seating nearby. Natural light floods the room, highlighting the modern decor and open layout.

Villa in El Cajon

@Fantastic villa, giant pool, guest house, golf !

This unique fantastic villa with a separate pool house sitting on 1 acre with a spacious living space with large windows. Main house has 4 bedrooms with 2 baths, and a guest house has 1 bedroom with 1 bath. +8 car parking, nice privacy and a fantastic view! Brand new giant size SALT pool with huge size jacuzzi, pool toys, golf zone, a huge grass event field, game field, pool table, foosball, ping pong, Nitendo,2 fire pits and more! Truly one-of-a-kind property don’t miss out! ToT:COSD-00749

Guest house in Lake Murray

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.

4.97 out of 5 average rating, 156 reviews

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

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

A spacious outdoor area features a swimming pool, accompanied by colorful lounge chairs and a large umbrella for shade. A unicorn float is visible in the water, with potted flowers adding a touch of vibrancy. The home's façade offers multiple windows and seating options nearby.

4.99 out of 5 average rating, 194 reviews

Mid-Century Style Family House with Spa

This home is the epitome of 1950’s luxury. A perfect family oasis, you won’t even want to leave the property. Beautiful Mt. Helix mid-century modern family home with incredible views, designed by architect of original Las Vegas Desert Inn situated on nearly an acre. Less than 20 minute drive to beaches/Zoo/Sea World/Downtown. With a swimming pool, jacuzzi, and AC. Surrounded by orange, lemon, pomegranate trees and herb garden. No loud parties please, this is a quiet community.

An outdoor seating area is equipped with a sectional couch surrounding a stone fire pit, with flames flickering invitingly. A large dining table offers ample seating. The heated pool glistens in the background, surrounded by lounge chairs and shaded umbrellas.

4.96 out of 5 average rating, 108 reviews

Family Fun Oasis Pool Spa and Game Room

Exceptional home w/heated pool and spa in a quiet neighborhood; kitchen has everything you need and more! Perfect for families with kids of various ages or multiple families. What to Expect: - Heated pool w/safety cover - Hot tub - Game Room - Trampoline - Jungle gym - Baby/toddler supplies (pack N play/High Chair) - Spacious master suite. - 20 mins to the beach, the San Diego Zoo, Balboa Park, Sea World, Little Italy and downtown San Diego and all that it has to offer!

4.96 out of 5 average rating, 206 reviews

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

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)

Superhost

4.85 out of 5 average rating, 106 reviews

Mountain View• Solar-heated Pool •HotTub •GameRoom

☀️Welcome to our fun, newly updated home in a quiet, secure neighborhood in La Mesa ☀️ 🌊Swim in our beautiful blue, solar-heated pool while enjoying an elevated mountain view, perfect for relaxation and fun. Unwind in our fantastic game room, equipped with a pool table, arcade machines and pop-a-hoop, offering endless entertainment for guest at all age. End the day in our in-home movie theater, where you can enjoy your favorite films in ultimate comfort. ☀️

4.9 out of 5 average rating, 285 reviews

A serene outdoor area features a hot tub surrounded by stone elements and a waterfall feature. Sunlight filters through the overhead pergola, creating a play of light and shadow. Lush greenery and a glimpse of a spacious pool can be seen in the background.

Villa in La Mesa

Private Villa: Pool, Slide & Hot Tub

Summary: * Spacious: 5,000 SF indoor living space & 10,000+ SF outdoor living space * Fantastic Pool: Complete with waterslide, cave /grotto & multiple fountains / waterfalls * Relaxing Hot Tub: 5 hours of free heating daily from 5pm-10pm * Event Policy: No weddings, events, or parties with 16 or more guests * Accommodates: This home can accommodate up to 16 guests /see “more things to note" for more info on beds/air mattresses

4.92 out of 5 average rating, 216 reviews

A cozy interior features wooden paneling and a comfortable grey sofa with a decorative pillow. A small kitchenette is equipped with cabinets and appliances. A dining table is set for two, and a guitar is displayed on the wall, adding a touch of creativity to the space.

Guest house in La Mesa

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.

Popular amenities for El Cajon rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.87 out of 5 average rating, 31 reviews

Home in Alpine

Beso De Cielo: Slow Sip Of Solitude

4.88 out of 5 average rating, 112 reviews

Entertainers Dream Pool Home

Superhost

Home in Alpine

4.91 out of 5 average rating, 11 reviews

Maderas Retreat Ranch

An inviting outdoor scene showcases a heated pool illuminated with soft purple lights against a backdrop of mountains. Palm trees frame the area, adding a tropical touch. The warmth of the landscape is accented by nearby subtle lighting, enhancing the evening ambiance.

4.9 out of 5 average rating, 49 reviews

Scenic Getaway w/ Pool, Hot Tub & PS5 GT7 Racing

5 out of 5 average rating, 28 reviews

Home in Jamul

Private Mountaintop Retreat

5 out of 5 average rating, 101 reviews

A landscaped backyard features a pathway of concrete pavers lined with gravel, leading to a seating area with modern outdoor furniture. To one side, a wooden deck provides elevated space with views of the surrounding area and palm trees, complemented by open sky.

Home in Del Cerro

Modern Hilltop Home: Roomy, Views, Family-Friendly

4.91 out of 5 average rating, 218 reviews

A private pool is surrounded by natural stone and lush greenery. Palm trees provide shade, while a bamboo privacy fence enhances the secluded atmosphere. The clear blue water invites relaxation, showcasing gentle ripples under the sunlight.

Home in Chula Vista

Oasis with ocean views/Pool/Hot tub! Sleeps 10!

An outdoor area features a modern pickleball court surrounded by gravel paths and greenery. A set of black lounge chairs and a small table are arranged on a stone patio, inviting relaxation. A swimming pool is visible in the background, framed by palm trees.

4.97 out of 5 average rating, 87 reviews

Private House in the Hills, Pool, Pickleball court

Apartment rentals with a pool

4.89 out of 5 average rating, 539 reviews

A circular pool is surrounded by lounge chairs and vibrant green umbrellas, offering shade and comfort. In the background, the Pacific Ocean is visible, with a clear blue sky above and a few birds flying. Lush landscaping enhances the outdoor space.

Apartment in Del Mar

Studio Condo at Wave Crest Resort

A dining area features a round table with high wooden stools, set against a large arched window showcasing views of the neighborhood. A chalkboard on the wall offers a welcoming message, complemented by light-colored walls and wooden flooring.

4.98 out of 5 average rating, 104 reviews

Ocean-Bay-Sunset View Condo in Pacific Beach!

An arched window frames a serene view of palm trees and distant hills at dusk. The soft hues of a fading sunset create a calming atmosphere. Neighborhood rooftops are visible below, with twinkling lights in the distance hinting at urban life.

4.96 out of 5 average rating, 130 reviews

Bay View Condo in Pacific Beach

Apartment in Solana Beach

Wooden benches are arranged along a railing, offering views of the ocean. A palm tree and planters filled with flowers enhance the serene outdoor space. The clear blue sky contrasts with the calm ocean waters, creating a peaceful setting for relaxation.

4.83 out of 5 average rating, 133 reviews

Del Mar Beach Club-AC, pool,jacuzzi,tennis, views!

A bright and airy living room features large floor-to-ceiling windows showcasing expansive ocean views. Comfortable seating arrangements consist of a plush sofa and armchairs, accented by light decor. A coffee table sits at the center, complemented by side tables with lamps, fostering a relaxing atmosphere.

5 out of 5 average rating, 124 reviews

The Endless Summer Condo!

Apartment in Solana Beach

The image captures a serene beach view, with vibrant purple flowers in the foreground leading to a sparkling ocean. The sun hangs brightly in the sky, casting reflections on the water's surface, while gentle waves lap at the shore in the distance.

4.97 out of 5 average rating, 104 reviews

Beach Luxury at Pelican Point

A bright living room features large glass doors opening to breathtaking ocean views. A comfortable white sectional sofa is surrounded by two plush armchairs. Wall art and a round coffee table enhance the inviting atmosphere, while a potted plant adds a touch of greenery.

4.99 out of 5 average rating, 208 reviews

Luxury Oceanfront Condo with Unbelievable Views

Apartment in Spring Valley

A comfortable living area features a light-toned sofa adorned with colorful cushions and a wooden coffee table. A green chair complements the space, while a decorative wall art piece and potted plant add interest. A dining area is visible in the background.

4.8 out of 5 average rating, 160 reviews

Spacious 2 BR w/ Free Parking & WiFi

Other holiday rentals with a pool

4.83 out of 5 average rating, 18 reviews

Sunset Summit by Coastline Vacation Rentals

5 out of 5 average rating, 22 reviews

Wellness Family Retreat|Sauna|Yoga Room|Firepit

4.98 out of 5 average rating, 97 reviews

A serene pool area is framed by vibrant green foliage and terracotta walls, with lounge chairs positioned nearby. Majestic mountains rise in the background under a clear blue sky. A shaded picnic table is visible, inviting relaxation in a tranquil outdoor setting.

Home in Jamul

Jamul Hacienda | Couples Retreat | Pool & Views!

4.9 out of 5 average rating, 59 reviews

The outdoor space features a custom salt water pool, surrounded by natural rock boulders. LED lights illuminate the water in various colors, with lounge seating and a cabana in the background. Lush greenery adds a serene touch to this inviting oasis.

Home in Lakeside

Hidden Gem! Amazing Resort Style Pool & Spa!

4.89 out of 5 average rating, 75 reviews

A modern outdoor pool area features sleek loungers positioned in water, accompanied by gentle water jets creating a relaxing atmosphere. The spacious patio, framed by a stylish roof, offers seating options and unobstructed views of the surrounding landscape.

Home in Alpine

Luxury Escape | Heated Pool/Spa • Views + Events

4.97 out of 5 average rating, 75 reviews

An elevated view of a spacious backyard reveals a refreshing pool surrounded by lush greenery and palm trees. The home's exterior features solar panels on the roof and ample outdoor seating around the pool, creating a serene oasis for relaxation.

Home in Jamul

Hilltop 2200sqft Oasis: Pool, Views, BBQ

5 out of 5 average rating, 32 reviews

An inviting pool area is shown with a clear blue pool surrounded by tan decking. Lounge chairs are placed nearby, and a pergola offers shaded seating. Lush greenery and distant hillside views enhance the outdoor space under a bright blue sky.

Guest house in El Cajon

Sunset house

Superhost

A spacious pool area is framed by a smooth, curved edge with clear turquoise water. Lush palm trees and colorful potted plants surround the pool, providing a vibrant outdoor setting, enhanced by natural sunlight filtering through the clouds.