Vacation rentals with a pool in El Cajon

An outdoor area features a clear saltwater pool surrounded by elegant lounge chairs. A shaded umbrella stands nearby, and the landscape includes rolling hills and a distant view of the mountains, providing a serene backdrop for relaxation.

4.94 out of 5 average rating, 156 reviews

Fletcher Hills luxury, Sunset View, 4 BR, Pool/Spa

✨ Luxury Hillside Retreat | Private Entrance | Saltwater Pool & Spa Enjoy this luxuriously furnished 4-bedroom, 2-bath home in Fletcher Hills, CA, perched on a hill with stunning mountain and San Diego city views. Relax in your private saltwater pool and jacuzzi with color-changing LED lights, or unwind indoors with full kitchen access, high-speed Wi-Fi, and smart TVs with Netflix. Perfect for couples, business travelers, and families, this cozy yet elegant retreat makes you feel right at home.

4.99 out of 5 average rating, 184 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.

Guesthouse 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

4.98 out of 5 average rating, 137 reviews

A well-appointed backyard features a heated pool with a waterfall, surrounded by palm trees and lounge chairs. An outdoor dining area is under a covered gazebo, providing a view of the landscaped space. Soft evening light hints at a serene atmosphere.

Home in Spring Valley

Tropical Oasis: spa, solar heated pool, waterslide

This home is ideal for FAMILY trips and QUIET friend groups Hours of entertainment in the private backyard that includes heated pool, waterslide, grotto, spa, gazebo, half bath, BBQ, and more. Clean and spacious home with over 2,100 sqft of living space. Minutes from everything San Diego has to offer. Distance to main attractions: SDSU- 5 mi Downtown/PetcoPark park-11 mi SD Zoo/balboa park-12 mi SD Airport- 13 mi Old town- 14 mi Coronado-15 mi Belmont park/Mission beach-18mi Sea world- 18mi

A spacious outdoor area features a clear blue pool surrounded by palm trees. Lounge chairs are positioned nearby, and a shaded table with chairs offers a spot for relaxation. The backyard showcases a privacy fence and ample sunlight.

4.85 out of 5 average rating, 263 reviews

San Diego Pool | Fire Pit | Sunshine | Sleeps 10

Escape to a fresh 4-bedroom retreat for family and friends (10 ppl max). Updated in January of 2024 with new furniture, and fixtures. Bask in the sun on the deck, take a dip in the pool. Enjoy the private and fenced backyard, BBQ, or the recently renovated and modern Kitchen. This home is perfect for vacations or remote work. Explore San Diego beaches and all the area has to offer, the most popular tourist destinations are all within a 20-30 minute drive. 20 minutes to the beach! Book with us!

4.96 out of 5 average rating, 180 reviews

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 La Mesa

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 dining area is highlighted by a round wooden table surrounded by six wooden chairs. A cozy blue sofa is positioned nearby, with large glass doors opening to a pool area. Natural light enhances the space, complemented by a modern pendant light overhead.

4.92 out of 5 average rating, 102 reviews

San Diego Oasis- A Retro Retreat w/ King Size Bed!

Welcome to San Diego Oasis, a retro retreat--a mid-century modern oasis in sunny San Diego! This stylish home combines classic charm with all the modern upgrades you desire. Unwind by the sparkling pool, enjoy a friendly game of air hockey or corn hole, board games or enjoy s'mores around the gas fire pit . The retro retreat is the perfect blend of comfort, convenience, and timeless design. SD's most popular attractions are all within a 20-30 minute drive. Only 20 minutes to the beach!

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, 205 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.

4.98 out of 5 average rating, 127 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!

The Casita retreat is a guesthouse situated among a private 20 acre oasis surrounded by majestic mountain views and a citrus grove 30-40 minutes from San Diego. The space is designed for nature enthusiasts to retreat from the daily hustle and bustle and find peace and slowness. Come take a pause, relax poolside, pick citrus (when in season), enjoy nearby trails, and wineries. The sunsets and starry skies are breathtaking. We hope you get to experience their magic for yourself.

Villa in Rancho San Diego

An inviting outdoor entertainment area features a heated saltwater pool surrounded by elegant lighting and stylish lounge furniture. Inflatable swan floats rest in the water, while vibrant umbrellas provide shade over seating. Lush landscaping enhances the serene environment, making it ideal for relaxation.

Enchanted Paradise! Pool+Spa+Outdoor Kitchen

Brand New Property! Massive garden of Eden style resort home with sprawling outdoor entertainment area and spacious open concept inside, perfect for large families with kids and responsible adults. Updated top to bottom with all new outdoor and indoor furniture, modern upgrades in all bedrooms and common areas. Centrally located and 20 minutes from the beach and all of SD's top attractions! 8 person hot tub, sparkling saltwater pool and new outdoor kitchen. Don't miss out!

4.92 out of 5 average rating, 215 reviews

4.96 out of 5 average rating, 227 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)

Villa in Rancho San Diego

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.

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

4.9 out of 5 average rating, 297 reviews

4.96 out of 5 average rating, 178 reviews

Beautiful 3,000 Sq Ft Tropical Oasis

Beautiful 4 Bedroom, 2 1/2 Bath Family Home Located in Tranquil Fletcher Hills. This 3,000 sq. ft. Home is Perfect for large families who wish to Relax in a Peaceful Setting. 24-hour self check-in keypad after 4pm and check-out at 11AM. Host does not allow parties/events. This is NOT a Party House! This home is located in a quiet residential neighborhood, Guests who do not respect this will be asked to leave.

Popular amenities for El Cajon rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 98 reviews

Home in Alpine

Montecito Cottage - Tuscan Farmhouse, Pool, Views

A private pool is surrounded by a spacious patio, featuring a built-in spa and floating pool accessories. Lounge chairs are arranged by the poolside, while the nearby house is complemented by green shrubbery and playful palm trees. Bright sunlight highlights the inviting blue water.

4.9 out of 5 average rating, 115 reviews

QUIET HOME -3 Bedroom & Den, + POOL, sleep 8 plus

A serene outdoor space features a salt-water pool surrounded by a concrete patio and manicured grass. An umbrella provides shade over the poolside area, with lush greenery and mountains visible in the background under a partly cloudy sky.

4.87 out of 5 average rating, 239 reviews

Bright and spacious home with views, pool & spa.

Double glass doors provide access to the patio, revealing views of a kidney-shaped pool surrounded by a deck. Lush greenery and hills are visible in the background, creating a serene outdoor setting.

4.77 out of 5 average rating, 137 reviews

Views - Quiet Mt. Helix Home - Pool -Sleeps 11

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.

4.93 out of 5 average rating, 252 reviews

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

A spacious backyard is showcased with a glistening pool surrounded by a concrete deck. Green grass offers a soft contrast, while lounge chairs and a shaded seating area are positioned for relaxation. String lights illuminate the space, enhancing the outdoor ambiance during twilight.

4.95 out of 5 average rating, 110 reviews

San Diego Pool House with Luxury King/Queen Suites

A serene outdoor space showcases a sparkling pool adjacent to a jetted hot tub, with canyon views stretching in the background. A glass fence enhances the vista, and the surrounding landscape features palm trees and gentle hills under a clear blue sky.

4.98 out of 5 average rating, 116 reviews

ModernCoastal I View I Pool ITub

A serene outdoor pool area features a refreshing blue pool surrounded by terracotta tiles. Two lounge chairs are positioned nearby, inviting relaxation. A wooden fence offers privacy while views of the landscape and sky are visible in the background, creating a tranquil atmosphere.

4.81 out of 5 average rating, 104 reviews

The Agave House | Mountain Views & Pool

Condo rentals with a pool

4.78 out of 5 average rating, 170 reviews

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.

Condo in Spring Valley

Spacious 2 BR w/ Free Parking & WiFi

4.82 out of 5 average rating, 126 reviews

A light-filled living area features a comfortable white sofa adorned with various pillows. A small marble table sits in front of the sofa, complemented by fresh tulips in a vase. A side chair and decorative elements add to the inviting ambiance.

Condo in La Mesa

Sweet Little La Mesa Condo(pool+hot tub) NEAR SDSU

4.92 out of 5 average rating, 200 reviews

A cozy living room features a comfortable gray couch adorned with a woven throw, complemented by a small circular table and a patterned area rug. Natural light floods the space through glass sliding doors that lead to a balcony with seating, framed by soft curtains.

Condo in Mission Valley

Cozy home central to beaches & attractions

A spacious living area features large glass sliding doors that reveal an expansive ocean view with a sunset. Comfortable seating includes a modern gray sectional and two accent chairs, inviting relaxation. The room is illuminated with warm, natural light, enhancing the serene coastal atmosphere.

4.94 out of 5 average rating, 336 reviews

Beach Front Condo - Capri by the Sea - Remodeled

A spacious living area is showcased with a comfortable leather sofa and a decorative rug. A dining table with four chairs is positioned near floor-to-ceiling windows, offering natural light. Art pieces adorn the walls, complementing the inviting atmosphere.

4.92 out of 5 average rating, 217 reviews

Windows to the Ocean

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.

5.0 out of 5 average rating, 143 reviews

The Endless Summer Condo!

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.

4.97 out of 5 average rating, 143 reviews

Bay View Condo in Pacific Beach

4.89 out of 5 average rating, 569 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.

Condo in Del Mar

Studio Condo at Wave Crest Resort

Other vacation rentals with a pool

4.93 out of 5 average rating, 234 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.

Guesthouse in La Mesa

La Cabana

4.98 out of 5 average rating, 115 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.

Guesthouse in Jamul

San Diego Mountain Retreat

4.89 out of 5 average rating, 280 reviews

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 El Cajon

Tranquil Poolside Studio

Guest suite in Spring Valley

A spacious pool area is surrounded by palm trees, featuring a clear swimming pool with a gentle slope and a water slide. A decorative mural with tropical motifs can be seen on the adjacent wall, enhancing the outdoor recreational space.

2 Bdrm, Kid-Friendly, Yard, Pool, Play, & Spa!

4.97 out of 5 average rating, 261 reviews

4.95 out of 5 average rating, 55 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.

Guesthouse in El Cajon

Casa sunset

4.94 out of 5 average rating, 89 reviews

@Stunning European Villa with amazing view, slide

5.0 out of 5 average rating, 18 reviews

Home in Lakeside