Holiday rentals with a pool in Chula Vista

4.89 out of 5 average rating, 171 reviews

The outdoor pool glows in the evening light, revealing clear water with a unique shape. Surrounding the pool, lounge chairs and umbrellas create a tranquil space for relaxation. A gas fire pit adds warmth to the area, enhancing the captivating view of the cityscape beyond.

Home in Otay Mesa

Ocean View Private Pool & Spa Home w/Putting Green

Welcome to your Private, resort style, pool and spa home with spectacular views day and night! 4 bedrooms, 3 baths (1 King and bathroom with shower on main/ground level and CA King in primary suite. Tropical setting, a short drive to major attractions like our world famous Beaches, Zoo, Sea World, Balboa Park, Downtown, Coronado, Outlet Shopping, & Sesame Place! Soaring 18 foot ceilings in the Living room and Dining room. Outdoor dining, Putting Green, and lounges for resort-like relaxation!

4.98 out of 5 average rating, 138 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

4.96 out of 5 average rating, 181 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.

4.89 out of 5 average rating, 416 reviews

A solar-heated pool glimmers in the sunlight, surrounded by inviting lounge chairs and a shaded umbrella. A cozy outdoor dining area with a table is visible in the background, framed by lush greenery and large eucalyptus trees.

Guest suite in Bonita

Resort-Style Living, Pool, Close to All San Diego

Nestled in a quiet, discreet neighborhood, our private air-conditioned studio offers a safe & serene retreat. Attached to a stunning ranch-style executive home, it features an amazing pool for your relaxation. We are conveniently located a short distance away from the Gaylord Convention Center, the Olympic Training Center, downtown San Diego, Comic-Con, major attractions, concert venues, beaches, airport & Mexico. Enjoy a complimentary butler tray that includes coffee, tea & snacks.

An inviting outdoor space is presented with a private heated pool and a spacious deck. Comfortable lounge chairs face the pool, while a dining table with red umbrellas offers shade. Lush greenery surrounds the area, enhancing the sense of privacy.

4.85 out of 5 average rating, 128 reviews

Dream Vacation! Sunny 3 Bedroom Home!

Beautiful family vacation retreat! Amazing backyard includes your own private heated pool, a spacious deck for relaxing with lounge chairs, dining spaces, and fire table. Fenced for privacy. Inside enjoy the game room and arcade, smart TVs located throughout the house, and air conditioning. Strong Wi-Fi signal, including the outdoor deck area. Amazing location close to all SD has to offer: within 20 minutes of the zoo, beaches, Sea World, downtown, and the airport! Private parking.

A modern living room features a light wooden floor and white walls, complemented by a pink accent wall. A flat-screen TV is mounted above a stylish cabinet, with two potted plants on top. A comfortable seating area includes a rattan chair and a coffee table.

4.91 out of 5 average rating, 154 reviews

Casa Bahia Beautiful San Diego Home with Pool

Welcome to Casa Bahia! Our home has been completely upgraded and is ready to host your perfect getaway. Conveniently located close to the Chula Vista Bayfront and 10 minutes to downtown San Diego or the beach. Our home features a kitchen with top of the line appliances, brand new furniture, 4 bedrooms, 2 full bathrooms, a large pool, a yard with a lounge area, BBQ, and a clean peaceful feel. In addition, our stylish and minimalist place to stay is perfect for group or family trips.

4.99 out of 5 average rating, 114 reviews

A spacious two-story home is depicted, featuring a swimming pool surrounded by a safety fence. The exterior showcases large windows and a well-maintained patio area with comfortable seating. The landscape includes lush greenery and decorative features, providing a serene atmosphere for outdoor relaxation.

Home in Bonita

Beautiful Scenic Views of Coronado Bridge!

Relax with the whole family at this peaceful stylish retreat with scenic views of downtown, Coronado Bridge and the ocean. Enjoy your vacation to the fullest at this one if a kind two story, 6BR/4.5BA home! The luxurious interior features two spacious living spaces, a stunning game room and an outdoor entertainment area. The options are endless - join loved ones in a game of billiards in the game room. Enjoy a cookout with your family after a sun-drenched afternoon in the pool!

A spacious living room features a plush sectional sofa with an assortment of decorative pillows. A modern coffee table made from natural wood sits on a patterned area rug. Large sliding doors allow light to enter and provide views of the outdoor pool area.

4.9 out of 5 average rating, 148 reviews

An Oasis,Heated Pool, JQZ,Grill,Ocean&MTN View

Welcome home to this gorgeous remodeled and upgraded single story 3-bedroom, 2 bath panoramic view property in the heart of Chula Vista. This home is absolutely perfect to soak up the sun, relax or stay pool side and work remotely. As you walk up to the home you will notice a stunning manicured palm tree and a beautiful landscaping. Warmth and light welcome you into the spacious Living Room which offers a wall-to-wall sliding door that overlooks the back yard and the pool.

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

4.92 out of 5 average rating, 235 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 Bonita

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

Enjoy this stunning family friendly home with beautiful views! From the front deck you have beautiful ocean views and bay views. You can also have views of Coronado bridge and downtown. This large family friendly home is well-appointed with 3 bedrooms, 2 baths, and two living rooms that has an air mattress to comfortably sleep 10 guests. There are spacious areas for gathering, private poolside oasis with beautiful views.

4.95 out of 5 average rating, 110 reviews

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.

Home in San Diego

San Diego Pool House with Luxury King/Queen Suites

Indulge in this luxurious 4-bed 3-bath home! The perfect escape for families and groups of friends seeking comfort and style. Accommodating up to 10 people, this stunning home is complete with king and queen suites plus a backyard pool oasis. Located just 10 minutes from downtown San Diego, whether you seek relaxation or excitement, you'll find it all right here! Book now for a truly extraordinary experience.

A view of the inviting swimming pool surrounded by a spacious patio. Natural rock elements and vibrant landscaping enhance the outdoor area. The multi-level deck is visible, offering seating options and picturesque canyon surroundings under a clear blue sky.

4.89 out of 5 average rating, 223 reviews

The Queen House

Welcome to Endless Summer, your ideal family retreat! This beautiful 4-bedroom, 2.5-bath home is just 15 minutes from Downtown San Diego, near attractions like Petco Park, the San Diego Zoo, and local beaches. Located in Mount Helix, La Mesa, enjoy stunning canyon views and a refreshing swimming pool with a waterfall. Experience a unique stay at a home that has it all!

Popular amenities for Chula Vista rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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 !

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

4.92 out of 5 average rating, 102 reviews

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.

Home in San Diego

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

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

5.0 out of 5 average rating, 303 reviews

A private outdoor area features a heated pool surrounded by lush green grass and modern loungers. An inviting fire pit is centrally located, with two stylish chairs positioned nearby. The backdrop includes well-maintained shrubbery and tall trees, enhancing the tranquil ambiance.

Home in Serra Mesa

Midcentury Lux 4BR home w Pool/Spa/Cabana/Firepit

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

4.9 out of 5 average rating, 173 reviews

A spacious living area is highlighted by vaulted ceilings and floor-to-ceiling windows offering expansive city views. Modern seating includes a light grey sofa, orange armchairs, and a round white coffee table. The open kitchen is visible in the background, featuring bar seating and contemporary finishes.

Home in Mission Hills

Heated Pool|Jacuzzi|King Bed|City Views|Chic Decor

4.92 out of 5 average rating, 131 reviews

A spacious outdoor patio showcases a private pool and hot tub, surrounded by comfortable seating and a fire pit. An activity area features games such as foosball and cornhole, with lounge chairs positioned for relaxation. Lush green landscaping complements the inviting space.

Home in Bay Park

Modern Central SD Home w/ Pool & Spa Near Beach

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

4.92 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 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, 144 reviews

The Endless Summer Condo!

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

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

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.

4.98 out of 5 average rating, 226 reviews

Luxury Oceanfront Condo with Unbelievable Views

A bright living area features a large window with ocean views and light blue skies. A wooden coffee table rests on a patterned rug, surrounded by comfortable seating. A flat-screen TV is located on a white media console, enhancing the room's modern look.

4.97 out of 5 average rating, 208 reviews

Beautifully remodeled 10th floor oceanfront condo

Other holiday rentals with a pool

4.99 out of 5 average rating, 185 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

Apartment in Downtown San Diego

Breathtaking Ocean, Bay, City & Petco Park Views

4.97 out of 5 average rating, 100 reviews

Apartment in Downtown San Diego

A round wooden dining table occupies the center of the room, accompanied by black chairs. A decorative planter rests on the table, featuring vibrant green succulents. Large glass doors lead to a cozy lounge area, enhancing the open feel of the space adorned with natural materials.

Downtown Dream 4

4.8 out of 5 average rating, 122 reviews

A vibrant outdoor playground features a wooden play structure with a slide, swings, and colorful accessories. Adjacent, a spacious living area showcases a sectional sofa and decorative wall art, illuminated by natural light. The backyard pool area includes yellow umbrellas and lounge chairs, providing a relaxing spot. A mini-golf setup is visible, complete with flags and a maintenance shed.

4.97 out of 5 average rating, 66 reviews

Pool house w/Playground, Mini Golf, King Bed

4.86 out of 5 average rating, 21 reviews

California Sun & Saddle

5.0 out of 5 average rating, 12 reviews

Beautiful Chula Vista Retreat

4.87 out of 5 average rating, 15 reviews

Home in Otay Mesa

Seabird Retreat | 5b 3ba | Pool, Jacuzzi, BBQ