Vacation rentals with a pool in Chula Vista

4.99 out of 5 average rating, 140 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

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, 217 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

4.99 out of 5 average rating, 169 reviews

A bright living space features a warm wooden ceiling and large windows. A comfortable orange sofa is paired with a wooden coffee table on a patterned area rug. The kitchen, visible in the background, includes modern appliances and white cabinetry, enhancing the cozy atmosphere.

Home in Hillcrest

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool

2021 CUSTOM guest home with pool in Hillcrest/San Diego Zoo/Balboa Park area. Full kitchen, a queen bed, a queen sleeper sofa, and a crib. Full bath, indoor/outdoor dining, WiFi, smart TV, pool, AC/heating, BBQ& free parking. Walking to restaurants/bars/shops/stores (Trader Joe's, Ralph's & Whole Foods). Under a mile to Farmers Market Sprouts. Minutes' drive to San Diego beaches. No rent for children under 3, only $95/stay. High chair, Pack & Play/Crib, crib mattress, and cover are provided.

4.89 out of 5 average rating, 151 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!

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.

4.88 out of 5 average rating, 114 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.

4.88 out of 5 average rating, 372 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.

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.

4.95 out of 5 average rating, 117 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.

Guesthouse 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.

4.96 out of 5 average rating, 136 reviews

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

This is your 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 beaches, Downtown, La Jolla, Zoo, Stadiums, Sea World, Convention Center + more. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes and furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

4.96 out of 5 average rating, 185 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)

A spacious outdoor area is set beside a shimmering pool, featuring a comfortable sectional sofa with soft cushions and a glass-topped coffee table. An oversized umbrella provides shade, while the surrounding patio is designed for relaxation and enjoyment in a family-friendly environment.

4.79 out of 5 average rating, 174 reviews

Family Home w/Pool, Hot Jacuzzi and Park Access

Spacious, pet-friendly home perfect for families or groups up to 10. Located in a quiet, residential neighborhood with direct access to a large park featuring 2 playgrounds, basketball court, fitness stations, and picnic areas. Enjoy 3–4 car parking, a full kitchen, fast Wi-Fi, and plenty of room to gather. This clean, well-loved home offers comfort, value, and a central location — ideal for those who appreciate space, convenience, and a responsive host.

5 out of 5 average rating, 249 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

COMPLETELY renovated 4BR 3 Bath mid-century home with heated pool, hot tub and fire pit in totally private backyard retreat. We renovated the house top-to-bottom, inside and out and everything is brand new. The beds are top quality with very high quality 100% cotton sheets and bath towels. The house is centrally located in a safe, friendly neighborhood and has beautiful mountain views in the back. Additionally, we do not charge any fees for anything!

4.88 out of 5 average rating, 249 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 La Mesa

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.

Popular amenities for Chula Vista rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 52 reviews

A single-story home is set in a quiet neighborhood, featuring a light-colored exterior and a welcoming front porch. Lush greenery surrounds the property, with several trees and landscaped areas enhancing the spacious outdoor setting.

Home in Bonita

Charming Craftsman Retreat - SD | Pool & Jacuzzi

5 out of 5 average rating, 14 reviews

NEW Airbnb Luxe: Designer Pool, Fitness and Office

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.

4.84 out of 5 average rating, 225 reviews

La Mesa

4.93 out of 5 average rating, 265 reviews

A vibrant heated pool is surrounded by minimalistic landscaping, featuring tall cacti and a clean white fence. Soft lounge chairs are positioned nearby for relaxation. The clear water reflects the blue sky, creating a refreshing setting for leisure and enjoyment.

Home in Mission Hills

Lionhead - Private Boutique Home

5 out of 5 average rating, 28 reviews

The backyard area features a pool and a hot tub, surrounded by palm trees. The two-story home is visible in the background, with outdoor seating beneath a covered patio. Soft lighting adds an inviting ambiance to the evening scene.

Home in Bonita

Breathtaking City Views:Game & Movie Rm w/Pool&Spa

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.

4.96 out of 5 average rating, 26 reviews

Pool house w/Playground, Mini Golf, King Bed

4.97 out of 5 average rating, 102 reviews

Flamingo Sunset House: Sleeps 10: Pool + Hot Tub

A scenic hillside is displayed, featuring a variety of homes nestled among lush greenery. The landscape showcases a blend of residential architecture within a mountainous region, with expansive views of the surrounding area under a clear blue sky.

4.93 out of 5 average rating, 124 reviews

Updated TownHome, Great Location, Fantastic Views

Condo rentals with a pool

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.

4.98 out of 5 average rating, 123 reviews

Bay View Condo in Pacific Beach

An aerial view captures the oceanfront condo alongside the sandy beach, with an expansive coastline stretching below. The surrounding neighborhood features a mix of residential and commercial structures, interconnected by roads and pathways, creating a vibrant coastal community.

4.85 out of 5 average rating, 179 reviews

Ocean front condo heart of pacific beach

4.96 out of 5 average rating, 251 reviews

The kitchen features modern appliances, including a stainless steel refrigerator, microwave, and range. A spacious granite countertop offers ample workspace, while cabinets provide organized storage. The area is brightly lit with recessed lighting, enhancing the clean and functional design.

Condo in University City

Centrally located n UCSD/ utc-laJolla

A wooden deck provides a vantage point overlooking the sandy beach and ocean. The distant condo buildings line the shore, with pedestrians enjoying the beach and pier visible in the background. The scene is illuminated by warm sunset light, enhancing the coastal atmosphere.

4.85 out of 5 average rating, 197 reviews

One Bedroom Ocean Front Condo!

A spacious living area features large windows offering panoramic ocean views and allowing natural light to fill the room. A comfortable blue couch is positioned near a glass coffee table, with a television mounted above a dark wooden entertainment unit.

4.92 out of 5 average rating, 175 reviews

Enchanted Ocean Sunsets

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, 182 reviews

Beautifully remodeled 10th floor oceanfront condo

4.83 out of 5 average rating, 206 reviews

A spacious living area is presented with a large blue sofa facing a mounted flat-screen TV. The kitchen features white cabinetry with modern appliances and a decorative backsplash. A dining area with two high-backed stools is positioned at the counter, alongside a coffee table adorned with a decorative arrangement.

Condo in San Diego

Cozy clean 1 bedroom centrally located by beaches

4.78 out of 5 average rating, 146 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

Other vacation rentals with a pool

The entrance features a welcoming pathway lined with shrubs, leading to an intricately designed front door beneath a porch light. Inside, a spacious game room showcases a pool table and a stylish bar area under modern lighting. The vibrant arcade room is visible, filled with various games. The backyard retreat boasts a sparkling pool surrounded by lounge chairs, with the evening sky enhancing the serene atmosphere.

5 out of 5 average rating, 29 reviews

Surreal Serenity Escape wIth Game Room, Pool & Spa

5 out of 5 average rating, 49 reviews

A clear blue swimming pool reflects sunlight, showcasing gentle ripples on the water's surface. A sandy area is visible at the pool's edge, featuring a small starfish positioned on the light-colored surface.

Apartment in Chula Vista

Serene & Spacious Suite in SoCal/1 Queen bed/Pool

4.99 out of 5 average rating, 84 reviews

A serene pool area features a cascading waterfall illuminated in soft purple hues. The water flows gently into the heated pool, adding a calming effect to the ambiance. Wood paneling surrounds the pool, creating a private and tranquil atmosphere.

Villa in San Diego

Lux Villa: Heated Pool, Sauna, & Gym

4.96 out of 5 average rating, 52 reviews

The entrance is framed by a white door, leading into a well-lit room featuring a spacious bed and a cozy kitchenette with wooden cabinetry. A welcome mat with a floral design sits at the threshold, inviting guests inside.

Tiny home in Encanto

Suburban poolside cozy casita, with a beachy vibe

4.91 out of 5 average rating, 33 reviews

A serene swimming pool is positioned in front of a single-story home with large windows. Lush greenery and palm trees surround the space, creating a private oasis. Outdoor seating is available on the patio, providing a tranquil area to relax.

Guesthouse in Bonita

Casita Bonita

5 out of 5 average rating, 43 reviews

A tranquil outdoor area features a heated saltwater pool surrounded by neat landscaping and a wooden pergola. Comfortable lounge chairs are positioned beside the pool, creating an inviting space for relaxation. Evening lighting highlights the serene atmosphere of the backyard.

Home in Bonita

Heated Pool, Hot tub, Mountain View (Sleeps 10)

An illuminated solar heated pool is surrounded by a safety fence and features a soft blue hue at night. A covered patio area with seating offers a relaxing spot, while string lights enhance the ambiance of the spacious backyard.

4.89 out of 5 average rating, 81 reviews

Big Pool House Oasis (Solar heated pool)

A resort-style pool area is highlighted by a palm tree and soft lighting from string lights above. A pink flamingo float and beach balls rest in the clear water, showcasing a serene evening ambiance.