Holiday rentals with a pool in Chula Vista

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

Luxury Oceanfront Condo with Unbelievable Views

Welcome to your oasis! Prepare to be awestruck by the breathtaking views at Sunset Pacifica. This fully renovated condo features two ensuite bedrooms with the beachy SoCal vibe you desire. Ideally located on the boardwalk, you're minutes from La Jolla, Downtown, the San Diego Zoo, Embarcadero, and top restaurants, bars, and entertainment spots. Whether you're in the mood for exploration or relaxation, you'll find it here- lounging poolside or on the sandy shores of the stunning Pacific Ocean.

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.

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.

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.

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.

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.

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.

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.

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.

Luxe Home w. Serene Backyard Spa

Escape to the heart of San Diego in our chic and luxurious 3-bed oasis, where upscale meets laid-back California cool. Steps from vibrant eateries, buzzing bars, and unique boutiques, this retreat offers a serene backyard with a soothing spa. Experience local attractions, beaches, and the San Diego Zoo, all a short drive away. Your ultimate San Diego adventure awaits!

Cozy home central to beaches & attractions

Cozy and stylish 1-bedroom condo. Centrally located, with quick access to freeways and on-site parking, nearby popular shopping malls, travelers can easily drive to San Diego Downtown, Beaches, San Diego Zoo, SeaWorld, Balboa Park and La Jolla in under 15 minutes. This place has new furniture and amenities and only 5 minutes’ walk to the trolley station.