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Holiday rentals with a pool in Chula Vista

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chula Vista

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guesthouse in City Heights

4.91 out of 5 average rating, 275 reviews

Green Door Cottage

Enjoy our new, fully renovated (2021) tiny Cottage which holds a timeless charm and is also filled with a modern touch. Close to all the wonderful things San Diego has to offer - beaches, downtown, the zoo, Padres games, SeaWorld, SAN airport, Old Town, SDSU, you name it! Nice sized turf yard with total privacy and an amazing back deck! Outside table and fire pit are perfect for the cool nights of San Diego. If you need more space, check out our other listing, Pink Door Craftsman (sleeps 7)!

Guest favourite

Home in Otay Mesa

4.87 out of 5 average rating, 133 reviews

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 bedroom and bathroom with shower on main/ground level). Tropical setting, and just a short drive to major attractions like our world famous Beaches, Zoo, Sea World, Balboa Park, Downtown, Coronado, Outlet Shopping, Sesame Place and even Mexico! Soaring 18 foot ceilings in the Living room and Dining room. Outdoor dining, Putting Green, and lounges for resort-like relaxation.

Condo in Serra Mesa

4.84 out of 5 average rating, 193 reviews

Cozy clean condo near beaches central location

Enjoy your getaway to San Diego in a clean & spacious one bedroom, one bath condo within minutes of all attractions this beautiful city has to offer! First floor condo conveniently located near major malls, beaches, restaurant hubs, airport, freeways and more! Peaceful, comfortable and quiet, with all the amenities you need. Head down to the community pool or visit one of the many beaches or hiking trails nearby to soak up some sun. We trust you’ll create memories that’ll last a lifetime!

Condo in Eastlake

4.83 out of 5 average rating, 126 reviews

1BR Apartment in beautiful Eastlake, Chula Vista.

Beautiful, recently furnished and renovated apartment. Peaceful location on East Lake, Chula Vista. Within walking distance to the lake. Close to Eastlake Village for banking, shopping, restaurants and stores. This area itself and nearby areas offer all visitors a wide array of attractions all year round. Some nearby attractions are on a 23 mi range (Uber or Lyft), such as: San Diego’s downtown, Balboa Park, San Diego Zoo, Coronado beaches and many more amazing places that San Diego offers.

Guest favourite

Home in Chula Vista

4.9 out of 5 average rating, 155 reviews

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. Also where most listings have 10% TOT tax we do not.

Guest favourite

Guesthouse in Mission Hills

4.91 out of 5 average rating, 428 reviews

Mission Hills Charming suite, walkable to all.

Heart of Mission Hills, upscale area, this private guest suite, separate from the house, is perched above the pool (separate building from main house), own entrance; sure to provide privacy. We are minutes from airport, walking distance to coffee & restaurants and central to all of SD. Please note this property is wiped down after each visit with Clorox as well as all linens washed. We also don’t rent back to back giving time for thorough cleaning.

Home in Chula Vista

4.76 out of 5 average rating, 111 reviews

Family Home w/Pool, Hot Jacuzzi and Park Access

This large home is great for families and large groups of up to 10 people. The quiet and tidy neighborhood, along with all the amenities and the beautiful park next to it will keep everyone entertained, regardless of age. You have Direct Access to a Community Park with Two Child Playgrounds, a Full-Sized Basketball Court, Fitness Courses, and Picnic Area. PARKING included for up to 3-4 cars Pets are allowed for a fee

Guest favourite

Guesthouse in La Mesa

4.9 out of 5 average rating, 161 reviews

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.

Guest favourite

Guest suite in Bonita

4.87 out of 5 average rating, 317 reviews

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

Large, private air-conditioned studio attached to beautiful ranch-styled, executive home with amazing pool. Resort-style living. Unwind & relax by the pool and gardens. Close to the Olympic Training Centre, downtown SD, Comic Con, major attractions, beaches, airport & Mexico. Coffee, tea and snacks are provided in the room for your enjoyment! Lots of off street parking. Safe neighborhood.

Guest favourite

Guesthouse in Allied Gardens

4.94 out of 5 average rating, 356 reviews

The BEST NEST Clean, peaceful, private, affordable

This lovely private & separate unit is comfortable, clean and convenient. Your completely private suite is accessible via your own entrance. Minutes from major attractions, away from the hustle and bustle. Full kitchen for easy meal preparation. Located in a nice usually quiet neighborhood, close to major freeways. Enjoy the gorgeous San Diego weather in the quaint outdoor patio area.

Guest favourite

Home in Chula Vista

4.87 out of 5 average rating, 216 reviews

South Bay cozy retreat with jacuzzi!

- All the comforts of a modern home in the suburbs, all the charm of an old house in a well established neighborhood!! Family Oriented Vacation Rental that feels like your home away from home. Less than 20 minutes away from downtown San Diego and Beaches! 10 adults , 12 max total. Ask about the 4 night or more promotion!

Home in Paradise Hills

4.86 out of 5 average rating, 174 reviews

*Luxury Home* Salt Water Pool* Hot Tub* Fire Pit*

This is a five bedroom 3 bath home! There is a pool and spa with nice back yard! The whole downstairs is available to rent with the 4 bedrooms and 2 bathrooms. It will sleep 8 people comfortably. The up stairs is not accessible and is a separate apartment. Nobody is staying there while it’s booked.

Holiday rentals for every style

Get the amount of space that is right for you

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Luxurious estates for the ultimate escape

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A space that's all yours, with room for everyone

Popular amenities for Chula Vista rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in El Cajon

4.97 out of 5 average rating, 110 reviews

Top hills, luxury, Sunset View, 4 BR, Pool/Spa

Guest favourite

Home in Bay Park

4.98 out of 5 average rating, 255 reviews

Resort Style Living with Pool, Spa, and Bay Views!

Home in University Heights

4.94 out of 5 average rating, 112 reviews

Your Modern Lux Pool Resort in the Heart of SD

Guest favourite

Home in Mission Hills

4.93 out of 5 average rating, 219 reviews

Lionhead - Private Boutique Home

Guest favourite

Home in San Diego

4.94 out of 5 average rating, 167 reviews

Stunning San Diego Home w/Pool,Spa,Outdoor Oasis

Guest favourite

Home in La Mesa

4.9 out of 5 average rating, 104 reviews

The Oasis in La Mesa W/Salt Water Pool! Sleeps 8

Guest favourite

Home in La Mesa

4.93 out of 5 average rating, 115 reviews

Updated TownHome, Great Location, Fantastic Views

Guest favourite

Home in Hillcrest

5 out of 5 average rating, 117 reviews

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool

Condo rentals with a pool

Guest favourite

Condo in Del Mar

4.91 out of 5 average rating, 164 reviews

1 Bedroom Condo at Wave Crest Resort

Guest favourite

Condo in Pacific Beach

4.97 out of 5 average rating, 109 reviews

Bay View Condo in Pacific Beach

Condo in Pacific Beach

4.86 out of 5 average rating, 134 reviews

Ocean front one bedroom condominium

Guest favourite

Condo in University City

4.95 out of 5 average rating, 216 reviews

Centrally located n UCSD/ utc-laJolla

Condo in Pacific Beach

4.85 out of 5 average rating, 165 reviews

One Bedroom Ocean Front Condo!

Guest favourite

Condo in Pacific Beach

4.91 out of 5 average rating, 126 reviews

Enchanted Ocean Sunsets

Guest favourite

Condo in Pacific Beach

4.98 out of 5 average rating, 126 reviews

Luxury Oceanfront Condo with Unbelievable Views

Guest favourite

Condo in Pacific Beach

4.96 out of 5 average rating, 148 reviews

Beautifully remodeled 10th floor oceanfront condo

Quick stats about holiday rentals with a pool in Chula Vista

Total rentals
240 properties
Total number of reviews
8K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Wi-Fi availability
230 properties include access to Wi-Fi

Destinations to explore