Villa holiday rentals in San Diego County

5 out of 5 average rating, 6 reviews

Amazing WaterView Penthouse w/AC

AMAZING WATER VIEW PENTHOUSE!! Over 300 5 star reviews from our listings! Perfect for Executives, Quiet mature couples, Healthcare Professionals, Physicians/Traveling Nurses. Immaculate Luxury/Centrally-located. Peaceful, family friendly, every amenity. Private hot tub/private deck/patio furniture/private bbq grill/private fire pit/5 Star Resort Experience/robes/slippers, hot tub towels, fully stocked kitchen/pots/pans/spices/cookware/stemware/dishes/flatware/WiFi/Smart TVs/cable/Netflix/YouTube

5 out of 5 average rating, 64 reviews

A gated villa is set against a hillside backdrop, featuring a blend of stone and stucco exteriors. A covered terrace with seating offers views of the surrounding landscape, while grapevines and trees add greenery. A vibrant sunset illuminates the sky, enhancing the serene ambiance.

Villa in Vista

Vineyard Retreat—Free Hot tub & EV Charger—Views!

Welcome to your private, gated oasis in the hills of Vista! Soak in the jetted hot tub while the sun sets into the ocean, recharge your EV overnight—at no charge, and wake up to breathtaking panoramic views. Immerse yourself in the peace of the natural surroundings, enjoying changing views—and a sunset terrace you’ll never want to leave. Whether you need to unwind from the hustle and bustle of daily life, or to work remotely in a peaceful setting. This space is crafted for unforgettable stays.

4.92 out of 5 average rating, 149 reviews

An outdoor area features a hot tub and a spacious pool surrounded by lounge chairs. The setting is illuminated by soft lighting, with the desert landscape visible in the background under a twilight sky.

Villa in Borrego Springs

Rams Hill Golf Retreat - Hot Tub, Stargazing

Escape to Casa Estrella, your private Borrego Springs sanctuary with the largest pool in the area—80 feet of sparkling paradise. Perched in the prestigious Rams Hill Golf community, this modern Spanish villa offers 3 bedrooms, 3 baths, hot tub, fire pit, and unforgettable stargazing under certified Dark Sky protection. Golf on your doorstep, hike Anza-Borrego State Park trails, or simply float in your massive pool watching the sun set over desert mountains. Your ultimate desert retreat awaits.

A spacious outdoor area features a clear swimming pool surrounded by a patio. Lush palm trees and other greenery create a private atmosphere. A gazebo and dining seating area are visible, providing a relaxing space for gatherings and leisure.

4.91 out of 5 average rating, 104 reviews

6-bed Paradise Villa Pool, hot-tub massage chair

*EV charging available Welcome to Casa Cerro-my incredible chic high-tech modern villa in San Diego! This stylish place to stay is perfect for families and group trips. Its open and airy layout can accommodate up to 11 people. This completely remodeled home is furnished with all the luxuries of home and more that is powered by an iPad for you to use. I love technology. But don't worry you don't have to use it to power up the house, everything has traditional switches/remotes if you choose.

4.91 out of 5 average rating, 183 reviews

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.

Villa in El Cajon

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 gas heated saltwater pool and new outdoor kitchen. Don't miss out!

4.96 out of 5 average rating, 110 reviews

A sparkling blue pool is surrounded by a spacious patio featuring lounge chairs and umbrellas. Two pink flamingo floaties rest in the water, complemented by palm trees and sunny skies. The area is designed for relaxation and enjoyment, with a small jacuzzi nearby.

Villa in Oceanside

Villa Descanso: 15 min to beach, heated pool, BBQ!

Are you seeking for your own private enclave only 15 minutes from Oceanside beach? “Villa Descanso” as featured on HGTV's "House Hunters" is a vacation destination in itself featuring high end luxury finishes, relaxing crystal clear pool and spa, ultra comfortable beds, large indoor and outdoor dining spaces fully equipped for the perfect getaway. Once you arrive you won't want to leave! But if you do, you are just 6.5 miles away from the beach! Book NOW! You're going to love it!

4.98 out of 5 average rating, 59 reviews

A concrete pathway leads to the entrance of the villa, bordered by lush landscaping featuring ornamental grasses and desert plants. The exterior is illuminated by soft lighting, highlighting the contemporary architecture against a vibrant twilight sky.

Villa in Fallbrook

Casa Nera | Movie Theater · Pool · Hot Tub · Sauna

Couples, Families, & Countryside Peace Seekers only, please. Casa Nera (“Black House” ~ Italiano) is truly a one-of-one. It is where contemporary mid-century inspired architecture, unparalleled design, stunning vistas, and the finest amenities converge. Overlooking a 5-acre avocado grove, Casa Nera presents a pool & spa, private cinema, outdoor cedar barrel sauna, and over 7,000 ft² of indoor/outdoor living, gaming, & playing. Brilliantly designed by SoCalSTR® | IG: @socalstr

4.96 out of 5 average rating, 205 reviews

An aerial view of the expansive villa is presented, revealing its terracotta roof and surrounding orchards. The clear pool area is visible, bordered by palm trees, with a circular driveway leading into the property. The landscape includes various green patches and dirt pathways.

Villa in Fallbrook

Via Viento Farms

Via Viento Farms is more than a destination; it's an escape from the ordinary. Whether you seek a weekend retreat or a Family vacation. Via Viento Farms welcomes you with open arms. Immerse yourself in the beauty of the orchards, indulge in the luxurious amenities, and let the spirit of the farm rejuvenate your senses. A 5 ensuite bedroom in an expansive 4000 sq foot Villa. Featuring an expansive pool, a Swedish sauna, and an 8-person hot tub, and Private Pickle Ball court

Superhost

4.9 out of 5 average rating, 59 reviews

Backyard Oasis • Pool • Hot Tub • Games • MiniGolf

If you’re looking for a place where everyone can relax and have fun, this is it. Designed for memorable stays, enjoy pool days, hot tub nights, games, and mini golf in the spacious backyard. Inside, bright, modern interiors offer comfort and space to unwind. Located in one of San Diego’s safest and most family-friendly neighborhoods, this home delivers resort-style vibes in a private setting made for enjoying time together. Ideal for families, friends, and groups!

5 out of 5 average rating, 122 reviews

Aerial view of the Hilltop Villa showcases its expansive structure surrounded by lush avocado trees. The inviting pool glimmers, with scenic vineyard valleys and hills visible in the background under a vibrant blue sky adorned with fluffy clouds.

Villa in Fallbrook

Heated Pool Oasis Hilltop Villa, Avo Grove, Views

UPDATE: PICKLEBALL COURT WILL BE AVAILABLE STARTING FEBRUARY 1, 2026 Relax, unwind and create special memories with loved ones in this little slice of paradise. Feel the gentle breeze, pleasant sun rays, rustling avocado leaves and amazing vineyard valley views (Monserate Winery is just below us) on this climate sweet spot hilltop sanctuary. Many guests forgo their planned activities and rather chill by the pool paradise to enjoy unmatched tranquility.

The property displays a charming two-story building with arched balconies and a red-tiled roof. A spacious patio features vibrant outdoor furniture, including a large umbrella, providing shaded seating. The modern garage blends seamlessly with the structure, further enhancing the property's appeal.

4.93 out of 5 average rating, 150 reviews

The Crown Jewel Villa with AC!Bikes,Kayak and SUP!

Escape to the peaceful and coveted beach community of Crown Point in San Diego! This highly sought after neighborhood boasts mostly permanent residents, creating a serene and tranquil environment for our guests. Right across the street from the home, you can find Ski Beach and Park, a favorite spot for families and kids. Explore the variety of local eateries and coffee shops, or take a short walk to popular Sail Bay and the ocean.