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San Diego Luxury Vacation Rentals

Start Your Vacation Rental Search > Luxury California Vacation Rentals and Villas > San Diego Luxury Vacation Rentals

Explore the best luxury vacation rental properties in San Diego managed by Gather.

Known for its perfect blend of sun, surf, and vibrant cultural scene, San Diego offers over 70 miles of stunning coastline, from the iconic shores of Coronado Beach to the rugged cliffs of La Jolla. The city’s rich history is showcased in attractions like Balboa Park, home to museums, gardens, and the world-renowned San Diego Zoo. Foodies flock to the Gaslamp Quarter for its eclectic dining scene, while outdoor enthusiasts explore hiking trails in Mission Trails Regional Park or catch waves in Pacific Beach. With its year-round sunshine, incredible beaches, and family-friendly attractions like SeaWorld and Legoland, San Diego is an ideal vacation destination for visitors of all ages. Browse Gather’s San Diego vacation rentals below to find the perfect home, villa, or condo, or view all California vacation properties here.

More Popular California Destinations

Del Mar | La Jolla | Rancho Santa Fe | Napa Valley Area

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The average night price is $709

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    California indoor outdoor living at its finest. It doesn't get better than this! From the entry, welcome the view of the ocean, Mission Bay, Sea World and your own private oasis. Family room with TV and wall opening to the great outdoors Keep an eye on the outdoor kitchen, dining area and pool from this great outdoor area with a retractable awning. Clean bright entry welcomes you home Large central living area with large TV and glass fireplace, wall opens to the outdoor patio areas.
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Slice of Paradise

7 Beds
6.5 Baths
14 Sleeps

Starting at $1,100/night

    Beautiful detailing on the pool Ceiling detailing provide distinct areas while maintaining open plan layout Spacious great room dining area seats six Living room with big TV and multiple media sources, gas fireplace, and unforgettable view Welcoming saltwater lap pool with ocean views Sectional sofa with plenty of seating and living chairs Vintage Bosendorfer Grand Piano

Holiday Availability

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Jewel Above La Jolla Shores

4 Beds
4.5 Baths
10 Sleeps

Starting at $1,900/night

    Sprawling 2-acre luxury retreat with a resort ambiance, the ideal locale for your upcoming staycation. Lavish touches adorn the communal haven, setting a refined tone for memorable convivial moments. Elegant feasts in our large luxurious formal dining area, perfect for grand Gatherings and timeless memories. A large luxurious family room, nicknamed The inviting core of this home, crafted for forging enduring memories with loved ones. With a wine cellar tailored for the discerning wine connoisseur; savor world-class vintages in style. Outdoors one can enjoy the spectacular pool, spa and water features.

Paradise Palm Ranch

6 Beds
6.5 Baths
10 Sleeps

Starting at $2,800/night

    Enjoy the ocean breeze from multiple balconies and outdoor seating areas This home boasts panoramic views extending from Del Mar, Scripps Pier, La Jolla Shores, and around La Jolla to the Cove. Set back on a quiet and private street in La Jolla, this home has some of the best views of any Lookout point. A welcoming entry with seating area to wait for the group to get ready while enjoying the view. A perfect spot to sip your coffee in the morning Coffee table at the living area with scenic views! California's indoor outdoor living at its finest with clean new wood floors throughout the house.
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Coastal Lookout

4 Beds
4.5 Baths
9 Sleeps

Starting at $699/night

    Back yard with firepit and outdoor kitchen Front yard view one block from beach access Living room Living room facing front door Living room from front door (showing Warhol surfboard) Sunroom Sunroom facing dining room
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Roseland Retreat in La Jolla Shores

4 Beds
4 Baths
8 Sleeps

Starting at $550/night

    Indoor/outdoor living between the main living area and the patio. Adorable modern ADU with canyon views overlooking San Diego. Gather and enjoy the fire pit and the lush garden views. Entry living area with California indoor - outdoor living. Two living areas downstairs with modern staircase leading to the bedrooms. Gather around the downstairs family room with King size sofa bed for extra sleeping option. Modern kitchen with everything needed for everyday living.
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Desert View

2 Beds
2 Baths
6 Sleeps

Starting at $200/night

    Entire property view Stunning entrance welcomes you to the villa with a sweeping driveway that is suitable to park up to four cars The magnificent entrance will amaze you the moment you enter The stunning ocean views from every room in the house makes this house our most popular. Step up Dining Room adjacent to the Formal Living Room bringing elegance together Open Living Room with fireplace and electric piano This spectacular villa is truly one of the most amazing luxury vacation rentals you’ll find in Southern California
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Sunset Villa I

5 Beds
4.5 Baths
10 Sleeps

Starting at $749/night

    Elevated glimpse of our inviting sanctuary, beckoning for a memorable stay. Sun-soaked rooftop lounge offers the ideal spot for vacation relaxation with panoramic ocean views. The spacious living area, drenched in sunlight, beckons with its cozy seating—perfect for moments of relaxation or joyous reunions. Experience luxury dining for eight in an elegantly appointed setting. Unwind with breathtaking ocean and nature vistas from the rooftop oasis. Savor a BBQ feast on the rooftop deck, right next to the relaxed lounge area. Sky-high view of our serene retreat nestled amidst nature's splendor.

Scenic Ocean View Guesthouse

2 Beds
1 Baths
5 Sleeps

Starting at $150/night

    Enjoyable living room made cozy by a real fireplace. Entry, living room, dining area and kitchen open and accessible. Dining area right off the kitchen and open to living room. Elegant dining glass table for four with easy access to the patio. The heart of the home: the kitchen area, also comes with direct access the private yard for a seamless indoor-outdoor living. Equipped with stainless steel appliances for your culinary ventures. Plenty of prep spaces, accented with white cabinetry to store your kitchen essentials.
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Seashore Delight

2 Beds
2 Baths
6 Sleeps

Starting at $189/night

    The living area features an airy ambiance with plush sectional sofas, TV and ceiling fan. The open-concept floorplan allows seamless flow and connection. The living area features an airy and modern design style. Enjoy your morning coffee on the patio. The fully-equipped kitchen with stainless steel appliances makes for easy meal preparation. The kitchen area has expansive counter space prepping meals. The dining area in the open concept is perfect for meals.

New Listing!

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Ocean Breeze Cottage 1161

2 Beds
1 Baths
5 Sleeps

Starting at $139/night

    There is a queen size bed and a sleeper sofa that also opens into a queen size bed if needed This beautiful and private studio is located just across the street from the lagoons of Torrey Pines State Beach, surrounded by trees and gentle ocean breezes. Though the studio is 400 sq ft, it is fully equipped with all the standard amenities you might need during your stay The studio comes fully stocked with all the necessary toiletries, towels, dishes, cookware, and utensils Entertainment and relaxation in the living area is complemented with a flat panel Smart TV, high-speed Wi-Fi, and, of course, a full private bath. The kitchen area delights with a full gas range, oven, dishwasher, coffee maker, and space appropriate fridge and freezer Enjoy the peace and tranquility of this quiet residential neighborhood, with your own private yard, entrance, and luscious landscaping.
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Seashore Studio

0 Beds
1 Baths
2 Sleeps

Starting at $139/night

    Enjoy a luxurious stay at The Coulter House. The formal living room, also an antique music room, features high-vaulted acoustic ceilings and luxury appointments, perfect for hosting elegant gatherings or enjoying quiet moments of relaxation. This office space has rich wood accents, a classic chandelier, and ample natural light, perfect for focused work or leisurely reading. Enjoy morning sunlight in the inviting breakfast nook, where relaxed seating for four offers the perfect spot to savor your morning coffee or enjoy intimate, casual dining. Dine in the elegantly appointed dining area with seating for eight. Enter the home through the sunroom, a second living area providing a bright and airy space to relax and unwind. Immerse yourself in the sunroom, where plush seating and warm natural light blend perfectly with captivating outdoor views for a truly serene retreat.

New Listing!

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The Coulter House

6 Beds
5.5 Baths
14 Sleeps

Starting at $700/night

    Welcome to your luxurious home away from home, the Oceanfront La Jolla Cove Condo! With its unbeatable ocean views, cool ocean breeze, and prime location just steps away from La Jolla Village, this stunning 2 bed 2 bath condo is the perfect destination for those seeking a longer stay in one of California's most picturesque coastal towns. The plush sectional sofa is the perfect place to relax and enjoy the breathtaking West Coast sunsets that will grace the coastline nightly. With two bedrooms and two bathrooms, this is the ideal home for longer stays for a small family or couple looking to enjoy the beautiful West Coast sunsets right from their living room. Upon entering the front door, you'll be greeted by a modern and elegant open concept living, dining, and kitchen area. The updated kitchen features European design and all new appliances, including a washer/dryer tucked away near the breakfast nook. Kitchen has Ocean Views
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Oceanfront La Jolla Cove Condo

2 Beds
2 Baths
4 Sleeps

Starting at $324/night

    The Montefaro boasts an impressive 90 walk score as shops, markets, cafés, banks and more are all within easy walking distance. Entrance to the Montefaro Home Style and comfort were top of mind when styling this home This beautifully remodeled 3 bedroom / 3.5 bath condo in the center of the Village is walking distance to all La Jolla's elite shops and restaurants and steps from La Jolla's own Farmer's Market 3rd floor unit with lots of natural light, gas fireplace, separate living room, dining room and laundry closet Comfortable couches, tv and lots of natural light coming in Living Room

Holiday Availability

Montefaro in the Village of La Jolla

3 Beds
3.5 Baths
6 Sleeps

Starting at $350/night

    Perched high above the La Jolla Village, this mid century architectural landmark was designed by renowned Sim Bruce Richard Remley Place features two of Richards' signature brick fireplaces, as well as built-ins and interior works by humanitarian artist James Hubbell Relax on the extended deck and soak in the expansive landscape of the surrounding neighborhood, the Village, and the Pacific Ocean Repose amid tree house vibes, luxury linens, and pacific views in the master bedroom The warm natural light and strong cedar beams greet you as you enter the home through the eclectic living room This thoughtfully designed 4 bedroom, 4 bathroom home will transport you to another era from the moment you walk in the front door. Contemplate life at the sitting desk, surrounded by period books and muffled memories from a century past

Mid Century Masterpiece

4 Beds
4 Baths
8 Sleeps

Starting at $650/night

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